When David Bowie and T Rex were making waves in music and their hair my characters find a new way of living. Another dip into the world inside my imagination. Not sure the pictures will copy, sorry if they have not.
Back in the 70s we were a normal sort of couple, my wife Bev was a busy sales person who was good at her job, looked good and was my best friend. I was a less exciting civil servant who did the 9-5 uninteresting work nobody seemed to appreciate but I personally liked the life. My main problem was that my parents had christened me Lesley a more popular name then than now but still one that caused some to smirk as they worked out which gender it was if they had only seen my name written down then realised I was a man.
Our first sadness was in our mid twenties, Bev got pregnant and we were getting excited about the thought of being parents until one terrible day when Bev felt ill and she lost the baby. That brief sentence hardly does justice to the pain we felt. Follow up examinations made it clear that Bev's plumbing was incomplete and though now a days with test tube baby technology we could have tried again, the prospect of us getting or affording the then new procedures was not going to happen. We had to confront the fact that we would be a couple and never a family. We all take things differently, and cope in our own way. Bev decided that if she was not going to be a mum then she could follow a dream of being her own boss and within six months had set up a business which wholesaled (hopefully) salon products to shops in our area. Like I said she was good at sales, she filled the garage and the spare room with products and was soon getting orders for stuff. Money at first was tight, my wage covered the basics, just, as she ploughed all her profit back into more products. Within a year she was making a decent profit and wanting to employ someone to do the things she did not like, accounts, order picking, deliveries, mail, all the things I was doing as I could to help out but was not able to do on top of my own job, so possibly the bravest thing I ever did was to give up my secure, job for life, and risk it on working full time with Bev. Within weeks it was clear it was right, she could spend more time selling so orders increased and we got something of our free time back instead of working ever evening and weekend to catch up on what had not been done in the week.
Well after my initial fears subsided over giving up my safe job I found the freedom to work how I wanted almost as refreshing as the freedom to wear what I liked, the civil servant back then was not quite suit and bowler hat but it was still smart and grey for a bloke, I did not need to keep my hair neat and short, I could wear my flares and bell bottoms along with some shirts that were not white or mostly white, I had a full rainbow to choose from. I even bought myself a pair of platform boots, nothing like Elton John's just a half inch sole with a higher block heel, the main thing was that I could. Bev was always encouraging me to be more adventurous in my style, she had been style conscious since being a teenager but my job had limited me to the weekends when I could be more free, now with her constantly spending time with beauty and fashion people her style became ever more, well err, stylish and some of it rubbed off on me.
I looked something like this, coloured shirt possibly silk, tight trousers with enormous hems, heeled platform boots, probably a ring on my finger but no medallion round my neck usually a simple neck chain.
The business was going well, I stayed in the background pretty much, Bev did all the selling and seeing suppliers, I did the accounts, kept the stocks level and sorted out the deliveries for the courier to collect, working from home also meant I could look after the house and have the evening meal ready for Bev when she finished work. We worked hard but enjoyed ourselves while doing it.
I had worn nothing to outrageous for the times when you consider what pop groups were wearing, that was until I got dry chapped lips and as I was putting some new stock away, I was reading the labels so I knew what it was we were selling, product knowledge they call it now, I used to call it knowing what we sold. Anyway one product claimed to help dry chapped lips like mine so I decided to try a little product testing. The little box looked quite feminine as it was aimed at women, inside was a silver coloured tube which worked just like a lipstick, I had seen Bev apply her lipstick many times so found a mirror and copied her actions and spread the clear but glossy stick over my lips. It tasted just like Bev's coloured lipsticks though it did not have the ruby colour she liked to wear. My lips did feel better and after a few hours I reapplied the product to help soften up my rough lips. I was looking in the mirror thinking to myself how strange I must have looked if someone had seen me, lipstick tube in hand carefully going round my lips with it. But I was alone as usual through the day until Bev came home. It was then I was in for a shock, she gave me a usual hello kiss pressing her ruby lips against mine and I still don't know how she could tell but immediately pulled away.
'Lesley are you wearing lipstick?'
'Well yes' I went onto explain about my dry lips and the clear lipstick.
'Do you like it?'
'Well it has helped my lips.'
'No do you like it, the taste, the feel, maybe how you look?'
'How I look?'
'Well maybe not with a clear one.' she conceded.
'It is fine I suppose.'
'Just I was thinking that maybe you should try a few more of the things we sell to see how they make you feel and how they make you look, and besides I quite like taste of lipstick when I kissed you, took me back to my college days and fun I used to have with some girlfriends.'
I was getting more information than I could handle at one go. She had girlfriends, this was news to me I thought she was straight, she liked me to wear lipstick, what all the time? she thought I could try some other products, like what?
I could not marshal my thoughts so went off to organise the tea while she did her usual sorting out of her orders.
The next morning as I got dressed I found the gloss lipstick in my trouser pocket and thought if I should use it, my lips were rough still and Bev had said she would like me to wear it, so I did. Only I was so intently looking in the mirror I did not notice Bev behind me.
'That looks so sexy the way you are doing that.'
I blushed and finished up quickly, but not before she had rubbed a hand over arse letting me know she approved.
Through the day I indulged myself and just like Bev did I would reapply my lip salve and made a point of using the shaped tip to run round the edge of my lips. I quite enjoyed the process, and later enjoyed the kiss I got when Bev got home that evening.
The lipstick relieved my dry lips after a few days but I enjoyed using it and the reaction I got from Bev, so I continued to wear a glossy look on my lips even though I had no need to. This might have lead nowhere but I was surrounded by cosmetics and every now and then a new one would come in and I would read the packaging as I stacked them on the shelves. A new lipstick from the range I had used came, 'A hint of tint' it was called, intrigued I took it out and tested it on my lips. True there was barely any colour to it, the stick looked pink instead of creamy like my usual one, but I could not see it on my lips. Bev didn't notice either until she saw the tube by the mirror, praised me for being adventurous but explained that the idea was to make some women who could not wear lipstick to work feel as though they were, but then almost like an afterthought suggested I try one with real colour to it and see how that makes my lips look, something close to my natural colour she suggested. I smiled and said I would think about it.
Well I did think about it and once more intrigued by the idea of how I would look I found a colour that was close to my pink/purple lip colour, it did not stand out like Bev's ruby or red lips choices did, rather it made my lips look finished, all neat and smooth.
'Been trying the products?' was all Bev said when she saw me later.
'Yes, what do you think?'
'Suits you.'
'Thanks' and that was it, I was wearing one of three lipsticks from then on.
My next move away from straight male was when we went shopping one weekend, it was meant to be clothes for Bev but I ended up with a pair of white flares and a yellow shirt though it was more of a blouse, big full sleeves ending in tight multi buttoned cuffs, big rounded collar and frills down the front. This to me was a going out to the disco shirt but, and this was a big but, Bev suggested I might like to wear it around the house, 'like when working?' I enquired, 'why not.'
Well I went out in it a couple of times before I wore it daytime, Bev told me I looked the part amongst all those beauty products, all dressed up and looking fabulous, I pointed out the sleeves got in the way and white trousers were not terribly practical, she rebuffed me telling me she had to take care with most of her clothes and they were not ruined, why should I not take the same care about my look and clothes. Hard point to argue when she is in pale full skirted dress with big fan sleeves. The trousers were also very tight around the hips and squashed my little man flat against my body, unless I was aroused there was no manly bump to be seen which was a little disturbing until I got used to the sight of a flat front.
All this androgyny was affecting me, what with the clothes and Bev liking me to wear lipstick I was increasingly coming over as camp, not a problem so much now but back then some thugs liked to go queer bashing and I was mindful of how I looked especially when I was not at home or in a club. Which strangely did not stop me from experimenting with how I looked when at home as one might have thought dressing up was something people did when going out. My first foray into something more unusual than lipsticks that were hopefully not noticed was mascara. We had a box of samples turn up from a new supplier and in with the blushers, foundations and lipsticks were mascaras which claimed to make your lashes longer, I just had to test this out and see if my lashes could be longer. I had seen Bev expertly wave a wand over her lashes many times but to replicate the actions on my own was a challenge and I came near to poking my eye several times. Eventually I coordinated my hands and cleaned off the errors left on my skin. My eyes did look darker but longer lashes? Bev came home at her usual six o’clock, her first words were. 'Wow your eyes look great, did you have much trouble?'
'Just trying out a sample that came and yes it is not easy to do is it.'
She smiled, 'your eyes do look kind of more prominent, do you like the look?'
'Not sure, it was a lot of effort to do and I am not sure it looks that different.'
'No, what you need to do is see your lashes from side on, which is hard I know, but that is when the effect is best or if you curl the lashes. But if you don't think it makes any difference why not keep using it now you have opened the tube.'
'But you just said.'
'And you just said the effect was small, besides I rather like you with a bit of make up, kind of makes us more equal.'
That evening she gave me a few tips on using mascara and made it rather obvious that when I coated my lips in the morning she would rather like me to coat my lashes as well. I did not mind as I much spent most of my time in the office I had set up or about the house later on doing the chores, the only person to see me was the van driver who came to collect the orders I had prepared, and he never said anything nor saw anything if the way he squinted at the paper work was anything to go by.
I was rather buoyed up with the whole experimenting with sample products and next tried blusher, only a shade darker than my own skin but when I looked in the mirror could see how my cheekbones were more defined. This was not a regular product though, more something I played with when I had time, Bev was making it clear she liked me wearing make up and more flamboyant clothes. Elton John, David Bowie, T Rex and the Sweet were all over the TV and she would make comments about nice these men looked in their outlandish stage outfits, I always countered by saying it was for the stage not the street, to which she asked which street was I on regularly. Their style did change how I looked though, my favourite purchase about then were a pair of burgundy satin trousers, really tight hipsters with bell bottoms and legs so long I had to wear a platform high heel boots to stop them dragging. More significant was that I bought them for working in, so at least twice a week I could be seen walking about the house in heels and unisex trousers with a blousy shirt to compliment the look. Bev liked the choice and I liked that Bev liked it, so I wore it.
The status quo was disturbed somewhere about eighteen months after I started working with Bev, I never encouraged reps to call, that was for Bev to do, she knew what would sell I did not, so best if she saw the suppliers herself, however one day I had been playing in the sample box, this time with foundation, I had added blusher to give my face some definition and my usual lipstick colour when I heard a ring on the door bell, too early for the courier I thought, so I ignored it, but the ringer was persistent and did not seem to want to leave so I checked myself in the mirror, brushed out my lengthening hair and thought 'why not' the face looks right, the loose blousy shirt looks good and the satin trousers are unisex so why not indeed. I minced up to the front door and in what I hoped was a natural voice said 'Hi, Bev is out can I help you?'
'Oh sorry I thought we had an appointment booked for today, my name is Wayne from (I forget where), maybe I can leave these samples and call her tonight.'
I smiled and hung onto the door for support 'That should be fine, I will tell Bev when she gets back.'
'Thank you' he said ever so politely looking me up and down once more, was he eyeing me up as a possible date or trying to work out if I was a man or a woman. He turned and left for his Ford Cortina and drove away. I was still stood at the door stunned at what I had just done, it might have been the pragmatic thing to do but even if I did look vaguely female it was still reckless to expose myself to a stranger like that.
I told Bev about Wayne's visit but not about how much make up I had on at the time as I had gone straight indoors and cleaned myself up not wishing to get caught out again. But I was caught out, Wayne rang Bev and after much chat that I did not listen to as it seemed to be about products, she came into the kitchen where I was cleaning up the pots wearing a nice apron to protect my clothes. She watched me for a few minutes, 'So tell me about Wayne.'
'Nothing to tell, he came, I took the samples he left.' I was feeling very uneasy about how she was looking at me.
'Well Wayne has invited me and my lovely, pretty assistant to a product launch at a fancy hotel in the city.' A short pause for effect and to make me nervous 'Now who could that pretty assistant be?'
'Ok I was caught trying make up on.' I went on to give her the full story, at the end she just looked at me, 'I'm sorry this is so embarrassing, I shan’t do it again.'
'Oh dear my love, that was not what I was thinking, I was thinking that I would like to see my pretty assistant and work out if this Wayne was winding me up.'
I was completely unsure about what she wanted me to do but I understood enough to know she wanted me to go and put on make up again, so rather sheepishly I went upstairs and sat at the vanity table and lifted the samples from a drawer in the unit. I carefully applied the cosmetics not knowing if I should try my best and look good or make it terrible and she will not think I am pretty. In the end I went for doing it properly like I had done earlier, honesty won through.
'Lesley you look so different, you look really good you know, just one thing. How did you talk to him?'
'Like this.' I said in my girliest voice.
She smiled at me, 'So does my pretty assistant want Wayne to find out that Lesley is male or female, it seems you have a choice. If he finds out you are male it would be awkward for both of you, his being fooled and you looking so good, yet if he thinks you are female he might get randy and find out your secret anyway.'
'You could just go on your own, I think I can be sick that day.'
'Oh no that would be too easy, I think he fancies you which means he would give us better discounts, and I rather like the idea of you being my girlfriend !’
My eyebrows went up at the suggestion but after the day’s events I was feeling quite tempted to go with Bev's suggestion.
Nothing more was said about Wayne till the weekend, the product launch was for the Wednesday the following week so I rather expected Bev to be planning my new look. I tried to go shopping with her but it was clear she wanted to go alone which made me fear for what she might fetch home for me to wear. I was right to be concerned, she came home with a new 'shirt' the body was a baggy shiny satin grey fabric while the sleeves were a near transparent grey material with a silver thread flecking in it, the cuff if that is what you can call it was a thin edging loose on my wrist with a small fabric button fastened in a loop. I asked her if she had bought it from a women’s boutique, I was put down with a curt 'so what if I did?' followed by a softer 'It suits you really as a boy or a girl, I bet Bowie would wear something like that.' the mention of this fashion icon was enough for me to relax my opinion on her choice. For my part I would play with cosmetics when I had time during the day only I would leave it on to show Bev when she got home and take her criticism positively and include the points in the next day’s play.
Come the Wednesday I was terribly nervous, hardly sleeping the night before.
'Big day today' Bev said as she turned to me and kissed my naked lips.
'Are you sure this is a good idea?'
'It is a fun idea and I think we need a little fun.'
'Maybe we do but this might not be fun.'
'Don't be a wuss, you can find out what it is like to be chatted up.'
'That is what worries me.'
'No need it is all harmless, good fun and if done right gets us better prices, just flutter your lashes and flirt.'
'Flirt ! you said nothing about flirting.'
'All men like to be flattered into thinking they are special.'
'I am seeing a new side to you, you flirt with suppliers.'
'Off course, it is part of the game, means nothing, I always reckon if I can get a man to have a semi I will have the best prices.'
I did not like what I was hearing all that much. 'a semi, what are you doing putting a hand down his pants?'
'Don’t be silly, but a sexy smile, bit of cleavage, wiggle the bum when you walk, they use their imagination for the rest.'
'Glad to hear it.' I paused for breath 'and you do this to me don’t you?'
'Sometimes when I want my own way.'
'I shall be more careful in future now. One thing though I don’t have a cleavage.'
'Maybe not but we can give you a nice bust.' she must have read my face 'Leave it to me I shall make sure you are properly dressed for meeting Wayne later.' I felt my heart sink at the thought of seeing this man once more and how it could go so horribly wrong.
Well I did try to concentrate on the work I had to do, but to be honest I had to redo the accounts the following week as there were so many errors. Bev came back mid afternoon and we quickly got the orders finished and the courier on his way. It was then Bev, sitting with a coffee in her hand smiled at me with an odd twist that I could not really read but took to be I'm going to have fun and you will too if you don't argue. As I downed the last of my mug I tried not to sound too resigned to my fate as I said, 'Ok so what do I have to do first?'
'Well if we are doing this properly then Immac is first.'
And so it began, I have blonde hair and consequently my body hair is fair and I thought invisible, but seeing my arms hairless made me rethink that opinion. Next Bev sat me down after I had washed my hair, it was long for a civil servant but looked very much like a short back and sides growing out really, she trimmed a few bits but nothing much then got her small curlers out and filled my head with them. The next step was possibly the most worrying, she tidied up my eye brows, it felt like they were all coming out and I was convinced I would never be the same again if I did not have my boy brows. My relief was massive when I saw in the mirror that she had only neatened the edges and thinned them slightly. With my hair still in rollers she did her own hair and asked me to sort out something light to eat as there should be food at the event. Eating over I was sat down to have a master class in make up, I had learnt a lot from experimenting, books, magazines and the product information but to see it applied expertly was something else. I soon had the full works, foundation, blusher, dark and light shades of grey on my eyes, curled and blackened lashes which did look more effective than my usual application of mascara, a brow pencil to define my brows better then instead of my usual lipstick she choose a dark pink that looked great in the situation but I doubted I would wear again. I was beginning to feel more confident about the idea of me looking like a girl as she took out the dry curlers and brushed a curly style into place before coating it with a cans worth of lacquer. I know smelt like a woman. All I had to do was get dressed, something I could do alone or so I thought, first she produced some tight lycra pants 'We don't want any unexpected bumps showing in the wrong places do we?'I squeezed into them and for added effect tucked my dick backwards.
'Next time we should shave your panty line.' she casually remarked.
'Next time?' I stuttered.
'We might like it so why not?'
'Let's see shall we?'
She kissed me ever so softly 'Next is to give you some bumps.' She fastened the bra behind me and filled the cups with balloons full if rice, 'Now you can get dressed.'
'Well thank you.' I said a little sarcastically.
'No need to be like that.'
'Sorry.'
I pulled on my trousers and had to stare at the flat front it was just so flat I could not imagine how good it had turned out, next the shirt but it really was a blouse as it buttoned up the wrong way, the satin was cool and soft the sleeves nice but certainly not manly. I put on my new platform boots and considered myself ready.
I was looking at myself in a mirror when Bev came in wearing this outfit.
She looked fantastic, goodness knows how high the heels were but her legs looked so long and with the bare shoulders I felt quite mundane.
'You like what you see.'
'Yes you look fantastic.'
'No I meant you, checking yourself out in the mirror.'
'Well I suppose I don't look much like a man do I.'
'No like I keep telling you. You are a pretty woman. Now just a few touches.'
She undid enough buttons so if it gapped the blouse would give an admirer a glimpse of bra, a set of thin bangles on each wrist, a pearl choker, a couple of dress rings and finally a squirt of scent.
'Ready?' she asked.
'As ready as I can imagine.
'Well her is you handbag with a few essentials' she passed me a small grey clutch bag, I checked the inside contents, money, lipstick, tissues, a comb and most shocking a tampax. I picked it out.
'Why?'
'Because if you happen to open your bag and everything spills out it is more or less always in any woman's bag either a left over from the last period or just in case it comes early. Ok'
'Suppose so, I don't have to use it do I?'
'Not unless you want to know what it feels like.'
'I'll pass on that one.' and quietly put it back in.
There was a car horn peeping outside at that moment and the whole reality of what the afternoon had been building too climaxed. A taxi was waiting outside to take us to the hotel function room. This was it my first planned outing with the intention of looking like a woman, not just a over the top or camp man.
'You ready sweetheart?'
I replied in my best voice 'Now or never.' trying to sound braver than I actually was.
The nerve it took to walk out the door was at the top of my range and I only just made it, which was odd after being so blasé when I had just opened the door to a stranger a week before. Whatever my internal thoughts were I was in the back of a taxi with Bev, clutch bag on my lap, and trying to think of how this could go well rather than wrong. I considered trying to think of myself as a woman but lack the experience so fell for the idea of copying Bev and being a pastiche of how I imagine a woman might behave. I had long enough to calm myself down before the next challenge. Getting out of the taxi. This was easier, the door was opened by the hotel door man and I just stepped out without considering the actions, and so into the function room. We were given a glass of sparkling wine, not champagne, which was nice as it gave my hands something to do. Wayne soon spotted us and came over telling us how good it was we could make it and how gorgeous we looked. He explained there was a demonstration followed by a buffet with a chance to chat about the products. My nerves were just about under control as I took a seat in the demonstration area. The products were basically the same as everyone else’s except they were nicely packaged and they would have a nationwide ad campaign to promote them, though you would have thought they were the only company making cosmetics if you believed their sales staff.
'Eat small bites and don't fill your plate.' was Bev's advice on the buffet, so I picked a few small items and nibbled in between drinking more fizzy wine. I was almost relaxed enough to forget I was not a man dressed as a woman but just me with Bev, that was until Wayne turned up again, more flattery and male patronising talk about how we are his prettiest clients while clearly unable to look us in the eye preferring my open blouse or Bev's bouncing boobs. Bev would offer whispered advice like smile, laugh at his jokes even if they are not funny, look down while looking up at him, try and let him be taller than you. I would then watch what Bev was doing and copy her. After an hour of Wayne buzzing around seeing us plus several other clients he came back to us or rather me, Bev had gone off to the ladies for a break and I was alone. I did everything Bev had encouraged me to do and Wayne seemed to like being with me as he offered to get me a drink from the bar, returning with a cocktail of violent colouring and more flattering words. He had discussed the products earlier and left us to decide what we might take and this time he wanted to get an order, so in my coyest tone asked if they were his best prices, and sat so my blouse gapped hoping the lace of my bra was showing. I was only doing what Bev had suggested. He offered a few extra percent but promised to increase it if we re-ordered within a month. I told him it sounded good but I would need to check with Bev and walked over to the bar where Bev had been watching from. My shock was that he came with me and not only that, he was with me and he had a hand on the small of my back sort of guiding me through the other people there, I was not liking this contact but it got worse as we stood next to the bar and as he talked to Bev his hand remained on my waist. If that was not enough when Bev had agreed the discount she leant over and kissed his cheek, I watched and quickly realised I should copy her, so with his hand still in place he said 'been lovely meeting and doing business with you Lesley' but as I leant towards him to kiss his cheek he must have moved slightly and I kissed his lips ever so briefly. I almost froze but recovered quickly, he gave me a pleased smile before departing.
'You did fantastically, I could snog the mouth off you right now except I think it might upset some here.'
'He just kissed me.' I stammered out of my shocked mouth.
'You will get used to that, be ready next time, he is just trying it on, playing a game of sorts.'
'But I just kissed a man.'
'No a man just kissed what he thinks is a pretty woman, which is quite normal.'
'Now come on let’s get a taxi and home I want to find out if my girlfriend is as good in bed as she is with men?'
It was handy that there were taxis sat outside the hotel and we were on our way home in minutes. Bev I could tell was restraining herself, she was clearly feeling randy and not covering it up too well, I just hoped the driver did not see too much of what she was doing. Once in the house we tasted each other lipstick as the front door clicked shut. Bev was getting really turned on fondling my bust and squeezing my bum. Our outer clothes came off and as we stood there in our underwear she asked me to kiss her down below, off course I obliged and took her to our bed and lay her down. She came with my lips wrapped around her pussy lips, my arousal was still trapped in the tight pants and getting no relief.
'That was fantastic I think I could be a lesbian with you.'
'Pardon?'
'Do me again please.'
'But what about me.'
'Oh I shall think of something to repay you my pretty lover.'
I obliged her but could only feel myself getting more and more excited, I almost stopped when I felt a finger work its way inside the knickers and instead of going for my cock went for my hole, but after the initial surprise my excitement allowed her to explore my hole until she pushed a finger inside and stroked something sensitive there, I stopped licking her to catch my breath which let her know she had found a G spot. I don't know how long it took but without her touching my cock it exploded in my panties as she massaged my arse. The climax was so different to when I came inside her I just slumped on the bed spent.
'Oh Lesley I think we have found a new side to you today.'
Tired to respond I managed to say 'Pardon?'
'I think I have found myself a lesbian partner and you a whole new outlook on life.'
I had a fitful sleep caused by the memories of the previous day and woke in the morning unsure how to handle the facts of evening. Had I really come with anal sex, had I really passed as a woman, did I actually flirt with a man, had I enjoyed the experiences and the one I had the most trouble with, would I do it again?
I dressed as conservatively as my current wardrobe allowed, plain purple shirt, denim flares, adidas samba, I was about to give the lipstick a miss but Bev noticed and asked why so I told her I was having trouble with the ramifications of the evening, she just got the tube of my usual coloured lipstick, and while I let her apply the creamy product she just asked me 'did you enjoy yourself? Because I certainly did.'
'Well err I err well there were some bits, and err I am confused.'
'You enjoyed yourself that was definite, I enjoyed myself. All you have to recognise is that this is part of you and either accept it or suppress it, but I would like you to accept it.' She gave me a hug, kissed me and left for her first appointment.
That Thursday was a long day, concentrating was hard again as my mind drifted onto the questions that had troubled me when I woke and as I picked the orders I was confronted by the sight of cosmetics that I knew could make me look female again. It was like being a child in a sweet shop but told not to eat because they rot teeth, well not quite but close. Bev did not pressure me over next few days she seemed happy to let me find myself and the style which I was comfortable with. This was still quite camp even when I was trying to be a manly Lesley. After a couple of days I began to feel underdressed without my usual mascara and clear lip gloss, so they crept back into my dressing, then a ring on a finger, and a bracelet found their way onto my body and I was finding myself drawn back to where I was before the fateful night out. I felt I was just taking the camp look a little further than was maybe normal, but in fact I was looking quite female without intentionally doing so. If I had meant to do that I told myself I would have full make up, longer hair and wear a dress. As it was I was wearing trousers, a shirt that buttoned up the right way, my hair only covered my ears and collar not my shoulders and I only used minimal make up, so in my eyes anyway I was not dressing as a woman.
Right with that sorted in my head I continued getting on with work and life. The new products sold well and we were soon running low on several items so a stocking order was required, I made the list up, showed it Bev, she increased a couple that she knew where selling well in the shops, then rang Wayne. This was where my life got complicated again, Wayne wanted to call round and show us some more products, he could make Friday but Bev was committed to seeing a new customer and would not drop it for Wayne as I could easily handle Wayne, all I had to do was give him the order, look at the samples, see him on his way. Now if it had been anyone else I might well have said yes but this was Wayne a man who thought I was a woman. I could overhear Bev making the arrangements on the phone and I am miming 'NO' to her, eventually she puts the phone down after a few comments like 'Lesley will be in and have the kettle on for you when you call.' and 'she is right here and looking forward to seeing you again.' I knew she had committed me to being female on Friday and the smirk on her face told me she was enjoying the thought behind what she had just done.
Well that was the Tuesday morning, I spent the day thinking through the questions about who I was and would I do it again all over again. I looked at the make up and the blouse Bev had bought me and spent the day drifting between yes and no until she came back from her days order collecting. She was rather excited and after a nice kiss she made me promise not to be cross. I promised.
'Because, you know Kim from Kim's Kutz,' I nodded, I knew the name and had spoken a couple of times to her 'well I have made an appointment there for you, your hair is needing more than a tidy up by me, something more professional is needed.'
'And when do you think I will find the time or would like to go there?'
'I think you will go there because I have done a deal with her so you get it cheap, I would like you to get a bit of style into your hair and I think you are ready in yourself for a new style, something a little more in keeping with the new you.'
'Ok maybe but when?'
'Thursday.'
'And this would have nothing to do with Wayne coming on Friday.'
'Never crossed my mind.' she said with a fake innocent look on her face.
'You are setting me up aren’t you?'
'But you like it I know.'
'Well maybe, just as long as I don't come out looking to feminine,'
'That is up to you I only made the booking.'
I knew she was teasing me and if I was pushed would have admitted that I liked the way she was winding me up, she was clearly enjoying helping me to venture into new areas of style and I was finding it interesting to experience the new clothes and routines that were offering themselves up to me.
And so on Thursday I finished early after seeing the deliveries off in the van and made my way across town to Kim's. We had never met before and I had no idea what she was expecting of me, Bev had not given much away besides the time and how to get there. The salon was on a quiet side street just away from the high st rents, the place looked smart and fashionable with a unisex look about it, both male and female model pictures decorating the walls.
'Hi, Bev made and appointment for me.'
'Oh you must be Lesley, we have spoken.'
'I believe so, you must be Kim.'
'That's correct. Now Bev tells me you have been growing out an old style and fancy something fresh, any ideas yourself.'
'Well not really, it is still a little short, thought maybe you could have a look and suggest something.'
'Off course I can, come over here and let me take a look at what you have.' I went and sat in her chair while she moved around running her fingers through my hair. 'Nice thick hair you have must be nice being a natural blonde. Now we could feather it or go for a dramatic edge, how about an afro though that does work better with dark hair, could give you some curls though just to lift it, how about a sweeping fringe over here like this......getting popular these days, some are going back to a more lacquered style and a fringe would need control.' She went on like this for several minutes. 'What do you fancy my dear?'
'Oh I am not sure really you have come up with too many options but I don't want a mullet, I want to keep as much length as possible hopefully grow it a bit longer, but unless Bev gave you any suggestions that she thought might be good I will leave it up to you.'
This picture is about the closest I could find, mine was shorter in the neck but the flick back at the front is pretty much as it was, Kim put some curlers in and dressed it with some solutions so it would hold its shape better but I was taught how to blow dry it and lacquer it to recreate to style when I was at home. My one concern and it was a small one, was that when I did something like visit my parents I could let it be less full and swept back, but I had seen some men with similar styles, true not many but I had seen the occasional man on the TV, so in my mind that made it ok for me as a man to have that style also. But if I was being honest with myself it did make me look more like a girl than man. Kim seemed pleased with the results and how it suited my face shape, as I was offering to pay she told me that her and Bev had come to some arrangement over stock and that if I ever wanted my brows waxing or ears piercing then she would be more than happy to come to some similar arrangement. I left before she could do anything more to me, I was not sure my male ego could take much more that day.
Bev loved it when I got home saying how well it suited me, I did explain how much work would be needed in the morning if I was to do it every day suggesting I might not be blow drying every morning, this got a swift response telling me it would be a shame not to take care with my hair after all the trouble I had been to too get such a nice cut, so I put it more bluntly, 'It makes me look too feminine.'
'Well maybe........but it does suit you.....and I think you like it.......and I love it when you look less and less the civil servant you once were.'
'And what was wrong with a nice suit!'
'Just too dull and boring for my blossoming flower.'
'So I am a flower.'
'A flower that is just coming out of its bud and giving us a glimpse of the beauty that is to come.'
'Not sure I want to be a flower, they get cut and put on display and then wither.'
'Not the best metaphor then.'
A few minutes passed before anything was said, 'What will you wear tomorrow?'
'Not thought about it much.' I lied.
'Why not wear your baggy yellow top and the white trousers.'
'I could do, but I had thought of the white shirt and pin stripe trousers.' I teased.
Her eyes popped open 'No way, Wayne offered you more discount when you repeat ordered, what will happen if he sees you in male things!!’
'Only teasing, I had decided to go with the yellow as well.'
We talked some more about what might happen the day after and how I should handle various situations before we settled down to watch the news on TV and prepare for bed.
The Friday morning was more involved that I ever expected, 'good grief' I thought 'many women go through this every day' as I wet my hair and styled it before applying my full make up and getting dressed, Bev popping back in to check up on progress and how good I was looking, she reminded to wear a bra more than once and swapped my thin cotton boxers for a pair of french knickers to go over the tight panties I already had on. When she left for her appointments we air kissed and wished each other luck, I know she was hoping to get a new client but I was expecting to deceive this salesman again, and that would need luck.
I could not concentrate again and must have redone my lips ten times before the bell rang and I stood in front of the hall mirror thinking how mad I must be to go through with this, but if I don't Bev will want to know why and just bottling it was not a good answer.
I opened the door.
'Hi'
'Oh hi' as if it was a surprise to see him. 'Come in, how are you?'
'Well thank you, you look every bit as pretty as the last time we meet.' I blushed 'you would not believe how many in this business don't take an interest in how they look themselves, it is always nice to find women like you and Bev who make the most of themselves, walking adverts for their products.'
I was still blushing especially when he called me a woman. 'Come on in, would you like a tea?'
And so it went on, he took the order, I made sure we got the extra discount, he had some samples to show me, a range of nail care products which I promised to look at with Bev.
As we were drawing to a close he came out with something that shook my every fibre. 'You don't have a wedding ring on, how can anyone so nice not be married?'
I could hardly tell him I was Bev's husband, now could I! 'Not meet the right one yet.' I said trying not to sound flustered.
A few minutes later he was in his Ford and driving to his next appointment, and I was standing by the sink washing up the cups thinking 'how did I get into this situation, he is virtually chatting me up.'
Bev was home early afternoon, I tried to get her to talk about her day but she was far more interested in mine, so I showed her the nail care stuff, eventually she got out of me the comments about not being married. And for the second time that day I was shaken 'lesbians can't marry, it is against the law.'
'But...' she clamped her lips onto mine and distracted me from the thoughts that were worrying me. We ended up in bed with me on my back licking Bev's pussy while she fingered my hole. In the afterglow she whispered in my ear 'now tell me what two good looking women are doing in bed together if they are not gay.'
'But you know the truth.'
'The truth being that my partner looks female, behaves female and likes having something inside her.'
I lay there in her arms stunned by her words 'I would screw you if you let me.'
'But I don’t want you to, I love making you come like a girl.'
'But I am a fake girl, a man really.'
'And I don't care, I like you as you are.'
Even though I had just had a satisfying climax and should have felt relaxed I was feeling unsure about how I was supposed to be reacting to Bev's words, did I agree with her or should I step right back and even go back to my previous life.
The rest of the evening was spent watching the TV, nothing unusual about that except that I did it wearing a satin nightie and wrap, Bev almost dressing me in them as I got off the bed telling me how wonderful I was.
That night I learnt how much hassle cleaning off make up was but the benefit was that I would not need to change the bed like the last time I wore full make up. Saturday I expected to be able to dress a little more reserved, we had some work to do first but then Bev fancied going shopping. I was persuaded into the velvet trousers and a loose shirt, she also managed to get me to blow dry my hair, freezing it in place with a can of sample spray, along with my coloured lipstick and mascara I just knew I no longer looked camp I had become feminine.
The shopping was quite a success, Bev got a big floaty gypsy dress and I did a first, I bought my trousers from the women's section of a store, a pair of wide leg pale blue pants that were so wide they could almost be called culottes if you wanted to, and if that was not enough Bev picked up a waist coat to match them only this jacket had definite shaping to accommodate a woman's chest, to me the outfit screamed female and I knew why Bev was buying them. On the way home Bev suggested we go out to celebrate, I had dealt with my first salesman and she had got a foot in the door of a company that ran a chain of beauty parlours. I did not need to ask how she would like me to dress I was carrying it my carrier bags.
I changed into the new outfit and put a bra on to fill the top, having gone this far I followed it up with full make up, there was no way I was going to be called sir in my pale blue. We would normally go out to a club where trendy fashion people went but this time Bev booked us a table at a spanish cafe and then took me onto a disco club. We had been asked if any men were joining us at the cafe, which was embarrassing but nothing compared to the lads who kept on coming over to see if we wanted a dance, drink, company I guess even sex if they had been blunt enough. Bev turned them all down, that was until she got drunk and a couple of good looking blokes came over bought us a drink and then proceeded to lead her and then me onto the dance floor, well I was not staying on my own with a stranger and having to make small talk. They hung around till the end and I got caught have a slow dance with this bloke called Ray, he even managed to get a kiss out of me, nothing to full on like tongues but certainly lips. After that I told Bev to make her excuses we were going home, she was not as keen as me but agreed and after some farewells and promises to call them we left.
Bev was randy again and could not wait to get into bed and play with our sensitive parts, as we lay there in a 69 our fingers in each other she tickled my G spot and mused 'I wonder what sort of a cock Ray has'
'And why should you want to find out'
'I was more thinking of you and what a cock might feel like in here' she moved her fingers and made me take a deep breath 'what with you being virtually one of us now.'
'Pardon, one of us?'
'A girl silly'
'Well I think you should take at look at yourself then, your lovely clothes, your interest in make up, your nice hair, did anyone shout queer at you today, no they all took you for a miss.'
'Oh Bev please don't?'
'Please don’t what? Don't do this?' she withdrew her fingers letting them gently glide over the spot, my body reacted 'I thought not, one day I think you should lose your virginity properly just so you find out what it is like.'
'But I love you, why would I do that?'
'Because I my love am not a man and cannot fuck you properly, and every girl should be screwed at least once to find out what all the fuss is about.'
'But I am not a real woman.'
'Try telling that to Ray or even Wayne.'
'Please Bev stop teasing me.'
'OK no more teasing with words, just teasing with fingers, eh'
I came shortly after that with the strange idea that a cock might feel good in there, but it was not going to happen, these men would run a mile if they ever got near my hole.
Anyway things for me seemed to have changed after that weekend, though I never actually took a decision to change I must have unconsciously changed my mindset. Come Monday I picked out of the wardrobe the white trousers and a baggy top, I did my hair nice and added blusher to my make up routine. I even caught myself answering the phone in my girlie voice. I would ask myself why several times but every time I got the same answer, I like it, I like dressing up and if that means I look like a girl then I shall look like a girl.
By the end of the week I had lost my inhibitions and was using full make up and even wore the pale blue baggy trousers to work in. Bev predictably loved me being more girlie and got me to wear nighties to bed and sleep in a bra. Having accepted my new look I found that with the previous limits gone I could try all sorts of eye make up, working through Bev's cosmetics first then trying samples, all colours and textures giving me some horrid looks but a few really nice ones. I also discovered lipsticks that were not my natural colour and tried reds, pinks, purples even a black one. This whole process took several weeks of experimenting but I was finding colours that I liked and getting used to Bev taking me out as a woman not to mention having sex as a woman. The whole thing reinforcing not only how I looked but how I felt and how I expected people to see me.
This picture minus the long hair is pretty much how I looked on a working day at that time, casual but with plenty of feminine decoration to let anyone seeing me that I was not masculine. Over the next month I also plucked more and more of my eye brow hairs out until I had a much higher brow line and when I went back to Kim's for a trim I asked her to pierce my ears. The other more noticeable change was that I allowed my nails to grow and with a hardener painted on them got them to a length where I was having to type with a different action and had difficulty opening coke cans amongst other inconveniences, but the reason I never cut them back was because I loved how they looked when I painted them in any of the wonderful colours that were available, coordinating with my outfit whenever possible.
But possibly the biggest step I took at that time was to meet more of the sales reps who would usually meet Bev, she said her time was better spent out seeing clients and reps took up to much selling time, so I saw more and more of these people. I did not think any had seen through my new look although some had spoken to me from the first days that I had worked with Bev. Wayne was still the one I saw the most, he would call whenever he was in town even if he had nothing new to show or had no chance of an order, he just used to call and have cup of tea with me. He never failed to compliment me always liking whatever new product I was trying out that day, though occasionally suggesting a slightly different shade of polish or shadow, he was surprisingly good for a man at knowing how colours altered style.
That change happened about 18 months after I started working with Bev, our house was full of products, my life was only male for my parents, the nieghbours must thought me very weird as they had had a very nice straight bloke before and now they had one of those blokes you can't tell if they are a girl or a boy. Well they might not have been able to tell but I was in no doubt Bev saw me as a girl, she never touched my cock, encouraging me to use tape so it was held backwards all the time, this meant I had to sit like a girl to pee and at night there would be no unexpected erection waving about. We even bought a couple of vibrators, Bev being able to enjoy hers more readily than me as my sphincter muscles were a bit tight to start with until I learnt how to relax and allow intruder inside.
Over the next six months we made several big changes, we took on a storage unit and gave up our regular suburban semi detached house for an apartment closer to town. This had two big changes to me, I no longer worked at home so the housework had to be done in a more ordered fashion rather than when I fancied during the day, And I had new nieghbours who had never seen me going to work in a shirt, tie and suit. I was later to find out there was gossip about the lesbian women who had moved in and how sinful that was, but we did not notice, Bev thinking of us a couple of girls sharing. I actually had to make a big effort to visit my parents, I would leave the flat dressed down as much as possible, then park near their home and change into more male clothes before letting them see me, reversing the whole process on my return.
The storage unit had a nice little office and a counter near the door, we painted it and made it as nice as possible given that it was a basic building. The new premises opened up new sales for us as customers could now collect themselves and salesmen had somewhere more specific to call, which all meant I was being exposed to the public more and more, not just when we went out.
Wayne was still the salesman I liked the most, he was not as creepy as I first thought, it was just his nature to touch and show concern, that time he put a hand on me at the hotel was just him, I once asked him why he kissed me his answer was that it was the continental way and it was a great excuse to kiss pretty women. I dare say I blushed. But the friendship between us grew, I even looked forward to his calls and would wear something a little more feminine when he was due. Then a few things happened all together, the first was that my parents were both killed in a car accident. They had been my foundation and to have them removed was a blow that it took weeks to come to terms with. I did the funeral as butch as I could, for the sake of friends and the few family we had, but once the wake was over and I felt I would not be seeing any of them again I drifted back into my girlie style, taking ages to brush my hair, painting my nails more outrageous colours, until I was not drifting back but throwing myself into the female persona completely. Looking back I was trying to escape the grief and being someone else in a way distanced me from the reality that I parentless. A few weeks after the funeral I went mad and bought my first unambiguously female outfit, a grey maxi skirt, a pink blouse with a pussy bow, a poncho and a pair proper high heeled clogs. I was making a statement to me I suppose that this was the new me. I knew it was impractical and one of my excuses to Bev in the past had been that loose and light colours were not easy to work in, but then I felt it was worth the extra care needed to work in such clothes.
The next big thing to happen was that after a few weeks of grieving I was back at work and getting into seeing people again when Wayne called hoping for an order, or so I thought, I was wrong he had heard about my loss and had just come to see how I was, I told him that was sweet of him, a girlie phrase if ever there was one, and when he told me he was stopping in town overnight and would I like to have dinner with him that evening I was about to say no, when a voice from the stock room called out 'she would love to, take her somewhere nice and spoil her.' Amid a serious case of blushes I accepted his invite and promised to be ready for seven. Once he was gone the argument started.
'What the F are you doing setting me up like that?'
'I thought you could do with going out, doing something special'
'I could go out with you'
'But you like Wayne, he is nice enough.'
'And a man.'
'And you are a what in his eyes?'
'Well yes but......'
'And to him a single unattached female.'
'Which is why I can’t do it.'
'We once said you should try a man at least once, well here is one to try.'
'Yes but I also said it would never work.'
'And who is to say it would not work, I reckon he is gay anyway and would love to find out your secret.'
'No. Stop it. I might like being your lesbian partner but a man, no way.'
'Too late my sweet he will be calling for you at seven, now if you leave a little early you will have time to change and spruce up your face and hair.'
I was sulking I knew it, so Bev walked away then asked if I knew where something was that she could not find which got me back into working mode, so much so that when three came round and she told me in a matter of fact tone to go home and change, I did not complain, I just left. On the way home and while I was changing into my maxi skirt outfit I did rather change my view, I felt it was as far from the old Lesley, the one who had lost his parents, as I could get. To be a single woman out with a bloke was nothing like the person who was grieving. As I changed I made this into a mantra as I took extra care over my make up, curling my lashes, using eye liner and lip liner which I rarely did, glittery shadow made a rare outing as well. Bev came home and told me I looked fantastic then undid the bow I had fastened up to my neck and tied it in a loose knot about tit level and undid the buttons down to my cleavage. Within minutes the door bell called me and I was off on a date with a man.
He took me out for a lovely meal and treated me like I was someone special. He was attentive and kind, kept me entertained and whenever he had the opportunity made me like a woman. I had to admit it, I loved the attention, it really took me out of myself and for a few hours the misery lifted. My concern earlier was that he might find out my secret, well he was such a gentleman that besides small touches to guide me to a table say, or a greeting kiss he kept his intentions (if he had any) to himself. He took me home and after a kiss to say thank you we parted.
I walked in to find Bev still up. 'Successful?'
'It was ok.'
'Well take that grin of your face if it was only ok, because that face is one of a girl who has had a good night.'
'Ok it was good.'
'Thought so and when is he around next?'
'What?'
'Well surely he is taking you out again when he is in town next'
'What makes you think that?'
'It is how men work and I bet you know as well.'
I got defensive 'I do but only because it is in the diary at work.'
'Good enough for me I think. And you will be going wont you?'
'Why?'
'Because you enjoyed yourself.'
'I am going to make a coffee, do you want one?' I did not want to admit to myself or to Bev how much I had enjoyed being dated, it felt disloyal to Bev and just a little odd to me.
The other big turning point was that one day Bev came back from her travels around the beauty shops with a small container and with a big flourish produced them.
'I think you will like these'
'What are they?'
'Female hormone tablets'
'What, why, how?'
'I got them from a friend who gets them for girls who don't want to get pregnant but can't go to their doctor, so that is how and what, the why is because I think you would look great with some real breasts and these should help you grow them.'
'But their will be side effects.'
'Here read the notes and decide for yourself, I only got them to see if they might be liked.'
I calmed down and promised to read up about them.
I also found myself looking forward to Wayne's next visit, Bev would be out so I would be able to make my own mind up and not have her pushing me into something I might not want to do, though to be fair I had enjoyed what she had pushed me into last time. The diary page told me that Wayne would be there on the Thursday, so for no expressed reason I washed my hair on Wednesday and gave myself a manicure and a full body shave. Bev was up and gone early so I was able to pamper myself some more with more expensive make up and spending time choosing what to wear. The pussy bow, baggy trousers and clogs won for work, but what to wear if he asked me out again?
He turned up on time, was as flattering as ever, did the french thing of kissing both cheeks. He just made me feel special. We did the business of what we needed before he rather awkwardly asked if I would like to go out for dinner again, maybe he was not sure if he was getting too familiar with a client or was having a fit of shyness himself, but when I accepted he relaxed and thanked me.
I was home for five, Bev turning up just after, and finding me in bra and knickers knew without asking what I was doing, she knew Wayne had been to visit earlier. I wore the pale blue outfit, Bev gave me a sisterly hug when the bell rang and told me to be careful. I told her I had no choice. The evening was every bit as enjoyable as the last only this time as we sat in a pub having a pre dinner drink we sat a little closer so we could speak more easily, but I did find the contact rather nice and when he took my hand to lead me outside and to the restaurant I felt I was being accepted as a woman and revelled in the experience. I was leaving the old me behind.
Going out with Wayne became a regular thing, he was in town every fortnight and we would go out for dinner. I got used to holding hands and kissing after another date. Which prompted me to look out the pills Bev had got a few weeks before and consider if I was enjoying being a girl so much, why not take the hormones and make my body conform to how I felt. With my morning coffee I swallowed my first and considered that I had indeed crossed a line into a female world at that moment. The tablets took time to have any effect, but I did notice my erections were weaker but my orgasms did not fade in strength, my nipples also started to tingle and get darker which Bev loved to see and nibble on when we made love.
So two months after my parents died I had started taking hormones, going on regular dates with a man and living full time as a woman. Though it was probably something to do with escaping my grief I would say that I enjoyed the new horizons the situation was creating. It was on the forth date with Wayne that we were eating in a country pub, side by side and able to talk more intimately than across a table. He starts to tell me how much he likes me and thinks I am really nice and how he would love to see more of me. I tried to counter this by flippantly saying that me and Bev had him down as gay, he blushed at that I had clearly hit a sensitive spot, but when he recovered he somehow managed to say how he knew I had a secret as well, my turn to blush. Over the next half hour he admitted to preferring men but how he found me attractive in spite of my clearly pretty looks, and very gently he let me know that ever since the first time he saw me he had been suspicious of my true gender and wanted to get to know me better if only to find out the truth. I was shocked that I had been rumbled, but he held onto my hand and calmed me down telling me he had to look very hard to spot the clues and it had been months before he was sure. I ended up telling him about my whole story, right up to the hormones. It was late when I got back to the flat, Bev was in bed asleep. So I slowly got ready for bed and made myself a drink to relax with, all the time thinking about how I had opened up so easily to Wayne and wishing I could tell Bev but did not want to wake her then wishing I was still with Wayne snuggled up in his arms like Bev used to do in mine when I more of a man.
Come the morning I was groggy but Bev just wanted to know where I had been to be out so late and clearly implying that I might have been doing way more with my date than having a meal. In the end I told her everything to shut her up, even how we had held hands, kissed and enjoyed a cuddle together. She was a little shocked by my disloyalty but she had encouraged me, so that seemed unfair. Soon she was off to see clients and I was off to the warehouse where I found Wayne waiting before he left for his first call of the day. A bunch of flowers and a promise to be back as soon as possible was all he had time for. I promised to call him when he got home. And that it seemed was the start of a more serious friendship. We spoke a couple of times a week and every other week we had an evening together. Then he arranged to make us his last call on Friday so he could take me away for a weekend in the country, well York to be more accurate. I agreed and Bev did not object, saying that I might get over the teenage crush stage and find out what men are really like, a bit unfair I thought as I was still technically one.
Anyway I packed enough for a week and was waiting for him having done all I could in the office before I left, Bev gave me a hug, she said as a friend and told me to make the most of the opportunity, a quick wave and I was driven away from my familiar surroundings and onto the busy roads out of our town. We arrived late and had a quick meal before booking into our hotel, Wayne signed us as Mr and Mrs W Smith which felt so risky at the time, and for us well beyond not just being unmarried. Wayne ever careful had made sure I was ok with a twin or double room before he booked, I had said either but was still a little surprised to see a double when we opened the door.
'I suppose you thought a married couple would prefer a double?'
'I did, any objections Mrs Smith?'
'Not at the moment but if I find anything to object about be sure you will hear them.’
'Best make sure my wife has a good time then.' As the door closed behind us he gave me a kiss unlike he had done before, full of passion and desire.
'I think I should be getting ready for bed'
'If you want.' I think he took it as a rebuttal to his advances, but I did need to clean my make up off, get out of my trouser suit and into the new short nightie I had bought for the occasion. En suites were just coming in and Wayne had booked a room with one, so I disappeared to reappear some while later in a pink baby doll nightie with pink frilly knickers just showing below the hem.
I hung from the door frame 'Worth the wait?'
He was already in bed and just pulled the sheets down on my side 'I still can't believe how good looking you are.'
'Well my dear you must understand I have never done anything like this before and you are the first man I have ever slept with.'
'I understand how you must feel, I felt the same a few years ago when lost my cherry'
We talked for a bit about how he had found out he was gay and some of his experiences, all the time we were tenderly touching each other until I allowed him to kiss me again. This time he was naked and I could feel his cock against my thighs. Fascinated I took it in my fingers, I had only ever held my own and his felt so strange, a dribble of pre cum got onto my fingers so I licked them to find out what it tasted of, Bev was never keen on sucking me, said it was not a nice taste but I found it salty and nice. Wayne asked if I wanted some more and pulled the covers back to reveal his manhood standing to attention. I gave it a few licks and smiled as it twitched on my lips.
'Have you ever swallowed?' I asked.
'Sometimes'
'Has anyone ever screwed you?'
'Yes.'
'What was it like?'
'Hard to say. Do you want to find out?'
'Not sure. What would you like to do?' I said passing the lead back to him.
'Well if you want to, I would love to be the first person to make love to you as a woman, to fill your hole and hopefully make you come in a way that only anal can do, but only if you want to.'
I kissed him with his cum still on my lips. I was preparing myself for what I had been telling myself I wanted to try. In the end I rolled onto my back and raised my legs like a woman might and invited him to lie between them. I was so glad I had been using the vibrator because feeling him pushing his cock against my arse and me relaxing enough to allow him in took an effort, I screamed into his neck as he penetrated me, but then as the KY jelly worked he pumped in and out, going deeper each time until he touched the spot Bev had played with, I arched my back and squeezed his buttocks trying to push him further in. I lay there aware that he was on top and riding me, but I was lost in the pain and pleasure until my senses exploded and I could do nothing but pant and hold him tight. I believe he came himself sometime during my time beneath him but I was not sure when, my own climax overriding any other feelings.
He lay on top, our sweaty bodies exhausted. 'So how did that feel?' he whispered in my ear.
'The best ever. Is it always like that?'
'You should know you must have had sex before.'
'Well yes but not like that.'
'All I can suggest is we try again so you can find out the answer.'
'Not now though Mr Smith, Mrs Smith needs a rest.'
That was the first time I made love to a man and was the first time I slept cuddled up with a man and I loved that feeling of being his woman, being protected by him as he held me in his arms.
The Saturday was a day of sightseeing and going to pubs for lunch and dinner interspersed with looking round some nice shops. I remember he bought me some nice long ear rings that tickled my neck. But the main event was the evening. We were in our room early and making love before I normally have supper, but I wanted to feel him inside me again and to relive the fantastic moment when I came once more. He did not disappoint, gently and tenderly relaxing me before easing his way inside, finally working his cock on my spot until I was asking him to push harder. I had never felt like this with Bev, I had been the cock and just banged away hoping she got there before I could hold out no longer and wilted after my sudden burst. We recovered a little and made a cup of tea (no mini bar) and sat there near naked, Wayne stroked my inner thigh and made me jump it was so sensitive.
'You know what is so good about this...........I get to look straight while I know I am going with the best looking bloke I have ever known.'
'And for me I get to have a bloke who rather likes my non female anatomy, so that is about perfect.' And with that the cups were set aside and bed gymnastics resumed.
Well that was Saturday. Sunday was a return to reality, a lovely drive home and back to Bev. I had become more and more swept up in the novelty of being taken for a woman by a man eventually taking it to the ultimate intimacy. But that drive home my bubble burst as the unfaithfulness of what I had done dawned on me. I often looked across at Wayne and thought of what ifs, and then looked at my female decorations like long pink nails, high heel shoes, and tight clad legs thinking 'how did I end up in this situation?' Wayne only carried my case to the door and gave me a quick kiss as he thanked me for a wonderful weekend, I had said a few things which had made it clear I was having trouble reconciling myself with my actions and how Bev might react when I got back. I crept in trying not to be annoying.
'So how was York?'
'Lovely, some nice shops and parks'
'And Wayne?' gosh that was direct.
'Fine.'
'Did he make you feel like a woman, treat you like a woman?'
'He was very nice to me.'
'But did you let him?'
It was then the tears started 'I am so sorry I do love you Bev, but I am so confused, I did let him in me, I wanted to have him in me. But why did I want to when I have you, why do I want to dress like this, I enjoy so much and feel that I am a woman most of the time now but I am a man, why do I prefer heels and I am sorry Bev a real cock is better than a dildo.'
She got up and hugged me as I stood there tears streaking my cheeks with black. We ended up on a settee Bev's arms around me with my head on her chest, I don't know what was going on in my head really, the grief, the disloyalty, the guilt were all there, but Bev just held me and let it all pour out. She was a good friend that night, I told her about my parents and how important they were to me, I realised how I had been hiding from the pain, I also told her how good Wayne was to me, how it was nice to be taken for a woman and ultimately have sex in the woman’s place. She sat with me listening as all this and more came out. Eventually we went to bed and cuddled until we slept.
The next day was work, I hoped for no public customers and few phone calls and that is what I got meaning a day buried in a desk lost in paperwork, ok I had moments of distraction but I was using the work as a sanctuary. I meet Bev at home later, a meal on the table for her, she kissed my cheek before handing me a carrier bag, I took a look inside, 'for me?'
'Yes for you.'
It was like a short monks habit, Bev then looked me in the eyes 'For you next date with Wayne.'
The tears started again as I told her I was wrong to have gone with him, that I was stopping with her. Then as the meal got cold she told me I should go with Wayne or another man if a nice one comes along, as a man she knew I was straight but as a woman I liked men, she had set me up and encouraged me to be more and more feminine until I preferred looking like a woman and thinking of myself as female, it was she who had encouraged Wayne from the start at first to see my reaction but later to allow me to experience a woman's role with a man. I had to go and dry my eyes and clean up the streaks on my cheeks once more before putting the cold food into the oven to warm through. She finished by telling me that she loved me but not in the way she had when we married, more in the way you might love a child and when it grows up you have to let it go, I had grown into a lovely woman but I was not totally lesbian so I needed to find my own self.
Maybe Bev regretted encouraging me to wear that lip gloss, the girl’s trousers, though she never openly said so. The next time Wayne was in town she made a point of seeing him and asking when he was taking me on a dirty weekend again, that was only ten days after my first weekend and a few days later I was in his car being driven to another part of the country in my new dress with mixed emotions about who I was and why I was there. He listened and seemed to understand, his discovery of being gay had some parallels. Friday night he just held me close, but by Saturday night I just wanted to feel this man inside me and make me feel like his woman, he did not disappoint.
Well after that weekend I found it hard sharing a bed with Bev, and in a single bedroom flat there was nowhere to go, so when a small flat came vacant I rented it and moved in, Wayne offering to pay some of the costs if he could stop when in town, off course he could. Me and Bev managed to stay good friends and make the business work. She started being more open about being gay and would date women once I had been away for a while. I got to see Wayne more as he would stop weekends and midweek whenever he was close until he gave up his place near his office and we got a larger place between us, this meant his travelling a little more but I got to be his wife as I changed my surname to his by deed poll and avoided the Mr bit.
Now forty years on I wear sensible mature clothes, stopped the hormones when I found out how dangerous they could be, had breast implants but retained my dick because Wayne liked me to have it. The business did fine as we got the best rates of one company in particular, selling up and retiring after 30 years of selling to become fulltime housewives, Bev found a rather butch dyke who loved her and loved being the breadwinner it seemed so we ended up being ladies who lunch while our partners worked to pay for it. Perfect.
It was Saturday midday, we had been cleaning the house and shopping for groceries, and now it was time for a break, some lunch and read a paper.
As we ate Emma looked at me and laughed, ‘Only just realized we are dressed identically again, jeans, trainers, brown fleece top, both got pony tails.’
She was still giggling when I said ‘so what? I just picked what was to hand.’
Then she went odd on me, she started to wonder what else we wore that was sexually neutral. I had many t shirts which she did borrow, we both had white shirts, but called hers a blouse, we both had regular trousers, and unfitted jackets. When we discussed this we realized how little we had that was gender specific, Emma had a few skirts, dresses and heels, I had work suits and ties which rarely got worn nowadays.
Soon the discussion had lead us into the bedroom and we were looking through our wardrobes commenting on the contents, it was as I pulled a brown cotton blouse out and was agreeing how it was quite androgynous, that Emma sprang up, ‘How about we pick our clothes from the wrong wardrobe, we are about the same size so they should fit?’ she smiled at me ‘See if the brown fits?’
I was a bit off guard by her comments, but she has a lovely smile and I pulled my fleece off and the t shirt it was hiding. The first thing I noticed was how soft her cotton shirt was, then how the buttons were on the wrong side. ‘Now my turn’ and she picked out one of my loose cable knit jumpers, ‘I always liked this one, will keep me warm I bet’ then she took her jeans off and picked out a pair of my chinos. ‘Your turn’ she pointedly said to me.
I was perplexed, ‘I’m not sure, the shirt is nice but why trousers?’
‘Just for fun, come on, let’s see you in my cream ones with the turn ups’
They were a bit snug on the hips and loose around the waist, well bit of a low waist more like hips, so I clipped the belt to fit my waist, but the length was about right, and to be honest did feel quite different to my usual trousers, they were made of a new material for me and did not have the stiffness of my usual clothes. She enquired how they felt, and I told her how different they were. Then she picked up my black shoes and slipped them on and tied the laces.
‘Oh I don’t think shoes are so easy to swap’ but she went into her shoes and passed me a pair of brown ankle boots with nearly no heel, ‘There you go, be perfect’ and they were, I zipped up the sides and instantly recognized how much you could feel through the soles, they were so supple and thin.
‘One last thing’ she was smiling again ‘you pick one of your necklace/chains for me, and I will pick one of mine for you. Deal?’
I passed her a leather lace with a stone cross on the loop, she passed me a fine chain with a green pendant hanging of it. ‘Whoa, that is not neutral’ ‘Who said it was, but I wear it with that blouse, so here you go it will look fine’
Next she suggested we release our hair from the tails and brush it out, then standing next to one another before the mirror we had to admit we did look a bit in the wrong clothes but not much, Emma looked a little stockier with my clothes, whereas I looked a bit camp, without the pendant I doubt I would have noticed.
We spent the rest of the day dressed that way, Emma went out for a few things she forgot earlier, I pottered about the house venturing out to the bins with rubbish and was sure I was conspicuous in my nice soft clothes. Then as I was preparing the evening meal Emma came out with another of her daft ideas. We go out later dressed as we are. I reacted quickly with a no, but she was not put off asking me if I liked the feel, if I liked the way they hung, if they felt nice, finishing with ‘Seeing as it was a yes to all those questions, then we might as well go out and enjoy them outside.’ We decided on a pub in the centre of town we had never been to but had heard about because of the attraction it had for alternative ways of dressing, which when I considered it, was exactly what we were doing.
Off course I had to borrow one of Emma’s jackets, a nice short brown one cut like a jeans jacket, Emma took my suede jacket. My first problem was a lack of pockets, and having nowhere for my wallet or keys, Emma laughed and told me how great the trouser pockets were, then offered me a shoulder bag, to which I just said ‘What the heck, in for a penny, in for a pound’
The evening was a real eye opener, I only thought people dressed in such outlandish ways for TV programs, but here on these few streets it seemed you could dress and be whatever you wanted to be. We talked about what we had seen all the way home, and how we had not once felt odd, if anything we felt a little understated.
Sunday is usually a lie in, then visit relatives, or go for a walk, maybe pub lunch and relax. Emma decided she fancied a pub lunch out in the country, and went to my wardrobe to select her clothes. I watched as she picked out a fashion shirt, jeans and my cowboy dealer boots then went to my drawers and selected boxers and a plain cotton t shirt I wore as a vest.
‘I suppose this means I am going to get dressed in your stuff’
‘Yes it does dear, and you know you will love it’ she said as she climbed on the bed to give me a kiss.
I went to get the things I had worn the day before, ‘Boring’ Emma shouted ‘be adventurous, try something different, like this’ she pulled out a white silk blouse. ‘Not very neutral’ I objected ‘Try it on, you will love it’ it was made with what I call a proper collar and it was wonderful to touch as it slid up my arms and over my shoulders, my smile gave me away ‘Told you so’ Emma crowed. Next she handed me a pair of control pants, which held everything flat at the front, then her leather trousers, I had nothing like these and honestly had only seen a few men wearing such things. They were very tight but did look right. She was now dressed and with her hair brushed behind her ears, made me think she looked handsome more than pretty. ‘I normally wear these heels with those trousers, don’t suppose you would like them?’ I gave her an incredulous look ‘But I am in your heels, why not you in mine’ I countered with ‘they are higher and narrower to start with’ this meant she found a block heel that was lower and gave me one of her smiles. I tried them on and true they were not much different to my cowboys, just far less chunky and far daintier.
In the bathroom I brushed my hair and not for the first time felt that a beard might have helped with a masculine image, even the faint shadow of a few days growth would at times have been welcome. Today though, it just felt as though a dark chin would look wrong. I brushed my hair into a side parting so the fringe came across my face, Emma would like that I told myself and went out to show her the dressed me.
‘Fantastic, do you like it?’
‘I feel more of a girl than you do, if you want to know’
‘Well in that case, why don’t I help you along?’
Before I could really object, she had me washing my hair so she could blow dry it into a style she liked, which was pretty much as before, just with a few flicks and hair spray to hold the fringe in place. Then she added some colour to my checks, mascara to my eyes and lip gloss over my pink coloured lips. Finally she squirted scent on me. ‘Was that necessary?’ ‘No, but it makes you smell nice. Now I think you should wear this’ she slid her wedding and engagement rings off and took my chunky gold band for herself.
‘This is so much fun, for today you can be me and I will be you. Now come along Emma lets get moving’ this was all happening a bit quickly, we had gone from swapping clothes to swapping genders in a couple of days, but it was fun and very nice fun at that, I just picked up the shoulder bag, stuck my hands out in a camp fashion and in a falsetto voice said ‘Coming dear’
Outside was a shock when I thought of all the people who might see us drive away, but no one was out on their fronts, so I could breathe again. Emma, the real one, it seemed had changed where she wanted to go, we were heading into town not out to the country pub we usually did, which was a relief when I thought about how I was dressed and the many opportunities to be embarrassed.
We ate in a place near where we had gone the night before, there were a few unusual fashions around, but not like the evening, but we had a good time watching the passers by and commenting on how they looked, or trying to guess what comments they might be making about us from the looks we occasionally got. The meal over Emma decided she would like to take a walk around the city, something we never did. So we left the safe streets of the gay village and walked past grand Victorian buildings and into the back streets quiet for the weekend, then into the shopping streets and onto the cathedral, it was fascinating for many reasons, we had not really been in town for anything other than business, the clothes were making us feel self conscious, and for me the constant worry someone was going to say ‘That’s a man’ in a loud voice, had me on full alert.
That nobody commented, that no one seemed to care, meant that after an hour of wandering we stopped for a coffee and watched the world pass by without thinking we were being scrutinized by every pair of eyes. And then there was the sensations for me of new fabrics against my skin, the silk was wonderfully luxurious, Emma even caught me stroking it as we sat in the café, ‘You liking this?’ she asked.
‘Are you?’ I countered
‘Love the comfort of these clothes and the room in them, and pockets, also have you noticed the waiter gave me the bill, this is great fun, an eye opener for me. And you?’
‘I can’t believe you prefer my clothes, this silk is lovely, the trousers are a bit tight, but feel great. And yes I did notice him, was nice not to be in charge and let you be seen as the ‘boss’ for a change’
With that she got up and went to pay. As we made our way back to the car I could not help looking in the fashion shops and imagining myself trying on some of the outfits on show, even Emma slowed at a window of men’s clothes and asked if I had ever thought of getting a collarless jacket. Maybe she was having ideas of wearing my stuff more often.
With work the next day, we went home and had a quiet evening, but I had a few things to learn, Emma was enjoying her male dominant role, and to some extent I played the submissive female role to please her and join in the fun. She would assume I would make supper and fetch drinks when she was watching something on the TV, and say things like ‘Thank you darling’ in a patronizing way. But it was all done in fun and we enjoyed ourselves. I also learnt that before bed comes cleansing or else the pillow gets the make up and my morning face would need more than a quick rinse. We both learnt that having fun through the day, leads to fun in bed as the energy of the day followed us until we collapsed and slept.
Come the morning it was back to normal, both dressed for work in regular work clothes, had breakfast and left for work. I must admit to having a few daydreams about the weekend and reliving moments that had been the most fun. But Emma had clearly had a different experience, when I got home she had changed from her bank teller uniform into one of my sweaters and a pair of jeans, she would often change when she got home, but to go for my clothes was a clear sign the weekend had made its mark. I normally only change if going out in the evening, and as I was stopping in I remained in my work clothes, nothing unusual for me at all.
I did not remark on Emma’s choice of evening wear, but every night she would change into something of mine, so by Thursday I casually asked how she was feeling about things. It was obvious she had got a real buzz from her masculine identity and explained how the bank’s skirt suit was just so uncomfortable she was glad to get home and change. I always thought the suits though pedestrian were quite nice and comfortable, clearly I was wrong.
Come the weekend Emma got up early and picked out my jeans and a fleece top, then set about some breakfast which she brought back to me in bed. ‘This should be your job you know’, ‘why?’ I asked because I fancy being Paul again and calling you Emma. Now to say the idea had not crossed my mind would have been a lie, and I had been lying in bed considering what I could try on this time, but here was Emma being very positive about how she wanted the situation to develop.
‘And you think I will do whatever you suggest’
‘Off course you will seeing as how I am the man of the house, come on swap rings and get dressed in something soft and sensual, you know you want to!’ she took my hand and took my ring off and without complaint from me, replaced it with hers. Then looking me in the eye, ‘Right now that is done, I will get of to the shops, while you make a start on the cleaning’ and with a kiss she was gone.
I got up and showered, then dried my hair brushing it out to create more volume, then styling it something like it had been the Sunday before, next the wardrobe, she had some satin cargo pants I fancied trying on, and with a loose angora sweater I felt quite feminine. Next I played with mascara and lipstick before looking at shoes and thinking ‘Maybe I could try something proper girlie’ I settled on flat sandals that had beads along the strings which ran over my feet and toes. Finally I looked in the mirror and had to accept the image I saw was not that of a man, rather a man dressed in women’s clothes but not quite getting the woman bit right. I reckoned the point was not to be a woman, just to wear women’s stuff and that is what I was certainly doing, not a stitch of my own clothes was on me, and truthfully I felt great in the satin and soft wool, and if it pleased her I would happily run around and play her dutiful wife.
I had only just finished getting dressed when the boss got back. I flounced out to meet her and give her a kiss, made her a drink before getting on with the cleaning. The reaction I got from her about how I looked was very encouraging, especially as she squeezed my bum through the satin, the control pants in a thong style made this very pleasing to me also.
We had another trip into the gay village for more people watching, and being comfortable dressed in what we felt was unconventional. Emma wore a tie for the first time, and I had changed for the evening into a pair of long loose black trousers with a tunic style top that was more like a short dress, she redid my make up and I could instantly see how she had got far more definition into my face with the colours, but my main step out of masculinity that night was to wear a pair of 2" court shoes, the heel was a block type so they were not hard to walk in, but they were definitely a ladies shoe, and I most certainly had gone along way from the neutral look we had started with.
On this visit we were more relaxed and able to chat with other people out for the evening, it is a surprisingly friendly place, and the alcohol helps, and so we chatted to various people of various life styles, we got on really well with a couple of transvestites who were OTT with the towering platform heels, micro skirts and enormous chests, but they were enjoying themselves, Emma got chatted up by a group of lesbians when she went to the bar, nothing happened that seemed wrong or deviant and we felt more at ease with these people than we might do at the squash club or having a drink at the local. As we left we agreed we would be back whenever possible. But not till the next weekend at least, family duties beckoned for our Sunday.
But visiting family did not stop Emma, she wore my boxers and the cable sweater, and as I thought about it I came up with silky knickers and her brown cashmere sweater. All very neutral and quite acceptable we thought, but my mother recognized how we had swapped tops and questioned us about it. Emma calmly explained how we were experimenting with clothes and as we often dress alike then why not use each others clothes to dress in, my mother found the whole idea amusing and confided that she often wore my father’s clothes for gardening, and if it was cold outside she would wear his warm clothes. Maybe it is genetic we laughed then changed the subject.
The weekend’s experiences did have an effect on me during the week, at first I just got up and dressed for work, but in idle moments I would find myself considering what I could wear for a change, or what I might like to try at the weekend if Emma wanted to swap rings again. By the time Friday had come around I was wearing knickers and a plain grey sweater of Emma’s to work. I was also noticing what people in the office wore, the women seemed to be smart in general, but the men had no dress code of suit and tie though one or two women dressed quite casually there was a majority of men who dressed casually almost to the point of not caring with terrible colour combinations and well worn clothes that might be fashion but don’t look good to me. So I felt my grey top would be in keeping with office style. During the evenings I spent time on the internet finding out about styles, fashion and make up, mainly wondering what might suit me, a bit of how I could make the cosmetics work better, and also how to style hair which I decided was going to be this weekend’s challenge.
On the Saturday morning I waited until Emma had gone out shopping, in my clothes off course, then showered and conditioned my hair before setting about the task of styling. I had Emma’s curling tongues and blow drier as well as setting lotion. It was not a quick process, but by the time I had finished I had it curling under at the back and flicking out at the sides with a fringe sweeping across my face then joining the side flick. A bit of a Dallas look really but I felt not bad for a first try. Then I dressed in a blouse, not wanting to disturb my hair and jeans before starting on the cleaning.
Emma loved what I had done to my hair and teased that I should try perms or dyes next time. Once I had finished the housework I had time to play with cosmetics and as Emma did not use that much make up I had forced myself to go and buy my own hoping it would not look to obvious I was buying for myself. I spread the foundation, then blusher on my face before dusting it. Next I applied a light bronze to my eyelids, then a fine line along the top lid finishing the eyes with lash lengthening mascara. Last I outlined my lips with a pink pencil, to stop it bleeding the notes told me, then filled with what I hoped would be a nice but not in your face creamy pink which promised not to wear off till the night was over. Then I slipped into the white silk blouse and the baggy soft black trousers, finishing off with a pair of Emma’s kitten heels, thinking the narrow heel would be odd at first but not as odd as a higher narrow heel might feel.
To say Emma was impressed would be an understatement; she loved my look and called me pretty. As expected we had a night visiting bars in our favourite part of the city, again we had lots of watching to do as well as chatting with fellow customers, Emma proudly boasted that she had been flirting with some girls, so when we went in a bar with a dance floor and a man asked me for a dance I accepted and wiggled my ass to the music, Emma watched with a grin on her face, and he gave me a long kiss as I parted from my partner. On our way home we discussed the evening and events. I stuck with the ‘I am enjoying the clothes’ but something was stirring in me that said I liked being feminine, flattered and to some extent submissive, at the weekend I would do whatever Emma as the man asked me to do and I did not mind at all. Emma expressed how much fun it was to be thought of as the boss, and have pretty girls chat to her thinking she was gay also. We ended with a passionate bedtime romp, confirming to each other that this life style suited us in more ways than one and we were going to see just where it took us.
Sunday we went for a hike, but as we had not exchanged rings I wore the pink jacket, Emma took my walking gear. Then once home it was a good shower to remove the girlie traces from my hair and face ready for a day in the office.
Weekdays became more neutral as I wore more of Emma’s less feminine tops; I even bought myself some knickers that while being soft still had enough room for my boy bits. I also continued my internet searching looking at hair styles and make up choices, Emma had made a few suggestions on the Sunday gently so as not to hurt my confidence. I did question myself why I was doing a feminine face when I was generally doing this cross dressing so I could wear neutral clothes that felt great on me. In the end I came to the conclusion that I would wear make up because it pleased Emma, I liked the way it made me look, I was enjoying finding out about these things, and especially when I was out at the weekend to wear what is clearly a woman’s outfit would look odd with a man’s head on top. With make up and hair I would look and feel more complete in the image I was portraying, and so enjoy the clothes more openly. With that sorted I planned on going for as good as I could without doing something I could not return from on the Monday.
Friday evening was spent shopping and planning what I would do on the Saturday, so come the morning I was ready and did not spend time in bed thinking what to do. I was showered and in a robe before breakfast and was conditioning my hair as Emma left for the shops. This time I used the tongues to create a head full of curls and used clips to hold the fringe to the side after brushing it to get some of the tighter curls to relax and fall better. Then I did my face, foundation, blusher, liner (top and bottom) mascara and lips (this time a darker burgundy). The hair was less fixed so I choose a plum roll neck top with the satin cargo pants, finally deciding that I should have a go in proper heels and picked a pair of 3" wedge sandals. I was ready before the boss returned this time and had made some way through the housework when she came home. Once again she loved what I had done, and approved of my ideas for what to do with my eyes when we went out that evening, which was to go for a smoky effect on the lids and keeping the same lipstick but using a little more blusher to define the cheek bones.
We had the house all sorted by early afternoon, and Emma asked if I fancied going out, she wanted to go to the shops but I was tired and preferred to rest so she went alone, after making it clear she was happy to take me anywhere dressed in my non conformist way. I just thanked her for the compliment and said ‘see you later Paul’ emphasizing the Paul. At five o’clock she appeared and shocked me with what she had done, her pony tail was gone, her ears were now visible with hair feathering down in front of the ears and down to her collar and above her eyes. It still could look feminine but with her wearing a shirt and jeans the hair was struggling not be masculine. ‘Do you like it?’ she asked
‘Might take some getting used to, but yes, is it what you wanted?’
‘I hoped for shaper edges, but the stylist did not seem to hear me when I said short back and sides like a man. So I got it like a woman, maybe next time I will try a barber’ and laughed ‘Anyway if you can be different and go for a head of curls I reckoned I could match you with this, any complaints?’
‘Most certainly not, it suits you’
‘Now then my pretty wife, how about I take a rest while you make me something to eat, then we can get ready for going out this evening and see how pretty your latest ideas are’
I just said ‘Yes dear’ and jumped to the task without a thought that in the past Emma would have cooked at the weekend, but the roles as well as the clothes were getting reversed, and I was not objecting at all and my partner seemed to embrace the change more than me, so while I wore the diamond engagement ring my role would be that of the wife, which was fine with me.
It took me ages to get the smoky eyes I was hoping for, and then when I removed the roll neck my hair got messed up and I had to spend time brushing and styling it again. But eventually I dressed in the baggy black trousers I liked and a new top I had found among Emma’s stuff, it was a pink chemise (a vest to me) with a sheer sparkly kaftan to go over the vest, meaning the outline of the chemise was clearly visible. I had seen such things before and had always thought them attractive in an understated sexy way, which suited the style I liked. Emma approved of my choice saying she had bought it but then felt over dressed in it, so it had stayed unworn for a year or so, but on me she said it was perfect. Then before we left I dabbed scent onto my neck and wrists hopefully to help the illusion the clothes was giving.
We had another great night out, we were meeting people we had meet before and were feeling more a part of the community that lives in that area. I loved the big bell sleeves and the floaty body of the top. The bosses new hair was a hit with her lesbian friends and as she spent time chatting with them I chatted with another cross dresser I had meet before who suggested a club that encourages TVs to go, I said we would check it out later. I was unsure if I should be offended at being seen as a TV, I still saw myself as a man who cross dresses. We did go to the club and enjoyed the sight of not being the only cross dresser but I was among many men who could not hide their build very well, and then there were the ones who dressed OTT and looked stunning in a pantomime way, but there was also one or two who left you thinking are they male or female, because if they are male they are excellent looking women. And something inside me said I wanted to be that person that is totally convincing, being mistaken for a woman if possible. It was a dance club and I had many offers to dance, some of which I accepted especially if they were attractive men, some even got to do very close dancing holding me close, I was not sure how Emma would take this development but when she got me alone she was kissing me as though we were in private, either she was making a show of owning me, or she was jealous of the sight of me dancing with men and that had turned her on, whichever I was enjoying the results which came to a fullness when we got home and I could release my man bits from the control pants and enjoy intimacy to the full.
Sunday I had the idea to cross dress and go out around shops to see how I felt about being out in daylight and in full view of the general public and possible humiliation. My hair restyled quite easily, I did my face in a bland style with no bold colours or striking definition, then I went for jeans and a nice sweater with a pair of flat shoes. The outing was no big deal to Emma, she had been doing the shopping for weeks in her masculine style, and the only difference now was her hair and maybe a wearing a black shirt made her look more butch, which was her aim.
I was nervous to start with, but after a few hundred yards and no comment or obvious stares I relaxed and started to enjoy myself walking alongside my partner, looking in windows and talking of what we saw. After a while we stopped for a coffee and reflected on how this outing had gone compared with the last time. That had been good and very new without thinking how badly it could go, or how I had looked fairly Paul like, whereas now I was definitely more Emma than Paul.
Having been out daytime and survived my confidence increased. Over the following weeks my life changed even more, the Saturday evenings in town started to include Friday evening especially if I had the time to get ready. I was always found in nice knickers every day of the week and often in a nice knitted sweater at work, or with a silky chemise under my top. Emma had changed her skirts at work for trousers and a more severe blouse that while not a man’s was not at first glance a feminine style.
Then I had a new experience, I was in a bar early in the evening and waiting to be served, when the barman in an attempt to get my attention, he addressed me as miss, what was important was that this was the first time a stranger had referred to me as female, and the impact was to affect my attitude to cross dressing. I started to think of myself as female dressing as a man for work, I really took note of female mannerisms and the way they used body language, but most of all I stopped thinking of limits that my cross dressing put upon my non feminine days. It began with plucking eye brow hairs not just to neaten things up and stop a monobrow, and with the help of internet sites I taught myself how to redefine my eye brow shape. It was a few from the bottom to begin with, but slowly they thinned until I was satisfied I had a neat line that enhanced my eyes. I also became aware of my fingers and how the nails help make fingers appear longer and more elegant, so I stopped clipping them and filed them, then on a Friday evening I would paint them in some tone that moved them away from a man’s idea of how nails should be, ultimately my nails became neat ovals that were hard to disguise at work. I also had my ears pierced one evening on my way home from work, leaving the shop proud of my new decoration but disappointed that it would be weeks before I could do anything more than clean the studs and make sure they were not infected.
And then it happened, my style became open conversation at work, one Sunday evening we forgot to return our rings and by the time Emma had left and I was on my way to work I thought to remove them and just put them safe in a pocket, but my fingers were tight beneath the rings and without a lot of hassle they were not for coming off, so I compromised and spun the diamond round so it was hidden in the palm of my hand. I doubted people would notice, but Jenny who worked on the next desk did, I overheard her mentioning it to her friend at the water dispenser, along with all the other things they had been noticing, such as the nails, my well cared for hair, the ear studs, the nice sweaters I wore, and lastly a comment about how my eyes sometimes look darker on a Monday and my lips redder. When I had heard enough I coughed and they blushed embarrassed to be caught red handed gossiping, but I asked what they thought of my new style and explained how we had swapped rings but Emma’s had got stuck on my finger. They seemed not to know about my weekend style but agreed my work style was very nice and they had no problem my dress sense, or as they put it, a bit camp. And that released the brakes on my work style, but not before I had got a text from Emma ‘Hi Emma dear, as you still have the two rings on I guess you are still my wife, how about you cook me something nice for when I get home, I have been asked to go for a drink after work with some of the girls’ and those girls I guessed correctly were a couple of friends she had made at the weekend who were extremely butch. But I thought nothing of it; I had done the same in the past and expected her to run around after me.
Now I had accepted that I could dress comfortably for work I bought my first pair of trousers specifically from the ladies section, they were in black denim, a boot leg hipster style, I needed a belt to keep them tight on my hips and control pants to keep the front flat. I wore them everyday for a week after getting them and reveled in there fit and unconformity.
While Emma was being more blokish in her behavior, having drinks after work, expecting me to be the little woman who looked after her, I was getting more feminine in my attitudes, I had found myself looking at a few men and recognizing that they were attractive to women and wondering if they might be attracted to someone like me when dressed up, I also found the joy of high heels and was to be found exclusively on narrow spikes at least 3" high if not higher, I loved the way they altered my posture and way I walked, no longer could I walk like a man, I had to take short steps, swing my hips and never be in a hurry to get anywhere, sometimes they made me feel vulnerable, at others sexy.
And then it happened, I have no idea why it took so long, I had been presenting as female for six months at least once a week, and increasingly camp as the months had passed the rest of the time, I had also been studying fashions and the female look nearly from the beginning. But I was putting away the clean clothes and hanging my silk blouse in now my wardrobe, when I looked along the rail found Emma’s small collection of dresses and skirts and had a good appraisal of my find. One black dress, high neck long sleeves. One long green denim skirt. One very full olive skirt, calf length. One short straight brown mini skirt. And for some reason my mind was set on wearing at least one the following weekend. First I did my research and from stories I had read about cross dressing I had to clear all my body hair for skirts to work, hairy legs were the domain of men.
And so that Saturday when Emma came back with the shopping she found me cleaning in the long denim skirt, it was a terrible nuisance getting in the way all the time, but then cleaning in heels is not normal practice for many women either, I struggled because it reduced me to a wanting to look good over being practical, which a long skirt and certainly are not, but when Emma was able get the full view, hugged me and congratulated me ‘You are more a woman than I ever was, I could never feel right in something like that, but you look fantastic.’ Then she stood back for another look ‘I had been hoping for this day for a while now, for me you have stepped into a place completely opposite from the manly place you started from, and I love what I see and what it means to us’ then she hugged me again, it was then I felt an unexpected bump in the front of her trousers, I ran my pink finger nails down there and reassured myself I had felt correctly and looked in her eyes, ‘Well you go to some length to create a flat front, I am just filling the empty space at the front of my trousers’
Then I had another idea and wondered why it had taken so long to have it, confident of my overall image I told the boss I needed to go out and get something, I grabbed a jacket and shoulder bag and went to the car, the big skirt and high heels meant it would be no quick exit as I teetered to the car then folded all the material under me before shutting the door. Then I could drive away.
Two hours later I returned having been fitted with and purchased my own set of breasts, I was told they were size 34D and I believed her. They sat beneath my sweater jiggling about and pulling on my shoulders through the bra straps, making me smile every time I looked down, if the boss was going to enhance herself in the trouser department, then I would enhance myself in the chest department.
That evening I wore the black dress, 4 " heels, long pendant ear rings, a well made up face and another purchase I had made at the transformer shop, stockings, oh and a smile. This was me going overboard in a big way and knowing I could swim confidently in this most feminine of styles.
I had a great night out that time, I had gone past any notion of neutral dressing, I was, hopefully to all those observing me, female. The breasts weight and heels made me alter my posture and I felt myself walking more upright, more confidently, even strutting. Emma accused me of showing off. I was used to attracting a certain sort of attention from a certain sort of men, but this time I was attracting more attention. Maybe it was that the hem of the dress rode up and showed the stocking tops or maybe I just looked more attractive. As Emma went off chatting with her friends I found it easy to get a drink from lecherous men, then later I was popular on the dance floor, some men being very forward in where they held my body, making it clear what they would like to do later if I wanted to. Emma found all this very amusing and made sure I did not miss out on what they were offering.
It was later at home she let me know what she meant, as I was such a good looking girl we would not be using my man bits, we had had a dildo for years but this time as I used one on her, she pulled my thong to one side, lubricated my only hole in that area and used our thinner vibrator on me. At first it was like being at the toilet, but as she continued she found what she was hoping to find, I had a G spot, my sigh gave away the find, but then after I had begun to feel the sensation increase she came herself and then rather like a man, pulled out and left me wanting some more. There was nothing for it, when I went to get ready for bed I relieved myself when the thong came off.
My weekend dress became purely skirt or dress, and due to Emma having a small supply I had to go shopping for my own, experimenting with many styles, but mainly finding myself liking the longer flowing skirts, knee length for housework and daytime, the shorter ones for nights out.
My work style was drifting more towards the feminine as the weeks passed, Emma had her part in this, but mostly it was my own motivation. My tops had gone from a nice sweater to plain hipster trousers, and then to blouses, the trousers moved away from jeans to more female fabrics and cuts. My underwear started with knickers, then camisoles. This was my own choices, my hair and eye brow shaping was down to me as well, my longer nails was Emma’s idea, she suggested filing only the sides and letting them gain a more elegant shape. She also made my jewelry selection, early on we had swapped wedding rings then at first we accidentally forgot to swap back on Monday, but after a few times Emma just told me she was going to keep the wider man style, allowing me to keep her thinner pair including the diamond. She used this as a way of making the relationship change as well, while I wore the engagement ring she would treat me as a submissive wife and I went along with it and enjoyed the role. She also hid some things over the months, my underwear disappeared into her drawers, my shirts and trousers also went and if she did not like them they went to a charity shop, eventually I lost most of my clothes, that was a slow change, but the one that I consciously noticed was the time I was looking for my plain studs on a weekday, and when I asked if she had seen them she just suggested I wear something pretty, when I reminded her it was a work day, she shrugged her shoulders and stated ‘So what’. I went with some small hoops in knowing my long hair would cover them, but I was wrong and they were noticed, not in a dramatic way, but over time they became another thing on the list of things colleagues would chat about. Other things that changed over time were more to do with Paul’s original clothes becoming worn out or Emma taking them over, so shoes while not heeled or overtly feminine, were bought for work. A more visible change happened after we had an anniversary. It was a year since we had first tried our neutral dressing, I had been wearing dresses for a few months and Emma had become quite butch and wore the heavier wedding ring, so when she suggested going out for a special night to celebrate. She came home a week before with a new suit and I felt it was time to get a new outfit, I bought a spaghetti strap, bias cut red dress and new sandals, but the most important impact was that I had a hair cut. I was not sure what to ask for as I entered the unisex salon. Over the months I had experimented with hair dye changing my colour gradually from mousy to darker brown. The stylist brushed my hair about and held it in positions to give an idea of what she could do, I only wanted to keep the length but beyond that I said she could do whatever she thought would suit me, she also asked if she could lighten the top, in a moment of madness I said yes thinking I can always dye it if I don’t like it. I was really happy when I walked out hours later, apparently I had a permanent soft wave which gave more body, my fringe was now shorter which if uncontrolled would fall well across my face, and the top was lighter but in a nice streak pattern. Emma loved the style and when I was later dressed for our romantic evening I felt totally female, and with Emma in her new suit and a fresh haircut that had by then lost its feathered edges, she had even started wearing glasses with a heavy rim adding to the masculine look.
We went to a straight restaurant and felt totally accepted and not at all a bizarre novelty. Then when we got home she treated me to a lesbian love session, this time giving me an orgasm like I had never had before. Then as we cuddled in the after glow she made me agree that I would never want to penetrate her again only being penetrated myself would give me anything worth having in the future. I was to learn in the morning what this agreement meant, basically she had worked out how to hide my penis, she held ice to my scrotum then pushed the balls inside me, then with surgical tape fastened my penis between my legs. When finished I stood in front of the mirror, all I could see was a patch of pubic hair, ‘No more control pants, just lovely knickers from now on, and it will save us the choice of how we have sex’ she hugged me and gave me a very sexy cuddle, the area restrained still swelled but not visibly.
Monday was the day the impact of the weekend fun kicked in, I had streaks in my hair, if that was not enough the hair over my face would not reach the pony tail, which in itself was much fuller due to the perm stopping it from lying flat at my neck, I could get the fringe behind my ears but they did fall forward a lot. These changes affected the gossip once again in the office, I could not tell if the compliments were genuine or not. The new position for my trouser tackle took some getting used when I walked, or sat down and got in an awkward position. Later in the week I had a very shocking moment, I was answering the phone and the caller referred to me as a Miss, I nearly corrected them but basked in their mistake.
Some weeks later, possibly a couple of months later, I was in the kitchen preparing our evening meal when Emma breezed in, she had told me she would be late as she had some business after work, and from the look on her face I could tell it had gone well. ‘Well are you going to congratulate me’ she beamed
‘Well of course. Well done. What for might I ask?’
‘You may. I have today become the proud owner of Girls Allowed, along with Suzy and Jane. You will be a partner as well if you want. Good isn’t it’
‘I hate to sound defeatist, but what about your job, and Jane is a bit full on, you sure she will be equals?’
‘I got redundancy, so that covers our share, and your wage will cover everything here, and I am equal to Jane when it comes to it, no gay woman will get the better of me’
‘In that case I am happy for you, when do you open?’
‘Two weeks’
And that was how I became part owner of a gay bar, Jane and Suzy were a settled couple, much like me and Emma, Jane was the dominant one but Emma was far more masculine in appearance, and over the following weeks even more so as she directed the redecoration, and ran the cellar. I would help out at weekend along with Suzy who held a similar role to me; Jane was a naturally pretty and girlie woman, within no time our friendship had blossomed. She knew my true gender and while our partners were running their bar at the night, we would spend time together in the evenings as we both had regular jobs. This was a good time for me, she taught me a lot about make up and colours, and over next months she turned me into a far more feminine person, my clothes became more delicate, like my jewelry, and shoes by her definition had to be narrow heeled and sexy. She was also a fellow fan of stockings and introduced me to corsets. Saturdays became a fun day for the pair of us, we would prepare ourselves for our turn in the bar and wore some wonderful clothes, silk and satin were or favoured fabrics, and Jane and Emma’s pleasure
A crisis occurred in my life about six months later, I would go down to the bar after work and at times I would meet up with Suzy and go out. The Suzy evenings in particular were a dressed up time and as a consequence I was presenting far more female traits while at work. The crisis started when I was at work and a colleague asked if I had been wearing make up, if I had not been out with Suzy the night before I would have known my face was clean, but I had and I must have shown my embarrassment, I blushed, she giggled, and I left for the toilets to check in a mirror. But the problem started properly when I went through that door, I was insulted by a man calling me a puff, and told me to use the ladies, already distressed by my embarrassing encounter, I turned and left, just before I did enter the ladies, sense came to me and I stopped myself, this would have been a terrible thing to do, being called queer would be nothing to what a man in the ladies would get called. I hung about the gents until it was empty then went in to check my face.
By the time I had got back to my position in the office there was a lot of activity not connected with work, and the line manager waiting to see me. The next few minutes were a blur, but I was asked to leave, for the sake of getting the office working efficiently, and it would be good if I did not go back. I said you can’t do that, she said she was sure she could find something in my conduct that would give her cause to sack me.
Well I was really upset as you imagine, I got home before Emma had left for the bar, and after calming down and telling her about the incident, she took the whole thing in her hands, contacted a solicitor, and rang work to find out what their side of the story was. She reckoned I should accuse them of wrongful dismissal and get compensation. She went to work later, leaving me to do some housework.
Words that passed between work and Emma meant that I would not be going into work anytime soon. So Emma suggested I work at the bar until I found another job. This was like a release for my female persona, I was able to wear skirts all the time, my nails could be painted with whatever colour I wanted, my pony tail was no longer necessary, but the most fun was wearing the fake breasts as a permanent fixture once I had mastered the adhesive to hold them in place. I made it hard work if I ever wanted to go out as a man, but I did not care I was happier now I could spend time dressing and going out in a pretty dress and heels.
Emma and Jane had developed a style that was best described as builder, heavy boots, jeans, T shirt and of course the short hair. And then as I started working more hours, and Suzy spent more time in the bar, we felt we should have a style when we were working. The bosses only asked it was as girlie as possible. Suzy and myself had a great wine fuelled evening discussing what we would like to do, coming up with many suggestions, Victorian, slutty, whore, French maid, 1950s, schoolgirl, summer holiday, Arabian nights, fetish.
The next day our list had gone and replaced with a note, ‘very interesting’, was all it said. On the phone to Suzy she guessed our ‘men’ would be picking their fantasies out of the list. She was right, Emma and Jane had gone through the list, Victorian was crossed out (skirts too big), slutty and whore more for a certain type of male gay club, summer holiday was not interesting enough, Arabian nights was a maybe, which left french maid, 1950, schoolgirl and fetish. They had also been in touch with a theatre costume outfitters that Jane knew off and had made appointments for us that afternoon, strike while the iron is hot they said.
So dressed in a nice silk blouse and pencil skirt hoping to make a good impression, Suzy was there when I arrived in her empire line dress, also looking very stylish. The manager greeted us and invited us into the rooms filled with racks of costumes, I would have loved to have been allowed to just roam and check out everything, it was like Aladdin’s cave, glorious.
‘We need to find you a costume it seems, Jane has filled me in on what she would like, do you have anything you would not like?’ she was all business and very matter of fact. We explained it was for work and how we wanted to be noticed, ‘No problem with that, I am sure you will be unmissable in what I have in mind for you both. Follow me.’ She lead us to changing rooms and asked us to strip to our underwear, then she supplied corsets that we fastened each other into and clipped our stocking onto, then she gave us the dresses, short black maid dresses with frilly underskirts to make the skirt stand out. With little aprons, white cap and white cuffs fitted, she asked for a look. ‘You would need some black stilettos and your hair pulled back from your faces, yes they look good. Do you like them?’ we explained how we were not sure about our stocking tops showing, but she put that one down, explaining how that was part of the fun of this dress. Next after undressing down to the corset she gave us a choice, one was a knitted top and cardigan with a disc skirt in lemon, the other a dress with a square neck, tight waist and flared satin skirt in pale blue, Suzy went for the dress and with her very real breasts showing at the top looked sexy, I settled for the more modest knitted top, then we were given net underskirts to give the skirts body. Grace pinned the dress so it fitted Suzy better at the waist, and told us we needed seamed stockings, with either white or a matching colour stiletto, she must have a thing for those particular shoes, then explained that hair styles were engineered then, piled up, backcombed and held in place with tons of lacquer, the hair was something women did and slept with in a net, not like today’s relaxed styles. So we accepted that the 1950s was not worth doing for one day, when Grace suggested we do what the 50s women did who visited the salon once a week to have the style reset. Now to us that sounded like fun, a weekly salon visit, but would our respective partners allow such extravagance?
We left loaded up with bags, and our purses lightened. It was getting late and we would be needed in the bar soon so we decided on doing the French maid that evening, we could put our hair up in a clip and the rest was pretty much regular dressing. After collecting a few items from our homes we changed in a private room at the bar, helping each other to lace the corsets up, and zipping the rear fastenings on the dresses, then after a final inspection of each other, we entered the bar to see what the bosses thought of our uniforms for the night. Jane made it obvious Suzy was hot, her hand went onto her partners arse and squeezed it, Emma just pinched mine saying ‘You had better get used to that’
And she was right, it might be a girl only bar but some were just as arrogant as men, and certainly did not hold back on the sexual advances. Come early morning and we were closing up, Emma told us how good we had been at getting extra orders as the takings were up, but Suzy and myself had loved the whole experience of dressing up in costume and enjoying the dresses, we couldn’t wait until the next opportunity. So when the bosses suggested we do it again on the Saturday, the next day, and we said yes. Then over a drink we explained how the 50s look would take more preparation and maintenance, that if we did what Grace had suggested, doing it for a week or more to get the full value from the effort. In their easy mood they agreed that we should maybe do each uniform for a weekend at least, maybe a week if it was suitable. Suzy and I just looked at each other; we had permission to do whatever we wanted, this was going to be girlie heaven.
On Tuesday we meet for a nice long look at 50s images thinking how much fun the week ahead was going to be. Wednesday we had our salon appointment, taking pictures of how we hoped to end up. Suzy had bleached her hair to a shocking blonde, I had my highlights dyed back to the main colour, then the stylists set us into our new styles and we walked out feeling very conspicuous with what felt like was extreme hair. Suzy had a long bob with her fringe curled and flicked to the sides, mine was a beehive, imagine Marge Simpson, backcombed and piled up on top of my head, and the stylist even added some extra foam to help with support, laying my hair smooth over this construction. Of course we both had enough lacquer to hold everything in place very firmly. Maybe they were extreme but we could only smile at each other as we made our way back to the bar so we could get into the rest of the costume. By the late afternoon we were ready for work, corsets on, seamed stockings, our dress and skirts flaring out over the netting, then some make up and period jewelry, and off course 4" stilettos.
Emma and Jane loved the result and agreed the effort really did justify the decision to keep the style till the weekend. The bar did well; customers loved the costumes some even coming in dressed similarly later in the week. On Friday Jane and Emma surprised us by coming in dressed as teddy boys. The hair was hard work, sleeping was hard as mine was uncomfortable, and then the repairs required in the morning caused us to get through a can of spray a day.
We even went back to Grace to get another outfit; one outfit for a full week would not satisfy our desires. We wore our costumes fulltime as it seemed wrong to have 50s hair and current clothes, so we would do everything in our corsets and net underskirts.
After that success we felt a more relaxed hair style should be used, Suzy’s was still blonde and looked fine when washed out, mine took a bit of sorting but on Monday was well conditioned and fine. We had our French maid costumes and we were told by the ‘men’ that the week would be spent being maids, of course no objections from us and come Wednesday we were in costume and serving customers, enjoying the costume and the reactions we got.
The following week we dressed as schoolgirls, not the slutty usual TV image of micro skirt and tight blouse, but we found grey pinafores and white cotton blouses, we put our hair in bunches or plaits, of course we wore make up and heels. Again the customers followed the style at the weekend; Emma found some shorts, grey shirt and school tie to join in the fun. Then it was back to the 50s and the beehive.
Over the months we became well know for our themes and people would be asking what the style would be in the future so they could join in, we were a lesbian bar but the themes created a lot of gender style separation, the more dominate partner more often kept away from copying my style, but would happily encourage their partner to dress up, while they copied Emma or Jane. A few regulars suggested ideas for the future, but we would refuse fetish and bondage because it was done elsewhere, though Emma did get me a dog collar and lead and Suzy admitted to letting Jane use hand cuffs on her, but we still thought it a poor theme for the bar. But one of my greatest buzzes was being lead by Emma with that dog lead, while dressed in the sluttiest outfit possible, for the pride carnival, the statement that I was hers and my position in the relationship was totally in her command, was not lost on me, or on Suzy who was handcuffed to a carnival float while Jane paraded around in a police uniform.
It was I think the third time we did 50s, I had my hair done in a bob and looking well but feeling like a helmet, I was wearing a nice satin pink skirt. Anyway I was ready for work and feeling good when Emma sat me down.
‘Got something for you’ and passed me a packet of tablets.
I read the packet, ‘Are these what I think they are? hormones?’
‘Got them off the internet, hoped you would like them, and I want you to take them’
I read the packet again and thought about what they meant. ‘You want me to never be Paul again; I would have great difficulty dressing as a man if they do what I think you want them to’
‘I don’t need or want you to be Paul again, I love you as Emma, but I also love those fantastic breasts that Suzy is flashing about some weeks.’ I did not know what to say, she continued ‘So you take two a day, here let me get you some water.’ A glass was put in my hand ‘Now you can look forward to real tits’ I swallowed as instructed, she knew I would, but I did wonder how my parents would take me if I could not be a convincing man, well camp man if I really tried to tone things down.
Then she pulled out a second packet, ‘So you are not alone I have got myself some testosterone, I fancy a beard could look nice on me’
I stared at her as she swallowed a pill, ‘you sure about this?’ I asked
‘Double D at least I am hoping for’ she said with a grin.
‘But they can affect your moods these things’ I picked up a packet.
‘Yes I hope so, your going to have to get used to mood swings, feeling vulnerable, being weaker and for me you will look womanly in your appearance when naked. I know you will love it’
I never argued I always did as Emma asked anyway, ‘But what about you?’
‘Apparently I might get a little more assertive, which I know you like, and if it gets out of hand the emotions, that is, we can reduce the dose till we get used to it.’
‘Should I say thank you?’
‘You will in three months when you get rid of the artificial tits and let me fondle your real nipples nestling inside some sexy satin bra. That is if you can handle the maximum dose they are suggesting’
I looked at Emma and imagined her with a hairy face, then thought what real breasts would be like when they bounced around in the bra she was suggesting, or as I imagined the nipple being nibbled by Emma in a most arousing manner. I then agreed ‘Off course I want a hairy husband just as much as you and I want a pronounced pair of tits on this chest. Look good on top of the corset too, I guess’ I added a smile with that thought. But I was still concerned how my father would take the news that his son had become a daughter, but with the bar being so time consuming I had not visited in months only making calls to keep up with each other, so the truth was not really being conveyed well.
Within a week I felt my skin get sensitive and I had felt a little weepy one day, Emma however, well she was used to bossing me around, but it had been in fun or so I thought, now there was an edge to her instructions, less of the ‘would you’ more of a ‘you will’ attitude, and come love making she was so dominant. It was a french maid week and while I was in the cellar sorting the empty bottles, she came up behind me, grabbed my bare arse (thong) and informed she was feeling randy and me strutting around dressed like I was just meant one thing, she was going to take me. There was a handy table that she laid me across, and then proceeded to fuck my arse until she came. ‘My god that was good’ was all she said before going back to the bar. Leaving me feeling a little shocked at the treatment I had just received, but in some unexpected way loving the way she had just dominated me so completely. I was totally hers now, and I was happy to please her and make her happy. Even so I hoped it would not happen to often.
Emma certainly did become more assertive to the point where Jane and her had a big row. Then when they had cooled down, Emma realized that maybe she should reduce her hormone intake. A few days later she was back to an acceptable level of assertiveness, not the aggressive nature we had seen earlier. I however was not going to be reducing, I had a terrible day about three weeks in, I went home to get my emotions back together, which seemed to work, but a few days later I was home again after crying floods of tears when Jane told me I had made a mistake with a customers change. At four weeks I wanted to reduce my intake, but my chest had big brown nipples and rising mounds beneath them that Emma loved playing with, so I was told in no uncertain terms, I keep to the dose and if I could not work then I would have to stay at home until such time as I could handle my emotions.
My life was now a roller coaster of emotions, Emma would be nice to me and I was high, then something went wrong and I plunged into hopelessness, all the while wanting to please Emma who had become my focus. We were both happy the way my physical shape was changing, maybe because I had been wearing a corset so much, but my waist had reduced and besides my breasts inflating to a B cup by seven weeks and my bum and thighs had filled out. I no longer used the silicones and I was buying underwear weekly to keep up with my expanding shape.
By week ten I was getting used to my turbulent emotions and had bought C cup bras to handle the recent increase, I was even able to work not just visit the bar and feel sorry for Suzy who was having to work even harder to cover for my ineffectiveness, but she said she understood and puberty is hard for any girl.
Week eleven was a 50s week and I felt up to doing a full week so accompanied Suzy to the salon for our styling session, Suzy was going for a rock and roller chick with a rolled scarf holding her hair back and tied in the nape of her neck. I said something special to the stylist, she asked if she could try anything, to which in a moment of madness I agreed to. Compared to Suzy’s easy style, I was in there for ages. I came out with a proper perm, tight clearly unnatural kiss curls were secure around my face, the rest of my hair though straight seemed to rise from behind my fringe a good inch or two before falling to a very precise under curl between my shoulders, my ears were on full display as the hair flowed behind them and curled behind, ready for some fantastic ear rings. The whole thing was rock hard with loads of spray holding everything in place, next I had an appointment with Grace for a new outfit, this time I arrived in my corset and when I stripped showed a good 36 — 24 — 34 figure, she actually asked if I had tried getting my waist smaller, I told her 24" seemed good, so she brought me a skirt which unlike the previous flared styles was what I at first thought was a pencil skirt, but when I looked closer it actually tapered in from the hips being visibly narrower at the hem, several inches below my knees, thank goodness for the rear slit. When I tried to fasten the zip I caught a smile off Grace, who offered to help me create the right waist for the skirt, explaining how the skirt looks best when it really comes out over the hips then nips into a tight waist. She pulled my laces down to 22" and this allowed the skirt to close. Then with a satin blouse that had darts emphasizing my swelling chest and a neat jacket that had an equally tight waist, Grace declared me a 50s film star.
My reception at the bar was brilliant, I had undone a few buttons so I was flashing some cleavage, and with such a tight skirt all I could do was mince into the bar and say ‘Hello darlings’ Jane saw me first, and asked if it was me, I confirmed I was me, to which she said ‘Fuck me’ I replied ‘If you want, but I would rather it was me getting fucked’ she laughed and looked at me in a funny sort of way that made me think that maybe she did fancy having me in some way. Before my thoughts went to far Emma appeared and let out a whistle, ‘Now that is what I call sexy, all those curves, sex on two pins, fantastic’ then turning to Jane ‘Mind looking after the bar for a little while, I want to show my wife something’ Jane winked and Emma took my hand, then as I passed her she slapped my arse. I knew what was coming. She had me undress so the clothes did not get spoilt and she could admire me as I strutted around the room in corset, stockings and stilettos, then she gave me such a fucking I came so loudly that a few days later Suzy explained that the whole bar fell silent listening to my moans, and then when Emma went back into the bar she was clapped by some customers, she calmly stating that it had to be done if I was going to walk around looking like I did.
I did not wear the straight skirt all the time, but when I wanted to feel that sensual skirt and blouse arousing me, especially now I could go without a bra and feel the satin on my nipples, there was only one thing to do, wear it and run the risk of being fucked by Emma once more.
Week twenty after starting on the pills and I had reached Emma’s goal, I was a DD, most tops strained to cover my new shape, and with a corset pushing them up I had a very prominent bust, every bit as good as Suzy’s. Emma loved it when I bought my first DD bra, red satin push up worn under a sheer red blouse was more than her frustrations could take, I was back in the bedroom with my mini skirt pushed up past my waist and feeling her pushing inside me once more. I also learnt that if I wore such clothes I could get Emma to agree to almost anything, her mind was so distracted by what her hormones were telling her she should be doing. I started by asking for some money to get a new top, one she would like I emphasized, and once she had spent herself on me I casually took some money from her wallet and promised to be naughty. I was not alone I discovered, Suzy could do the same with Jane, maybe we act submissive but we have our ways of evening things out it appeared.
Life between my legs became easier as well, the hormones left me with a rather small flaccid piece of skin that had only one use, peeing, so I stopped using the tape and even when it stiffened no one noticed so I was now a proper busty woman able to wear the most provocative clothes showing off my cleavage and cute arse. It was like a new lease of life to me, I still loved the 50s stuff, tight lined skirts being my number one choice, but the flared skirts still looked good if not as a sensual. But I had found the delights having a real cleavage, and the tops that allowed me to wear seemed endless, the ones that clearly exposed skin, but there were the nearly transparent blouses giving the bra a viewing, and well fitted tops which hugged the shape of my chest leaving no room for imagination, I had a big pair and loved people seeing them.
At the bar I would not be to in your face with it though, keeping with the themed costumes, but it was hard to hide my big chest which meet with approval from the butch dykes such as Jane. One Sunday after we had closed and having a wind down drink, Jane was asking how big I was, so I told her, she doubted I was right as she thought her Suzy was bigger, I assured her of my cup size, but she assured me like everything else size varies between manufacturers. I cannot recall the full debate but me and Suzy ended up topless so Emma and Jane could compare tits and see who had the biggest. But it turned into something else as we first posed then lifted them up with our hands, then asked to compare each other’s, then Jane used her hands to compare them, but as she cupped mine the nipple which had been aroused by Suzy’s touches decided now was the time to show itself. ‘I think she is liking this’ Jane said to Emma.
‘Great assets and really sensitive’ Emma replied.
‘Go and let Paul check yours out’ Jane said to Suzy. (Remember we swapped names as well a rings way back, only I refer to Emma as Emma, everyone else calls her Paul and me Emma)
Suzy did as she was told and went over to Emma who fondled our friend’s chest. ‘Hard to say which is best’ Emma said. ‘Tell you what, blindfold us and then we can have a purely feeling try’
We complied with their wishes, and as they sat before us we let them fondle our tits. Then Suzy rubbed a nipple across Jane’s lips who reacted with her tongue, ‘Very nice, now the other one so I can compare please, and do the same to Paul can’t have him missing out’
So I let Jane kiss me while Emma kissed Suzy, then we swapped back, I looked at my near naked friend she was really enjoying this and whispered ‘I am so wet, if they don’t do something soon I will let you get me there’
‘Now that I want to see’ insisted Jane who overheard the whisper.
I looked at Emma, ‘You used to be quite good with your tongue down there as I remember, shame to let Suzy get her knickers too wet’ we had always been faithful, but here I was being told to have sex with a friend by my partner, while they watched.
Suzy was wet and very excited, so a few licks and she started to tense and moan. When we had finished I got up and wiped my face. They had both enjoyed the short show and as Jane turned to Emma I had an idea that things might turn far more pornographic. ‘Mine seems happy, but yours must be keen by now’ Jane said.
‘She’s always keen, you should know that, makes me have sex all the time. Not seen any action today though’ Emma was smiling.
‘Poor thing, better help her out of her misery then’ Jane too was grinning while they talked about me as if I was not there, like I was something Emma looked after, a possession.
‘Be my guest, I know you fancy her and want to find out how her non standard hole is, so go on get your prick in her and make her scream.’ I was still looking at Emma, partly in shock, partly in anticipation; she had just given permission for Jane to have sex with me while she would watch.
‘You can have mine if you want, no point you missing out’
We were both possessions to be shared it seemed. There was a moment when I wondered if it was all bravado, but then Jane took my hand and pulled me towards her. There was not much foreplay, and Emma was giving instruction on how to get the best position, then I came and as instructed, I screamed. Jane came too a few strokes after.
‘Come on Suzy, the poor guy is the only one left, give him a good screw why don’t you’
Now it was our turn to watch as Emma fucked our friend. It was quite a show as I lay in Jane’s arms leaning against a wall.
Exhausted we all relaxed on the floor. ‘Go and get us a drink Emma’ Jane instructed, without a thought I got up and walked into the bar for a set of drinks. I walked back in with a tray and nothing else on. ‘Shame we cant have you serve the customers like that, but our pleasure is their lose’
We drank up and got dressed finally we went home and slept in on the Monday morning, after a late breakfast the topic of last night came up. With questions like, ‘What is it like with another person?’ did you like it? And statements like, you were sexy, you looked like you were enjoying yourself, I reckon Jane would like to have you again. Emma was not discussing this with me, she was assessing how her asset had faired in the situation, and from where I was she had just found another a new avenue of fun for us, as usual I would do as I was told, and to be honest if Jane wanted me again I was not going to kick up a fuss, she had been a good fuck, as they say.
We did not meet up all four of us until Wednesday, and it being a maid week we were in the short dresses which allowed the bosses to be rather free with their hands on our bare arses, they did not care whose they fondled, it could be either of them feeling me up. But it was Thursday when I really appreciated my position in the relationship, Jane and Emma over a drink had been reliving the weekend fun and obviously entertained the idea of trying something similar. Because when they came back to the bar, Emma just told me in a matter of fact tone that Jane was taking me home with her, and I would please her. I asked what about Suzy? The reply was simple, she would be sleeping with her that night. We had not been asked, just told, they fancied a change and that was all that mattered.
I caught up with Suzy later and asked if she had heard the arrangement, she had and seemed ok with it, I tried to say something about Jane being with me and did that not feel wrong, she just told me to make sure I made her a coffee before she got up, and to let her go on top for sex. She had accepted her submission without question, I had also but did not want to upset my friend.
It was the only time our partners exchanged their women, I think it was their way of proving their domination over us, and maybe just a little bit of fun along the way.
Now I was completely under Emma’s authority she decided that it was time to come out to our parents properly. As if I had a choice she visited her mother dressed in casual androgynous clothes, where she told her that she was gay and that Paul (me) had gone for another woman, so they would not be seeing Paul again, but she did have a new friend, Emma. Her mother, she told me took it well, she accepted the gay thing and thought it funny that her new friend was called Emma just like her. Very funny I said.
My parents were in for a bigger shock, we drove out and Emma went in to have a word first, explain how I had changed while I waited in the car. I had dressed conservatively, plain brown skirt, cream cotton blouse, hair down and light make up, no need to let them know how racy Emma really liked me to dress. Well after what seemed like ages my mother came out to the car wearing her gardening stuff, corduroy trousers and a sweater, my father’s I soon found out. She told me to come into the house as we needed to talk, then I saw my father, he was preparing a meal and to do so he was wearing an apron, but not a plain cotton or one of those humorous vinyl ones, no he was wearing a full on frilly pinafore style apron with frills on it and a big bow at the back.
We did indeed need a chat, I was a little shocked to find out how similar their relationship was to ours, mother had always been the one whose word went, but it seemed since they retired mother was spending more time in the garden and father had become a good cook, so for those tasks they used the clothes they had, albeit the wrong gender, but mother said father looked cute in his apron, and maybe he could follow my example and try something more daring. She was wearing his clothes all day and going to the shops in them like Emma used to, I doubted they would repeat our experiences but father when he had me alone did ask how it felt to dress in skirts, I told him they can be very sensual and stimulating, then he asked how did the bust feel, heavy but lovely was my answer. He concluded I was happier a girl than the boy I was born and I agreed I was one happy girl. And him I asked, oh he was just being practical, he said, but from the glint in his eye and the way he looked at my legs and bust I knew he was lying.
He would be here for half seven and it was just after five. I had finished work as early as possible so I had as much time as possible to prepare for the evening.
The ingredients were all chopped, the chicken diced, the pans out. The table was laid for two with candles as a centre piece. The lights on dim with a few scented candles around.
Now time for me. I had shaved all over the night before so the nicks could heal, the red spots from my missing eyebrows had gone. I showered in my favourite apple shower gel and dried myself before wrapping the black silk kimono round me. If I was not excited and in the mood, I was now. In the bedroom I had my outfit laid out. Satin purple coloured bra and knickers. A matching waspie with suspenders for my shimmer nude stockings. Now for the makeup, perfect foundation, blusher to highlight my cheeks, eye liner to define the lids, a bronze on my lid with a cream below the brow, blended together then two coats of lengthening mascara. Last the dark pink lipstick with a 12 hour promise to not wear off, I expected to put that to the test later. Now I nearly there, the soft jersey wrap dress sat wonderfully on my body, I fastened the inside tie before making a simple knot in the belt.
My black heels slipped on next, the dark pink nails showing through the straps. Long jet pendants were pushed through the holes in my ears, then a short string of jet beads sat round my neck matching the string on my wrist. I put the emerald ring he had bought me for Christmas on my left hand where I fancied an engagement ring might sit. Three dabs of Femme perfume, wrists, neck and down below. Now just paint my nails and let them dry while I wait for him.
Right on time the bell rang, I checked my curls were still as I had placed them not so long ago. I opened the door, Rob was stood there smart as always, dark blue single breasted, red stripe tie, white shirt, hair casually brushed back, and though I could not see them, silk boxers caressing his man bits. He stepped past me, kissing my cheek. 'Hello my love, you look fabulous.' as he offered me a bunch of red roses and a bottle of Merlot.
'Oh just something I found lying about.' teasing him, I knew it was his favourite 'would you open the wine and let it breath, here let me put those lovely flowers in some water.'
We kissed properly before I moved to the kitchen, I had not eaten since breakfast and was needing food. The risotto cooked quickly and easily allowing me to drink some of his wine. We chatted about work, about a few mutual friends as the rice meal disappeared and the level in the wine bottle lowered. A meringue, fruit and cream delight followed, all in one big dish so we could help ourselves and at times feed each other. It is very erotic to place a spoonful of cream on someone’s tongue and see them wrap their lips around it and lick it all off.
We adjourned to the sitting room and I put the TV on, the reason I would not go out and had invited him round was that I wanted to watch Downton Abbey, I am a sucker for period dramas, not so much the story more the outfits the women wear as I imagine living such a grand live, the men look pretty good as well. I cuddle up inside his arm with a glass of wine. I settle down to the programme but we chat on and enjoy caressing each other’s bodies. He has a hand inside my dress cradling a bra cup, I have a hand on his thigh tickling the tender inside part. He moves occasionally to make himself more comfortable, I suspect as his ardour grows. I wiggle my bum to reposition bits which are getting excited as well.
The wine all finished I offer to make a coffee, but he declines saying he has something else in mind, I know exactly what as well. He catches hold of the ties that are holding my dress closed and swiftly undoes the bow-come-knot, the dress falls open displaying my matching underwear.
'Something you just found lying about?' he asked with a wry smile.
'Well they were lying on the bed after I got them out.'
'Talking of lying on beds.' his hands were either side of my waist inside the dress, his lips moving swiftly towards mine. I returned his kiss, while at the same time undoing his tie, then his shirt buttons so I can run my fingers through his hairy chest. He has helped my dress off my shoulders creating a purple pile upon the floor by my feet now. A hand strays down to his belt and fly, a hand goes inside and cups his jewels. He takes a sharp in breath, he would do anything for me right now if I asked. But it is he who asks 'Would you like to go somewhere more comfortable?' I reply by taking his hand and leading him into my prepared bedroom, sheets turned down, one bedside light on low, some gentle jazz playing quietly.
'Is this more comfortable?' I enquired.
He sat on the edge of the bed and removed what was left of his clothing besides those lovely boxers, black this time. We kiss and cuddle, we caress and stroke, we finger and squeeze all the places on each other’s bodies that we know bring pleasure to the other. Then when I can stand it no more I cover his pole with jelly and give him some to massage into my hole. What follows is obvious, I lift my legs while he goes between them just prior to opening my hole wider with his stiffness. Soon he is riding in and out and I feel him going deeper and deeper, touching that spot that will, with encouragement explode within me and make me want this man even more.
We lie next to one another, he has gone limp and his semen is leaking out onto my legs. I don’t want to get up and leave him, so I reach over and find the tampon on the side and ease it into my sore arse. Now I can go to sleep in his arms with the smell of his sex in my nostrils.
A perfect way to end a rather
There is no back story, nor do I know the future of this couple, but the reader is free to imagine how they got there and where they will go from here. If you want post some ideas in the comments. Hope you enjoyed it :)
A tale about how a man finds himself pretending playing the woman's role, and enjoying the situation.
Thanks to Tiffany for tidying up.
I will explain something of my childhood first. I had a tough time in some ways, but in others a great childhood. My mother did not like me playing hard sports like rugby and football.Cross country was acceptable and I was reasonable at it, even represented the school at times. But what mother wanted me to do was dance. This caused no end of bullying at school. I ended up an outsider because I never did team sports and was seen as a wimp for doing dance classes.
Having left school at 16, I got a job in a bank, nice clean regular, safe work that fitted in well with my dancing. I still did the classes that I had once resented and now enjoyed, but I also entered competitions and displays. Mother was still a big support and would come to as many as possible, as she always had.
When I was about 20 I joined a dance team. We did competitions and formation dancing, mostly of the ballroom categories. I had usually danced alone or with a single partner, to be in a team of eight was a nice new challenge, and I found a lot of enjoyment in being part of a team.
The reason for telling this tale starts when our coach wanted to get us to improve and felt that we should once a week have a session dancing in the opposite role.
So a man and a woman would reverse, so the woman took the lead, or we would dance in same sex pairs, taking turns to play the lead. This was successful, as we understood what our partners would be doing in a real way, because we had done it as well.
My best friend on the team, Daryl, always liked to partner me in these sessions, which I enjoyed doing. I did not mind that he took the lead role most times, and when I danced with Sally, and she took the lead, I used to comment how I would be better as the partner, playing to her lead if we carried on.
The contests went well, and we got on great as a team, going out together and enjoying each other's company. My friendship with Daryl strengthened and though he made it clear he was gay, I made it clear I was not bothered, but we still spent much of our free time together as mates.
A couple of years after I joined the team, we had bonded really well. We danced well together and were winning, which always helped. Then disaster struck. Daryl's partner Trudy, sprained her ankle and though we had a reserve man, we currently did not have a reserve lady. So with two weeks to a national competition, it looked like we would have to cancel. We trained in a half hearted way. It was the next time we did the role swap exercise that Sally grabbed me and got all excited, she then shot off to see Daryl, who both went to see the coach, who then called me over. What they had come up with was that the reserve, John, would take my place with Sally, and because I was so good at dancing the ladies steps, I would take Trudy's place and partner Daryl! I expressed concern about how they thought it would work, also about whether I really wanted to be a lady. The whole team was brought in and the idea discussed. The whole mood changed, there was chance we could still enter and compete, if I would agree. I asked if I could have time to think about it, but by the next session I would have an answer.
After we split up, I went for a drink with Daryl, who was full of enthusiasm for the idea of dancing with me,and, reckoned it would be such a buzz. I was getting texts of Sally, Trudy and nearly all the others giving me more encouragement. Maybe they were doing it for their own reasons, but the pressure not to let them down was building. I hoped my mother would be a source of unbiased reason, how could I really be as good as Trudy, with such a short time to really practise? I had no outfits, I had never taken a step in heels. I could see so many negatives, where everyone else saw obstacles that could be overcome. Mother just thought it a real hoot, and told me it would be fun, with nothing to lose. My dignity I suggested might well be lost if I do. She suggested I might lose my friendships and team if I did not. I at least had to give it a go.
A resigned dancer turned up to training the next evening. What have I agreed to? was all I could think of. My mother had been out in the day and bought me a pair of dance shoes, and Daryl had called round early to give me a lift, chat with mother and make sure I was fine with it. And so I spent the rest of the week in serious training with Daryl. Every free moment we were together, so much so that I did not notice the hive of activity going on around mother, coach and Trudy. Come the weekend I was getting better, but not polished, when mother introduced me to the rest of the challenge. I was not only going to dance as a girl, I would have to look like one too. Somehow this had dropped out of my thinking, but Saturday morning meant it came back with a rush when Trudy dropped off her dresses. Mother loved them, the fabrics, the styles, the spectacle that is ballroom dancing outfits.
I was training in the afternoon, so mother had my morning fully programmed. First she showed me what she had been buying for me, not that this meant much, but as the morning progressed I knew a lot more. I had to remove all my hair with a cream, and then shower. Next I had some very tight pants to get on, then dance tights, followed by a bra, which was filled with a pair of fake gel forms. Now we had to try on the dresses Trudy had left behind. I stepped into the first, a pink full-skirted waltz dress with a tight bodice. Mother fussed around sticking some pins in, but basically it was a close fit. Next was a white one for the fox trot, far softer and more skirt to find my way through. Last was a tango, this showed too much leg and had a lot of frilly bits, and like the others would need some adjustment, but not much.
I was changing back before lunch, so I could meet Daryl to practise, when mother told me to keep the tights on and gave me some new heels. She said they were for the competition, and would fit better with the tights. Resigned to my fate, I took the shoes and her advice. Daryl noticed as soon as I put them on, but I just passed it off and got on warming up. At night, mother had finished the alterations, and wanted another fitting, so I obliged, only to have Sally call around, who enthused far to much telling me how great I looked. Then she insisted I go out with her for a drink. I accepted but not until I had changed, no way was I stepping out the door dressed like that.
We met up with Trudy and went to club in town. The evening was going fine until we had a few drinks and relaxed. Trudy asked about her dresses, which lead to talk about what else I needed to get sorted. But I was not to worry, they would arrange everything; all I had to do was do as I was asked and they would make sure I was presentable for the contest. We got home at a respectable time, being told I should be up early as they would be round to pick me up in the morning, and get me ready for the dress practise in the afternoon.
Naively, I thought they would just check the dress, and load everything in the car. No, I was to have a lesson in make up, and femininity. First they had me change so they could see me in the dresses, then they taught me how to apply make up; the foundation, blusher, eye liner, which shadow to use so we all looked alike, and lipstick. They did it first, then I cleaned up and had a go myself. After a few attempts and drying skin, they did me again, then slipped a simple hair band with wig attached on my head, let me step into the pink dress, before telling me I should go and show my mother how good I look. Mother just stood speechless for a minute, then gave me such a hug I found myself responding by hugging her. She was so happy I could see tears.
Sally suddenly shouted the time was late and we had to go, so I was out of the dress and about to go and clean up, but Trudy caught me, gave me her coat, and with mother placing the dresses carefully in the car, the two girls boldly took me out the door to the car, telling me I would be fine, no one would suspect, and I would only have to get made up and dressed once we got to the studio. Reassured, I hid in the back seat, unable to look out, for fear of seeing someone I knew. Then a quick dash indoors and I felt safer.
All I had to do was slip the dress on, everything else was done. So for the first time I sat in the girls changing room and watched them prepare for the session. It was quite illuminating to a naive young man. As we walked out I was given a wonderful reception. All the team came and gave me a hug and a kiss. Coach was thrilled and I tried to remember why I was doing this.
The practise went well. As expected, coach spent most of her time concentrating on me, until I became tired and emotional, at which point Daryl put his arm around me and soothed my fragile ego. Later on he teased me about taking the role too seriously, as I had never broken down before, unlike the girls who seem to do it routinely. To which I gave him a playful slap, how girly was that? I immediately thought.
After we had finished, I now realised I had only my female underwear to call my own and get home in. The girls laughed about this compromising position, but soon I had been lent a jumper and trousers. Admittedly the trousers did have flowers embroidered on them, and the jumper was pastel blue with ¾ sleeves, so I had to keep the make up and shoes on to get home. In the car, Sally was hinting at how we should plan for the next weekend, and Trudy was giving hints on what I needed to get before then. So when we got home and mother offered them some tea, it was an ideal opportunity for them to all get together and plan.
They wanted me to get used to the skirts, so I was to wear the waltz one as much as possible, it being the biggest and hardest to handle. The same went for shoes. I was to practise make up when I had a chance. They were going to organise appointments at Julie's salon, so come Saturday when we left for London I would look the part.
The week flew by. When I was not working, I was with Daryl training, and if not doing that, trying to get around the house in a ballroom gown and heels. That was once I had put on full make up!
Come Friday, I was thinking of practise, but Trudy was thinking of different preparations. Julie did all the girls before a big competition, and as I was now a 'girl', that included me. First she gave me a judgmental look 'what have we got here' then without too much chat, set about washing, cutting, and at the end my shaggy mop had been reshaped into a neat, decorated bun on the top of my head which had no life. It was just fixed solid, except for the deliberate wisps around my face. While things were being left to set on my hair, she examined my face and said she was neatening my eyes, and then pulled at my eyebrows. Then she manicured my hands and nails, gluing on longer tips and painting them a pink colour that all the girls were using that weekend. The tanning booth was not new to me, as we all needed a bit of colour in our skin sometimes, but the other thing that was new was having my ears pierced. They assured me that usually I would have studs and let them heal, but for this occasion, I was having the dangly ones fitted to start. Had I a choice, no!
Next stop for Trudy was our house, where mother had been busy. A bombshell was dropped on me, that I could hardly turn up at the event in my suit, then go in the ladies, so for the weekend I was to be Fiona, my chosen name apparently. So starting that evening as my hair was done, I should dress and be Fiona. Mother had loved this. She was shopping for a daughter she never had! I had a pink tracksuit and trainers, a denim skirt and a pale blue silk blouse, that was obviously picked for her taste, and a pair of heeled shoes to go with them. Along with enough underwear for a week. I stripped and redid my legs and arms, then I was getting dressed when I was asked to lie on the bed. Between them they checked my chest carefully, before applying something cold and pressing the breast forms on. I lay still as told, then as I got up, realised they had glued them to me! As I clipped the bra on, I was assured they had a releaser to get them off. Now with the tight pants creating a flat front, I was really seeing the Fiona they were aiming for. It was getting late so I slipped on the tracksuit, and the evening finished with Trudy telling me to be up early. She would collect me to take me to the final practise before driving to the venue. Then with a hug and a kiss, she was gone. Mother with a glint in her eye, then urged me to get myself ready for bed. As I opened the door and saw my bed I knew why she had a glint in her eye. A long purple nightie lay on top of the bed. Knowing that I was being told to do as I was asked, I changed for bed putting it on instead of my usual pyjamas, cleaned myself up and went to show her, so I could let her know I was doing what she wanted.
Next day, after a restless sleep due to worry and a very stimulating nightdress, I was dragged out of bed by my mother. Obviously pleased I had slept in the nightie, but eager to change me for the day. An hour later, I was waiting. Dressed in the tracksuit, hair repaired, and face done. After a couple hours final run through, I changed from the track suit, showered and dressed in the skirt and blouse, then it was on the bus and off to London.
The team behaved just as it always did. The fact I was dressed so unusually did not alter anything. We did everything as normal, until we came to allocate rooms. I was sharing with Trudy, so she could help me as she was not dancing. We had time to settle in and put our stuff away. It was during this time Trudy got talking and the chat drifted onto how I felt. She apparently danced partly because of the chance to dress up in such fantastic clothes, the textures, the detail just being so glamorous she said was brilliant., I had to agree the dresses were wonderful, but then my normal outfits can be special. 'Not as special as having all that fabric wafting around your legs', on this I had to agree.
The evening passed off without incident. I was too preoccupied with the thought that I was going to impersonate a woman in front of judges and an audience. We ate together, chatted and retired to our rooms, much of which I did not notice. Next morning, I was a bundle nerves, far worse than usual. Trudy must have been very patient as I seemed to forget all I had been taught. She had to do my face. Reset my hair, check I was presentable, and carry my outfits, almost everything, while I just went to pieces swanning about in the pink sweats. Once at the venue, she set me down and along with the other girls, got me ready for the first formation waltz. Quite surprisingly, once I had got dressed in the enormous pink creation, the nerves started to settle. And once we were on stage, I was completely focused and lost all my butterflies. Daryl danced beautifully, holding me just right, moving with such grace it seemed I only had to follow. The music finished and we all felt it had gone really well; even I had to admit I had done a good job as Daryl's partner. But it was the judges who decide what is good; all we could do was dance. We now had a break to change for our next dance. All four couples do a different style of routine, Trudy and Daryl always took the tango, and so I was to tango with Daryl. We had practised as much as possible, but you never feel it is enough. So we run through the routine in a practise area, just doing the steps until we are called. My nerves stay calm with something to do, and then once on stage, I focus on the tango and the mood of the dance. Daryl dances with passion, dominating the floor while I respond by worshiping him with my moves. We knew it had been good when the applause started, and the judges were generous. But it was the team's comments that really got us, things like true passion, if we did not know you better, and that was sex on the dance floor. Then somehow we had to calm down and do a foxtrot as a team. By now I was getting relaxed, and the foxtrot dress was a mass of soft skirt that moved sensually as I walked, and I remembered what Trudy had said about the dresses and I knew what she meant. These outfits are fantastic to wear, and dance in.
For me, the result did not matter. We had come and entered, gained experience and hopefully enjoyed ourselves. It would be silly to think we could win, but we came a credible fifth, considering that I had only taken Trudy's place two weeks ago.
The competition over, we went back to our rooms to clean up and change for a meal that evening. I was about to put my blouse and skirt on when Trudy offered me some of her clothes. Apparently I looked middle aged in my skirt! 'well my mother bought it' was all I could defend with. So she choose for me a mid thigh pastel blue skirt with a big belt, and an off the shoulder white top. She dressed in a similar style and with handbags for all our bits, we went to see who else was ready.
I bumped into Daryl as he came out of his room. He complimented me on how good I looked, and I blushed, as this is not what your friend is supposed to say.
We ended up at the bar together, chatting about the dances. He wanted to know how it felt. I was honest and described how the dresses felt, and how much I had enjoyed our tango, his passion and personality in it was wonderful to feel and be close to.
Later as we went to eat, Sally asked how I was getting on with Daryl; I said fine we are good mates. She asked if that was all. He is gay you know. And you are a man looking very sexy in anyone's eyes. Sorry what do you mean? He fancies you, and that tango was pure lust, and you went with it, so we thought it was mutual. Oh. Was all I could manage.
At the table, Daryl came and sat next to me. Maybe Sally was right, but it was confirmed when I deliberately touched his hand below the table, then withdrew it, apologised and waited. He said no need and took my hand gently in his and squeezed it. After a moment, I got up and went to the toilets. Trudy who had been next to me, followed and steered me into the ladies. I must have looked flustered as she asked what was up. I told her about the hand touching, and she asked if it was a problem. No. Did I like the attention? Well it is nice. So go back and enjoy it!
After reapplying lipstick, we returned. I saw Trudy wink at Sally, then gently stroke Daryl's shoulder. I sat down and found his hand on mine almost immediately. The meal finished and we split up as a group. Some went to the bar, others for a walk, it was a nice night after all. Daryl whispered as he got up that he was going for a walk, and would I join him? It even had the sense of power over me that I had felt in the tango. How could I resist? I wanted to know where these feelings would lead, so I followed.
Once a discreet distance from the group, he took hold of me and walked without saying anything, then stopped in a quiet corner, turned to me and asked
'the tango, did you enjoy it?'
'yes'
'I thought so, it was like you wanted to make love to me'
'was it?'
'oh yes, there were times I had trouble focusing, you were just so sexy'
'sorry, I was just responding to your dominant lead'
'look this is getting weird, you are my mate, yet I call you Fiona, and we have just done the sexiest dance I have ever seen or been in, and I want to carry on where the dance finished.'
'I m confused as well, but you were the one who started it, being so dominant'
'in that case'
he then put one hand behind my head, pulled me to him and gave me a deep long kiss.
'OK?'
'I guess so' I replied, as I got my breath back.
Then he held me against the wall as he kissed me some more. I was responding in ways I did not expect to, but found myself pulling him to me, then running my fingers over his chest. We were getting very excited, when he suddenly let go.
'it's no good here' took my hand firmly,. We walked back to the hotel, then went to my bedroom, where he asked my to put the tango dress on. While I did this he locked the door with a 'do not disturb sign' on.
I came out of the bathroom, to
'you are stunningly beautiful, and so sexy'
We danced to unheard music until we were almost glued together, at which point he was grinding his groin against me. In the moment I said nothing, just unzipped him then went down on my knees in front of him and kissed his dick, all the time thinking why? and that this is so good I love it! He came in no time, I managed to swallow everything, then he pulled me up after I had licked him clean, and hugged me some more. I was about to say we should be getting back when I noticed a paper slip under the door.
It read, see you in the morning. Love Trudy xxx.
I slowly undressed him, then as he watched, I undressed to my knickers. Then i went into the bathroom and put my satin nightie on and returned. It was not long before he was hard again, but this time he took control, and after gently massaging and lubricating me, took my virginity. Then stayed the night cuddling me. It was the best night ever.
Come morning, I had to get myself up and ready, but with help from Trudy, again I was soon presentable. Arriving home was odd as I was still in the skirt and made a quick dash indoors, hoping no one saw me. Mother was thrilled to see me still in a skirt. I could tell this by the hug I got. She then proceeded to quiz me about everything to do with the weekend, how the contest went, how I had got on as Fiona, how the others had treated me. I told her nearly everything, but there are some things you don't tell your mother. She came to the conclusion that I had rather enjoyed myself and asked if I would do it again. I tried to appear casual about it, but if given the chance I would love to dance again as Fiona.
I spent the rest of the day as Fiona to see how mother reacted, there was no real need, but she seemed quite taken with a daughter, but I tried to say it was possibly a one off thing.
Next time at the studio, everyone was discussing the past weekend and congratulating themselves when I arrived. I got a very warm welcome, I had made up for Trudy's ankle far better than any had hoped. After the session, there was some joking that we only needed one reserve because I could dance both parts. I laughed but the coach did not. Later asking if I would be the reserve lady, should it be required, Daryl overheard and shouted of course she would.
Later in the week, after Trudy had been over to collect her dresses that mother had insisted on cleaning, mother had a better idea of how the weekend had gone, giving me a quiet talk about how it would be fine with her if I wanted to be Fiona again, even if there was no dancing involved.
By the weekend, I was decided that I wanted to be Fiona again. My work colleagues had noticed my eyebrows were narrower, my hair had had been cut into an unusual style for me, and I had marks on my ears. Yet no one took great exception to these changes. So I managed to insert studs, and when I started wearing the nightie to bed, I knew Fiona was here to stay. Especially when Daryl rang, leaving a message with mother, that he had tickets and wanted to know if Fiona fancied going with him. This sealed it, and mother took over with the transition of son to daughter.
It all started quite innocently, my sister Leah was getting engaged, well she had got engaged and was now into the preparation for letting people know how things were between her and John.
It was an unusual evening we were all in having a meal together, that is Leah, mum and myself, Alex. This did not happen often as I worked shifts at the hospital as a nurse. Anyway Leah and mum were discussing things and I was keeping up with things until they got around to bridesmaids, and Leah turned to me with a straight in the eye look said. ‘Of course Alex will be one, wont you’ After I stopped choking, I said pardon, and she repeated what she had said. So I asked why. Well apparently when we were little we used to play dress up games, we had a box of costumes and would be all sorts of characters, you might think it was all dressing me up a girl, but we did boy dressing up as well. Anyway one of Leah’s favourite games was getting married, she was the bride and I was one of the other people, groom, father and sometimes bridesmaid if she did not have a friend round. I could not remember the incident but mum said she did. We were playing weddings, I had been the groom waiting at the church, and then as Leah (the bride) turned up I had to change into a fairy outfit and be the bridesmaid and carry her train down the aisle/hall. Use your imagination it was junior school kids playing. After a few more character changes with a bossy sister telling me to hurry up and change, we sat at a reception of biscuits and juice, I was in the fairy dress and Leah asked if when she gets married for real would I be her bridesmaid, and according to Leah I had said yes. I hoped mum would deny such things, but she compounded the thing by remembering fondly the time when were young and played at dress up, even saying that she felt it quite likely I would have agreed to such a request, and it very likely that Leah would have asked me.
I felt sunk, I said no as firmly as I could, but with both of them being very persuasive I was hardly a match for the two most important people in my life. So I started a defence of it will ruin your day, I will look awful, I will be laughed at, you will be laughed at, and John will not go with it, who will be the usher for our side? Unfortunately between them all these questions and more were answered, at least to their satisfaction.
They were happy that me made up and in a dress would not ruin the day rather would make it more special. I would not look awful; rather with a few touches I would look the part quite well. Nobody would laugh at me, or them because I would look beautiful. John would be easy, he knows how important the day is to Leah and will go with it for her sake. Our cousin Steve has already been asked to usher. With defeat creeping in I made one last stand, ‘Ok, in theory I am beaten, but if I look at all like a man in drag, I can’t accept being a parody, I have to look like woman, then, and only then shall I agree.’ I could almost hear them cheer as I said a reserved yes. Leah got up hugged me and told me this was going to be so brilliant, I was the only one she wanted as her maid and knew I would not let her down. In my mind I was thinking, what have I let myself in for, only me as her sole bridesmaid! And I do like it when she is happy.
The meal was now well and truly finished with just the dirty pots to clear away. It was mum who took charge; Leah was to clear up I was to go with her. Obviously my plans were forgotten, they were to have been an exciting evening dozing in front of soap operas, but don’t mind me I almost said as I realised I was being taken into mum’s room.
‘Right this is serious’ she had one of her looks on her that meant I am the boss, ‘before you find any reason to back out, I am going to prove that you have the makings of a woman, at least in looks’ another stare ‘right?’
‘Yes, what ever you say’ was all I could manage.
It did not take her long to have me undressed and wrapped in her dressing gown, then she attended to my face, muttering things like, not shaving makes things easier, you have such good features, your lashes are so long. Soon I was covered in the various products that I knew mum and Leah used but was not sure myself how they transferred from bottle to skin. Next a wig was settled onto my head and brushed out. And finally mum passed me clothes and explained how to clip the bra, pull up tights and get the skirt and blouse right. Last she found a pair of heeled sandals that my slightly bigger feet would fit in. now I was allowed to look, and at the same time Leah was allowed in the room. Mum looked on proudly, Leah smiled then started jumping up and down excitedly, and I just looked shocked. In mum’s mirror was me, I saw all the familiar features but instead of the hoped for man looking back, an unmistakeable girl reflected back. This was a bad moment, I felt thoroughly beaten, my last hope gone, as I did look female. Now how was I going to get out of this childhood promise?
I felt really awkward as I walked through to the living room, the clothes all felt different, my lips tasted different, my feet did not feel at all steady in the shoes, hair was tickling my neck and eyes, then as I went to sit and hopefully watch some TV the skirt got wrapped around my legs. I could feel this was not a good start, my confidence was low, and it really did seem a bad idea. Dressing up is very different to passing as a woman. They both were full of praise for how I looked and how great it was that I was doing this odd thing. So I tried to say how I felt and how I would never pass for a woman. Their quick answer was, of course the clothes take time to adjust to, and the look is not just a dress it is posture, expression and feeling that make it work. So I was going to have to learn all about how to look feminine, my heart sank, I had really hoped just to put on a suit and be the usher.
Eventually I was allowed to clean up and go to bed, where I had a disturbed night as all the worst aspects of this idea came round to tease my imagination. To my relief I was working a late shift and waited till the house was empty before getting up, then I could spend some time just being me.
This was a brief lull as it turned out. It was two days later and I was home in the evening to have all the excitement of my new ‘experiences’ pressured on me again. Mum had taken things in hand and been shopping for me, and now explained what and why she had made some purchases. First were shoes, I was to wear them about the house when I was home, then there was the skirt, which was a very full and long one, the same reason was given for this, I needed to get used to wearing such items so it becomes second nature to me. I could follow the reasoning but not the enthusiasm.
But for that evening Leah wanted to show me how a girl of our age would dress because when mum had dressed me the other night it had been mum’s clothes, and a mid calf grey skirt with a plain white shirt was not really suitable. So I was subjected to another session, this time by Leah. I was able to see a difference in the make up colours but it was the skirt that was shocking, it came above my knees and made me feel like I was going to expose myself. Once again I was stunned how easily I had been made to look so female, and as things were being pointed out to me about sitting in a skirt, I began to accept that maybe this could work especially if I worked at it, at least gave it a try.
And so next morning when I got up I slipped ‘my’ skirt and ‘my’ shoes on as I did things about the house, just as I would have put on jeans before going on shift. And as the morning passed I realised how I was getting the hang of the skirt, the heel on the shoe was different and would take more adjustment by me before they were easily accommodated.
I had a week with my new clothes, but the first time I wore them after work was very odd as I was preparing the veg for tea when mum came in. I felt very self-conscious stood in the clothes, but she put her bag down then came over and kissed my cheek as she asked how things were, which was more how she treated Leah than Alex.
So after a week I was used to wearing and being seen in ‘my’ new clothes. Next I was given a top to wear, I immediately realised this was not the sort of thing either of them usually wore, best described as a mini kaftan, the sleeves were long and wide with a very loose body, obviously this was something else to help me get used to female dress, and it did work. The sleeves were hard at first, dipping them in anything that came near, like water or food, but soon I was able to wear it without thinking about it, and when I caught myself adjusting how I used my hands without thinking of the sleeves I was genuinely surprised.
They were both pleased with how I had learnt about ‘my’ clothes and wanted to move on a bit. I had a day off at the weekend, which they said would be ideal for the next stage. Leah wanted to give me a lesson in make up, first she applied it to herself and I watched then I was to do myself while she commented, and once I had got it just right she would clean it off and have me do it again. Then in the afternoon we did the same but using different colours so I could see how they changed the look, and tried to find a style that suited my face. All the time I had been in my clothes but towards the end of the afternoon she opened her wardrobe and suggested I have a change. I ended up in her denim skirt and a cream jumper with opaque tights covering my legs.
The evening would have been uneventful except for one thing, it was Saturday and Leah would be going out with John who at half seven let himself in by the back door to find me washing up the pots, he said hello asked if Leah was in and went through to the living room. Moments later he was back, with Leah beaming behind him.
‘My god Alex I am impressed, I just took you for a cousin of Leah’s, I can’t tell you how good you look, seriously good’
When I joined them John was still full of praise, he had had similar doubts as to whether I would look good and whether I would actually go through with Leah’s plan, but now he could see the results his worries were over. I even got sucked into going out with them, only for a drive to a country pub and sitting outside with a lemonade, but it was outside and another step in the direction of being Leah’s bridesmaid. What helped me was watching other customers and realising nobody was taking any notice of me, Leah even went to the bar and lingered so she could take a wider view and came back to say I was going unnoticed. This made me feel a lot more comfortable because a man in a skirt was definitely not one of my favourite scenarios.
Nurses don’t have regular work patterns, so next day I was up early and came home that Sunday afternoon to meet mum and Leah setting out a timetable for me, or at least that is what it seemed to be. Once I had changed they wanted me to have a chat, more like listen. They were over the moon with how things had gone the night before, and how I was adapting to the clothes, so they wanted me to try some other things. I was given some shopping bags, they wanted me to start wearing panties, and they had bought some vest tops that I could wear as well, there was also a smaller bag with some cosmetics, moisturiser, lipstick and mascara. Also a book on fashion which covered clothes, make up and hairstyles, which they felt would be good for me to read. The full gravity of what was happening occurred to me when almost in passing, a comment was made about my not needing briefs anymore. I said nothing but over the next week I noticed my briefs once in the wash did not return to my room, and when I mentioned it she told me I had knickers to use, I assured her I wore them with the skirt, but she seemed to think I could wear them to work as well. I tried to protest but she asked who would see, and anyway the knickers are for more comfortable against the skin. And so I started to be a fulltime panty wearer, I was also persuaded to wear the vest tops under my nurse tunic. I was also embarrassed to admit it but the fabrics were much nicer than I was used to, the skirt was a very soft cotton, the kaftan had satin parts and the silky knickers were so smooth on my skin, after a week I felt that if I had a real choice then I would probably pick panties over my briefs. Now there was a turn around, at least I thought so anyway.
Over the next two weeks I was not pressured with anything new just allowed to settle into the new things. I did read the fashion book, and of an evening played with the make up items and began to moisturise regularly.
So four weeks after being persuaded that I had once said I wanted to be Leah’s bridesmaid I was wearing women’s underwear and had come to prefer it, I was wearing my training skirt, top and shoes about the house, which I now wore without thinking and would do things such as sweep the acres of fabric under me as I sat down, or lift the front as I walked upstairs. Also of my own I had started to wear lipstick and mascara in the evening, for effect I told myself. But the big thing had been going out with Leah and John and nobody making a fuss.
And so after work I had changed and made up, I was idly reading when there was a tap at the window, a ladder appears followed by the window cleaner, he was fast and I was slow, so he saw me on the settee. I was panicking especially when he knocked on the door as he often did to ask for clean water, how could I escape? I just had to deal with him, so I opened the door, took his bucket, paid him and saw him on his way. I was a nervous wreck. An hour later I am retelling the tale to mum who is quite thrilled with this event, just asked if I had her wig on, and had he looked oddly at me, to which I had to say it went far better than I would have expected. Leah teased saying he had poor eyesight if his idea of clean windows was anything to go by.
But this did herald a new phase of my training as I had come to see these events. Over the next week mum left out more things for me to find, or blatantly left things such a ladyshave on the table with a note saying try this. And so by the eve of my next weekend off day I was clean-shaven everywhere, wearing my training outfit plus tights, and with foundation on my face. I felt Saturday was going to be a turning point and so it proved.
Leah lent me some plain black trousers and a fuchsia top, I had my own heels and did my make up as well as I could, which was getting much better, and topped off with the wig I was ready. The reasoning behind the day was to get me over my self-consciousness of being dressed as a woman, so that I go about wearing clothes which were not overtly female, but not my own, so I would not feel awkward about being taken for a woman even when I looked like one.
We went to a big shopping centre and window shopped, stopping for a snack about midday, and then we went to visit a local landmark and walked around the grounds enjoying the views and chatting, eventually sitting on a bench eating ice creams. It had been a quite nice day, and I had to admit I felt less self-conscious when there was no one about, but as the day wore on I was relaxing. So mum felt it to good to stop and said we had not been to the pictures for years and there was a film she fancied. So we ate at pizza hut and then moved onto the cinema. Both places though not heaving were busy enough to get my stress levels up, but I coped and nobody was staring which was helping a lot. The film was a chick flick and they always make my eyes water at the sad parts, mum had to pass me a tissue and remind me not to smudge the make up; things are much easier as a boy. We got home to find Leah and John watching the football round up, but I soon became the centre of attention as they wanted to know where we had been what we had done and how I was feeling. Leah was obviously thrilled by this development and made sure I knew how happy she was.
Next morning mum sat me down for a chat which turned out to be what should happen next. I had my training outfit, one pair of shoes, enough underwear but that was it, if I was to be going out more so I could get used to role I was taking on then I would need more clothes. She even felt it would be good if I were to buy my own which should help me get over my awkward feelings. I was not too sure about that myself. She also pointed out that Leah had been for a fitting of her dress and sometime soon my dress would need sorting out, as it was only three months to the wedding. Fortunately I was working a late so could escape and think these ideas through before I would see them the following evening.
By the following evening I had not only thought things through but acted as well. After work I had called at a clothes supermarket and as casually as I could browsed the racks, till I found some trousers like Leah had lent me, black with a slight flare to the leg, next a white v neck jumper which I liked as it was so soft, last a pair of shoes, they looked like tassel moccasins any man would wear but the tongue was a lot lower than would be expected. I went through the check out without anyone commenting, I could have had groceries for all the concern it caused. I could try them on when I got home and return the next day if wrong. To say mum was smiling from ear to ear with what she saw would be true, I was sent off to try them on and give her a show, and to our amazement they fitted. It was the start of my own wardrobe, and I could tell mum wanted it to get bigger and more varied over the coming weeks. Again I was not so sure, as this one outfit had exhausted me.
I did however start to wear my new outfit about the house, which mum accepted as long as I wore a skirt at least half the days as I was training. She was also becoming keener on the idea that I wore make up every time I wore female clothes, and tried something different or a change of style with the cosmetics. I did not admit it but I was becoming quite involved in seeing how different colours created different effects, from the plain almost no make up look, to the look at me brighter and more pronounced looks. I was also taking far more interest in what other girls wore and hoping to find a style that I hoped might feel right for me when I plucked up courage to buy more clothes.
My next day off was later in the week and I wanted to find out if I could go out alone, so after everyone had gone, I dressed in the trouser outfit and did the face plain pulled on the wig and crept out to my car. I drove out to the country and looked for a nice park I knew off to take a walk. This went well so I went into a town I was familiar with and walked around the shops stopping for a sandwich at lunchtime. Nobody seemed to be taking any more notice of me than if I was dressed more conventionally so I reckoned now might be a good time to buy some more clothes. During my window shopping I had seen and liked these short dress tops that I had seen worn with trousers, I also liked the skirts that were made of really soft fabric so they moved and flowed in a most sensual way. I stuck to the more anonymous big shops, and once again just looked for a size 12 that I liked and took it to the counter to pay.
When mum and Leah came home I was wearing a new black and white dress top, with a new pair of heels, and there were some more bags for them to inspect containing tights, knickers, some make up, and two skirts one a straight denim the other a full circle skirt in the flimsiest material I had felt and being mostly pinks was certainly the most girly thing I had to date.
Having seen my purchases, it occurred to both of them that I was getting more comfortable with my training, so suggested I try some new things over the next week. I agreed to try. First mum bought me new shoes, a pair of 3 ½’ heels with only a strap across the toes, they did look very nice but mum insisted I wore them as much as possible because they would help me gain confidence walking as they are not secure on my feet. She also bought me a satin nightie, encouraging me to wear it at night so as to keep me in the female mood for longer. It took a few nights before I did try it, I was not wanting to give up to much of my male time, but when I did I could immediately feel and see why both of the women in the house wore such night clothes, it was just luxurious to wear and sleep in. and within a week had bought myself another. The last item she introduced was breast forms and a bra. She pointed out the clothes hung better if I was a more correct shape, and so when I was having a dress training time I started to add the bra to my outfits.
I had been training for my bridesmaid role for about two months now and was able to go out on my own, shop on my own, dress and make up on my own. I thought I was pretty much there, but Leah wanted me to do more things that a girl our age would be doing, this meant going out in the evening, Leah really liked dancing and I had been with her before, but to go in a skirt and when she insisted it was the pink one that I felt might revel to much as it floated upwards, she suggested pink knickers, she lent me a white satin top and also insisted on the toe strap sandals. Once more I felt really conspicuous and expressed my reservations, but her enthusiasm was greater than my reluctance and I found myself in town dancing in a club and enjoying myself. Some how she managed to keep the men away, and we just enjoyed each other’s company, it was a special night.
The next time she spoke of a night out she left it until the last minute to tell me that we would not be alone, that John and his friend, who was going to be the best man were coming also. Again her enthusiasm won over and we met first in a bar where John walked in greeted Leah with a kiss then looked at me in my girly pinks and lent over to give me a cheek kiss, I went bright red. Next was Sean he said hello and the whispered to John, John did not whisper his reply.
‘Yes, it’s Alex, Leah’s bro…sister I suppose. Looks great don’t you think?’
Sean did not really reply but was starting to stare and making me uncomfortable, so he was sent to the bar for the next round.
The evening went better than expected Sean stopped staring and relaxed. Then he started chatting freely wanting to know more of how and why I was doing it, and some of how it felt to be presenting as a girl. I tried to be honest and told him of the awkwardness and reservations I had had, and the ones I still had, but as the evening wore on and things got noisier we were having to at first lean closer then sit or stand closer to hear each other, this was the first time I had been quite so close to another man for years, possibly since school days, but the touching was not uncomfortable it was just natural as we were so close anyway. The evening got to loud and we ended up dancing, then to my shock/horror as we parted the engaged couple got into a lengthy parting kiss, while Sean and I chatted, then at the last minute he lent over gave me a kiss, then whispered in my ear.
‘I didn’t know what to expect tonight but it has been great, you look great and if you want we could do it again’ then kissed me again.
‘Oh’ was all I could manage in reply.
On our way home Leah was pumping me for information about my evening, and the kiss. Mum however on hearing about this turn of events went all serious and said that I should consider the implications of playing the role to that extent, I was still a boy and Sean was a boy. I half teasing came back with the argument that if they want me to be relaxed in the female clothes then I have to embrace some of the female life, and girls go out with boys, they started it I was only taking their lead. She ended with a do be careful speech, that is not the normal be careful talk a parent gives either a son or a daughter, but I listened anyway. Then went to bed and my satin nightie. How things had changed.
Despite what might have been happening elsewhere in our lives the wedding and the preparations were looming ever closer, it was time to get the dresses sorted. Leah already had chosen hers, an elegant dress that flowed from the bust in clean lines to the floor with a short train, the bust being supported with a yoke neck. She wanted me in a similar style but no train just to the ankle. With this in mind I was told to dress in a skirt and wear tights and heels. When I had calmed down we made our way to the bridal shop where Leah was getting her dress and introduced me as Alexis, mum would come to the changing room when we had selected a dress to try, I was getting quite nervous about being discovered and I hoped mum would discourage the sales assistant for getting too personal. And so after three attempts we found a dress style that fitted Leah’s expectations, and being in a silk like hers made it more appealing, I was unsure about the pink but everyone commented how well the colour suited me. I had never before considered pink to be my colour, but now apparently it was. With the dress found we had to find shoes, in pink of course. The only ones we found that were near the pink swatch we had were 4” spikes, and when I protested they just told me I would get used to them, my eyes almost popped out of my head at the idea of walking on these stilts. But they were bought and I would have to get used to them. We also found a strapless bra and matching pink knickers. Then almost as an after thought they saw a basque and felt it would be an excellent addition to my outfit, the dress did not need a slim waist but they thought I would like the idea and feel of wearing it under my dress, this also meant stockings of which they bought a few types so I could find out which would suit best. And so ended another mentally exhausting day.
My next day off when at home alone I tried on the new underwear, spending time to work out how they fitted then dressing in the basque, stockings and knickers, put on the new heels and walked about the house, the whole outfit felt very different to anything I had worn before, the basque was tight the stockings straps pulled taut on my arse, and the high heels altered my balance and posture when walking. I did my face then for the first time painted my nails in a frosted pink I found on mum’s table. Now I am not sure why I did not finish dressing but I spent the day reading and watching TV in the underwear, so when mum and Leah came home to find me asleep on the settee wrapped in a satin dressing gown. They had as big a surprise as I did to be found in that state.
After I hurried off to get on a skirt and top nothing was said, but it was clear everyone was thinking about how I was dressed. Leah asked me when alone how they felt, I described them as odd, not sexy she asked, to which I replied not yet. Mum made it clear that the basque was for the wedding, but I would need to wear the shoes about the house, consider it part of the training and familiarisation she said, so I did. But I also bought my own suspender belt and stockings just for the pleasure of wearing them.
For next few weeks I slipped into a more familiarisation routine, I would wear the 4” heels about the house but besides work I wore clothes from my new wardrobe, even if I was going out daytime or evening I would wear skirt or trousers and heels, with my face always made up, and sleeping in one of my selection of nighties was just confirming how far I had gone since first agreeing to be a bridesmaid.
Then a few events happened almost together, first on a whim I had my ears pierced and small studs fitted, this caused one or two comments on the ward. Then I had a series of accidents at work and spilt things down my trousers, and when I did not have a clean pair of my usual work trousers mum suggested my black trousers with the side zip, not for work I protested some one might notice. In the end it was easiest to hope the tunic top would cover the zip and use them for work.
But I had not expected Kay to be so observant, we were in a room alone and she slid a hand over my bum and said how nice the trousers were, they were a good fit and looked comfortable, then she looked rather obviously at my ear studs then picked up a hand and asked if had been wearing nail varnish. I was going to deny everything but I blushed, and she squeezed my hand and said how lovely I was and that a few had commented on how my attitudes had changed as well as my posture and some gestures. I swore her to secrecy and told her everything, at the end she smiled and asked how I felt towards men, I looked shocked, but she carried on and related some gossip about one of the newer doctors who it was said to prefer his partner to be a transvestite. The next thing I know this doctor has noticed my trousers and is chatting with me a little more than usual, then when we are alone he asks if I was free that evening and did I fancy a drink after work, too shocked to be coherent I nodded in some way which he took as a yes and said which pub to meet at. I was stunned by this rapid turn of events, but now had to spend the rest of the shift deciding whether to go or not.
In the end I felt I had nothing to lose and maybe a friend to be made, so I went along still conscious that my trousers had given me away, that maybe piercing my ears had not been the wisest move and that in future I should be more thorough when removing make up and varnish. At nine I walked into a busy bar not far from the hospital and found the Dr Jones or Paul as he preferred to be called waiting with a drink for me, a slim line tonic, how girly I thought, but I sipped it and liked it. We found a corner to sit in and chatted till closing, by which time I had explained why I was wearing women’s trousers and some of the background to how I came to have a pair in the first place. He was taken with the idea of me being a bridesmaid for my sister, and in return he told me how he was gay but preferred his men to be feminine to the point where they passed as women, except when naked. I had done some research into cross dressing but this was a new idea and with Paul sat opposite, a very real one, especially when he suggested that he takes me out to meet some of his friends. I told him I was not gay, but then I did not have a great history as a hetero either, but I would need to think about his offer.
The next time I saw him on the ward I had decided to ask if the offer was still open, when he said yes I asked if he would like me to come as Alex or Alexis, he left the choice up to me, I could dress how I felt most comfortable. I hate it when that happens, you want someone to make the decision for you and they pass it back to you, what should I do?
I had a text chat with Leah about it and she said to go Alexis style. So that evening after finishing mid afternoon I did all the girly things I could think of, showered, shaved, best knickers and bra, ages spent on make up, got the wig just right, then had to decide what to wear, in the end I went careful and wore the trousers and plain top, with the flatter shoes. Paul proved to be a perfect gent, he turned up on time, was polite to mum and then showed me to his car and drove us into town, to a pub I had never heard of but was a nice quiet place that had a mix of ‘ordinary’ customers, some obviously gay and the one cross dresser. Everyone seemed to know everybody else and the atmosphere was very relaxed, Paul kept on introducing me to folk who knew him, and he stuck with the name Alexis, especially after I had reminded him my name was Alex, but he asked me to look in a mirror as no one would believe me, and the cross dresser would get jealous if they knew I was really called Alex. So I let him continue and enjoy himself showing me off. Being the gentleman he bought all my drinks, which were gin and tonics, the choice based on me saying how I had liked the tonic last time, and being honest with gin it was very nice, and after a few I was extremely relaxed. So when one of Paul’s friends came chatting to us and mentioned that it was unusual for Paul to have a girl with him, I must have given the impression that I was a girl and did not want to make him think any different. I was later to realise how well I had passed when I found out that cross dressers and many gays can spot a transvestite with ease.
We had not stayed late, and as Paul dropped me off he asked if I would like to go out again, I said yes I had enjoyed meeting his friends and wanted to see him again.
We left it at that and I went in to be grilled by mum and Leah, who seemed pleased that I was getting even more relaxed in the clothes of a woman. Little did they know I was even becoming relaxed about being in the role of a woman, especially when with Paul.
Nothing happened for several days and I was beginning to think I had imagined the invitation, but Kay had got wind of our meetings and wanted to be kept up to date on developments, it all sounded so girly chatting about dates and boyfriends, I was having trouble at times reminding myself I was Alex.
After 5 days he caught up with me and apologised for being busy, but he was off the day after and I was on an early, he had checked, so pick up half seven, he had a table booked for eight, and he wanted to take Alexis out. Wow what a shock to my male ego, my female image was preferred to the male, well I would just have to do as asked and make sure a presentable Alexis was ready for seven thirty.
I was in a tizzy all shift thinking what to wear, eventually I settled on the pink skirt, the satin top, stockings and after checking it was ok, the pink 4” heels. I even took out my studs for the first time and replaced them with some 2” hoops. I felt great and when Paul arrived he kissed me in front of mum, who did not flinch at the sight. Then it was off to a nice restaurant for a Mexican meal. We chatted about many things, but mostly about work, but his liking for me was clear, and I tried to explain again that I was not gay; though having my hand in his did make it less convincing than I had hoped. We even walked back to the car holding hands, and as he opened my door he caught me and kissed me before allowing me to get inside, my heart was racing and the stomach turning over at these recent events, and when he got in and asked where to next, I asked for the choices, he came up with home, his or mine, a bar, or dancing. I felt a bar then mine, because while I did not want the evening to end, I did want to end up in my bed and not his, as I have said I was not gay. And so we went to a couple of straight bars, then back to mine. Outside I did not invite him in for coffee as Leah was peeping out the window, but did lean over and kiss him as a thank you, saying how much I had enjoyed it and would love to do it again. Which only encouraged him to return the kiss in a more passionate manner which made the knickers material seem totally inadequate for restraining a penis, a fact that did not go unnoticed by either of us.
With six weeks to go, mum took us both for a final fitting of our dresses, I was allowed to wear all the underwear we had bought for the occasion, and could feel myself really enjoying the sensations of being fussed over so I would look really pretty on the day, a feeling I could see mirrored in Leah. Mum even commented how we were behaving like sisters more and more, hardly surprising with all the training I been doing, but we were having a lovely girl time. When she suggested going out that evening I contacted Paul to see if he was free, when he said he could be, I told him to make certain he was as I needed a partner to stop men from chatting me up, his parting comment was, do I want a chaperone or a partner.
Leah lent me a neat red mini dress, and made sure I was ready well before John or Paul turned up, then we had a taxi pick us up and take us into town. Leah seemed to corner Paul at every opportunity, until John made it clear she was with him, Paul copied by taking my hand and leading me into a club where we spent the night unable to talk just dance or let your bodies do the talking. At 2 am we found a taxi and went home, John was stopping over but Paul took the taxi to his own house, and said he would collect his car in the morning.
In the morning, slowly Leah, John and I made our way downstairs, John was shocked to find that I slept in a sexy nightie and gave me a most peculiar look as I sat down to drink my coffee. I ignored it as the nightie felt so luxurious I doubted if cotton pyjamas would ever find their way into my bed again. I decided that I would drive over to Paul’s to pick him up so he could retrieve his car, and also to get a look at his house without it being at the end of the evening. I surprised myself at how good I was getting at being ready; I took 30 minutes from going for a shower to stepping out to my car. I was only in trousers and a top, but the make up and hair had all been done properly.
Paul had a nice house in town, very neat and tastefully decorated, it was definitely a man’s home, as opposed to mine that was dominated by women and most of it reflected their tastes. After a polite coffee, he asked if I wanted to stay for lunch, I agreed as Leah, John and mum were doing wedding preparations, which I was needed for and but did not wish to be involved in, so I stayed. Then we watched some film on video, fell asleep on the couch together. I woke to find my head in Paul’s lap the film nearly over and Paul gently caressing me. This felt so special that I let him continue, then moved a hand around his neck and pulled his face down to mine. As you can expect this was not too comfortable or successful, so I rolled over to face him and pulled myself up to make things easier. For the first time we allowed ourselves to just be overwhelmed by the passion. We kissed and cuddled and fondled, and when we started petting, he told me how it was a shame I was not dressed like the night we had our meal together, I looked puzzled, stockings and a skirt he replied, so I asked what he had in mind, and said anything I wanted, he did not wish to push me as I was not gay. For that he got a playful thump, which he caught and pulled me to him. His erection was obvious; the tight trousers restrained mine, so when I put my hand on his he could not get much of a feel at mine, which I was glad about. We continued enjoying ourselves getting more aroused until I put my hand inside his pants a gently massaged him till he came in my hand. As he gasped for breath I calmed down realising I had his sticky semen on my hand and what on earth was I doing playing with another mans dick. I got up to clean myself at the sink, and as I washed he came behind and cuddled me, saying how lovely it had been, and how lovely I was. Far to many firsts for one day I thought and how many more firsts would I have if I stayed with Paul. He kissed me on the neck and told how he thought we made a good couple and hoped I did too. I said needed time to think and gather myself, this was all to new for me, exciting yes, but none the less quite different from what I had thought would be my choice of relationship some months ago. He accepted that and we decided that we should take him for his car, I knew this would mean him meeting mum properly, but I felt it was probably the right time to do it.
That night I had a troubled sleep, I would wake thinking of me and Paul being together and doing various things, some mundane others quite erotic, but always I was in a lovely skirt or dress floating around me like on the cover of a romantic novel. He had got me and I knew I would have to see where it took me, to stop it now would leave so many unanswered questions and opportunities I was sure to feel regretting later.
Of course I did not tell him any of this, or Leah come to think of it, this was to personal and to shocking to go public with, I was only supposed to be pretending to be a girl, not actually behaving like one. Kay guessed at some of my feelings when she asked about my evening out, but was kind enough not to voice them.
Anyway I had to find a way of preserving my modesty when things got hot, and after some internet reading came up with control briefs, not too sexy but practical in a Bridget Jones way. Then I found a G-string control panty which though not silky sexy were somewhat more appealing. I found myself planning what I should wear next time we went out, it really just revolved around the pink soft skirt and stockings.
So I made my plans for my next day off, I found out what he was working, and asked if I could cook him a meal for when he got home. He did not ask any questions just gave me a key and said he should be finished about eight that day. So I spent my morning preparing myself, then in daytime clothes I went shopping, and added the groceries to the bag of clothes I had packed into the car before. Next I went to Paul’s and did some food prep, then went to his room to get ready, I had a nosy around as well, it was all male stuff and seemed to be only him living there, but I also found condoms and some lubricant cream, and my mind went into imaginings and possibilities that I was thinking might happen.
At a little after eight I was truly ready, I was in the basque, with stockings, the pink heels, my sexiest top, of course the ink skirt, sultry make up and possibly too much perfume. There was also a part drunk bottle of wine that I had started after I had finished getting ready. He just smiled as I offered him a glass and kissed him saying welcome home dear, then he put a hand on my arse which I am sure was to confirm that I indeed in stockings. We ate a lovely pasta meal, and drank more wine. As the evening passed we relaxed with the wine, until we were kissing passionately again, only this time his hands were feeling me all over, and as I got more excited I felt for his dick and unzipped his fly, then to my surprise as well as his I think, I kissed it, he held my head as he controlled my kissing until I wrapped my lips around his helmet and licked, then sucked, then slid my lips up and down, next I found myself suckling his end, and from his breathing and his grip on my head I knew I should let go soon or get a sticky mouthful. I tried to let go but he was holding me, and something in me wanted to suck harder. And then he came, I nearly gagged, but as he let go of my head I continued to lick his softening erection. Not only was this my first blow job, giving or recieving, it was my first intimate experience sexually, and I knew that was significant. I kissed him so he could taste the semen on my tongue, then I had more wine to wash the taste away.
It was getting late and I had drunk too much to drive, so when he offered to call a taxi, I kissed him again and asked why when we neither of us had to be up early for work, and asked if I could stop the night. This created a shocked smile, and a quick yes. I excused myself and went upstairs found my short silk nightie that I had packed, and then when I heard him coming stepped onto the landing, his eyes almost popped out his head as he put his arms around my waist,
‘I was going to offer you the spare bed, but I don’t think that is necessary, do you?’
I stuck my tongue down his throat and a hand down his trousers; I could still feel the excitement from before and wanted to feel that explosion and afterglow I had seen on Paul. So I started undressing him, his shirt, then his trousers, then as he was recovering his erection I removed his boxers. Soon we were on the bed and writhing around kissing and I felt his dick press against my arse crack, the g-string was in the way, but I immediately knew I wanted to find out what it would feel like to be fucked, so as casually as I could pulled a condom and the cream from under the pillow where I had hidden them earlier, I did not need to ask, he just covered himself, then pulled the string to one side and applied the cream, then it was back to passion until I asked how he wanted me, and let him pull my legs up and start pressing his dick into my arse, he was very gentle at first, then as I felt him go inside and push deeper, I was feeling a sense of total enjoyment, as he got deeper so the thrusts got harder and despite the pain I just felt the pressure building inside me, until I exploded, my panties were soaked, and within two strokes he had come inside me. My first sex and it was brilliant, but exhausting. I managed to change my panties and clean up before falling fast asleep alongside Paul. What a day, and again I had to think what was happening to me, I was supposed to be just doing it as a game to please Leah, now look at me, but I was asleep before I could answer it.
Next morning I had to think about work, but my first thoughts were about how sore my arse still was, followed by the lasting image of being in bed with Paul, then rethinking the 'what am I doing here' thoughts although they subsided a bit when he turned over and gave me a cuddle. In my overnight bag I had my clothes for work, put on the side zip trousers thinking I don’t care if anyone notices the last 24 hours have confirmed to me that I am not a regular man anymore.
When mum and Leah finally caught up with me after work mum was asking how I was and did I have good day the day before, I had told her I was spending it with friends but not specific about who, but was more interested that I had gone to work in my Alexis trousers when I had clean Alex trousers. Leah being more aware wanted to know how Paul had been, she had been in my room I guess and worked out what clothes were gone and therefore guessed that I was doing some extra training. She was right in a way, I was getting more used to the role of being treated like a woman.
Nothing much happened for a week, mum did buy me another pair of trousers, I bought some more control pants and another pair of shoes, black courts with a 3” wedge that I happened to see as I passed a shop window. Even without make up I was having no qualms about buying stuff, I had answers if I was ever asked but no one did, they just took my money.
I could not get Paul out my daydreams or sleep dreams, but did not want to appear to keen, so waited for him to call me. He was working on a different ward now so it was not common to meet at work, but we met in the canteen and had our lunch together, we both expressed how we both felt awkward with the situation, he did not wish to influence or rush me into something I might regret, and I did not have a clue what was happening really, and all said in whispers or in a code so those around hopefully would not pick up on what we were discussing. He wanted to continue as friends and if I wanted to be his girlfriend even better, to which I responded by saying I wanted to go back to the bar he took me to at first, and so the date was set up.
Kay however was not surprised, she noticed the trousers and my uneasy walk after my night out, and immediately asked how it had been. I went vaguely around the answers but she just added to them and concluded I had had a good night.
Before I meet Paul the next time I had a chat with mum and Leah about what else I needed to get used to or have done before the wedding. Besides some last minute things such as getting it all together for the big day, they felt I was about as ready as I ever would be and how well I had embraced the whole bridesmaid thing. Leah did quietly on our own suggest I thin my eyebrows, I had read about this weeks before and stray hairs had already gone, so I started to pluck a few extras out so the thinning was not a suddenly dramatic change.
Then when I met Paul I asked him the same question, and he being more knowledgeable about cross dressing suggested I try gluing the silicone breasts on, asked if I had ever tried long nails or lip plumping lipsticks. I could not do long nails because of work, but glue on would an option, as for the others I had no real idea about. We had a lovely evening together chatting with his friends; I was beginning to feel really comfortable in my female clothes and could talk freely without feeling I was odd, and made several new friends. As we drove home I was struck by how much I enjoyed being Paul’s girlfriend, but did not know how to say it, so relied on a passionate kiss to relay my feelings, and ask when would I see him again.
My next early shift coincided with Sally the travelling hairdresser who made a regular call to do mum and Leah’s hair, and mine if I was in, in the past it was just a trim, but Leah was chatting about weddings and what Sally had in the way of ideas for her hair. Then they got onto bridesmaids and would Sally being doing them as well, Leah smirked then giggled which Sally did not understand, until I walked into the room in a fairly androgynous trousers and jumper and Leah said that she would certainly be doing the bridesmaid, Sally took a moment to connect the facts then her mouth hit the floor.
‘Alex?’
‘Yes’
‘Wow!’
This was followed by the explanation of why and how I was going to be a bridesmaid, at the end Sally announced that this would make a big difference to how she cut my hair, and then as she did, mum was talking of possibilities. My hair had become quite long as it had missed out on a cut for many months, so Sally wanted to try a cut before we went for a wig. She cut it level with my collar and cut the fringe so it swept back, I was already tucking it behind my ears, but now I would need to gel it to hopefully keep it back. Then they talked about colours and highlights that lost me.
It was at work next morning Kay noticed the new cut, but then everyone notices a new cut even if it is just a trim, but later in the day the ward sister suggested I use bobby pins to hold the fringe back, I blushed and asked what she meant, so she explained how if I was going to have a girl cut then I might as well use girl things to control it, followed with a, by the way go and check your face in a mirror. I shot off to the toilet and to my horror I still had mascara on, not heavy but noticeable, I was mortified when she followed me in and apologised, she had only meant it as a tease and was fine with it as long as I was, and told me how much better I had been over the last few months. I asked what she thought and was very supportive, but did say that one or two were not, but I had caused some minor gossip with my changing ways and looks.
So that was it I was rumbled at work, I then realised I did not have to be so male when at work and could allow myself to let some female things overlap more, I could wear my female cut trousers when I wanted, could actually wear some small make up like the women if I wanted, even wear the black moccasins, things were changing.
Things changed even more the next time I had rest days, I had two together with an early before, so Paul asked me to go around after work, he had something to show me. I rolled up late afternoon with a bag of clothes to change into if he wanted to go out, but what he had for me left me with odd feelings. He had got hold of some surgical glue and explained how to attach my breasts, this felt weird enough, but then he had got a gaff of the internet that was supposed to be brilliant, he had read the instructions and wanted me to try it on then. It only looked like a tube with two tails and wondered how it could possibly work. So with a doctors hands he asked me to drop my pants, then slide the tube over my penis, then with a hairdryer warmed it up, the tube shrank around my penis, the tails were then glued to either side of my arse crack. Paul lead me to his long mirror, I was amazed, at a distance I looked all woman. I spun round to thank him and give him a kiss, we cuddled for a moment and I realised the gaff was going to stop any erections as I could not swell anymore. I mentioned this and had he thought about it, he apologised for not thinking of it through, but said 'well do you really want me to use that, when we both know the best is when I fuck you.' I made no response except to pull his groin to mine and kiss him till I felt his erection grow, then it was not long before we were on the bed enjoying a very intimate moment.
After we had recovered he suggested shopping for a few extras so I could spend my days off with everything still in place. Later that evening I drove home with the appliances still glued on, but with new long thin ear rings, lips enhanced with a stinging solution that made them swell a bit and long glue on finger nails painted the same pink as my lips. I also had a wrist full of bangles that made me conscious of them and my new image. I also had a packet of hair colouring that I wanted to ask Leah’s advice about before using in case I ruined my hair before the wedding. She thought I would look good with lighter hair so follow the instructions and I would look great she encouraged.
That night was not the most comfortable, I wore a bra to support the boobs, but as well as that the groin was definitely different and the nails were taking some adjusting too. But next morning I did my hair and was really pleased with the results as my mousy hair lightened and seemed to gain more shine. I then played with some bobby pins and gel to see what styles I could create, then as I dried it for the last time I plucked my eyebrows more severely than before. All this combined with the adjustments I was required to make because of the longer nails made for a most amusing morning.
Next on my list of things to do was to get back into the silky panties, but now I had matching bras to consider I felt I would need to get some shopping done. So I left the house, went and shopped for underwear and a new outfit, pink again, but a fluffy jumper with a black mini kilt. Next stop was the pub Paul had taken me to, I wanted to see what it was like on my own, but daytime it was completely different, the atmosphere and mix of people was very different, but the staff recognised me and made me feel welcome. So after a drink and a bite to eat I thought about the rest of my plans. I did a grocery shop then went to Paul’s to surprise him with an evening meal. To say the meal went down well would be an understatement, but it was nothing compared to the antics Paul got up to later, leaving me exhausted, sore and thoroughly happy as I once again fell asleep alongside a man, even I was beginning to doubt if I was not gay.
Paul thought the new look was excellent; he even made the comment that now there was no doubt which of us was on top as it were seeing as I would not be using mine. I was still enjoying being the bottom, but did think about the idea of one day being on top as I rode his erection.
The next day he wanted to treat me, he loved the new mini, but he wanted to buy me a classy outfit, so he ‘forced’ me to go shopping. By mid afternoon I was getting tired, I had teetered about on my heels for him, overcome my fear of changing rooms and was now carrying bags containing a halter neck top with a full length straight shirt and a pair of 4” sandals, of course all in pink. He insisted I change when we got back, told me I looked stunning and that we were going out for a meal, all I had to do was freshen up the make up and wrap a white pashmina around my shoulders to be ready. Paul was most impressed and took me to a smart place, where the food and service were excellent, but not as good as the service he got when we arrived back at his for a coffee. I was becoming addicted to sex with this man and enjoying it all.
But all good things come to an end, next morning I had to unglue the boobs, clean off the nails, and try to make myself look half descent for work. I did however leave my toenails pink, and the gaff was firmly and secretly in place. Kay was smiling when she saw my new hair colour, and told me it suited me, then commented on the flat front to my trousers, then my thin brows, then asked if I had had a couple of days off. I refused to give straight answers, but she just told me everyone now knew I was at least gay and maybe into cross dressing. When I asked does it matter, she said it made no difference it her, and she preferred the new me. And I wondered if one day I might just be brave enough to let her meet Alexis.
When I got home it was the first time Leah and mum had seen my new hair colour and brows, both liked it and asked if I had any more things I was going to try before the wedding, so I told them about the glue for the boobs, and how I had worn long nails for two days, then how Paul had found a thing which gave me a flat front between the legs, but only Leah was cheeky enough to want a look. She was suitably impressed with the hidden male bits, and asked if she could have another look when I did the full works next time.
The wedding was almost upon us, the dress had been collected after the minor alterations, John had been out and got his new suit, mum had a new outfit and things were getting tense. Paul was becoming my escape and finding in each other a closeness that both appreciated. One problem that had lurked all through this planning and training was how would the family take to me being in a bridesmaids dress. So mum was given the job of casually letting all the family know that Leah had persuaded me to keep a childhood promise, and that it meant nothing other than sibling fun. I was not going to tell her she was wrong, and that she had let a genie out of the box that was not for going back in. but she must have been ignoring the presence of Paul and his obvious affection for me when he was at the house.
A week before the wedding I was on holiday and I spent my first day getting every aspect of Alex hidden. The original gaff had let go so a replacement was fitted, my chest was enhanced, fingernails had the glue on extensions, my brows had a final plucking, and the lips were brushed with the stimulating liquid that made them swell. Then in my black mini, pink top and a jacket I went to see Sally for a hair appointment. She had discussed with Leah what style I was to have but Leah would not tell me and Sally refused to tell me either just told me I had to wait. When I got there she also told me to remove the glue on nails; I was going to be having acrylics that are far tougher and dont become detached unexpectedly. So I sat back and had to take whatever was planned. To explain all she did would be even more tedious than this tale already is, but I walked out of her place in the late afternoon with long hair courtesy of extensions, with highlights which lightened the overall colour more than before, and my double length nails were a gentle pink. I felt truly gorgeous as the hair caressed my face and neck.
Leah was off as well, so when she meet me late on she was suitably impressed as I walked towards her, in my 4” heels, the mini kilt flicking out as I moved, my chest moving in a rather bouncy manner, but most of all the hair blowing in the breeze. As we greeted she whispered that I was born to be Alexis really, when she saw me now it confirmed her feelings, I thanked her, linked arms, and pointed out 'if that was the case' then ‘sister’ we had some boys to meet.
It was only John and Sean to run through the wedding plans, but Sean had not seen me for months since my first outing to a bar, and now when he saw me he was shocked how much I had changed, he just could not accept I was ever Alex because I was looking so beautiful. I do love the compliments. He also got confused when I explained that I was gay, he somehow thought I meant I was lesbian, but told him how Paul was a man, this did make him back off, whether he was not happy with a gay or he did not want to waste energy chasing a taken bit of skirt, I did not work that one out. But he was very kind and polite, and left as friends knowing we were going to be looking after the happy couple in a week and it was best we get along.
Mum was a little less enthusiastic about my new look, she had thought I would be more androgynous the week before, so if I met family they would not think I was so heavily into the looking the part as I had become. I went and changed into some jeans and a shirt, pulled my hair back, and slipped on trainers, and after a wash went to see how she thought I might get away with being a boy. She was struggling with the fact that she had encouraged me to take up this challenge, and that now she saw a mainly female person, yes I was in Alex clothes but my face had narrow brows, plumper lips, my fingernails were still extended, but most obvious was my chest carrying two C cup breasts that did not flatten. She had to accept I really did find it easier to pass as a girl than a man. Her face was saved by an aunt deciding at the last minute that she could make the wedding, but at short notice she was having trouble finding a hotel nearby, so mum came up with the idea that I stay at Paul’s, while the aunt has my room. Paul was wonderful saying yes without a pause, and so I spent the evening packing all my new clothes, leaving anything male in the bedroom, I was not working so I could be Alexis till the aunt left.
A week with Paul meant several things, one was being able to come and go without any thought of neighbours gossiping because I would always be female to them. Another was the thrill of being able to dress up every day just how I now wanted too. But probably the best was being able to spend time with Paul. I enjoyed cooking for him, keeping the house tidy and being the sexy plaything that he always wanted. We had a week and made the most of it, at least once a day I once fucked, but I was also blowing him, the funniest being when he was stood up using the phone and I got him so excited he had to make excuses for his breathing becoming laboured. I also got to ride on top, which was something I wanted to do after he had referred to me as his bottom, so it was nice to have him on the bottom for a change, if not the bottom in the relationship.
Mum came to visit and make sure I was coping without her, and fortunately did not catch us doing anything she might disapprove of, or me wearing anything that would give the wrong impression of her boy just dressing up for his sister.
The Thursday evening was great fun, I was invited on the hen night, there were a few girls I knew, but the majority I only knew by name and I just blended in as one of the girls, getting drunk, chatting up boys and being silly.
Then on Saturday mum was in full organising mode. I had to be there early, Sally was doing hair, and then a girl called Yvonne was doing make up. Mum went first, then me then Leah, so mum helped me into my dress and got a proper eyeful of all the add ons I had attached to me. Then with me dressed we both dressed Leah and were ready in good time for a glass of champagne before the wedding car arrived. The aunt had been great at running around making drinks and stopping mum getting to flustered. So once in the car mum calmed down as we rode.
I know Leah’s dress was wonderful, but I could not help enjoying the feel of my dress, with the underwear and the luxurious fabrics I was having trouble not thinking this was my day and not Leah’s. The ceremony went off with a hitch, and then at the reception we stood to welcome the guests, many female relatives being complimentary about how I looked, later coming to chat about how I had got myself into the situation and asking how had I got to look so convincing, most men I sensed keeping their distance not sure what to make of me, but a few did relax later and come to talk. The most awkward time was when the dancing started, Leah and John got up to start, and Steve was expected to follow with me, while he had been fine with me previously now he felt everyone was watching him and saying that it was two men dancing, that’s not right. But we did the one dance and I let him go and relax. I did get asked to dance by several women though which was odd, because no one ever asked Alex to dance, male or female.
It had been an interesting day but it had been without Paul who had not been able to get out of work, but he promised to pick me up at the end and take me back to his house. The dress was still feeling great even at 1 am. But it was much later before I was fully undressed, he helped me out of the dress to find basque and stockings on top of pink spikes, I knew I was his wet dream and played with him for ages before finally letting him come, then as I got him erect again I asked if he ever thought of Alexis as permanent part of his life, he said he did , so asked if he wanted me to leave, he said no, so I pushed again asking if that meant he wanted me to stay, of course it did I was welcome to stay as long as I wanted.
‘Pardon’ I asked
‘Yes, I want you to stay’
‘Sure?’
‘Off course I am’
‘Why?’
‘Because I love you’
I guided his erection into me,
‘I love you too, and now that is sorted I need you to finish off one randy bridesmaid, please’
‘Most certainly my darling Alexis’
I am sure we all know of at least one, the energetic little old lady who can get you to do almost anything because it is for a good cause and you just can't look her in the eye and say no.
One such lady lives near me, she has this sweet charming image, but underneath I suspect is a cunning schemer. She arrives at your door, you open it innocently and she 'reminds' you that the event will start later that evening, 'Don't be late'. Your partner/wife apparently had agreed to your participation and it would be hard for everyone else if you failed to help. You are trapped, your forgetful other half has said you would do whatever some weeks ago, and besides there is this sweet little old lady stood in front of you asking ever so nicely to come along. The only result is that you turn up at the community centre having had words with your better half about agreeing to things on your behalf, and not passing on the information, no matter how uncomfortable.
Come 7.30, five of us are sitting in the community centre waiting for Edith to turn up, she is doing another fund raising event, it could be 'save smallpox from extinction' the cause does not really matter, this time she wants to raise money to improve the kids playground and give some to the latest disaster created by man or nature, I think it was Haiti this time. The other four men I knew at least by sight, two were previous victims and we commiserated on our plight, after a few minutes I realised we were all of a similar build. Thin, not too tall, later I recognised clean shaven, small feet and hands that hardly knew manual work. We were getting restless when Edith and her bossier friend Margaret appeared, with her warmth and charm, the growing dissention suddenly evaporated and we were unable to object. Our little old lady had got an idea that she thought would be good fun, a great laugh, and a good money spinner. When she started to explain all five of us were clearly uneasy with her idea and failed to share her enthusiasm.
What she had in mind was a fashion show, initially her group had thought of doing it like previous events by getting some younger women to model for the clothes provider. This time they had come up with the 'fun' idea of having some suitable 'male' models. I have no idea why this would help sell dresses but the provider apparently had gone along with the idea, even suggesting how our group could make the most of the situation. It was clear none of us were keen, or at least able to show we were keen even if we were, some raised objections such as 'I might be working that date', but we all said we would need to check with our wife/partner before we committed to her daft idea. At this she smiled ever so sweetly, she already knew we were sunk, my wife already knew as I was to find out not very much later that evening. As a parting gift she gave us all a bag, each contained a pair of shoes, she was well prepared, having found out our shoes size and borrowed shoes for us, was she so confident that we would turn up and then agree that she would have the shoes beforehand. She explained that we should go home and practice walking in them as they are quite different to flat men's shoes. I think we said 'oh?' in a defeated sort of way.
We separated soon after, a talk at the door between the men left us in little doubt that no matter how much we might say 'no way' come the next meeting we would all be there, we had no choice in the face of such tough opposition, namely Edith the sweet old lady.
I got home shortly after, as I asked Helen why she had suggested I would do this event, she changed the subject around to what was in the bag, 'oh black courts, and not to high, not even 3". I was now feeling deflated, she was not going to be my get out of jail card, especially when she suggested I try them on straight away, 'you will need all the practice you can get' she encouraged.
'Do I have any choice?' I lamely asked
'Not really, just like you I could not say no, so we might as well get used to the idea of you being a model and make the most of it. And remember the better you are the more clothes get sold, the more tickets we sell and the more money we raise.'
'But'
'There are no buts, only when, and that is in three weeks, so come on we can do this' and with that we hugged before I changed my footwear and prepared to be humiliated.
It was a most peculiar sensation walking on the high heels, at first I staggered about a little but in a short time I was getting around the house quite comfortably. I noticed a few things that the heels did to me though, I would walk with more purpose making the steps follow a line as it were, this tight rope walking made me hold my arms and upper body differently as I controlled my balance. Then there was the stairs, going up is easy, just use the toes, but going down took more care as I had to get the whole foot on a tread and the angle of my foot was tilting my forward and potentially down. Sitting was also different, at the table I would normally put my feet flat on the floor, the heels did not make that impossible, it just became easier to put the feet under the chair with only the toes on the floor, often tucked around the chair legs. The easy chair which was a lounging back and relax position proved to hard, I could not get my toes anywhere near the floor, the heels resting on the backs, I had to sit with my feet flat which pushed my knees forward, which brought my body forward, which meant I sat more upright with a cushion behind me, or I tucked my feet beneath me like Helen did. I once complained about the height which got a swift rebuttal from Helen 'those are quite low, you should try some of the real high heels with the spike heels, then you would have something to moan about' I shut up and just wore the shoes in the evening without comment after that.
A week later the five of us plus Edith and Margaret were in the hall, she said she was pleased to see us all back again, more like surprised Max said. I had to agree that all five of us had not got the guts to back out was the surprise, I thought one might find an excuse. The purpose of this meeting was to run through what Edith was planning and what she wanted us to actually do. First the detail of how the show would work, a changing room was chosen, then we went through walking out onto the stage doing a walk and twirl then back to the side room. We had a go at this to see if we might have problems with getting in each others way. This was all done quite clinically so it ironed out potential hiccups. Then a sit down as Edith explained how we would each have five changes of outfit, a business style, daytime, summer, (it was easter) evening and holiday. We would have our partners to help with the changes, which would save our blushes she thought, but was a good idea as we were novices at this whole thing.
With the talk over, the five of us left Edith to discuss things with Margaret while Max, Jason and myself went for a drink on the way home. We were all speaking quietly not wishing our activities to be broadcast, but we all seemed agreed that the shoes were weird, but the idea was a good one and should be a lot of fun. We also noticed that Sam had been very quiet and made up reasons for this, ranging from a hidden passion for cross dressing to outright fear. Personally I thought Jason was enjoying it a little too much, but then I had not been kicking up a great fuss actually slipping my heels on at home instead of my slippers when I went through the door.
For me I had a busy week of working, leaving little time for considering what was going to happen over the next few weeks. Edith and her helpers were apparently busy selling tickets, and according to Helen, doing quite well. I did notice some changes in Helen's behaviour though, she was noticeably more affectionate, particularly when I was wearing the heels using comments like 'nice legs' and 'sexy walk' even complimenting my arse wiggle. When she was making such remarks it was usually linked to times of intimate affection, which unsurprisingly encouraged me to walk with a sexier walk, putting more wiggle into the steps.
For our next rehearsal Edith asked us to bring our shoes, Margaret came into her own now as she controlled the proceedings. She asked us to walk on the stage in our heels, then run through a mock change to see how we managed to get from stage to changing room. She was giving advice to us all on how to hold ourselves, place our feet and most commonly, not to look at our feet. Later in the evening Elle, the owner of the shop which was supplying the clothes, came to see us. She wanted to check out who was going to be modelling her merchandise and work out which outfits would look best on which model. This was going quite well for me as I had got the hang of the shoes. The big shock came as we were packing up to leave and we all received a bag and some instructions. By the next rehearsal we needed to have got ourselves a bra with some padding, a couple of pairs of tights, skin coloured, and most shocking was the instruction to shave our legs and arms, with a rider of, possibly best if we use the same method our partners use. If they use cream we use cream etc. Jason paled noticeably, we later learnt that his wife waxes and we all knew stories of how painful that can be.
As before we went for a pint on the way home, discussing how we saw the event going, even a little talk of how we felt. This time all five of us were there. I tried to judge how each of us were handling this situation, Jason was still shocked with the threat of waxing, but he had got the walking in heels of quite well. Max always joking had not really got the poise on heels but was playing it for fun. Sam was rather none committal, clearly not having tried the walking but seemed to be fine with the idea. Paul was possibly the weakest, he was not happy for some reason, clearly he had practiced in the shoes, but his body language said he did not want to be doing this, but his wife was frightening character so he really had to do it because she said he would, and that was it. For me, I was finding it fun so far, the heels had been interesting and I was looking forward to finding out how my skin would feel without the hair, Helen's felt nice and smooth, I wondered if mine would be as nice.
When I got home Helen wanted a full debrief on what had happened. While I talked she examined the pants in the bag, 'control briefs' she commented 'keep your manly bump hidden I guess'. Then she suggested we get the hair job done striaght away, seeing no reason not too I was soon naked in the shower while Helen spread some cream over my skin, after a few minutes I mentioned it was starting to tingle, a few minutes later I was rinsing all my body hair down the plug hole, Helen then asked me to stand still and produced a razor which she carefully used to trim my pubic hairs with, producing what she called a bikini. I first noticed how sensitive my skin was as I dried myself, but what followed was very nice, she massaged miostuiser into my hair free body which was a most sensual prelude to some very nice sex. When asked if I was having any problems with the modelling, I replied that I could not see any downsides yet. But at the time Helen was massaging my erection while I was fingering her hole, an unfair time to ask such a loaded question really.
That was Friday night, so come Saturday morning and the weekend ahead of us, she suggested I try on the briefs 'to make sure they fit'. They were certainly not a loose fit, I managed to wrestle my way into them, then position all my extra male bits so as they did not hurt. This was a shock to my male ego as I was so used to looking down and seeing the familiar bulge that I had taken for granted, it was now gone. But there was more to come, Helen gave me one of her bras to see if it fitted, with a little adjusting she was happy with the outcome. I was less pleased as I now had bumps in unfamiliar places, even if they were just knickers stuffed into the cups. The last thing to try on was tights, this was nothing like long socks I discovered, and after some guidance I was pulling them up around my waist, and whilst the other items had shocked me in some way, the sensation of the hose was very pleasant, Helen assured me it was the smooth skin. I agreed as I had nothing to compare it with.
That session over we still had to get on with usual weekend stuff, shopping and cleaning, so I went to remove the female items, Helen stroking my covered leg suggested I leave them on, she would do the shopping while I stopped at home and did the cleaning, then adding that maybe I could wear a dress so I became aware of how I might feel in advance of my modelling debut. This all seemed a little unnecessary but she reminded me I had not seen any downside yet, I did say it would stop me going outdoors, fine she said, she would empty the bins later. And so I dusted and hoovered then mopped in heels and a dress for the first time. The skirt part of the dress took some getting used to, it seemed to get in the way unlike trousers ever did, but by the time Helen returned I was quite proficient, I even had the sitting down sweep under me routine worked out. Asking how the morning had been I said ok, good she replied as she needed to take me shopping for a few items that we did not have. So as not to freak me out she declined to say what, but later that day dressed as a man we bought a foundation cream that suited my skin colour, I have to say it was a nerve wracking time and was happy to be outside once we had our purchase.
Fortunately the rest of the weekend was taken up with watching sport and visiting family so we did not venture any further into my feminine side as Helen called it. I did at her suggestion wear the pants on Sunday 'so I got used to them' being the reason, and as I was only spectating there would be no chance of being seen.
There was one more rehearsal before the show, Edith wanted have a run through so our partners knew what was happening as well. They would be our dressers, so needed to be aware of how things would work. This proved an interesting time to watch the other couples. Paul was now good on his heels and his wife was definitely in charge telling him what to do and how to behave. Max was having a great time joking about with his partner as they got on with the business in hand. Sam seemed to still not be enjoying himself greatly, though his wife was, and Jason clearly was having some fun, I asked him about the waxing, he admitted to the pain, but also admitted to liking the smooth skin. I thought that maybe he had had a similiar time to myself, post hair removal, but did not like to ask. When we got home later I was to find out Helen had no such limits, with her and Sally comparing notes about me and Jason, and yes they had an erotic time soothing Jason's sore skin.
We paraded around, the wives did our faces so Edith and Elle knew what to expect, we did a couple of changes using our own clothes to get an idea of timings. Then it was all over, we should get there early the following evening so we can be ready and get sorted. Elle and Edith had plenty of notes which they said they would take care of. We left being told to come in our underwear and with the make up we would need, and that was it. Having Helen there I was not sure about the pub, but we went anyway. Just Jason, Max and myself plus other halves went for a drink. The only topic was dressing, the women all bitched about Paul's wife being overbearing and how Paul was under the thumb, they even suggested they were into S & M and she had a black leather catsuit at home and made him kneel at her feet. Sam's wife they decided was using him as a doll to dress up, she was very girlie but was clearly enjoying the experience more than Sam, perhaps she wanted to be a model and was living her dream through him, who knows. This being bitchy and gossipping was fun, but when they turned on us we squirmed, Sally told everyone how nice Jason's skin was now, and when Helen said something similiar I blushed, 'just like a girl' they said. Even Max lost his bravado when his wife Jenny suggested he would suit red and with his legs a mini skirt would be a must. This was mostly good humoured fun, but I was still happy to be on my way home and take the oppurtunity to get some rest.
I had a disturbed night, might have been the sheets on my smooth skin, or maybe it was the satin nightie Helen had taken to wearing at night and was brushing my sensitive skin, or maybe it was just the dread of what I was letting myself in for the following evening.
We turned up at the hall in plenty of time, Elle had brought the clothes and hung them on rails, divided so we all knew which were ours, Paul was already there and made up, I arrived with Jason and half an hour later we too were looking surpisingly female. Margaret had borrowed wigs from a dramatic group and with Elle's help had decided who was blonde, short, dark, long etc. I was a long straight blonde, something Helen approved of. By seven we were all made up and wearing our first outfit, which was business styles. I had a fitted grey skirt suit with a silk blouse, the others were similiarly dressed making us look like a group of business execs, well so Sally reckoned.
We all did some pacing around, though it is not the same in heels. Then Elle was introduced on stage and a little chat about how the models were different tonight, everyone laughed, it had become general knowledge that men were doing the modelling, and Elle's spin on it was 'If it looks good on these models, how much better will it look on you ladies?'
Jason went first, we all watched from the wings as he strode out, did a turn, posed, then walked off when Elle had finished telling the audience how wonderful the outfit was. Then Max, who played it up with plenty of camp gestures, next me, I tried to play it straight, a female look so a female walk and pose, I think it worked I got clapped anyway. Then it was off to see Helen and change. The room was already in chaos, but Helen took me and helped me undress then helped me into a short summer dress that hardly covered my pants. Then it was back to the stage, parade and back. A knitted dress followed that. Next was a long flowing dress which was described as a holiday look. Last a black lycra dress, mid thigh hem with bare arms and shoulders, save for the transparent blouse I wore as a jacket that would have looked sexy on Helen, but on me I doubted. As a finale we all went on stage in our evening wear, to get our applause, then it was off to get changed one last time. This was the first time I noticed what the others were wearing and we were all different, Jason had a long satin gown on, Max was in a high necked red silk dress, Paul was in a loose satin all in one 'boiler suit' for want of a better description, and Sam was in the shortest skirt pulling tightly across his thankfully flat grion with a top so loose I wondered how it did not slide of his shoulders. As I looked around I had to admit we did actually appear to be five presentable women, which I would have been happy to take out. But I knew the truth so would not be inviting any of them out soon.
Once out of Elle's dresses we relaxed with the help of a few bottles of wine we had brought for the purpose and sat around in our underwear and make up, probably looking a weird sight, but happy. It was interesting once again to study my fellow models, Max was now relaxed and behaving rather blokish, Jason was still sitting rather upright like a woman might, which on reflection I was doing also, but Sam was changed into his man stuff as soon as possible, it was noticeable there was a domestic brewing between him and his wife. Paul however would never challenge his wife, and was changing but not into his male things, he kept all his female underwear on, and for the first time I noticed he had a different pair of briefs to the rest of us and more than one pair of shoes. I could not see Sam wearing his pants and heels again, but Paul was a definite, as for the rest of us I was not sure. But we drank our wine and enjoyed retelling awkward or funny moments that we had had, all agreeing Max did look good in red.
Edith came in later and accepted some wine as she told us how wonderful we had been, her ticket sales had been better than usual, and we should be congratulated on a great success. Margaret followed, she had been at the side of the stage giving instructions so we went in order, and came to praise us for a very good effort. The last to come in was Elle, she had been busy selling after the show, and was overjoyed that she had sold more than usual and had people promising to come in to collect things they had ordered, giving Edith an extra cheque because she had made so much. All round a good evening, even if Sam was being a little grumpy.
My evening did not stop there though, Helen was was on a high, she had clearly enjoyed the fashion show, telling me how good it had been all the way home, making comment on all the outfits and how they looked on me, maybe suggesting some accessories to improve the look, also suggesting a couple were downright sexy, she even described the other models as attractive or sexy in certain costumes. When we got home she asked me if I had found any downside yet, as I undressed for bed I considered and said 'no'
'In that case slip into this' she handed me a satin nightie 'it will not only feel great against your skin, it will feel great as I make love to you'
Her tongue was almost in my mouth as she finished speaking, but I woke in the morning to the lovely sensation of soft satin wrapped around my hairless legs and thinking to myself 'that was fun, but time to get back to the real world'
Our friend and generally sweet little old lady, Edith had had her fashion show with her unusual models, it had been a great success, but what of the future. How would the five men react to their experience, how would the wives respond to seeing their 'men' in frocks.
This postscript I hope answers some of those questions.
I did rather think my cross dressing days were over once the fashion show was over, but I retained my smooth skin for a while and a pair of heels lurked in amongst my other shoes, tempting me to play with them. Then there was also Helen who made it clear she liked my hairless body and making love, with us both wearing satin.
It was a week later that Helen came home to say that Elle had been in touch and was asking if we would be interested in modelling again, my first reaction was to say no, but Helen informed me that her and Sally had already said yes on our behalf, I said a sarcastic 'thank you'
There was less planning for this show, Margaret was included as the off stage boss, Max and Jenny agreed 'for a laugh', Sam was missing and when I saw him later said there was no way he was being humiliated like that again, he just did not see the fun in it, maybe something deep inside him was disturbed by it, who knows. Paul was there though, sheepish as ever but ready to model again, so his wife informed us.
Helen advised me to get the heels out and have a bit more practice, we had four weeks before this show so I did teeter around for a few evenings but I was still ok. Then in the week before Helen put me through another hair removing evening, the skin was getting stubble and in her words was a bit of a turn off.
The show itself was about ten miles away in a nice community hall with a big stage. The routine was similar, get made up, start off in a business suit four changes, parade on the stage showing off the outfit, finish in an a fancy frock. Then sit back and relax as we change back into regular blokes. Elle was very pleased with our efforts and gave Margaret a cheque for the charity we had agreed to support, making it clear she would love it if we would do some more shows for her in the future. Margaret took it upon herself to speak for us all when she said yes, without consulting us, but none would not be saying no I was sure.
We drove home with Jason and Sally, who had a great time gossiping on the back seat. Most talk was reserved for Paul who they thought was just a little to good, and they argued over his eye brow shape, was it thinner now, and his new shoes which were quite high and narrow. But generally we just congratulated ourselves on a good show and the money we had raised without doing anything to hard.
Through these shows Helen and Sally had become good friends often calling round on each other for an evening chat, so when Sally invited us both for a meal, it seemed natural. This meal took place some five weeks after the last show and besides the occasional nightie wearing love making session I had not really embraced my 'feminine side' at all, that was until after the meal. Sally had spent hours preparing and cooking, so quite understandably Jason was the one who cleaned up the kitchen while the girls chatted over more wine. While Jason had his arms in the sink I noticed his arms were still clear of hair, and commented on it, asking if the waxing had a longer effect. He admitted that yes he was still clear, but that Sally liked him smooth and as he had little reason not to keep himself clear, he agreed to for her. I was a little taken aback, 'everywhere?' I asked, and was told except for a pubic triangle. He then went onto explain the benefits of waxing, my arms were a little stubbly by then, he said because the cream only removes the hair, which grows back from where it was burnt off, whereas waxing removes the hair completely, and if it regrows it is a new hair with the new soft tip, in time the hair follicles are all removed and the skin stays clear. With cream or shaving I would be constantly removing the stubble to maintain good skin. To say I was a little shocked at this revelation was maybe over exaggerating, but Helen walked in on us to find me stroking Jason's arm, 'oh yes, are we missing something?' she enquired. Quickly we explained our conversation and how we were just comparing waxing to cream. When she asked if I was thinking of waxing, I asked why she did not, she gave the expected answer of 'it hurts', but somehow we ended up saying 'if you do it, I will do it' which lead to Sally and Jason getting out their waxing equipment and encouraging us both to bare our arms. Before long we were both in our underwear and having a complete body wax, maybe all the wine had dulled our senses but we only winced a little. (I later realised Helen with her smooth skin had nothing for the wax to grip, so hardly hurt her) Eventually we were clear and Jason suggested as he refilled my glass that we were not finished, I looked at Helen, she fingered the elastic on her knickers and winked, then pulled them down. For some unknown reason I copied and lay face down letting Jason wax my arse. Sally then announced the best bit was to come and brought out a bottle of oil. Still on our fronts, our friends massaged our damaged skin, Jason was not Helen and I would have really enjoyed letting Helen do the massaging, but even though I knew it was Jason massaging me, I was reluctant to turn over as I had grown quite a hard on, which I could not hide. Helen turned over and letting Sally massage the oil onto her front, and when I refused to roll over, Helen just said 'it makes him hard, just like you Jason' we both blushed as she continued 'turn over we all know what to expect'. By now I was beginning to wilt and rolled over to let Jason continue. I was coping fine as he did my arms and chest, but as he worked up my legs I started to grow again. I then looked over to the girls, to see them both smiling at me and Jason. Sally was massaging between Helen's thighs, as I watched her breathing became laboured and she put her own hand to her labia and sighed. Sally winked at Jason who said 'your turn' and placed his oiled hand on my erection, gave it a few strokes and caused me to ejaculated while my wife and friends watched. Sally broke the silence that had fallen upon us with 'more wine?' Jason passed me some tissues to clean myself up, and said 'Sorry mate, don't know what came over me'.
It was late when we left to walk home, but before we did we hugged and kissed each other, and as Jason hugged me (which was a first, I never hugged a man before), he asked if I was ok, I replied that it had been a strange sort of evening for me, he agreed that it definitely had been different. Walking home hand in hand I asked Helen how she felt, she described it as feeling somehow liberated, lying there naked near me, also naked while friends brought us pleasure. I would not use the word liberated myself, to me it was more of allowing myself to be open. Then as we neared home she told me it was going to be a nightie night, and I knew exactly what that meant.
We did one more show with Elle in June and then another in October followed by one in November and special one in early December.
By November we were a regular group of friends, particularly myself and Jason plus Max, we would meet up with Paul sometimes but he was always having to leave early. Max only did things for the shows, just before you could see his arms getting quite hairy, but no one commented even though in the summer and in short sleeves it was obvious me and Jason had clear skin, and to no ones surprise Paul was clean as well. But then by October he also had studs in both ears, his hair was cut rather neatly now it had grown over his ears, and Helen swore he was wearing ladies trousers. But I would never argue with his wife, we guessed when she said get your ears pierced, he got his ears pierced.
The December show was different, it was winter so we had a few coats to model, but the dresses were all fancy, all party wear. And Elle had put a cat among the pigeons at the November show saying to the wives that as a thank you they could buy any outfit at cost, they looked eager to accept, then Elle added 'and maybe an outfit for your partners' we looked bashfully at one another 'well you will need something for a christmas party. You are having one aren't you?' We had booked for a party including Margaret, so Margaret asked Elle if she would like to join us, she kissed us all saying how much she had enjoyed working with us, and Margaret was left to add her to our party plans.
What we had planned was a meal in a nice Italian then going onto a club Max and Jenny knew, but the suggestion that we all buy a new dress for the occasion was a little shocking. It was all decided before the December show at a rehearsal, as we needed to all be ok with some rather difficult dresses. Paul was the first to say 'I will if you will' we suspected his wife had put him up to it, then surprisingly Max agreed and said it could be a laugh going out in public with no one knowing, leaving Helen and Sally to look at each other and giggle as they agreed to me and Jason joining in.
Elle was very kind and allowed us an evening in the shop so we could all choose a dress and have no problems trying them on. Helen bought a lovely grey chinese style dress with slits up both sides, I chose, or rather everyone said it looked great, a pale blue silk wrap over dress with acres of skirt. Jason ended up with a short sparkly mini, Max was in red, but Paul took a halter neck Marilyn Munroe style dress, all I could think of was 'we will see his bra'.
A surprise at the December show was that Paul turned up in a skirt and blouse, fully made up and with his hair restyled and pendants hanging from his ears. His wife appeared minutes later in a severe black suit with tie and flat shoes looking as male as Paul was looking female. 'Wow Paul, you are taking this a little too far'
'No' he replied 'just dressing to reflect my personality, I hope you don't mind'
'Not at all, in fact some things make sense now'
We had another great show, if a little more harassing as the dresses were often more involved and for the occasion we had got new party shoes with thin higher heels which made our progress somewhat slower. When we finished Elle gave us our purchases, she altered some because we are not perfect 10s and 12s. Then as we tried them on Jenny asked Paul if he was going to wear his home, he looked at his wife who nodded, 'I suppose I could' paused, then added as an excuse 'would save me changing again'. Then Jenny turned to Max 'you do the same, be a laugh'. Soon all nine of us were walking out of the back door to our cars, four glamourous women, and five women in jeans and baggy jackets. Sally drove while me and Jason sat in the back like the women we represented to the world.
Their car is only small and I was sat very close to Jason, so when the conversation turned to how we looked and I complimented Jason on his good legs, while he fingered my silk dress saying how nice it must feel on my skin. A comment from the front suggested we fancied one another, and being in a silly mood, turned to Jason and said 'Oh darling you look just divine, give me a kiss' and he leant over and put his lips to mine. I froze, I was only joking. The girls saw it and started laughing. Then Helen started resting a hand on Sally's thigh, putting an arm around the shoulder, just like I might have done to her. This encouraged Jason to copy her antics and was soon stroking my silk covered thigh with his hand, getting me to put my arm around him so he could snuggle up to me. I knew I was being teased, but as we unloaded the car and Helen made a drink for all of us, Sally was being very touchy and affectionate towards her. Then as we all sat down Helen suggested Jason might get jealous, 'why should he when your sex bomb is giving him the come on'. Sally sat on the arm of Helen's chair and put an arm around her, then Jason came and sat next to me on the sofa, took my drink from my hand and said 'what is sauce for the goose is good for the gander' I was thinking 'that's not quite right' when he took my head and kissed me again, this time properly, tongue teasing my lips. I looked over to Helen who by now had Sally sitting on her lap and being far more adventurous than me. Jason soon had a hand on my thigh and stimulating my erection. I was not really enjoying Jason's attention when Helen and Sally start laughing. I soon discovered that I had been set up by the other three after I froze in the car. Soon after, they left us alone and Helen made it up to me with some proper male/female affection, all be it I was still dressed as a good looking woman, in very nice silk dress to encourage my senses.
I attended our christmas gathering with more inhibitions than I had felt during this cross dressing experience, this was possibly an after effect of the teasing I had suffered at the hands of Jason and Sally. Even with my reservations we were still quite a sight, ten women dressed up to the nines, at first and even second glance the public would not recognise that four of those women were in fact men. Elle had a beautiful cerise flared 1950s style dress, Margaret had always been in trousers, this time she was in a very feminine outfit. In fact the only person in trousers was Paul's wife who was in a very nice suit. In my reserved state I felt the dynamics and personalities had changed since our first show. Obviously Sam had pulled out after one show, but over the year we had all changed, Max had been a joker his performances had always let his male traits show through, but he was getting bored I think and not really trying to play the role. Jason was still playing a very feminine woman and was clearly taking his cross dressing seriously as he had been telling me of some things he and Sally had been up to. Paul was now a convincing woman, he had fresh piercings, now sporting two in his ears lobes and a stud in the top of one, his hair was also blonde and cut in a female style, but more limiting for him if he wanted to be a bloke anytime soon was his narrow eyebrows, long finger nails and plumper lips, and possibly his very realistic unsupported bust, from what I could see there was no bra, yet there was a bust and clear nipple in the top of his dress. Conversations during the evenings confirmed and strenghened my suspicions, Paul told me he was now dressing full time, since the last show he had lost his job because of his poor performance figures, so his wife had suggested that he should look after the house at least until the new year, clearly as a housewife. When I asked how he would get a new job looking like he did, he said that applying as Paula had crossed his mind, but his wife had got a good raise and promotion so they were not desperate for cash. Max used the party to announce his retirement from the shows, he had done enough and fancied a different fund raising challenge in the new year. He did not say, but he was bored and had reached his cross dressing limit which he did not fancy going beyond. Jason was the one I was closest to and knew he and Sally had been having fun cross dressing, they had been out recently as lesbians and he did seem to be wearing women's clothes mixed with his male things. I know Helen would like me to make a foursome when they go out but I was feeling myself backing away from this gender blurring behaviour, I do like my smoother skin, the sensation of satin and silk on my skin is always a delight, but I do like being a man so the brakes had been applied to my adventure into the female world.
After our meal, then dancing in the club together. We all parted on very good terms, the party had been fun and we still enjoyed each others company, but it was the last time we would be together as a group, and definitely as a group of men modelling for Elle's fashion shop at a charity function.
No longer with the reason of doing fashion shows for Elle, Jason and myself are encouraged by our partners to explore our new found interest in how we look.
I could not believe I was actually getting ready to go out dressed as a woman and had agreed to it in front of my wife and our friends. Not that wearing a dress is anything new I have been doing it for Edith and then Elle for a year now, when I had modelled for them with the others. This time it was not for charity. It was for fun.
We had realised how much fun was to be had from playing with gender identities when my wife was massaged by our friend, and Jason massaged me. Neither of us thought ourselves gay until that day and the reactions our bodies gave to being caressed by someone the same sex was shocking at first but then stimulating once the shock had worn off.
So I am now the finished feminised article, Jason specified a short dark blue satin slip , a loose over dress in blue, sheer fabric with massive medieval sleeves, blue satin underwear, shiny blue platform sandals. He had also asked if I would get a spray tan, have my hair bleached to a dark blonde colour, and grow my nails so I could have a french manicure. And I had said yes to all this, and I had said it without thinking about it, being asked to dress again and having described what he thought would look good on me was all the incentive I needed to go shopping and get myself prepared for a night out.
Add to what I have agreed to, my Helen is no longer my wife, as I was willingly being lead into a dress, she was being lead in the opposite direction. She had agreed to make up the gender balance for our night out, Sally was encouraging Helen to be as manly as possible, she wanted a crisp white shirt, jeans, smart trainers, that was easy but the moustache and new short hair style were something Helen might not do, that was what I thought at the time. However I was proved wrong, she was there with a well applied goatee beard, swept back hair style and the full male dress even down to briefs with a little extra in them to fill the space at the front. She looked rather camp being a small frame for a bloke, but she looked the part non the less.
Needless to say when Jason and Sally turned up at 7.30 Helen was ready (as the bloke should be) and got lots of praise when she opened the door, all of which I could hear as I finished getting ready hanging some long chandeliers from my ears and wrapping a long string of beads round my neck. One last look in the mirror to check I looked ok, I did, but I had no idea where they thought I could go dressed like this, then it was downstairs to see if I got as many compliments. Sally told me I looked fantastic and kissed me on the cheek, Jason however put a hand on my arse cheek gave it a squeeze, told me I looked hot, then kissed me on the lips. I froze for a millisecond, then Sally took my hand and lead me into the front room 'did you not realise you and Helen were swapping partners as well as genders tonight?' I must have looked puzzled 'I guessed not'
I was about to say something when Helen walked in 'This is where our women are hiding,' then added 'Jason says the taxi is here, you ready dear?' and looked at Sally not me. So Helen knew she was going out with Sally, just me who had not realised I was going out with a real man and not a manly woman I had been getting ready with. While Helen was taking hold of Sally in a very proprietarial fashion, Jason came through and asked if I was ok, I told him I was catching up with the situation pretty quickly, to which he said 'Good, would be a shame to waste all your beauty' then he looked at me and I felt his fingers in mine 'Ok being with me' I nodded my reply, to which he squeezed my hand, 'You are mine for the moment' he said, I replied 'Yes. Yours'
From the front Helen called out 'Come on you two, plenty of time for that later, let's get going'
Jason and Sally had done their research and found a burlesque show with plenty of overdressed people in the audience so me and Helen did not feel out of place. Jason was the perfect companion, he never left my side except to get drinks from the bar, and when he was beside me, even if he was not talking to me, he would have a hand touching some part of my body. The whole experience was rather exhilarating as I had never been someone's 'bird' before, and with a bloke who was making all the right moves. What was stranger was that Helen was treating Sally in a similar way and it was not bothering me. Given that I was in not position to criticize, seeing your wife dressed as a man and kissing another woman I would have expected some negative reaction, maybe it was the cocktails or Jason's hand on my body making the satin dress stimulate my senses that stopped the reactions.
After the show Jason took me to a club where he bought me another drink and showed me how good a dancer he was. Some time around then I lost track of where Sally and Helen were and I was on my own with Jason. I was really enjoying dancing with him and was also reciprocating his attentions so when the slow numbers came up it was easy to just sway with the music, my head on his shoulder and nuzzle his neck.
About one I noticed my phone had a message. I read it and after putting it back into the clutch bag told Jason I needed to use the ladies where I meet up with Sally.
'Having a good night?'
I nodded 'Yourself?'
'Great'
'Is He.....nry being good?'
'No'
I looked puzzled.
'He is a revelation, known you two all this time and my god you know how to make a girl smile'
'What?'
'Your H..enry is so good he is fantastic. And how is Jason?
'Bit of a surprise as well'
'Anyway, what do you want to now?'
'How do you mean?'
'Do you want to go home with Jason?'
I must have been slow as I did not reply
So Sally continued 'And I go back with Henry. Then we catch up tomorrow'
'You mean........'
'Yes I do.'
'but what do the men think?'
'You are so sweet, they have already decided. Jason wants to take you back to his, and Henry is hoping to take me back with him.'
'There is only me left to say yes then it seems'
'So?'
'Well if Henry is fine with it'
'He is'
'See you in the morning'
'Have a look in the second drawer of the chest if you fancy something nice to sleep in'
I looked at Sally and realised she was telling me to sleep with Jason. All I could say was 'Sorry I can't make you a similar offer'
'No need, I have everything sorted' and with that she kissed my cheek and turned to walk away from the mirror that we had been looking into as we kept on reapplying lipstick over and over again during our conversation. It was then as her long legs took a silver mini dress which scarcely covered her arse out of my sight, that I suddenly realised I was entering new territory. In the past I would have lusted after her gorgeuos arse, but that evening I saw her as attractive but found myself hoping I looked as good. But then unexpectedly hoped she had a good time with her man as I speculated on what might be instore for me and the bloke I have been dancing with a little more intimately than had ever thought possible.
Jason was waiting for me, 'Ready to go?' I put my hand in his and let him lead the way. The taxi ride was rather nerve wracking as it gave me time to consider what I was actually contemplating doing. But Jason kept a firm hand on my thigh, while I kept a firm hand on my nerves.
After paying the taxi he once again took charge and lead me into his house. 'Champagne?' he asked but did not wait for an answer before opening a bottle and pouring two flutes. 'To us' he toasted. Then drank some, I followed suit and he soon topped up my glass.
'This is all new to me you know' I ventured
'Me too as well, but your Helen fancied having a go at the cross dressing and after that massage session, well, Sally thought this might be fun, and you do look hot. Did you notice how many men were giving you the once over?' he swallowed some more from his glass 'Right,,,,,do you want some more champers, or do you want to take up where we were on the dancefloor?'
I made no move, so he filled up my glass, then after putting the bottle down came up behind me, kissed my neck then started to unfasten the back of the overdress, soon it was lying at my feet, next a few more kisses on my neck and the straps of the satin slip were off my shoulders and sliding down my arms to meet it's partner. I was left standing in my blue satin bra, thong and heels. My dick straining against the restraining surgical tape that secured it between my legs.
'Fuckin gorgeous' Jason was stood in front of me and admiring me from arms length.
'So what next?' I asked
'You could help me out of these things'
I undid his belt then his fly while he caressed my bare skin. The trousers did not fall as easily as my outfit had. 'They need a little help' Jason suggested. So I helped them down his legs, then he sat down so I could take his shoes off and pull the trousers off completely. When I looked up his dick was standing up in front of me. I looked at him, and he looked at his erection, I knew what he wanted, just like I would want, if Helen was at my feet having got me hard. I took it in my hand first and stroked it, then with his fingers he played with my lips and tongue guiding me towards his cock until I made contact with my tongue. It was nothing like I expected, the skin was far softer than I would have thought, and warm, and salty. A few licks and my lips were on it, then with a hand cupping his balls I tried letting my lips swallow his shaft, just the tip the first time, then the head, he moaned and arched a little. This is what he wanted, and I could give it him. Encouraged by his moans I slid up and down, going a little further each time until my mouth was full of him. Then suddenly he grabbed my head with his hands, let out some swear words and pushed into my mouth just before he exploded into an already full mouth.
He relaxed and I knelt back tasting his cum all over my mouth and on my lips. 'Would you like a drink?' I got up to retrieve mine so I might wash away some of the sticky remains.
'Thank you' he said as I handed him the glass. 'Time for bed I think' he continued 'I shall be up in a minute'
I went to his room and looked at the super king size bed, then I saw the chest and remembered 'second drawer'. I was just looking in when a voice behind said 'The white one would seem appropriate for you tonight my gorgeous virgin'
The white silk nightie felt fantastic as it flowed down my skin.
'Ever done anything like this?' he asked
'Never. And you?'
'As a kid we mucked about with show me yours and I will show you mine sort of stuff. But no I have never made love to some one with only one hole'
'So what do we do?'
'Well we get old Gregory Peck to wake up, then we make sure you are nice and relaxed, then I try and make you enjoy yourself'
Half an hour later, I am lying on my back, my arse well lubricated with Jason sliding in and out, and me holding his arse cheeks wanting him to push in further as I feel an orgasm building inside me. Then I am convulsed in spasms as wave after wave radiate from my private parts and all I can say is 'Go on, go on' and he did until I sudsided and let go of him.
Lying in the afterglow 'Did you enjoy that?' he asked
'What do you think?'
'I will take that as a yes then'
'Oh, that was so different, maybe one day you should let me return the favour'
'Oh no, I might like wearing a dress, but no way am I doing what you just did, I like being the man in bed'
'You really should try it'
'No thanks, I will happily screw you as much as you want, but it has to be this way round. Ok'
'OK' I agreed
The next thing I knew was waking up in a strange bed, my head feeling rather fragile and my arse competing with it in tenderness stakes, and then there was the need for a shower, I felt horrid between my legs, and looked a sight when I saw a mirror. My first thought was to have a shower, then a coffee and some paracetomal. Jason did not seem to disapprove of this as he was in the kitchen already. I was coming round slowly, then as I sat on the side of the bed I took out my phone and read the texts 'Hope you are OK' I replied 'Fine, and you?' within seconds a reply 'Fine, taking Sally out later for lunch' Which left me wondering how she would be dressed, and what I might be able to wear, the blue outfit might look a little out of place on a Sunday morning.
I found a silk kimono in the drawer and felt safe wearing that to go downstairs.
'Good morning' Jason said to brightly
'Any coffee?' he poured me a cup and offered some painkillers.
When the cup was nearly empty he asked if I wanted another, poured it, then said 'You still look good you know'
'I doubt it, I need to find some cleanser and get myself sorted for going home.'
'Sally keeps all her stuff in the spare room, and there is a bag in there for you, left just in case things turned out this way'
I thought of being difficult, all this had been planned without my agreement, but I was still not up to full speed thinking, and when eventually I thought about it I really had nothing to complain about.
Jason was clearing up and asked what I was thinking of doing with the day, 'Not thought about it much, Helen says she is going out with Sally later'
'I think you will find that is Henry is taking Sally out later'
'Oh' so that was that question answered. 'I think I will go and clean myself up and see how I feel in a bit'
'Ok, give me a call if you need anything sweetheart' I looked down and saw my nails below my fake breasts and felt committed to the role I was dressed for, at least until I found some solvent release.
In the bedroom I found some cleansers and creams, then I opened the bag that I recognised as mine. Inside was a chioce of male and female clothing, then as Jason went past the door asked if I was ok for everything, I felt the silk of the kimono brush down my leg and my decision was made. A day in skirts as Jason's woman would be rather nice for a change.
I was soon in Helen's chioce for me for the day. White underwear, white lacy top, shocking pink mid thigh lycra skirt, white 4" sandals, that was the clothes, there was also some make up and along with Sally's collection I was soon back to my feminine self. Jason was clearly pleased to see me when I finally made it into the kitchen to see if there was anything to eat. He blatantly patted my arse and suggested I should be be offering to make him something seeing as how I was woman around the place, I countered by telling him it was the age of equality but non the less went and made myself a coffee and found some biscuits for us both.
I must admit I felt a little out of place in my sexy outfit as we walked into a country pub in the middle of the afternoon for a bite to eat, but I felt fancied by Jason and that help quel any misgivings. He had made it clear both before we left and while we were driving that he wanted to make me scream again, and that did something quite nice to my ego. Needless to say the meal was fine, the lusting men a diversion at times, but the walk out to the car was great as I considered the possiblities left to us. In the end we were sensible, I needed to get home so we went to my house initially to drop off the bag. A quick glance around and we knew the house was empty, this improved Jason's libido and was soon fondling me as though his life depended on it. I was not far behind once Jason had got me started. We had some gel in the bag and were soon ready for the coupling. Jason took it slowly allowing me to relax as he stretched my hole, then once in he rode me until I could think of nothing else but having him inside me. Once again I enjoyed my orgasm, but this time the afterglow was somewhat disturbed.
'I see you have the hang of that then, you two'
Sally and Helen, sorry Henry were stood at the living room door, how much they had seen I did not know, but what they did see was Jason with his pants down and me with my skirt around my waist.
Sally broke the silence 'I was going to put the kettle on, anyone want a drink?' The coffees were drunk as we reminised over how good we had all looked, how much fun the show had been, and because there was no denying it how much delight the sex had brought. Sally and Helen admiting to having spent the night together and enjoying each others pleasure in ways me and Jason had never done.
A good weekend all round we concluded before Jason and Sally left so we could clean up and remove the additions that made our characters more believable, hopefully making our appearance at work the following morning not too shocking for the colllegaues who thought we were a regular couple!
You might want to read the earlier 'Beware sweet little old ladies' so you get to know the characters
I was now rather effeminate looking for a man, my friends had seen to that. My most blatant reminder every time I looked in a mirror was the eye brows. Just how thin did I really need to pluck them, surely not this narrow? But there was also the naked in the shower moment when I caught sight of my legs. Still hairless of course, but the neatly trimmed pussy with no manly genitals showing (The tape was just too painful to remove). I had dyed my hair back to something close to my natural shade, it was a little too uniform, but that was ok. The tan I explained away as being out on the hills and got some colour in my cheeks. Good job my tanned body was not on view, or that lie would not hold up.
Anyway, I have not really spoken with Helen about our night out with Jason and Sally. We clearly have not had sex due to my hidden genitalia not being available for service. So after a week I am getting randy and the glue is weakening enough for a hot bath and some eye watering tape removal. That evening we made love. It was sore but good to be back with Helen. Then, in the afterglow as we cuddled up. 'That was a reversal from our last time you know' Helen whispered.
'I know'
'Interesting that we have both been in each other’s position now'
'I suppose so'
'Which do you prefer?'
That flicked a switch on in my head 'What?'
'Do you prefer to put your thing in a hole, or have a thingy pushing into your hole?'
'Is this a trick question?'
'No, just curious'
'They are both different, is that enough?'
'Well, would you like to be screwed again?'
'Jason was just a one off bit of fun, nothing more, I love you'
'And I love you, but I have this toy that I used on Sally when I was being Henry, and well I could screw you'
She was nuzzling my neck and tickling that sensitive spot just in front of the arse hole. 'I liked being on top as it were'
I swallowed. This was all rather unexpected. 'You have a dildo and want to fuck me?' I was trying to keep my voice calm.
'That’s it, yes'
Next thing I know she has rolled away towards her bedside cabinet and picks up a tube of lubricant. It is cold as she massages it around the hole and then squeezes some inside.
'You really want to shag me, don't you?' I asked.
I was on my back with Helen over me. Next she retrieves her toy and fastens it to herself.
'Now then my dear, I want to see if I can make you smile like Jason did'
There was the challenge, she thought I had better sex with Jason.
'It was different, was it not different with Sally and you taking her?'
'Not that much'
I felt the penis push against my sphincter muscles and thought, 'somehow I have to let her do this. Relax' Then she was inside and I winced. Control my breathing. This was so different to Jason. I was relaxing as she pushed further inside me. Then she touched something and I felt myself tense. And again. She was pushing into my arse cheeks with her hips. I could tell she was loving my reactions. I was tensing with every thrust by this time. I grabbed her arse and pulled it towards me. A few more thrusts and I tensed up into an arch against her dildo. My panting and exclamations a clear indication that she had indeed fucked her husband.
To be honest I have no idea if she came or not. I was so wrapped up in my own experience, I did not notice. But I had screamed for her which I thought was what she wanted.
'You never scream like that when you screw me?'
''That is different.'
'You seem to enjoy being fucked though, don't you?'
'Hard not to scream for some reason, rather like you I suppose.'
'Just seems that you get more out of being the hole'
I tried to divert attention from me 'And how did you like being the man?'
'I could get to like it very much. The sex is about the same for me, but the pleasure of being the one who made you cum, who made you scream. That was great.'
'That is good.'
'Is that how it is when you have me?'
'Pretty much. I like to give you pleasure, if you don't cum, I feel like I failed you'
'Sleep time I think, my darling'
I did wonder how this experience might affect our relationship. I had been nervous about being Jason's partner, and this was something different and potentially dangerous.
Clearly things had changed. Within a week, I had gone from a bloke who wore a dress on occasion for charity, to a bloke who willingly partners another bloke as a girlfriend, and then gets shagged by his wife. Just how much did I want to venture into this new territory I was not sure? Nor was I sure how far Helen wanted our relationship to change. Did she want to be the 'man' about the house?
Nothing much was said for a few days, then she told me we were going out on Saturday with Jason and Sally. I waited for the next part but it never came. I half expected her to suggest we go out as their partners again, but I was mistaken. We went out for a drink and a curry before walking home and sleeping in our own beds. I rather enjoyed that return to normality. What did surprise me in the morning was Helen waking me up, stroking my cheek, 'Does shaving every day not get to you?'
'Bit of a chore, but I tried a beard and it looked rubbish, so shaving is my life'
'I read about electrolysis, stops regrowth'
'And I hear it is painful'
'But to never shave and have a smooth face'
'Like yours?'
'Yes like mine, don't you like it?'
I stopped playing. 'You want me to have my beard removed, is that it?'
'Be nice, wouldn't it'
'I'll think about it?'
'No need, I booked you an appointment for Tuesday after work.'
'You did what?'
'Well I know you would forget and be too busy to organise it, so I was being helpful'
'Once, and we see how it feels' I tried to be assertive in my tone, just not sure I managed it as I considered what I had let myself in for.
Tuesday after work I call at 'Hairz' and spent an hour having my face subjected to a new machine, which they told me did not hurt and killed more hair with each treatment. Instead of electrocuting each follicle, it used light to do the damage and did not burn like the needles. I did have a red face from the strong light, but was reassured it would fade overnight, which it did. Wednesday morning I am amazed that I do not need to shave, nor on the Thursday. Friday there was some stubble, but not much. Helen loved the smoother me, and booked me in for another session.
This time however, Clare, who was doing the work, casually dropped a question on me.
'Would you like me to tidy up your brows, they are starting to regrow?'
I stumbled over my words. 'No they are fine, thanks.'
'Your colouring is starting to grow out as well. If you want me to recolour, I could do that as well'
'No, it's fine thanks'
'Just a thought' and then went back to her work.
That was too much like being found out, and I was uncomfortable with it. I told Helen when I got home, who just suggested I should have been honest and told her about how I model women's clothes. I said hardly. She said everyone knew who had been to Edith's show. I said, oh great.
Clare told me the next time I was in that she had bought the red dress Sam had worn to Edith's show, so she knew everything it seemed. Well except for the time I was Jason's partner.
The next significant moment was shopping at the local supermarket and hearing a voice behind me. 'Steve, how are you?' I looked round expecting to see someone I knew but missed the face first time round. 'Steve'. A rather well dressed woman was speaking to me. I looked harder. 'Paul....a?'
'Yes, and I'm fine thanks'
'Oh sorry, I'm well, how are you?'
'I must say you are looking good, been doing any more shows lately?'
'No, that seemed to tail off, didn't it. But what happened to you?'
'Did you not hear? My... ahhum.. boyfriend got promoted again. And well he likes his meal on the table when he gets home, and has never liked an untidy home, so we decided it was best if I just stepped into the role of housewife fulltime'
'Oh, I never heard, but the neighbours?'
'We moved a few months ago, nice apartment, never see the neighbours, and those we do don't know of our past, it's great'
We had stood for a few minutes when I surprised myself by saying 'Would you like a coffee when you are through here?'
'That would be lovely, see you in the cafe later then'
She/he walked off. Cotton summer dress, linen jacket, high heeled sandals, all in cream. If I did not know better, I would have been convinced I was looking at a well dressed woman in a supermarket.
Twenty minutes later, I am sitting opposite Paula, drinking a coffee and asking how far has he gone, and why. From the answers, it was clear he loved being a housewife. The cleaning and cooking was just so interesting, the way she explained it. And then there was the being a woman part of it. She loved the whole thing about looking good, getting dressed up, even if it is just trousers and a top for washing the car in. She loved to be thought of as a woman. For some reason I am not sure of, I told her about the beard removal after she commented that my brows looked neat. We exchanged numbers before we stood up to leave, then just before we parted, the last words were 'You know Steve, you were the best out of the five of us, so natural'. Before I could answer, we were too far apart. My only thought being 'Let's hope Helen and Jason don't agree'
I told Helen about my encounter with Paul. I was still thinking of her as Paul, when clearly he was for everyday life a 'her'. Helen was fascinated by my tale and that evening she made love to me in her preferred way.
Then I was to find out Helen had been in my phone, got Paula's number, called her and invited them over. Paula declined, saying she had plenty of time and invited us to their flat. According to Helen, she had never done a dinner party and wanted to try.
We turned up the following Friday evening, me in a nice shirt and smart trousers, Helen in grey trouser suit. Paula's partner had been called Joan, but we were told she liked to be called Joe now. Joe was in a pressed black shirt and jeans, the hair was short and neat and of course no trace of make up, that was now Paula's department. She came out of the kitchen, an apron hiding some of the pink off the shoulder dress that flared out from the waist due to the net underskirts. She looked pretty, which is not something I should really say about someone I know was called Paul by his parents. Joe played a great host, with Paula preparing a fantastic meal which we all enjoyed and all thanked her for. What was unexpected came later. Paula was clearing the table and I felt it was polite to help and rather expected the others to do their bit, but it ended up being just me and Paula in the kitchen. Then with everything in the washer and things in soak, I returned to the lounge to find Joe and Helen sitting with big brandy glasses in hand. All they needed were big cigars to finish the picture of relaxing gents waiting while the women finish up.
'Enjoying yourself?' I asked
'Never tried brandy before on its own, this is very nice Joe' Helen replied.
'Paula, get Stevie a drink'
'Come over here and see what we have Steve' Paula directed me to a cabinet in the dining room.
'Is Joe always so..........blokey?'
'Yes, rather complement each other, don't we?' she replied 'So what do you fancy?'
She poured herself a liqueur that smelt of oranges. 'Can I try one of those' I said innocently.
We returned to our partners. Helen even patted the seat beside her to indicate where I should sit.
I was getting the distinct feeling Helen was enjoying herself a little too much as she imitated Joe.
Nothing else happened that was significant. No, that came once the taxi had dropped us off at home.
'So Stevie, that was fun, did you enjoy yourself?'
'What is with the Stevie?'
'Suits you, Stevie.'
'You were liking being with Joe, weren't you?'
'Yes, nice person, calmed down a little from the person who came along to the shows, quite self assured now'
'I suppose so, made me a little uneasy at times, like with the Stevie stuff. And did you see the look I got when we came back with those nice orange flavoured drinks?'
'Well, you are bit of a girl when it comes down to it, eh Stevie'
I half expected her to come to bed and want to make love to me, but we were tired and just fell asleep once we lay down.
Midweek, Helen, quite out of character, tells me she is going out for a drink. When I asked who, she told me it was Joe. She went in jeans and a plain sweater, flat shoes and her hair brushed back into the shaggy version of the style she had for our night out with Jason and Sally. I have no idea what went on, but when she got home it was clear, rather in the way I sometimes made it clear when I wanted sex, that Helen wanted me in bed. And no ambiguity. She came to bed with her toy already in place, I was not going to be screwing her that night, for sure.
A couple of weekends later, Helen invited them over for a meal at our house. She was working extra hours that week, so I did the preparation and had a practice cooking session midweek, coincidentally after my last session of having my beard removed. So when Friday came round, Helen was not finishing work until seven and I was home early, so it was obvious that I should just get on with the food preparation and setting the table out. Helen came home, gave me a kiss to let me know she appreciated how much I had done. We showered and changed. Helen once more wearing her black jeans and a plain shirt. I swear her tits had shrunk if I had not seen them in the shower. I also noticed that her hair was short and neat once more. Anyway, the evening went off well. Paula was in a stunning, plain but well fitted gold dress that flattered her curves. Joe was actually in a suit. Seeing as how I had done all the work, I did the finishing bits before serving the meal. Helen made a point of telling our guests how I had done it all myself and how lucky she was to have such a good partner, not husband I noted. Helen did start to tidy up, but Joe distracted her and left me to discuss something or other. So once again, Paula and myself cleared up.
'You look fantastic tonight' I said rather absentmindedly to Paula.
'Thank you, where does this go?' as she held a pan in her hand.
'Over there'
'I hear you have had your beard done away with'
'Yes, last session for a couple of months was last Tuesday'
'I could not wait to stop shaving, you will love it'
'It is much nicer already'
Then she added 'Planning anything else?'
'Not that I have thought of'
'Well I was talking to Clare this morning'
'Wait, you know Clare'
'Yes, been going to her for over a year now. Ever since Joe decided I would make a better wife than husband. Anyway, I was telling her about where I was going this evening and it turns out she has been doing you as well. Reckons you are still dressing as well'
‘what has she been saying?'
'Well that you colour your hair and that you really should get your brows tidied up'
'It was just some fun, one night, that was all' I was being defensive.
'It's alright Stevie, I know exactly what you mean'
'Paula, stop it. I have a life as a bloke, there is no way I could do what you have done.'
'Don't be so sure. Eighteen months ago I would have said the same thing, but looking at your Helen and what Joe tells me, if I was you I would keep myself open for changes.'
'Thank you, but Helen and me are fine'
'Ok' she said 'I think we are done here.'
We walked in on Helen and Joe drinking my favourite whisky, the bottle between them.
As they poured another measure, Helen looked at me. 'Stevie, you never told me how good this stuff is. Joe has been explaining the difference between speyside, highland, island and so on. He's invited me round tomorrow to sample some of his selection'
'Oh' was all I could manage. 'Paula, what would you like?'
'A liqueur please'
I went to the cabinet and feeling my masculinity being threatened, I dared not join Paula so got myself a whisky. Even though I had my drink, I am not sure what it was but I felt like I was being compared to Paula. Joe and Paula spoke to Helen as if she were a man, whereas Helen and Joe in particular spoke to me as though I were not a man. Hard to explain, I just felt Helen and Joe were enjoying being mates in a bloke sort of way.
Then the topic of my sessions with Clare came up. Helen stroked my cheek, telling everyone how nice it was of me to do it, and how nice my skin now feels. Then Joe refers back to the shows and tells me how good I had looked. Paula repeated her phrase that I was a natural, to which Joe and Helen both agreed. I was blushing from embarrassment when I said thank you. Then Paula lets the cat out of the bag and tells Helen that Clare had offered to colour my hair and do my brows.
Helen's reply 'Oh,Stevie you never said, as a thank you for everything you have done tonight I shall treat you to whatever you want at Clare's'
'No it's fine, I don't need any thanks'
Then Paula chirps up, 'Oh but you must, it will be great. I will make us a double booking, next Friday, what time do you finish work?'
I was trapped, I did not want to cause a scene, so just replied 'Four'. I would make my excuses later.
Our guests left and as we undressed, I noticed that Helen had been wearing her toy inside her boxers. I was in bed and feeling its hardness pressing into my back and realising that once again Helen was taking the dominant role in our love making as she teased and massaged me similar to how I used to encourage her to respond to my advances only a few months ago.
Sunday and I am left to my own devices. Helen is off whisky tasting with Joe, so I take myself off for a walk in the hills, something I used to do until recently. I am home when a rather drunk Helen is dropped off by Paula, who just says 'See you Friday' before going back to her car.
'Right then my little Stevie, what have you got us for tea?'
'Nothing, not been in long myself'
'Aw, come on Stevie, be a good little girl and go and rustle something up for me'
I looked at her with my jaw frozen. What is with the Stevie and little girl stuff? 'I am not your little girl, you are drunk, but if you ask nicely I will make you something'
She smiled 'Thank you Stevie' with the emphasis on the name, Stevie. 'I suppose that is short for Stephanie' she said with a smirk.
I turned and walked away. I made a quick salad and took it through. She was drinking my whisky again. 'Not bad choice you know, that Laphriag is nice though'
'What is going on?' I asked
'Just having some fun, really get on well with Joe you know'
'I had noticed'
'Paula is a cracking wife you know'
'She seems to like being one'
'I just keep thinking.........'
'That you want to be like them' I finished for her.
'Well, now that you mention it, yes. Paula is a far better housewife than Joe ever was, frustrated him to death he says, whereas Paula loves it all.'
'And you think we should do the same?'
'Why not, I am rubbish at keeping the house clean, you are a much better cook, and if I am honest, much better looking than me.'
'Because we can't afford it, because I have a life which means I need to be a bloke at work, because it needs to be both of us wanting this.'
'Paula did not know until Joe made certain changes'
'Well I don't want to change, I am happy as a bloke'
'I will remind you of that the next time you are screaming for me to push harder, shall I?'
'That's different' I got up with my half eaten meal and went to the kitchen to throw it in the bin. Something deep inside was telling me she was right, yet I just did not want to accept it. Every time I saw Paula, she was stunning, and the dream Helen had, cast me in that role. The stereotype housewife.
Helen came up behind me 'Look sweetheart, I just see them so good together and think. That could be us'. She put her arms around my chest and pulled herself into my back. She had the toy again, was all I thought. 'Maybe if we just try it one step at a time'
'I think you are many steps ahead of me already'
'Cheeky.' She turned me round so I was facing her. 'No I don't mean we suddenly switch, no we take it in stages, try out new things, and see how it feels to be a little more on the other side. What do you say?' She put her finger under my chin and lifted my head up, tears were welling in my eyes. 'Oh dear, I am sorry. I did not mean to upset you' She hugged me and calmed me down. 'Now why the tears?'
'Sorry, I should have never agreed to go out with Jason, it has all gone wrong since then'
'I disagree. I saw you all dressed up and you know what, I was jealous. Yes, I had a very interesting time with Sally, but I really wanted you'
'That does not help'
She then closed the conversation with 'I really would love to take Stephanie out some time.' Then a kiss and she was gone.
I cleared up on automatic, then went and had a bath. I looked at my naked body, the bikini shape was still there, my legs were a bit stubbly, which made me think she has always liked me smooth skinned. Then I thought how I had allowed her to get me to remove my beard. I either had to stand up to this gradual change or just go with the flow as they say.
On Monday, Paula rang to tell me she had got us booked in for four thirty on Friday. She was going to have a blow dry and have her acrylics filled at the top. Then told me I could either have a manicure, brow shaping, colouring with a cut and blow, a facial or even a waxing. Maybe more than one depending on what I chose. I tried to tell her that I did not need any beauty treatments, to which she said 'Pardon me, but I think you do. I am fed up being the only one who makes an effort at our dinner parties, and besides, Len has told me you actually need all of those treatments'
I ignored everything else she had said 'Who is Len?'
'Oh Come on Stevie my girl, Len is that fantastic hunk you should be saying thanks to, he is paying you know'.
Helen= Len I got it 'Sorry Paula, I am not sure I am cut out to be like you'
'sure you are'
'Sorry I have to go' was the only way out of it I could think of. Could I stand up to Helen or even Len
I said nothing until Thursday when Helen came home from work. Over a lasagna I had made she casually asked 'So what are you having done tomorrow?' She was in a white shirt I had ironed the night before because she was late coming home and I had had time to sort out the washing.
Did I have the courage to say I was not going? 'Not decided yet' Not exactly a convincing no was it?
'Get yourself waxed if you want help deciding, and maybe the brows. Did you see Paula's eyelash extensions last weekend? I suppose they are not on the list'
'No ' I replied. Eyelash extensions, whatever next, breast implants. 'you sure this is a good idea, I really am not sure you know'
'Be excellent, I get to be a bit more like Joe, you get a little more like Paula, like we said the other day'
'But why do I need to be even a little like Paula?'
'Because Stephanie, that is who you are.'
'Who I am? What if I say no?'
'Stevie, look at me.' I was looking at my plate. 'One of the things I admire about Joe is that he has a partner who loves to please him. Paula will do anything to please Joe you know'
'I guessed as much'
'Well all I am asking is for you to have some beauty treatments to make me happy, to please me. It is not all about you.'
'And if I don’t go, you will not be pleased, then what?'
'But you want to go, don't you, you want to see me pleased. Don't you?'
'Of course' I rather crumbled in the face of her emotional blackmail. I would be at the salon after work the next day, if only to please Helen.
The working day was not too productive, and when Paula met me outside work in her heels and a short dress I could just imagine what was being said by my colleagues. She kissed me on the cheek. 'Len rang to suggest I meet you here, make sure you don't get cold feet'
I was in the back room having a full body wax, while Paula was having her hair done. She says it is just so nice to have someone else fuss over her hair. It makes her feel special. I was not feeling special, I was feeling sore, as strip after strip was ripped off my skin. Rather thankfully this treatment took up all the available time before Clare wanted to close up. But she still managed to batter my male ego further, with the parting words of 'See you soon girls'. Paula just took my arm and walked with me to the car.
It was on the drive to her home and the subsequent coffee indoors that we had plenty of one on one time. Then I plucked up courage to ask about her transition. I asked the why question, and also how. To the why, that was simple. Joe wanted it. As a woman, she had felt restricted and somehow second class and wanted to toughen up her image. Then when she saw how easily Paul had managed to become feminine, Joe started to try out the opposite transformation. The how was more interesting, to me anyway. I knew it had started with the shows, but it took all year before Paul had been usurped by Paula. Like me, it had been shoe practice around the house, then a skirt. With Paula, it continued on from there, going out fully dressed, so she gained confidence being seen and taken for a woman. The argument was that this would help when on stage. There was also an increasing shift of domestic roles, as Joe worked longer hours and Paul did more housework.
I asked if she ever fought Joe over the changes. The simple answer was would I challenge Joe or even Joan? No I would not. But as it turned out, Paul had expressed concerns about what was happening, but being one of life’s push overs, had capitulated as soon as Joe asked. One such incident was the time Joe thought Paul should be wearing women's underwear 24/7. Paul did not see the need for this, but the next day all his briefs and vests were gone, replaced with panties and bras. And just before the Christmas party we went to, when he lost his job, Joe had expressed delight at the thought of Paul being home to keep house. So when Joe came home to find Paul dressed as Paul after a day job hunting. Paul was told not to bother. It was nearly Christmas, no one took on new staff. Paul had to agree, then Joe made it clear that if Paul was not going out to look for work as a man, then he might as well dress for the role he had been doing while not out looking for work. In other words, Joe wanted Paul to be Paula fulltime. And when I asked if Paul had not objected, Paula just told me that it was what Joe wanted, and that was enough. I concluded that Paul had become Paula basically to please Joe. Paula disagreed with this, saying that I was nearly right, except that she loved being Joe's wife and honestly can't imagine going back to being a bloke.
As our chat was drifting of onto less controversial topics like cooking, Joe came home in a suit and tie, which made me wonder if his workplace knew his true gender, as his look was very masculine. His first words on seeing me were 'Hello girls' then gave Paula a kiss and asked what was for tea. A minute later he asked how my salon trip had been. I said painful. He asked if I had been waxed. I confirmed his guess, then told me he could not understand why us girls will put up with such torture. Paula chipped in, telling him that we do it to look good for our men. I was not sure if she meant to include me in the we, but in that situation I certainly felt like I was Paula's girlie friend.
They tried to get me to stop and invite Helen over, but I made my excuses and left. I needed a break from Paula and her submissive attitudes. I got home quite late for me and Helen was already home and thankfully had started tea. 'Thank goodness you are home dear, can you keep your eye on this, I need to make a call'. And so what I at first thought was a return to the old routine, I was back in the kitchen being the domestic goddess. Later on she asked how the waxing had gone. I once again said it was painful, but she assured me it would be worth it and was going to enjoy checking out how nice my skin was later. I sensed I was going to be make love to in our new way again, and after all Paula had said, actually felt myself warming to the idea of me pretending to be Stephanie while Len pretends to be a man in bed. Later, I had to admit that the climax had been the best. Helen noticed and suggested I go to the salon more often with Paula if that was the result.
On Saturday, I saw some traits of Joe in Helen. Over breakfast, she asked how I would feel about wearing panties on a regular basis. So I asked why? Her reply was to say it would make her happy to think of me wearing such nice things, and just for her. No one else would know. I resisted, saying I would think about it. She calmly agreed to let me think about it, before saying that she was going to go shopping later and did I want to join her. I said no, there was far too much housework to catch up on. Which got a comment, something like 'Sometimes you are just perfect Stevie.'
Well, she did her shopping and came home with groceries as well as a New Look bag. 'Bought anything nice' I asked.
'Indeed I have, do you want a look?'
'I shall put the groceries away first'
'Maybe I should go and unpack these then' she offered without raising my suspicions.
'Ok with me, I am sure you will show me later'
'Oh I will' she answered.
The rest of the day was uneventful until the evening. We were going out with some old friends, so I had a shower before getting changed. It was then I found out that Helen had been taking tips off Joe. My underwear drawer had been switched for female stuff.
'Helen' I called
'What's up Stevie?' she walked in to find me looking at my drawer.
'This has to be you, I said I would think about panties, where are my briefs?'
'If we waited for you to think about everything, we would get nothing done. Someone has to make decisions, and at the moment it seems I am the only one capable' I was staring straight at her. 'And just so you don't have to worry yourself over any decisions, I dumped your old things on my way out earlier'
'But.........' I wanted to ask if I had any say in any of this, the words just failed to come out.
'No buts, I am going to love knowing that my sweetheart is wearing pretty things just for me'
Now don't get me wrong. I am not against wearing knickers, indeed I actually quite like the softness of the fabrics. Knickers are always the first garment I would put on when dressing and it was always a special moment. However, the thought of wearing them every day was daunting. Maybe just the risk of being found out and being called names which would call my gender into question. Whatever, I did not really have an immediate choice, and put on a white satin pair. Helen noticed the stirring the satin made to my penis, and nailed my brief wearing days firmly into the past. 'I see you like them as well, so you will not just be wearing them to please me' She gave me a big smile then stroked a finger up the length of my dick. My body denied me any decent reply, from that moment on I was a knicker wearer.
The evening out went fine and no one discovered my secret. But the day was not over. When we got home, my usual t Shirt and boxers had been changed for a satin sleep blouse and shorts. She got me into these by undressing me and then slipping the new garments onto my body. The satin was lovely, but it was a way for Helen to reaffirm my position in the relationship as submissive to her wishes. She followed this up by shagging me once more until I was worn out from my climax. I remember falling asleep wondering where my man of the house position had gone, and why was I giving it up so easily.
That weekend was a turning point. I had never seen myself as the head of the house, rather we were equals living together. From that moment on, Helen's attitude in many subtle ways made it clear that she was the one in charge. I could have my say, but she had the final word. Looking back, I had become a classic stereotype. The obedient wife, at least in the relationship, if not in outward appearance. I found life was easier if Helen was pleased with me, and would make sure she was happy to see me and be seen with me.
This change was first seen in the way I made efforts to keep the house clean, and have a meal ready for her when she got home, not great change there I know. Then after a few weeks and a few drinks with Paula, I once more plucked my brows, not too a thin line but into a neater and higher arc. She noticed immediately and let me know that I had pleased her. That to me was the point I became her wife, and she the husband, I had deliberately of my own volition done something to alter my appearance. I bought my own nightwear, knowing she would approve and emphasize my feminine role. I agreed to go to Clare's salon when my hair needed some tidying up, rather than go to my usual barber, where she cut it into a rather stylish pixie look, long wispy ends with plenty of length on top to gel into a volume look if needed. Helen told me I looked pretty when saw it the first time, and always encouraged me to keep it gelled up. Then I was enjoying a Saturday afternoon with Paula while our 'men' went off to watch rugby, and though it was not planned, we found ourselves looking in jewelers and I happened to admire some ear rings, meaning they would look good on Paula, and before I know it I am sitting in a chair, letting some girl fire sleepers into my earlobes while Paula bought the long chain drops for me to wear when my holes had healed.
It took a few weeks for the ears to heal. Then I tried the drops in and actually thought how pretty they looked, something I had never associated with myself before. This was followed a few days later by Paula inviting us over for a meal. She made it clear with the invite that unlike previous times, she was not going to be the only one dressing up. She expected us to make an effort as well. Helen took this rather more to heart than I did, and came home with a new outfit for the occasion. By this time, I was in a more pliable mood and when she suggested I dress up, I was pretty sure what she had in mind, but just to make sure asked her outright. It had been months since I had worn a dress, and she wanted me to wear the outfit I had worn for Jason. Knowing I would give in eventually, I teased her with questions about which tie I should wear with my suit, until she came out with it and told me to wear the blue dress. I was also to wear my new ear drops and to me at least, a significant booking with Clare who would style my hair ready for our night out. A very girlie thing to do, I realised later.
The meal was on a Saturday so I had time to prepare myself for this event. In the closet I still had my practice clothes from the show times and decided I should get myself mentally prepared for what was going to be a feminine day. So after I had finished the housework, I changed into a blouse and skirt, put on my plain heels, made sure the bra was not overstuffed, then did a simple make up job on my face, the lack of a beard was now a great bonus. I actually felt different this time. I was not dressing up to look like a woman, I somehow felt like a woman. Clare even took a second look at me when I walked in the door. She recovered quickly and smiled her welcome. Soon I was having a wash and dry, with the added bonus of her using a lightening pen that she stroked along some of the wispy tips, bleaching the colour out of my hair, making the long wisps more prominent.
Once home and with no encouragement from Helen, I plucked some more from my brows, then redid my face, added the drops, put on the blue outfit and went down to show Helen. She was dressed quite predictably I suppose, in a smart single breasted navy suit, white shirt and red tie. Then after our initial 'you look good' comments, she hugged me and told me she still thought I was beautiful in the dress. Then she took her wedding and engagement rings off. 'Swap?' I simply did as she suggested and exchanged my plain band for her decorative ones. I had to wet my finger to get them on as they were a little tight, but once on we agreed they looked very nice with my pink finger nails.
Paula squealed when she saw me, hugged me, called me Stephanie and pulled me through into the kitchen, where she handed me a glass of champagne and cassis. She was full of questions about every part of my outfit, where I had got things, how I had done others. The long sleeves looked great, but were not that helpful when handling food and in the end was told to sit down and pour out some more drinks and see if Joe and Len wanted another. They did and I simply refilled their glasses without questioning why I was behaving in such a way. Over dinner, I drank more wine, which added to the champagne meant by the time we were onto desserts I was quite drunk and relaxed enough to show Joe my wedding ring and the diamond next to it. Followed by a conversation about how pretty I was, and what a shame it was that I was unable to be pretty all the time. I actually told them I would love to be like that all the time, but I had to work as we needed my income. Joe said that was a shame and that maybe together we could sort something out. The meal over, we cleared up before going and sitting with our partners who were on the brandy again. Only this time I did not sit near Len, I snuggled up to her as Paula did to her partner. I felt ever so feminine and protected when I felt her arm surround my shoulder. And if you had asked me then to give up everything for a life as Stevie, I would have said yes without a hesitation.
But in the morning, when I was nursing a sore head and an equally sore arse, I had come back to reality and the need to be Steve at least a good part of the time. I still had a job to go to. After a slow start, I made an attempt to get myself sorted for work on Monday morning, but things did not go so well. My brows were again a little too thin for a bloke, and there was nothing I could do about them. I could darken the light touches in my hair. But one unexpected problem was the rings. They had been tight going on, now I could not get them over the knuckle, no matter how much water and soap I used. Helen was not as concerned as I was.
She kissed me, then said 'I suppose that makes you my wife still'. She did give me suggestions as to what might help, but they failed. I had already stopped suggesting she cook after we had an inedible meal she had prepared some weeks ago. But a deeper cut to my ego came when she came in and took my hand. 'Still on?' The rings clearly were still stuck. 'Looked nicer with the pink nails' she mused. 'I think this means we should keep on with our alternative names'.
'Stephanie?' I looked bemused, so she continued 'You are supposed to say, yes Len, at this point Stephanie'.
'What?' I was not really keeping up.
'Ok, let's make this plainer. I think of you as Stephanie, my partner who is more of a wife than me, and now she is wearing a diamond ring, something husbands don't do. All I am doing is using the names that fit the personality. I call you Stephanie or Stevie, you call me Len'
'Sorry Helen, oh I mean Len, where did this come from?'
'Last night you loved it, the dressing up, the girlie stuff with Paula, the being my woman, the whole thing'
I reflected quickly. 'It was a rather good night wasn't it.'
'You are still partly dressed as a female, aren't you'
I nodded.
'You are a better homemaker than I ever could be’'
'That's unfair, you were not that bad'
'I hated it. You love it' she paused for me to catch up 'You are now wearing the rings of a wife. I am wearing the ring of a husband. I merely want us to call each other by the names we used last night, and which suit our status in this relationship'
'You really think of me as your wife?'
'I do Stevie'
'Oh' . At which point a pan boiled over and I turned quickly to move it.
The topic was dropped as she said 'I like calling you Stephanie, and I would love it if you called me Len.' Then she walked away. She has never called me Steve since, even in public it was Stevie. If I call her Helen, I am ignored.
Fortunately she did not bring up that when we had exchanged rings we had used the words which included obey as the wife’s ring was given. That could well have been a hard hurdle for me to get over at that point.
Work on Monday was the usual teasing. Was I doing another fashion show? Some would ask if they could come, quite a few had come to the early ones and had had a good time. However, I now had to lie and put them off with tales about them being all sold out. The rings did cause some comment, especially when they continued to live on my fingers. 'It was a prank and they won’t come off' wore thin when I was still wearing them at the end of the week. Why do I not go to a jeweler and get them removed?
Two weeks later I was out shopping with Paula. She wanted us to have some 'girl' time together. This for her meant meeting at a coffee shop, then wandering around shops looking at the clothes on offer. I was careful what I said after the jeweler’s incident. Needless to say, I was not an unwilling partner when Paula was getting excited about the stuff we were looking at. She was picking out some really nice dresses and I found myself telling her they looked good but thinking 'would that look good on me?' Eventually the inevitable came. She picked out a plain white blouse, nothing different to my usual cotton shirt, just softer cotton and buttoned up the wrong way. I refused to try it on as I was too masculine at the time, but she bought it for me anyway. Then she bought me some jeans, tight around the arse but with a small flare below the knee. I did ask when I would get to wear them, she told me 'The next time we go out together at least, but they could be worn anytime.' We ended up at her apartment, and I tried them on for her. Luckily my manly bump at the front was still taped out of sight, which pleased Paula and made the front of the trousers lie flat as they were supposed to be.
There was a conversation about my lack of visible genitals. I explained how I had done it, to wear the dress.
'but that was two weeks ago!'
'It hurts to take it off' I defended.
'And Len prefers it that way as well?'
'Oh we are so alike. Joe can't stand to see mine, no sex for us when I am giving the skin a rest from the tape'
'Enough information, thank you'
'Len does look after you, if you know what I mean'
I was blushing partly because I was sitting in my underwear, but mostly because she was getting very intimate with my sex life. 'Yes we have sex.'
'Recently?'
'Last night, if you must know'
'Oh my god, how long since you used your dick'
'Paula, please this is embarrassing'
'No come on tell me'
'Six months I guess'
'It's great, isn't it. One of the first changes me and Joe made was in bed. I love it our way, never even consider using my dick nowadays. I even got a vibrator for if I want something in the daytime'
I changed the subject back to the jeans, but was once again amazed at how Paula loved her female role in life, and knew this was what Helen wanted for me.
A little later 'would you honestly be Len's wife fulltime if you could?'
'It won't happen. We don't earn enough, and I certainly could not give up my job like you did.'
'But if you could, would you?'
'I know one person would love that.'
'But would you?'
'I reckon it would be nice to give it a go, just as a trial, see how it worked'
'That is exactly what I said last year, now look at me sister' She ran her fingers through her hair for effect. 'I think we need to work on your hubby and get you fully wifed up'
'Please no, I am fine with things as they are.'
'You might say that, even I have said that in the past, but I bet Len would not agree. And I don't, besides I want a girlfriend who will understand what it is like.'
'I had best be getting home' then I looked at my new outfit 'I don't suppose I need to change, do I?'
'What!' She made some dramatic gesture 'you girl, are going home as Stephanie' I was then given access to her cosmetics and told to at least put on some lippy, and obliged with lippy, blush and mascara. In the meantime, she had been rooting in a cupboard and found some flip flop sandals she insisted I borrow for the journey home. Then transferred all my trouser pocket items into a handbag. Clearly nothing would fit into the new jeans, before being packed off without my old clothes.
To say my partner was pleased when I got home was an understatement. She told me I was being taken out that evening as I was, and that I should be going shopping with Paula more often. The night was finished with a predictable session of my not being allowed to rest until I had arched my back and screamed for more. Then concluded with her suggesting that Stephanie take a more prominent role in our lives, but without being specific.
Sunday, I dressed in a skirt for her and spent my day as I usually did on a Sunday, relaxing and cooking a nice meal. What I did not expect was for Jason and Sally to drop by. Helen answered the door while I was upstairs. She was looking quite masculine that day and I could overhear the conversation between them, which quickly got around to how she was dressed. Sally being particularly taken with the look. I was trying to make my mind up whether to do a quick change when Helen called up to me 'Stephanie, we have guests' I am sure the use of that name was to tell me how she wanted me to be dressed. So I made my entrance in the skirt. Jason smiled and asked if I was dressed for him. Helen gave him a look, and told him I was not, 'Stevie dresses like this because I asked him too'. I made everyone a drink and we settled down to chat, and after a long time of absence we had some catching up to do. There was so much that came out about Paula and Joe it was interesting to see how they reacted. Jason was clearly intrigued by the idea of men who look like women, but it was also clear that Sally did not want him going off investigating such things too often. Just as Helen had been jealous of me, Sally had realised how good Jason was, with the rider of 'No offense Helen'. They left and we all promised to keep in touch more often, but it had not been as warm as it used to be. That night out seemed to have upset our friendship.
Our burgeoning friendship with Paula and Joe was strengthening though. Paula wanted me to go shopping again. I tried to get out of it. I felt my masculinity being eroded far too quickly. But I could not say no without being rude. Needless to say, we ended up at her apartment which was nearer the shops. Only this time I was not taped up and relying on my knickers to keep everything in place. When she realised this, she told me she used surgical glue as it did not show or have the grubby edge as it ages. I still don't know why, but Paula ended up showing me her naked body and the benefits of glue, before getting me to strip and fix my genitals similarly. I felt quite different as the glue pulled on the skin in new places, but I would need to get used to it, at least three weeks she assured me. All I could think of was 'Helen, no Len is going love this'
I was right. She started to encourage me to wear more feminine clothes about the house before getting me to go to work in my less blokey stuff. I had always stuck with the stereotypical man at work style. Tailored trousers and shirt, but the office was rather more relaxed than that. Jeans were common and shirts casual if at all. I started with my white blouse. Soon I had another in ivory, along with linen trousers. Helen bought me some prettier studs with a green stone in them which I eventually wore to work. Another factor in my changing style was that the bleached tips that I had coloured over came back to haunt me. The colour faded, leaving the lighter flecks showing more clearly with each wash. It was gradual so I did not notice until it was pointed out to me.
Then came an unexpected call into the mangers office. I was asked about my changing looks and told that it was company policy to accept diversity in all its variety, as long as I did the job well and did not cause conflict in the workplace, I could dress how I wanted. This was then abbreviated. If I wanted to wear a dress then that should be fine, but could they have some notice if I was going to go much further with my feminine looks? I said 'ok' and went back to work. One thing I would not be doing was telling Helen, as she would have me in a dress if she knew, and I was not ready to face my colleagues in full female attire just then.
What I did not know was that Helen and Joe had been considering my future as well. As our friendship grew, it became clear that Helen got on very well with Joe and spent a lot of social time together. I would even say that Joe was a role model for the emerging Len. This friendship proved to be very profitable for us when Joe suggested Helen apply for a job at his firm. Four weeks later, Helen has moved jobs, got a decent pay rise and has taken on a far more business suit appearance, even day to day she is looking like a man with her neat short hair, dark suits and cultivated deep voice. Once the first pay slip had been banked, the inevitable conversation happened.
'I could support us both you know'
'But I like my job'
'But I don't like that you are tired after working, then doing the housework'
'I don't mind. I know you work longer hours than me so it is just the way it is.'
'So how about we reduce your hours?'
'You just want me to be like Paula.'
'And what is so wrong with that? You being a kept woman. I get my housewife, I think it would be great'
'Paula is not me, I like working'
'Not even to please me?'
'Please don't make me do anything. I am fine with things as they are.'
'Should I get all bossy and tell you to stop working then?'
'It would not work, you are not as domineering as Joe, and I have never been as submissive as Paula'
'In that case, I shall have to be more manipulative'
'Unfortunately, I have to agree, that is more your style.'
Paula was the one who created the next step in my move to fulltime. She had been to Elle's shop, goodness knows how much she gets off Joe for shopping, but it must be plenty. Elle had been staying in touch with all of us on a casual basis, and knew what had happened to Paula very well and me a little. She also knew I worked for an accounting firm, and was chatting with Paula as she tried on yet another outfit, when Elle's requirement for a book keeper came up. Two or maybe three days a week, she said. Well Paula told Joe, Joe mentioned it to Helen, who suggested we call round without telling me about the job. I had been persuaded to go in one of my plain daytime skirts so I would not look out of place and could try things on. I was in the changing cubicle trying on a bright yellow maxi dress when I heard Helen ask Elle about the book keeping job. I came out not only to say that I quite liked the yellow, but what job were they talking about.
'The one that would be perfect for you. Part time, same money pro rata as you are on now, staff discounts and a nice boss'
Then Elle joined in 'If what Len tells me is right, I think you would be able to do the job easily, and as an added bonus, you could come to work dressed in a style more befitting your looks'
'Did you know about this?' I was looking at Helen.
'Joe did mention it'
Elle cut in 'Look Stevie, I need a book keeper to do everything behind the scenes. If it's not the right time then don't worry. I will find someone soon I guess'
Back to Helen 'Stephanie, it seems like too good an opportunity to miss'
'And you can keep the dress if you say yes' Elle was not helping as the soft fabric was lovely on my nearly bare body.
'I am not sure' I dithered.
Helen stepped in 'You like the dress?'
'Yes' I replied. Then Helen turned to Elle 'You have your book keeper'
'But......'
'We shall let you know how long Stevie has to give notice for, then she can be all yours'
'What...' I was still unable to put a good argument together.
'You sure about this' Elle said to neither of us in particular.
'Don't worry Elle, Stephanie won’t let you down, will you dear?'
'I suppose not'
Elle gave me a hug and whispered 'You'll be ok?'
'I'll be fine, it's just a little sudden' then broke away saying 'This dress is lovely'
'Suits you, could you go braless?'
'I don't think so.'
Some five minutes later, we are outside and I accused Helen of setting me up again and just wanting what she wants. Then she turned round on me and said that part of being a wife is 'honour, cherish and obey' and though she did not want to push it, I was still wearing the diamond ring, and doing nearly everything a wife does. All she wanted was for me to look like a wife all the time and Elle would make that possible. The fight was ebbing from me. I was looking for excuses.
'My voice is all wrong'
'Paula's is much softer now, we could ask her.'
'I will need lots of clothes'
'50% discount'
'You will have to clean the car, put the rubbish out, unblock the drains and anything else I don't fancy doing'
'To get Stephanie full time, that will be worth it'
'I give in, you win'
'Great, let me call Joe, I think we should celebrate'
We ended up at the apartment drinking some champagne Len had bought on the way there. Paula made me try on the maxi dress, which got her approval, as well her encouragement to start with Elle as soon as possible.
I handed my notice in the following day. With holidays, I had less than a week to work. In the meantime, Paula and Len had gone into planning mode and had my life booked up from the day after I left my job to the day I would start with Elle. Clare got to do the full make over. I was booked in with a voice coach. Paula took me to buy some adhesive breasts. I went in the maxi dress so we could see what size looked good and stayed hidden. Paula also took it upon herself to take me clothes shopping, something she was always keen on doing. So by the time I turned up for my first day, I was in a grey suit with a flared skirt, cream blouse with a gold silk scarf, cream 4" shoes. My nails had extensions and shone with a glossy pink finish. My eyes had extensions on the lashes. My lips had a fuller look due to a liquid Clare coated on them. My hair was highlighted and feathered. My ears sported long gold drops which matched my bracelet and neck chain. Len had made love to me the night before while I wore a short baby doll outfit. I was as immersed in a feminine role as I could ever imagine. But the best part of it all was the pride that Len took in me as I left for work on that first day wearing a skirt. Well that, and a sense of it feeling somehow right. I looked to the world how I felt I should. A woman, doing a woman's type of work and being a housewife to someone that appreciates me.
At the end of Thursday, well about three actually, to be more accurate, Paula called to pick me up. She was in a flamboyant mood, wearing a brightly coloured floral dress with enough pleats to make it three times as much fabric as my plain brown flared skirt. I had settled on a thin knitted cardigan with a plain skirt as being most practical. Len had not allowed me to buy tights though, insisting on stockings. Then when it came to shoes, I wanted a low heel court, but was encouraged to get 3" sling backs. Next to Paula I did feel a bit dowdy, but she was not in a small office at the back of a shop. She took me for a coffee and wanted to know how everything had gone. I told her the work was quite straightforward, and I would soon have it sorted into a system I could follow. 'No' she sighed, 'how had my first week as Stephanie gone?' I thought for a minute, and then told her some aspects were easy, other parts hard. Remembering to answer the phone in a soft voice because they can't see me visually. Having to get up early and allow time to get ready. Not being able to wear the same outfit twice in one week. Having a randy partner who wants to have fun is tiring. Walking in high heels all day was making my legs ache. These were the hard parts. But the good parts must be better. 'Oh yes' and went on to tell her the fun I had working out what to wear each day. The joy of having to take time making myself look good in a feminine way. Feeling my legs hurting because I want to wear heels, knowing my legs look better that way. And having sex every night with someone who wants me no other way.
Paula was lapping all this up, 'not quite the same start as me, but it is exciting isn't it?'
'Yes I agreed.'
'And do you want your old job now?'
'I guess not.'
'And do you still want your shirt and tie?'
'I will need to think about that'
'Took me three months after we moved to the apartment and I went fulltime, before I had a clear out, or rather Joe had a clear out on my behalf. I just came home one day and it was all done. Everything that was connected to Paul and Joan was gone. No turning back, he said. Was such a relief in a way to not be able to think I could just go back if I wanted.'
'Oh, I thought you had been more committed from the start.'
'No, I was not that keen. I enjoyed the shows and it allowed me to express myself differently. No it was Joe who wanted this, I just had to do as I was told. I wish I had your flair for it though, you make it look so easy'
'But you are so pretty, and look fabulous all the time, why would you want to go back?'
'Don't get me wrong, I love it now, the fuss of being a woman, the pace of life that being a housewife affords me. I like being a kept woman as Joe calls it. But at first I was nervous of what people thought of me.'
'We all knew you would do whatever Joan told you to do. You did surprise us a few times, but now that I know you better, I can see how you were getting to know yourself better.' Then I picked up a bag and showed Paula the contents.
'A corset?'
'Yes, do you think Len will like it?'
'If he doesn't, I shall come round and make sure he is not ill'
'Well would you come back with me and help me lace it up'
'Most certainly sister. It shall be an honour to prepare you as Len's fantasy girl!'
And with that, we paid and went back home where we spent the rest of the afternoon corseting my abdomen and preparing me in anticipation of Len, my husband coming home for more than a cooked meal.
I came home from work, ready for a weeks holiday. I had a nice quiet week
planned, some DIY, some resting and possibly some dressing up.
All my plans were shattered as I walked in my front door and saw my
very determined wife, arms crossed in front of her, while she sat
in front of the computer.The screen showing what I had thought were
my private files, containing stories and fantasies about cross dressing.
She knew I had this little twist to my character. I had told her before
we were married that as a boy I had worn my mother and sister's clothes.
She seemed okay with it, even though I made it clear I did not feel it was
something that would fade away. Anyway, I was faced with a visibly upset partner
at that moment, and it was directly connected to my 'hobby'.
'So, you'd still like to be a woman?' she started in on me.
'You know I could never be a woman. I just have this desire to look like
one from time to time, wonder how the clothes must feel, that sort of thing'
I was defensive.
'Well, explain this then' and she started to read from the screen 'I knew
he fancied me because I could feel his dick stiff against me as we
danced,and not for the first time that night considered
if he would give me the pleasure of it in a more private setting' she
paused 'I could go on, but I reckon you know the rest, seeing as how you
wrote it'
My eyes were downcast, looking at the floor, anywhere but at her glaring
face.
'It is only a story, like James Bond is not a real spy, my stories are made up as well'
'Just a bit too much for me to handle, I am afraid, I am not sure I want a
man who even thinks what having another man shagging them is like.'
'Only hypothetical' I pleaded.
'Whatever, I have made up my mind. I am going to divorce you'
'What, no, please!'
'Forget your whining. I have decided I want out of this marraige.
Now, I spent today sorting out a few things and not just solicitors. But I am not
heartless; as a separating gift, I have set you up for a week as Mandy,
your femme name I think. A man named John is looking forward to being
your partner for the week. He only fancies trannies for some odd reason,
and can't wait to meet you'
'What......no, please I love you!'
'Forget it buster, I don't love you anymore and I doubt if you truly love me.'
'And if I wont give you a divorce?'
'You will, and you shall do everything I have organised for your
separation gift, or else I will site the reason for leaving you as being
the fact that you are a gay transvestite, and there are a few interesting
photos I found on here. You really should have been more careful how you
closed down this thing you know'
'But I am not a gay tranny!'
'I think you are, and that is enough for a divorce. Now do as I say and I
shall just say the grounds for the divorce is down to growing apart'
'Do I have a choice?'
'Well yes you do. Either I tell everyone you are a gay transvestite, or you
spend the next week as a gay transvestite and find out if you are one! I think
you could even say thank you for making this scenario avaliable to you'
'Please no!'
'Forget it! I have never been so determined as I am with this.Either
John gets his transvestite for the week or I get to ridicule you publically.
Now choose!'
There were no other options. She was right. I had thought about what it
would be like to have a man treat me like a woman in as many ways as
possible. I also hated the thought of everyone I know finding out about
my secret hobby. Defeated, I quietly said 'you win, what do I have to do?'
I was shown the spare bedroom and told to strip. There was a set of pink
sweats on the bed. 'Right, before tomorrow morning, you will have shaved
all over, rubbed in this tanning cream and read some of your more
graphic stories, so you know what might be in store for you'. I slumped
onto the bed as she continued: 'and tomorrow at nine, you will be waiting at
Transform, in your pink outfit there,' she pointed at the sweats 'for
the doors to open. I have given them a full list of everything, they
think, you have asked for. Got it?'
'Yes, but please?' I was cut off.
'I don't want you anymore. Maybe John will, if you treat him right.
How did you put it in one if your stories? 'I lay there feeling like his woman, and
I knew he was my man', maybe you can make it come true?'
'But I have only had sex with you, I don't know how to with anyone else'
'That is a bit weak after what I have read. With your descriptions, if
you have not been fucked, then you definitely want to be'.
Tears ran down my cheeks. 'Perfect,you're crying like a girl!'
I spent the rest of the evening in the bathroom, removing my body hair
and going to the kitchen to get something to eat, before being chased
back to the room. I slept fitfully, and could have been at Transform
well before nine, but she was going to take me and make sure I arrived.
And so I ended up embarrassingly standing outside a closed door,wearing pink
sweats and waiting for the staff. Her parting words as I got out of the car
were: 'Try and enjoy it, who knows, you might like it, and by the way I
have changed the locks at the house so that you can't get back in for anything,
until I meet you here in a weeks time! Bye Bye Mandy' I had not moved,
hoping it was all a joke, that is until she shouted 'Get out, you perv!'
Karen opened the door and welcomed me in. 'Mandy isn't it?'
'Yes'
'Come on in, we have an awful lot to do before John arrives' I was taken
through to the back, which resembled a woman's hair salon. 'Now let's
start with the body first. We need some new curves and to lose some old
ones. I am told you want to be as much a woman as possible, which for me
means, no dick!' I stripped off and meekly allowed Karen to do
whatever she intended to do. I had no fight left in me. First, she shrunk my
penis with ice water, then glued it backwards, with my ball sack making a reasonable
labia. Next, she glued some D cup breast forms to my small chest. After a
little make up on the edges, she stood me in front of a mirror. 'Say hello
to Mandy' Karen prompted. 'Hello' I said. 'Okay, breath on this inhaler'.
I took a breath. 'now say hello' I knew it would sound funny, because my
mouth tasted odd. 'Hello' it came out an octave higher. 'Perfect, you
sound and look like a Mandy now, follow me'. She gave me a luxurious wrap
to cover myself with and asked 'I am not sure what you and John are
planning, but from experience I find girls like you and men like him go
for one of three looks: a proper tarty style, a desperate housewives
look and sometimes the french maid. From what I can make out, you are
wanting to find out about being a woman, so how about a housewife look?'
I agreed, not wishing to walk out in a frilly maid costume or looking like
a whore.
I sat down and said little as i let Karen get on with her job. My floppy mop
of hair was styled into a curly blonde bob, which seemed to take ages. My
eyebrows were waxed into neat tadpoles, my lips were injected with
collagen to make them plumper,and my forehead botoxed.Before she put any
make up on, I was looking dramatically different. By the time she had applied
all of the cosmetics I was unrecognisable, what with my pink lips, defined
cheek bones and most amazingly, the blue contacts surrounded by bold mascara
and eye liner.
While my hair was being coloured, she had enhanced my nails into ovals
that doubled the length, then she painted them a rich pink to match my
lips. I felt she had about finished with the body and she would move
onto the clothes next. I was right. She took me through to the shop and
browsed the racks for something suitable. I remember feeling quite odd
as there was another man in there looking at high heels, which looked
kind of incongruous. Karen had made her choice for me. A white V neck knitted
top, and a grey soft cotton skirt. Once in the back room, I got dressed.
White satin bra and panties, tan stockings, just so he gets the idea I am not
a prude, Karen suggested, grey peep toe heels and a matching hand bag.
Then a few cheap bits of jewelry, a couple of rings, a watch, a big
bangle and a matching set of necklace beads which dangled into my
'cleavage'. Then she clipped on some pendants to my ears.
When I said they hurt, she suggested I let her pierce them, so I shut up
quickly. 'Right, something to make you smell even better, and a jacket' I
was declared ready, and was told to ring a number she gave me, with
instructions about what to say.
The ringing stopped. 'Hello, can I help you?'
'Is that John?'
'Yes, who is this?'
'Mandy'
'Oh hi Mandy!'
'Hi John, if it is convenient, could you come and pick me up'
'Of course, give me ten minutes'
'See you soon'
'See you, Mandy'
I hung up and told Karen that my ride would be here in ten minutes.
'Now remember, besides what you are wearing, and the make up in the
bag, you have nothing. So when John gets here, you will have to go
shopping for more clothes, underwear and night stuff, and if you need
any advice, give me a call, but after reading your stories, I don't think
you will need my help any more'. I blushed at the thought of her knowing
what I had written. 'I do like the way that your heroine is always
wanting to please her man. I am sure John will be very happy about that.'
'I suppose I should say thank you'
'I think you should. After all that has been spent on you, I expect you
to come back next week and tell me what a brilliant week you have had'
A man then walked into the shop, confident, smart,and six plus feet tall.
'Hi, I am John and have come to pick up a Mandy?'
I summoned up all my nerves and spoke up. 'Hi John, I'm Mandy'
'Wow Mandy, I was not sure what to expect with there being only some old
pictures of you, but bloody hell, you look fantastic!'
'Thanks'. I picked up my jacket and bag.
Karen gave me a kiss on the cheek. 'You go and enjoy yourself, Mandy'
'Thank you for everything, I think!'
I had had plenty of time to think how I would handle this meeting, so I
went with my plan as if it were a story. I gave him the bag of stuff
Karen had used on me, took his other hand in mine,and reached up to kiss
him. 'Right then, I am yours for the next week it seems.What do you
think of how I should look? I need some more clothes and you
could get me to wear what you like as long as it is legal'
'In that case Mandy, we had better get to the shops. Are you hungry?'
And so my week as Mandy started, with John keeping hold of my hand and leading me
out to his car. We ate in a nice cafe. Wine and a small pasta meal.It
was here that I had a few ground rules explained. If I did anything at all
blokish, John had been instructed to drop me outside of my wife's
solicitors. He also admitted to adding some of his own. I had to wear
skirts and heels all the time, because they looked good on me, and he wanted
breakfast in bed as well as all the other normal wife type duties I knew
would be expected of me. By this time it was pointless even thinking I
could rebel. Everyone I had met was in on my week as Mandy. I was going
to have to do it, but looking so good and being with a man who I could tell
was quite good looking was making the first day at least a lot easier
than I first imagined.
By the time I was ready for my new home for the next week, I
had bought, or I should say John had bought me, three sets of sexy
underwear, all lacy and satin. Two satin nighties. A plain cream dress
for daytime he said, a silver tube for night time, a long cotton dress
for going out in, and a pair of spike sandals. He showed me around his
house, then sat down to watch the TV. He had made some comment when he
showed me the kitchen about how it was my room, so when he sat down, I
took the hint and went to prepare a meal. I found everything I needed,
including a bottle of wine in the fridge and some candles that I lit
when I laid the table.
Meal over and the kitchen tidy, I relaxed with John. Thinking
what a woman might do,I sat beside him and put his arm over my
shoulder, then proceeded to finish the bottle of wine. It was not late
when John suggested we go to bed. I took the hint and went off to get
ready for my first ever night with a man! I cleaned my
face like Karen had told me, added another dab of scent and slipped into my
long white nightie, appropriate for the ocassion I felt, and went to wait
for my man in his bed.
We had kissed and cuddled prior to getting into bed, but I was just his
from the moment he lifted the sheet, saw the white satin and said 'you can only
be a virgin once'
'I know'
He then kissed and carressed me until I was aroused and felt my dick
straining against it's restraining tape,and soon found myself wanting to
feel his cock. Then, as if thinking aloud, he said 'I suppose we might as
well do this properly from the start, Mandy'
I just said 'Whatever you want, John'. At which point he lifted my legs up,
massaged some cream into my arse and pushed his cock inside me.
'Relax Mandy' he said a few times, then I felt him go inside and I
tensed up, breathing deeply. I relaxed and felt him moving in and out,
still tense, but willing myself to relax. I felt him getting deeper until
his balls touched my arse, and I thought 'my god how has he done that. No
more then'. I was even beginning to feel some nice sensations as he
pumped away, then he tensed, climaxed and relaxed.
He climbed off me, wiped himself clean, then after a quick peck on the
lips, said good night and fell asleep. Leaving me wondering if my arse
would ever feel the same, and at the same time feeling confused. I had
satisfied my man as I should, but I felt used because he had ignored any
needs I might have harboured. Then I felt the cum trickle out of me and
I made a quick exit for the bathroom. I was surprised to find a box of
tampax there, but relieved to have the oppurtunity to stem the dribbles.
Sleep was not easy as I worried about my situation, what John might end
up doing to me, what would happen to me when the week was over and I had
to face my wife once more. Would she take me back? where would I live?
how could I live as a man with such a feminine face, hair and nails?
Even if you think you are awake all night, somehow it is a surprise when
the alarm goes off to tell you that you need to get up. I had to be up
early so I had time to make myself look like Mandy before making John's
breakfast. I decided to stay in the nightie, brush my hair and have a
wash before applying some basic make up. For my effort, I was rewarded
with my second shag as a woman. John seeing me in my nightie said I
looked far too tempting and my arse moving around under the satin too
welcoming, and so for the second time in twelve hours I was living my
fantasy, as a man used my arse for his pleasure.
As I showered, washing off the sweat and other bodily secretions that
were on me, I considered if the discomfort I was experiencing in my
rectum was truly worth it. However, soaping my own breasts was a novel
and stimulating sensation that helped ease my concerns, followed by the
delights of having to make myself pretty and once more wear a dress (the
long cotton one) and heels without the aprehension of being caught in
the 'act'. And so I reconstructed Mandy for mine and John's pleasure.
After some housework, John told me as it was Sunday we should go for a
drive. A rather pleasant journey, followed by a nice pub meal, followed
by a randy driver stroking my leg, playing with the stocking tops and
tickling me between my legs. I in return tried not to get John too
excited and kept away from his dick until he announced 'It's no good'
andpulled into an empty car park. 'Right Mandy, get on with it' I was a
little unsure what I was to get on with, but he undid his fly and hooked
a ready prepared erection out for me. Still not sure, I massaged it then
thought of one of my stories, of being in a car with a handsome man.
I lowered my lips and kissed his tip, tasting the dribble of cum,
it twitched..I cupped his balls and ran my tongue around it, then took
it in my mouth, bobbing up and down, taking a little more every time
until it touched the back of my mouth. I gagged and slid off it, going
back down to the gag spot again and again making my tongue and lips
excite his flesh. I could tell he was enjoying himself, whereas I was
thinking this is getting a bit dull, when he tensed up and ejaculated
into my mouth. I had tasted my own cum before and knew it was salty, but
this was different. I had milked this man and the stuff in my mouth was
just for me, and it tasted great, especially with the knowledge I had caused
it's release. I licked him clean as he wilted, then sat up. 'Time to be
going, I think'. He did not reply and just drove the country lanes back to
his house where I made us a snack before settling down for the evening.
Before I fell asleep, I had a reminder of how I used to treat my now ex
partner. John was interested in some boring film so I gave up cuddling
with him and went to get ready for bed where I found a girlie magazine and
happily read it. Then while I am relaxed and half asleep, John came in,
gets undressed, climbs into bed and without much ceremony rolls me on my
back and climbs on top of me. Once he has spent his cum into my arse he
says thank you, rolls over and falls asleep. I once more make a trip to
the bathroom and plug my leaking hole with a tampon and return to bed
and hopefully a decent sleep before I am expected to be up first to make
his breakfast.
On the Monday, I fullfil all my duties and see him off to work before
getting myself showered and dressed. With the day to myself, I take time
to explore my make up options and oppurtunities. Discovering they are
quite limited, I make plans to improve my look and hopefully improve
my pleasure with John. I need to shop for some groceries, so a trip to
an anonymous Tesco is in order. John has left me some cash for food, but
while I am there, I see the clothes section and am tempted by a halter
neck mini dress. When John gets home, his house is clean, a meal is
waiting for us to eat and I am in my new dress and heels. I asked him if
he liked it, he asks what it is for, I tell him it is for dessert. He
smiles and gives me a kiss, letting his hands squeeze my arse and push
his erection into my body. Sure enough we had stew for mains, then for
afters I got a mouthful of cum followed later by a sausage in the hole.
This time however, I planned on being more in control. I made more of the
foreplay and once excited, asked him to make sure I had a good time.He
was in a mood to do anything and the more foreplay he got, the more
generous he was at promising to try and give me a good time. I had read
stories of how the 'woman' has a gland that if the man stimulates it
then an orgasm is possible. I was aiming on having John hit my spot and
I was not disappionted. I got some nice little tingles that left me
wanting more.
As I made him breakfast in the morning, I asked if he fancied going out
so I could wear the club dress. He said he would see how he felt when he
got home. So that evening, I greeted him in my short tube dress and after
giving him a nice long kiss asked what he fancied that evening. I wanted
to see what life was like as a girl at night, but I had to do it with
his consent. The hem of my dress rose over my arse cheeks and his
fingers ran along my crack. 'I have been stiff all day thinking of you'
he said, 'I also bought you a gift'
I put a hand on his groin. 'You are stiff, let me help you out' so I
released his erection and lowered myself onto my haunches and kissed it,
then with growing confidence and ease swallowed it, and found myself
looking forward to his explosion when it came.
'Something to eat, then I will take you into town and I can show you off
to some friends, but you will need to be on your best girlie behaviour,
we are going to straight places. Understand? I have not come out to
these people and if they suspect you are not a woman, I am in trouble'.
He gave me a stern look.
'I will do my best'
'Do more than your best tonight, or you and I are in trouble for
different reasons'
'Understood'
'And the gift, I would like you to take this and keep it in'
I gave him a puzzled look. I opened the bag to find a dildo inside.
'I hope it helps you find what you were looking for last night'
'Should I say thank you?'
'You can'
'Maybe later' I teased.
I put out the salad I had prepared and then went to make sure I was
looking my best.
'Will I do?' I asked, as I walked into the front room.
'Perfect, let's go'
He drove us into town and parked near a posh part of town. From here
we visited a few bars. John was on speaking terms with quite a few
people we met, apparently work colleagues on a celebration night out.
He bought me several vodka shots but stayed with fruit juices himself
as he was driving. I was doing my utmost best to be a perfect girlfriend
and the shots were making me unsteady, which meant I was holding his arm or hand
almost constantly. I even kissed him a few times as our faces came
close.
By the time we got home, we had been flirting with each other
for hours; meaning that when we got indoors and upstairs, I was
easily taken to bed and as he replaced the dildo with his cock, I felt
myself wanting this man inside me. He pushed in and out, and slowly I
felt the tension build until he pushed and I came, then I wanted him to
continue pushing until I subsided. Somewhere in my moment, I had been
filled with sticky semen, which now leaked out, so reluctantly I got up
and cleaned myself ready for sleep.
'Happy now?' he asked as I walked back in, wearing my nightie.
'Yes, and thank you'
I slept well that night.
Thursday morning was almost a routine by then. Breakfast, see him off,
shower, dress, shop, cleaning, lunch, rest and consider what I should be
doing as a woman etc. Only that day I had a new toy to play with, so as I
showered, I cleaned the dildo and with some gel inserted it inside me.
It felt like I wanted to use the toilet but with an extra sensation to
interest me. By the time I had eaten my lunch, I was feeling quite
excited and masturbated myself with ease if you consider how restricted
my penis was, it was a relief to cum and feel the pain subside.
I was wearing the halter neck dress when John came home.
'Good day?'
'Not bad'
'Anything interesting happen'
'Not much'. I could hardly tell him I had been playing without him.
'What's for tea?' he spoke as he wrapped his arms round me and let a
finger creep inside my knickers.
'Wraps'
'And what are you keeping under wraps down here?'
'Thought I would keep your desserts ready'
'Well how about we have entrees instead?'
'What?'
'I was just going to swap your fake prick for a real one'
'Oh'
He was holding me from behind and smoothly manouvered me onto the table
so I lay face down, then he just did his thing and I forgot all about
if the chicken would be over cooked as I urged him to find my G spot.
The meal was a bit dry, but the entrees had been delicious, later we
even had dessert before collapsing, exhausted, into bed.
Friday was like a new dawn. I had experienced the delights of being a
feminine partner in an apparently straight relationship, and after a
week of learning, I had come to appreciate that I could make a man happy
by the simple fact of making sure I looked good and letting him
think I want sex with him, which in fact was exactly what I also wanted.
I looked down on my sleeping man and decided I wanted a taste of cum, so
woke him up by stiffening him up with a blow job.
He went off to work happy and I cleaned his house for the last time. The
next morning, i would be going to Transform so I could be switched back
to my old male self.
That evening, I had prepared a special meal for him and wore the club
tube dress to impress him. Once we had eaten, it was still early and he
suggested that as it was my last night with him, he would take me
somewhere appropriate to my dress style. Soon after, I was teetering
along in my highest heels; being escorted down the city's streets to a
club that played dance music to an audience that I was to find out was mostly
gay and tv. I had a lovely time. John looked after me, while introducing
me to some of his friends, some male, while others I was not too sure
about, but guessed fell into the category that I was
currently in, gay CD. The evening ended back at John's with me on my
back, urging John to tickle my spot with his prick.
Saturday was always going to be a difficult day. My week's holiday was
over, my ex wife would be wanting to complete her worst punishment on me
and now I had found out that I actually liked the experience of being a
man's woman. But I would be required to give it up, so I could conform to
society and keep my job. I would, however, like not shaving every day at
least twice, but that was about it, I reckoned. I wore the long summer
dress that emphasised the bust and wafted around my ankles. On my last
outing as a woman, I wanted to feel as feminine as possible.
John did not rush to get me to the transform shop, he wanted his breakfast,
followed by a personal scrub in the shower, including particular attention to his
crotch area, which he insisted I wash with my tongue. So after all that,
we arrived late in the morning to be greeted by a smiling Karen who took
me through to the back room and asked how the week had been. I told her
it had been fine, but then she opened up her computer and clicked onto a
blog site, John's blog site! It took a moment to sink in, but John had
been publishing my life over the past week in quite vivid detail at
times. Excerpts from saturday: 'looks good, is very passable,
should be no trouble taking him/her out' and later 'few rough edges to
smooth off, should be a good week'. A few days later: 'keen to please and
I think she wants to be just taken and treated as a submissive girl'
followed by: 'she came last night for the first time, very keen now.
Loves dressing sexy for me, which is nice'
I was sitting back taking in what I had read, when Karen came back in
with a coffee and John and my ex! John asked 'Any problem
with what I wrote?'
'Bit public, isn't it?'
'Not really, only a few were reading it'
Then my wife chimed in 'Does seem like I was right, you did like being
the girl in a relationship'
Karen then asked if she would be needed to clean me up, but John and
Kate(my wife) said no, they would like to take Mandy out for a little
while to discuss my future..Like I wasn't there, I was sat down while
they talked over me. Karen just informed them the shop was busy, but she
had a slot at four when they could bring me back.
Being about midday by then, John suggested a quiet bar in town a few
streets away. Kate agreed and that was it. John took my hand and led me
out onto the pavement. We sat and ate a light lunch and drank some nice
red wine until about three. John talked about how I had risen to the task
of being a good wife and after a couple of glasses, I lost some restraint
and told them how much I had enjoyed my week as Mandy.
They even suggested I have electroysis to remove my beard permanently,
which I think I responded to more keenly than I should have.
We were back at the shop for four and Kate
had been talking about how I should keep myself pretty, but I was
resisting, thinking of what life was going to be like on Monday with all
the things she had done to me anyway. Then John suggested that if I did
not need to go to work on Monday, what then? I was thrown, I had to go
to work to earn money, but John persisted with the what if I did not?
I admitted that if I was not going into the office on Monday, then I
would not rush to be out of the dresses. But i followed it with the fact
that I still needed somewhere to live. 'But if you could forget all of
those restrictions, come Monday, would you rather wear a dress or be a man?'
'If I had another week's holiday, I would stay as I am', I concluded.
We walked into the shop as I was saying this. Karen said 'Hi, made a decision?'
'Yes' said Kate. 'Mandy needs her ears pierced and a course of electrolysis'
'No I don't' I protested.
'Why not, I have rung work to tell them you are resigning, and you need
to get away from clip ons and shaving, so what is your problem?'
'You rang work and told them I was leaving?'. I sounded horrified.
'Yes, the redundancy papers are at home'
'But I need somewhere to live, I need a job, I can't do that dressed like this'
John then piped up. 'I can see no reason why you are being so resistant.
Isn't it clear? I want you to live with me! I like the job you did
looking after me, and what is more, Kate here has come to see a new side
to you and does not want to be difficult. She says that she could do
with a house helper now that she is on her own'
Karen took me to one side, I thought to help me gather my thoughts, but
as the pain of a needle puncturing my earlobe brought me back to life, I
realised I had no choice other than to accept my female role until these
two stopped pushing me, or I got some strength and a plan to change back.
Which at the time I did not have! Come Monday, I was John's live in
partner and had a job as a home helper at my old house. All quite sudden, but
exhilerating, fun and definitely better than my old days of writing fiction
based on other peoples stories.
Truth for me was now stranger than fiction!
Being unpopular is not a comfortable feeling, finding friendship is always nice, but how far can that friendship be pushed?
The picture has nothing to do with the story, just thought some might like to a 360'rainbow seen on top of Snowdon
The school bus is a very good place to study the pecking order amongst kids, the popular ones sit in a big group with the most popular in the middle. This group are usually at the back, some nervous young girls occupy the front seats and in between are smaller groups, dating couples, best mates with a common passion usually computer related, and then there are those for whom social standing is possibly the hardest thing to work out. The brightest kids can sit alone on the bus because no one wants to be seen with them. Nial was one such kid he was seventeen and would have loved to be part of the back of the bus crowd but he just did not seem to fit in with them. And then there was Charles a fifteen year old who had suffered because of is name, lack of muscle and hieght, and his tendency to withdraw into his computer games.
In the years preceding their friendship really getting off the ground Nial and Charles had sometimes sat together if there were no free seats so knew each other a bit, both thinking the other a bit odd. But the friendship grew after Charles got a new game to play on his I-phone, Nial took and interest and they got chatting, soon Charles was looking for Nial on the bus it made him feel better to be seen with the older lad, Nial liked having someone about who actually wanted to be with him. They fed each others ego for different reasons which was fine. At the end of the autumn term they parted having remembered to say 'hope you have a good christmas' but Charles added an invitation to call round if Nial wanted, meaning it but not really sure if the invite would be taken up.
Christmas was as good as any teenagers christmas is, hard work, relatives, parents friends and trying to pick gifts for a few people. But there was the up side, the gifts they recieved and by happy coincidence both lads were in town spending there gift tokens, Nial on music, Charles on a game. Once they had what each wanted, Charles trying to sound interested about the music and Nial persauding Charles to get the game he liked, they made theie way back to Charles's home. After the introductions with parents, both lads disappeared into the bedroom to listen to the CD and play the game. Charles's mother popped in with offers of drinks and later to ask if Nial wants to stop for tea. Nial's dad is working late so he only had a frozen meal to look forward too so accepted.
In the main room while they were eating Nial noticed a picture of a good looking girl on the side board, after he asked if it was Charles's sister, it was not and an interesting story behind the photograph emerged. The previous haloween there had been a party at Charles's uncle's, everyone was to go in fancy dress, his dad had gone as a vicar, his dad as a nun, but Charles never quite got around to sorting out an outfit, so Charles's mother had decided a bit of humiliation might just be the best punishment for his lax attitude and made him go to the party in his older sister's dress she had worn to the school leaving party. Charles blushed for most of the time as his mother explained how she had made him shave his body, given him long finger nails, borrowed a long brunette wig off a friend, enhanced his chest with his sister 'chicken fillets, made him wear a corset to give him that narrow waist Nial could see. The dress itself was a burgundy colour, cross cut so it moulded itself around Charles's curves, the cowl neck exposing the lack of real cleavage, his bare arms had pretty bangles on the wrists, Charles face was beautifully made up, but for all the things his mother had done to him Charles's main concern had been the shoes, a 1" sole and a 5" heel, Charles said they were agony, his mum said they went with the dress as they were the right colour. Nial made some very complimentary remarks about how good Charles looked, his parents were very happy with the results and Charles admitted that the party had been good fun once he had got used to people calling him Charlotte, he had had his first taste of wine and though he did not know how to articulate had felt like he was being treated more grown up, but then he did look nineteen rather than fifteen. Nial thought his friend looked really good in the picture and said so, even going as far as to say he wished that he had a girlfriend who looked that good, there was some joking around Nial not having a girlfriend and his mum having no objections if Charles ever wanted to go to a fancy dress party again in a skirt. Charles was embarrassed by all this chat about his night as Charlotte but inside he remembered the time with fondness, it had been fun, different and enjoyable in an odd way he could not understand, and then listening to the talk he felt pride that he looked so good Nial would fancy that girl in the photo.
The friendship continued as they played games and listened to music together, Charles's parents were not too concerned that Nial was two years older after they saw the lads were getting on so well, seeing it as a good thing that Charles finds friends and gets out of his bedroom. Nial after the start of the next term saw something else though, he was reminded that he was not one of the lads who was in with the main crowd and that he longed to be a part of that group, he had one friend and he was two years younger, how sad is that. What Nial thought was that if he could go to the school dance with a good looking girl, then his status would improve and he would be accepted into the group he felt excluded from, and after seeing that picture of Charles he thought he might have found a way to have a girlfriend for the dance, his one problem was that Charles was a lad who showed no interest in giving a repeat performance. So he decided to bring the subject up as often as possible, flatter Charles, tell him how good he looked and how much fun it must have been, and look for a way of persauding him to do it again. Charles not being used to praise lapped up the compliments, but quite seperate from the dressing up chats they both found that they would like to play a joke on the kids who never seem to include them in their activities, unless off course it is to tease them. This was Nial's oppurtunity, 'what if' was his ploy,at the school dance no one expects me to go this year, least of all with one of the best looking girls, be one up to us. Be such a buzz knowing we had gone looking like a proper hot couple, while all the time it is just us mates having a laugh at them for being so hung on appearances. Nial thought was a great idea, Charles less so, the party had been family, they knew he was not a girl, like they knew his mother was not a nun, but to go all out and pretend big time he was a girl, if it went wrong it would make his life even more difficult. Nials answer to this was practise, Charles could go round to his house almost any day as his father worked long hours leaving Nial increasingly in charge of the house since his mother had left for another man twelve months before. It only took a fews days of concerted pressure for Charles to give in, he did not want to loose the friendship and Nial was getting more grumpy with him, but as soon as he had agreed Nial was back to his normal friendly self, well as friendly as Nial ever could be. Charles first step towards being Charlotte again was to borrow/steal some clothes from his sisters bedroom. There was not such a big chioce because she had taken most of her stuff off to college,but to Charles there was more than enough to get him started. He picked out a plain white blouse, a nothing special blue skirt, a pair of tights and because there was no chioce a pair of black heels. Then concealed in his back pack he went round to Nial's.
This was going to be the forst time Nial would see his friend dressed as a girl and he rather overdid the expectations, he had only seen the picture and that was what he thought Charlotte would look like, He hid his disappiontment well when Charles walked in only having changed his outer clothes, he looked a bit like a girl but it was Charles in drag. It was Charles who spoke first, 'This is not going to work, I will stand out like a nun in a brothel' but Nial was not giving up that easily, he wanted at least once people to look at him and think 'wow', not 'oh it's him'.
'Ok it is not perfect, there are a few things we need to work on, but you do look half decent and there is always the photo to remind you how hot you can look'
'Maybe I should ask my mum for a bit of help'
Nial was not too sure how she would react, it might be negative 'Let's see if we can't work it out ourselves, my mum left tons of glossy magazines behind, and there is the internet to look on, come on be a bit of fun finding out wont it'
Charles was gee'd up by Nial's upbeat attiutude 'Ok let's have a look then'
Charles went to change but was persauded to stay in his sister's clothes while they browsed the internet. They learnt alot that evening, and not just about the art of dressing and how to make a boy look like a girl ! Combined with this new knowledge and Nial taking a look through the stuff his mum had left behind and his dad had just bagged up for the tip but never got round to taking, he found lots of Vogue and Cosmopolitian magazines plus to his amazement some packets of pills. After Charles had changed ready for his walk home they sat and discussed what he needed to find for next time, a bra was essential, the fake breasts would be good, nice tights, stockings would be better and maybe the corset, plus any make up he could find.
It was Saturday afternoon that Nial welcomed his friend in once more, this time with another bag full of stuff, Charles had found everything on the list but it had not been easy as his parents did not go out for long that morning and it was a bit of a rush to check everywhere. Nial was so pleased when he saw the contents, Charles went into the bathroom to change, he had the bra and knickers on (black and shiny) but the corset was needing an extra pair of hands so walked out in the undies to a stunned Nial, 'Will you help me sort this out please'
Having stopped staring 'Off course dear'
Soon the corset was wrapped around his waist and the stocking attacked to the clips, Charles then slipped the black heels on and walked out to ask for a hair brush.
'Fuck me you are looking great, here I have a brush' Charles walked off and played with his longish hair hoping to recreate any one of the styles they had seen in the magazines, he went for a side parting and covering his ears style, then he tentatively put on lip stick and a brown eye shadow before going out to see Nial.
'Even fucking better'
'Look Nial, this is not at all easy or comfortable so please stop swearing'
'Sorry Charlotte' started Nial 'you even sound like a Lucy telling Jasper off for his bad mouth'
Charles blushed as he realised what Nial was saying. They spent the evening eating pizza, drinking coke and looking at more websites, some cross dresser, some gay but not many and plenty of fashion sites looking for what Charles might look good in for the dance. Time passed quickly and soon Charles was needing to change to get home. This time he left the clothes behind so he had less risk of being caught with them on him. He was back the next day dressed in his underwear and heels, Nial said it would help him feel more girlie if he did so. For the next week every time Charles called round at Nial's before they turned a game on he would get changed, then go and sit with Nial and play their game.
After a week Nial felt his friend needed to be encouraged to act more like a girl, when in his sexy outfit anyway, so he would make comments if Charles sat like a lad suggesting he sits more upright, and more to reinforce his male dominance he would ask Charlotte to go to the kitchen and get him another drink, without realising it Charles would just get up and do as he was asked. Another thing Charles did not realise was that the pills Nial had found were hormones and Nial had done his homework, they were a sort that boosted female hormone levels and trans sexuals used something similiar to get their bodies to change, so Nial knowing his friend would not willingly take the drugs would crush them up and add them to a drink he made for him while he was getting changed. What Nial was hoping for was some real tits to start growing because a low cut dress in his eyes was always the best.
A month went by, Nial and Charles sepnt there free time together pretty much as the had done before christmas only then Charles was spending time changing first before getting down to whatever they had planned for that evening, sometimes games, sometimes chilling listening to music, even doing homework. And in all this time Nial's father never came home early and surprised them.
Nial is very careful to flatter and compliment Charles as much as possible, especially when Charles tries something new or different, maybe a different lip stick or foundation for the first time, Charles is very self critical as he knows if he is rumbled his school life would be hell, so he makes a big effort to learn how to do his make up, walk in the heels, sit like a girl, make hand gestures like a girl, he even considered how a girl would eat when he was with Nial. Once he had spotted something that he wanted to copy and he had mastered it he would notice something else as he watched the girls around him at school.
Nial had more money than Charles and the first time he did it he was terrified someone would shout out 'you boy, what are you doing' but it did not take long before he discovered no one really bothers if a lad is buying women's clothes, The first thing he bought was a black blouse he saw in a shop window, sheer body and sleeves with satin cuffs and collar, he was not sure of the size but guessed, the shop assistant siad as a joke it was a little small for him, but Nial just told her it was for his girlfriend, which was nearly the truth. Charles had borrowed a black leather skirt from his sister's room and Nial knew this would look great together. That Saturday afternoon he gave Charlotte the blouse, suggesting he wear it with the leather skirt, prompted by this gift Charles did his best with make up and hair before joining his friend in the living room.
'Don't swear'
'Spoken like a true girlfriend, you do look f'king great though, that blouse is so sexy'
'I know you can see my bra can't you'
This however was the first night Nial's father decided he should come home and see how his boy was getting on, or maybe he was just not feeling to well, but he walked in to find 'Charlotte' in the kitchen getting a couple of drinks.
'Oh hello' he amnaged before Nial walks in behind him.
'Dad meet Charlotte. Charlotte this is my dad'
Charles was ready to make a run for it, but where to. 'Hello Mr Riley' and picked up the glasses ready for taking them through to where they had been sitting.
Over his shoulder he heard Mr Riley say 'bloody hell son, that is one hell of a cracker you have there, hot or what?'
Nial joined Charles and told him his dad liked Charlotte, Charles told him he had heard what he said. There was then much nervous talk about how Charles was going to get home, he could hardly change and walk out as a boy, he would have to leave in the skirt and change somewhere on route. This also meant that Nial had walk his girlfriend home. They got a route planned that went behind some shops and was a quiet area, so after a short while they left for the walk home. Charles had chosen the highest black heels with a silver spike heel to wear that evening not expecting to have to walk that far, but there was no way out of this problem he had to leave as Charlotte or be found out. With a back pack of regular boy clothes he left with Nial by his side, holding his hand, for effect Nial said. It was about half a mile to the shops and it was quiet round the back, So even though it meant stripping in the open, Charles undressed quickly and put his boy stuff on, brushed his hair out and then realised his face was still made up. He panicked but Soon accepted there was only one way out of this, slip in the back door, shout good night, shot upstairs to his room and wash his face once behind the locked bathroom door, not coming out until it is clean. Simple. Surprisingly that is how it happened, and he found himself in bed still hearing his pulse pounding in his ears after a quite extra ordinary evening.
The next day a quick text, 'need a rest, that was frightening last night, see you in the morning'. This gave Nial and Charles time to consider what was happening, Nial was over the moon, he had got home to be given a beer and slapped on the back, accompanied by comments such as 'well done son'. His dad had noticed him and more than that had approved of his 'girlfriend'. What was more significant was that his dad had meet Charles ocassionally but never connected Charlotte with the boy who came round to play games. Ther was also the matter of holding hands, that had felt so good, it felt right and somehow he would need to get Charlotte to be more affectionate, like a real girlfriend would.
Charles was not looking for the positives he was still smarting from what he considered nearly being exposed by Mr Riley and then getting caught by his parents. By the time he met Nial on the bus he had reflected enough to realise that Mr Riley had not seen through the disguise, Nial had looked after him, like a boyfriend should,and no damage was done. Nial was the one to ask if he was coming round that evening, Charles said he was not going for a repeat of Saturday but he would have some time for a bit of practice time, which meant walking in heels and watching some youtube clips, then trying to copy the actions. This however could not be done just wearing heels, Nial always liked to see his 'girlfriend' if not made up then at least dressed. That night however he pushed his luck to see if Saturdays adventure had damaged Charles's confidence any. When Charles was changing Nial suggested he just wear bra, corset, knickers and stockings, so he can look and feel sexy as he struts about. Charles did not question the request and gave Nial one his best floor shows ever as Charlotte walked around the house while Nial watch film clips and Charlotte, then making comments on how to improve the posture or whatever they were looking at.
The next Saturday Nial follows through on a seed he had planted mid week, that as a couple they should be more intimate together, the girl should be more affectionate than Charlotte currently was, so he suggested in the interests of authenticity, when Charles is Charlotte they should try behaving like a couple, 'as in kissing?' Charles asked. 'Would look the part' Nial countered. That evening after Charlotte had been to get some drinks, he came back to find his friend sat on a settee and inviting him to sit beside him. Over the next hour they try out holding hands while they watch the TV, they move onto a cuddle Nial putting his arm around his friend's shoulders. Then when it is becoming time for Charles to go home, Nial suggests one last thing, Charlotte asks what, and in reply Nial leans in and kisses his girl on the lips.
'Not so bad' Nial ventures
'Maybe not, but you do need a shave'
'Besides that are you ok with it'
'It will look better I can see that, but I had thought I would have my first kiss with a girl'
'Sorry about that, I shall try to make times together as pleasant as possible'
From that day on when Charles had emerged as Charlotte, Nial would greet his girlfriend with a kiss, the same before Charlotte went to change back. This would always happen, but as the days passed they found it easier to touch each other in more and more affection, this at Nial's prompting should come from Charlotte as she is the girl therefor more affectionate by nature, or so he believed.For Charles part he has not had much close contact with his parents and even though they are only role playing he does enjoy the closeness when they sit together or cuddle one another in the kitchen, resting his head on Nial's shoulder becomes a natural postion to take, and one Nial is not complaining about, he too is liking they way this relationship is going, at first he just saw Charles as an easy way to get a girlfriend to show his peers that he was not such a loser, but as they spend more time together the bond is growing stronger.
By the easter break Charlotte is growing more confident after the incident with Mr Riley, and the introduction of intimacy has meant something deeper is developing. Charles is lying on his bed considering how he had ever got to a position where he would actually look forward to going round to Nial's and not just to hang out with a mate but to be a pretend girlfriend. What was special about that morning was that Mr Riley was working away for a couple of days and so Nial had invited Charlotte, and he was specific about that, to come and stay. Charles parents were fine with the arrangement, Charles was nearly sixteen and had to be trusted with more freedom they concluded just like they had loosened the ties on their daughter, so they would need to do it with their son, and Nial's is not that far away if anything happens. And so with their blessing and a few pairs of borrowed knickers Charles made a surprisingly excited walk to his friends house. Mr Riley gone, Charles sneaked in the back door and into the spare bedroom he now called his boudior. It took a good hour before he was ready, after much deliberation with himself about how far he should go he finally plucked up courage and plucked a few eyebrow hairs out of his face, the paln was to pull out a few each week to make them neater so by the dance they look better and no one noticed the change. For daytime Charlotte wore a plain knitted top and short skirt Nial had bought her the week before. After emerging as Charlotte they had their now familiar kiss aand Charlotte looked about for what there was to do for the day, it was going to be a long time just sat about watching TV. It took about an hour for Charlotte to get bored and go into the kitchen and tidy it up, just for something to do. Then as it was a nice day and Nial had been left the car he suggested going out for a ride, the reasoning being that Charlotte needed to be used to being out in public so come the big day the outside world is not quite so daunting. This was not a situation caused from desperation like the first time, so there was time to get anxious, a short walk to the car, then a paraniod sideways look at all the other drivers to see if anyone is staring at them, it took half an hour to arrive at the out of town shopping centre, no one they knew would be there so it was safe. And after an hour of window shopping Nial suddenly grabbed her hand and walked her up to a cosmetics counter, this is what his mother''s job used to be so he had heard about the make overs designed to sell products. Charlotte after the shock was put at ease by a nice girl called Debbi who cleansed and took Charlotte through the various stages of make up. When Nial returned Charlotte was truly made up, eyes a sultry shades of green, cheek bones to give definition and pink lips which looked so moist as to make you want to kiss them. Nial paid for a selection of the products and was surprised to find a hand in his, he looked round to be told 'Well isn't that what a girlfriend does to a generous boyfriend?' They walked some more and ate some lunch before heading back home.
Charlotte was growing in confidence all the day and suggeested stopping at a supermarket to pick up some pizzas for tea, and with hardly the bat of a mascaraed eye lash she got out and went to buy what was needed. Nial was most impressed. What impressed him even more was that while the pizzas were cooking Charlotte went into her room and changed into the see through blouse and leather skirt, coming back in time to serve the meal and get a 'wow' of approval from Nial 'maybe I should take you out more often'
Then Charlotte with a coy smile replied 'Maybe you should, today was quite exciting'
The evening ended with them cuddling on the settee before finally kissing properly in what could only be called a snog. There was one final treat / new experience for Charlotte that day, Nial had bought her a long red nightie while she was having the make over and now was the perfect time wear it. Hot said Nial, lovely feel said Charlotte. And then went off to the spare bedroom and a routine of cleansing the beuatician had recommended.
The next day went pretty much the same. Get up, dress, eat, get bored, do some housework, go out in the car, come back cook a meal, cuddle up in front of the TV. They were both relaxed and Charlotte felt it was a good time to tell him something.
'Don't laugh, but my nipples have gone darker than I remember and if they weren't so soft I would say I am developing nice pecs, do you think this dressing up is affecting my body so it looks more like a girls?'
Nial had longed to hear this but played it cool 'That is interesting, do they feel any different?'
'Well yes'
'And how big are they?'
'About this big' Charlotte pointed with a finger.
'Could I take a look?'
'Why?'
'Because I'm curious'
Charlotte started to unbutton the blouse and then took out one of the false tits and pulled the bra cup down. Nial looked on in wonder, he had only seen breasts in pictures and now even though it was small Charlotte definitely had small breasts.
'They look real, can I touch it?'
And without waiting for an answer stroked it with his finger tips, Charlotte took a sudden short breath and the nipple hardened.
'Oh my god, that is so sensitive'
'And nice by the look on your face'
Nial stroked it again and squeezed the now erect nipple.
'Stop it Nial'
'Why you seem to like that. I think we can safely say that for some reason you have breasts.'
'do you think they will get any bigger, be so embarrassing at school in the changing rooms if I had some real big ones like the real girls'
'How should I know' and with a shrug 'can't imagine them getting much bigger that quickly, takes years for girls to grow theirs. Don't worry about it, you'll be fine' But before he had finished the sentence he was considering doubling the dose of hormones just until the dance so Charlotte could have some cleavage.
Nial had kept his hand on Charlotte's bust all the time, and whe he finished talking he kissed her lips, massaging the nipple at the same time. Charlotte opened her mouth slightly and leaned back as the pleasure of his massaging took over. More kissing and fondling until Charlotte, because Charles would never say this.
'Nial this is wonderful, have you any idea how nice this feels'
'I can guess from your expression'
Eventually late into the night, both worn out they stopped their intimate touching and went to bed, alone.
The next day would be their last full one together and Charlotte with a little encouragement wanted to go shopping. In magazines they had seen bras which are well padded and push what little there is up and into a cleavage, Charlotte was not sure this was necessary but Nial wanted to see if such a garment could be found. After much looking and many awkward questions about Charlotte's actual size, Nial parted with some more money and Charlotte had her own tiny breasts being pushed together. Nial had given her three pills that morning and just hoped for some quick growth over next couple of months.
As they sat cuddled up that evening, they admitted to each other that they not only felt they looked like a couple, but somewhere along the way in creating that look they had actually become a couple, Nial said it was when she wore sexy outfits that he really fancied her, For Charlotte she reckoned it was when she told him to shave and he did and still kept himself smooth lipped just for her.
The last day they just cuddled, Charlotte delighting in how her nipples tingled at his touch, but was not so sure about the hard dick she could feel at times pressing on her leg and knowing what the lad was feeling. Unexpectedly Charles was exhausted by his longer period as Charlotte and combined with feeling down once he was back in his own bedroom, the next few days were slow and dull by comparison.
During the holiday Charles had time to dress more completely than during school time and made the most of the time to practise make up, walking and cuddling in particular, but once the school was back in there was not the time to do a complete transformation knowing it would take too long to dress and clean up after, but even Charles felt changing his clothes, brushing his hair and putting on lipstick was at this point just not satisfactory. So Saturday afternoons became his transforming time, Nial had a Saturday job, the house would be empty, Charles's parents did not mind him being out most of the day not coming back until late, this gave Charles plenty of time to get ready and then play the housewife for Charlotte's boyfriend, Nial Nial got caught up the romantic idea of him being the man, coming home from after a hard day at work to find his 'wife' dressed up to please him and a meal on the table. There was even one or two stop overs in the weeks just after easter which made the fictional romance even better.
Nial was working on the next stage as he saw it, getting Charlotte to relieve the pressure he was feeling in his cock when they were cuddling. This was surprisingly easy to find the trigger but not so easy to put into action. Both lads were pretty much outsiders to the main mating games that went on, and there knowledge of what went on was from overheard conversations, mostly from bragging boys who Nial and Charles actually believed, when they heard that so ans had slept with sos and so they never stopped to consider if this ugly boy could possibly be attracted to the schools hottest but most careful girl, to them it must have happened. So one evening on the bus they heard an often bragged about story concerning the upcoming dance, notably the post dance activities and how the lads talking were going to have a post dance party at someones house with the sole intention of getting their girlfriends to have sex a blow job being the least they expected of their girls. Like I said both lads were niave enough to believe that after the dance every couple would be having sex and this created a problem for the Nial Charlotte couple, how do they have sex? By this time in their relationship both had read enough on websites to know that ladyboys can satisfy a man's needs, but they had only considered looking like a couple, what if they got invited to a party, they would expected to have sex. This had differing responses from the two lads, Nial could see the oppurtunity to have some sort of sex with his girlfriend, Charles even as Charlotte could only imagine what that might mean, one being gay sex with Nial pushing his dick up his arse, the other being getting up close and touching the dick with his mouth. Nial spent several evening bringing the subject up but Charlotte was being resistant to the idea of sex, then on the Saturday Charlotte is dressed in a blouse unbuttoned to show the embryonic cleavage and Nial in the cuddle has his had inside the bra making Charlotte breathe more deeply, he took his chance and guided her hand onto his bulging pants, Charlotte knew what he was doing but the pleasure from the nipples was overriding all previous agruments, after an initial resistance she relaxed her hand and from outside the trousers cupped and massaged Nial which she could tell was having a similiar effect on him to what he was having on her. With youth comes a lack of control and it was not long before Charlotte was holding a shrinking erection in a damp pair of pants and Nial after being so excited was now laying back exhausted. Saying things like 'brilliant' and 'fantastic'.
When he was cleaned up and in dry clothes and relaxing with his arm around Charlotte's shoulder his hand slipping inside the blouse, he makes the comment.
'I think you enjoyed that?'
'Only trying to repay you for the pleasure you give me'
'But you were really good, like you really wanted it yourself'
'Maybe'
'Would you do it again'
'Maybe'
'Would you put your hand inside next time'
'Err maybe'
That was enough for Nial, he could see the resistance crumbling.
There next time together was a Sunday evening, but the reason for that time as Charlotte was so Nial's father could meet Charlotte properly, he had been told she was the date for the dance and Mr Riley fancied another and longer look at his son's chick. She was there when Mr Rilley got home, mid afternoon, she had gone to alot of trouble to dress up, corset and fitted top to show off the figure, short skirt to show off the legs, high spikes to show off the ankles. He took them out for a pub meal, bought Nial a beer, well he was nearly eighteen, and enjoyed the company of the two teenagers, but he was having trouble keeping his eyes off Charlotte, which made Nial ask her to tone it down next time to stop his father being a letch and staring. This incident and being asked to be more conservative told Charlotte that she was attractive to men and not just Nial. Later when it was getting time for Charlotte to make her escape they are having a cuddle in Nial's bedroom and she tries something out on him.
'How much do you like me?'
'Loads'
'Enough to treat me?' she slid a hand onto his dick which hardened immediately.
'I buy you treats already, all that make up remember'
'Well yes, but what about the future?' she moved her hand from outside the trousers to inside and tickled his dick head.
'Ohhh' was all he could say
'A girl needs to know her man will look after her you know' the fingers went a little lower to the base.
'I will Charlotte'
With that she closed her lips on his and kissed him letting her fingers wank his dick until the sudden wetness told them both he was spent.
'Now then remember what you just promised'
;I will don't worry'
'Now we had better think about walking me home lover boy'
Getting out of Nial's house was easy, getting into Charles's was as fraught with danger like the last time, but it was handled well and Charles was in the bathroom cleaning up and into bed without his parents being any the wiser.
During the week even though Charlotte was not fully made up they still enjoyed a couple of erotic cuddles, Nial was letting Charlotte get comfortable wanking him before he pushed for the goal of a blow job which seemed a minimum for a party. He had bought her a new top and another short skirt for the weekend and left them out so they would be found when Charles came round in the afternoon to get ready.
'Did you like my treat?'
'Yes but it is for you to look at as well isn't it?'
'Well yes, I like you looking sexy, but you also like looking sexy don't you?'
'It pleases you, so it pleases me'
Nial kissed her, 'What do you fancy doing tonight?'
'Anything in mind?'
'I was given a DVD at work, could watch that' which was not quite the truth, it was a rental DVD that someone at work had recommended.
'Ok, let me finish the tea, we can watch it after that'
The film was really a soft porn romp, nothing too graphic but enough so you could tell what the couple were getting up to. It had one scene where the man is trying to talk on a phone but the girl teases him first with kisses on his neck, then stroking his body until she reaches his trousers, a few strokes there before undoing the belt and zip, all the while he is trying to talk to his mother, then with the erection in full view a few teasing strokes and a wicked smile as she licks his tips, more struggling as he tries to control himself, then she kisses and swallows the head, he can hardly talk but you hear his mother say 'Ryan call me back when Suzie has finished' and with that he puts the phone to one side, and gives in to the woman's teasing and comes.
'You want me to do that don't you?'
'Well it does look really good'
'For you'
'And I have bought you treats'
'Maybe'
'And it would look bad if we get invited to a party after the dance and we are the only couple who don't do it'
'Yes, that is on my mind'
'So should we try'
They got themselves in the mood with some erotic cuddling, Nial with a hand up the top and the bra unclipped so he could feel the now definite small breasts his increased hormone does had created. It did not take long before he had undone his trousers and let her see his prick, trying to recall what had been on the film, she stroked it, making it twitch, then with Nial's encouragement she touched the tip with her tongue, it twitched aand she jumped, 'put your lips around it' he urged, but she used fingers instead not enjoying the sensations as much as him, 'Oh Charlotte this is wonderful, go on, just try it' so she moved closer and tasted the pre cum, bit sticky and salty, then her tongue stroked the throbbing vien and Nial tensed, realising how she was able to tease him, she sucked the end like it was a lolly pop, another tensing, 'Oh hell Charlotte don't stop'. A few more sucks, licks and stroking around the base and balls and Nial was helpless to prevent his best ever orgasm, he fired it into her mouth, she was not expecting it and moved getting the next shot on a cheek.
'Oh my god Charlotte that was the best. You are the best'
'Maybe'
'No you are, that just blew my brains.'
'Mine never gets hard now you know'
Nial took a moment to take this in, 'I had wondered why yours did not show' then with a smile 'You can always play with mine if you want too'
'Not quite what I was thinking but thanks'
Nial was calming down by then 'Was it bad, kissing my dick?'
'Not the nicest thing I have put in my mouth'
'Would you be up for it agian?'
'At a party?'
'Well yes, or whenever fancy if you wanted to have a practise'
'We shall see'
With that they straightened themselves up and and watched the rest of the film, Charlotte's last comment after the couple were shown in bed having sex. 'Well we can't do that, I don't have the same bits as her'
'Never mind I shall tickle you here ' and he cupped the bra 'And you can tickle me here and the will be great. Do you have to go home tonight?'
'Yes you know I am going to my aunt's tomorrow'
'Shame'
They had only a few weekends to the party and the end of school, Charles was nervous with the approaching date, but excited by the prospect of being able to go to a dance only the upper sixth went too and he was two years younger, it also had this element of having a joke with the stereotypical dating couples who were going, shame they could not tell anyone, it was just their private joke. He sneaked his sisters gown he had worn to the haloween, and had a try on to make sure it still fitted. It did and this time no fake bust, but a real cleavage framed by the cowl neck hanging below. He even shaved everywhere once he had started exams and PE was no longer part of his timetable. The last week he wore knickers everyday but did not have the nerve to wear a bra nad protect his tender nipples.
Revision had taken it's toll on the amount of time both had for each other but they still kept Saturdays for relaxing, and even managed a stop over when Nial's father was away. This opened up a whole new range of oppurtunities now they had crossed the boundaries of intimacy. It had been two weeks since Charlotte had first tasted cum, and with plenty of encouragement had sucked Nial three more times, the last time being the first time she swallowed it all keeping his head in her mouth until he had finished, he said it was how everyone did it so it was how they should do it. Charlotte thought of it as being like coffee, she never liked it but after trying it many times she had grown to like it, the same with spunk. That Saturday though they had had a good time watching or rather the TV was on while they got on with practising being a couple, then later when they were ready for bed Nial was giving Charlotte a kiss while she was in her nightie and he stroked her nipples through the satin, Charlotte was immediately stimulated so he continued doing it, in response she took his dick in her hand and without any trouble shuffled into his bedroom and fell onto the bed, Nial continued to massage the breasts through the fabric while Charlotte gave Nial his second blow of the night. They fell asleep in each others arms exhausted.
It would have been great to carry on the pretence of being a couple living together, but once they had had a cuddle and eaten, it was time to get back to the revising and keeping the parents from thinking they were not taking the exams seriously. They still had one week of occasional exam days, then a week of relative freedom. Nial had got extra hours on his Saturday job and Charles had a long list of jobs that needed doing around the house, but they spent plenty of time together, Nial said it was good preparation for their performance at the dance. Charles got his parents to agree to him stopping over at Nial's for a long weekend while his parents went off for their first holiday alone since goodness knows when, so Charles, but not Charlotte could come and go, and Nial was not complaining about having to look after his young freind.
So the event was set, Charles moves into Nial's on the Thursday evening, his parents leave for the lakes and will not be back till Monday. Mr Riley is working late as usual but is expecting Charlotte to be stopping for the weekend, he is a little surprised to find her there on Friday morning though. Having a few days as Charlotte the chance to dress down a little makes a change, but how do you do that when you have only one of your sister's modest outfits and the rest bought for you by your boyfriend, it was the parent pleasing brown skirt and cream knitted top that got an airing on the Friday. This turned out to be a slow start to a much anticipated weekend, Nial and his father went to work leaving Charlotte on her own, she tidied up, went on the internet, checked her dress for the dance and watched some TV, she even sat out in the sun and read some magazines.
Nial was really excited when he got home from work.
'Have I got a treat for you, or have I got a treat for you?'
'What?'
'I know you look stunning as my girlfriend, but I was chatting with some of the women at work and they wanted to know which salon you were going to, apparently it is all part of the girls school dance experience, I never knew, so I asked where they suggested and you are booked in for tomorrow, I just told them it was a school dance and they said they knew what that would mean and told me to pick you about four in the afternoon.'
'A salon, you must be mad, I will get spotted, what if they do something I don't like or can't change?'
'Sorry, I never thought, just rather hoped you would love the experience, like that time you had your face made up, but this will be even better, besides I left a deposit of £50'
Charlotte realised she had offended Nial and cuddled up to him while she thought about what he had done.
'Ok, if I can have things which are not to bad when I have to be a lad on Monday, then I will be pleased to accept, where is it?'
'Down the street by the shop I work in, I can take you tomorrow'
That evening she gave Nial a treat when she produced a tanning cream and asked him to rub it in all over her newly shaved body, wearing only pants and a bra this proved to much for them and soon they were massaging more than just Charlotte's limbs. That night Nial persauded Charlotte to sleep with him, any worries about Mr Rilley were dispelled when he came in late and went striaght to bed, just the merest of cvility as he said good night and disappeared.
The next morning Charlotte had to decided what to wear to a salon, only got heels and skirts, so the mid thigh kilt, a white blouse and heels, the lowest she had at 3" would have to do. The salon wanted to know what they could do, make up? hair styling? colouring? perm? nails? Charlotte made it clear that she wanted nothing to drastic and went for a wash and styling, some temporary tints, a facial massage and make up. They started with the hair, much talk of what they could do with it if they could really be bold, but he only allowed a little trimming not sure what would happen if she said 'do what you think will look best'. The hair looking like a starburst on her head with fine tendrils coming down over her face and shoulders, she smiled when she saw the finished look recognising her own efforts were way below the professionals. Before the started on her face they suggested false nails that would come off if they were soaked in hot water, Charlotte could handle that accepted the long french tips being glued to his normally well kept nails. While the nails were being done her face was getting facial, cleansing, massaged, oiled. It felt fabulous. Next the make up all done with the burgundy dress in mind, wine and pink eye shades, dark lip liner with a few tones lighter over the lips, off course with flawless foundation and blusher.
Bang on four Nial turned up and was happy to pay the balance when he saw how good his date looked.
'Time to get you home, a taxi is coming at eight'
All the pampering in the salon had got Charlotte into a girlie state of mind and caught his hand so they could walk together. For the first time they saw some people they knew from school, most gave niether of them a nod, but with Charlotte by his side one of the good looking sporty lads who had the pick of the girls, even said 'Hi Nial, see you tonight?'
Nial felt so good when he replied 'I'll be there mate' just for that moment alone Nial felt it had been worth it. Once home Charlotte was all business, stripped off and in satin bra and panties she was feeling very girlie and enjoyed teasing Nial by walking around like this, then she got him to help her into the corset and pull the strings tight. When she started to roll the stockings up he had to leave it was all too much for him. About half seven she asked him to pull the zip up the back of the dress and then inspected him to make sure his shirt was neat, the tie straight and his shoes polished. She filled her little clutch bag with bits she felt a girl should have, then with the gauze wrap around her shoulders she declared herself dressed if not totally ready for the possible disater the evening might be. Nial said it would be a great fun, all the better when they see what a great girlfriend he had brought with him.
It was the girls who approached the couple first, wanting to know who Charlotte was, a friend from away they said, they tried to seperate the couple but Charlotte was going no where alone and Nial wanted to show off his chick. Some lads spoke with Nial and not just the nerdy geeky ones that would speak to him at school, some lads even tried to chat up Charlotte which gave her ego a big boost. They had something to eat, they drank what they were allowed, and as Nial felt acceptance within the group he always wanted to in he told Charlotte to go and dance with some girls so he could spend time with his new mates, not that he said that clearly, but it was how he felt. Charlotte did her best to play the girlfriend, holding his hand, sitting beside him, giving him a kiss, all that practise had paid off she hardly ever had to think what it was she should be doing. As the dance drew to it's end Nial's dream came true when Rob invited them back to his house for a party. Rob had one of the biggest houses around and always had the latest whatever, this to Nial was brilliant. The taxi he had booked to take them home, took them to Rob's instead where there was no restrictions on alcohol or behaviour it seemed. Charlotte had heard some of the girls talking about whether they would 'perform' for their boyfriends, one was sure she was going to make sure hers had a good time, saying he was too hot to throw away. Charlotte just wondered where they would do it if they did it at all, surely not in full view, maybe in a bedroom, hopefully unseen. A glass of wine and a beer they mingle with the others, some nice motwon comes on that Nial does not like but Charlotte cuddles up and gets him moving. His tie and jacket are off and she undoes a couple of his buttons and pulls the shirt out of the trouseers to make look better. It is not long before they notice the couples are settling down and snogging one another quite openly, so they follow their lead. Then as Nial gets up for another beer, Charlotte wonders where the couple who had been near them had gone, in the wait for the toilet she sees the girl touching up her lips and thinks to herself 'She said she might do hers that night' well maybe she had. She meets Nial who has come to the same conclusion and they are in the mood for some fun as well. Not really sure where to go they find a bedroom unoccupied and sneak in, Charlotte makes Nial undo the dress, it must not get spoilt or the game would be up at home, so ten minutes after going into the room the door is opened by another couple who say 'sorry mate' but not before they had seen Charlotte in her underwear and heels croutched over Nial with his penis in her mouth. Charlotte stops and says that is it she has lost the mood, Nial thinks 'excellent, seen been given a blow by this hot chick. Respect'. It does not take much for Charlotte to relax and Nial to stroke her tits before he has persauded her to finish of what she had started. Then once dressed and some wine drunk to rinse the cum away they rejoin the party. About four they are both tired and Charlotte wants to go back, so Nial calls a taxi, they make their thank yous and leave, lots of girlie hugs for Charlotte and hand shakes for Nial, he felt he had made it.
Charlotte needed help undressing and Nial takes the oppurtunity to kiss her in some new places, this revives her and allows him to kiss her nipples, with the wine and an exciting evening they end up on the bed, but instead of his dick being wanked, it ends up between her legs and rubbing against her arse. Somewhere in Charlotte's mind though possibly not in Charles's is an image of a girl on her back, legs up and the boy pushing his manhood into her hole, so when they end up in this position and Nial is above her he asks if she is up for being his girl completely, her reply is just do it, it is what you want, so get on with it. He does not need asking twice and pushes his dick into her tight hole and after a few thrusts comes and collapses on her.
Eventually they both wake later that morning, groggy and hung over but able to recall everything that had happened the day before.
'So what happens now?' Charlotte asks
Just then Nial's phone rings, it is Rob, there is a wrap that Kate thinks is Charlotte's at his house, then he invites the couple over for an afternoon game of pool. Nial believes he has made it and accepts the invite, urging Charlotte to stay for another day. He does not have to urge too much and Charlotte cleans herself up and gets ready to go round to Rob's. This time they have Mr Rileys car and arrive in some style.
They are not the only ones there, Charlotte is grateful the wrap was found, how could a missing wrap be easily explained away. The boys go to play pool, the girls go to chat and discuss the previous nights activities, who got who, who didn't get anything and so on. The question was eventually asked 'Why Nial?' Charlotte replied that he was really nice if you got to know him, but he is such a wierdo, no he likes odd music, he does gaming, he has poor coordination, but he is bright and nice. She thought of saying and he is a stud in bed but refrianed, that might just be going too far on the exageration of her friends qualities. The party got interesting when some girls started playing pool, Charlotte leant over the table and gave everyone behind her no reason for thinking she was not wearing stockings, Nial stepped in quickly and covered her modesty but it had been seen and that was enough. Some other girls did sexy posing, but it was when they went to get drinks that the conversation turned to sex, they all knew she had been caught sucking Nial and wanted to know what he was like, she owned up to him being her first, what she had not reckoned on was that these girls were pretty loose with their morals and suggested she try another Dee stepped in and offered her boy, Charlotte was caught and did not know what to do, this had gone way past pretending to be a girlfriend. Then to stop any further time for thinking Dee went and got her boy, she came back leading him by the hand, 'Charlotte wants to know why I think you taste the best' the boy looks round a little perplexed at having half a dozen girls watching him. So Dee moves things along by kissing him and undoing his pants at the same time, a few careful massages and he is too attention but feeling awkward 'Come on Charlotte he wont bite, and if he does I will want to know why he has not butten me before' Charlotte looked around and the girls are looking back urging her on, she could run out but then Nial's dream would be over, she could say no, but these girls would not understand, so while Dee kissed her boy's mouth, Charlotte kissed his dick, it did not take long before he had cum in her mouth. Dee spoke first 'Was that good' her boy said yes but quickly added, but not as good as her. Charlotte just said it tasted different, then she 'Nial come look at this' one of the lads had come to find his missing friend and saw Charlotte on her knees infront of the boy. Charlotte was up like a shot and blushing, then the girls started asking Nial to come in, word had it he was quite the stud if reports of the night before were true, like Charlotte before he saw it as some sort of test so when Dee kissed him and cupped his balls he accepted this could be fun. The girls all wanted a taste but when it came to finishing him off they pushed Charlotte forward who wanted to be somewhere else as she swallowed his dick and then his cum. All the girls then hugged her and kissed her, it was odd but she felt accepted as a girl. Nial was taken back to the games room and given a beer which he knew meant he should not drive for an hour after finishing, his father's drink drive rule, one per drink, right or wrong that was Nial's limit. Charlotte had no such limit and was drinking spirits and mixers not tasting the rum or vodka in them, so when they left a few hours later she was quite relaxed and a little slurry in her speech.
On the short drive back, she was teasing Nial and asking if he had got everything he wanted from his 'hot chick'. Then once inside and drinking coffee he tried to have a sensible conversation, basically, was this going to be the end of Charlotte? She was cuddled up next to him and shocked him with he reply, 'Well it should be, but I have one last thing I want to try before going back to being a dull boring geek called Charles' Nial asked what sensing his friend had enjoyed the time as Charlotte more than he suspected, 'The girls said the first time they had sex it hurt, and they gave me these' she pulled a few sachets from her bag 'the condom we can do without, we were both virgins and I am never going to get pregnant' Nial was wondering where this was going 'this however they say helps smooth the flow.' She started to undo his pants and fish his reawakening penis from inside. 'The one thing I would like to try is sex and see if you can get me there. You up for that?' Nial slipped a hand inside her blouse and played with her nipples. Soon they were on the living room floor, his pants off, some gel massaged onto his pole, her legs up, short skirt around her waist and knickers off. This time it was not hurting as much, gel and alcohol helping there, and she was beginning to feel something building inside like she might explode. She could remember having a wank and the sudden relief it gave but this was different, a slow build then an intense desire to get Nial to push in as far as possible accompanied by a body wracking spasm. Then after many aftershocks relaxation like she had never know. Nial lay on top of his girl himself spent but wondering what had just happened.
Later that night as they were cuddled up in bed Charlotte quietly told Nial and hopefully herself that come the morning Charlotte was over, Charles was back. That was an end to it, full stop.
It took Charlotte nearly all day to transform her hair into his, the nails, the make up, the attitude, everything had to be changed hopefully leaving no signs of the weekend or past months. Charles was home for his parents getting home and after a few pleasantries about how their weekends had been, his mother looked at him oddly and asked if he had done anything to his hair as it looked a different shade. Charles had a back up story for just in case and told her that he had been to a party and some girls had teased him into letting them play with his hair, his mother knowing Charles would do almost anything to be accepted told him to be careful about letting people take avantage of him, he said he was cool with it, and the subject was dropped though he did have a sick feeling in his stomach that she knew more than she was letting on, had he been found out?
He had all his sisters stuff back in her room, and it seemed life was reverting to normal, when Nial was not working Charles would call round and play games or watch sport, Nial occasionally visiting as well. But Nial was feeling his self esteem drifting, within a week he had been invited round to one of friends houses for 'party' but he had to go wothout Charlotte which made him feel a little out of it, by the end of the second week he had been round to his new friends again and had seen them about town, but for him all he was aware of was the comments that Charlotte was missing, what a great girl she was, when is she back? his lack of self confidence meant he needed Charlotte to feel accepted, a part of the group.
After two weeks Nial was getting quite down about the situation and felt he needed Charlotte back if only for a day, so on afternoon while they were on the computer he prepared a drink adding a double dose of hormone tablets to it, then waited a while for them to hopefully work in some helpful manner. It might have been the tablets, it might have been coincidence but by accident nail brushed against Charles's chest which made him jump.
'Still sensitive?'
'Yes'
''Any bigger?'
'A little I think'
'Can I take a look?'
Charles lifted his T shirt to show his friend.
'May be' then without asking Nial cupped one in his hand, Charles took a deep breath and made a low owww sound, so he squeezed the nipple and got more reaction.
With a sudden change of subject but no change of position, Nial asked 'Rob has asked if I fancy going to the pub tonight, do you want to come?' he massaged the small breast some more, Charles was fighting the feelings that his breasts were making but with his back against the chair he could not move away easily. 'Go on, you will enjoy it I'm sure' after a pause 'all your stuff is still in the case you put it in when you sorted out after the dance' still with Charles in his grip 'I'll ring your parents and ask if it is ok for you to stop the night'
'Ok ok I'll do it' the memories of pleasure were just to much for some one as weak as Charles to withstand.
An hour later Charlotte is back, wearing the enhancer bra, a pink vest top, short mini kilt and heels, hair and make done in a very girlish style.
'Lovely to have you back Charlotte' said Nial as he kissed his girlfriend.
'Not so sure this is a good idea' Charles was still there sounding a word of caution.
Nial did not want his friend to loose confidence and run away so he decided to give her a good kiss and excite those nipples again. Charlotte capitulated as Charles's reserve crumbled. It did not take long for the old roles to return with Charlotte preparing some food for them both.
Being only sixteen and looking nothing like the student ID card they used to prove their age Charlotte was limited to soft drinks while Nial could have beer. Nial was full of himself now his girl was back and to Charlotte's surprise the girls welcomed her into their little group once more wanting to know where she had been, so the lies increased to cover up the truth. It was a long walk back in heels but one she enjoyed as the pleasure of being someone popular stayed with her. Once back the amoroous Nial got even more randy, hardly able to wait for her to get ready for bed, but once she was beside him he made sure she was reminded of the last time they made love, enjoying her climax as much as his own because it would help reinforce the good memories of being Charlotte he hoped.
In the morning Charles reappeared and went home after trying to make it clear that Charlotte would not be coming out again and he should get rid of the clothes as they were only a temptation. Clearly Nial had no intention of doing such a thing and just stored them away. Later in the week they met up for some chill time, as they called it, and Nial talked about the trip to the pub and how Charlotte seemed to enjoy it, Charles was trying to say no, that he was a boy and they should leave it behind them, but all Nial needed to do was stroke a breast and Charles felt the shiver run through him, and Nial asked what boy gives that reaction. Charles was getting more confused, since the weekend he would swear his breasts had got more sensitive with larger and darker nipples and when he tried to relieve himself he could not unless he imagined himself with Nial looking pretty and pushing a finger inside his hole, he ejaculated but from a limp penis which was rather emasculating for him. They came to an agreement that Charles would be Charlotte provided it was somewhere Charlote would like to go and Nial would supplement Charles's meagre income. And so Nial got his girl back. As if to test this agreement out Nial set up a night out with Pete and Dee the following evening. Dee is a bubbly character who had got Charlotte to suck her boyfriend, which had meant she was accepted in some way. Besides Dee and Pete were always good fun to be around so Charlotte was out once more after swearing never to wear a skirt again. Dee was just as provocative as ever, Pete was all over her but there were times when she would flirt with Nial, and when she kissed Charlotte told the boys they could kiss if they each other if they wanted. They parted quite late and everyone knew Pete was going to be performing as soon as the door shut, there was no such luck for Nial who had to walk Charlotte back to his house, let her change then walk Charles back to his home, no chance for anything else. This made him consider that sleep overs were the best way for him to enjoy Charlotte to the full. This happened the next Saturday, Charles parents were out that night so had no compliants about Charles stay with Nial, and Nial certainly had no complaints. Charlotte appearred at lunch time so she could be taken shopping for new clothes or whatever took her fancy, followed by her cooking for them both which lead onto going round to Rob's once more where Nial did the boy bonding in the games room and the girls gossiped and compared nail colours in the sun lounge next door. The evening drifted into lower morals when Dee and Chrissy started to tease Chrissy's boy Jake. They had his pants round his ankles so he could not run away then while Chrissy kissed his mouth, Dee kissed his dick. Soon it was like a floor show with the other egging them on until Jake could take it no more and came, Dee quickly catching the cream in a glass then offering it round. Dee was soon urging others to entertain them, Charlotte found herself being kissed by every lad and somehow managing to stop them feeling her secret by distracting them with more overt feeling of the boy's groin. A surprise for Charlotte was to see Nial being very intimate with a girl they had not meet before that night and feeling pangs of jealousy, he was her boyfriend after all. The evening ended as expected with Charlotte cuddled up with Nial after having another session of sex which was becoming ever more attractive an activity now they were geting to how to do it better.
Through July Charlotte was out most Saturdays, but early August after a particularly amoral night at Rob's where they had played silly childish party games like forfiets, pass the parcel and musical chairs. Musical chairs had the lads as chairs and when a girl sat on one they had snog until the music started again, forfiets were little notes in a bran tub daring the finder to do things with some one else, for pass the parcel the girls wrapped their knickers in many layers of paper and as a boy came across a pair the owner had to step forward to claim them offering something in return for her clothing. This lead to alot of genital kissing in both directions, for Charlotte it meant only one thing giving Pete a blow job as only Nial could know she only had one hole.
Whether it was the excesses of the night before or just getting too casual about the whole Charlotte thing but that Sunday Charles was taking a shower and forgot to lock the door, so when his walked in she saw pretty much how well shaved her son was, and then when he was helping clean up in the kitchen she caught his hand and commented on the remains of red polish on his nails and asked if the girls had been teasing him into doing things again. Charles was sick to the stomach and swore never to dress again. Nial was understandably not so keen and pointed out they had an agreement, plus having a secret is something of a buzz especially when you are not sure what sort of reaction Charles's parents would give if they ever found out. So after a lull in Charlotte's presence she persauded back out. Then the week before the exam results were published Charles parents decided to take a weeks holiday and as Charles was spending so much time round at Nial's wanted to know if he would rather stop there than go with them. Nial said yes for him, Charles knew what this would mean and as soon as they were alone made it as clear as he could this would be Charlotte's last time out because school would be cack soon after and Nial would no doubt be off to university within weeks of getting his results.
Nial had a week of waiting and anticipation of having his girlfriend living and sleeping with him for a whole week, and if it was to be the last he wanted it to be the best. Charles was dropped off on the Friday evening along with a case full of clothes so his parents could make an early start in the morning. Once they were gone Nial picked up the case and locked it in the shed, then while Charles was having a shower pinched all his other clothes just to make sure there was no trace of the boy left. Charlotte came out of the shower knowing what to expect and dressed accordingly, so when Nial's father came home Nial and his girlfriend were watching TV with a drink and a smile on their faces.
The next morning Nial informed, did not ask, Charlotte that a reservation had been made at the salon and she was to be there for ten, he had paid for it all and she should just relax and enjoy the experience. She tried to relax but having your hair trimmed into what was possibly a bit more feminine a cut than you really wanted and having it coloured a darker chestnut was maybe a little worrying, but the nails were possibly of more concern, the hair could be shaved off if required but the nails were not stick on, they were long acrylic bonded extensions that the girl assured her would take some removing without coming back to have them filed away. Charlotte left feeling quite vulnerable, the week would be fine but what would happen at the end of the week? Nial loved the new look and took her to get a new sundress, soft floaty and long. Charlotte was now a girl until Charles got his clothes back, had a boy cut and shortened the nails, no way could she pass as a him without some drastic changes.
That evening they meet up with their friends at Dee's house and enjoyed plenty of intimate cuddling and drinking until they drifted off home. Much to Nial's surprise Charlotte had been invited out by the girls for a girlie night the day after which meant he was on his own while she went off alone for the first time. Charlotte discovered these girls had no limits or barriers to what they will talk about, clothes, make up, school, boys, sex and in quite explicit detail. She found out Pete likes to be underneath when making love which suits Dee, Fay likes come, Chrissy is bi and Jen has had it anally, which really got the other girls talking especially when Charlotte admitted she had as well, but was careful not to give the reason why. The talk did mean that when she got back to Nial's she was randy wanted to try being on top but Nial was not keen, it was his place to be in charge and to him that meant on top, Charlotte did not mind as long as she felt that explosion inside as he slid his dick inside her.
The week for Charlotte was pretty similiar to the weeks as Charles before, through the day the house would be empty so after a bit of housework and shopping for food there was tV to watch before getting a meal ready, the main difference was that Charlotte could enjoy the freedom of soft fabrics and bare skin which Charles had kept covered just in case anyone asked why his skin was hair free. The other difference was that she got a cuddle when Nial came home, a cuddle while they watched the TV and an orgasm when they went to bed.
They went out with friends some evenings but they were happy in one anothers company. On the Friday Charlotte was getting worried about how she was going to ever look like Charles again, they had the house to themselves and in an attempt to lighten her mood Nial started to arouse her, being the person she was, basically weak and enjoying the sex it was not long before before Charlotte is lying on the living room floor, legs apart, mini skirt up round her waist and blouse open, with Nial on top letting her enjoy his attentions to her hole.
Then the door bell rang.
Charles parents had not had such a good week, the weather had been poor, the hotel food rubbish, they had not spent so much time together for years and bickered all the time, so had decided to come home early, and to make things worse they had dropped the phone in water and could not call anyone. They had gone home and seen that no one was home so drove round to Nial's to pick Charles up. As they rang the bell Charles's mother looked in the front window,
'Derek, I told you that Nial was too old for our lad, he's in there bonking some girl, can only hope he is not somewhere with some other girl, you know what they are like these days'
'If I remember right, you said it would be good for him to make friends with older lads, maturing you called it, besides he is sixteen, when did you have your first?'
'The couple on hearing the bell stopped and panicked.
'My god Derek, that birth mark did you see it? Charles has one just like it'
Nial made it to the door not sure who was there and got a real shock when he saw Charles's parents.
'we've come to pick Charles up'
Nial thought quickly 'He said he was going round to your house'
'Not there, where is he?'
'Out somewhere'
'I don't know what you are up to Nial Riley, my son missing while you and some tart are doing things on the floor, we trusted you.' then she stalked off 'come Derek'
'He wont have gone far, I'll fetch him back when he shows up'
The door closed and Charlotte is in terror believing she has been found out. She dashed to the shower and was rinsing everything off, trying to get the hair to change colour and nails to come off, and a face scrubbed so hard it smarted, all the while Nial telling the emerging Charles to calm down, how could they know who was on the floor with him, at worst Nial is just randy lad, the girl they don't know.
An hour later Nial is driving a now sober and very clean Charles back to his home.
In and effort to suppress his distress Charles goes over the top asking how the weekend was and not letting them get a word in, but his mum is studying him very carefully, his hair looks quite different, very much the same colour as the girls, his finger nails when he takes them out of his pockets seem to be long, and his lips and eyes look very red like they have been scrubbed. Eventually he slowed.
'You look different, where did you get your hair cut?' his mother asked
'A place in town a friend recommended'
'Not a barbers then?'
'No'
'A woman's salon?'
'Unisex' Charles mumbled
'Can I see your hands please?'
Reluctantly Charles pulls his manicured fingers out of his pockets knowing the game is up.
Charles was the weakest and the constant pressure was making him break, tears came first.
'You still have that birth mark on the top of your leg don't you?'
That was it, Nial had commented about the mark just above the stocking tops on more than one occasion. Charles fled into his room crying. He was allowed to go but Nial was not so lucky.
'This way young man and explain yourself'
He had several minutes to think up a story that he hoped might save some face. He started by telling them that he considered Charles to be transgendered, a girl in a boys body. That he had been a refuge for him since christmas, somewhere to go and see if he was a girl or not. Then asked them what they thought the person on the floor was, a boy or a girl? he got out his phone and showed them pictures of Charlotte dressed and out, then he decided to play what he thought might be a trump card, he told them about the breasts, not how they got there, just that they had developed, surely this was part of him being a girl. Charles's mother wanted to know why he could not talk to her, her husband answered that by pointing out how she was reacting at that moment. Then she said it was all her fault, picked up the picture of him at the family party and said 'I made him wear that dress, I made him want to do this' and started crying herself.
Charles's father motioned to Nial that he should leave, he would sort things out from here. He made his wife a stiff drink then went to see his son telling him that he thinks they know pretty much everything, the cat is out of the bag, we now have to deal with it, but he was not a person who knew how to touch people and awkwardly placed a hand on his son all the while feeling he should be giving the lad a hug, but that was not what men do, a pat on the shoulder would have to do. And left him thinking about what Nial could possibly have said to them.
Charles was not sodding any more, but he was terrified as to what lay outside the bedroom door, a mother who must hate him and father who will not understand. Charles considered many things he could do. running away, going to Nial's, telling them it was big joke and he would never do it again, sneak into his sister's room change and then confront them. What he did not expect was for his mother to come into his room and pick him off the bed so she could hold him close.
'Nial told us everything'
'Oh no, you must hate me'
'He says you want to be a girl'
'Did he?'
'He says you are growing breasts'
'That is true'
'how can that be'
'I have no idea'
'Can I see?'
On an awkward moment Charles lifts his T shirt up and lets his mother see his dark nipples and the mounds beneath them.
'An A cup maybe a B I guess, and you have no idea why'
Charles had worked out long ago that Nial must have been feeding hormones to him but was not sure if he wanted to stop the wonderful sensation he got when the nipples were played with. 'Probably hormone tablets'
His mother stiffened suddenly, Charles was expecting another tirade. 'Where from?'
'Does it matter?'
'Do you want to be a girl?'
'I like pretending to be a girl, it is more fun than being a boy'
'Oh' she paused as her husband brought in some drinks 'Why?'
Charles took a deep breath and held his cup in his hands. How much to tell them, he could still deny it, were thoughts that ran through his head.
His mother asked why again.
'Do you not like wearing soft clothes? the taking time to make yourself look good? feeling attractive?'
'With your father not noticing if I wear a bin bag or a couture gown, no I don't'
Father butted in 'I do notice, you just tell me to stop because I must be after something'
'No I don't you are just a man'
Charles put his head down, they were at it again.
'Sorry son, we bicker too much don't we'
'Yes' Charles answered
'Maybe we should all sleep on this and talk some more in the morning, We don't go to work till Tuesday so maybe we can sort things out by then'
And that seemed to be it. Charles was left alone not sure what had happened but happy they were gone. He texted Nial and asked how he was. He was fine but was concerned how Charles was. Nial told him roughly what he had felt forced to tell his parents, how upset she had been, and asked what he should he do with all the clothes.
The answer to the last question came in the morning, his father came into his room with some toast and a smile on his face, Charles now knew what those noises had been in the night coming from the next room, parents making love.
'Right Charles, I am going to run you over to the Rileys so you can collect all your things, and you can say no to this, when you get back you can dress up as a girl and we will see what you look like. Ok?'
Charles did not say a word, this was a shock, maybe they were going to trick him somehow. Half an hour later they are outside Nial's. Inside Nial's, with his father outside in the car, a quick conversation about the unexpected request was discussed.
'Maybe they really want to know Charlotte'
'Maybe they just want to humiliate me'
'Maybe they want to see if you look like a girl'
'Maybe they just want me to say I am mad and have me locked up'
With everything in bags including the things Nial had bought, Nial looked at his friend, gave him a hug, 'Not sure lads do this, but you are a mate in trouble, if you want me to come I will, if not you know I will be here. That goes for Charles or Charlotte OK'
'Thanks' was all Charles could manage as he walked out with the bags.
Back home his mother was up and looking different, gone were the usual trousers and flats, she was in a dress and modest heels.
'Do you want any help?' she asked
'I will be fine' he replied
'You look good this morning dear' his father said to his wife and gave her a kiss.
Charles sent a text 'Mum in a dress, dad being nice, not sure what is going on'
The reply 'Here for you, will you do it?'
'Don't know'
Charles went to his room and sat on the bed worrying. After about half an hour he had been sitting on the edge of his bed trying to work out if this was just a horrible dream and it would stop, there were just so many things that could go wrong. With all this going on in his head his mother put her head round the door,
'Come on dear, I will give you an hand?' Charles just looked up 'Well go and have a shower for a start and wash your hair'
With a straight command he did as he was told and went for a shower, while he was in the shower she removed his clothes and left her silk robe out where he would see it. He came out of the bathroom in the robe and a towel wrapped around his head.
'Let me dry your hair dear'
He had always been fairly weak willed and she had always known he would do anything if you said it in the right manner, this new situation was apparently no different. She brushed his hair and dried it with her drier getting the volume and style back so the hair looked most definitely femal once more.
'You do have lovely hair you know'
'The lady at the salon said so'
'A salon?'
'Yes when we went to the leavers dance at school, Nial paid for it'
'Oh I see'
'It was what all the girls did'
'And you were one of the girls'
'Yes'
And so Charles had the details drawn out him, the salon, the practising, the dance, but not all the more intimate details of the party or the practising being a girlfriend.
'Do you want to do your make up first or get dressed?'
'I have my own make up' he offered
'Oh I suppose you will'
He went and picked up his make up bag from his room and returned to his mother's vanity table. Then went through his routine of moisturiser and cleanser before putting on light foundation, mascara, liner, blush and pink lip stick. And because the nail extensions were still there, they were repolished in a soft pink colour.
'I can see how no one picked you up for a boy, you look so much better than when I made you dress up for that party'
'I used Sarah's clothes mostly, so do you mind if I go and pick something now?'
'No I want to see the finished you'
They went in to his sister's room and opened the drawers and wardrobe. he found a padded bra and matching knickers, then picked out a longer grey skirt and pink sleevless blouse and as there was never any thing else, high heels. Then because he felt embarrassed to be seen naked in front of his mother he asked her to leave while he dressed. Minutes later he walks into the kitchen.
'Well I think I can see what Nial saw in you, very pretty'
'Derek stop it, this is Charles'
'No mum, it feels better if you call me Charlotte' he said this looking at the floor and feeling very awkward before his parents.
'Right well who wants a coffee, it must be that time by now' his father tried to inject some normality.
'Yes thanks dear, Charlotte do you want a drink?'
'A coffee please'
'Right then Charlotte, what are we going to do with you?'
'You are clearly very good at this, and from what we saw yesterday, well let's just say, you prefer boys'
'It was only playing about, we had not done anything like that before, we were only role playing'
'I think not, he had his you know what right inside I guess and you were not fighting him off, I know what I saw and that young lady was not playing about'
Charlotte was blushing at the thought of her watching them on the floor.
'You called me young lady' she was recovering
'I did didn't I'
'well young lady I am not sure I approve of your behaviour'
Charlotte was silent and sipped her coffee.
'Right Derek, we are still on holiday which means I am not cooking so where are you taking us for lunch? and bear in mind I am not going in any old cafe dressed like this'
Charlotte had to walk out of her own front door for the first time, but if she was worried her mother commented
'Don't worry darling, the neighbours will think you are Sarah, come on we can't wait all day'
They drove into town and found a nice wine bar with trendy office types in, the menu was not cheap, but the clientelle suited Charlotte's mothers idea of where you went when dressed up as she was. A pleasant meal followed by a wander round some shops, then on the way home a trip to the supermarket for the groceries, Charlotte being very much included in all these activities. Then once they were home and tidied up.
'So Derek what do you think?'
'No one was taking a second look except for some lads outside Tescos'
'What did you think Charlotte?'
Trying to deflect the real question 'Well you did not bicker all day like normal, and that coat you tried on did look great'
'You know that was not what I meant, being a girl is what I meant, did your feet hurt, was you fed up having to touch up your lip stick, is this what you want all the time?'
There was a pause while Charlotte considered the answer 'I have had a lovely day, I quite like the thing of having to do my lips and walking in heels is kind off....well makes me feel good........as for being a girl all the time I don't know, I have been a boy for 15 years and a part time girl for a few months,' her voice tailed off as if in thought.
'Well it needs sorting out, we need to know what is happening, you know I like to have things sorted'
'Yes mum I know, what do you suggest?'
'Well I want you to see someone who understands these things, get a professional opinion, and go with what they recommend'
'You sure, I could always try to be Charles for you'
His dad spoke up 'No the cat is definitely out now, I could tell you were behaving too much like a girl for this to be something you can just drop like that, no your mum is right, I shall make some calls tomorrow'
The rest of the day passed off uneventfully, Nial was texted to tell him everything seemed fine. His parents went to bed early and did not go straight to sleep, so Charlotte had to listen to their bedroom entertainment through the walls. She got herself cleaned up and went to bed, but it was cotton pjyamas that night, no satin nightie to keep the mood going.
Tuesday was a normal working day for the parents, but a list of jobs was left on the table, oddly the Charles that usually headed such notes was missing. Charles did not know what to wear that morning, should he wear a skirt or trousers, he in theory could do either, but he was still wary of his mother so settled for underwear under his nicest boy clothes and heels that could be removed quickly, his hair with some gel to style it and that would have to do. Nial came round to find out what had happened. He seemed to think they had got away with it, his girlfriend might still be around, but he too was mortified at the thought of being watched as they were on the floor, but did ask if Charlotte had been enjoying it until they were interrupted. The smile at the memory told him all he needed to know. Then he commented that the boy clothes with long pink nails looks odd, why not just wear what looks right with your body. So he went a borrowed a pair of jeans from his sister's room and a plain blouse.
When his mother came home she commented on how plain he was looking.
'I was unsure what you would think if I dressed as a girl today'
'I suppose I should say something, you should follow what feels right, but it is nice to know you think of how I might feel'
'There is one thing I would like to ask you'
'Yes'
'Can I wear a bra all the time, my nipples are so sensitive and a bra protects them'
'I suppose you should, it could look odd if you wear any tight fitting boy tops though, be careful wont you'
'I will' then looked at the long nails and thought 'a bit too much too look odd now'
His father came home saying they had to be at the doctors for seven to get advice. At a little after seven they are in the GPs surgery and being asked questions, then the parents are asked to leave so an examination can take place. After some more questions and blood samples taken, the doctor asked to see his breasts before calling the parents back in.
'It seems your child for one reason or another is not developing as a boy any more, his voice has not broken, there is little hair growth, he says his penis does not get erect, but most significant is the body shape, this could be down to the hormones he has taken, but I suspect that is only part of the story. Now we do need counselling, but Charles will need to decide which way he wants to go, if he wants to be a boy then there are drugs that will substitute the male ones he lacks, but I think lack of erections is a bad sign, alternatively we can encourage the female growth with different drugs and make you look like a girl, though clearly you will never be a fully functioning female.' He let this information sink in 'It is a hard decision, but one you should not take too long over, the longer you leave the more the body will develop and there is no knowing what might happen, imagine your voice breaking and your chest getting bigger, that would be confusing'. No one spoke so he continued 'Call tomorrow, I will let you know how I have got on with counselling, and I can also arrange to leave a pescription at the desk for whatever you decide' They all were in a state off shock for different reasons, but none of them was sure which course to take, and just leaving things seemed not the easy option.
Charles rang Nial, his mother rang her sister, his dad read the paper. Nial siad it was Charles's decision but Charles knew that Nial would love to have Charlotte full time, and after what seemed like an eternity since the weekend, Charles would love to be Charlotte and cuddle up to Nial and feel his warmth. Charles mother was wanting someone to talk too and just get it out, so her sister would do. His father could not articulate his feelings so hid, but he was as confused as the others, a son or a daughter? not a chioce he ever thought you could make.
It was late when mother came off the phone.
'Right here is what is going to happen, I am not sure I am coping very well with this, so Jane has come up with a temporary solution. You can go and stop with her for a couple of weeks, which gives us till the end of August, but if you go there you will have to be Charlotte all the time ok. The alternative is you stop here and try being Charles all the time. Now for what it is worth I know my sister is far more fashion conscious than me so if you want to be a girl I can think of no harder person to follow. I also think the best way for you to find out if this is what you really want is to throw you in the deep end, you can come home anytime you want but we go back to how we were and let the doctor work out what is up with your development.' she looked around for any reactions 'Right then Derek, you ring up in the morning and get the pescription for the female hormones, and you Charlotte will get yourself packed and get yourself to the doctors and pharmacists, any one got a better answer?'
So that was that, next morning before work father had rung the surgery, by twelve Charlotte had dressed and collected the scrip and picked up the pills. Then sat at home with a glass of water in one hand and a pill in the other, this was a momentus point in his/her life. Unexpectedly Nial rang, he soon found out what was happening so ran round to see her. She was still there glass and pill now on the table.
'Here' he gave her the pill, and now drink this, he passed her the glass. 'Just think back to the times we had, it is worth it, believe me you are wasted as a boy' Charlotte swallowed as she was told to. 'Now hows about a kiss.' This was the best thing he could do as she felt him hold her and feel like his girl again. The bad part was having to move out to aunt Jane's which though not on the other side of the country was on the other side of town about 20 miles away, no friends, no Nial, just aunt Jane.
Aunt Jane was the oppposite to her mother, always classy in her dress, she was good at looking good if you know what I mean. Where mother was effiecient and ran a smooth accounting office, with her clothes reflecting that, trouser suits, flat shoes and plain blouses for practicality, aunt Jane wore heels like his sister, had hair that must take an age to do in the morning and a figure she flattered with good clothes.
Charlotte had collected all her clothes from Nial's and been allowed to take a few from his sister's room, then he was driven over by his father in a silent car, niether knowing what to say. He did not stay long, Jane rather intimidated him and was glad to be away on his drive home, leaving his child in his sister in laws hands.
'So Charlotte you think being a girl is better than being a boy, you could be right, but part of you being here is to make sure this is not just a passing whim.' Charlotte sat feeling nervous 'Right as part of this deal I expect you to do everything about the house, the cleaning, the cooking, the laundry, the shopping, I shall leave you housekeeping and I do not expect to have to do a thing and you keep the place spotless.' pause 'right?'
'Yes aunt Jane'
'Also, because this is supposed to make life hard for you I will expect you not only to be dressed as a girl all the time, but as a fully made up, hair done up, high heeled and possibly corseted girl, that depends. Have you ever worn a corset?'
'Yes aunt'
'So you know the benefits and drawbacks, good' she looked Charlotte up and down 'You are pretty you know'
'Thank you'
'Any questions?'
'Can't think of any'
'You don't say much do you. I have been having some wicked thoughts. Now if you stand over there' ...... 'Yes just there, now bob up and down, just bend the knees a little, and pick up the hem of your skirt as you go down'...........'Yes just like that' Jane smiled 'Now I am sure you and your friend must have been looking on websites about people like you, how did you feel about those men who were maids? I could quite like having a maid for a couple of weeks, you could call me madam, I could ring a little bell when I needed you, and you have the curtsey off to a tee already. What do you think?'
'Not sure aunt Jane'
'Not sure? as in not sure you want to do all the housework, because you will be, or not sure as in wearing a plain uniform and having to bob up and down every time I call you'
'Not sure about the uniform'
'So bobbing up and down is fine'
Charlotte was not used to this sort of direct teasing.
'Oh Charlotte dear I am just teasing you now, everything else is well.....optional.......just if you did I could quite enjoy being the lady with her servant'
Charlotte did not reply
'Well Charlotte do you drink wine?'
'A little'
'Good, ther is a bottle in the fridge, bring it through and we shall have a glass'
Jane went on to explain in more detail what Charlotte would be doing, which shops were good, where and how the machines worked. Then showed her to her room and said good night.
Next morning Jane was gone early, so Charlotte dressed and looked around to work out what needed doing. She had decided to take up the challenge that her aunt seemed to imply that being with her was not going to be easy, so she wore the corset and tried to give her hair more body when drying it, and had worn her highest heels all day just to say she could. When Jane came home there was spaghetti waiting and a clean house. She was impressed and told Charlotte so.
'It seems you are going to do this with some gusto, and as a reward for todays efforts I am going to treat you tomorrow. I think you need a bit of a style change, so you can have my slot at the salon tomorrow as long as you let me choose what style you have'
Jane was a good looking woman in her late thirties, what Nial would call hot, so Charlotte agreed completely trusting in her aunts judgement.
It was just before lunch when Charlotte emerged into daylight the next day, and rather shell shocked from the experience, first her hair had been coloured, permed and styled so it was now a bobbed semi wave blonde. And as if this was not enough when Jane picked her up she took her to a jewellers that pierced her ears, Jane just stating that all girls have pierced ears, there was no discussion.
It was later as they ate the meal Charlotte had cooked when Jane asked if she liked her new look, Charlotte said it would take some getting used too, Jane told her she had to get the volume into the curls everyday to make it look its best. Charlotte asked why had she chosen this rather striking style. Her answer rather took her aback.
'You walk around in high heels, short skirts, and showing your cleavage, bit of a bimbo I reckon or else you have a boyfriend that likes you sexy, either way blonde suits'
Jane's guess that there was a boyfriend was proved correct when Charlotte asked if it was ok for Nial to come over on the Sunday. To find out more about her niece/nephew she agreed. Nial turned up in the afternoon and was surprised at how much Charlotte had changed, the new hair being a big hit. They did not get much private time together so only managed a few quick kisses, but agreed to see each other whenever they could. Jane's reaction to Nial was to see Charlotte as more of a girl than she first suspected. The following week she assessed her in many ways but the one thing she did not like was the teenage look. She put it to Charlotte she had dressed to please Nial, and she had dressed to please her mother, now she could dress to please her and on the saturday took her round some of the discount stores to give her an idea of what might get her approval. They got home with several bags all containing clothes. Tops with bows at the neck or the waist, chiffon balloon sleeves and pretty little cap sleeves. A variety of skirts, a long striaght one, a soft floaty cotton one, and a flared one with stiff underskirts, there was also a pair of white trousers. Charlotte knew what to do and changed immediately into the pink balloon sleeve blouse and black flared skirt, with off course red heels. Jane said she was so smart they would eat out and went to a local resturant that made them both welcome.
On the Thursday of that week Charloote's mother rang to say the exam results had come in the post, a day all students dreaded, so Jane drove her to her parents house after a quick inspection of Charlotte's appearance, white satin blouse with cap sleeves and bow at the waist for a belt showing off the narrowed waist caused by the corset, straight black skirt, black heels. The smarter Charlotte and the new hair style took her mother by surprise. After some chat about how they were getting on Charlotte was given the envelop, she needed five C grades or better to move onto the courses she liked, she had only three. This was a big blow to any plans that Charles and his parents had had without the added complication of him now being Charlotte.
Her mother and Jane had always been direct, no nonsense women and quickly assesed the situation, Jane spoke 'Well I don't think six form is an option for you at the moment is it. You lack the grades and being Charlotte will make your life very awkward at least till everyone has got used to you. Now I think what might work best is, you come home with me and have a week or two, look at other college courses or the possibility of getting a job, none of which is going to be easy, but you have to do something either as Charlotte or Charles' And with that they said their good byes and left for Jane's home.
Charlotte was given a couple of days to consider what she wanted to do, then after two glasses of wine Jane broached the subject of what she was going to do with her life. Relaxed by the alcohol Charlotte spoke freely and told Jane how much she had enjoyed being Nial's girlfriend, the whole confusion over whether she was a boy or a girl was difficult, but being someones girlfriend had felt special, when Charlotte later divulged the fact that she was not a virgin, Jane said she was not surprised and rather expected it. But when it came to what to do in the future Charlotte had no idea. Jane in her plain speaking way explained how Charles had never made a decision in his life, his mother always told him what to do, but now his mother was at a loss as to what to do, and it seemed Nial had a greater influence. So Charlotte could do what his mother wanted, do what Nial wanted or make a decision herself. It did not take long for Charlotte to think it through, for once he did not have to do what his mother wanted, and in doing that it would mean she could stay as Nial's girlfriend, so as the last drops of wine were poured out of the bottle she announced her desire to live as a girl all the time. Jane pointed out it would mean having to tackle the rest of the family, some might not approve, she still needed to get a college place or a job and that she ought to go home and clear out all of Charles's things. This was said more to challenge her commitment.
Charlotte had two weeks of holiday left and spent it looking at college courses, the job section of the paper and online, then there was the housework to do, washing, cleaning, ironing, cooking, it all took time. At the end of two weeks Jane felt the need to get Charlotte to make a decision. Charlotte had rung a few places but as soon as it got to the point where she had to say who she was her bottle went, she could hardly turn up with paperwork saying Charles when she clearly was a Charlotte. This simple problem stopped her getting any further, so Jane stepped in once she saw how awkward the situation was. A phone call to her sister and it was all decided, there was an appointment with a gender specialist the following week and depending on the outcome of that, Charlotte/Charles future would hang.
The specialist was a very nice woman who put Charlotte at her ease, after some talk about feelings and looks at notes and blood tests followed by a physical, she invited Charlotte's parents back into the room. Her advice was not to do anything drastic until she was 18 for legal reasons, but from the tests Charles could never function as a man fully, but then as Charlotte she would never be a real girl even after surgery. It was Charlotte who saw that she was not going to be either a boy or a girl without a conscious decision, she was non gender if that was possible, so she asked if that meant she could choose, the specialist agreed that given her hormone imbalance even after the pills she had taken, it would appear she had a chioce. Charlotte turned to her family and announced that she wanted to be a girl. Her mother held back her tears, but Jane had seen it coming and after hugging her sister whisked Charlotte away so as the truth was not so real for her sister.
Once home Jane sat Charlotte down and did one of her bossy speeches where she laid her law down.
'If you are staying with me as a girl then these things will happen'
You will never do anything remotely boyish.
You will take your pills and turn up to the counselling without fail.
You dress code shall be ultra feminine, at least to start, say six months.
Nial is welcome but if I catch you doing anything that you might have done with him as a lad then he is gone.
You will start working for me next Monday as my apprentice seamstress.
Charlotte asked for some clarification on some points, ultra feminine meant, heels, corset, stockings, skirts, make up, nails, hair, all had to be on a scale of one to ten at least a nine. She agreed to never do gaming with Nial again but asked if he would be allowed to stop the night, Jane was a little taken aback by this one, but insisted that he could as long as she was the girl in the relationship, and no she would not be checking up to make sure, and she would not be telling her mother about Nial stopping over as long Charlotte did not mention about her own girlfriends who sometimes stop over, 'my sister is such a prude at times' was the last comment on that subject, although Charlotte quickly worked out what her fathers odd comments about Jane's lack of a husband had been about, aunt Jane was gay and that helped explain alot. Maybe the 'law' that needed most explaining was the seamstress one. Charlotte did not know what one was so Jane told her how she had left school and worked for a tailor before making clothes on her own and developing that until she now ran a few fashion and bridal shops. Charlotte could work for her without the need for her identity being questioned, and there was also the fact that during their time together Jane had noticed how ebthusiastic Charlotte was about clothes and fabrics which meant she may well be good at making and possibly designing them once she knew how to do it. Charlotte was sat there taking in all this information and feeling rather overwhelmed by the days events, first the doctor had explained the medical situation which was enough to handle for a day, but now Jane was laying down rules for her continuing living with her. There were doubts creeping into the thinking, what if I do tire of being a girl, what if I want to be a boy in a years time, what if Nial dumps me, what if....... All these questions were running around her head.
Jane brought her back to earth 'Charlotte will you accept that if you stay here then you will stick by my rules?'
Charlotte wanted to say can it not be a little more relaxed, just see how it goes.
Jane waited a minute or two 'Ok young lady, either you accept that be Charlotte for the foreseable future or you can pack your bags right now...You have had plenty of time to think over the past weeks. Now is the time for a decision'
Charlotte started to say 'What if' but was cut short.
'If we are going to say what if, then the only one I will ask is, what if you walk out and go back to being a boy, what then, you will be an impotent lad with breasts, far to thin eyebrows and some very feminine gestures, besides all the regrets of not being Charlotte.'
Charlotte was feeling even more pressure until Jane spoke again 'Right as you can't make the decision I shall do it for you. I would hate to see my newly found niece turn into a nephew, and as you will be living under my roof, you are going to be the prettiest, most feminine young lady you can possibly be. You will never complain about anything unless you think it makes you look unattractive, you will follow my ground rules from now on.......understood?'
Charlotte did not have the nerve nor the will to object, and just nodded in agreement.
'Right the first thing you are going to do is let me see you in your underwear, pick your nicest set and not necessarily a padded one, then come out here and let me take a look at you' Charlotte did not get up 'Come on snap to it Charlotte' she said a in rather bossy tone. Charlotte went to her room and underdressed as instructed, putting her favourite black satin bra and knicker set. Then very self conscuoisly went to find her aunt.
'Excellent, I like the satin myself, your breasts are rather too big for a lad you know, nice size for a teenager girl though......but I think you need to find someway of making the panty area better looking, no one wants to see your boy bits, no matter how tiny they are. Might I suggest some tape you will find in the bathroom cabinet. Right off you go and see what you can do, then come back and show me what you look like without that lump'
Half an hour later and after much fiddling with the remains of her manhood, Charlotte returned to her aunt barefoot 'No heels, what have I told you girl' Charlotte scurried off to find some shoes. 'Thats better, now let's take a look at how the girl is looking.....move your hands Charlotte' she was holding them across her front hiding the privates. 'Doesn't that look better. Can you tell without the pants on?' Charlotte was standing there feeling so embarrassed that she found it hard to speak, 'Well if you cant tell me, you had better slip those knickers down and let me make up my own mind' Charlotte slowly slipped fingers into the waist band and inched the knickers down 'All the way dear, and the bra as well please' Charlotte just wanted this close examination to end so removed the underwear and stood before her aunt. 'Have you looked in a mirror? That is fantastic, I reckon you could go anywhere and no one would be any the wiser, even naked your little bush looks just right'
'Can I get dressed now'
'Why? do you not want to enjoy the freedom of looking like a sexy naked young woman?'
'I just feel exposed'
'Ok go and slip into a dressing gown'
While she was getting her wrap the door bell rang and Jane answered it, Charlotte felt sure she could hear Nial's vioce but not what was said, which she might not have liked the sound off. Jane was telling Nial that Charlotte needed reassuring and confirming in her present role, and though she did not see the attraction of men, if Nial was to be a man with her making her feel like a woman and make her feel as though she could never be a man, in Jane's words he would be doing ok. He went in to find Charlotte dressed only in the wrap.
After a kiss and a hug said 'You looking hot tonight Charlotte, do you fancy going out?'
'No need to go out on my account, I was just off out myself, you two stop here and enjoy yourselves' while giving Nial a long stare, they were stopping.
It did not take long after Jane had left for Nial to discover that Charlotte was wearing nothing under the wrap and the little dick had gone. 'Fuck me' Nial excliamed
Charlotte chuckled and said 'I can't, it has to be you that fucks me'
'That is true, are those tits still as sensitive as they were a few weeks ago' he stroked one and Charlotte took a quick breath, 'Yes to that then' It took ten minutes for them to get to the bedroom and for Charlotte to have her legs up allowing Nial full access to her hole. She put up no resistance, Nial just took her and did not let her resist. By the end they were both spent, and Charlotte knew she had enjoyed herself with the added pleasure of giving Nial what he wanted, which rather meant she knew her place. She was Charlotte, Nial's girl, Jane's niece and all that entailed.
When Jane got back they were sat like good teenagers watching some reality programme, Nial an arm around her shoulders, her legs tucked up beneath her.
'Oh hi aunt' she jumped up 'can I get you a coffee or anything'
'Why, thank you Charlotte, I will have a coffee'
While she was away she quickly found out that Nial had done as requested, to make Charlotte feel secure in her role as his girlfriend. She did not ask how but did guess the basic facts. Shortly after Nial left, after a cuddle at the front door he asked if she would always be his, she told him she could think of no one she would rather be with. He knew he had accomplished his part of Jane's plan and would need to be around to make sure he stayed her favourite.
Back inside Jane asked if Nial had been good. Charlotte said yes without specifying in what way he was good, Jane might not approve. But Jane changed the subject and asked her about the future, Charlotte still full of the pleasure of being with Nial just told her aunt that she would do whatever she wanted as long as it did not include having to register anywhere as Charles.
'So you will abide by my rules?'
'If that is what you want, then yes I will stick to your rules'
'Great, now then remember any slacking and I shall send you back to your mothers and you will have to cope with her and your rather girlish body'
'Yes aunt'
'Right on Monday I will get you started on some basic sewing and we shall see where we go from there'
The dining room soon became a workroom where Charlotte was left to learn about sewing, patterns, fabrics, and style, on top of all her household duties and feminising rules which soon included a corset as she was slouching over her work without one. It did not take long before she had made her first skirt and not long after that she was making all her own clothes, delighting in the new skills she was learning and seeing a purpose to the learning. As her competence grew so did her ability to adjust patterns eventually designing her own, and being given some wonderful fabrics to work with. Another benefit of spending time at home was that Jane could ask her to make, say a long dress, then insist she wear it to find out whether she had made a good job. This was no problem for Charlotte as she had always liked outfits that made her feel feminine and the ones Jane would make her wear always had something difficult but feminine to control, like a long skirt, or bell sleeves.
Jane also insisted that Charlotte keep her nails long which was awkward when sewing, but felt it added to Charlotte's rapid femininising. At the end of the first six months Charlotte walked on her toes even when barefoot, her achilles and calves had shortened so much, she sat upright even without the corset and could never be taken for a boy due to her bigger hips and larger chest thanks to the hormone treatment. Her mother grew to accept that she had another daughter, though her real daughter was a little miffed that she was not the only girl any more. Harder to take was Charlotte's grandparents refusal to accept that their grandson was different which caused stress in the family, but Charlotte had to cope with it. And the best way she had found of coping with problems about identity was to let Nial take her to bed and treat her like his girl, even if she did not come, he would still have used her as a girl and that was enough to reaffirm her status. That was the emotional response, Jane's longer term feminising was have a deeper effect, though Charlotte could not walk like a boy and physically in knickers looked like a boy, Jane was constantly pushing her into female situations. Charlotte had to go to a salon once a month and have her hair restyled or coloured, she was to keep her skin tanned with moisturiser and was encouraged to only wear the most feminine clothes.
By the next summer Charlotte's life had changed completely. She had a regular boyfriend in Nial who had taken a gap year, found a job working in computers and loved it, so when the time to go to uni came he turned it down in favour of vocational trianing with the company, which also maent he stayed local. Charlotte had learnt quickly how make, design and alter clothes and could make all her own clothes, Jane was giving her customers items for alterations which meant Charlotte was earning her keep. Charlotte was not socialising with many besides Nial's old school friends when they were back from uni, but she was having to go out, first to do grocery shopping and on dates, but as she grew confident in her ability to look totally female and with her sewing skills, Jane would ask her to see customers who needed a dress altering. Which meant being very close to complete strangers and not letting on her true identity.
The autumn brought about a confidence in Jane and suggested that they attend a fashion show together, but it was not just a look at the new ranges manufacturers were hoping she would but, it was a proper designer show with outrageous designs and a sense of theatre to it. Jane asked Charlotte to make her a cream and gold dress with a full skirt, narrow waist and big chest, basically a 50s retro look, and told Charlotte to make herself something to wear, it could be anything as long as it was good. Come the show Jane has a disc skirt with a corseted top and short bolero jacket, she loved it, Charlotte had made herself a dress out of layered cream chiffon which hung from gold halter neck bra line, she looked so adorably feminine Jane wished she was gay like her. The night was great event and Jane did plenty of networking while Charlotte just took in the styles and images from the show thinking how she might use some of them in her own designs.
I was between the show and Christmas that Jane sat Charlotte down. She would be eighteen soon and could make her own chioces without any input from parents. She had also been living at Jane's for 18 months, so now was a good time to reassess what the future held. Charlotte was happy to let things happen, to sew, to see Nial, to live with Jane. Jane made it clear she could not stop with her indefinitely, why not move in with Nial was Jane's suggestion, live with someone her own age. Jane also wanted her to work more in the shops dealing with customers than before which pushed Charlotte out of Jane's house even more.
So the next time Nial was round Charlotte told him what her aunt had talked about, Nial liked the idea of having Charlotte fulltime but saw it as a chance to push her into being his girl completely. He told Charlotte and later Jane that he would love to find somewhere for him and Charlotte to live together but his condition was that Charlotte had surgery to enhance her already female look. When asked what he meant, he explianed that her would like her to have a proper girls hole primarily, to get rid of the little remains of the boy adding cheekily that breast implants would be nice as well. Charlotte at first objected, somewhere deep inside she felt she was still a boy all that had happened was just a series of unfortunate chioces made by her and Nial at first which left her with only one practical way to go, but surgery felt quite final, stopping any chance of return. The subject had come up in counselling and she had always rejected the idea. Now however with mounting pressure to comply with Nial's desires she capitulated and shortly after her 18th birthday had her name officially changed, followed by the removal of all traces that Charles had ever been around. The final act was to have the surgery, Nial saved up but Jane helped with the costs so it could happen sooner than later. Charlotte emerged from hospital very sore and well bandaged but with rearranged crotch and an extra cup size making her a good C.
Charlotte's fate was sealed when she moved into Nial's small rented house, it was hers to be herself in, though in reality it was Nial's to have her be what he wanted her to be, and for many years to come it was to be his hot chick that he dreamt of all those years ago when he first saw his friend in a photo wearing his sister's dress to a party. He was happy with the outcome, and Charlotte was content to feel wanted by Nial, and have a job she was good at and enjoyed. The being a girl was not too bad either.
How far would you go?
Matt and John were always competitive, they would go to the gym and have to do more distance, time, weight, whatever than the other, and they would challenge each other over fitness as well as random things, but whatever they did it was never certain who would come out on top. They were also gay and had the stereotypical fit and toned man look, wearing tight vest and trousers to show off their hard won physique, but neither fancied the other as they were both dominants and would not want to be the others bottom, both however did have steady and reliable partners who worshipped them, Jamie and Paul thought they looked great, and though wanting to look toned did not have the frame or body shape to achieve anything masculine, so happily fell into being Matt and John’s submissive partners.
One Saturday night they were out as a four and things were going slowly when a transvestite came into the bar, he was a terrible advert for the cause, matted wig, visible shadow on his face, beer belly and badly put together outfit. They all made fun of the poor unfortunate but it had set a seed in Matt’s mind for a challenge.
Sunday morning found Matt and John running in the park and discussing the previous evenings events. Matt commented on the TV and John agreed he was terrible, then Matt suggested Jamie and Paul would make better cross dressers given half a chance, John agreed but went further suggesting that Paul would be better than Jamie, and so the challenge was set. By their next Sunday run they had to get their partner into something female, without them knowing about the challenge, otherwise it would be too easy.
The week rolled by, and Sunday came on. Matt had managed to get Paul to buy new trainers but not from the men’s section, from the women’s they were light blue with silver detail, very nice said John who had got Jamie into wearing an apron when he was cooking. It was now they realised they needed a referee to decide who had won, as there were no references to judge by. They later rang a friend called Angela a close friend of all four to ask if she would judge who had won.
Over a drink the three of them sat down and discussed what they were doing, Angela reckoned that many men wore ladies trainers especially as they were a slimmer fit, and an apron was just convenient and practical, so judged them equal. Disappointed they went off sure that by the next weekend they would have got their partners onto something properly feminine.
Once again they needed Angela, John had bought Jamie a short nightie telling him it would turn him on, Matt had persuaded Paul to use lip-gloss. Angela felt lip-gloss was something many gay men might use, but the nightie was the winner, just a shame it had been a private affair. Matt felt he could top the nightie and said so, saying by next Sunday he would have Paul in something to top the nightie.
The following weekend Matt was confident, he had persuaded Paul to try silk knickers, which Paul apparently loved the feel off. This re ignited the challenge,
If Paul would do this then Jamie would surpass it.
By the following Sunday Jamie was wearing knickers and camisole sets as well as his new found nighties, the newest being full length, satin, lace and pink. Paul had been persuaded further and he too was wearing camisoles under his male clothes. Angela judged it a draw, but suggested instead of trying to compare different things she would give them something to achieve, for that week she suggested complete loss of body hair, they agreed.
By the weekend both men had hairless partners, and both said how nice their skin felt to touch and that they would be keeping Jamie and Paul hairless from then on. Next week she said she wanted a night out with them, they had to be wearing the underwear, which both knew was not a problem, but she wanted to see either arms or legs to verify the hairless body challenge, and for that weeks challenge they had to wear a delicate piece of jewellery, not a chunky man’s piece.
They turned up at the appointed bar, Jamie in a t-shirt; Paul in a sleeveless top Matt hoped to show Jamie’s off bare armpits for a bonus. Jamie however won with the jewellery; he had a thin neck chain with a stone hanging from it as well as a delicate chain around his wrist. Paul did have a ring on his thumb and a ruby stud in his one pierced ear, but Angela felt Jamie had it that time.
Their challenge for the next week was to get the boys to have both ears pierced. But this proved quite easy, both relationships easily accommodating this demand.
The following week she wanted them to get Paul and Jamie to have a manicure, not that hard, but to keep a coat of polish on them, she did not say a colour so both ended up with clear polished nails.
For her next idea Angela thought one of them might refuse at a salon, she suggested highlights or a colour change, something she knew some gay boys would do, but at a salon, that she was unsure about.
She had underestimated the willingness of the boys to please their men, Jamie was now a blonde and Paul had silver and gold highlights in his mop of a haircut.
For what she said would be her last idea because no one seemed to be winning, she asked if they could meet up the following weekend when the boys should be wearing something that screamed female and for all to see, nothing like underwear this time. This time she felt sure one of the men might give in, or one of the boys might refuse to wear whatever it was they were being persuaded to wear.
Jamie was bought a lemon angora top with an unusually deep V that on a woman would display some cleavage; he liked the gift and needed no persuading to wear it out that Saturday. Paul was less obvious he had on white cotton trousers that hung to his hips and flared out to unbelievable hem lengths, Angela’s response was to declare it a draw, both men could get their partners to do whatever they wanted and both looked comfortable in their feminine styles. But this last challenge sparked something between the boys, seeing each others new clothes and realising how they had both got piercing together, been and had their hair coloured, worn jewellery, and when they talked found out what the other was wearing underneath, it was obvious they had been used as a challenge, Matt and John both admitted to what they had done, but insisted they had only improved their looks by doing these challenges, there was nothing detrimental, and the boys agreed because they loved the soft underwear and nighties as well as the changes the challenges had made to their appearance.
The following morning while the men were out running, Jamie was round at Paul’s discussing what the other had actually done, Jamie liked the cotton trousers Paul was wearing and offered him the lemon top to see how they combined for a look, and both loved it. Then they got around to the nighties; Paul got his long satin one out and Jamie immediately announced he was getting one also. They knew the challenge had come from the sight of the ugly TV, but now they were cross-dressing themselves they wondered how far they might take it themselves. They choose not to push it too hard because they were gay men and going to feminine might put off their partners, so they would give it a week as things were, basically the underwear and nighties to judge how Matt and John would react to them staying ultra camp. This went so well, neither Matt nor John objected to Jamie and Paul still wearing the knickers and nighties, even making it clear they were staying in one evening to clear their body hair created no complaints. This meant that Saturday morning the boys would be out shopping. The men had been able to say the purchases were for a girlfriend as a gift, but two camp men buying first a long satin nightie, then a cream roll neck top from a woman’s boutique was causing them to get embarrassed and have fits of giggles. But by the time they had bought trousers for Jamie they had got used to the awkward feelings and were just going for it. So much so that as they passed a make up counter they bought lip-gloss and mascara knowing that they had seen boys wearing these already so should be fine for them.
That evening they were out as a four as they always seemed to recently, only this time the boys wore their female clothes, jewellery and make up and loved it. Feeling completely at ease with their partners who were the clearly dominant men while they fulfilled their role as the sissy in the relationship. After a few drinks they plucked up courage to ask what Matt and John thought of their look, John just kissed Jamie very powerfully, while Matt asked if the long nightie was still available. A positive result.
On the Sunday, the boys were chatting on the phone seeing how it had gone the previous evening, and when they both realised how well their purchases had been received they were left with the dilemma of what to do next in this cross dressing adventure. They could go straight for skirts but felt their men would baulk at this so wondered what they could do without going full on.
It was now their turn to contact Angela, they knew her part in the challenge and thought she might like to continue it but in a reversed way, what could they get away with before comment was made. She told them not to get their haircut, to let it grow, but to maintain the new colour they had got. Also to file their nails not clip them, and let them grow a little. All a bit long term they felt but definites for the future. For a more immediate challenge Angela suggested wearing some of their new clothes daytime, maybe even try out the make up daytime in the week as well.
The following week found both ringing the other to tell what they had done, Paul did the weekly shop in his trousers, Jamie went to work with mascara on one day, which inspired Paul to try the same. By the weekend they were so excited they wanted to shop for more things. Paul bought himself a matching nightie and wrap saying how this would work magic on Matt. Jamie bought another top, this time a soft cotton kaftan but did think it might be too much.
He need not have worried the top was a hit with Matt, while John suggested Jamie be a little more adventurous in his clothes selection. For their Sunday chat they could only say wow that went well. Jamie was going to try out the nightie and wrap that evening and would let Paul know how it went. But by the Tuesday both had decided to see how mascara fulltime went, upping it to lip-gloss in the evening by Thursday.
They kept it at this level for about six weeks, the mascara became fulltime, Paul was able to wear his trousers more often, but that was just because he worked in a call centre and Jamie worked in an office that was a bit more conservative, but he did try out his tops on several occasions without comment. They did shop and increase the number of tops, Paul bought a kaftan style top and enjoyed the girlyness of the look as well as the attention Matt gave him.
It took about six weeks for the piercings to heal, but by that time the roots were beginning to show in their recoloured hair, so Angela suggested they have a trip to a salon to get their hair sorted, but then as a challenge they should buy some earrings and see how girly they would be prepared to go in with the style.
Their next Saturday was now full, a salon visit then shopping, nothing drastic, just getting the roots done and a bit of a trim to tidy up the ends, but Angela had insisted on nothing too much being cut off, they had to wait till the length was better before cutting was a real choice. Then it was off to find some ear decorations, first they looked at small rings with a stone or a fancier stud, but these they knew many men, not just gay men would wear, after much looking and Jamie getting distracted and buying himself some new underwear, Paul bought a pair of hoops and Jamie chains with fine tips that allowed them to be threaded through his holes. They were not allowed to point out to their men what they had bought; rather they had to wait for them to be noticed. Unsurprisingly both earrings went without comment, meaning, according to Angela, they were not feminine enough and they needed to try again.
For the next weekend Paul had big hoops and Jamie a red stone dangling from each lobe. This time the jewellery was noticed and for the first time were referred to as girls, well they were in full feminine outfits of cotton trousers, soft short tops and make up, not to mention the jewellery of earrings, as well as necklace and bracelet they had worn before.
Buoyed with the success of the fun they were having, they wanted to try another challenge, yet at the same time their wardrobes would increase and the small collection of jewellery was bound to increase. Paul started with a chain bracelet, Jamie followed with a necklace and an anklet. It took three weeks before they went out fully glittered up, non to discrete earrings, pendant necklaces, bangle style bracelets, a couple of rings and for Jamie his anklet.
The men’s response was very supportive telling them how nice they looked, encouraging them to dress more femininely all week and not just at the weekend. Angela recognised that the jewellery had not found their limit for femininity, and suggested that they get some shoes from the female stands. The boys had a fright when they saw the choice, nearly everything had heels on them or looked just to butch and practical for what they wanted, Paul found himself some suede sandals with a small wedge heel which were not to dissimilar to his beach flip flops, Jamie did not like things between his toes so settled for a beck shoe, but not a boring blue or white his were lemon which would match the angora top. Angela’s response to Paul was that now he should start doing his toe nails as well with them being on show. Matt and John’s reaction was to just call them girls far more often, but still no one was saying enough it is time to stop this.
Two weeks later Angela challenged them to try proper heels and coloured lip-gloss, she felt this might just make them look like and feel like girls, maybe crossing a line they did not like. But she was wrong, the shoes were conservative, low block heeled courts and the lips were certainly pinker now, but they did look more feminine.
Having failed with that challenge she told them for their next weekend eye liner was a must and new shoes without block heels, they would be allowed the stunted kitten heels if that is what they liked. Paul did get himself some kitten heels but Jamie bought a pair of boots with a low but narrow heel. They had bought them one evening and then had plenty of fun telling each other how odd it was walking in the new footwear, and that combined with eye liner practise, meant by Saturday they were ready for an upping of their look towards the female. Matt’s reaction was to call Paul Paula which gave everyone a laugh, but it stuck, Paul was from then on called Paula by everyone within the four and over time it spread to the wider circle of friends who had not let it go unnoticed the change in style of the two friends.
Angela had a serious eye contact talk with Paula when this happened, wanting to know if he was happy with the new name, and when he did not look away as he said yes she knew it was for real. So she challenged them to learn how to pluck eyebrows and thin theirs to a shape they liked. First they looked at glossy magazines, then on websites to find out how to restyle their own particular brows, Jamie’s were quite fine already but were thinned non the less, but was not that noticeable, Jamie had darker and bushier brows so when he picked a tadpole shape it was Jamie who asked if it was not to far, Paula said no and asked Jamie to get on with it. To be fair neither had a shockingly dramatic shape, but they were clearly different from before.
It was Paula who now suggested they try eye make up, but Angela had a better idea, first go to a salon, get the roots redone and now their hair was well past their ears and in Jamie’s case well down to his shoulders, it was time to get a cut. She took time to show them hair styles asking what they liked and suggesting what might suit them, this took all Friday evening, but by the time they turned up at the salon they had a photo cut out of a magazine and ready to ask if the stylist could do it on them. Paula’s hair was cut so it long all the way round, needing to be swept back over his head or tucked behind the ears, Jamie came out with a gently waving perm, giving his hair body and lift, and luckily for him enough length so he could tie it back on Monday when he went to work.
Once again Matt and John loved the changes, Jamie being rename Jem. They were not yet fully aware how feminine they looked, but now Angela said was a good time to find out more about make up and how it changes and improves the facial features. This was the first time she had accompanied them shopping but felt there was so much to take in they would need help. She was thrilled when a sales assistant came to help, Angela explained how her friends had no idea about make up, with some story about being student drop out types who now wanted to look more normal, the sales girl lapped it up and offered to give them a make up demonstration. An hour later they walked out with perfect foundation, defined cheekbones, sultry eyes and kissing lips, as well as bags of cosmetics they would need if they were to try and recreate the look. Once outside Angela pointed out that at no time did the girl take them for men, which made the boys giggle. Being in charge of the situation she claimed that as they were looking like women then they needed a bra, and walked them into a store where they each bought three b cup bras, then she made them go into the ladies and put one on and fill them with tissues. They came out looking far more self conscious than she had ever seen them, maybe this was where they stopped, but later that evening she bumped into them, both dressed in all their most female attire, faces still made up and most noticeably, their chests sporting breasts, bigger than a b cup was meant to be. She was wrong this had not been a stopper just a pause.
It took them several weeks of private practise and consultation with each other and Angela before they went out again with full make up on, but it was worth it as they felt more finished in their look. They also liked the feel of a bra, but for daytime wore AA cup so it would not show at the front, but would be felt by them as it wrapped their chests snugly.
Angela was running out of ideas, she could get them to try a skirt but still felt this maybe too much, instead she went for more pronounced shoes, gradually upping the heel height, and once they were happy in 3” courts moved towards 4” sandals, and then onto shoes with no ankle straps, just a strap across the toes to keep them on the feet, meanwhile they had taken to wearing their first female shoes in the daytime and for work on occasion.
Next she persuaded them to try a new top style, they had always picked shorter tops that maybe reminded them of a male counterpart, but this time she wanted them to try a longer top, one that would come well below the hips. Paula took to this easily and bought a black and white flower pattern which stopped below his crutch, actually looking like a mini dress, with a fitted bust and delicate cap sleeves, Jem at first had trouble finding something he liked, and ended up getting a long white jumper that he easily sat on as it was so long. Angela told them they were beautiful and ready for the last challenge. Next Saturday they would going out in a skirt, tights or stockings, that choice was up to the men, full make up, new top to go with the shirt and her treat a wash and blow styling at the salon.
At first they were not sure if they could wear a skirt, it meant taking away the last vestige of their male look, but there was nothing left in reality, so they took Friday off and shopped together, they now looked so female they were comfortable browsing the rails and looking at the mannequins for ideas. It was late when they got home, both had chosen full layered skirts that fell to mid calf, Jem a brown, Paula a green, they had cotton blouses with ruffles at the cuffs, neck and down the buttons, they also had a pair of stockings and tights each but would need to ask before opening a packet and trying them on.
Saturday they meet at the salon early afternoon, dressed quite reserved for them now, flat shoes, jeans, and a plain shirt with only a touch of make up, but they still looked like Jem and Paula, not Paul and Jamie. The stylist did wonders on their hair; Jem’s was given loads of volume and curl, Paula’s was swept across his face and lacquered in place. As an extra unknown treat the salon also painted their now trim nails a vibrant pink and given a lipstick to match them. They had left Jem’s clothes at Paula’s and went there to change, the men had been told that it was to be a special night, a meal and a good club possibly, but all they knew was that they had been asked stockings or tights, both said stockings as they reverted to male stereotype.
The cab picked up the girls at 7.30, now fully dressed in their skirts, stockings, 4” sandals, C cup bras, long pendant earrings, obvious rings, matching necklaces and bracelets and small bags to keep those essential girly bits in like a lipstick and tampon. The cab driver knew nothing was amiss, Matt and John at first did not recognise their partners, both of their girls being on them before they could say hello. There were lots of compliments on how good they looked, some pleasant touching. Then it was off for a good restaurant then onto a club and some close dancing, followed by a night of showing these boys what a girls place in bed is, but they knew this already, that was part of the reason they had worn skirts that evening.
Matt and John had no objections to their partners behaviour that evening, and over the months that followed even encouraging it with presents that might seem more appropriate for a girlfriend, such gifts as scent and jewellery were common over the year. And things seem to settle down after they had worn their first skirts, they were still camp in the daytime, straight men do not often wear mascara and lip gloss, nor do they wear silk underwear but Jem and Paula did, but it was dismissed because they were gay, so camp was to be expected, the full on female look happened in the evenings and all weekend, with the nights being a proper dressing up time, now skirts were included the whole range of women’s clothes were at their disposal, minis, evening dresses and revealing tops became their Saturday night preferences especially if their men were taking them somewhere special and straight.
This part time female life was suiting Jem and Paula when Angela made a reappearance in their lives, she had been away and not out much when she was around so they had not seen her, and besides the odd phone calls for advice, there had been no contact. Then they bumped into each other one weekend when they were in a club dancing, Jem in a crochet top that gave his white satin bra a very visible outline, Paula opting for a tight top instead but with a flared mini as opposed to Jem’s jeans, both on towering 4” heels and with excellent make up, she had to make sure it was them before approaching them. She was thrilled to see they had kept up with the new style, and asked if they were still enjoying it, they told her all about recent shopping trips, salon adventures and the reactions of Matt and John. But it was later in the week when she accidentally met Jem, who was looking very much like Jamie, he was wearing a nice knitted top, jeans and flat shoes he bought from a ladies selection, his hair tied back and no make up. She took him for a coffee and asked why he seemed to be reverting back to boring camp, what did John think, what underwear did he have on, if she saw Paula now would he too be a boy. In short she thought she had left them moving towards full femininity each trying to go one better than the other, but it seems like they have stopped the competition and were actually going backwards. Jem tried to explain he had a job that he thought would not agree to a way-out change of identity, John loved it when he dressed up at the weekend, but close shaves need a few days to recover and after a weekend he needs to let his skin recover.
Angela had some time to herself and pondered her two projects and how they had turned out deciding that she wanted to find out more about the situation, first she contacted Paula to find out if Jem’s experience was duplicated, the answer was, nearly, Paula still wore light make up as his beard was light, but for work his clothes were camp and shoes flat. Next she rang Matt and then John to ask about their partners and find out if they were happy with weekend girls. Matt corrected her when she called Jem Jamie, but was happy for him to do what he likes as long as he was happy, but yes he did like the girl in both Jem’s look and behaviour. John was a little more disappointed she felt, he would like to see more of Paula in skirts but knew how hard it was for him to do it with work and things, so would settle for what he had. This lead Angela to go out and look for fresh challenges for the boys after getting support from the men she invited Jem and Paula to her flat and showed her some websites she had found, it was a mid week evening and they were pretty much in boy dress, so she mocked them for being so conventional saying they should revert back to their old names, being essentially submissive characters they said they were sorry and what should they do. Jem she said should go for beard removal, Paula should wear his bra fulltime again, when he suggested it would be too obvious she allowed him to use AA cup bras, at least to start with. They both had to resume fulltime clear nail polish, she also planned a salon visit, Jem was still blonde and Paula had let the highlights grow out, their hair was certainly longer but the style nothing different from early on really. She would leave a more dramatic style for later, first she had a few other ideas to get on with.
A week passed and the boys were unsure about how things had changed, Jem had been for his first appointment and had a sore face, Paula had gone to work in a bra but felt self conscious in it, but Jem reassured him that they had felt like that before and now look at them enjoying what first had worried them. Angela wanted to know how things were going and was pleased they had done as she suggested, but she was still trying to find the point at which they say no.
A fortnight later, she tells them she has a treat. They already have discovered silicon inserts but Angela wants them to be fixed more permanently, at least Friday evening to Monday morning. And as she is giving the boys their first lesson on how to fix them she realises they never wear tight fitted skirts because they have not worked out how to hid the bulge except with control pants that they don’t like the look off. So having spent time doing research explains how all good trannies hide their bits pushing them back inside and taping the remainder up tight. It takes a while but soon she has two boys who at a glance pass as girls even undressed, but for certain in their satin underwear. That Saturday they had to go and buy something either with bare shoulders, i.e. no bra straps showing, our a skirt that was tight across the hips, in a way displaying the fact they have no bulge. That evening saw them out in tube dresses, one gold the other silver and made up to the nines, their men were very impressed with the new look, even more so when they stripped off at night and retained the shape the dresses had indicated before.
Angela wanted to push them further into being more feminine through the week, which she felt was about the only challenge left. Jem was loosing his beard, and though reluctantly at first now wore a bra full time like Paula. Next she suggested they wore flat sandals full time, which again met resistance but in the end they went to work in sandals that was far too delicate for a man even if the colour was black.
Over the weeks she encouraged them to grow their nails again, nothing long, just neat and rounded, definitely not clipped and short. She had had them on the challenges again for about three months; Jem’s beard hardly showed now and had no excuse for avoiding make up full time though he still would not wear it to work. Paula had been persuaded into wearing light foundation, a lip-gloss and mascara fulltime, and with the other fulltime changes was starting to create gossip at his work, which was starting to worry him a little. Now Angela wanted to see if she could be bold and make a final dramatic change, she checked it out with Matt and John first, and then booked the salon. The boys thought they were just going to have roots and a tidy up. What they got was a complete shock, Jem realised something was up by the amount of hair on the floor, his blond roots had been done but the style was like something Bowie had in the 70s long feathers with spiky on top. Paula faired no better; he was now auburn with lots of tight curls tumbling down to his shoulders. They both loved the new styles and wanted to dress up and go out. They thanked Angela profusely, the look on her face was that of a proud mother, but they all knew that Monday was going to be a hard time. Matt and John loved their boys new look and told them Monday was not a problem, they looked great, and in their dresses dead sexy.
They had a fantastic weekend being totally girlie, but Monday was hard, Jem could not tie his hair back and had to show up with it just a little flatter than when he walked out of the salon, Paula could get a pony tail but the new colour and the curls still showed in the tail. By lunch they had both had trouble, Jem had been into see his manager who told him the hair had brought to head the issue of his appearance and though not inappropriate for a girl it was not good on a man, and though company policy would not stop him, he was asking him to be a little considerate to the company and his colleagues feelings. He was almost in tears when he rang Paula who had not had any company problems but some of his work colleagues were taking the piss with comments about his look. By the end of the day they were glad to get home and escape. It was Matt who had a solution, he loved Paula best at the weekends when he was a full on sexy woman, and his reaction to the comments at work meant that he would probably revert back to a more Paul look, so he called John and Jem inviting them for a meal. This kept Paula occupied preparing the food while Matt made a few calls, by eight he was ready, John and Jem arrived, Jem had been persuaded to be a bit girly and wore a dress, but something rather subdued really. Then as they got past the pleasantries Matt was cornered with questions about what was this all about. He started with a bit of a monologue explaining how Jem and Paula came to be attractive girls, and how he felt responsible for starting this chain of events, and how he loved Paula even more when he was looking female sexy, and knew John felt the same about Jem, which was odd given they were all gay and did not fancy women, but today had caused a problem, and he did not want to go back a couple of years and loose Paula and get Paul back. So he had a suggestion, they pack in at their jobs and work for themselves, doing what? are you mad? they came back with, but he was ready, everyone knows gays are more careful about being clean than straights, well the urban myth says so, and Jem and Paula are great housekeepers, so he had rung around and there seemed to be a market in the gay community for gay house carers.
They were a bit stunned at Matt’s optimism but he persisted with his idea explaining how it would work and assuring them it would succeed until the boys agreed to give it a try, there was one proviso made by John, there was to be no toning down of the girl in them any more, he wanted his weekend girl to be a week day girl as well, this would not be a problem it seemed.
They advertised in gay papers and amongst friends and soon had enough work to keep them busy, and enough money for clothes, shoes and make up so it was considered a success, being female fulltime was fine. It was some two months later Angela was chatting with them, she was really pleased with how things had worked out for them and how their femininity was blossoming, then she suggested a new challenge, she knew their men liked the fact they were really boys and that they have boy bits, but had they considered breast implants, then they could throw the falsies away, feel with their nipples and enjoy going braless with just a silk camisole on. She could tell from the quick glance between the two that she still had not found something they would not do to be feminine.
As companies are liking their employees to all look alike, some think this is a good idea, others dislike the styles imposed on them.
It is odd how things work out; I had been working at the same office for several years. It is a small unit of 6 women and myself, two do the front desk enquiries, while the rest of us do the paperwork, as well as postal and phone enquiries. Jane is the office manager, and we all get along fine, the work gets done and head office interferes little.
Then head office did interfere, in keeping with many large corporate organisations someone decided it would be a good idea if a corporate style was adopted, this was obviously decided by some one who would not be wearing the uniform, and most of the unpublic faces were given the option of styles, all in a brown and cream colour scheme. Men had little choice a suit with shirts, and a tie with the logo; the women had more choice, a dress, blouse and skirt or trousers, or a suit with blouse. Jane gave us all a form to fill in, with sizes and styles preferred, at least the suits would be made to measure. I filled out mine and ticked suit, though I really had no options. Then we waited 3 weeks until a delivery arrived, there was a box each, Jane made sure we signed for our own parcel, then at lunch the women went to the ladies to change, to see if the clothes fitted, then to show off and compare their choices, I intended to just take mine home and return in the morning wearing a suit, I did not see a problem. Jane asked me to check it fitted then if it didn't fit she could sort it out quickly. Persuaded I opened the parcel, to my horror it was a suit, but a suit with a skirt. Jane then did have a problem, she rang the stores who laughed at their mistake, "Lesley is a bloke, silly us we thought your office was all women, easily sorted, take about 4 weeks to get the new one". Then Jane had a call from head office telling her a few of the executives would be round some time next week, how impressed they were with the new clothes, it being good for identity as well as morale, so they hoped all ours fitted well as they hoped to see us all smart in the clothes.
Jane called me to one side and explained this problem, next week I should be in uniform, but I would not have one that quickly. There were a few options open. To go sick, except it would look odd if I was missing, wear my normal clothes and risk the wrath of the visitors, or wear the suit and keep a low profile, just blend in, which would be easier in the suit than in my own clothes which were not brown. I fancied a week off, though this would mean the others covering for me, and really wasn't justified. To go against policy and wear my own clothes would be to attract certain discipline problems for me, Jane and possibly the rest of the office. I know this is extreme but I was panicking and not thinking clearly. Maybe I could just sit at the back quietly. I went away to think but Jane came to ask my decision rather to quickly. I explained how I felt about skiving, and that my own clothes was out, then with a twinkle in her eye, Jane said she would discuss the possibility of there being an all female office.
At lunch I went out to the shops, but felt an odd atmosphere when I returned. Jane as leader made the announcement, tomorrow I was to dress in the suit, and suitable accessories, then if they felt I was not embarrassing then I would have their support, if not I would have to wear my own clothes and face the consequences, even though it was not my fault. The thought of them being embarrassed, how would I feel if it went wrong, embarrassed would be a kind word.
Jane came to me later, there was only one who felt it wrong, the rest were fine as long as I look good, not a bloke in a dress. Then invited me to her house for the evening, she wanted to help me look good. Being single this was no problem, it was Monday and I only watched the television on Mondays.
After work I picked up the parcel and followed Jane to her car feeling a sense of doom. Being a bossy type, Jane soon told me what we would be doing that evening. When we arrived I was shown the bathroom, told to undress and shower, then shave all over. Jane would make dinner; I was left bra, knickers and a dressing gown. I was then asked about sizes, chest, hips, and shoes. Then I could hear her on the phone but I could not quite hear what was said, and Jane would just say she was getting help. It did not take long before the door bell rang, Dawn entered, then a while later Jill, these two were the extroverts and often told us of their night time exploits, but for this evening Dawn would use her hairdressing skills, and Jill her beautician skills. Dawn soon had me sat in the kitchen hair washed, the pony tail brushed out, and the ends being trimmed, then with gel and a dryer brushed a flowing style into my dull flat hair. When she finished, she asked if we went through with it could she be more adventurous at the weekend. Next it was Jill, she had a box of make up, which she quickly and skilfully applied, I remember having difficulty not blinking at the mascara, but nothing else was a problem. Jill also asked if she could be bolder at the weekend. I did wonder what they had in mind, but Jane appeared with the suit, some tights, and a pair of shoes. I was left to dress on my own, and then Jane came to sort me out. I was lead to the bedroom and a full-length mirror, uneasily I might add as the shoes had heels. I was bowled over by what I saw; I could not have imagined I would look so good.
Back in the lounge Jill and Dawn were both suitably impressed, and suggested a drink, we relaxed, and I got used to wearing a skirt that came half way down my calves, and a short jacket. A lot was said about how I should behave, but I was finding the clothes dictated my posture, and was aware how feminine I was behaving. When we got to clothing, I was told I should get panty girdles to hide any bumps, and a 36c bra as the blouse needed filling. We also concluded that I should stop the night with Jane, and then she could make sure I looked good before going to work. I could not have done it from home for many reasons; mainly inexperience and I used buses. Jill and Dawn left, and after a nightcap I was shown how to clean the make up off, then shown the spare bedroom. Jane apologised for not having pyjamas, but left out a nightie if I wanted nightclothes, I slept nude that night.
Tuesday
After a sleepless night, due maybe to being in a strange bed, or a strange evening, or the prospect of a strange day ahead, or maybe all three. I was awake when I heard Jane's alarm. I heard her shower and dress, then put her head round the door and suggest I get up as we had a lot to do. Jane wanted me to go to work in the suit, but I preferred to put the suit on at the office, I needed to know that I had escape clothes if it went wrong, and going in trousers seemed a good insurance. We packed everything up and dressed, then while it was still early left for work. Once there we set about getting me ready for a public viewing. Jane did the make up, and then I changed with Jane checking I had got it right, I brushed my hair into a style like Dawn had done, last I went and sat at my desk and waited for the staff to arrive. Most were early, coming to see the entertainment, I felt like an exhibit, but everybody was kind, and tried to behave as though nothing was different. I just stayed at my desk for as long as I could, but drinks and need for the toilet brought me out at 11.00am. I walked as well as I could across the room and made for the gents. Upon my return the chat suddenly stopped, it was time to brooch the subject ' so what do you think, do I look good enough?' I looked round, nobody said anything 'I'll go out again then you can talk' I went to the small kitchen area to make a coffee, then sorted out the regular order and found the biscuits. I could hear the talking, but indistinctly. I waited then picked up the tray, silence as I entered and passed the drinks around. ' Well?' I looked at Jane, she quickly gave a look around ' It is up to you, but we feel you look OK, but you need to act more feminine to be convincing. If you are prepared to be taught, we will try to get you to act the part.'
So that was it the office was all female. Jane came to me later and had thought about the training, as we had less than a week she wanted me to stop at her house, and stay female all the time, so becoming used to the new me with out having to swap back to the male me. Then she asked for the bag with my male clothes, I gave it to her then she said I could have it back if I asked, and locked it in her locker. It later dawned on me that I would have leave the office in the suit. I worked trying not to think about it, but eventually we closed and Jane stood at the door with the keys, nervously I looked outside and feeling it was emptyish stepped out, Jane was by my side, the few minutes to the car took ages, followed by an eternity sat in traffic convinced everybody was looking and wondering why I was dressed like a girl. Jane reassured me, but I was still glad to get to her house. I had rung a neighbour to say I would be away and gave Jane's number as a contact, or the office, so I would now spend the week living with Jane as a woman, how odd life turns out at times.
Wednesday
Jane had me walking around in heels permanently, at lunch a few went to the shops, returning gave me a carrier bag and some receipts. They had bought underwear, tights and a handbag, and I was to pay, this was something I had not considered, but did not know how to object. I sneaked a little look; they had bought lacy and silky bits that felt totally wonderful. Going back in the evening was less anxious, but still a relief to be indoors. After tea Jane wanted to see the shopping, then encouraged me to try some on. With ease we talked about breasts and genitals. She would enquire about prosthetic breasts, and I could find a way of concealing my maleness so the knickers fitted properly. I spent the evening in a silk bathrobe, and slept in a nightie. I was relaxing and enjoying the sensations of the fabrics; I even stated how dull male clothes were. All the time I was being picked up on the way I sat, walked, stood just about anything I did was wrong, but I was told so gently I enjoyed learning.
Thursday
I had to get myself ready, being inspected before we left. Work was fine, plenty of encouragement. There was talk that I should go out soon as part of the getting used to being female. So Jane stopped at a supermarket on the way back, and told me nobody would even look at me. With lots of fear I eventually left the car and pushed a trolley very carefully for my host, we did not buy much, but enough to bolster my ego.
'Tomorrow night we go out for the evening' Jane was definite about that. ' And Saturday we have an office outing in town?' it sounded like a question I could not answer. I said why not try a quiet pub tonight, but I only have the work suit. When we had unpacked the bags, Jane went to her bedroom, 'Lesley, come in here dear' she had a black dress in her hands 'this is stretchy so it will fit you if you are game. It will show every bump though'
While she cooked I tried to hide my bump. I ate in the dress but had not been successful at bump hiding, so afterwards we tried together.
I should have avoided this really, I was always conscious that I was not well endowed, but letting Jane take a good look, then take hold, I felt it stiffen and I thought of all those girlfriends who had laughed. 'There are two solutions, either you relieve yourself and get it limp, or in some way we fasten it back here' with a swift movement she pulled it between my legs, the stiffness went. ' Right I will get some tape, I suggest you shave yourself' 'pardon' 'trust me this will work'. I returned bald, to my surprise the testes would go back inside then we taped the penis so it faced backwards. I pulled up the knickers, it looked good. ' Now you'll have to sit to pee, I noticed the seat being up' she winked ' I'm just reading this tape packet, it's meant too stay on I'm afraid, so hope you like it, taking it off will be painful, sorry' I pulled the dress down, nothing showed at all, then reading the package, sure enough this was tape to stay on, I only wondered how long before I would have to replace it.
I caught myself thinking like this on occasion, but was not sure what it meant. I relaxed and decided to just go with the flow and enjoy myself. ' Are we ready for out then?' asked Jane. I smiled and nodded, ' as ready as I ever will be'. We drove to a pub just outside the estate, Jane wasn't a pub sort of person, but felt I needed public exposure.
Sat in a corner we watched as people came and went, after a few drinks Jane told me it was my turn to buy a round, and she looked adamant, I carefully walked to the bar, then in panic forgot what to order and asked for two lagers because the pump was in front of me, I paid and returned. 'Well done, unusual vodka but I didn't reckon you would do it' I drank some 'I'm really pleased with you, I thought of doing this tomorrow, but maybe we could do something else instead' We walked back to the car, Jane linked my arm, ' you enjoying this?' she enquired, 'how do you mean?' ' Just simple are you enjoying wearing a dress?' 'Maybe not enjoy, but it is fun, a challenge, bit reckless, many things I suppose' 'tomorrow night we go late night shopping and I would like to treat you, but only if you enjoy being a Ms instead of a Mr'. I cannot say we made plans rather Jane knew what she had in mind, I just agreed to her plans.
Friday
We went to work as usual, except we packed a change of clothes so we did not spend the evening in our work wear. Nothing happened at work, lots of discussion as to where we would go on Saturday evening, as well as the constant advise I kept on being given about female behaviour. I had long passed the problem of which toilet, but there seemed to be thousands of little and subtle things I should now do differently.
After work we changed in the toilets, and drove to the Trafford centre. First we stopped of at a shop selling prosthetic breasts before we arrived, Jane had rung before to see if they had a problem serving me, but were pleased to help. I left with what felt like a couple of kilos of jelly stuck to my chest and pulling at the bra straps, but it gave me a confidence as they moved about of looking more female.
Once at the shops we were truly in for public exposure, and I was very scared at times, Jane kept close, giving me reassurance and advise. The kids were the worst, but fortunately not many saw through the disguise, only once did I hear ' that's a bloke in a dress' Jane just pointed out how many had not noticed, and how many shops had we been in without the assistants saying anything. The gift Jane wanted to buy me was a necklace and bracelet, it wasn't gold but it made feel a million dollars. I even splashed out on some perfume for myself. Eating at one of the very public cafes we had our evening meal, then left for home, (I know it isn't really but it was starting to feel like it). We couldn't wait to get indoors and have good look at the breasts, they had cost enough and we wanted to take a really good look at them. It started with me parading around in my underwear, then I asked if Jane would like to show me what a real woman looks like in her underwear, surprisingly she agreed. Jane is about ten years older than me, but is very trim and looks excellent, I told her so and asked why she wears loose and unflattering clothes most of the time; I did not get a proper answer, but did feel I had stepped on a sensitive area. We got ready for bed then watched a late film. Very relaxing.
Saturday
We rose later than a workday, and ate breakfast in my nightie because I did not know what I should wear. I wore the stretchy dress as Jane did not mind, and we cleaned the house, stopping for lunch then finishing of around 3 pm. We had to be done by then because Jill and Dawn would be calling. I knew the afternoon would be good when Alison called with a bag, it had been her shoes I had borrowed, and she was about my size so I guessed the bag was for me, though Jane took it away before I had chance to investigate.
Dawn arrived first and asked how adventurous she could be; she then showed us some hairdressing magazines with lots of styles in them. It did not take much persuading to get me to have the hair cut into a long style which had a thin fringe into my eyes, the sides tapering backwards with it ending between my shoulders, my hair is naturally light brown but when she streaked it with blondes the effect was wonderful. Whilst this was going on Jill arrived and was soon playing with my nails. When Dawn had finished she had a glass of wine and let Jill get on. There was little discussion about how I wanted to look, but she noted that the hair was obviously adventurous for a man, so she would just follow Dawn's lead. She started off with acrylic nails, then the eyebrows were plucked, I had pulled out the odd stray hair, but now I felt as though I would be bald, when I did look I had a pleasing narrower and higher brow line. Next she taught me how to paint my nails with a deep pink, the long nails got in the way, but not as much as they would later on. Next we had a democratic clothes selection, Alison's bag was emptied and spread around for all to see, the choice was not vast, but more than I could decide on. After trying on almost all the clothes we choose a brown jersey dress, long with a split up the front, the bodice having cream hoops to a round neck and short sleeves. I had to change my underwear to white, and Jane gave me a new pair of tights that were incredibly fine with a lovely sheen. I fastened my jewellery on, then went back to see what they thought. Fine except I had put on my work shoes, now there was a cream pair of high-heeled sandals for me to wear. The nails had been awkward enough with the bra but I could not fasten the buckles on the sandals, Jane, kneeling politely at my feet, did them for me. Then I had the shock of trying to stand in them, which I managed but walking was near impossible to start with, but all the three women could do was smirk, saying they were going to get ready and see me later, followed by, I could always change but knowing how I had struggled to fasten them, they knew I would be in them until someone undid them. So I took Jane's advice and practised walking around the house. After several practices and rests Jane declared herself ready in mini dress with a longer jacket, big heels and truly well made up. She looked really sexy and I guessed many a bloke would be looking her way.
We meet for a Chinese first, where everyone admired each other's clothes, something I had never been in on before, and was a real boost. Alison even said the dress looked better on me than her, I wasn't sure if that was true. Later we went onto a club that did allsorts of music, with a quieter area for the older women in our party. I tried not to be the only topic, but each girl questioned me about how I felt, and was I really going to come to work next week in a skirt, I always replied saying if nobody objects then yes, and nobody did. The evening was good fun, I danced quite a bit even in the sandals, Jane did get a lot of men looking at her, but to my shock I had a bloke approach me and ask me if I wanted a drink, luckily Dawn came to rescue me, but commented on the number of looks I was getting. A taxi finally dropped us home in the early hours, and still excited, we sat up drinking tea, and discussing the night and the future. Eventually Jane released me from the sandals, and we went to bed.
Sunday
We rose late; Jane was still excited and wanted to have another public outing. A country pub and a walk in a park. I had Alison's clothes to use, so set about choosing a white top and a grey skirt, with a pair of black courts, Jane had trousers which I felt more appropriate, but I had none of my own, so had unresistingly to wear the skirt. The pub was fine, we ate in a quiet corner. The park revealed a horror, I saw a neighbour, not one I knew well, but I was sure to be recognised, Jane held my elbow and walked close, telling me they would not guess, and if they did so what, I had enjoyed the past week, so was I going to let someone I hardly know spoil it. It did take quite a while after that before I relaxed, and was able to agree that a life in skirts was most agreeable, which seemed to please her.
Monday
A normal day, if anything was now normal. Work followed by a quiet evening.
Tuesday
Same again, except the two older (in their 40's) women showed concern about me making a mess of the visit that was due. I repeated that if anyone wants me to stop then I would. But nobody did.
Wednesday
It would have been a normal day. But back home the post had some interesting items, Jane was reluctant to show me until later on. When we got back that evening we studied the parcel, it was adhesive for the boobs, and as usual for Jane they had to be tried straight away. So went to change out of work clothes, a new pleasure for me, and following the instructions stuck the breasts over mine. Then got dressed, except Jane wanted a good look, and I had to take my bra off as they hung free, they felt secure and with general poking it was decided they would not come off. So I went braless for the evening, which was not terribly comfortable, but did look good according to Jane.
Thursday
With the breasts still stuck on we went to work, I was tired because the new sensation of breasts in bed had woken me a few times. As Jane opened up she discovered that this was to be the day of the visit. Everybody went mad cleaning and tidying. Then when the executives arrived just before lunch everything was in top condition, with all of us busy at work. They looked through some files, and checked on procedures for what seemed ages. At lunch they invited Jane to a small restaurant for discussions in private. Two hours later they reappeared, talked to several of the staff.
I was then hit by a bombshell, a suit came over and apologised, the records had Lesley down as a man, he was struggling to know why this had not been spotted before, but he had access to staff files and had already corrected it, I did not know how I had not given the game away, laughed or blushed, as he left he commented how lucky I was that I had not received a mans suit, the suppliers had made a few mistakes with the orders, at least two blokes had been sent women's suits. One or two of my colleagues at least were struggling to keep a straight face I know, the office erupting when they left and shut the door.
Jane then worked furiously at her terminal till the end of work. We drove home very seriously, Jane eventually blurting out that this was not meant to happen, she had no access to the personal files, so could not make any changes, which left the embarrassing situation that I was now a Ms on the records. She kept on apologising and offering to carry the can for the confusion. We cooked dinner and ate in silence. Later I went to my room, changed into the top and skirt and went out for a walk on my own. After wandering around for a while I went into a pub and bought a drink. Drank it slowly watching peoples response if any, then I went into a late shop and bought a loaf, not that we needed a loaf but I just wanted to shop alone. Next I went into an off license and bought bottles of gin and tonic. Nothing had happened, I was undoubtedly excited but did not feel highly visible. I returned to Jane's who was worried at me going off alone. Then I announced a solution to the dilemma, I could stay as a Ms, I had no objections, and it would save her face. She was totally shocked by this; the relief of my return in one piece, followed by such a statement really surprised her. She asked for time to take it in, so I went to make a drink for us both. We then sat and drank several gins, while discussing the future. Jane had to make sure it was fine with the staff, then I would have to sort out my living arrangements, such as let my house go. Jane invited me to move in permanently. I needed to spend a lot on clothes; make up and accessories, but there seemed to be no hurdle we could not overcome.
Friday
Jane went in while I stayed outside in the car. If she returned with the clothes she had taken off me the week before and gave them to me, I would have to work as a bloke. If she came out and put the bag in bin, then I was accepted. It was a long wait my mind swinging between the possibilities, eventually all the office appeared without Jane, they were carrying the bag so I thought this was the end, but in a very dramatic way they produced a metal bin, and one by one emptied the bag into it, then tipped lighter fuel on them, followed by a match. I sat in the car transfixed, Alison was the first to open the door, one by one they hugged me, apparently I was a nicer person in a skirt, and they had no problem with the new arrangement. Alison did point out I had to buy my own clothes from now on, but she did not want the ones I already had back.
Saturday
I went shopping with Jane, dresses, tops, skirts, shoes, trousers, make up, a coat, and lots of underwear. We spent the late afternoon trying on, as I would not go in a changing room. It was a special day even if about half would need to be changed.
In the evening I went out with the single girls, Jill and Beci, we had a great time in the clubs, they even offered to take me to a gay pub if I fancied a man, I felt sure I was straight, well straightish, Beci stunned me with ' you and Jane will make a good pair, she doesn't fancy blokes either' I had never known. The thought went around my mind until I left early. Jane was still up as I had hoped. Not sure how to brooch the subject I made up a tale about a man approaching me, and how I did not like it, ' am I odd I want to look like a woman, but fancy women not men,'
Jane hardly looked up ' no your not odd, I am a woman and I don't fancy men'
I had to know ' and how's about someone like me?'
Jane looked up and straight in my eyes, 'that's different'
I blushed not knowing what to expect.
She continued ' you've always been feminine to me, but still a bloke, now you are a very attractive person, and I for one am pleased you fancy women' all I could manage was an oh.
She took my hand ' do not take offence, but yes you do attract me, but I am happy just as friends.' I could feel myself hardening and straining against the tape, 'is this a platonic attraction or something else?' ' I'm happy with platonic if you are' she replied. I then asked her what she found sexy; ' affection, a good figure, a smile and underwear' was a briefened reply.
I was mildly drunk I think and smiled, ' have I a good figure?'
'Yes'
I stood up and took off the blouse and skirt to reveal the brief briefs and the shiny bra, 'not the sexiest I think, what's your opinion?'
' True you have sexier, but still good'
I went to pour her a drink. I heard her get up and then felt a light touch on my waist, 'you forgot about affection'
'no I didn't I was just thinking how to ask'
' well you need to touch a little more, but so far, fine. Does that answer your questions?'
'All except one'
'oh?'
' Yes can I have a kiss?'
That is cruising as on a ship not on the look out for a woman of the night. Shame on you if you thought such things. :)
Rob and Paul had been friends for many years, they had been to college together, had at one time worked together, but mostly they just spent time with each other, going to a match, going to the gym, spending a weekend walking in the hills. Just fairly ordinary pursuits, for a couple of blokes. They also went on holiday together, this was usually an activity holiday, skiing, sailing, surfing, cycling, whatever took there fancy and they had not done before.
Unfortunately earlier this year Rob pulled a muscle really badly, it left him unable to do much for a few months, but he was getting better when the holiday planning was being discussed. Still not sure if he would be up to doing much because his fitness would be down they looked at more passive holiday destinations. After many brochures and much discounting places many people find popular, they both agreed on a cruise. They would get to see plenty of places, the ship had a gym and plenty of activities that Paul could do, as well as easier sessions Rob could do to get back in shape.
So it was decided, 2 weeks on a luxury liner going up the Norwegian fjords, not everyone's favourite but it would be different
A month later they are stepping onto their floating hotel and eager to see the majestic mountains of Norway. It was all going quite well, nice welcome, easy going staff that showed them to their cabin. Then it hit a problem, they expected a twin and thought they had booked one, but this was a big double and not matter how much they asked it seemed that is what was on the booking, and there were no twin or single cabins unoccupied. So it was leave or stick with the double cabin. They could see it was an enormous bed and both felt it should be easy to keep out of each other's way. So they stayed and unpacked.
As they relaxed, they read the itinerary and lists of facilities, there were a few things definitely on the list of to dos for them, the gym, going ashore at the more northern ports, hopefully whale watching, and visiting the many bars and restaurants around the ship. There were also functions that the staff organised; cabaret nights, dances, and speciality food tasting were among the entertainment on offer. But for the first evening they would just relax have a nice meal and watch a film. Then see what was going on the next day.
The policy on the ship was for people to get to know one another, so tables were never small, always at least 10 placing, so when you ate you usually struck up a conversation with the fellow travellers, which was fine and added to the holiday as you made new friends. The first two days were what you would expect, but on the second evening Rob and Paul got into a conversation with a very charming couple, and as they got drunk talked about allsorts of topics until Holly said she fancied the costume evening in the ballroom the following night. Rob and Paul had only done basic drama at school so it was all new to them, which made it appealing, besides the enthusiasm Holly put into it, which made it a definite.
Next morning with sore heads they dragged themselves out for some breakfast, and met a bubbly Holly, how she could be so awake baffled them but she got them organised to visit the costume wardrobe and select outfits for that evening. So late in the afternoon Rob found himself with nothing to do and went to see what was available. He was quite surprised to find out the event was so popular and the choice was limited, but they took his size and found him a teddy boy outfit, which if he slicked his hair back could look OK. He went back to find Paul having a shower after he had been in the gym. Explained that he ought to get to the wardrobe before he had no options.
Half an hour later they are standing at the counter trying to persuade the attendant that there must be some costume like a rocker or teddy boy in his size, he was just to small and all the small outfits were out. Paul was ready to accept defeat and go as himself, when Holly came in to exchange her shoes. She was not for defeat, she would find something for Paul, 'Just you wait here'.
Paul did not wait; he knew there was nothing, so went to the bar for a drink. Rob found him later to explain how Holly had found something to go with his teddy boy things and she was having it left in their cabin as soon as there was someone available. Paul perked up at this news; he did not want to be the odd one out, that was until he got to his cabin, in a bag was 'his' outfit. He could not believe it, was it a mistake or was it Holly's joke. There was a fifties rocker chick dress; 'no way' was his limited verbal response. Rob thought it might be fun, but Holly expecting a less than keen reception went round to add her opinions. He had to do it according to her because, there was nothing else, it matched Rob, he would be the odd one out, and last night he had said how keen he was to try something new and this was certainly new. Paul was about to say but, when she continued, it did not matter if he looked like a drag queen, it was a costume party anyway, and as he probably knew nothing about make up etc, she had just been and made an appointment at the salon for him. 'All sorted' she pronounced and arranged to pick him up at six.
Paul looked at Rob as though he needed some support, the whole thing would be fine, Holly had taken over and dominated the events, but it would be OK for him to go as a girl. Rob said it would be different for sure, and after a few drinks who will care. 'Besides its ages since I took a girl to a dance' he added with a smile.
As planned Holly called round, picked up a subdued Paul and his outfit taking them through the corridors to the salon. Several women were being attended to, obviously for their costumes, and no one batted an eye when Paul was taken to a chair and asked what his costume was. He pointed to the clothes bag; Julie his stylist went over for a look and found out why he was so quiet about it. 'That is lovely, now what do you want me to do, time is limited but I shall see what I can do'. 'Whatever you think I will need, I really have no idea'.
A clueless Paul was taken to a small room where Julie helped him change and familiarise him with the new clothes. Holly had thought of everything, there were control knickers, false breasts to provide the shape, then stockings for his legs. Julie stopped there and gave Paul a towel wrap and led him back to the salon chair. ' So how you look is up to me?' Julie asked, 'Just don't let me look ridiculous, I just want to blend in really' is how Paul expressed his concern. ' So we make you look as girlie as possible, no drag or clown styles' Paul agreed to this and tried to relax as she set about his face and hair. He was really not aware of what she was doing, she pulled a few hairs from his eyebrows, then using several bottles applied make up to his face, he watched in the mirror as his features altered, cheek bones became more pronounced, the eyes seemed bigger, his lips more prominent. He had longish hair for a man, but Julie wanted him to have long auburn hair, so a wig was the only choice. Then it was back to the changing room to put on the netting underskirt, with the pastel blue disc skirt over it, followed by a fitted sleeveless top that buttoned up the back and a matching cream cardigan to finish off. 'I guess you have never worn heels before' she asked Paul, as she pulled out a pair of sling backs, he had never but said he would have to give it a try and learn. So while he was pacing around the room and adjusting the strap to stop them slipping off, Julie went back to the salon and came back with what she called the finishing touches, a couple of rings, a bracelet, some clip on ear rings, and a spray of scent. 'Now I can do your nails, if we are quick' this was all just overwhelming Paul, who just agreed to anything, and as he sat down at the nail station caught a glimpse of himself in a mirror, it was him the body movements, the stance was his but the look was not, at a glance he was a woman. By the time Julie had finished the first coat of the candy pink polish, he asked what she thought of how it had come out. She would obviously say terrific, but did add that she can change the static image, it was up to him to change his demeanour to a more feminine one, otherwise he will just look like a well-dressed bloke in a dress. And as she did the second coat gave him tips on walking with shorter steps and the feet more in line, the shoulders relaxed and arms in, less of the macho stride. As she dried the nails she asked how he felt now he was finished, 'Rather odd, everything feels nice, but different, but I now have to go out and be seen by people who will judge what they see, and possibly laugh at me' Julie took his hand lent over and gave him a cheek kiss and quietly told no one will laugh, especially if he acts like the girl he looks like. After a pause 'Now do I call your friends, or are you going off on your own?' Paul looked at the time, the ballroom would be open by now, so he called Rob and asked him to call round and pick him up.
Rob was stunned when he walked into the salon, at first he could not see his friend but as a woman started to walk towards him, his mouth dropped as he realised his friend was now looking like a 50s woman. Julie stepped up to him, 'That is no way to say hello to a young woman, shut your mouth, take your eyes of her body and treat her well' Paul spoke first 'Well do you like it? Will it be ok for this costume party?' 'Yes and definitely yes, you are stunning, and to think somewhere in there is Paul, fantastic. So what do I call you, Paul seems odd now?' 'Paula, Paulette, Pauline, P or something else' chipped in Julie, 'I had a crush on a Fiona once so how about that?' all three settled on Fiona as being right, then Julie pushed them out the door and told them to enjoy themselves.
Paul now Fiona started to get into the character of his image, he thought about this posture, and walked making the skirt sway and his tits bounce slightly, then he thought about what a woman would do when walking with a partner and linked her arm in his. Rob jumped a little, 'Just getting into character' Fiona reassured Rob, and he relaxed and let the arm stay as they walked, 'Getting into character. Let's be clear, you are going to pretend to be girl, and so I guess you want me to treat you as one.' 'Exactly, I don't look like a drag queen, I look like a woman and I do not wish to stand out, so the best way is to behave like one. Are you fine with that?' 'You want me to treat you as a Fiona not a Paul. Right? I shall try' ' You see a woman, treat me the way you would treat one on a date, how does that sound' 'OK Fiona I shall do my best'
They entered the ballroom, found a table, then Rob went to the bar and got some drinks, a pint for himself but not knowing how Fiona would react to a beer, he decided a 50s girl would drink cocktails and ordered a screwdriver. The fancy drink made Fiona smile as she thanked him and took a sip through the straw. They busied themselves watching others turning up in costumes from history and films, they hardly recognised anyone, so when Holly and her mate sat by them they were not ready for her. Having Alice and the mad hatter surprise you with 'You are beautiful' and then both kiss you, did take some beating on a shock scale.
The evening went by very amiably, Fiona tried a few more cocktails with Holly, slowly being more and more relaxed, as they could drink two for every pint the men had. Fiona was persuaded to dance by Holly who was able to give her a quick course on using the skirt to make the moves better, and how to use the ladies, which was a new environment for Fiona who really only needed a urinal. After several dances with Holly and chats with other guests and cocktails, the DJ put on the slower smoochier tunes. Holly had the mad hatter up and shuffled him around the floor, Rob had lost his reserve enough, so when they were prompted to have a dance, Rob took Fiona's hand and lead her out to the dancefloor, he had been doing his best to treat Fiona as the girl that he was seeing, so when he danced he held her like he would any other woman. Close, and for three tunes they drifted around the floor. Fiona could feel his hands also drifting down her back till they were on her hips and butt as he slowly pushed his hips toward her, she at times would drape herself off his shoulders, or grip his arse reflecting his grip. The bigger shock was to find herself resting her head on his shoulder feeling him kiss her ear and then responding by kissing his neck, and feeling the cuddle get tighter as a consequence. It was a shock but it felt right, and with the alcohol it was easy to get into the mood. The music ended, still holding hands they had their last drinks, were saying their good night when Holly reappeared with a small bag and gave it to Fiona, telling her to open it when they got back to their cabin. So arm in arm Fiona and Rob wandered back to their bed.
Once behind a closed door Fiona told Rob how much she had enjoyed the evening, and gave him what she thought would a last kiss, but he responded by kissing back. After a few minutes she asked him if he would undo the buttons down the back of the blouse, then as she lowered the skirt and he got a full view of the suspenders, he stood back took a long look and declared her even better, then baser instincts took over as Rob hugged her again and Fiona started undressing him, to dixcover he was getting very excited. After a while they found themselves on the bed caressing each other's body, Fiona massaging his penis so it stayed stiff. Neither knew what should happen beyond cuddling, but when Fiona asked what he wanted her to do for his relief, he rolled on top and started to rub his erection on her stomach, she felt his little dribbles, and in the heat of the moment rolled him on to his back and proceeded to kiss then suck his dick, all he could do was hold her head and cum. Spent they lay together, 'so what is in the bag?' Rob asked, ' a nightie' Fiona replied 'do you think I should wear it?' 'Why not, let's see if you look any more sexy?' it was a short silk one with spaghetti straps. 'Does my boyfriend approve?' 'This one certainly does, come back to bed.....Fiona'
It was hard to sleep and after some more cuddling she once again found herself sucking him till he came. Then exhausted he fell asleep, leaving her still wanting something but not sure what, but eventually calming down and dropping off.
As morning arrived Rob found himself lying next to an attractive woman where his friend Paul should have been, as everything came into focus, and his memory returned, the pleasures of the night before both confused and delighted him. He could not look at the long haired woman wearing the sexiest things he had ever seen in a morning and think of it as anything other than Fiona, though deep down he knew it was Paul. They had done things Rob and Paul would never have done, he did not consider either of them gay, but it had been good. Would this end the friendship? Would they ever speak again? Had their bond been broken?
Rob made his exit quietly, and had breakfast alone, he returned not knowing how things would be when his friend woke, he just knew he was nervous about losing his best friend over a night of stupid behaviour.
Paul woke to find hair in his face, dressed in unfamiliar clothes and alone. He too went through a muzzy waking then a realisation of how he had ended up in bed wearing some very luxurious clothes, and feeling good about it. But also the memory that he had had oral sex with his friend left a worrying fear hanging over all the good and fun memories.
As he lay there gathering his thoughts, Rob who had had enough coffee for one day already, returned. His confusion was not helped to find Paul awake and still looking like Fiona, her hair had been finger combed off her face, and the make up smudged but still the feminine face was there. Suddenly aware he would have to do something Paul sat up, trying not to show Rob the sexy clothes, and made a move to get up saying 'I had better get changed and out of these things, hadn't I?' Rob wanted to say no, ' but instead said 'if you must'
'Pardon'
'Well only if you want to'
'Meaning what'
'I don't know really'
'Please help me here, what we did; I don't know what happens now. I mean I'm sorry, I should never have let Holly talk me into it'
Rob was starting to blush at the memory of the night before. 'No it was good, I had a fun time with the dressing up, and you did look really good.'
'Did I really, I suppose I must, no one called me Paul and was constantly called she or her. But the later stuff, that should not have happened, we are mates. You know what I mean'
'I do, maybe it shouldn't but it did. How did you feel doing it, you seemed to be enjoying yourself at the time'
'Well you certainly were, it just felt that was what I wanted to do, I have never felt like that before'
'This is not helping, you still look like Fiona, and I am confused about how I feel and what we did. Part of me really liked it another is telling me you're my mate Paul and well we are mates, you know what I mean I hope'
'Your confused, think how I feel, I was the one pretending to be your girlfriend, and worried I had taken the pretence to far'
'Should we just put it down as an experience then'
'Well I do need to wash and so on, which take away the illusion I expect, especially if I can find out how the wig is fixed on'
'I shall go and get you some breakfast,' then added for effect 'If you would like sweetheart'
Paul turned and smiled at his friend, wondering what was going through his mind, had he enjoyed it, was he really as confused as himself about being gay and the clothes etc. maybe best just let it lie and things will return to normal.
As he cleaned up and Paul reappeared, he could not get the nail polish off, soap did everything else, but this would not shift. After he ate the rolls that Rob had fetched, Rob asked about the pink nails, was he keeping them. 'Do you want me too?' Paul asked then added 'Let's not do that conversation again. I can't get it off, I guess I need a remover of some sort, I shall have to ask Holly for some' Rob wanting to help went to find Holly and some remover.
They seemed to be ages, but eventually Rob returned with Holly and a bottle. Rob then picked up some gym kit and left, which made Paul give them a quizzical look. 'Let's see your nails then' and she lifted his hands in hers 'they look good, why clean it off?' Paul blushed 'Please we just had an awkward conversation, probably best I stick with being Paul from now on'
Holly then slowly cleaned the polish off, but as she did got him talking about how he had felt about being Fiona. He concluded saying he was confused, she concluded that he had enjoyed it, and from her chat with Rob on the way there, that he too had enjoyed his 'girlfriend'.
They spent the day hardly speaking, not sure what should happen next. Holly meet them for the evening meal and suggested that the next day they would stopping at Bergen and would Paul like to go with her, her Jack never fancied the town so was going to take a ride up the valley side, Rob thought Jack's idea sounded good as well.
So after a difficult night sleeping in the same bed, they berthed and went their separate ways. Holly had a plan to get Paul looking around dress shops to test out her idea that he would be Fiona again. Their poor Norwegian did not help, but her undeniable enthusiasm got Paul first looking at women's clothes, then holding them up and giving opinions. Holly would purchase only the ones he liked, and soon had a sheer loose blouse, a full-layered skirt, and a pair of heeled boots and packs of underwear. Paul had innocently gone along with this, until she asked his shoe size, as the penny dropped he steered her into a café. It did not take long for her to come clean about who the clothes were for. As this information sank in, he asked why. 'Because you both obviously had fun the other night, and I think you make a smashing Fiona, that I want to get better acquainted with.' She paused 'Nothing wrong in that I hope?' Paul thought before replying 'And what it wrecks our friendship' Holly just told him whatever happens the friendship had changed already, there was no going back, they went forward or apart. Put like that Paul reckoned he had no choice, and he wanted to keep Rob's friendship, and being Fiona again would do no more harm, but maybe add something to their bond. After what he hoped seemed like a considered silence he agreed that he would see how things went as loosing Rob was not on his list of things to do.
Once back on board they got themselves organised, an appointment with Julie to have a proper session and some more tips, but that would be after Holly had explained the products they had bought from the ladies section in a supermarket. Paul first had to immac his legs and arms, then shave his more delicate bits. The moisturiser after was nice and soothing, but the realisation of what he was doing as he walked into Julie's salon made him go quiet. Everything had already been discussed beforehand with Holly's prompting, but now he was on his own. He recalled their conversations, and the times with Rob, and when Julie asked if it was fine to start, he smiled at the thought of being Fiona again and how Rob might react.
She thinned his eyebrows, then applied make up giving him tips on how to do it himself, next the hair, he wanted something that would not come off, so she wove a straight blonde wig into his own hair, which meant he could go out in a strong wind and not fear he lost it. Next he had extensions added to his fingernails, and painted a ruby colour along with his toes. He thought they had covered all the items discussed, when Julie meet him in her changing room with breast forms that she carefully placed into his white lacy bra, they felt cold to his skin, but as she held them to him they warmed. Then with a cheeky grin she said, 'I hope you like them, as you have little choice now' as she let go the skin pulled on his chest, 'Glued?' 'Yes, enjoy them, now lets get your maleness hidden.' He lay on a bed as she taped his penis between his legs. 'Now you don't need the control pants, you can use the nice lace pants, but you must sit to pee, but then the ladies don't have urinals do they' this was all going a bit further than discussed, but with the matching knickers and bra on he did look good.
He managed to get into the stockings, and then the blouse and skirt without much trouble even with the longer nails making things more awkward. Last he zipped up the boots and looked at the finished effect. He was not sure about having his bra faintly visible through the blouse, nor about the fuck me boots he was wearing. But he had made the choice earlier, now was not the time to bottle out.
As arranged he would meet Holly at 7 in the bar. Rob had no idea what had been happening through the day, so when he found his cabin empty, after having a rest he wandered down to the bars to see if Holly was around. He found Holly talking to a woman he did not recognise from behind, but as soon as he asked Holly if she knew where Paul was he immediately saw it was Fiona. Fiona stood up and kissed his cheek and gave him a hug, 'well are you pleased to see me then?' she asked 'of course, but after yesterday, well maybe another time you can tell me about it'
Fiona relaxed after Rob's warm reaction, and they spent the evening eating, drinking and chatting with other guests. Rob kept an eye out for peoples response to Fiona, he would go to the bar and linger watching her and the other people around, expecting to see people pointing and staring, but it all went really well. Fiona was seen as female, which would make life easier for them if Fiona decided to stay a while.
It was not late when they felt it was time to go to their cabin. The big bed was not a problem now, but not being drunk might be. The affection they had shown in the bar was limited to sitting close and holding hands, but once behind closed doors. Rob just said 'God you are sexy' then picked her up and kissed her long and hard. Eventually Fiona broke and said she should undress, so with Rob watching, she removed her outer clothes, then her underwear, Rob was shocked to see there was only a pubic triangle between the legs, and that the tits stayed on the chest. Fiona then slipped the nightie on that Holly had lent her before, and went over to a static Rob and started to undress him and lead him into bed. As before the excitement got both of them and they forgot all about not being gay, as Fiona once more sucked Rob off.
As they lay cuddled up together, Rob asked about why Fiona was back, and how long she would stay. Fiona was honest and told him as long he wanted, but she only had what she wore that evening, so it was limited. Rob had a spurt of generosity and suggested she borrow his credit card and get a few more things. Fiona was already ahead of him; she would need some warm clothes for daytime, plus some evening outfits, to which he agreed as long as Fiona stayed till the cruise was over. Their freindship changed forever as they agreed to this new situation.
Next morning was far easier to cope with, Rob looked at Fiona and lent over to kiss her, which brought a warm response from her, and soon they were at it again. But in the afterglow, Rob asked if Fiona wanted anything, as it was only he that orgasmed. Fiona agreed but had no idea what they could do, his equipment was securely tucked away, and though it wanted to come in its tight confines there was nothing for it to do. So the subject was dropped.
Holly wanted to know how they ha got on, had her conclusions been right? They told her as much as they thought she needed to know, but Fiona dressed in a Paul jumper and jeans, with the boots and make up wanted to know when she could go shopping. Holly said that first stop was her cabin. Where she found a tight roll neck top and some tight jeans that tucked into the top of her boots. 'Right from now on I don't want to see you hiding your sex appeal, I think from now on you should dress so Rob knows exactly what you are. One sexy woman! Right.' Fiona was looking in a mirror 'right' 'No baggy tops, I want to see tits and legs, or at the least, feminine so Rob has no option but to get a hard on. Right.' 'Are you sure? I mean Rob is not daft he knows what I am' 'Dead sure, he will see you and melt; you already got his credit card. So I want to see him stiff all day' she laughed at that one, and Fiona joined in at the thought, then smiled at the idea that she could do that, then thinking she wanted to, then thinking what would she do with him if he was stiff so much.
They spent the day watching the fjords go past, Fiona wanted to get a warm jacket when they sat on deck, but would hear Holly's advice, remember the look is important. So with only an arm for warmth, she sat beside Rob trying not to think about how to get indoors, and get warm again.
Over the next few days Fiona added to her wardrobe, first with a warm fitted coat, then a mini skirt, but Holly pointed out a skirt does not have to be short to be sexy, so the next was a black dress which came to above the knee, but left little to the imagination, along with heeled sandals, and after a day in the boots, some low heeled courts. Even a pair of fitted hipster jeans made a welcome addition for daytime. But all the tops were either figure hugging or see through in some way; so nice underwear was always a must, as was stockings, which was Rob's preference.
After one particular busy shopping day in a town, they had both spent time looking at different things, Rob had bought her a basque that he thought might be nice. But Fiona was getting quite pent up with not climaxing, she still enjoyed and wanted to suck Rob as often as he could stand it, but she did want something back. Rob was thinking along the same lines, he felt he want to see her climax in some way, but did not fancy sucking her even if he could get past the tape, somehow it would ruin the illusion.
So with neither knowing, they both found a chemist and bought KY jelly, knowing that it should help with lubrication.
That evening dressed in her basque and stockings, with just a sheer blouse and loose soft skirt covering her stocking tops, she hoped to try some new moves. After a nice meal and several drinks, they retired to their cabin. Fiona made her way to the toilet after he had removed her blouse and skirt. He was as ready as he would ever be she thought, in the toilet she squeezed some jelly into her arse, then returned to see how it would work out. To her surprise he was underdressed on the bed with an obvious tube of KY. She picked it up 'snap' kissed him 'but mine is already waiting for you, all we need to do is find out how you fuck me' 'agreed' said Rob as he pulled her onto him. He would not let her massage him, rather he concentrated on her hole, finding that she liked being massaged just in front, then he slowly pushed his stiff penis into her arse. It was all he could do not to push hard and satisfy himself. But soon he was inside riding in and out to her heavier breathing, until he lost it and just got too excited and came inside her.
He tried to carry on but he had no chance, and then started to apologise. She said how nice it had been, helping his ego, and wanted to try other positions. And so after another drink, she was massaging his dick back to life, as he massaged jelly into her hole. She then went to lay over the back of a chair so he knew what he was supposed to do, as the arse was presented to him so obviously. Without instruction he entered her and sensing her pleasure moved around finding out if there was a g spot. He knew he hit when she tried to pull him closer, so he pulled her hips into his and pushed, he managed to hold out until she let out a moan of delight, which was all he needed to push his weakening hold on his restraint and come again.
As they uncoupled, Fiona turned and wanted to do it again, she could not chance forgetting how she had come. But Rob was exhausted and could only cuddle her to sleep, knowing they had lost their virginity in a big way that evening.
After their exertions they made it for breakfast about lunchtime, which got Holly interested, and after some fishing found out about their lovemaking. Which got Holly excited and could not wait for Jack to finish before whisking him off to their cabin to satisfy her own passions. Which left Rob and Fiona alone. Fiona had to see Julie to get her hair conditioned, which left Rob time for the gym and sightseeing.
Julie was interested in how things were working out, and judging for the sexy outfit she turned up in, Julie did not need much help knowing what Fiona was getting. Once the hair was drying Julie spent some time showing Fiona a few different things to do with make up, especially how to make the eyes bigger and the lips more lush. So much better did Fiona feel, she went straight to the cabin to wait for Rob, hoping the new look would not go unnoticed. And so continued their exploration into how to climax Fiona.
By the end of their second week, they realised how little of the fjords they had seen, but how much of their bed, and how much they had learnt about sexual pleasure instead. On the last day Fiona only wore a bra for support, a dress and some shoes, she did not want things to hamper her last day with Rob as Fiona, and intended making the most of it. And she did to the point of making them both so sore they could not touch each other's genitals by early evening. But they were happy. And reflected on their time as a couple for the remaining hours.
Returning home was an anticlimax, as most holidays are, but Paul went back to his normal life, dressing as a man, working as a man, living as a man. He would even go for a drink with Rob as a man, which was strange the first time, but got easier with time.
After a month they were alone and getting drunk, they started to discuss more deeply their holiday experiences, previously they had glossed over saying how good it was and yes they should go on another holiday sometime, but with a relaxing drink in them, Rob confessed to missing Fiona, not just the sex but the person of Fiona as well. So Paul then confessed to having not only kept all the clothes, but had bought some more, especially underwear, because he always wore knickers now and kept himself shaved. Rob almost shouted, 'You in knickers now, which ones?' but did it quietly.
'The red satin thong, if you must know'
'anything else?'
'Well I don't usually but today I went for the full set, camisole, suspenders and stocking.......... Would you mind not putting your hand on my leg in public, please'
'Just checking, I can feel the clips, you are aren't you'
'Would I lie to you?'
Rob was getting excited, but stayed calm, 'Have you dressed since?'
'Only fully once, I wanted to see if I could do it, but I did not go out'
'What do you mean only fully once?'
'Well like tonight, I am just in undies, not fully made up and everything'
'Anything else?'
'Well I do sleep in a nightie now'
'And I just sleep alone. You are still girlie underneath aren't you?'
'Yes I have changed, I like the idea of being feminine, and I have to have something that makes me feel feminine.'
'Could you be a bit more girlie for me tonight?'
'What do you mean, a bit more girlie?'
'Well would you be Fiona for me?'
'I would need some time to prepare, but if you could call in about an hour, I guess Fiona could see you'
Rob could not believe what they had just arranged, he had missed Fiona, but had never thought an opportunity like this would happen. Now he had to think what to do for an hour.
Paul left as quickly as possible, not taking long to get back to his flat, all the time thinking what he should wear. Just a revealing nightie and drag him into bed, or was it too early, dress and go out somewhere. He had the choice and could once again get Rob to do whatever he wanted, which felt oddly nice. It did not take long to decide, he had bought a lovely long swirling skirt and a bell sleeved top to match it, with the boots and make up he would soon be walking around their home town as he never had before.
Sat on top of a bar stool sipping another cocktail Fiona felt wonderful, she could feel Rob's hand resting on hers and wishing she had had the time to do her nails, but you can't have everything when in a rush. Rob wanted to know more about his friend's new life, 'So what else should I know?'
'Well I have had my ears pierced, do you like them?' Fiona made a show of pulling her hair back, 'I am not going to the barbers again, Julie has shown me how much better a salon is. Just little things I know'
'But the little things add up, where is this going to take you?'
'Not sure I just enjoy the clothes at the moment, and of course you' which was followed by a long kiss, and discreet fondling.
They made their way back to Fiona's flat, barely before the door had shut Rob was wanting to have some relief, seeing how she had kept him erect for nearly three hours and was feeling eager herself. It was up with the skirt and down with his zip, and straight to it. She only had a firm thong on, so access was easy and soon they were lay on the floor spent and thinking about the coffee they had come back for.
They spent that night and next day together, just enjoying each others company, and for Fiona enjoying being able to be as girlie as she wanted with the man that she wanted. The day was lovely, they were old friends just chilling out walking in the country, but at the same time a couple getting to know each other, quite unusual but it worked.
Monday came too soon, and it was back to work. Rob back to his usual routine, Paul more or less back to being Paul except for the hidden clothes that he wore for his own comfort.
Over the next weeks they slowly slipped into a comfortable pattern, through the week they were mates and meet for gym or running in the evening, but at weekend unless there was an event Paul wanted to participate in, then Fiona came out for a couple of days. They would go out as a couple in the evenings, but daytime could mean going to watch Rob compete, or going shopping, even just stop in and clean up. But whatever happened it was done as Fiona. Eventually Paul never wanted to do anything at the weekends that was not done as Fiona. Which suited Rob as he could have his friend along to support him, and then have some fun with her at night, which actually suited Fiona as well who was gradually building up a wardrobe that did not just include sexy stuff, but warm jumpers and trousers to wear on the windswept fells when Rob was out racing on the hills, or just walking together, making Fiona feel somehow closer to being a real girlfriend than just a sexual partner.
Marriages break down for all sorts of reasons. Micheal and Sandra are doubtful for counselling and reconciliation
Dear Michael
I do hope you are able to read this letter before you hear someone knocking on the door, it will help you understand why you are in a strange room lying face down with your ankles locked with handcuffs to the bed and a gag in your mouth.
Let me try to explain how you come to be in this position. You might have noticed I have been rather cold towards you recently and taken to sleeping in the spare bed, well about two months ago while searching for something in the loft I came across a rather well hidden box of women's clothes plus wig, fake breasts and a good selection of make up and jewellery. At first I was confused and assumed it was something a previous owner had left, but then I spotted some websites in the search history on the computer that I did not recognise and when I looked at them was shocked by them. It had to be you and I made the connection as I looked at them, between the clothes and the websites, that you have a liking to dress as a woman. I took another look in the loft and tried to understand what the clothes were for. I am guessing the maid outfit was for when you proudly told me you had been cleaning on your days alone at home, the smart suit, sundress, cocktail dress are all very nice but when would you wear them? and I dare not think why you had the clothes you are currently wearing, the red leather mini, red corset, sheer red blouse, stockings and ridiculously high heels. Though I am guessing they are appropriate for your current situation.
Anyway I put together the clothes and the story content of the websites and decided that I was sickened by all this stuff, you are a pervert and some of those things described make me ill. I do now understand certain incidents such as when you encouraged me to wear your boxers to bed while you borrowed my nightie. It also explains those bizarre conversations about you wanting me to tie you up. I now also relate to why you bought that vibrator shaped like a penis, at the time I could think of no use for it, but as you are probably aware it is pushed into your anus as you read this, so it has not been wasted, I don't know whether you have used it before, but it seemed to go in easily and even drugged you smiled.
I did consider just walking out on you but felt that would be too easy on you, so I hatched a plan to use the fantasies to embarrass, humiliate, hurt and hopefully bring you so low you will be ashamed of yourself. Let me explain what I have done.
As from now on you areMiss Michelle Jones, the flat you are in is paid for in that name, the utilities are also, the only clothes you have are the ones hung up in the room around you (your male clothes at 'my' home will be disposed of when I get back). I am surprised how easy it is to create a new identity with a false driving license, please note that the DOB on the license is ten years younger than you really are, as a girl I thought you would appreciate that. This means that you will have to go out at sometime dressed as a woman, if only to find some way of regaining your male identity, and somehow explain why you look like you do if you are not a convincing imitation of a woman. All the accounts are set up as cash so you will need to go in and pay for them personally, they are expecting a woman. I did think of many more things I could have done to you but time prevented me, hair extensions, colouring, restyling, false nails, tattooing and piercings all were on the list, but you will have be satisfied with adhesive for your fake chest which should last a few weeks, painted nails and and some very secure locking clips Sally at the salon assures me are good for a few days, by which time you will have to remove it as your own hair will be in need of a good clean. Fortunately I did get you to depilate with Immac, and I do hope you like the thin eye brows, I do hope they will make for a odd looking man if you try to be Michael.
You are currently in a hopefully very compromising position, and the knock on the door I mentioned earlier will increase your situation. After a quick look through some of those stories it seems you like the idea of being a woman and a man having sex with you, I am not so sure how much you like the bondage but for my purposes now it helps. I reckon by now you will have found the padlocks on your ankles and on the gag. In the last few weeks I have created online adverts for you. 'Michelle, 26, TV, would like to have fun with men' I admit to being quite shocked at the number of responses they received. That is only my opinion what matters to you now is that four of these men who replied have been sent copies of the keys that will unlock your restraints, they know that they should knock once and that the door is unlocked, and that you are waiting for them to do whatever their perverted minds think you might be waiting for. I thought to invite more than one as I did want to risk no one turning up and who knows you might actually fantasize about more than one man. I can honestly say you are not the man I once knew, in more ways than one.
I do hope you appreciated all I have done for you, the seedy places I have been to obtain the fake documents, the rohipnol to make you compliant (sorry if I got the dose wrong, I am new to this), and the living with a man I find has disgusting secrets that repulse me, have all been very hard for me.
On my way home I shall be calling at the solicitors to make arrangements for our divorce, I expect you to give me the house and not argue over the custody of the cats.
Yours sincerely, but definitely not faithfully now.
Mrs Sandra Jones, (soon to be Ms Sandra Keane, I never did like your surname)
To Ms S Keane
Apologies for not replying sooner, I was rather tied up when I read your last letter.
I am writing to thank you for the wonderful thing you did for me three weeks ago, I do not know how much you have worked out about my other more feminine side, but your actions did rather drop me in at the deep end as it were. Luckily I had enough idea of how to cope and did not get overwhelmed by the situation and drown, I did rather well out of the experience actually.
As you suspected not all the men turned up, three did, Tony, Andy and Dave, but you knew their names already. I had indeed read your letter before Tony appeared so was alert to the situation and not shocked by my dress nor my restraints, bondage is not something I would go for ordinarily but I can see the benefits in the situation you prepared, and it did give me chance to enjoy the sensations of a vibrator stimulating my love spot. As instructed Tony came with condoms and lubricant which was considerate of you to insist on. He is what you would call the strong silent type, without a word he came in removed the vibrator and used me for his pleasure. I do not know how long you staggered their arrival times by, but as Tony was getting ready to leave the second knock heralded Andy's arrival, they both seemed a little surprised to see another man visiting me, and while Andy was enjoying my situation, Tony was in the kitchen making a drink (thanks for the coffee and milk). When Andy was finished I assume he went and had a coffee with Tony because I could hear them talking. Dave must have been number four as there was quite a delay before he arrived, he was much gentler and released me before making love to me. I was then invited to join them, made them all another drink and listened as they discussed my current issues. Andy had picked up your letter so they all knew why I was there and why they had been invited, they also made suggestions as to what I might do in the future, ranging from getting me back to Michael and some sort of revenge on you, to embracing my new name and living as Michelle. This was the most practical short term solution, though I think well all wanted to see if Michelle could be a long term prospect.
Tony is a manager of some sort who is in town for a few nights each week and offered to give me the equivalent money to his hotel costs if I looked after him when he is around. Andy has a business which finds work for home workers, last week I packed 5,000 electronic bits in packets which is about as dull as the call centre job I had. Dave is not like the other two in that they are definitely men, Dave is more confused and though he does not want to be a woman seems to treat me as though we are girlfriends, lesbian friends that is. He seems to know lots of people and has connections with a salon chain and has been kind enough to arrange for a more complete female image to be seen in my appearance, though I must congratulate you on how good I looked when you left me that day, they all complimented me on how pretty I was and that I should have little trouble living as a woman. I these three weeks I have had each ear pierced twice, I have a nose stud and a stud in my tongue. My navel has a ring plus Michelle has been tattooed in a flower pattern around it. I have had a spray tan which is now looking nice as it is fading. The long nails took some getting used to but are excellent for stimulating my men. Unfortunately I will need to use wigs for a few months until my own hair is long enough to take extensions then I know there will be much debate at to how I should have my hair as I am able to swap styles with ease to please the different tastes of the boys.
As you made clear in your letter I was not welcome back with you, and the only way I could dress for the next few days at least would be in the women's clothes you had left with me. So far I have been shopping for groceries, checked the details at the estate agents and with an advance of Andy bought myself a nice dark green pattern dress which fits like a glove and a brown jacket. I managed those trips on my own, but my boyfriends do like to take me out and most evenings I am out at least having a drink in a bar somewhere enjoying my new life style and image.
As you can tell I am so grateful to you, the red outfit is not very practical and I am favouring a couple of new dresses I have bought. My boyfriends have made a few rules though, I will not be allowed to get any shoes with less than a 3" heels or higher ( I know you would hate that), I am always to wear a dress or skirt, some comment about me not being the sort of person who wears the trousers made us all laugh, possibly because at the time I was in the french maid outfit serving them drinks while they discussed my future. The house must be kept immaculate, and I must be available for them whenever they need me for love making. They are insisting on me doing voice training, deportment and aerobics classes. Dave is talking about surgery, but I think I need time at adjust first, but who knows, my boy bits are of no use and just get in the way now, though I think they would all rather like me to have breast enhancement, can you believe they think DD would be nice.
Anyway, thank you for giving me such a good start, I do hope these details have not upset you too much. I shall not contest the divorce, no point paying out to those blood sucking legal's. I would like to have your car though, the little red sports car is far prettier than my old saloon. I would also like you to share some of the furniture when I get a new place, and enough cash to get myself started on my new life, remembering you will be getting a very nice house. I see this as being very much in your favour. If you do not like this, Dave knows some lawyer who would have a great time prosecuting you for the terrible things you did to me without consent, such as drugging me, altering my appearance, false imprisonment, acting as my pimp. I do also wonder if the fact you encouraged the men to have sex without my consent which would make you accessory to rape. Just a few things that I hope will help you be generous towards my future needs for some money.
All the best
Ms Michelle Jones
Many people use Ebay hoping to get something cheap or difficult to find locally, some use it to make a profit. But not many use it to find an alternative life style and new partner, even if it is unwittingly.
There was a time when I had inhibitions, but they were long gone, along with my marriage and any real sense of worth. I shared a rented house with an old friend and just existed. I worked, slept and ate, with the usual weekend evening spent drinking and being rowdy, which had lead to me being reckless and doing far too many things that a sensible man should not do.
At home I mostly watched TV or read books, but Tim the housemate liked buying and selling on Ebay, he would buy allsorts of stuff that I thought was worthless and turn it into a profit, I could never see how, but he spent his free time going to sales and auctions to pick up stuff, which he then brought home and cluttered up the house with.
It was a cold November evening, Tim had been and bought another load of random stuff and was busy getting it into the house and unpacking it. He caught my attention when he let out a big laugh, I looked over to see him pulling out a deep green velvet material that at first I took for curtains, but as it emerged, I realised it was a dress. He had never done women's clothing before.
'So this was not what you was expecting?' I asked
'Certainly not, the lot was called samples, so it was just a lucky dip. Still they were cheap and look decent. They should sell'
He had bought 20 of these dresses, to me all of them looked like theatre costumes for period productions. He put them on his listings and waited, but nothing sold. A week later we were chatting about this lack of success, and to me it was obvious when he showed me the pictures. He had just hung them from a hanger they were lifeless and sagged.
'What you need is a body inside them, a model' I suggested.
He thought and agreed that it should improve the look of them. But where to find a woman to model them. This would be hard because we were now a couple of blokes women usually avoided.
'Tell you what, we both try one each, and see if they fit' was my bright idea.
Tim has a bit of a belly and broad shoulders, so the dress failed to fit in many places or even fasten. It looked better on the hanger if we were honest. Next my turn, I stripped to my underpants and stepped into the dress, it was heavy, but at the same time quite felt warm, and as my arms slipped down the sleeves and Tim pulled the laces tight at the back, it felt like a glove around my body. I breathed in so Tim could get the waist narrower and better shaped; I pulled the neck straight and lifted the long skirt to let it fall better. Then went to look in a mirror, the dress looked as good as it felt, a medieval gown, the skirt on the floor, the waist pulled in so the skirt flared out over the hips, a round neck with a beaded edge, and long sleeves that looked like a magician would hide his tricks up.
'It fits great, looks like we have a model'
Tim went for his camera and took several shots, then uploaded them.
'You know what, could I add a few little extras?'
'Like?'
He soon reappeared after routing in some boxes with a dark wig and a small coronet. Then slipped a couple of big rings onto my fingers.
'Right, let's try again now you look more the part'
I posed and the shot, and when he uploaded it we agreed it was far better. What I failed to tell him was how nice the dress felt. And while he was doing the listing I went to make a drink still in the dress, then sat and watched as he entered the details, waiting to see which shot he put up for the world to see.
The dress was nice and warm to wear, the long skirt and sleeves meant I was very comfortable sitting, it was also quite entertaining moving around, the long skirt would trip me up on stairs if I did not lift the hem up, and the sleeves that kept my hands warm as they were so long, would get in the way when drinking or just doing anything with my hands. I must have worn the dress for two hours before I felt enough and it was time to go and sleep, but as I asked Tim to undo the laces, he asked how it felt, observed how long I had worn it after the pictures had been taken. But I suppose most telling was that I had a smile on my face, something I rarely did. I tried to be honest without sounding to weird and making him think I had gone gay or something, which he seemed to accept and just reaffirmed that I did look relaxed and very good in the outfit.
It should not have been a surprise, but Tim could not help but tell me how much people were bidding for the dress, it was the party and pantomime season so it should do well, but he was convinced it was my modelling that made the difference. The inevitable happened, he had twenty of these dresses to sell and come Saturday I was required to be his model for the day.
He took it more seriously this time though, on the morning I found myself being offered a bra with breast inserts, to give me a better shape, a pair of control pants to stop any crutch bulges, a pair of tights to cover my none too hairy legs, and some lipstick and blusher to make my face more feminine for the camera.
I put all the extra clothes on, and applied the make up, but for some odd reason felt it necessary to pull a dressing gown on to cover my underwear before going to the room he was using for the photos.
First up was another medieval dress in green, then a Victorian bustle dress, and a Wild West saloon girl. We were surprised how long it was taking to change and add accessories, but we felt it was worth adding little extras so it helped make the costume look right.
We broke for lunch after we had taken pictures of a 1900s maid, and as a joke I served him his meal, and curtseyed calling him sir, asking if he would be needing me for anything else, and other such stereotypical nonsense.
The afternoon went pretty well, the only difference being we had some outfits with shorter skirts that needed proper female shoes to look right, so when we had finished the long dresses we stopped for the day. I was in what was described as a 1930s evening gown, a straight skirt with a narrow waist and wide strap shoulders. It was tight and moved around my body sensually as I walked, I could feel the cool fabric on my arse with every move, and it felt so good I was reluctant to take it off, but not before I had played at being Tim's wife for a bit as I cooked us both a meal, and laid the table with candles and a bottle of wine, then after I had redone my lipstick went to drag him from the computer so he would eat the meal with me. I called him sweetheart, and he responded by calling dear. Making up silly conversation about how I was a film star and who I had meet.
After dinner I cleared away and Tim went back to listing the dresses, so I lingered in the dress some more till I could think of no other excuses and went to ask Tim's help in releasing me. As he pulled the zip down my back he commented how much fun the day had been, and how much I had enjoyed it. I agreed it had been great fun. But there was something he was not saying, and I was not sure if it was good or bad, but I wanted to go out to the pub and I needed to change for that, 1930s starlets don't happen into pubs very often to my knowledge.
Sunday and Tim had been out before I was up, and waiting on the table was a shoebox.
'I think they will be your size, try them on then I can take them back if they are wrong.'
In the box was a pair of silver high heel sandals, which proved to be my size, if not my normal style.
'This I assume means we are going to model the rest of the outfits'
'If you don't mind' he asked
Of course I did not mind, if it was as much fun as the day before I would be silly to refuse, and went to prepare myself. We did gangster moll, a flapper and Mary Poppins before lunch. For the afternoon we had some sixties styles and fifties dresses, the sixties were easier to change, but the narrow fifties waist with the full skirts were a bit more time consuming, but more fun.
Again I prepared dinner wearing a dress, this time a pink fifties rock chick outfit, and as I had teetered around on heels all day saw no reason to take them off just because the camera was not pointed at me. I did the same as Saturday evening with the table, and then after freshening my lipstick went to tell Tim his dinner was ready.
'Dinner is ready sweetheart'
Then I had a big surprise he replied casually 'Coming dear', walked past me let his hand stroke the waistband of the skirt. I said something like.
'Oh?'
'Well you look so nice, it makes a change to have beauty around here, just like to show I appreciate it.'
I was just coming to terms with being touched in a way I might touch a woman, but not a way I expected Tim to caress me, when somehow our hands caught, for a moment we looked at each other not knowing what to do. I said something like thank you, then to both our surprise I lent forward and kissed his cheek, playing along with this charade of me being a woman. Then reality reappeared and I broke the spell by suggesting the food was going cold, we went to sit but our fingers stayed touching for as long as we could, something had happened and we knew it, what we did not know was what to do next. We ate in silence, except to ask if he wanted more food or if his wine wanted a top up.
He then went back to his computer, and I cleaned up, knowing that I would soon be undressing, and still wondering about those touches. When I was done I went to ask for help with the blouse as it had a series of buttons up the back to fasten it. When he asked why, I explained how I had no reason to keep it on, now that the pretend joke wife had finished preparing his dinner.
'So if I refuse to undo the buttons you will have to stay in this outfit, wont you?'
I nodded 'Yes'
'Well, I think I shall just leave them buttoned' he smiled at me 'You seem to be enjoying the dressing up more than just putting them on for my pics, and you do look so good, I have decided that, not only do you not mind spending the evening dressed like this, but I also fancy having a woman about the place a little longer. Any objections?'
'Cant think of any right now' and I still have no idea why I did what I did next, but it took us by surprise. I lent forward and kissed gently on the cheek again.
'What was that for?' he asked
'A thank you' I replied but seemed a bit lame, so added 'it seemed right, the sort of thing a wife of a 1950 commercial might do, did you mind?'
'No, I am flattered really, not many pretty women have kissed me lately, and I was unsure if we had done something wrong earlier.' He looked in my eye, 'we didn't did we?'
'I don't think so, it seemed right'. There was a moment as we looked into each others eyes, then we kissed on the lips.
We broke both a little embarrassed, 'I need to finish here' he stated, I also needed to go and do some thinking as well. I said inside my head.
A while later I poured the remains of the wine into two glasses and took him one; I had redone the lipstick thinking about kissing again, not sure what might happen, but wanting that tingle I had felt before to happen again.
'I was wondering if you had finished yet' I asked as I put the wine down.
'Just done the black and white Biba dress, not sure about it but we shall see.'
'You've done enough for today, come and have a rest.' I suggested
He turned and smiled at me, 'Ok dear, if that is what my darling would like then who am I to refuse.' He slid a hand around my waist as he said it.
I bent over picked up his wine, kissed him on the cheek and told him there was a good programme on the TV he might like.
We ended up on the settee at first sat upright drinking the wine, then I pulled my feet under me, and he slid a hand onto my shoulder. Next I was leaning onto him as he caressed me. Then I moved and felt his hard on; I thought this through in my own mind. I had done this to him, did I want or like the implications, did he like it, more importantly, what would I do about it.
The programme ended, and he asked if I would move so he could get up, I asked why, he said he needed some relief, so I asked what sort of relief, he smiled and looked bashful.
'A pee, or something else?' I ventured, he blushed and kissed him on the lips. It had been nice cuddled up, but the kiss sent the tingles out again. The kiss got more passionate, and our hands more insistent on their holding, he ran a hand over my arse, so I ran one over his erection, which made him moan. So I slid the hand inside his trousers and tickled the head, he moaned again.
'Now I think a wife should relieve something like that, don't you agree' I said with a grin
He was unable to speak, partly because I had my mouth over his, but I think mostly from shock. I slowly undid his belt, then his fly, then ran a hand around his waist to help them drop, his boxers were useless at holding the erection down, so I stroked it making it twitch. When I whispered in his ear what would he like his wife to do next?
He muttered anything, so I sat him down and knelt before him, running my tongue along the veins of his penis. I could hear him moaning, so swallowed the head and sucked, then started bobbing up and down. He then took control as he grabbed my ears and held me firm as he started sliding himself in and out of my mouth, then he tensed and held me tighter, I knew what was coming, I had done it myself. He came hitting the back of my mouth. I expected it to be horrid, but with the passion it was just right, and found myself licking him clean as I tried to maintain the moment.
I knelt with his shrinking penis in my mouth trying to sort out what had just happened. The taste still in my mouth was not unpleasant and reminded me of the passion, and pink costume reminded me of how I got here, and I had to accept I was happy with where I was, and gave the disappearing dick a lick and kiss just to let my emotions know this was very nice.
Tim recovered and still with his hands on the side of my head pulled me up so he could kiss my lips.
'My god, that was brilliant.' Then looked in my eyes 'How are you?'
'Oh alright, you did seem to enjoy yourself'
He pulled me back onto the settee and cuddled me in a very affectionate way.
'So what happens now?' I asked
'Well that depends how my girlfriend wants it to go, but for me I am quite happy having a woman about the place making nice meals and servicing me down there.'
'Thanks, leave it up to me to decide.'
'Alright I would love to do this again, is that clear enough, but only if you want to.'
I kissed him on the neck, then got up to make a drink, the swish of the petticoats on my legs, and the heels of the shoes shouting at my senses not to give this up, accept the offer.
When I came back with the mugs he had dressed himself again. 'OK I would like to be the lady again, this has been a great weekend for me, and I fancy doing it again. But I shall need some clothes, unless you plan on keeping some of these?'
He left me comfortable with the idea of us playing man and wife the next weekend and that he would provide everything, as a husband should.
I spent the week avoiding Tim, it felt odd after Sunday evening to meet as a couple of blokes in the kitchen, and so we tried not to. I spent computer time reading about female things such as make up, clothes, shoes and hair. I also found recipes and bought some different foods. But this was quite different to what Tim was finding on the computer, and later in the week packets started arriving, so by Friday evening when I got home from work there was quite a pile.
Tim wanted to know if I wanted to have a look, but I had made plans in my head, Friday night I was going to depilate and moisturise, then maybe try a tanning cream I had bought. So come Saturday morning I could get straight into the role. Tim seemed fine with this, but did give me few packets to look at that evening.
As planned I cleared my body of hair, and managed to give my limbs a faint tan. Then I opened the packets, a set of finger nails, a nightie and a pair of false tits. I had not thought of this but I slid into the nightie, then read the nail instructions before applying them. Then I read about the tits and glued them to my chest, which gave the nightie a far better shape. To finish off I pulled the wig onto my head and went out to the kitchen to get a drink. The silk nightie was delicious as it wrapped around my hairless legs. In the kitchen I found Tim already making a drink, he offered me the vodka.
'You look fantastic already, I cant wait for tomorrow.'
'Some of it feels odd, but thanks for everything they make a big difference' and after a big drink I kissed him purposely on his lips. 'But it is late and I think I need to go to bed. See you in the morning' I emptied my glass and picked up a coke and left him.
I tried sleeping, but the new sensations of silk on bare skin, and long nails getting in the way, and tits pulling on my chest made it seem like I was awake all night.
In the morning I went to make breakfast for my 'husband'. Then sat eating as we discussed what we planned for the day. I was going to clean and tidy, so he decided to retreat to his room and get on the computer. But not before we had checked the packets.
He had bought enough underwear for a week, several colours of stockings, a straight black skirt, and a white full one. A plain white blouse, a pink satin one, and a cashmere off the shoulder top. I had one pair of shoes, but he had got black courts and white spike sandals. There was a make up starter pack and a few extra cosmetics. And an intriguing pair of pants.
I spent the whole morning in my room playing with all the new things. Then in time for lunch and suitably dressed I went to make his meal. I wore the white skirt as I felt it more casual with the pink blouse, but thought I would need far more shopping before I was happy with the combinations. White sandals, tan stockings and white underwear, a modest attempt at make up and my special apparattus that neatly hid my male bulge out of sight, made for the interim result.
Tim was pleased and said so; he did plenty of touching and kissed my neck several times as I made the meal. We chatted about the ebay clothes and their success, then about me a little. Finally I got up to clear things away, when he came behind me and hugs me, his erection was pressing on my arse, the sensation of felling this made me feel randy and thankful all this had worked. I turned to kiss and found him passionately excited, I was soon as excited as him and letting my hands massage his member. Soon he was asking me to suck him, and I was ready by then and quickly found my lips around his helmet and encouraging moans from his mouth, and ejaculations from his dick. Again I swallowed and thought how nice the sensation was as I got to my feet,
'My make up will be a mess now' I said in mock anger, 'and it is all your fault'
We ended up kissing again, but I did want to get back to playing with make up and things.
Come the evening I had worn all the clothes, tried several make up colours and asked Tim's opinion, so when I started the dinner I was in the straight skirt with the of the shoulder top, the first sandals and what I thought was perfect make up.
We had a lovely risotto, with a nice wine, followed with a mousse and fruit. We took our time, and as I walked about I did my best to look sexy as I wiggled about the room, and tried to let the top gape at the front showing my new fake cleavage.
As we settled down with another bottle of wine things got close and intimate, the price for all these new clothes was servicing Tim, not a problem in that, but I knew it was time to make sure my man was happy. And once again I had a mouthful of semen to savour before clearing the taste with some wine and going back to being cuddled.
Tim had plans though, and the time ticked by and the TV programmes less interesting, I suggested I would go to bed. Tim responded by telling me to go and get ready for bed while he makes us a nightcap. Ok I thought and went to undress and slip into the nightie.
When I came out to get my nightcap, Tim calls me from his room.
'It's in here'
I look in his room to see him on his bed getting undressed, with the two glasses by his bed, he passes me one and picks up the other for himself. I rarely go into Tim's room and felt awkward not knowing if I should leave or what, when he smiles and with a caressing hand invites me to sit beside him. This close position restarts the cuddling, then the kissing and as the drinks are put aside and a horizontal position is taken up I find Tim on top of me, and pressing his erection into my belly.
'I feel this has all been about my pleasure, I would like to make you cum as well if you want' he whispered in my ear.
'And what do you have in mind, my dick is pretty well hidden' anyway I thought I did not want to ruin the illusion of femininity by producing a male erection of my own.
'If you will trust me, I would like to have sex with you'
It took a moment to sink in, he wanted to bugger me, but we were getting really hot and the emotions were high. 'Yes we could try it, I trust you know what to do' I paused 'Silly question really, what do you want me to do?'
First we removed the fancy thong that was holding my penis tight, and then he massaged some cream into my arse as I lay on my back all the time holding his erection. The massaging gave me an idea of what was to come when I turned over and pushed my arse into the air to let him start trying to get inside me. At first I was ok, but then I bite the pillow as I felt him push deeper, I was trying to relax and could hear and feel him working hard as he slid in and out, going a little deeper every time. I might have been in pain, but somewhere in my brain was something telling me this felt good and as he got further in and slid more easily, that little voice was saying, ohhhh great.
And then he came, he continued for a bit, but the stiffness died, and I wanted him to get back inside and pleasure me some more.
Once we had collapsed and pulled the duvet over us, he asked if I had liked it.
'Different, you enjoyed yourself I take it.'
'Oh yes, best fuck ever possibly, with best looking woman ever. Oh yes I enjoyed you' he paused 'you should be able to have an orgasm yourself, you know'
I looked at him puzzled, 'Should I? And how do you know?'
He explained how he had been reading gay and cross dressing sites which had taught him about what to buy and more importantly for the current situation, how to have sex with me. I tried to explain how I felt, but was not sure if that feeling of pleasure would result in a climax. Anyway we were both knackered and for the first time I fell asleep in his arms, in his bed.
I woke with the morning light, and after getting my bearings in the strange situation; I felt I ought to go to the bathroom. I was a mess, the make up all smeared over my face, his semen had leaked from my arse, and my semen had dribbled from my own penis, the wig was terrible, I would need hours to look good again. The nightie went in the wash and I went in the shower. It was not long before I was dry, clean with a brushed out wig on my head, wrapped in my male dressing gown. Now ready for breakfast and almost ready to be the woman again. I found Tim making toast and coffee, after a greeting kiss.
'Good morning lover, and how are you today?' he asked
'Coming round, is they're some for me there?'
'Depends what you want?'
'Toast, silly'
'Oh I thought you might have wanted something else?'
'Not yet, let me get up properly.'
I spent the morning tidying and cleaning, then over lunch we discussed what Tim had found on the internet a bit more, which lead to us looking at sites together, in particular sites on fashion so we could agree on what sort of woman I should look like. Not surprisingly for two blokes the tartier look was popular, but I knew that whatever I sounded enthusiastic over I would possibly end up wearing when Tim had purchased it for me.
That evening we slept together, only this time I cleansed my face first, then enjoyed the sensations of having him inside me again, before falling asleep together.
Monday and back to work was a sharp shock to our fantasy as I reverted back to my smart casual work clothes. And again in the evenings we were avoiding one another. But I felt it was not long till Friday. It was only a few days, but there was enough time to learn how to file my nails, pluck stray eyebrow hairs, shave pubic areas, and get a butt plug inserted. It was also enough for Tim to do some shopping, so that come Friday I knew he would produce them for our enjoyment.
The weekend started on Friday the moment I walked in the door. I was home early and striped by the door and was soon transforming myself, additions such as tits and nails glued on, underwear and makeup sorted next, the white skirt and off the shoulder top, things went well and just in time to greet Tim at the door. I got a really big smile for my efforts, and helped him into the house with a few bags of shopping.
'You started without me, I see'
'No just wanting to get the weekend started, hope you don't mind'
'No not at all, I have a few extras for you here'
'I see can I have a look?'
We opened the bags up, and he produced a few more from his room, he had bought enough clothes for a week, along with more make up and a few little extras a genetic woman might not ever want. I was excited by the clothes and went to change into a black halter mini dress that did not cover the stocking tops so I took them off. There was also a contraption for holding a penis back that after a little experimenting I worked out how to fit, and was pleased to see only a dark hairy front with no penis, ready to be covered with the flimsiest knickers I could find. So with only a dress, knickers and high heels on I went to see what Tim thought. We just hugged and kissed, the wife was back.
After dinner we went into Tim's room where he undid the halter's clasp and let it fall to the floor, his expression was priceless, I was stood in sexy heels and see through panties with no bra (the dress had supported the tits). He could hardly wait to get his pants down and massage some cream into my hole. The butt plug had done its work; I was less tight and could enjoy his attentions better.
The next morning was better as well; I had put a tampon in my arse and slipped a pair of knickers on as well as cleaning the make up off before going back to cuddling up next to Tim, slowly cleaning him up with a towel then sucking him off to leave the taste of his semen in my mouth overnight.
The weekend was easier, I knew more about transforming myself by now, and was getting increasingly comfortable in skirts, and all the add on extras. I did the housework, cooked meals and at night shared a bed with Tim, who was getting more sex than either of us had had for years, but in one weekend.
Sunday was special though, I had cooked another nice meal, we had watched a sexy DVD and then on the living room floor Tim made me lie on my back and put legs up high, then with my skirt pushed up around my waist, with the thong of my knickers pulled aside, he entered me and started to fuck, it was still uncomfortable but being able to kiss was a big bonus. But the real delight was that feeling inside that always said how nice this was, started getting more excited and screaming how good it was until I came with a shuddering spasm. I guess Tim came because I was full of semen but that was not the real point anymore, I had become somehow different, I felt complete.
Once again Monday was an early start ungluing the extras, then spending the week pretending the weekend had not happened as we hardly spoke. A far cry for our weekend relationships.
I was becoming more involved in my feminine side, and spent evenings studying and trying new techniques for the make up. Come Friday morning I went to work, with pink toe nails, a depilated and well moisturised skin, my penis already stuck out of the way and encased in panties, part ready for when I got home later that day.
The weekend saw the same fantasy played out, I strutted around looking sexy doing the wife part, Tim doing the randy husband bit, as he made sure I came again.
This worked for a month or so, but we had not been out in all that time, then Tim came in one Friday saying he had meet some friends at work who wanted him to go with them, he tried to get out of it by saying he had a new shy girlfriend, they said fine bring her along, some of the partners were going as well. He said he would try.
He told me the tale and I could see he wanted to go, and told him to go alone, I would watch a chick flick here.
He did go alone, but both of us spent the evening independently thinking it was going to get dull if I did not go out. And so my feminisation moved on.
On the Internet Tim had found a dressing service, and after a short call on the Saturday morning, an appointment was set up for mid afternoon. I sneaked out of the house in male outer clothes and a bag of what I wanted to wear. The lady at the shop was full of praise when she realised I had everything already right down to looking good naked. She taught me lots of tips on make up, how to walk in heels, what to do with my hands and head and most difficult for me, how to make my voice softer. We got on fine and soon the session was over, I promised to return for her beard removal treatment, and more tips on being a woman.
Tim came to pick me up as I was not going to drive home on my own, he was always pleased to see me changed, but I could tell he liked this version of me, a long flowing skirt, with a tight top and short jacket. This was to be my first time in the open dressed, and I was getting nervous. Linda, told me not to worry I looked fantastic, Tim agreed and said he had something special planned, and something just clicked as he looked at me, I was the wife and should do what he wants because being a man he knows best. I knew this to be rubbish but for that moment I felt like a total submissive, I had felt it a little before like when he refused to undo the fifties costume, but this was a complete submission and it worked. I walked out the door feeling he was going to look after me and show me a good time that evening. I took his hand and gave him my bag, and was lead to the car. Linda smiling at us as we left.
The evening was full of new experiences, but all enjoyable in some way, we ate at a nice café in town, went to a gay bar, then a club we had been told about and danced for the first time in years. I was chatted to by other folk, mostly the cross dressers in the bar and club, at first I was shocked they knew I was a man, but they told me they had good radar for spotting one of their own kind. I got a few contacts out of it as well, and promised to come out again. The bedtime was excellent as well, maybe being pumped up with the whole experience, but I just let Tim do whatever to me. First he had me over the arm of the settee, and then once he had recovered and I had got ready for bed he had me again, and then asked me to blow him. He knew he was in charge and enjoyed controlling me in the bedroom, and just accepted it without question. Even at the time I found it hard to believe, but that was how it was, I would do whatever he asked.
Things did change after that, I visited Linda every week for laser treatment on my beard, she also started to thin my eyebrows a little at a time. I would wear panties and keep my penis taped away most of the time. My nails became longer. My uncut hair was getting longer and needing a cut but I felt wrong about having it short. We also went out at least once on a weekend to the bars we found through the friends we made. But most telling was when Tim accepted an invitation to a work party and he just told me were going, no discussion, he was in charge and I would go. I asked if I could go to Linda's for a make over, and a new dress to which he agreed. I thought after how girlie, I just do as I am told and let him buy me a new dress and that is fine, where was the man in me now.
I bought a nice conservative black and white dress with white heels, Tim bought me a new wig that was longer and more full than the other, and it fastened to my head so well it took a really good pull to make it move unless you undid it correctly.
The evening had me very nervous, I could screw up things for both of us if I was found out by his work colleagues, but Linda helped with special care over the make up, and checked everything about me. It had been explained how I was shy and nervous, so people allowed me to stay by Tim's arm and not say much really, but as the alcohol took effect I fell into conversation with some of the other women then a few men. It was mentioned more than once that Tim had been considered gay because of his lack of girlfriends, but they were happy to see he had found himself a partner at last. I just wondered how homophobic they were, but felt it best not to find out.
It was late when the taxi dropped us off, and for the first time ever we just went to sleep without sex, a reflection of how draining the evening had been on me.
Next morning Tim made breakfast and told me how wonderful I had been, and when he had been to collect his car, came back with more tales of how I had won over the party to believing I was his girlfriend. And as I stood there looking like his girlfriend who was I to argue with his comments.
Things were changing, nothing happened together but with hindsight it was obvious where I was going.
With there being no need to shave anymore my face looked more feminine than before and needed less make up, which was nice. But the thinner eyebrows I now had emphasised the feminine.
When I damaged a pair of work trousers I replaced them with some fitted jeans style that had a flared leg and a flat front, which with my penis out of the way I thought looked good as well as being comfortable.
My hair reached the bottom of my ears, and I was constantly tucking it behind my ears, and it was getting harder to hide under a wig, so Linda made me go to a salon and have a trim, I was not sure what to expect, but asked for something I could wear as a man, so Linda set it up with her friend and explained how it should be cut. I ended up with it very feathered and spiky, hardly a macho cut but in today's styles possibly acceptable. But when blow-dried and gelled up it was definitely a woman's cut.
Then there was the time I got my ears pierced, Tim had decided we could go out shopping for everyday things together, and one day while passing a jewellers he paused and commented how nice the ear rings were. I told him I would wear the clip-on more often if he likes them, but as he looked at the jewellers he was amazed at the wide choice. I knew what was coming; he persuaded me after some resistance on my part, I still had to go about as a man for work purposes. But he was sure no one would mind, at least not after I had had my hair styled. I gave in, had studs inserted and took the cleanser home to stop infections. And he was right no one made a bad comment, there were comments, but they were just that.
About the time my holes had healed up nicely and were ready to take more decorative jewellery I went to have my hair trimmed at the salon, this time I went in as a woman and as Linda's friend fussed around me I found myself agreeing to having some colouring, nothing wild, just something to add a richness I was told. Well after several washes and liquids rubbed into my scalp, then gelled and dried, I had to admit I did like the result, I was lighter and there was more shine. This was followed a month later when the darker roots started to show with the tips only being coloured, which made the spikiness more pronounced.
Of an evening I was finding it quite easy to brush my hair up, put in some nice earrings, add lipstick, change my top, I might not change my trousers if I had on the flares and finally slip on some heels, ready for Tim coming home, which by midweek he always appreciated.
Things had got so feminine in my looks I got teased at work, and I had my name femininised to Paula by the closer friends then by a wider circle till everyone was calling me it. Janet who sat near me one Monday morning came up close and asked if she could smell 'Obsession'. It was the one I had worn on Sunday and stunned for a moment as I tried to come up with a good answer, I gave it away with that pause and my blushing cheeks, she smiled and said it is a good one. My first definite lapse, and being found out. After that she sat with me at the canteen and gently picked up my fingers before commenting how well I kept my nails, especially she said the coat of clear polish to protect them. I felt rumbled but she asked no more and seemed happy just to know that she was right about her observations.
A big change came when the company wanted people to do home working, I was mostly answering customer queries and sat at a computer all day, so I was an ideal candidate to do it and free up office space. At first it was an experimental day a week. It worked so it went to four days with one day for meeting the rest of the team for updates and training.
When I told Tim we both knew what this would mean, I only need be Paul one day a week; in a way I was going to pretend to be a man for that day when I had a flat chest and wore my buttons the wrong way round.
Who would have guessed how my life had changed over the past months to get to a position where I would consider dressing up as a man to be something odd, and most definitely disappionting, but we can't have everything we want, and twelve hours out of a week is not bad by any standards, especially considering what I sort of a life I was leading the rest of the time.
Now I always thought myself a normal regular bloke, nice house, nice car, pretty wife etc. but this past year things have got very interesting.
One thursday evening we were sat watching a soap, Kelly was idly filing her nails, and I have always told her how nice they make her hands look, but this time I asked if long nails made things difficult as she sometimes asks me to open ring pulls, for example, she replied that she has got used to them. All I said was oh, why do you ask she enquired, so told her I was curious why they don't get in the way. We chatted about why we liked them, then dropped the subject. But on Friday evening when I got home she smiled and said she had something for me, in the bag was a pack of false nails, 'Come here, if we put them on you now, you can find out what they are like for yourself' she smiled and rather than argue, let her take my hand and glue a nail onto each finger tip, then because they were rather white and plastic looking she coated each with two coats of a pale pink varnish. At the end all I could say was 'Gosh they do change how my hands look' 'They lengthen your slender fingers making them elegant don't you think' I nodded, she continued 'but now you can find out how they feel, which is what you were asking last night' 'Suppose so' and was challenged with eating a meal almost immediately, cutlery being the first items to alter my handling skills.
I spent an awkward evening poking myself with my pink talons, then trying to use the pads of my fingers or the tips to do things that previously had been so easy, simple things like washing had to be done carefully, holding cutlery had to be done differently, everything in my dextrous world had changed. Many things were harder but when we got into bed I remembered how I like Kelly to gently draw her nails up my inner thigh and as we cuddled I did the same to her and got a very positive reaction and she told me to do it again.
At last we slept, but in the night I lost three of the nails. I was intending on pulling them all off anyway but she persuaded me to keep them on for the weekend and give me a good chance to get acclimatised to them. I had to keep my hands in my pockets when we did the grocery shop, but as the day passed so did my awkwardness, by Sunday evening I was behaving like I had always worn my nails long, Kelly made it clear she approved of this new feature in my look especially how they felt when I caressed her. As I was removing them she asked if I had enjoyed experimenting with the nails, I said how they had felt weird and how I had learnt to adjust, when she asked if I would do it again, I said 'I don't know' 'shame' she replied 'I quite like you experiencing a bit of what I do to look pretty, and they make your hands look so nice, and there is also that special touch you can do with them as well' she said with a smile.
Things were busy for a couple of weeks, but then we had a quiet weekend to ourselves and Kelly was there on the Friday evening encouraging me to extend my nails once more. And while she cooked the tea I glued the extensions on, then painted them a dramatic plum colour. it did not take long before I had the hang of them once more and Kelly was enjoying them on her skin. I enjoyed them all weekend, in fact was a little disappointed to see them go on monday morning.
My next experience with femininity came at a clothes shop, Kelly was trying on trousers in the new style to her that was loose and soft, I made some comment about how comfortable they looked and how they are so different to my woollen suit pants or jeans. To my surprise when we got to the check out she had two pairs 'Something for you to try when we get home' she whispered.
They were everything I expected and more, they were so soft and caressed my skin in a most unusual but pleasing way. 'Shall we keep them?' she asked me. 'Very nice and different, but when would I wear them?' 'About the house' she suggested. And so for an experiment I kept them and wore them all the next day too. Then she asked me again, this time I said yes, they were lovely to wear and I would be keeping them.
My next experiment started when Kelly was massaging her feet after a day at work, I asked why she did not wear flats, 'because I want to look my best' 'but they must kill you, I cant imagine how they must feel' Well that was all it took, next time she was shopping I ended up with a pair of plain black courts and an uneasy stride until I got the hang of how to balance myself when an extra 2" heel was under my foot.
The trousers and shoes were far easier to accommodate into my male life as they were easy to change if I wanted to go outside, the nails being fixed did not make an appearance so often, but the next time I had no reason to go out at the weekend I spent it in all my feminine pleasures. Kelly seemed to find this amusing and suggested other things I might like to try, maybe a long flowing skirt, higher heels, long hair, smooth skin. These were the ones I remember but there were others, but these seemed the most removed from my usual male look.
The next thing to happen was I found a new pair of shoes alongside my modest 2" heels which towered over them at 4", now I found out why women complained about heels, but for the sheer hell of it, and to master something new I persevered until I could walk easily in them. I even came to like the sound of the heel's clicking as I walked on the hard surfaces and the way my posture was affected, making me stand more upright and poised, using my hands for balance as they stuck out in a camp fashion.
Then she bought me a calf length, soft cotton skirt, there was just so much of it as I walked, sat, generally went about my normal day at home, that I realised here was something else that was alien to my life until then, and was encouraged to wear it so I could learn how to enjoy it in much the same way I enjoyed the trousers, soft fabrics brushing against my legs was something I had easily got to like.
My next experience was to try out long hair, and I mean long hair, down to the middle of my back. Kelly had short hair by comparison as hers only reached her shoulder blades, I was in for a whole new set of challenges. Every time I leant forward the hair came forward too, it went in my food, my mouth, my eyes, absolutely everywhere. But I continued with the wig, Kelly insisted I was not to tie it back and that I should keep it well brushed, as well as shampooing and conditioning it while wearing it, then blow dry it, which took ages. By the end of a couple of weeks wearing it in the evenings I was getting the hang of keeping the hair out of my face. Then following a weekend at home in all my female affectations, nails, heels, hair and the skirt, I went to work on the Monday with a bit of a mince, holding my head as if I had long hair and using my hands as if the nails were still attached. Kelly noticed when I got home and asked why, I just kept it honest that I was getting so comfortable with female things, I just seemed to be doing things now without thinking about them.
One evening later that week, we were discussing what I should experiment with next, when Kelly suggested that I combine all the things I had and go for the complete woman image, including make up, hair free body, and a chest. I was a bit reluctant to say yes as I could not see how doing all these things was learning new things or a challenge, so she explained how make up would fit in with those principals. Which meant the next evening I was being taught about make up, the products and the effects they created, then after a few attempts I was left to practise. It took a few evenings but when I considered myself confident I went to show her my new face, glossy pink lips, defined cheek bones, sultry eyes, she told me I looked very sexy but I did not believe her.
This new found skill was used further on the next quiet weekend, Friday saw me gluing the nails on, fixing the wig, then for the first time removing all my body hair, before going to bed in a silk nightie. The morning continued in the same way, I stayed in the nightie until I had eaten and washed my hair, which Kelly then styled for me. I took an age over my make up, then I was given my first set of underwear, satin bra and pants with stockings, all covered up by the skirt and a new top. When I looked in the mirror I knew I would look pretty good as my legs always looked good, but the surprise was how good my head looked, my hair was right and the make up done for daytime was perfect. We spent what was left of the morning doing housework until Kelly wanted to do some food shopping, she tried to get me to go as I was but I refused saying I would be an embarrassment, she insisted I would not be and I agreed that I would leave the house but was not sure when or where I would go. While she was out I did some research and found out about the area of Manchester that is friendly towards cross dressers, and showed Kelly when she got home. Her attitude was, strike while the iron is hot, meaning she wanted to go that evening.
Early evening Kelly changed into a 1960s style mini dress, while I redid my makeup for the evening. It was dark so under cover of darkness I hoped to get away from twitching curtains before anyone noticed I was dressed this way. Soon I relaxed as Kelly drove. We parked near the bar suggested on the website, bought drinks and stood back to watch what happens. I had never seen so many openly gay people, men and women behaving in such intimate ways, at first I was a bit shocked but soon came to realise it was just their thing and meant no harm by it, then a camp man approached us 'Wow, you are absolutely gorgeous' he said in a high camp voice. We thought we actually looked like a couple of gay women, but this man recognised me as a man, though he was very complimentary, telling us how he dressed himself, and had a thing about spotting cross dressers. Phil proved to be good company and when he wanted to move on invited us along, in doing so we got to meet several of his gay friends, and as we relaxed found ourselves easily slipping into converstion with them. The evening was a great success, and as we drove home discussed our time there, I had been chatted up twice and had a man's hand around my waist once, Kelly had been chatted up by a man, and a woman who had kissed her on the lips as they parted. The buzz was carried through to the bedroom as my very stiff cock was used by Kelly who for the first time in ages was on top and enjoying herself.
We both knew we would be down there again, and when Phil rang to ask if we were going the next Saturday I said yes and he said he would get dressed up as well and where we should meet. The next Saturday evening I prepared myself well and chose the trousers and a tunic top I had bought to go with them, but to say Phil made me look dull would be an understatement. We did not recognise him until he came over and air kissed us. He was teetering around on ultra high heels, and wrapped in a silver lycra dress that showed no hint of a man, on top of which was a mass of blond curls, this was a cross dresser, no woman would dress quite so slutty, I swear you could see his knickers if he bent over just a little. After introductions to his friend who he described as his pole for the night, we moved on to a few more bars ending up in a club that has free entry for cross dressers. Another great night, niether of us could believe how easily we were accepted by this gay community, nor how promiscuously we behaved, allowing people of any sex chat us up and touch us quite intimately. As expected we had another good time in bed releasing the sexual tensions that built up that evening.
From then on unless there was something we had to do of a weekend we would be found in this gay area of Manchester enjoying our new friends and new found ways of enjoying ourselves. I found I liked dancing, Kelly found she enjoyed the less macho attitudes of many gays appealing, and the more relaxed non threatening touching of both sexes. Then one evening we found we liked the close attentions of our own sex. I was dancing with a man who had been chatting with us, but we danced close, he kissed my neck, I felt a tingle and looked over to see if Kelly had noticed, hardly I thought, she was sat with a woman who was very tenderly holding her hand and stroking her arm. So in the interest of experimenting when he kissed my lips I reacted positively so I could find out how it felt. It was not brilliant, but ok, he was in charge and controlled the kiss. When we broke at the end of the music, I saw Kelly watching me with a smile on her face, and her friends arm around her shoulder.
Besides our encounters with our own sex increasing so did my wardrobe, Phil encouraged me to be more outrageous, but I saw him as a queen while I prefered to be a princess, pinks and frills being my chioce for a night out, but more plain for home, even buying a biege cotton skirt for doing housework.
We were discussing some people we knew on our way home, when Kelly mentioned that Geoff fancied me, I said no way, besides I loved her and would not cheat on her. She explained how she saw things, she loved Brian, but Brie (as I liked to be called when in a dress) was more of a friend, maybe a lover, so for Brie to go with Goeff would not be difficult for her to accept. I was floored and said I would need time to think about it. On reflection I had done everything bar get a mans cock out already, I had kissed, cuddled, been aroused and felt a cock rubbed on my thigh more than once, and knew what it meant. She made a point that I had not tried any new experiences recently, the most recent, which I had opposed at first was my visit to a female salon in full dress so I could have studs fitted in my ears. Not only had I experienced the anticipation but the actual pain of the procedure, I had gone into a very female enviroment, pretending to be a woman, which was new as well. Undetered Kelly later explained some more how it could be part of my experiencing what it is to be a woman, to lie back and let a man fill your hole. But once in bed she rather intimately with a vibrator showed me what it might feel like to have a cock in my arse. It was not unpleasant, but did nothing for me, but clearly stimulated Kelly who mounted me and had a great time, while the dildo carried on stimulating my own hole.
I did my research into gay sex, and discovered the dangers, problems and possible pleasures associated with it, I even tried using the vibrator on myself as it seemed I needed to get the muscles used to the invasion. Then on Thursday I had a call off Geoff, (Kelly and Phil had set me up I found out later,) inviting me out on Friday night. I was ready for it and said I would love to. I spent the time from getting home up to eight getting ready, the hair styling, make up, nails, dressing all took time, but I felt good when I finished. Geoff was downstairs waiting for me when I pushed the final earring through it's hole. He was looking very smart in a suit, I was glad I had gone for my sexy but conservative silk wrap dress with a knee hem line. Kelly kissed me good bye rather like a friend might, not a wife. Geoff was a gentleman, he took me to for a nice meal then onto a pub with a live band near to where he lived, then after a short walk to his apartment, we soon found ourselves inside his front door and kissing properly. He unfastened my dress, then told me to undress him until his cock was on show, I knew what to do next, Kelly had done it to me often enough, I stroked it with my nails, then kissed it before he picked me up and carried me to the bed, where we prepared with condom and jelly, then he took me. I did not have any feeling of orgasm but I did feel like a woman. Geoff had filled my hole, which I thankfully had been stretching, and now he lay on top of me as he recovered. I now could empathise with Kelly when I had come and not bothered to let her enjoy her moment as well. But I was satisfied in a new way though, Goeff had treated me like a woman, we had been to straight places which meant he was confident I looked like a girlfriend, then he had taken me to his bed and made love to me like a woman, and as I lay beside him brushing my long hair from my eyes with my long nails, I felt a deep sense of being satisfied and comfortable. Then without really considering what I was doing, burrowed under the sheets and massaged his cock to life before sucking it so I could expereince the taste of spunk for myself. Another eperiment to tick off I suppose.
The morning was a realisation of what I had done, hair was in my eyes, make up all over the pillow and my face, an odd taste in my mouth and a sore arse. Goeff was up and making some breakfast, returning with it to find me hiding in the toilet, he suggested I shower and use his dressing gown. This helped freshen me up and cover my modesty, but I felt naked without my female face in that situation, and how would I ever get home. He was very supportive but in the end we called Kelly who came round with a change of clothes and make up so I could leave looking decent.
The relationship changed that morning between me and Kelly. We chatted as we drove, I was in a plain white blouse and green patterned skirt, so I was just an ordinary woman to the casual observer, but Kelly was not a casual observer, she was wanting to know all about my evening, where we had been, what we had seen, what we had done. There was no hint of jealousy or bitching that I had been with someone else, the situation was new to me and it felt like two friends sharing their experiences, I felt like Kelly was seeing me as a woman just like her. This was unexpected and quite flattering as well as nouvelle. We shopped on the way home, and when we passed a jewellers she made a joke about me being a butterfly coming out of my chrysalis, I laughed and pointed to one in the window, and on the spur of the moment I was having a belly stud inserted with a butterfly on it. This meant a new stage in my female experience, I now had something overtly feminine that I could not readily remove or disguise as male like the ear studs, at least until it had healed, I would constantly have a feminine reminder on me and come Monday at work I would still have it. But for that Saturday evening I wore a crop top and tight satin trousers to show off the new addition to my look. Phil spotted it straight away and worked out the significance, Goeff complimented it but did not get the butterfly thing until it was explained, then he was flattered that he had had a part in it, he made sure I always had a drink and enjoyed some very intimate dances together. Kelly did not seem to mind that I was not paying her much attention as she was being equally looked after by a girl called Jo, Doc martins and short hair, you know the type, and when I saw the passion of their kissing I guessed it was more than just good friends, rather a bit of experimenting on her part.
It was well past midnight and Geoff was letting me know how randy he was feeling, I said I wanted to sleep in my own bed that night, so he asked if I would sort him out in the trouser department, I am not sure what I said but he responded by leading me into the toilets having a furtive look around and when the area was clear pulled me into a cubicle, then as he unzipped himself he asked very nicely if I would take care of him. His tongue was deep in my mouth, and I handled his cock and balls, but then as he got more excited he pushed me down until I was facing his erection, 'Please' he implored, I kissed the tip and the next I knew the head was in my mouth, he thrust a couple of times making me choke, then he came, I know there is not much, a teaspoon possibly, but it seemed to fill my mouth. As he withdrew I was left with a taste in my mouth and an unpleasant feeling in my stomach that I had been used. Quickly he tidied himself up, gave me a kiss, but noticably not on my lips, then opened the door and left. I followed shortly after, when I had been in the ladies and checked my lipstick, then went to find him, but he was gone, now I did feel used and went to find Kelly who was in a deep embrace with Jo. She realised I was there and after a minute asked if I was alright, I look that bad was all that went through my mind. Within five minutes we were in the car and heading home. I told her how I had felt used, and after she had explained how some men are, I asked how her evening had been and got a full tale of how good Jo is, and how they fancied going out next weekend to a show they both wanted to see, as an after thought she invited me, but I knew I would be the gooseberry and in saying no to the invite was giving my blessing to her going on a date with Jo. Now that was something niether of us foresaw when I started experimenting with long nails all those months ago.
Things were happening pretty quickly in our relationship, I had been with a man, and it looked very much as if Kelly was going to be initiated into the ways of lesbian love making before long, especially if Jo had her way. Midweek I was on the phone with Phil and told him I was on my own at the weekend so he suggested we go out together, get all glammed up and go on the pull, when I asked what sort of a girl he thought I was, he said, one that needs to taste and feel some more cock. I was instructed to be round at his house late afternoon in with my best pulling outfit. He suggested a deep pink tube dress, and and my towering silver spike heels. I said I would think about it, but the more I thought about it, the more I thought, what the hell.
I left home as Jo arrived to take Kelly for a pre show meal, we parted with a cheek kiss, well, I was in a sundress and just friends. The sundress disappionted Phil, but then I showed him the contents of my bag, he hugged me telling me I would not regret it. First we had some wine and a bit of salad, then Phil suggested we get ready together, this was going to be interesting I thought, I was soon sat on his bed in my bra and knickers being shown his wardrobe and having to comment on what I saw. He ended up picking a black disc mini and a black halter neck top, the outfit left an awful lot of skin on show, he pointed out how little I was covering up as he produced a bottle of tanning solution. We then spent a very enjoyable and occasionally erotic half hour drinking vodka and massaging the cream into each others skin. Now I usually wear flared skirts and this was my only tight fitting piece because my control pants did not really do a complete job of flattening my front, nor did they look that sexy, but that evening I was shown what tape can do to a man's privates. Phil assured me no one would be the slightest bit interested in that part of me, so it might as well be stored out of harms way. My balls went inside with the penis taped between my legs, I was surprised how well my crotch looked, especially when I pulled on a lacy thong. We finished our make up, draped ourselves in jewelery, climbed onto our stilts and killed any smells with our perfume. We were ready, a light coat to protect our modesty while travelling in the taxi, but besides that, modesty was the last thing on Phil's mind.
We hit the bars already having had a few drinks so my inhibitions were down and my passions up. We started of by teasing some gays we knew, then after about half an hour I looked around to find myself alone, Phil had disappeared, he came back licking his lips, 'Number one to me I think' I stared incredulously at him, he pointed at a man, 'You have no shame' I said, he agreed and we both laughed. I now knew what the evening was going to be all about for Phil, so when I saw Geoff I pulled him to one side and suggested we go somewhere quiet, ten minutes later I found Phil after a quick visit to Geoff's car and an unloading of semen into my mouth, no choking or pushing this time, I did it my way and used him. On meeting up with Phil I gave him a kiss and let him taste my conquest' 'That was easy, he fancies you rotten' 'give me a break' I replied 'I am not used to this' but something told me I soon would be. Sucking Geoff in a car park where people could have seen what we were doing was quite a buzz.
I was not up to Phil's brazenness, I enjoyed plenty of attention but when it came to sex I was asked twice but only accepted once, from a nice man who was particularly nice to me and did not seem to be terribly forward until he put a hand on my thigh so I stroked his and found out I was getting a positive reaction, we got a little bit closer and personal, Phil tried to tell me I should just have him and move on, but he was nice and I enjoyed his company. Eventually after some dances and me asking if he wanted me to take care of him, he said 'Not here' 'Where?' 'Somewhere much more appropriate and suitable for a lady like yourself' He lead me down a few streets and into a converted warehouse where he lived, the apartment was very stylish, 'Better?' he asked 'Much' I answered as he put on some music, then went to the fridge and poured out some wine, handing me a glass and saying 'To us' 'To us' I replied, I took a sip. It was quieter than the bars and we could chat easily, so we sipped, chatted and carressed until he suddenly said, 'So you want to know if you can take care of me?' 'I wanted to know if............you know........sort out your bulge down there' with that he took my hand and lead me to the bedroom, a luxurious king size with black satin sheets. We fell onto the bed while I was undressing him. Very soon I had lubricant in the right place and he has a condom on and I am lying on my back wanting him to fuck me. Never in my wildest dreams had I wanted sex so much. From the moment he entered I was excited, but when I felt him go all the way in and touch something deep inside, I moaned and told him to do it again, he was brilliant and did as I asked, and touched that spot, again and again and agian until I felt an explosion inside me unlike anything I had experienced as a man, then he let go and climaxed himself. Spent, we lay together in each others arms as I told him how wonderful that had been, and how lovely he was. Suddenly I noticed the time 1.30 and remembered Phil, I found my phone and called him. 'Was he any good' he asked 'Brilliant' I answered, 'On number four myself, but he is rubbish really, he bought me some food and a few drinks and I was feeling sorry for him. Sharing a taxi back?' I looked at my man, what was his name? 'See you in fifteen minutes'. I hung up. 'Can you walk me back to meet with my friend' he never even questioned it, just dressed while I striaghtened myself out and wrote my phone number on his bathroom mirror, I had seen it on a film and always thought it cool, and now I had done it myself.
In the taxi back to Phil's where I had planned on sleeping that night, we were comparing notes of our conquests when a text alerted my phone, he had walked back and seen my number calling it immediately, so he is keen I thought, his message confirmed it 'sunday lunch, maybe more. xxx Zack' Phil saw it and told me I would be a fool to say no, so I sent the message back saying yes. Goodness knows what the taxi driver thought as we giggled and hugged on his back seat, but who cared.
After a short sleep at Phil's I was up and back in my plainer sundress and driving home, There was no one up but as I put on the kettle, Kelly appeared looking groggy, 'Good night?' she smiled a satisfied smile, 'Yourself?' 'Not bad, going out for lunch, hope you dont mind' at which point Jo walked in looking sleepy wearing my Brian dressing gown. 'Hi' I said 'Hi Brie, have a good night?' 'Maybe, not as good as yours it would seem'
Soon we had drunk our coffees and Jo had left us, and while I showered and changed for my lunch date, smart trousers, tunic top, hair up, 3" sandals, Kelly pumped me for information, while at the same time being quite forthcoming about her own night with Jo, and it was not just the show that had been better than expected. At twelve I drove into town to meet Zach at his chosen destination. A nice meal, very interesting conversation and then an adjournment to his flat, this time I was not drunk but was just as keen to get laid. This time we took it slower and more tenderly, until my nerves erupted again. I could get addicted to this was my first thought as I came down, hugging my lover as tightly as possible until he came. 'No rushing off this time' 'I need to go to work in the morning, and I cant go in looking like this, but until later I am stopping. If that is ok with you?' 'Most certainly, I would love you to stop as long as you want'
That was my first weekend with Zach, and I could not wait for the second, we meet Friday evening, then Saturday evening, stopped over, remembering some Sunday wear, then lunch again and an afternoon cuddle. Perfect. Monday seemed so dull by comparison, and sleeping with Kelly was just that, sleeping. On the Wednesday we tried to get excited as man and woman, but it was just doing it for the sake of it, I think both of us were wishing it was someone else with them instead. And come Friday it was.
It took four weeks before we sort of came up with a weekend arrangement, Kelly wanted Jo to stop over, and I was keen to stay away, so with a small case I moved out on the Friday evening after I had changed, until Sunday evening when reality and work came back into my world. Soon I was doing nearly all my Brie living at Zach's apartment, and my money earning Brian life with Kelly. I much prefered the Brie days as Zach spent time with me, I would cook for him, he would take me out, I would satisfy his manly needs, he would buy me clothes, I would sort out his computer, he would fuck me. It was a great combination. And then I would go back to Kelly, sleep in seperate beds, and sit chatting about what we had done over the weekend, her tales being not to disimiliar to mine if you changed a few of the non sexual activities.
Six months later and Zach has got me go for a full salon treatment, waxing, tanning, massage and now my hair was long enough a restyle, I loved the pampering, but dreaded the Monday reaction. I now had a long sweeping fringe and feathered neck in a chestnut colour, someone was bound to say something. I prepared myself for a bad day, but got a terrible one. At the lobby I was told to go to HR, who in turn told me the firm were downsizing and I was no longer needed, wished me success in the future and escorted me to and from my workstation. I was home before dinner.
Kelly was shocked and wanted to come home to hold my hand, Zach however came round without asking and took me to his place. He listened as he always did and offered sympathy, but then looked for the positives. With my skills he reckoned I could set up on my own, and without work to go to I could live as Brie fulltime and stay with him as I no longer needed to be at home which was near my old job. I spent time pondering my options, contacting job agencies and ringing friends all day Tuesday while Zach was out. When he came back I had a meal prepared and he told me I had my first job as Brie Programming. I start the next Monday and they wanted me for a couple of weeks to sort out their payroll software, he also rather pointedly made it clear they were expecting a woman. I thanked him every way I could, but the most enjoyable was slipping between his satin sheets and letting him do whatever he wanted to do to me. On the Wednesday I rather sealed my look by calling at a nearby nail salon and having permanent extensions fitted to my finger tips, there was no easy way to be Brian with talons like those, then I plucked my eye brows to a neat tadpole shape and went back to see what Zach thought. He loved it, telling me I might as well clear out all the Brian stuff from his place as he would never expect to see me in anything that was not pretty. An easy demand I thought.
Thursday I went back to my house to sort out my past and have a meal with Kelly who looked sad at my decision, but said it was going to happen, almost inevitable we agreed. I left all my Brian stuff there, until either Kelly moved on or a year had passed without me needing any of it, then I collected all my Brie stuff and went back to Zach's for the start of my new life, but more immediately, 'a good seeing too' as Kelly had put it once, when I described what we got up to. Needless to say I was not too busy cooking and putting my clothes away, to find time to satisfy my man!
Another story with a vague contact with reality, just a ramble into my imagination.
Working in the family business is not always the best choice,but it depends if you like the work
Not all under height boys that live with a single parent mother are going to turn out to be effeminate, and I was certainly not planning on that. I fancied girls while at school and even had a few close friendships with the opposite sex. I liked sport and did boy stuff as a kid. But I was also thoughtful about my mum, she looked after me and I looked after her. We lived in a small house in an ok area, schools were good and there was plenty of space for me to get out if I wanted. So a pretty ok childhood. I did my GCSEs and did ok, then I tried A levels and did well enough but I could see a move to uni would be a strain on the finances, so I stayed at home and looked for a job when my friends left for the delights of student life, that being, poor diet, alcohol and debt. I suffered from none of those, but I did miss out on the lifestyle. Living with your mum is a little cramping when your mates are very independent, well besides financially.
I discovered that eighteen year olds are not a much sought after age group and was resisting the temptation to make my Saturday job fulltime. Five days of shelf filling in a supermarket was not a great future I told myself. Then my mum's brothers offered me a job. They were builders and reasonably good ones it seemed, they had nice houses and cars, they made sure we were ok as part of the family. There was a story that I was conceived while mum was having a thing with a lad who the brothers did not approve of, when mum got pregnant they made it clear there was no way he was ever going to be a brother in law. The lad was never seen or heard of again, my uncles said they would look after us, and they did. Though I never meet my true father, it was clear that he was not a big bloke, the men in the family were big strong men, I was like I said, under height and under weight.
Turned out the uncles needed someone to run the office, their wives and mum had all done it for a spell but for one reason or another had all left, I suspect before there was a big bust up and marriages ended over the accounts being done differently to how they wanted it doing. Well I had done business studies and felt well equipped to do the job. That was until I started. I got myself onto courses locally for suitable subjects like accounting and the computer programmes they had. Things were going fine, I did as I was told, they gave me a load of stuff to sort out and I just did it without questioning. Then I started to think about how the office worked as a whole, and made a few suggestions about filing first. As long as they could find what they wanted that was fine. So I introduced a structured system that was far better than the previous, which was basically making a pile, way of doing things. Then I got more into the numbers and was not so good at changing things, but the accounts worked and that was what the taxman wanted.
Over time I got to be quite good at the job, the paper trail was easy to follow, the desk was tidy, I even got the place painted and updated though I had to do it myself at the weekends. Things started to go awry during the boom years just before the recession. Work was good and the brothers were doing well, they bought new cars, went on flash holidays etc. Yet I was still on my basic wage that was not bad but I had thought I was part of the family business and would benefit from the rewards when there were some. Well I was not getting any rewards directly so I devised a plan.
I had been given authority to sign cheques when I was twenty and had more or less become the main person to see if suppliers wanted paying, so I started off by putting through small petty cash receipts. Then I made copies of supplier invoices for goods we never had, and made the cheques out to cash and then banked them. I wanted to save for a deposit on a house so I opened a new account separate from my own and the business bank and watched my savings grow. The uncles never questioned anything I was doing, every now and then coming and taking a cursory look at the bank balance or the latest cash flow, then leaving me to it. They seemed happy with my work even if I was not, they were not that bad though, they did give me a company vehicle, I would have liked a little hot hatch, unfortunately I got a pick up that might well go missing in the day and come back caked in mud, not the best choice, but I got my travelling for free, I did however run the risk getting dirty just using the truck.
Well, not long after I gave myself the 'bonuses' I got to thinking that I needed to keep the fact that I was taking the money as secret as possible. It was unfortunate that I saw a man dressed as a woman, I mentioned this to mum who said she had seen him, apparently a transsexual, but in her words 'No matter how the person feels inside, her body just does not want to cooperate' We got into a conversation about sexuality and quite openly talked about how we felt, which was quite surprisingly liberal, somehow you always think parents will be perfectly straight. Anyway I got to thinking that I could disguise myself when cashing the cheques, then the bank CCTV would not recognise me if I was ever questioned about it. I could always say I never went in that bank, look on the CCTV.
So I spent time at home researching the possibilities, then I went shopping but this was far too nerve wracking. I would go into a shop look at something female go bright red and have to walk out, I bought nothing for weeks, then I came across a shop that caters for cross dressers and after two aborted attempts made it through the door. I was beginning to doubt how liberal I was after not even being able to walk through a door to a clothes shop. Once inside my nerves were calmed by a nice mature lady who offered me coffee and a chance to chat. I told her I needed to look like a woman for a bet, she asked how convincing a look, my back story was not complete and I made it up on the spot, and if I wanted to walk into a bank I needed it to be good. So I told her 'Good enough to walk down the street' she explained that I would, with her help, be able to walk out the door looking entirely female, but if I did not want to attract attention I would need to walk, move, gesture, pose even stand like a woman to carry of the deceit.
It was as I sat there with my empty coffee cup that I decided to give it a go, I asked how much and though expensive could justify it as an investment so I could gain more. Two hours later I am drinking another coffee while watching TV in a sitting room above the shop. She had dressed me in tight fitting business suit, grey with pink threading I think it was, a pink silk blouse with a pussy bow at the neck. My face was made up, a dark blonde wig sat on my head, my finger nails painted a shiny pink. All of these on their own were alien to me, but the heels were the weirdest thing and I immediately saw that walking out dressed in female clothes did not make you look like a woman, there was so much more to it. She let me have a few changes and I have to admit that the satin bridesmaid dress I wore that day was possibly my best ever, the colour was right, the fit perfect, but it was the feel that won me over, satin would always be my favourite material from then on.
I remember getting home that afternoon and mum asking if I had been doing anything interesting, I said I had just been in town looking round, but she gave me a funny look and told me she was fine with whatever I wanted to do or call it. Then I went to the bathroom and saw that I had not cleaned off the makeup as well as I thought I had, my eyes had watered and must have been my downfall. This however was to prove my entry into femininity. Over our evening meal and a bottle of wine it finally came out that I had been to a cross dressing shop, my excuse being I had wanted to find out more for myself before I make a judgment. Very good, she praised me, and then asked how I liked the experience. I was soon telling her about what Elaine the dresser had told me, and how wearing the clothes does not create a woman, but I also told her how nice the fabrics were and how interesting some of the items had been, shoes for example. Then I told her how much it had cost, to which she calmly offered to help me dress if I wanted to in the future. I could not tell her why I wanted a disguise and told her thank you, and that I would like to find out more about visual differences between a man and a woman. She smiled at the prospect as she told me it would be interesting see if we could go out as mother and daughter one day. I was still thinking of a disguise for cashing cheques, mum was clearly thinking something else. It was late when we finally went to bed but she had planned how we might set about making me into a convincing woman.
The next evening over tea, with clearer heads she asked me questions like shoe size, chest size and so on. Then by the next weekend she was able to present me with a few bags, she said to get me started. Some heels, a wig and a starter make up kit, along with several bra and panty sets. I must have looked nervous as she asked if I wanted to give it a go, she could take things back as long as they were unopened. I managed to stumble some words out like 'It will be fun' while thinking 'Arg what have I got myself into?' By that evening, by the time I had got all my necessary errands out of the way, like cashing my cheque, I found myself spending an evening with mum being schooled in the art of walking. My first heels had been for show at the shop, mum had bought me some to learn in. Lower but still narrow heeled and a full court she called them. I was soon walking about the house with ease, even downstairs was not a problem, which was until she decided I should do the finishing school exercise of walking with a book on my head, which stopped me looking at my feet. Anyway the evening was fun and a chance to do something with mum for a change. There was also the make up lesson, where she put stuff on, then I tried to copy her. This stopped when I got cleanser in my eye and it would not stop watering, so we settled down with to watch TV with a glass of baileys and a chick flick so I could see women looking good. I had to admit I was having trouble imagining me looking like those actresses, but apparently I should aspire to that standard even if I fail I will still look good in trying. Then after a few more strong drinks we agreed a timetable. The next weekend I would get fully dressed. The weekend after I dress again and learn from any lessons of the week before. Then in three weeks we shall go out, somewhere quite so few people will be about, but it will be out. It was the baileys talking I guess because I agreed to all this and even considered if I could make it to the bank within a month when I would be cashing my next bonus cheque.
I was not sure who was the most excited about the upcoming weekend’s activities, but by the time Saturday came I was nervous as to what I was going to be asked to do, and this was merely a start. The first shock was to be told I needed to lose all my body hair and spent an age in the shower with a razor. Followed with a generous massaging of miosturiser into my skin which was very nice. Then make up and underwear 'Got you stockings because men prefer them, so I expect you will'. Then mum produced a plain fitted cream and gold cotton dress which she zipped up the back. I was amazed at how nice it felt, the high round neck and sleeveless style with just above the knee hem worked well. Just shoes, wig and some bracelets and a long necklace to finish me off she said and I was ready to have my first day at being a daughter.
By then it was lunch time and after we got a meal together we discussed what I should be called, she did not feel comfortable calling me Alex when in a dress she said, so after some discussion about names and things like what I would have been called if born a girl, and what do I like, we settled on a rather simple Alexis. Mum called that day Alexis's birthday, I just saw it as a step closer to my disguise, though I did privately admit that I felt unexpectedly comfortable in a dress. As planned I did not go out of the house that day, but I was not idle, there were plenty of things to be learned. Not just heels to adjust to, the dress needed constant monitoring it seemed to keep it right. There was the sitting detail, the standing up ritual straightening. Then added to this was how my arms and hands were held and moved. This was getting far more involved than I first thought, but it was fun and I still had that goal of being incognito every now and then.
I had nowhere special to go on Sunday so without much encouragement put on female underwear, mum's dressing gown and spent ages playing with mine and her cosmetics. I have say I preferred more muted colours to strong reds etc. and took time blending eye shadows so as to create definition without edges. Mum seemed pleased with my progress and sat beside me while she did her own face, which was unusual as she rarely wore make up besides lipstick and mascara. A nice female moment she said, while I just liked being near her.
The weekend over it was back to being Alex and work, uncle Dave asked how my weekend had been, I had no answer he would like, 'planning on robbing you' did not sound good nor did 'dressing as a woman' so I mumbled 'nothing much'.
I had a normal sort of week, plenty of work, going out a couple of times in the week to train with mates. What was not normal was mum asking how I was feeling about the prospect of being able to pass as a woman? I could think of 'Interesting' as a reply, maybe she was trying to see if my sexuality was being challenged or some such idea. I assured her I was just doing it to see what it was like. The saying about walking in someone else’s shoes came up, which made us smile, mum asked if I would like to try another style, I just said 'Why not' without considering the consequences.
Saturday morning came but I had some paperwork to catch up with so went to the office. Mum had been shopping and could not wait for me to get home it seemed. I was shooed to my room to strip off the Alex clothes and get into 'something more appropriate' before lunch. I put on bra, knickers and her dressing before appearing in the kitchen 'Well it's a start I suppose' was all she said. But once lunch was eaten I was sent straight back to finish off. I played with make up again, and brushed the wig into different styles, then once I was in the dress I asked her to zip me up. She did as requested then gave me a shoe box, I knew what to expect after our midweek conversation, cream sandals with a towering spike heel. I sat down to put them on, but needed to steady myself when I stood up, they really did affect how I stood and later how I walked. But before that I was given a lesson in the art of painting nails, mine were neatly clipped but not short, maybe needing a cut soon. So I was shown how to file from the sides and create a shape, then how to apply nail varnish. The smell was quite intoxicating and I was enjoying myself a little too much as my nails became a deeper shade of pink. Very nice mum said, very obvious I thought if it does not come off.
We had an afternoon at home doing some cleaning and for me a bit of sorting out in my room and checking up on e mails and blogs etc. Then nicely chilled out over the evening meal, mum asked how I was getting on with the new shoes, I said something like fine, to which she smiled and said good. The next thing I know is that I am being talked into the idea of going outside, the reason being that walking about the house is not like walking on a street where you keep on going, no short journeys like in the house where you take a few steps and then rest. I was clearly not comfortable, but she suggested a quiet area where it was all shops that would be closed at eight so very few people about, or even a car park, just somewhere to walk. I had clearly had more wine than mum as she drove us into town, parked and then spent ages coaxing me out of the car. Looking back I have no idea what I was worried about, there was no one about, the car park was empty, the shops closed, we saw two couples on their way to somewhere who did not even look at us. What I did notice was the cool breeze on my stockinged legs, how vulnerable I felt dressed that way. The high heels made their impact though, the click clack on the paving, the lack of easy footing when I stood on uneven slabs, and after what seemed like an age of window shopping the ache in my calves as my legs coped with the new footwear. Mum was pleased though, she said I had got the walking off to a tee, maybe a little more movement in my hips, and I must stop looking down. But overall a definite pass, very well done for my first time out. For some reason I even felt proud of this achievement and got in the car, bum first then swing the legs in. 'Perfect, not just a woman but a lady' mum commented. Then it was back home and a strong drink to settle my nerves and for mum think of where we should go for our proper mother and daughter outing.
I must have drunk quite a bit as when I woke I was disorientated, not only did my head ache and my mouth felt like cotton wool, my body was feeling odd, then as my senses returned I realised I was wearing a satin nightie and still had a filled bra giving me shape to my chest. I should have objected, got up and removed it, but the satin felt so smooth and comforting next to my skin that I lay there wrapped in its luxury and allowed myself to come round slowly. Eventually mum looked round the door to see if I was awake,
'Coffee'
'Please'
'Good night?'
'Different'
'You liked being Alexis'
'Pardon'
'Well you asked me for a nightie when we were getting ready for bed, so guessed you was liking it'
'Did I ask?'
'You did'
'Oh'
'I shall make that coffee........would you like the wrap that goes with that nightie?'
'Mum!'
Next thing she drops the satin wrap on the bed before leaving to make the coffee and shouting up that it is ready. Nothing for it but to put the wrap on and go and get my drink. So began another day of me in a dress and learning more about how to pretend to be a woman. I was not sure why but when I was removing the nail polish I felt a twinge of loss, maybe I was liking this more than I should, or maybe I was getting closer to my goal of going to the bank in disguise.
After getting me outside a week early, mum was full of ideas for where we should go the next weekend. Shopping maybe, to the pictures perhaps, out for a meal, just a walk in the park. Then there was the question of what to wear. I said the dress was nice, but was told I should always have a choice, look at her wardrobe it was full of varying colours, styles and textures. No, a woman does not need a man’s limited dress choice, therefore as Alexis I should embrace the opportunity. 'Oh gosh' was all I could think, I only need one outfit for what I want, but mum is enjoying herself, let's see what happens.
What happened was that on Saturday afternoon I am wearing some very non male trousers, they were black and covered my legs but that was about the only similarity. These were so soft to the touch, the belt was on my hips, and the crotch was very snug yet the legs were wide and loose, they also required heels to keep the hem off the floor. On my body I had what was best described as a pink mini dress, it had a bra shaped top then a flared part from below the bust which came to the top of my legs, maybe just maybe it could be worn as a dress. Mum had also bought me a jacket because she said we might not be so lucky with the weather and it might turn cooler. So once I was all changed and everything about me was feminine I plucked up the courage to leave the house sober. I need not have worried there was no one in the street looking and I was in the car and away. We decided that I should have a walk around with the late shoppers to make sure I was ok, then if that went well a Chinese buffet place we knew off, then the pictures and the anonymity of a dark theatre.
The walk was not much different to the previous week, except I had trousers on and there were more people about. We looked in a few windows, then while I was looking at something mum slipped away so she could watch how people reacted to me, did they stare or comment. She came back to tell me that no one had shown the slightest interest in me. I suppose I should have been relieved but at the same time I wanted to say 'Do you know how much effort all this has taken, take some time to notice me'. Then it was the Chinese, a pleasant Chinese girl showed us a table and how the meal worked, we ordered our drinks and were left alone to eat and chat. Again no one seemed to notice or be bothered with me. Then a walk to the cinema and while mum got the tickets I looked at the foyer on my own. I would need to go out on my own if I wanted to use the disguise so this seemed like a good way to start. That was until a bloke came up beside me and looked at the sweet choice in front of us 'I can never make my mind up. How about you?' He was talking to me, this was not in the plan. 'Oh I like the jelly babies' I tried to say in as soft a voice as possible. To my horror he continued to chat, asking what I had come to see, had I come far, then was I on my own. 'No I am with my mother' I very quickly answered wishing she would turn up right then. He moved on, then mum meet me at the till to pay for my munchies.
'He was nice'
'Who?'
'That bloke you were chatting to'
'Oh him'
'Yes him, good looking I thought'
'Did you? Frightened me to death'
'You looked to be doing really well, half expected you to link his arm and go and watch a film with him rather than me'
'Mother !' I tried to say quietly.
'I think we shall have to do some voice coaching, don't you?'
I turned to pay the girl, 'Thank you, ignore my mother please'
Then mum linked my arm in a way I saw girls doing and guided me to the screen we were going to watch.
On the way home, before we got to the car, mum managed to get me into a pub for a drink, I asked for lager and got a small stemmed glass, I took it as being taken for a woman, as Alex I would have expected a straight side pint glass, so some recognition for my effort I commented to mum later. To which I was told, 'Women rarely get praised for looking good, so why should I expect to be any different, no comment is good. Besides the bloke at the sweet counter took you for a woman, virtually asked you out I think' I had to stop her there and talk about something else.
Sunday was a relaxing day with nothing much to do but wait for Monday. Only this time I spent the first half the day in my borrowed nightwear and the second half cleaning myself up for being Alex the next day.
This week was the week I did the cheques and I had made my preparation with fake invoices so I duly paid out all those accounts that needed paying, which just happened to include a few hundred pounds for me. I had put away over a thousand in a few months by this stage and wondered if I would be up for going to a bank on Saturday morning as Alexis. Mum was still telling how much fun our Saturday night had been, it was such a buzz she kept on saying, so it was not hard to make up a story about wanting to find out what it would be like to go out on a Saturday morning and do regular stuff, but as Alexis. she thought it a great idea and wanted to know what I had planned. Bit of food shopping, going to the bank. that sort of thing I suggested. I wanted to say on my own but she looked deflated when I talked and besides I felt it would give me a safety line if I got into trouble if she was about.
I was up early on Saturday knowing it would not be my usual quick up and dressed routine. I was right, it was ten before we left the house, me in the trousers again and feeling a little more confident than previous trips. We went round the supermarket together while I got used to being with so many people. Then I suggested I go off on my own, she did not stop me and I was soon turning my cheque into cash and realising that I should really have a handbag and a purse, women do not use jacket pockets for anything but tissues. When I meet up with mum again I mentioned this and she said it had crossed her mind also. So for the first time since my embarrassing early visits to ladies shops I was looking at something a bloke should not be buying for themselves. I came away with a nice black shoulder bag, a pink purse and a rainbow coloured umbrella that would fold up into the bag. It felt quite odd having a bag at my side, but was just one more thing that affected my movement and my image as a woman.
Something else that affected how I saw myself was how mum managed to get me from quite basic items such as the purse into the more frivolous items, such as nightwear. I tried to tell her I did not need anything new but she pointed out how many times I had borrowed hers and it was time I had my own. I was blushing under my foundation and blusher, but she knew I was cornered. I returned to the car with carrier bags containing, one long satin cerise nightie with lace shoulder straps, one cerise full length dressing gown and one pair of white slippers. All because mum thought I should like to have them. This was not in my plan when working out the disguise.
With the money safely tucked away in the bottom of a drawer I felt that I should calm the dressing up down. I said that I needed to meet up with some friends on the Sunday and managed to curtail mum's plans for another night out, saying I was tired, which after a day like I had just had was possibly true. Anyway Alexis went dormant for a few weeks, I had things to do of a weekend besides indulge mum's desire for a daughter I argued with myself, I went back to sleeping naked and got on with being Alex. Mum did from time to time let me know how much fun she had from being out with Alexis, so after a month I relented and promised her a girls weekend, fortunately this coincided with my monthly cheque cashing trip, which could now be done in disguise as planned.
Mum made sure I was fully prepared and made me have a full shave on the Friday night, then once we had done the food shop, I went off on my own again to the bank, telling her I wanted to experience going solo. Then with my cash in my pink purse I rejoined her as she came out of a clothes store 'come in here, this will look great on you Alexis' I followed her only to be shown a black dress, I guessed lycra with lace detailing.
I pulled at it showing how stretchy it was 'will show every bump if get what I mean'
'That is why you could buy a pair of these as well'
On another stand were some big panties, and made of stronger stuff than regular ones.
'They will hold everything in place, smooth the bumps out'
I just looked at her, 'And when would I wear it, hardly a shopping dress is it?'
'No but for going out of an evening maybe'
'Like when do I go out?'
'Like this evening if you want'
'Mum, what are you planning?'I just fancy going out for a meal with my favourite daughter, maybe the flicks again?'
'Ok just this once, how much was it?'
That was not it though, I needed some black stockings and a pair of shoes, plus another jacket, the brown one would never do. Apparently. And so after a rest at home we got ready to go out, went to a proper restaurant this time, then onto the pictures and another chick flick. As we sat at home later on I reflected on how, if a woman was wearing my outfit I would probably find myself staring at her. Mum just pointed out how unobservant I was as there been more than one bloke taking a second look at me. 'Wow' I thought 'I never had me down as sexy, just imagine if they knew the truth' and smiled to myself.
Soon my life had fallen into a routine, most of the time I was Alex, but the first Saturday of the month I was Alexis. I made my visit to the bank and spent the day with mum dressing up and going out mostly. After about six months it dawned on me I could open an account as A Smith without the gender part, so that is what I did which allowed me to use my cards as Alexis or Alex, no one ever knew whether it should be Mr or Miss and no one cared. I even opened an account with Alexis in mind, but I had to show ID so I settled for the initial and started to deposit my cash into the account so it stayed separate from Alex.
Things were going fine, my monthly outing as Alexis was enough for me and possibly enough fun for mum, though she did try and get me into new situations from time to time. One time we went to the city clubs and danced the night away. Another time she took me to a football match to see how men reacted to women in a macho arena. Several time she took me shopping and eventually got me to go into the cubicles and try items on, even coming to the entrance to let her see me, that was so nerve wracking you would not believe how nervous you can get when stripped and thinking someone is going to call out 'There is a man in here'. In my opinion it is worse than the ladies toilets, at least you can lock the door there which is better than just a flimsy curtain to protect you.
Then after eighteen months the housing bubble burst, my uncles were hit but not as badly as some, they picked up smaller jobs and let the casual workers go just keeping the core tradesmen on, but it was tighter on the money and the cars got traded for cheaper to run models, and their holidays stopped. Things were tough but still solvent, I did my bit and stopped taking my own bonus, I had by this time deposited a few thousand into my account and was thinking I might soon afford a house of my own.
After what had been some very hard months, the cash flow was getting better and work was picking up once more, the brothers relaxed a little and even took a short holiday. It was then I decided I would restart my bonuses, I do not know what I did wrong but after my third cheque was cleared I came into the office one Monday morning to find my uncles looking serious. The computer was on and several files were out.
'You do keep the office very well organised Alex, it is so easy to find stuff these days'
I felt the blood drain from my body, it was not what he said it was the way he said it.
'I mean you can put your hand on any invoice you want cant you, like this one for example' he had one of my fakes on the desk.
'Now we are puzzled why Arkwright’s have sent more invoices than are on the statement, and yet you always paid them all, the extra one being paid separately it seemed'
I was thinking how bad could this get. I felt like a being a small boy in front of the headmaster again. 'I think I can explain' I mumbled.
'Well maybe you can explain this as well' the other brother opened an envelope and scattered some photos on the desk. There was a woman leaving my front door, that same woman got into my car, then the same woman went into a bank I knew only too well.
'I ......errrr.......think it was time I was going' I was feeling like my knees would buckle under me, I needed to get away before they went.
'Sit down Alex, I can see this is a bit of a shock to you'
I sat on the spare chair. Now we have no idea how long you have been putting your hand in our till, but we are pretty sure that the last cheque you made out to Arkwright’s never went to them, but the lady in these photos cashed a cheque for the same amount a couple of weekends back, it cleared on Thursday I believe.'
I felt a little courage return, 'I was only doing it to help mum, I thought this was a family business but we were getting none of the rewards, and you were of in flash cars and tropical holidays'
'Don't bring our Susan into this, we have had chat just now and she knows nothing except that she knows you like to be Alexis from time to time'
A tear escaped from the corner of my eye.
'Just perfect Dave, soft just like his dad'
I got up to leave thinking I would be not welcome anymore.
'Where do you think you are going? We think you owe us some money and maybe more of an explanation'
'What's the point, you will sack me, I will just go'
'Not that easy, you have broken the law, the police should be informed, you should be taken to court, be given a criminal record. Should he not John?'
'Off course he should Dave'
'But he was very good at keeping this all neat and tidy, be a shame to waste that and have to find someone new'
I knew they were playing with me like a cat with a mouse.
'Be a shame to lose her wouldn't it, but there has to be some punishment, we need to know she would not do something like this again'
'We would? Any ideas love?'
I found my voice 'Please I admit it was me, it was not a lot just a little every now and then'
'Well there we are a confession. Maybe we should delay the police, but I would like some sort of retribution'
'Please what do you want?'
'What was it your mum your said your name was?'
'Alex'
'No we know that, I mean when you go out in a dress?'
'Alexis' I said quietly.
'Well Alexis, you have a choice, either we call the police, or you come into work tomorrow all bright and breezy as Alexis. Your call'
Then Dave added, 'You can call Susan if you want, but you have until we finish our brew to decide. If you run away or don't find us we will call the police. Got it?'
I swallowed hard, 'Yes' came out as a squeak.
Shattered I sat there and cried. Then I phoned mum. She was not surprised by their reaction after their unexpected call earlier. But she plainly said if I have stolen then I had to face the consequences. All I could say was but everyone will know. She just told me I could be teased at work and face the humiliation or end up in court.
The phone rang 'you there Alexis?'
'Yes, Dave, I am here'
The next thing was they were back in my office.
'Decided?'
'Yes'
'Well come let us in on it'
'I' I gulped 'shall come into work tomorrow'
'As Alexis?'
'Yes as Alexis'
'Right well then we have a few rules, don't we Dave' he looked at his brother 'You will wear skirts and high heels, and we mean proper heels. Nice make up, pretty as you can. And we have one treat for you. Remember that row of shops we refurbished a few months back'
'Yees'
'Well as you know Sadie has not quite paid us for all the work has she. And seeing as how her shop is a salon we have done a sort of deal with her.'
'I am so sorry'
'Enough time to be sorry later, right now Sadie is expecting you and has been told to do whatever she feels will help improve our Alexis's looks'
'But there is no need I can sort myself out'
'Now where would the good in that be, you could switch back to being Alex whenever you want, no we want to know that the little thief Alex is gone and our lovely niece Alexis is going to be around for a while' They were both grinning as I started crying again 'Just like a girl, I think we are doing you a favour. Very soon your looks will match your personality'
One last time I pleaded 'Please'
'Oh and to show we are not heartless, leave the truck you can have the little Citroá«n from now on. Now off you go'
They left me alone as I felt my blood coming back to me. I could still leave and face the police. Then the phone rang, it was mum.
'You going to Sadie’s?'
'Oh mum I don't know'
'well put it this way, if you come back here without going to Sadie's first, my brothers will inform the police and this would be the first place they will look'
It dawned on me that to run away would mean leaving mum at least for several months, and where would I go, my money would not last too long, I would be alone. This was torture having to decide between mum and being Alexis.
Then she broke my thoughts 'I did like having Alexis around, and I think you liked it as well'
'But not this way. I was only doing it to see if I could, I am really a man. Aren't I?'
'Why do you think they are doing this to you, they are going to enjoy watching you squirm or be prosecuted. Your choice, hope to see you later. Love you'
I looked at the little car's keys on the desk and just thought 'Right, let's get on with it' I drove out of the yard without a word and made straight for the salon before my resolve could snap.
The shop was empty except for two women.
'Hello, I'm Sadie, this is Lucy, you must be Alexis'
I blushed as I said 'Yes'
'Right then Alexis, I need to make a call and Lucy would you help Alexis into a robe'
As I went into a back room I heard Sadie on the phone saying 'Yes I suppose I should say she is here' then a pause while she listened 'See you later'
I dreaded to think what these two women would do to me, but I was not comforted with Sadie's words 'Well then Alex....is, it seems we have carte blanche to do what we fancy. The only condition is that you look like a woman when you leave and that it will be difficult if not impossible to look like a man anytime soon' My heart was sinking as I braced myself for my treatments. 'What have you done to piss them off then, and why will you let us do this to you?'
We had plenty of time to talk, I explained how I had been caught taking money and how I had pretended to be a woman when I went to the bank thinking it would help cover the trail. She was intrigued that mum had helped me in my feminisation and asked if I thought she wanted a daughter rather than a son. I resignedly told her if that was true she would be getting her wish. Sadie told me something of why she was having trouble paying off her debt and I tried to be sympathetic but I was not really in the right frame of mind for that, I was staring at the worst case of humiliation and embarrassment imaginable.
Sometime around lunch Dave turned up with a bag of what I was told were clothes he had picked up from my room, I dreaded to think what he might choose, but until Sadie was ready I would not find out what I had to go home in. About four I was finished. I shall start at the floor so I hopefully don't miss anything that had been done to me.
My toes had been painted a colour called pretty pink.
My legs along with the rest of my body had been waxed and soothed with a bronzing cream.
My hands had long nails attached and painted a matching pink, I was already aware this would affect my grip and touch but was not truly ready from how much.
The most changes happened to my head. I had extensions added to my rather long for a boy cut, then it was coloured a similar dark blonde to the wig I had been using, but with silver and gold highlights. Giving me a long ruler straight style which went to well past my shoulders the fringe clipped to one side as it swept across and down the side.
I also had extensions added to my eyelashes which felt really weird as I could see them at the edge of my vision. My eyebrows were waxed into a thin line. My ears sported a hoop and stud in each lobe, as well as a small stud in the side if my nostril. Then though I did not realise it at the time the make up had a dye in it so it was semi permanent. My lips would have to be pink or darker for at least a week I was told the day after, the same went for the eye liner. I was truly stuck looking like a woman and if I failed to turn up for work I would have to now face the police looking this way. The final thing was to get dressed, I blushed when Sadie and Lucy asked if the clothes were mine, there was a set of white satin undies, bra, panties and suspender. Tan stockings. A white silk blouse. A flower pattern pleated skirt. The cream sandals. My brown jacket. And a brown shoulder bag. Before I could dress Lucy checked the bra size and brought out a box which contained some very realistic tits. Which I very soon found out were to be stuck to my chest in way that would make me look well endowed.
Lucy and Sadie both told me I would have no trouble passing as a woman, if that was any comfort. not really I told them, but thanked them all the same. Lucy hugged me and offered her best wishes. When I asked for my other clothes I was just told Dave had taken them. This should have warned me for what I would find at home. It was a challenging drive home, a new car, heels and not sure where I was going made it quite stressful, but eventually I was parked outside my home. I had never done this on a weekday at the busiest time. Nothing for it, I got out and went for the door. Mum was in and waiting for me.
'Oh. Wow. You look fantastic. Come here.' We hugged and I felt myself relax. 'So you did it'
'Clearly'
'I'm pleased, would have hated if you had done a runner.'
'Best of two horrid options really'
'Don't be like that, you look great, I get to have Alexis all the time, or at least for a few weeks I guess. You keep your job. The police aren't involved'
'But I will have to face everyone at work tomorrow. It will be dreadful looking like this'
'Rise above it and just ignore anything unless it is to do with work'
I changed the subject 'What is for tea?'
'Stew'
'Smells good'
'Come on lets have drink and settle down.....Alexis'
'Yes it is Alexis. I'm so sorry, it is all my fault'
'Forget it, this is how it is at least for this week, so get used to it' and she gave me hug before going to serve up the tea.
Over the meal we discussed what I should wear the next day. A suit I had bought many months ago but like all my clothes, hardly worn, seemed favourite, the tight skirt would be easier to manage, and the jacket could keep me warm if it was cool. Slowly mum also got the details of my time at the salon. She gave me tips on how to handle long nails, and looked carefully as I mentioned one or two of the things done to me, but what was hard was that she seemed positive about everything, making comments like 'It is pretty' (the nose stud) 'Long hair suits you' 'Those nails look so elegant' and 'I shall get you some nice ear rings for when the holes heal', I was not sure if she did secretly want this or if she was trying to be positive and look on the bright side.
It was late when I finally went up to my room. There was another frightening truth about my situation waiting for me, my room had been robbed of every piece of clothing I might have worn as Alex, all that was left were the few items I had acquired over the past eighteen months. There was no knowing where my stuff was, what very obvious I would not be having any Alex time, I would be dressing as a woman fulltime. That had been made very clear.
That night I slept in a nightie for the first time in months, the reason I told myself was to cover up the silicone attachments to my chest, but I still liked the feel of satin but I was not admitting to that just then. Somehow I was determined to hang onto my masculinity no matter how well hidden it was.
My first day at work as Alexis was every bit as horrid as I feared. I had been dragged out of bed by mum who just told I had to go through with it, get it over with, were her words. I had to sort out very much longer hair, make up, dress and get some toast before leaving in my little hatchback. As I drove into the yard I could feel a few eyes watching me, then I took a few deep breaths before opening the door and they could have a full view of me in my dark grey suit, white blouse and black heels. Stepping out the car I focused on where I am going, miss the puddles, into the office, shut the door, and relax. I was in and out of sight, the relief was immense. I was wiping the mud of my shoes, something I never did as Alex, but heels never look right dirty, that was when the door opened. Dave walked in, a moment later his brother. 'Good to see you Alexis, nothing much has changed except you can no longer sign cheques which you must have expected.'
'I am impressed' said John 'You are actually very pretty, we did not believe the photos at first, but now, well let's say, if I did not know then I would never guess'
'Please don't make this any harder than it already is, I feel so ashamed'
'And so you should, maybe embarrassed, humiliated as well?'
'Yes and a few more'
'Good that is the point, we don't like being take for mugs'
I ventured a question 'For how long?'
'Well that depends on a few things, good behaviour, showing remorse etc'
'I have said I am sorry'
'We know and have taken that into consideration'
'How long?'
'Well the courts would have given you over a year probably, there was someone a few weeks ago got three years'
My blood was leaving me again.
'So we thought eighteen months, knock a couple off for you confessing, then if you behave and do a good job a few more months.'
I had hoped for a few weeks maybe a month.
'Let us say a year if you are a good girl'
'Dave, John, please this is so humiliating please ..... a full year, what about my mates my sport, my life will be ruined'
'Well you should have thought about that before you helped yourself to our cash. You can always call the police if you don't like our justice'
'Please'
'Right Dave I think we are done here, I am off to the bank, you still seeing the solicitors'
'Please, no, I shall do it' I fear I sounded a little hysterical at that time.
'Sorry Alexis, that was nothing to do with you, we are buying some land, which is why we are seeing these folk. But it is nice to know you accept the punishment.'
I did not get much work done, no matter how hard I tried I would be interrupted by anyone who wanted to come and take a look under the pretence of asking for something or giving me something. I was ready for this and had my answers ready. 'Yes, what can I do for you?' 'Can I help you?' phrases worked well and I just avoided personal questions or comments. It was possibly the most stressful day of my life. Nearly all the staff came in to grope, but news soon spreads and delivery drivers were soon coming in on spurious errands.
Eventually five o'clock came round and I could escape home. Mum was sympathetic once more and asked how it had gone. I told her it had been terrible, but she did not look shocked when I told her I was expected to stay as Alexis for a year. Her response was to say I was getting of lightly compared to prison which could have been a lot longer.
The next day was much the same, just less interested visitors wanting to see the latest attraction. I got back into the work and tried to forget myself and concentrate on what I was doing. How I was dressed did not affect who I was, did it? But the skirt, heels, nails and long hair were constant reminders that I had dressed in more comfortable clothes a week before.
Slowly my freak status faded, by the end of the first week I was able to get on with my job pretty much without being too embarrassed by unnecessary visitors or unhelpful remarks. I was also fed up with wearing the same suit all week, even if I did get to wear all the blouses and tops that went with it. So on the Saturday afternoon I did my first really girlie thing. I went shopping not because I needed to replace something, but because I wanted to get something nice to wear. I had to dip into my savings as I spent so much. A navy suit, three tops, navy boots, a green dress and jacket with matching heels. Some blue and green costume jewelry at my mum's prompting 'Might as well do this properly' she offered, 'They might know the truth at the yard, but outside why attract attention to yourself by not looking the part.' I could see her logic and agreed to look as feminine as possible, which meant more handbags, a couple of scarves and a three quarter rain coat.
Monday, Dave commented on the new suit and I told him I had been shopping, he smiled and suggested I was liking the situation more than I should. I informed him that he was wrong, I just needed clothes appropriate for the situation and if I was going to be this way for a year then I would need more than one outfit, even Jerry the labourer has three pairs of jeans. He just smiled and said 'whatever you say Alexis. Can you get me the bank statement for last month' and that was it back to work.
It was during this second week that Pete a less macho member of the staff came in to drop off some notes, lingered then said 'Why did you start wearing a skirt?'
'I don't want to talk about it'
'Only the gossips can't make up their minds between you being one of those transsexuals or you have upset the bosses and this is their way of getting back at you'
'What do you think Pete?'
'Well I did not have you down as anything but straight, that girl I saw you with in town was a cracker, on the other hand if this is what happens if you piss off Dave and John I will not be crossing them any time soon.'
'What can I say, we all know they don't like to be crossed, but who knows I might not have been as straight as you all thought.' I don't know why I did not admit to the stealing, Dave and John had made it clear they would not say anything I had to be the one who explained why I was going to be wearing a skirt, not them, which just made the situation a notch more difficult.
A month later and I had not totally accepted the situation, more resigned myself to the position, I had bought a few more tops and would change into trousers when I got home and weekends were trouser time as well, even jeans and loose sweats. Nearly everyone is treating me as person by this time, pretty much like before, if they had something for me they dropped it off or picked up what they needed. I was doing my job and how I dressed caused little comment most of the time, sometimes I might get a 'You look nice today' sort of thing, to which I would say as politely as possible 'Thank you', hopefully avoiding any innuendo.
I made a mistake though. I had to go in on a Saturday and decided I would be on my own so went in jeans and trainers. Maybe I thought I would not be seen or the weekends were my own time, I am not sure what I was thinking because the result was after couple of hours quietly getting on with the paperwork, Dave drove into the yard, something he rarely does on a weekend maybe he saw the gate open. Whatever he put his head round the door, said hello but I could tell he was not pleased. I found out how displeased when I got home at lunchtime. Dave was sat chatting with mum, his sister, there was an atmosphere and I soon found out what it was.
Dave started 'Sit down Alexis', I sat opposite them 'I want to take issue with how you are dressed. I thought you understood the rules, you are to be dressed as a woman all the time. From what I saw this morning I am thinking you are trying to look androgynous, which will not do'
'Many women wear what I am wearing'
'We are not talking most women, we are talking about Alexis and not wishing to cover old ground, you were to wear skirts and heels, no mistaking you were to look like a woman. Got it?'
'Yes, I shall bear it in mind, I just thought weekends were, well different'
'Not if you are in the office, and really the meaning was it was to be fulltime'
'Ok so I know now, I shall always wear a skirt when in the office'
'I have also had Sadie call me. Apparently you have not made an appointment to have your treatments freshened up.'
'I was going to get round to it soon'
'Soon is not good enough, she says the nails will need filling, the extensions need tightening even I can see your hair needs looking at, the long part is a shade lighter than the top.'
'I shall do it on Monday'
'You most certainly shall. But I am not sure you are taking this as seriously as we feel you should'
Mum was saying nothing and looking worried, which was not helping my confidence.
'Sorry Dave I do realise why I am dressing as you wish, and I will do what you say'
'That is good to hear, but' there was a pause 'you have been not a good girl and seem to be thinking you can get away with not keeping yourself looking female' he looked at mum 'Your mum I think is keeping out of this, but she is not saying no to what I am going to tell you now. On Monday you shall make an appointment with Sadie'
'OK' I confirmed
'You shall also contact this clinic' he pushed a card towards me 'and make an appointment'
I looked at the card, it was a clinic that did plastic surgery, the attractive woman on it made me think it was to enhance female attributes.
'And you shall ask them how soon they can fit you in for breast enhancement'
'What.........mum?' I was shocked.
'Your mum tells me the fake ones Sadie gave you are no longer stuck on, and from what I can see you are rather flat compared to yesterday. So I feel it will bring you back into line. You will not be able to have a boy chest, and I feel it is a good way to remind you that this is not to be an easy option. You are meant to look like a girl all the time, that was the deal, I will not be taken advantage off'
'Mum'
She spoke for the first time 'I know you won’t like it, but Dave does feel you are not doing this properly. I don't want to get involved but I can see both sides'
'So Alexis, Monday?'
'You really want me to have breast implants'
'Yes, and then I expect to see some cleavage, something a young woman is normally not shy about showing'
'Dave!'
'The reason for you being in this situation has not gone away, so stop whinging or else I will take that as not wishing to take your punishment.'
He got up and left without anyone saying another word.
Mum broke the silence he left 'Now you see why I don't have much to do with them, both bullies, used to getting their own way. I did try to warn you when they offered you the job, but I also hoped they had mellowed.' I looked at her thinking she was going to help me 'But you did steal off them, you did agree to this unusual punishment, and it was you who broke that agreement. I can see his point even if the reaction is a bit over the top.'
'But mum, breasts are not like hair that can be trimmed in twelve months'
'No but they can be removed. And besides I am getting to like having a daughter around all the time, a real bust would stop you being flat chested'
'So you want me to have a chest'
'Not really, but given the situation you will just have to get used to it my dear.'
I spent a weekend worrying about Monday and trying to think of some way that this latest event could be limited. I felt I had to appear willing but would ask for the smallest inserts, an A cup I thought should get round my fears. Anyway I ended up at Sadie’s on Tuesday having my hair done, nails filled and my eyebrows waxed. But it was the Friday appointment that was the hardest, a Dr Nichols asked me some questions to which I told him I was transsexual, could hardly admit that I was doing this because my uncles had told me too. Then he took some photos of my bare chest, looked at the silicones I had in my bra, and then took some measurements. And suggested a C cup, I said smaller would do, he told me I should think about it before dismissing his suggestion, and to come back the following week when he has my blood tests and photos done.
So a week later I was in his office once more, everything was ok, but he did think I should have a larger insert, I agreed to a B, then he told me there was a cancellation that week if I could make it. I rang Dave who told me the office would survive without me and I should accept. It all happened very quickly, one day I had a flat chest the next I have bandages and a sore ribcage. They looked huge but I thought it was the bandages and swelling. A week later I got see the new me, still bruised and a little sore, and still big. I asked the nurse if they would go down at all, 'A little' she told me. No way were they size B. Dr Nichols confirmed this the next time I saw him, turns out John has some sort of hold over him and when I asked for small, John was told and the result was I had been told to have a cleavage and this size would do that, not an A cup. A day later I was told everything was fine with the healing process and I should be ok to go back to work, and given some tablets to help with the pain and others to help the body deal with the breasts, which I was told I would need to take for several months maybe a year.
No one noticed the change in my chest size and if anyone asked where I had been, I just said I had been to see a doctor implying I was not well, which helped them understand why I was moving awkwardly. A rather nice side issue to come out of this was going and buying new bras, satin were soft and comfortable, so I ended up with several nice ones which if I had seen on a girl would have looked very nice, on me I was not so sure.
By the time I had clocked up three months as Alexis I had to admit that I was quite at ease with the situation, I felt no one took any notice of me at work anymore, people outside who did not know my past just took me for a woman which made life easier. The shower experience of washing my breasts was quite sensual at times, but for reasons that puzzled me I had stopped having erections and I was thinking of myself as Alexis the woman far more frequently, which was good as a manly bump was to be avoided at all times especially when out and about. And with winter coming I actually wanted to go shopping and look for something nice to keep me warm and look good. I got a nice blue wool skirt a bit below the knee to help ward off the draughts, a cream knitted top and my boots I felt was a good start. The skirt was not straight but I soon got used to having the wider hem and stopped getting it caught on things that seemed to just jump out and trap me in my crowded office.
I had also without prompting been back to see Sadie twice. The first time to get the nails filled and trimmed, I even got complimented on the quality of my own colouring which I was doing every week or when they got chipped. The second time was to have the extensions removed, they had gone frizzy as they do apparently, so I had a choice of redoing them or having my own hair styled. I asked for advice and they suggested that as my hair was well below my ears why not have a soft perm, this would bring the neck up and with long ear rings would look great. Not quite knowing what they were talking about I agreed. After what seemed like an age reading Cosmo magazines and having products put on my head I emerged with a wavy style parted at the right and being what mum called a short bob to me seemed quite nice, and like Sadie had suggested the hung ear rings below the bottom which looked good. It might not have been long but I liked it and felt sure it was feminine enough for Dave and John, if not I could always tell them it was Sadie's choice which should get me out of trouble. I was also beginning to see a change in my own attitudes. When I originally dressed in the unfounded hope that it would disguise my activities I wore clothes to look female, but when I looked for ear rings I felt I was making my choice so I not only looked female, but because they would make me feel feminine. I also found myself buying clothes not necessarily for need but to look good. As Alex I had a limited variety of work stuff, casual and best. As Alexis I had found myself buying something just because it looked nice without a specific thought as to when I might wear it. I also bought tops which fitted better, I had gone for loose fit, but with my third pay as Alexis I bought a blouse that virtually contoured around my chest so well the lace pattern on my bra was visible, I even thought it looked sexy and wondered how others would see it. Now that was shift of attitude.
It was at about the third month that those around me seemed to just accept me as Alexis. Most of my football mates were fair weather mates and never made contact when I stopped turning up. The gym was the same, people I thought were mates avoided me, except for a few. Mark who did football and the gym at first called and after meeting Alexis did not call for ages, but slowly a few texts 'How are you' became calls until he came to the house and after an awkward start we got chatting as if nothing had changed. It was Mark who persuaded me to go to a new gym as Alexis, pay per session, and just let them decide which changing room they directed me too. I went with a new set of kit which included a skort which was basically tight shorts with a short skirt on top, hopefully it would hide my extra bump. I paid and was given a woman's locker key and given instruction on what to do. Anything but the bike I reckoned, sitting on a narrow seat with my bits tucked between my legs could hurt. With the first session done I started to go a couple of times a week, I got trim again but I also got used to seeing naked women, I never showered in public for obvious reasons and would use a cubicle but plenty of women would undress in the communal areas and I got the full eyeful, what was different was that I never got a twitch from my little thingy, I knew I should find it a turn on, but I did not. It felt like when I had been in the showers as a man, I would look at the other blokes but only to compare how hairy, how muscled and how big the thingy, now in the women's I was doing the same, comparing their tits to mine, the skin tone and looking where the white lines were. I did wonder how I would react if I saw a naked man sometime around then, but dismissed it as silly.
Another friend to get over my new image was Pete from work, we had sometimes gone to gigs together after bumping into each other a couple of years before at the Apollo, but he had kept his distance until one day he dropped by the office to give me some paperwork. He also told me he had a spare ticket for a band I had not heard of, and asked if I wanted to go, 'with him' I asked, 'as mates' he confirmed. And so that weekend I went out for my first social outing since becoming Alexis, I wore a long turquoise maxi dress just in case I was being set up and did my make up better than work and meet Pete there. We had a great time as mates, like men and women can, I had done it before as Alex so why not as Alexis. I thanked Pete but was not sure how to, girls might have given me a cheek kiss in the past but that seemed inappropriate between me and Pete, so I bought him a drink and told him how much I appreciated what he had done.
So as December approached I had managed to escape the limits of my own nerves. I had been out with mum quite a bit, shopping mostly but meals and cinema like before, but I was also going to the gym on my own after a few times with Mark. And I had been to a couple of music gigs with Pete, pretty much like I we used to before I became Alexis. I even started to make friends with some women at the gym who did not know my past, and Pete passed me off as a new friend, no point making me a topic of conversation again was his logic, and it worked. I even enjoyed buying more kit for the gym, lycra was very flattering up top but looser around the bum was better, and there is so much colour choice, I soon had a nice collection.
This confidence I was finding when out in public was of help when Christmas came round. My gran always had us round for dinner, sometimes her sons would come as well, and this year she had everyone, no holidays or going to the in laws. She was not thick, my gran and knew her sons better than they knew themselves and cornered me to ask why I had let them push me into this. I asked how much she knew, which was clearly enough to know I had crossed them, she advised me not to let them push me around, I assured her I knew what I was doing and we had sorted out things and I knew how far they could push me. Which was a bit of a lie as they could have made my life even worse if they chose. But she did make a big thing of telling me how nice I looked in my turquoise maxi. My aunts were second wives and would be best described as trophy dolls, if the money ever stopped for clothes and stylists they would be off was the impression mum and I had. This was not dispelled by them telling me I looked fantastic and then suggesting I go to this salon or have this treatment, what was weird was they gave mum similar advice was I really such a girl in their eyes.
With winter came the need for warmer clothes, and a strengthening love of shopping, not just the practical warm jacket but knitted tops and lined skirts to help ward off the chilly draughts the office had. Trousers or legging would have been warmer but I was looking forward to the time I could wear them without repercussions so stuck with the skirts for the time being.
By six months I had changed quite a bit, slowly so I did not notice it myself, but I had changed. I was looking through my wardrobe one day and could not remember the last time I had worn a pair of trousers even on a Sunday about the house, nor could I remember the last time I had worn flats except for the gym, I always wore a heel. I also felt undressed if I had not put on at least the basics of make up, lipstick and mascara. Every time I went to Sadie's I would make the next appointment before leaving, be it manicure, waxing or hair, I would know when it was and more and more look forward to my time there.
I had also made a couple of friends at the gym, first it was chats while taking a recovery break, then a drink in the bar afterwards which made me feel like one of the women. This was far nicer than the time I went out with the women from the buttie shop where I would pick up lunch from, they knew my past and once invited me out, but I got a distinct feeling of being there as a curiosity not as an equal. To the women at the gym I was another female and that was nice.
Going out with Pete was nice as well, if we avoided the history I could just be me. We saw several bands and even went to the pictures twice, but it was as mates I had always thought, but a few clues should have alerted me. He nearly always told me I looked nice and once suggested I wore a brown top he thought looked great on me. The said top had a wide neck that revealed my bra straps and was a loose sheer fabric that allowed someone who took the time to see outline of the rest of the bra, and being white, when the strobe lights shone on me was virtually the only thing you could see. Then he asked if I fancied a weekend away at a festival, camping and music had been something I had done before so why not again. I said yes. Pete had a van that he cleared out of tools so we could sleep in the dry, so with a large hold-all full of clothes I went away for my first time as Alexis.
Friday night was good, got parked, found some food, listened to a band. Slept in sleeping bags on a hard floor.
Saturday we bought a blow up mattress then spent the day drinking by the van and discussing which bands we wanted to see, followed by food and going to see our selection. It was the drink that I blame for what happened. By five I had warmed up some stew we had and eaten it, then as we sat and had our last beer before setting off we sat closer than usual our bodies touching.
For no good reason I asked 'You don't have a problem with me being a girl do you?'
'Nope' pause and a deliberate look at me 'In fact you are much nicer to look at as a girl'
'Stop it' I told him. 'But you know the truth'
'And you are still one cracking bird'
'Really?'
'Yes really'
We might have been drunk but it was a great compliment. Later as we walked to the showground and the crowds got denser and I felt a few hands touching me in what might have been inappropriate places, I said something that made a big difference to the friendship 'Pete. Would you mind holding this birds hand so we don’t get separated' and just took his hand in mine, and he took it. I had meant it to be just while we were finding our way about but when we had found a place to see the stage from, for some reason we never let go. Then when a few songs came on that made you just want to dance around, we danced together. We got back to the van in the middle of the night, sat and reminisced over a coffee, sitting close again.
'Been a great time. Thanks for inviting me' I said
'No should be me thanking you for making the weekend special'
'Do you really think I look good?'
'Very'
'And you are not just being nice?'
'Not being nice, being honest, look Alexis I love having a pretty girl by my side, have you seen how some folk stare at you?'
'Yes I usually think they know the truth'
'They don't, they think how I do, I am so lucky to have you by my side'
'You think people think we are .... you know..... a couple'
'Why not'
'Well errrrr.....suppose you could be right'
'I am right'
Then things changed.
'Well then boyfriend, what should your girlfriend be doing'
He looked at me awkwardly.
So I continued 'Well I reckon most boyfriends would be hoping for a bit of action about now' and turned to face him, he was still looking at me as I put my lips on his. It was over a year since I had kissed anyone and it felt great to have that connection.
We broke 'Alexis'
'Yes'
'You sure about this?'
'It was you who said we made a couple' and it was Pete who restarted the kiss.
We kissed and cuddled for ages, then I felt his erection and put a hand on it and gave it a squeeze, he responded so I massaged it for a minute, he was so excited that was all it took for him to wet himself and collapse on his back.
'Bloody hell Alexis do you know what you have done?'
'I know what you have done'
'Ok not great control there, sorry'
'Nothing to be sorry about'
'Alexis can I ask you something'
'What?'
'Those breasts feel well......very real'
'Because they are, no way of being mistaken for a bloke with these up front is there'
'But thought it was just a padded bra'
'And now you know there is no padding how does that change anything?'
'Well.......this is serious, having surgery, and down below?'
'No still there, only one hole'
'Still they would look great in a bikini'
'Not sure if that is sexist or not, but if I ever get one I shall let you see them'
'Sounds good to me'
The talking stopped and we wriggled into our bags to keep warm, but in the night I woke to find myself wrapped in his arms, one had resting on my breast.
The Sunday besides being a hung-over experience was a quiet day. After tidying up and sobering up we made our way home. Nothing much was said and nothing at all about the night before. Pete dropped me at my home and said 'Goodbye, see you at work' and that was about it. Mum asked how it had been, saw that I had some tan lines, but I was not going to say 'Oh mum guess what I kissed a bloke and wanked him off' sex is not a topic that spans generations, and most certainly not between a fake girl and her mum. There it is again, I said 'her mum' not his mum. The longer I stayed as a girl the pretence was fading and I became more accustomed to being a woman that was not part of the plan for sure.
I saw Pete at work, but the banter had gone, we did not know how to talk anymore, the weekend had changed us from mates into something more intimate and we did not know how to handle it. On Friday Pete came in for his pay slip.
'We need to talk'
'About?' I enquired.
'Not here, tonight at the Duck'
'You buying?'
'I can do'
'I shall be there then'
I got home, showered and changed into the top he had said he liked (why did I choose that I later asked myself) and an animal print skirt. Mum asked where I was going, and gave me a knowing look when I told her it was Pete. He ordered two lagers and got served one pint glass and stemmed half pint, which must have been mine. Stereotyped or what I complained. To which Pete pointed out how unmasculine I was looking.
We talked or rather chatted awkwardly until I asked what he wanted to talk about.
'Last weekend'
'Yes'
'You enjoyed yourself didn't you?'
'I did thanks'
'All of it?'
'How do you mean?'
'The Saturday night?'
'The third band was great' I was teasing him
'They were, but later when we'
'Had coffee, yes I do like coffee thanks'
'Well that and the you know........after coffee'
'Oh you mean when we stopped just looking like boyfriend/girlfriend and got on with doing boy/girl stuff and you wet yourself?'
'Not quite how I would put it, but yes.......then. I am sorry if I upset you'
'What makes you think I am upset?'
'Being frosty with me'
'Not me being quiet, I thought it was you being all shy about how things turned out and regretted it'
We sat and looked at one another. Then I asked.
'Any regrets?'
'No, enjoyed the whole weekend. Are you upset?'
'Why should I be?'
'Well you know kissing and me loosing it'
'Is that not what you do with a woman then' god knows where this was coming from or going to I asked myself.
'It is what I like to do if I am with the right woman' he was squirming for no real reason other than he was trying hard not to offend me.
'And I am not a woman, is that it?'
He blushed and stammered 'Sorry'
'You seemed to like feeling my tits last weekend' he blushed more 'And was I not a cracking bird?' he took a big swallow of beer 'And yet you wonder if I was enjoying it'
'Sorry' he mumbled again
'Well for your information' I could not believe I said this 'the way you treated me last Saturday was a great compliment, you made me feel accepted as your girlfriend, not ashamed of me, happy to be be seen with me. And you coming was like the icing on the cake or do you come whenever anyone kisses you'
'Do you mean that?'
'I think so'
'Well do you fancy going out tomorrow?'
'OK. Where?'
'Go for meal in Didsbury'
'Sounds posh, trying to impress me?'
'If I can. Pick you up about seven'
The conversation turned to less controversial topics, but we sat closer and touched hands, and then in the car park as we parted he gave me a kiss, it felt like static through my body.
Saturday seemed an odd day, I went into the office, wore a suit with the shortest skirt and a blouse that looked good without the buttons fastened up to the neck showing some cleavage, and half hoped Pete would call in passing. But John stopped by for something, put a head round the door to check everything was ok and said 'Bleeding hell Alexis, you got a date or something later'
I was flustered by the comment as I realised how I had dressed without thinking how I looked 'I thought this was how you and Dave wanted me to dress'
'Well er yes, but you are usually more restrained'
'Sorry I shall wear a nun’s habit on Monday'
'Don't be cheeky, you know what I mean'
I thought about what he had said to me and by the evening had decided I would dress the part of a girlfriend who wanted to please her man. I wore a gold chemise top, with no bra, a pair of denim hot pants, brown tights, boots and plenty of gold jewelry, then a brown bomber style jacket to cover me up. Mum did ask what I was doing, so I told her going out for a meal, she warned me to be careful. Maybe she read into the clothes more than I was capable of, but it was odd in a nice way to be warned by mum.
The evening went great, Pete picked me up, he told me I looked great. Then when we got to the tapas bar and I took off my jacket, his eyes for a while never meet mine. I had never felt so lusted over in my life.
'Up here Pete' I said gaining eye contact.
'But you, they look fantastic, I err sorry'
'I think that was a compliment'
'Certainly is'
Then I felt my nipples harden against the soft fabric as it caressed the tips. 'Why is that happening', was all that went through my mind, 'I hope he has not noticed'.
We had a smashing time, nice food and some nice drinks, not all alcoholic, then back to the car holding hands. I loved the experience and told him so.
'Well if you don't want to go home yet, we could do some bar hopping or I could show you my flat'
'One bar then let's see'
We ended up back at his flat after it was clear Pete was quite randy. He made some pretense of showing me round and putting the kettle on. But before it boiled we were kissing.
We did make a coffee, but as we made it Pete asked.
'Those shorts are tight, where is the bits'
'Hidden'
'I guess that, but how?'
'Do you want to see?' and without waiting for an answer undid my shorts and rolled the tights down, leaving just a thong covering my pubic area.
'You must have cut it off'
'No still there just between my legs'
'But only one hole'
'Yes. If I had two would that alter things between us?'
I went over and kissed him 'Does mean I can't....you know what if we fancied'
'Oh Pete I thought I was more than a shag to you?'
'You are, I mean you are the first girl I have been with who I have not thought of in that way'
I put my hand down his trouser front 'In what way Pete?'
'Well I just like being with you'
'Nothing else?' his dick twitched and was damp on the tip.
'Alexis you are getting me to do things I .........owww......stop it'
'Why, you seem to like it' I was stroking my long nails up the length. 'Can't a girlfriend have some fun then?' I was enjoying the control over him and the pleasure I was giving him. 'Do you want me to stop?' He clamped his lips onto mine to stop me teasing him and slid a hand under my top to massage my once again erect nipples which felt so sensual and encouraged me to undo his pants so I could get my hand further round and cup his pulsing balls. It took about fifteen minutes before he exploded in my hand, his back to the cupboards and panting as his hands caressed my tits and arse. That had been so much fun.
'So mister who does not see me that way, how was that?' I asked as his erection wilted in my hand.
'Don't ask Alexis, this is so confusing'
'Being given a hand job by a girlfriend?'
'Well yes, I mean no, oh it is the one hole, two hole thing'
Then for an unknown reason I said 'Well then one day I shall have to let you take this virgins cherry'
'But I am not gay' He said
'Neither am I, well I did not like blokes before, but they do have an appeal right now' he blushed as I squeezed his sticky tip.
'I just see you and think woman, but at the back of my mind I know the sex would be.........wrong, well at least different'
'And I just see a bloke who has not shown any problem being a man and enjoying the delights of my body'
'Are you serious?'
'Maybe one day I would like to find out what it is like, but we would both have to want it'
I then withdrew my hand, zipped him up and went to wash my hand.
'Do I get a lift home?'
'Off course'
'I think it is time for me to go' I said as I got dressed.
In the morning mum asked if I had a good time, I said 'Yes' her reply.
'Thought so you were home late'
'Sorry'
'Don't be you need to get out and enjoy yourself, but do take off your heels before walking on the tiles in the kitchen'
'Sorry'
'Was he nice?'
'What makes you think it was a he?'
'Because of how you were dressed and I saw him knock on the door'
'Yes he is nice, treats me well'
'By that I assume you mean he treats you as a woman'
'He does'
'And you like that?'
'From Pete yes'
'You have stopped behaving like a man trying to be a girl you know'
'Have I?'
'Yes you have, you just do things without thinking now' I brushed a loose hair behind my ear 'like that'
'Like what?'
'See you don't even realise you are constantly preening yourself'
'Well what if I am'
'Well in a few months will you be able to stop'
'Off course I will, get myself straightened out and the extra stuff sorted out, be no problem' I smiled but for the first time I had to admit to myself I liked being Alexis.
'If you say so' she said with one of her knowing looks.
We agreed to not make anything public, but whenever we could we went out together, usually without me wanking him off, it was not all about sex, we went to see bands and for a few meals. I even invited him to meet mum one Sunday and cooked us a roast dinner. Mum accused me of showing him off, I said it was what girls do with boyfriends, to which I got a pointed 'Oh!'
My look even for work was changing. My hair had to be just right before I left the house, I was wearing more make up and would always have a full set of ear rings, necklace, watch, bracelets and rings on. I justified it by saying I was not going to let the brothers accuse me of not keeping to my part of the deal. It was a surprise when I went to Sadie's with about a month to go and asked her for a change of style, I had it permed before and wanted something straighter. I came out with an in curling bob the parting being held across with kirby clips that often had sparkly decoration or flowers on them. Mum asked me why, I said because I fancied a change. Dave asked the same but I told him it was so he did not catch me out so near the end of my year.
Pete knew nothing of the year punishment and I did wonder how I might break it to him that I was going to become a bloke soon. But in that last month I had a rather dramatic weekend. Mum went away for a weekend and so I asked Pete over on the Friday. He turned up once he had changed and I went into full girlie mode. Cooking a meal, watching his programmes, cuddling up to him. Then as it got late and we had drunk too much for him to drive I told him he could stop. He agreed and the next thing I know, I am changing for bed and putting on my favourite red satin nightie and asking him where he would like to sleep, while holding his hand and pushing my tongue down his throat. Without much help I undressed him and took him to bed. I knew I wanted to be his girlfriend one last time before I stopped being Alexis so I did not just wank him, this time I had decided to blow him. He was excited too, and was way beyond stopping me when I replaced my hand with my lips. I had read enough about gay sex by this time to know what I should do and slowly aroused him until he froze then jerked his load into my mouth. Once he had calmed down all I could hear was 'Thank you Alexis, that was great thank you'. We kissed and he got a taste of his own cum and asked if I liked it. I said it was different but not unpleasant. He made it clear he did not like the taste, to which I told him 'Good, I did not want him going gay on me and sucking another man's dick'
The Saturday following he had to work but by lunch was finished, we meet in town and went shopping. I bought him some nice snug boxers, he insisted he returned the gift and bought me a set of white underwear, including suspender belt. The tone for the rest of the day was set, we kissed and cuddled whenever we had chance. Then once home I changed my underwear and put on a fitted white silk blouse and short flared pink skirt. Then sauntered into the living room balanced on top of my highest heels.
'So Pete, will this do?'
'Well yes, but what are we doing?'
'Well I have your choice of virgin white on for you, maybe you would like take me somewhere and romance me?'
'Oh er, where would you like to go?'
'Or I could make it easy for you, I cook a meal, you go out and get something to drink and a dessert'
I was not sure what I wanted but he was out the door and down the supermarket quick enough. I had some pasta in a sauce well underway by the time he got back. Two bottles of fizzy wine and a chocolate pudding looked just right. We had a glass before the pasta was ready, then we sat and ate our meal as we finished the first bottle.
I was getting randy again 'So would you like to see if you approve of your purchases? I would like to see how well mine fit'
'Well I suppose so, but I know you will look good in them'
I stripped off the blouse and skirt, then in my underwear, stockings and heels went and sat on his knee 'Now I want you to seduce me, ok'
'More like you seducing me'
'Well catch up then'
I was undoing his shirt while he unfastened my bra. He had a very nice chest, lots of muscle and just enough hair. My bra came off. 'So what do you think?'
'I told you already. You look great'
'Have you got my gift on?'
'No'
'Well go and slip them on for me' he was up and in the bathroom changing in a moment. Coming back in just the boxers.
'Do you like them' he asked
'Very nice, shows off your assets very nicely'
It was then kissing and cuddling followed by some intimate touching. All a prelude to us going upstairs and us finding out if we could have any pleasure with only one hole. I have to say that with alcohol and lubricant, I relaxed enough to let him inside, and he got enough movement to enjoy pushing his prick into me, things were going fine until he touched something inside which was very sensitive, I tensed up and pulled his arse into me. 'Do that again' So he pushed in and touched that spot again. 'You just keep it there Pete, that is lovely' I could feel my nipples harden between his fingers. Then it happened, I came. My finger squeezing his arse pulling it to me, my lips clamped onto his neck and the exploding sensation that went through my body. He came as well, I know this because after he withdrew I could feel semen trickling out between my legs.
'That is what you wanted? I think' he asked.
'You will never know how good that was'
'I think I do, that was the best shag I have ever had'
'That is even better then' I was propped up against the bed head 'What now? lover boy'
'More wine, finish the pudding and see what happens'
I pulled a wrap around myself, Pete put his shirt and boxers back on while we ate and drank. Then we enjoyed each other’s bodies once more, this time falling asleep afterwards.
The morning was a shock to my system, I was almost used to sharing my bed after two nights, and I knew what a hangover was, but I was not used to the sore arse I had that morning. I managed to clean and shower myself, make myself presentable before I made Pete some breakfast, coffee and paracetomel. Then I needed to clean up before mum got home and all while Pete was trying to get me back into bed. I put him off with a promise of later. But mum came home and after I cooked us all a meal, Pete went home. I had barely said my goodbyes when mum asked 'I take you had a good weekend'
'Not bad thanks'
'Just the short skirt, the quick looks and rather long good bye, makes me think my girl has found new pleasures.'
'Mother!'
'And you are walking as though you have hurt yourself' I blushed. 'Did you like it?'
'Muum' I tried to sound offended.
'Well did you?'
'Yes' I tried to sound confident.
'Pleased for you'
'Mum. Do you mind?'
'Not at all, as long as you are happy with it'
'I think I am, but I am supposed to be giving all this dressing up in a few weeks'
'You don't have too'
'What stay as Alexis?'
'No one is stopping you'
'But what will people say?'
'How many know why you are dressing, not many know the real reason, most think it is your own choice'
'Oh dear this was not in the plan. What do you think I should do?'
'Well could you go back to being a weekend woman? could you empty your wardrobe and give it away to a charity shop? Could you tell Pete it was over?'
'Oh mum but I am a bloke under this' I gestured to my skirt.
'But are you a bloke in here' she put a finger on my chest where my heart might be, then gave me a hug. 'I know this was not supposed to happen but it has and you have to decide how you are going to handle it'
I had a rather sleepless night that Sunday. Work on Monday I hoped would be busy and stop my mind from confusing itself with conflicting thoughts. Pete came in and while no one was about asked if I was OK. I told him yes, then he invited me out on the following Friday to a music bar near his flat. Without thinking I accepted because I could not think of any good reason not to, just some vague feeling that I was sinking further into the girlfriend role and maybe now was a time to stop.
On Thursday I meet mum at the Trafford Centre shops, I thought if I bought some male clothes it would help get me back to thinking like a man. But again the plan did not work too well. One shop in particular made it hard, to get to the gents clothing we had to walk through a display of women's wear. I looked too long at shocking pink bikini, mum noticed.
As we looked through jeans, she suggested 'I don't think your heart is in this'
'It has to be' I answered 'I will need some trousers then, so I might as well get some'
'But that bikini, or was it the dress next to it,' a pause 'You can see yourself in them more easily'
I stopped looking for my size and walked out before I started crying. Mum was right behind me and as we sat on a bench 'It is alright to be confused, I am, and I am not the one making the decision.' She took a tissue out of her bag and offered it to me. I carefully dabbed at my eyes so as not to smudge my make up. ‘Now with honesty' mum said in a matter of fact voice 'Nightie or pajamas?' Boxers or knickers?' 'Satin or cotton?' there was pause between each question to let me consider my choice, but the last was different, 'Heels and stockings of trousers and trainers?' I looked down at my legs the plain stockings leading into my red sling backs looked so good, I had trouble thinking that one day I would cover my legs up and stop them looking so nice. Mum had made her point and we left empty handed for home. My return to Alex was going to be a hard on.
I then had to face up to Pete on the Friday evening, I was telling myself that we were just mates going to see a band and have a drink. I wore what I considered an appropriately casual slash neck top revealing my bra straps and short denim skirt. But Pete was not thinking mates when I meet him. He gave me a kiss then took my hand and lead me to the bar, then to a good spot in the room to chat and also hear the band. Then as we stood side by side and his hand came around my waist and pulled me towards him I knew I was in trouble, it felt so nice standing there beside him with his arm around me. It was twelve when we left and we had already had the discussion about my drinking and driving home, coming to the decision that I would be stopping at his the night, I knew this would be dangerous for my hopes to be Alex once more, but I argued with myself 'Just one last time'
Off course we made love, Pete wanted to more than me I think, and I once again loved the sensations. Then as I calmed down tried to compare it to a male orgasm and realised I could not because it was nearly a year since I had even had an erection never mind come. But even with old memories comparing to vivid new ones I had to say that being with Pete was the best. Then I tried a dangerous question.
'Pete. You know I am not a full woman, a man really'
'Not now Alexis'
'Sorry but this is important'
'Ok, yes I know are not quite the complete deal, so what?'
'Well I have been thinking. It has been a year of being Alexis and well I have to make a decision if I should stay this way'
He was wide awake 'What, go back to being a bloke? Why?'
'Well I had said a year to see if it was right for me' I lied using stuff I had read about transitioning to support the lie 'and that year is up'
'But the tits, the hair, just look at yourself Alexis'
Then the hardest question 'Pete would you still want me if these' I cupped my bust 'were flat?'
He threw himself onto the pillow and stared at the ceiling 'Fuck me Alexis I thought it was you who wanted this, I love being with you, yes there would be problems if it got out at work, but up until a few minutes ago I thought you were happy with how we are'
I then started crying 'Sorry. I just get so confused at times'
He sat up and held me tight, then brought the conversation to an end 'Maybe this will end your confusion. Alexis I fancy you something rotten, I think about you all the time, I love making love to you' then a deep breath 'And if you went back to being Alex then I would be confused, and almost certainly would not want to see you ever again' The silence that followed could be cut with a knife and could be weighed it was so heavy. But I knew where he stood at least.
The morning was subdued as I left to collect my car, Pete could see I was troubled and left me to my thoughts. When I got home I googled the name of the drugs I was taking to help my body adjust to having breast implants and made a shocking discovery. I had been taking hormone blockers, no wonder I had not had an erection my male hormones had been stopped, I called mum and told her, she was equally shocked and as we read more and more about these pills, the more we understood some of why I had responded like I did. The worst part was to read that a common result of continued use was a permanent reduction in hormone production. Six months was considered a long time, so twelve must have done something to me.
Mum rang the clinic straight away but Dr Nicholls was not in, she told whoever answered that she was going to sue him for malpractice and a word might be useful before it got all legal. She was thinking he was a pawn and just wanted the truth. A nervous Dr Nicholls called back later. We had found out he had been struck off in other countries but not in UK, so when he rang mum was ready with information to embarrass him, but she wanted to know the truth. Which was that the brothers had come to him with the request to give me breasts, he tried to say he objected but we did not believe him, and the drugs we asked, the brothers wanted something that would make me less likely to want to be a man, he had some of these pills spare, and I was only meant to take them for a bit, not a year. 'Well you should have made that clear' was my exasperated reply. Mum was enjoying playing with this man as he went on to explain how I could take other drugs which might replace what I was not producing, she was talking of suing him, contacting his professional body. All the time I am thinking this is terrible as he offered to do anything we asked.
I was crying when mum put the phone down on a very worried doctor. She hugged me and comforted me for ages.
'My brothers have slipped up big time' she said later 'I think this could be fun. But first you need to make a decision. Alex or Alexis?'
Still upset I said 'No choice is there, you seem to want Alexis, Pete wants Alexis and even if I didn't and wanted to be Alex I could never be a fully functioning man, no woman wants a limp dick do they?'
I went off for a long hot bath to try and soak away my problems, while unknown to me mum was planning a little revenge of her own.
At the end of that week Dave and John came into the office. 'Well that is the end of your year Alexis.' I looked up at them 'I do hope you have learnt some lessons about not messing with us' Dave said.
'Oh yes I have learnt an awful lot about many things. Is this the official release date as it were?'
'Yes it is, twelve months near enough'
'And I can come in trousers next week?'
'Yes'
'And what do I do with these?' I put my hands under my bra and lifted the bust up making the blouse gape even more.
'I am sure Dr Nicholls will sort that out, half expected you to have made arrangements already'
I was feeling confident and dismissed them 'Thank you, but I have work that needs doing if you don't mind'
Monday morning was very different, for one thing I was hyped up with anticipation. It had taken me an age to get ready even with mum keeping me calm. At eight o'clock I walked into the main office to find Dave and John. I had their full attention as I stood before them in my trousers, not the ones they had dropped off at the weekend when they returned my Alex clothes, but a new suit I had bought for the occasion. It was black with pink pin stripes, the trousers hugged my arse but by the time they had reached my patent black 4" courts they were possibly 20" around the hem. my pink knitted top had a V that came so low down I had to be careful not to show my bra, the jacket a well fitted short one with a small stand up collar finishing off my outfit. Sadie had done a fantastic job on my hair, I once again had extensions that came well down my back, this time with a wave to it.
'Good morning' I started, they were looking at me gobsmacked.
Dave finally managed 'Why?'
'Why not?' I came back.
'Well the sentence has been done, you can go back to Alex now'
'But can I? Is it that simple?'
'Well besides the tits we thought it should be'
'You have no idea how much trouble you are in do you?' Their faces looked worried 'Besides the physiological damage you have done to me, the effect of these' I opened my jacket for dramatic effect 'has made for serious problems as far as you are concerned' I waited for them to consider what I had said 'Dr Nicholls. Your friendly doctor, should have been banned from working here. The drugs you asked him to give me. It is virtually impossible for me to be a father now' this might not have been true but sounded good 'you against my will have turned me into a woman'
A rather lame 'But you agreed to it at the time' was soon shot down.
'I would love to see you say that before a judge'
There was silence, then a knock at the door, 'Not now' was barked at whoever was on the other side.
'I think I hold all the cards at the moment, now as you put it a year ago, we can sort this out here or go to the police, well lawyer actually.'
'What do you have in mind, you seem to have planned this pantomime so far'
'I want you to give me and mum a pair of those semis you are building at the moment, one each. I also need a rise. And I shall want you to sort out my legal situation so I can honestly be called a Ms'
'But those houses are expensive'
'You have cost me an awful lot, what I am suggesting I think is nowhere near the damages a court would hand out. I shall leave you to talk things over' Then turned on my heels and walked out of the door.
'Alexis, you alright?' Doreen the secretary asked, I guess it was she who had knocked.
'I'm fine thanks'
'Just it sounded rather heated'
'Not me, they might need leaving alone for a bit though'. And I went off to my own office to get on with my own work. I rang mum and told what I had done, she knew it as we had gone over the situation many times rehearsing it together. She praised me and told me to stick to the plan and not give an inch, they dare not go to court with their backgrounds.
Over the course of the day there were phone calls between the brothers and their sister, then polite offers but less than I was asking for. Then at five just before I was going to leave I was asked to meet them in their office, Mr Lawton was there, the solicitor who handled the legal part of the sales with a puzzled and amused look on his face.
'Alexis, come in, sit down' he was pleasant enough, I sat down, crossed my legs and rested my hands in my lap.
'Nice to see you Mr Lawton, what can I do for you?'
'This is most interesting Alexis, I have been asked to transfer the deeds of some properties to you and your mother'
'That would be really nice' I said with a smile on my face.
'And I can only guess at what is going on and no one is being very forthcoming about it, but I have also been asked to look into changing your name and legal status. Is that correct?'
'I do suppose you know something of my past?'
'Most interesting situation if you don't mind me saying'
'And I guess that you do not know why I am dressed like this?'
'Many people have made guesses, I took it to be a personal choice'
'Well let's say it was not a free choice and now it appears I have no choice' a look at the silent brothers and I thought about how much I should say. 'So it would make life easier if I was legally sorted to match the person you see'
'I understand that but the why is still a mystery'
Dave spoke up 'I think that is everything'
'Indeed it does seem to be' said the solicitor. I got up to leave with Mr Lawton who walked with me into the yard. 'Never seen them so subdued, unusually they are not in full control I am guessing, and something to do with you being Alexis is the key'
'It could well be Mr Lawton, thank you for your time, I look forward to seeing you soon'
As soon as I was in the car I rang mum and told her. Then I rang Pete and told I had to see him right away. I was so excited I just wanted to do something completely rash. I told him to be at my house. By the time it took me to get there, he was parked outside waiting. We meet at the door where I kissed him in full view of any watching nieghbours, then I pulled him into the house and upstairs, where I started to undress him, and let him undress me. It did not take long for me to be on my back with Pete between my legs and me asking him to push harder.
'Oh I needed that' I told him when I relaxed. 'What a day I have had, you would not believe it'
'I take it you are not thinking of changing then?'
'Nope, soon I hope to be a Miss, would you like that?'
'Miss Alexis Smith, sounds good'
Then the front door shut. Mum was home. I pulled a satin dressing gown around me as I got up. Pete struggled to get his work trousers back on. I walked downstairs to find mum in the kitchen. She looked me up and down. 'I see you have been celebrating. Went well today then'
'It did, didn't it'
'Everything went to plan, and a little more besides'
'It was fantastic, they looked like little boys in trouble.'
Then Pete walked in 'Who was in trouble?'
'Hi Pete' mum said 'you here to celebrate with her?'
'Already been doing some celebrating haven’t we' I looked at Pete then kissed him.
'It would appear so,' she gave me a put him down look. 'Does anyone want to eat this evening?'
And with that normality reappeared and I calmed down a little but was still buzzed about what I had managed to achieve as I looked forward to my own house, seeing Miss on my letters and knowing that Pete would be around to satisfy my new found lusts.
© 2011 by Lauran
I was about 16 when I started to take an interest in how I looked, until then I had been a school uniform or jeans and sweatshirt sort of boy. But as I approached my end of school exams, I noticed girls, not as sex objects like my friends did, but as clothes horses. They wore some amazing things away from school. And unlike my friends, I wanted to share in this joy of taking an interest in how I looked.
The first thing I did was to take better care of my hair, using my mother's shampoo, and then her conditioner. It was a typical boy cut, or rather not cut, so I booked myself into a unisex salon for a cut. The first thing they asked was how do I want it? I had not really thought about it, boys just have it cut. The girl was patient with me and showed me several pictures in magazines. I picked one that was quite straight, but the distinctive feature was the fringe, long and sweeping across one eye, with the back just cut to the bottom of my neck. It looked similar to a pop star I liked, which possibly had a strong influence on my choice. For the first time in my life, I felt good about how I looked. I had a can of gel I was to use every time I did my hair. All I had to face was my mother and my friends, who I suspected might not be ready for the new me.
I was right about the friends. I walked right past some kids I knew from school and never got a look. Mum was different though. She took a second look as I walked into the kitchen, then asked where I had got it done, did I like it, and did I know how to do it myself? Not quite the 'That is terrible, go back and get a proper cut' reaction I could have got. Over tea, we had a surprisingly good conversation about hair, from which I took it that she did not mind the new look. We even discussed styles she had tried and ones she might try in the future.
School on Monday was less tolerant. Some teachers took a minute or two to recognise me, and friends wanted to know if I had gone weird or been watching the wrong programmes on TV. I joked along with them, telling them I was fed up with the scruffy boy image. Unexpectedly, the new look was a bit of an attraction for girls who said some quite nice things about my hair, but even while they were talking to me, I was checking out what they were wearing. And over the next few days of this chatting to girls, I found out they bought clothes just because they liked them, not because they were needed and functional. I had suspected this before, but lately had considered buying new trousers just because I would look good in them.
The next step was to buy something just for style. I had spent time watching what others wore, and for me it was the girls tight trousers that appealed. So with money in my pocket, but not sure where to look, I went shopping. The men's shops were not stocking what I wanted, but the more fashionable shops seemed interesting. I was asked in one if I needed help, so I asked if they had any tight jeans. The assistant disappeared, coming back minutes later with a pair of black and a pair of denim trousers and guided me into the changing rooms. The denim I could not get into, but the black ones, with an effort, I worked myself into them. Over the door the assistant asked if I was alright and did I want to try anything else. I said they were tight and hard to get on, he suggested I put them on lying down at home, but if I have them on and they fasten, then they were right. I opened the door to show him, he felt the waist band that was around my hips, and looked at the length. He assured me they were the right size for me, and did I want to buy them. They were dearer than the store jeans I could have bought, but these were what I wanted and asked if I could keep them on, so he took my money and bagged up my old trousers.
I felt quite good as I walked home, new trousers and my hair still looking good. Mother was the first to comment as she was the first person I meet who knew me. 'Oh my, how did you get into those' then asked me to turn around, before congratulating me on a good choice. I was thin enough and long legged enough for them to look really good. They were not for school, but for home and going out. So as it was Saturday. I went to meet some friends at a youth centre. The boys made some comments but the girls were more interesting to talk to, so I spent the evening talking with them.
Three weeks later, mother casually drops into a conversation that she is planning on going to see Michelle, her hairdresser. Would I like to go with her and get my hair tidied up. 'If you think it needs it?' she explained how a nice style needs to be maintained, the hair grows differently and the sharp edges blur, and my style looked better when it was fresh and sharp. I have to say going to a salon with your mother is a very odd thing to do, she was in for a cut and blow with Michelle. I was given Alice, who washed, cut and straightened my hair. I had to admit that it looked much better.
Life did not alter much with my friends, but the time spent with girls increased as my look became the norm for me, and not a novelty. Shopping trips produced more clothes, again changing my look. I was wearing my fashion trainers, tight trousers and over the weeks a lengthening fringe. I had finished my exams and was enjoying the prospect of a long summer, when mum came in with a double event evening. First, she had found me a job at a local cafe helping out for the summer, and then later when I was going to trim my nails, she gave me a lesson in nail care. By the end of the evening, I knew it was better to file than cut, and if you want them to look really good, buff them and push the cuticles back. I thanked her and admired them, because they had never looked so good.
The next thing I did was to look through my clothes and found a T-shirt that I had forgotten about. It was plain white but had been put to the back because I had grown out of it, but now I was not looking for baggy and slipped it on and found it fit quite snugly. It only just made it to top of the trousers, and with a wide belt I had bought, I felt I had a good outfit. I was going out to meet some friends later after tea. Mum asked where the top had come from, she called it a top, a very girly term. I explained and she nodded at the memory. Then she suggested a thin knit sweater or cardigan would go well, and had I considered a vest top?
On the next day I had free, I went to the shops and tried out her suggestions, and with my earnings bought one of each. Then on a whim had my ears pierced, only one was visible because of the fringe. But I knew they were there and felt good about them, wanting them to heal quickly so I could try different styles. The vest top came a week later. I noticed one of my girl friends who were not well endowed in the chest wore a nice one which looked good, so being bolder about these things asked her where she bought it, and followed it up with getting my own vest top. It showed every bump as it was a lycra mix, which was part of the appeal, but also made me consider my stomach and I started to eat carefully and exercise so my stomach would get flatter.
After a few weeks at the cafe, Jean the owner, asked me to clear tables, instead of working in the kitchen. I was in a tight T-shirt and tight trousers and felt quite good about my image. Until an elderly man said to me, and there was no one else about, so it had to be me, 'Excuse me dear, could we have another coffee?' I looked around and realised I was alone and he was calling me dear. I got him his coffee and did not correct him. He even left a tip, which for the cafe was not common. This became a common event, well a few times a week at least, enough for me to mention it at home.
Mum's reaction was to say it would be easy to understand how someone might make such a mistake.
So I asked her if I was looking like a girl.
She said she expected that was what I was hoping to achieve, and was surprised at my comments. Yes, I looked like a girl, was it a problem?
No, I liked how I looked.
Mother said she was glad, because she liked how I looked as well, what she called femmy.
With this revelation, I had to think more carefully about what I wore, thinking if I was wanting to look like a boy or girl. Jean at the cafe did not help as she got me to wear one of the long black aprons, which really looked like a skirt as it wrapped so far round the back. I got used to the customers calling me miss, sweetheart, or some other female related term. And with money to spare, I was able to indulge my new hobby of buying clothes. There was also the prospect of college after the summer when I would be free of school uniforms. I also found myself able to talk more easily with my mother. She was quite positive about many of things I liked and would encourage me to think of different styles or colours that previously I had not felt were right for me. By the time I had started at college and signed up for the courses I wanted to do, I had a fairly good collection of clothes. Some of which were mainstream, while others veered more towards an individual look that I was happy with, but could create a comment or three. In particular, I had a nice thin knitted pale lemon top, shiny dark burgundy trousers (tight off course) and a pair of narrow suede shoes. I knew it was not a look for every boy, but for me I enjoyed being different and expressing myself in this way.
At the instigation of my mother, I went with her for our fast becoming regular salon visits in October. Prior to this, we had talked about highlights and how they affect and emphasise styles. She persuaded me to have silver streaks in my hair, especially in the fringe, so this feature of my look was more defined. The whole process was far more involved than the previous cut and blows, but the results were a shock. The difference it created made me look very different and I worried had I done the right thing? But everyone at the salon loved it, and then as I walked home I picked up a few stares, which whether good or bad was part of the reason for dressing this way, to get noticed. And at college, I was noticed. Some of the girls made a fuss about the colouring, there were however more negative comments than before, so it was a good job I had chosen english, history and art, rather than science or sport which did have a style all of their own, and quite a lazy one from what I could make out.
Anyway, I was soon to learn that coloured hair grows out, leaving the roots, and so as well as a cut every few weeks, I was needed to have my roots done as well. My next move away from regular boy looks came during the Christmas break. Mum had time off as well and there was a day that I was giving myself a manicure while she was tending to her own nails, but when she polished hers with a deep burgundy, I must have looked interested, because she offered to polish mine. I turned her down on the colour, but was persuaded to let her coat my nails with a clear nail hardener. There was something about the smell and the way the brush worked that made this a quite exquisite experience, and one I knew I would repeat under the pretence of strengthening my nails.
I had a great time at the January sales, buying clothes that others seemed to not care for. My favourite purchase was a pair of ankle boots, long pointy toes, thin sole and a small raised heel in what was called calf skin. I loved them and they went down well with my art course friends, some of which had unique styles that most would not dare to copy.
A turning point in my style was the discovery of make up. Of course I knew about it before, but I had never considered using it myself until I was going out to a party and was round at a friend’s house beforehand and she was doing her face and suggested I use some eyeliner to define my eyes. She applied a thin black line to the top lids and showed me the effect in a mirror. I was stunned at the effect, and asked her about the liner in particular but other cosmetics in general, and cleansing for the inevitable tidying up that would be required afterwards. The first time mum saw the liner was the following weekend as I was about to leave to meet some friends. She called me back and took a good look at me, then asked if I like the way it affects my face. I told her I thought it was great and she agreed, and asked if I had considered anything else. I said perhaps but had not tried any of them. Then she offered to let me play with her make up if I wanted, so I could experiment with colours and looks. I thanked her and said I would like that very much.
It was a free afternoon the following Wednesday, and I spent my time not studying the course work, rather taking an interest in my mother's vanity and it's various creams, powders and liquids. I knew what lipstick was for, and mascara was obvious, but the rest was mostly guess work. She came home to find me with mascara, eyeliner and lipstick all inexpertly applied, and to be honest, looking dreadful. That evening my mother took me in hand and taught me the basics of make up, how to alter the look of eyes, cheekbones, lips, eyebrows and even the overall complexion. I was enthralled as she showed me on her face, then she encouraged me to use the products on my own skin. I could clearly see some new things I might want to do with my look.
I stuck with the liner for going out to parties, but soon added mascara and light coloured lipsticks. Then, when one of the students suggested a goth night, I went the whole way and used pale foundation and dark eye shades with dark lips. I looked horrible, but that was meant to be the look. A follow on from that was my use of concealer, and a light foundation more often, even to college on occasion. I was going out one Saturday evening, dressed in dark burgundy trousers, a tight white top and short jacket, with my face carrying light foundation, liner, mascara, lipstick all pale tones but this time I had used some light grey on my eyelids. My mother in a rather casual way, suggested if I was going for a more femmy look, why not use coloured polish on my nails? Just a tinted pink she offered, and before I had really thought it through, was sat at the table with her brushing my nails till all ten were a smooth shiny hint of pink/pearl. They looked somehow more delicate, and once they were dried, I hugged her and thanked her for the help she had given me. The party was a great success for me. The girls wanted to know what I had used and Emma, who I had always had down as lesbian, enjoyed giving me some personal attention in a dark corner.
But the most unexpected event was having a drunken Tom ask me if I was gay, as he fancied me rotten. I was rather taken aback by this conversation, but when I left he left with me, which as we lived near each other, was not a surprise. But then he went on to repeatedly tell me how good looking and attractive I was, how he loved how brave I was with my style, and thought I was prettier than many of the girls around. This was rather a lot to take in at once. I had always wanted to be different, maybe attractive, but pretty I was not sure about. But then as we walked the couple of miles home he got closer to my side, gently bumping into me until our hands touched and he caught hold of mine. Not sure how to react, I stiffened but did not jerk my hand out of his. We continued to walk but the chat was mostly his. I was having my own internal conversation about the fact that a man was holding my hand. His talk was mindless chatter, just wallpaper if you like. On reflection, I am surprised that as we walked I relaxed and allowed myself to be open to this new situation. This meant that when we got near our homes and we were in a darker area, Tom turned to face me. At first I thought to say 'Good night', but though he did say those words, just before he had kissed me first on my cheek and when I did not pull away, he then kissed my lips gently. His kiss was different to Emma's. A little rougher, more in charge than the girl’s tender touch, but good in its own way. I think he was testing my reactions really, as he did nothing more than kiss my lips for a few seconds, then part and wish me good night, and suggest we meet up again. My last few hundred yards to home were full of personal introspection, much like my restless sleep that followed once I was in bed.
In the morning, I was asked how the party was by my mother. Being tired, and of late more open with her, I told her about the people who had kissed me. She knew neither of them, but did not seem bothered by the fact I had been kissed by a gay man. What she was more interested in was the way I was spending time with girls, and wanted to know if I identified with girls or boys. I had thought about this before and knew I was a boy, but liked the way girls were less macho, the way they thought about how they looked, and the way they could just talk more freely about things which affected them. She listened carefully, concluding with me that it was no coincidence that a gay female as well as a gay male could find me attractive, as I was displaying quite feminine traits while still maintaining something of my masculinity. She finished the conversation with a question. Over the past year my masculinity had been eroded in favour of the more girly image. Did I intend this to continue and drift further into feminine expressions, or did I want to live as a more regular boy? She got up from the kitchen table and kissed me on my forehead. Her last words were 'I will love you whatever you do, you know that, don't you' This was going to be a hard day of thinking I could see.
This internal discussion about sexuality did not affect how I dressed. How could it? Nearly all my clothes that fitted me had been bought within the last year, so trousers were fitted or tight, tops were not loose. So I continued in my now established femmy style as mother called it. Luckily, neither Emma or Tom was in any of the study groups I was in, so I only met them at breaks or after classes. Sexuality aside, I was still enjoying my clothes, and two Saturdays later was invited by Lisa to go shopping with her, as she said I had good taste. Well the week before I had seen a video of Spandau Ballet, and the 80s new romantic groups, they were great at merging the male and female styles, and then there was Bowie and his unique style that seemed to relate to me. Anyway, I was with Lisa shopping when I saw a white cotton blouse. Big sleeves, frills around the buttoned cuffs, short stand up collar and laces instead of buttons down the front. I loved it and Lisa agreed I would suit it. I later bought a waist coat to go with it, so it emphasized the puffy style of the sleeves by making the body fitted. Mother approved when I showed her what I had bought.
A week later, I was chatting with Lisa who wanted to do something different with her hair, and had picked up a fashion magazine that focuses on hair styles. We spent a nice lunch break talking through what she could do and what would suit her face, cutting out several pictures to take with her to the salon she used. When we were done, I picked up the magazine and packed it with my books, hoping to have a private look at the articles. The evenings reading was quite informative, and the conversation also, when mother noticed what I was looking at. 'Thinking of a change?' I said maybe, but in the back of my mind was a picture of a boyish girl with a curly style that was very full and not too long, half way down the neck really. 'How about something with curl? Ever thought of that?' so I showed her the style, she nodded 'Bit shorter than you have it now, would you mind?' I said not, and she took it on herself to arrange a booking at the salon for Saturday. I had only been thinking about it really, and all of a sudden I am having a new style.
Alice was always nice to me when she was cutting my hair, and this time was no different. 'New style I see' then we discussed whether it would look good and if my hair was suitable. She suggested keeping the highlights in. I had only read about perms and was a little nervous when the small rollers and smelly liquids that Alice wore gloves to handle, as she started to be apply them to my head. Once started, I reckoned all I had to do was sit back and let her do whatever needed doing. I could hardly walk out half way through. Eventually I was finished, my brown hair with highlights was now completely changed. Instead of straight down to my shoulders, it sat an inch or so off the shoulder and stood out from my neck a couple of inches. I still had a fringe across my face but not as low this time, and it was fixed in position with something she had combed into the hair when finishing.
As with anything new, it takes some getting used to and this was no different. I looked at my reflection and was struck by how feminine it looked. Had I gone too far this time? Alice told me I looked fantastic, and my mother who had come back to pick me up agreed with her, telling me I should make the most of a professional styling and go out that evening. As luck would have it, Tom saw us walking to the car. 'Hello Mrs Connor' we replied 'Hello Tom', then he recognised me and a grin spread over his face. 'Mark, sorry I didn't...er.. well you know. You look great, going anywhere special' I thanked him and told him I had no plans. Mum then chipped in 'Look it is getting late, why don't you two go on into town, get something to eat and have a good time. Here, take a twenty.' She was right. It was nearly six. I found my voice 'Not sure I want to go out like this' meaning I wanted time to get used to the new hair. But she took me the wrong way. 'Oh silly me, of course you will want to change. Tom, do you mind coming back to ours?' Tom, who had only agreed with nods to all this, but I could sense was not averse to a night out, said yes. And that was it. I was going out with Tom for the evening. Mum knew we had kissed a few weeks ago, but that had not stopped her encouraging this friendship. If anything, she seemed quite keen on the idea.
I changed as expected and without thinking of the ramifications, picked up a lemon collarless shirt and my white lcyra trousers, tucked into the boots on my feet and a little make up as it was the weekend. I went to meet Tom, who was happily chatting with mum about football and how Steve Gerard is quite good looking. We walked out with her final words 'Have a good time you two' following us down the path. 'Tom, I don't know what got into her'. I apologised on her behalf. 'No need to, I have been trying to catch you and ask if you wanted to do something together, and now we are'. We caught a bus into town and had a burger, then went to watch a film. Some sort of comedy which I found funny, but all the time I was aware of Tom's arm pressing on mine. When it finished, we walked out in the crush of people and noticed how many couples had been in the audience and how me and Tom might well look like a couple also. For some reason, this made feel quite comfortable at his side and when he grabbed my hand so we did not get split up I gripped it and followed. Once outside we did not release our grip. Tom being a year older could legally drink in a pub, so before we left for home, we stopped at a bar. I had coke, he had lager. We chatted about the film, about my mother, about college, and eventually about us. He had his hand on my hip as we stood facing one another. He explained how he was gay and that, as he said before, he found me attractive, and if I was interested he would love to go out again and see where it takes us. I had my back to the room, so when he leaned over to kiss me, and after the initial shock, I could imagine the other customers seeing a man kissing a girl, it was only from the front you might notice I had no bumps that a girl would be expected to have, and a bump that a boy should have. But for the time I let him kiss me, hoping we offended no one.
We caught the last bus back to our area of town, and much to my relief Tom was not quite as forward with his attentions as he had been in the pub. But once back into our streets and taking short cuts through darker areas, he was not so reserved and once again held me close and when we were at my back door, we kissed once more, this time with more passion, and from the pressure he was exerting on my thigh, a more stimulated penis. After what seemed like ages, I was getting cold and told him it was time he was going home. Without any resistance, he thanked me for a great evening and hoped we could do it again, lastly giving me such a gentle kiss on my lips it made the hairs on my neck stand up. I went inside to find my mother sitting up watching a late night film. 'How was it then?' I told her about the film and going for a drink in the pub, then she let slip she knew we had been standing outside the back door for a while. When I said we had just been chatting, she gave the 'look over the glasses' stare and said 'whatever you say' then paused 'Do you want a drink?' 'That's a good idea, do you want one' 'Yes please, there is some Baileys out, two chunks of ice first. Have one yourself if you want to try it' I spent the closing moments of that eventful day sitting with my legs tucked underneath me, alcohol in my stomach, and a nice feeling of being comfortable with mum. As we sat, she asked if I had got to like my curly hair, and then quite casually asked if Tom made a good boyfriend. In my relaxed state, before I put the answer through any sort of filter, I said he was. Then she told me there was a message from a girl called Emma, who wanted to know if I fancied going bowling Sunday afternoon, then asked 'Is she the one who always wears jeans and has short hair? I told her it was. She just said 'Oh' in a questioning tone.
My Sunday turned out to be fun. I kept my bowling friend happy by losing on the alley, then spending a few hours with her afterwards. We ate pizza, walked through a park, sat on a bench, but most significant was the talk. She was quite open about how she liked me and would like us to be a couple. I was still remembering the night with Tom, and hopefully made it clear that while I was happy to be a friend, I did not want to tie myself to a relationship. I wanted to be free to see whoever I wanted. This did not put her off, and we continued our evening hand in hand, even kissing at times. Emma was the first to actually comment on how I dressed, making a direct statement about how I can look like a girl. Then taking it further by asking if I could see myself actually being a girl. This was so direct, it took me by surprise, but not the topic. I had taken plenty of time to think about how I was seen by others, and besides the appeal of looking different, experimenting in an arty way with clothes, but there was something I liked about looking like and being a feminine boy, what my mother had called a femboy. Emma took my desire to be seen as feminine by asking me to wear make up more often and if I wanted, to use stronger colours. I had a lovely time with Emma, well that was what I told her and my mother, partly because it was true, but also to try and keep my personal questions to myself. Just what was I , and who was I, and what should I wear in public?
I had several weeks of study, going out with Tom, Emma and a few times with Lisa, but she was more of a shopping partner and gossip chat time. Christmas was coming up and several parties were organised, as well as student discos. I went to some with Tom and a couple with Emma. They knew about each other, but I did not wish to go to a party with both of them there. Mostly the parties were small, but Tom invited me to a special night he had heard of in town and asked me the day before if I would dress as femme as I could, and that he would like to see me push the make up further than I had in the past. When I asked him what he meant, he explained how I knew he was gay, but something he really finds attractive is she males. I had come across this title. Some people were happy with, but I was not, seeing myself as such a person. I was not into trying to be a girl and hiding my manhood, but I was flattered by Tom's request and wore white trousers, a white satin blouse under a pink woollen vest and jacket. His venue for the evening was a gay bar that was well known in town. At first I was apprehensive about being so open about being with Tom, but I considered how I looked, and with Tom's encouragement, we did go in and have a drink. I think Tom had been in a few times before as he knew a couple of people. Thankfully I did not see anyone I knew and managed to relax, that is until I got chatted up by a gross middle aged man who smelled. I was rescued by Tom when he returned from the gents, by putting his arm around my waist and giving me a kiss. For all my fears, the evening was quite fun. Plenty of people to watch, easy atmosphere and friendly staff. That was on top of Tom being very attentive towards me. I definitely felt like his partner, with him being the alpha. I felt I was possibly the girl, or at least how I think a girl might feel with an attentive boyfriend.
A week before Christmas and I was chatting with mum about her plans and what we would be doing. She had a couple of parties with friends and work over the holidays, but she had fallen out with her parents and would not be seeing them, so Christmas would be the two of us. Then she moved onto the fact that we had hair appointments for the weekend before Christmas, and she was going to have a special for a party that evening. I had planned on a tidy up with Alice, but for some reason mentioned that Tom had wanted me to dress more femininely. Mum just smiled and said 'Why not'. I countered by pointing out that I am a boy. She cut in, telling me 'a pretty boy though, who gets mistaken for a pretty girl' I was having to agree with what she said. Then she suggested I get Alice to give me a mixed blonde colouring when we went. And as usual, I did not take long to agree to the idea and actually thought it would look good.
I was not mentally ready for the transformation that blonde hair gives you. I was stunned when Alice finished. Not only blonde, but she had tightened the curls so they stood out more than usual. Tom had heard that I was having my hair done, and asked if he could take me anywhere so as to show off the new me, like my mum would be doing at her party. I did not want to sit about at home alone, and found myself with Tom in the gay bar, feeling every bit like a girl out with her boyfriend. Some others came and chatted with us. Many gay men openly being affectionate, and some a bit like me, clearly not the 'man' in the relationship. I thought I was possibly the most feminine one there, until it was pointed out to me that a couple of women at the other side of the room were actually men. If I looked they had adams apples and rather large hands for a woman. As the conversation went on, Tom kept mentioning these two transvestites. Eventually I asked if that was how he would like me to dress. He said he would love to see how I looked, but it was up to me, no pressure.
The evening was notable for what happened when we got back to my house. Mum was out at her party, so I felt comfortable inviting Tom in for a coffee. While I was making the drink, he approached me from behind and cuddled me from behind, his erection pressing into my back. The kettle was left to switch itself off as we got into more passionate kissing, and for the first time, I put my hand onto his trouser bulge and massaged it through the fabric until there was a tensing in his body and a wet patch developed on his front. Just at that moment, I heard a key in the front door and we straightened ourselves up, but clearly looked guilty as mum walked in. I stumbled out 'I was making a coffee, do you want one?' she smiled back 'Oh no, I will take a glass of water, switch off the lights when you have finished.' The smirk on her face made me even more uncomfortable.
Christmas was a low key event, cards around the house, few decorations and a table for two. But we had a nice relaxed day together eating and drinking a traditional meal, and with my maturing age allowing me to drink champagne without regulation it seemed. We opened our gifts. I had bought mum a bottle of scent I liked the smell of. She had bought me a warm jacket. The significant feature of this item was that it lacked buttons, having only a belt and up stand collar. I tried it on. 'I have the receipt if it is the wrong size' not if I don't like it I noticed. And the receipt was Le Femme Boutique, confirming what I guessed to be a woman's jacket. I thanked her and we opened our other gifts. There were the usual chocolates, etc, but Tom had bought me a matching silver necklace and bracelet which were fixed to me in the appropriate places. Mum telling me they were pretty as she manipulated the tiny fasteners.
I must have drunk a bottle of the wine when we sat down to watch a Sex in the City DVD we had received. These women could dress up with great style, which sparked a chat between us. My barriers and inhibitions down, I told her about the transvestites I had seen in the bar, and the conversation I had had with Tom and his desire to see me dressing as a woman. We continued drinking and I remember little of the evening. Waking the next morning with a bad head, but slowly becoming aware that I was wearing something different to my cotton pyamas. Through the fog, I felt the satin fabric wrapped around my legs and realised I was wearing a full length nightie. I eventually got up as my headache eased, but that did not ease my lack of awareness. Even though I got up in a new item of nightwear, I still picked up my dressing gown before heading out of my room to the toilet, then onto the kitchen. Mother was at the table reading a website on the laptop. 'Good morning. How are you feeling?' 'Rough' I replied. She got up to make me some toast and coffee, adding aspirin to the plate. The conversation was limited until the tablets had taken effect, my awareness increased with a clearing head. I was sat in a long white satin nightie clearly visible below my dressing gown.
My first proper sentence was to ask if wine always gave a hangover. I was told sometimes alcohol had a bad reaction. Other times no after effects, but mum told me we had had a good evening. When I asked what had happened, she realised I had not remembered the latter part of the day. She told me we had watched a couple of DVDs and talked about cross dressing.
I recalled some of this, but still had no idea why I had worn the nightie. As we talked, it came out that we had ended the evening having a girlie time. We had got ready for bed in a girlie fashion, hence the nightie and as she prompted me, I noticed that my fingers had had a manicure and she told me I had returned the favour and done hers as well. Apparently, I had used her moisturisers and face packs, but it was not until I got up and went to wash properly that I saw my face. I must have let out some noise, possibly a scream. My eye brows had changed shape! From a quite broad line across my eyes, I now had neat wedge shaped brows tapering to the outside. Mum came in, possibly thinking I had hurt myself.
'What happened?' I demanded
‘we wanted to see how your face would look if we shaped your brows. They look good, don't they'
I was still staring at the mirror and touched them with a manicured finger, 'OMG how girlie was I last night?'
'Enough to pluck most of those hairs out yourself' I think I went a little pale, then blushed as I considered how my friends might take to this new look.
Mum then made the statement that hit hardest. 'I do hope you like them, there is not a lot we can do to them, other than thin them more, afraid you are stuck with them, it takes weeks for them to grow back'. She then hugged me and told me she was sorry if we had gone too far. She thought I was happy with the things we were doing at the time.
By mid afternoon I was dressed in my favourite flared jeans and lemon hoodie. I had not been able to unfasten the bracelet, so I kept the matching necklace in place also as it did not show, but would be able to let Tom know I was wearing it if he asked. Lisa had managed to get her house for a get together on Boxing day, but before I left my house, I had another drift away from my previous boy look. My new jacket was hanging on the hooks by the front door. My old warm jacket was missing. I asked mum where the old one was. She looked at me quizzically. 'You really don't remember much of last night do you? You threw it in the dustbin, said something about it being a link with the boy you used to be.' Right now, I was not so sure I would have been so rash, but the choice was, root it out of the bin with all the food waste, or wear the new one. Simple in the end. I wore the new one.
Lisa noticed the eye brows straight away, and then told me the jacket looked good and asked what else I had got. I showed her the bracelet which she thought was pretty. Lisa herself was wearing a stunning party dress, and like the girl I was becoming, I told her it was gorgeous and she looked fantastic. As the party developed, more friends arrived and we played silly games until we had got giddy, the couples pairing up in their own intimate parties. Neither Emma nor Tom was there, so I ended up drinking and chatting with three girls and a boy. The subject of my eye brows and continuing alternative look came up, and was surprised none felt I was being stupid with my feminine styles. Sara and Kee even suggesting I should push myself further and really blur the gender distinctions. When I asked what they might have in mind, they listed more make up, I only had mascara on at the time, more obvious ear rings, finger rings, shoes was another area I could change without being OTT. It was late when we split up and the topics had changed many times, but I walked home deep in thought as to what people saw when they looked at me, and how I felt about the fact that my friends had no problem with my alternative style. Mother clearly had no problem either as she had left the satin nightie on top of my bed so I would see it when I got ready for bed that evening. Picking it up, I felt the softness and being slightly drunk, put it on and went to bed, wrapped in its luxury.
The days after Christmas are always a bit of an anticlimax. I sat about at home reading and studying, as there seemed nothing better to do until I would be going out to meet Tom or one of my other friends. Over lunch, mum asked how I liked my deliberately feminine touches. I said I was getting used to them, meaning the eye brows, then somehow the conversation turned into a rerun of the one I had had at Lisa's, suggesting I try out some more feminine items. She suggested jewellery and using make up more regularly. What was bothering me a little was that she was being so positive in her encouragement. It was she who had taken me to the salon, she who had taught me about make up and nails, she who had bought me the girls jacket, she who had plucked my eye brows and dressed me in satin two days before. I summoned up the courage to list these things, and ask if she planned any of it. Her response took me a little by surprise. It was me who had always initiated the style changes, the hair, the make up, the clothes, and she was happy to encourage me at first. But as the months had passed, she had seen in me a different side, one that could hardly be called male or manly. I was not a big lad, but with my new look and increasingly submissive attitude, I would do almost anything she suggested. She concluded with the opinion that she felt I was going to end up completely feminine in look and attitude. When I let this sink in, I asked her if she saw me as a boy. She shocked me by saying no, I was me, her child. But pushed, said that she saw a son who lacked many of the boy traits, and would one day stop being her son in a regular, society approved way. 'You think I should be a girl?' I asked eventually 'Why not, you behave like one and look like one, the sooner you accept you are never going to make a half decent macho man, and that you might as well be a girl, the sooner we can get you sorted out properly'. I was stunned and she could tell, so left me to think what she had said about me on my own.
I did not do much studying that afternoon and later on with Tom, I was quiet. He asked what was up and I told him that my mother thought I made a useless man and should just be a girl. I could tell from his reaction he was a little shocked too, it was a little harsh, but as he thought about it, came to agree with her more or less when he told me he considered me to be his girlfriend. My maleness was taking a beating that day for sure, and as we ended the evening in a passionate embrace with me massaging Tom's erection to a climax, I felt almost confirmed in my role as the girl in the relationship. But what to do about the situation, rebel and assert my male nature, or let myself drift more and more into a world of feminine appearance and attitudes?
The nightie was out for me on the bed once again, and once again I put it on before going to bed. I slept fitfully, half dreaming about being a girl, how would it feel, how would people react, would a gay man like Tom still want me, did I want to do any of these things. I had one dream that was pivotal. I was with Tom and I was not clear how I looked, but I was female. Breasts, long legs, the full ideal image, and I was happy at his side.
In the morning, I went down for breakfast in the nightie. Mum was still on holiday and looked a little surprised as I had not covered myself up with my heavy bath robe. As I made the toast, I found the words 'Did you mean what you said yesterday, that I make a hopeless man'
She looked at me with loving eyes 'that is not quite how it was meant to sound, not hopeless, more not a particularly macho one, I suppose a special one' she paused 'why?'
'Well I have been thinking' I started, and went on to say that I would like to find out what it might be like to be a woman, and on new year’s eve in particular when I planned to give Tom his dream of taking me out looking female, not just femmy. She gave me a searching look and asked if I was sure. I said yes, but then limited it to no skirts, just trousers and tops that I already had.
'Oh no' she came back with, 'if you are doing this, you need to do it properly. Maybe not skirts, but I think we need to let you know a bit more of being female than just wearing clothes' she looked straight at me 'you will be very pretty, but just this once I want to treat you. If you are serious, I will help you, but you do whatever I tell you to do. Understood?'
Not fully understanding, I said yes.
'Right, well in that case Ma.......rie, the kitchen needs tidying before we do anything'. This was unexpected, she always cleared up. 'You see Marie, being female is not just dresses, there is all the things men expect you to do, and housework is one of them, so time to start sharing the jobs if you are going to be a woman like me'. I could not think of any argument against this logic, so dutifully I cleaned the kitchen. When I was done, she invited me into her room. Laid out were several things I expected she had got out for me. 'First, I think you should get rid of your body hair and shave your pubic area to a neat panty line. Silently, I took the bottle and went to the bathroom, emerging later clear skinned and wearing a tight pair of pants she called control briefs. She next fastened a bra to my chest and filled it with tights. I was beginning to feel very different as I sat at her vanity and used her make up as she directed, then once she had brushed and moussed my hair into a volume style, I could see a female face looking back at me. I was then told to go and get dressed. I soon found the bra pushed my tops out and shortened the front, while the trousers had a flat front, giving no indication of the genitals within. I came out in my flared jeans and a fawn sweater that barely touched the waist band on the trousers now.
Mum was waiting for me with her car keys, 'That took ages, another indicator that I am right. A boy would have picked up what was out, you spent time putting an outfit together'. I was used to going out wearing the clothes I was in. My hair had not changed that much. I had even worn this much make up before, but I felt nervous stepping out to the car. The only real change was the underwear, and the jacket was hiding the effects this was having on my chest. I had to go or mum would have accused me of weakness, so I joined her in the car and I was off to where ever she had in mind. There is a big shopping mall a short way along the motorway that she confidently said would have enough shops for us to find what I needed.
First off she wanted to find some female footwear, so it was shoe shops and looking at heels while I was having to consider what style I might like. Given my veto on skirts, she steered me towards boots with the idea I tuck trousers into them. I had seen girls wearing this style, and after a few nervous try ons, she paid for a black pair with wedge heels, with the comment that the wedge will fell more stable than a spike heel. But as we could not find a pair with a loose enough leg for my jeans to go inside, she now had to find 3/4 trousers. We also needed to find a new top she informed me. So we browsed through the fashion retailers. My first horror here was being given a blouse and told to go and try it on. I looked at her with what I hoped was a pleading look, but she just squeezed my arm and told me I would be fine, the changing rooms are private. With butterflies in my stomach, I took the blouse in for a try on. I did not like it, so came out having given it a try, but more importantly, I had been into the changing rooms alone. Mum did suggest that next time I come out to give her a show before taking it off. It took a couple of hours and several trips to changing rooms before we were happy with the choices. I had a pair of satin 3/4 pants that came to just below the knee, the baggy nature in the leg stopped with buttons, the wide belt sitting on my hips. The top was similarly very different to my previous choices. It was a gold coloured square necked smock top that flared out in soft folds to my hips, with short bell sleeves. Now that we had the clothes, she said I needed accessories. A long string of black beads, a wide bangle, long chandelier ear rings, and my first finger ring. Then, as a last purchase we bought a long pink silk scarf to go with the jacket and a supply of control pants and bras, this was not going to be a one day event I could tell.
Once home, I had to go and change into the new outfit. The first thing I noticed was how soft the new fabrics felt against my bare skin. The next was how walking in heels, rather than just trying them on and standing in them, was going to take some getting used to. Mum was waiting for me in the lounge when I was ready. She tucked the button cuff on the bottom of the trousers into the top of the boots, and then rearranged my hair so the ears and decorations were more visible.
'So, how do you like the outfit?' she asked
'Not my usual style I must admit, but it is certainly more feminine. Should I go and change now?'
Her reply came back lightening fast 'God no Marie, I think you need more time as a woman, and right now I think the women here should be sorting out something to eat, so get an apron and help me in the kitchen'
I rarely even helped her cook, but that day had been a day of new beginnings. We got the meal started and while it cooked, she brought out some more items and told me to sit down. I held out my hand as she sorted out some opaque oval shapes which I guessed were false nails, then without asking she glued them one by one onto my finger tips. It did cross my mind to ask if this was a bit too much, but I had agreed to let her do anything she wanted. The meal was ready as she fixed the last nail on. My first time laying a table with long nails was a challenge, but with practice, I worked out how to pick things up and adjust the way I used my fingers. Eating was just as complicated. Mother never offered advice, but I could see her smiling at my difficulties. The meal over, I had to clear up before she called me to her for next part of my instruction. She painted one coat of plum coloured varnish onto the nails, then told me to apply a second which turned out to be more awkward than I expected, but I did all ten with some effort. I could think of nothing else she might want me to do, but I was wrong. Among the items she had were eyelashes, not ridulously long she said, just enough to make the lashes noticeable. Five minutes later they too are glued in place and my eyes feeling odd.
'Right one last thing for tonight' she said as she picked up her tweezers,
'but you have done that already, surely they are fine'
'You agreed to let me do whatever I felt was required, and I think your face could do with thinner brows'
'but what happens when I go back to school, they will look...well thin'
She gave me a hard stare 'you agreed to being made as feminine as possible without wearing a skirt, and I say your brows look too masculine still, and certainly not as feminine as they could be. So let's get on with it'
I just looked up at her and agreed.
'I think that proves my point, no man would have given in so easily. Only a girl would let their mother pluck her eye brows' She only pulled a few hairs out 'do you agree with me Marie?'
I had to agree with her. I had given way and I could think of no other boy allowing anyone to do the things she had done to me that day, let alone pluck a few hairs out of my face. When she was finished, I looked in a mirror and once again agreed with her that I was indeed quite pretty. 'Now we are agreed on that Marie' with emphasis on the name 'let's have a girls drink. Two Baileys on ice I think, then we can relax after our hard day’s efforts'
we went to bed after a couple of the liquors had slipped down our throats. I had owned up to liking Tom a lot, and mum had admitted she had always wanted a daughter. Before going to bed, I was told in no uncertain terms that I was to clean off the make up, but the nails and lashes stayed, and I was to sleep in a nightie which she did not need to tell me to do. The thought of satin on my hairless body was one of the sensations I had been looking forward to once I realised how sensitive my skin had become.
Morning came around quickly, with mum already up and knocking on my door telling me get up as there was lots to do. There never had been much for me to do in the past, but I did as as she told me. Over breakfast, she told me I had an hour to get dressed, hair done and make up. Then she had some jobs she needed help with, like getting some groceries. When I asked how to remove the nails as I would look odd going to the shops with long plum coloured nails, she informed me that Marie would not look odd with long plum coloured nails and that she was not going to have another argument about whether I was a boy or a girl. That had already been decided, for now I was a girl. Then, as if to reinforce the message, she came into my room while I was dressing and removed all my male underwear and the few old Mark clothes I had not thrown out already.
As she left with her bin bag, she suggested I try the boots under the flared jeans, I would need to practice walking on heels. We left the house together, but when we got to the shops, she made me go into the supermarket on my own. I had a few items of food to get and she added to the list foundation that I had to check was the right shade for my skin, and pick up a nail polish that I liked. This was a big challenge, out on my own dressed quite unmistakably and far too femininely and buying make up. I just hoped no one saw me that I knew, though I did feel confident enough with the look I had, that I was pretty enough to be mistaken for a girl by strangers. It took ages to find the right items and select the right shades, foundation being the hardest, but nail polish was nearly as bad ( I choose a pink with flecks in it) and picked up a lipstick to match, thought I might impress mother with that, and it did. She said it was a going out at night colour with the glitter in it, so I should save it for New Years Eve. As for the rest of the day, I spent it doing housework while mother sorted through cupboards having a clear out. But I was not left to just get on with the jobs, she kept an eye on me, reminding me to move as a girl would, as if wearing heels and having extensions to my nails was not enough, I now had to consider how I picked things off the floor, sat down, even how I walked. And she still found time to tell me my lipstick needed redoing and that I had chipped my nail polish. It was all very trying being a girl.
To avoid embarrassment I did not go out, just answered the phone and said I was not too good, but did tell Tom I would be going out on new year’s eve as he had wanted, which made him happy. I had three days of being her daughter before I would be going out, which was the purpose of this exercise. When there was no housework to do, mum would take me to try out different colours of lipstick or eye shadow, maybe redo the whole face. It was while we were experimenting with colours that mum picked up her brush, my hair was parted in the middle and gelled in position to the sides of my face. First she brushed the fringe back over the top of my head and clipped it back, exposing my forehead which neither of us liked, so she picked up scissors and brushed it forward, but before cutting 'Remember dear, your mother knows best, so no arguing' and before I could argue, had cut into my fringe. My hair being curly meant it did not have sharp edges, which was just as well because when she finished, I had a feathered fringe coming just below my brows.
Then she tucked the sides behind my ears.
'I think tomorrow you should go out and get yourself some nice new ear rings, now that you can see them. I was thinking of saying something about going back to school looking like this, but as if she read my mind, I got a hard stare which I dare not challenge. Instead, I ended up looking at my fingers which were entwined in my lap. 'You know, you look so cute when you do that, looking at your hands, I'd swear you've been doing it all your life. Come Marie, time for you to practice your cooking skills once more' and with that I was dismissed and without complaint went to the kitchen to start the supper. Behind me I heard her say 'I wish you had not said no to skirts, they would look so good on you now, you wiggle your arse in those heels' I turned round and in an offended tone said 'Mother' but she was right about the wiggle. Maybe the heels provoked my hips or the encouragement she had been giving me, I now walked one foot directly in front of the other, and as a consequence my hips moved from side to side and my hands stuck out horizontally to help me balance. In only a few days, I had affected my walk so much, she complimented me on it.
New Years Eve came at last and in the afternoon we started getting ready for our respective parties. First a shower, shave all over to check for any stray hairs, then after I had dried her hair and brushed it out, she worked around mine with curling tongues, tightening up the curls. Then in dressing gowns, we painted each other's nails. Doing our own faces before sitting down to a couple of glass of bucks fizz. I had not found this experience bad, but that afternoon of pampering each other, then sitting around waiting before putting on our clothes was just great. I felt like a proper Marie.
Tom called round at seven. Mum had told me to be upstairs and pretend not to be ready, just wait a minute and dab some scent on before coming down. As I walked in, mum said to Tom 'Your Christmas wish I think' as she gestured to me 'Now Marie, remember what I have told you about looking like a girl'
'Yes mother, I must behave like one as well'
She nodded her head at Tom and I took it to mean that I should greet him, so I went over and kissed his lips before saying 'Hi'. Tom managed a 'wow' somewhere in the first few minutes. But any further reaction was stopped because the door bell rang and mum welcomed into the house a six foot man, middle aged but still fit and very smart. Now I knew why she had put so much effort into getting ready and wearing the rarely seen long red silk dress. 'We have just been having bucks fizz, anyone fancy joining us?' Clarke smiled and walked over to her and kissed her cheek. 'You look gorgeous, and yes to the the fizz, might as well start the fun now'. Mum just looked at me and I knew I should go and make the drinks. Tom said he would try one, so no quick escape from the situation. I took the drinks through and mum introduced me as Marie to Clarke, who gave me a kiss on both cheeks and told me I looked great. We made polite conversation. Tom and Clarke talked about football as they both supported city, while I just felt awkward pretending to be a girl, with a man who knows I am really a boy, while the other clearly thinks I am his friend's daughter. This could go so terribly wrong I kept thinking, and then telling myself not to blow the disguise or mum would kill me.
We finished our drinks. Clarke made comments about needing to get on the road. Mum pressed some money into my borrowed small gold shoulder bag, and kissed both of us, telling us to have a good time. Being without a car, we had to take a bus into town. Tom held my hand all the time, leading me into the gay bar looking very proud. I felt he was showing me off in some way, which felt quite bizarre, as for me I would quite easily have just gone unnoticed. Tom being 18 was able to get drinks from a busy bar that did not check too carefully who was legal. We were not sure if my student card picture would really have helped clear up my age if challenged. Having spent most of the time between Christmas and the end of the year being drilled by my mother, I was constantly aware of how I should walk, sit, drink, but she did not teach me how to treat Tom and others. I had to make my own rules for these situations based on her short talks about being Marie, which basically boiled down to Tom is the man. I should do whatever he asks because he will take care of me. Her attitude came over as men are better than girls. I am equal with women, not very 'equal opportunities' I know but it was how she viewed the sexes, and now as I stood next to Tom, I quite easily knew that I could agree with her.
Tom was in charge and all I had to do was follow his lead and make sure I was pleasing him and making him feel superior to me. With some more alcohol in us, we chatted freely. I had the occasional hand stroke my arse and talked with the other women there. A few of them I was sure were like me, pretenders. As the hour got later, I was chatted up if Tom left me alone, and come the midnight celebration it was easy to go and hug anybody you wanted, it was a free for all. Though I did notice that there were quite a few men looking to give me a hug, I was sure if I had come as a boy that would never have happened. An hour or so later, the party was breaking up and Tom suggested we head for home. There were no taxis to be seen and it was going to be a good walk back, so we started walking. With my jacket pulled round me and the scarf warming my neck we walked, but it did not take long for my heels to make their presence known. They had been making my feet ache before we left the bar. Now I was walking without a break, they were making the ache move up the scale to pain. We paused at a bench to give me a rest at about half way, as we sat I wanted to know if the pain was worth it, so I asked if he had enjoyed me being his girlfriend for the evening. He was clearly pleased with my efforts by his body language, but his comments were full of encouragement. He pleaded with me to be his girlfriend more often, or at least be more feminine. The one criticism was that I had worn trousers. Why had I not worn a skirt? I explained how I had agreed to the feminization if I could wear trousers as a sort of restrainer on my mother. He suggested that next time I allow her to do whatever she thinks would suit me. I promised to think about it and not just the skirt, but the whole feminine look.
We reached my home and the lights were still on as we had left them, so mum was not back. I invited Tom in and took my boots off, and then we kissed. Tom was very passionate and got me to stop thinking about how tired my feet were as we stood facing each other. I could feel my dick swelling but the tight pants stopped it growing. Tom had no such problems. As we kissed, he pressed his growth against me. As I got more excited, I massaged it, but we moved on when he undid the zip and allowed it into fresh air. Somewhere in the back of my head was a mantra mother had given me 'please your man that is your role'. I first took his cock in my hand, and then in the excitement I felt him push me down. Whether he did or not I am unsure, but I slid down until I was facing his meat and kissed it, then licked the tip. Slowly I licked and kissed more of it, until I had it in my mouth. It was inexperience I guess, but he could not stop himself coming and unloaded himself into my mouth. I don't know what was the most shocking thing happening at that moment, having cum squirted into my mouth or the door opening and my mother taking in the scene. She saw her son giving Tom a blow job. Without hardly a break in her speech 'Oh... hello... when you are ready I was going to make a coffee for me and Clarke, if you would like to make them when you are ready'. She turned and pulled the door closed and left me blushing like mad. Tom pulled me up, kissed me and said it was probably time for him to leave. Then, as he left, kissed me and told me I was fantastic and would love to take Marie out again, but maybe I should put some fresh lipstick on before taking the coffees through. As he made his comments, he used his finger to wipe some spunk off my chin and rather sexily wiped it on my tongue reminding me of the taste. I sucked his finger. He smiled 'You liked that?' I smiled and replied 'I think I did'.
I took the coffees into mum and Clarke, lipstick repaired and chin cleaned. She smiled at me as I offered the cups.
'Good evening Marie?' she asked,
'different from last year'
'it certainly looked that way. Tom have a good time?'
'I think so'
'he looked pleased when I saw him'
'only doing what you told me to do'
'did I?'
'yes you did. I think Tom was pleased with how it turned out’. Mum was looking at me, and Clarke was looking confused. 'Mum will explain, I'm off to bed'
I have no idea what was said between them that night. I went off to my room and stripped off the feminine clothes, and with little ceremony dropped everything plus the nightie into the laundry basket. Then I removed my make up, lashes and with pain, the nails. Telling myself I was now a boy again and back to normal.
Come the morning, I showered and dressed in dark colours, trying to make some sort of statement I felt, and went down for breakfast. Mum came in later, looking very happy in her night clothes. 'Morning Marie' 'Morning' I replied, responding to the name. Then I heard someone in the shower. Clarke had stayed the night and unless I hid, he was going to see me again and I was to him at least, a girl. We had a brief conversation to confirm that he had stopped and mum used a phrase like mine about pleasing a man, which had been hers in the first place. Then before I could hide, he entered the kitchen. 'Morning Marie' He looked a little awkward about being there in the morning, guilty about what he and my mum must have been up to in the night. But mother just asked me to put the kettle on, using my femme name with emphasis.
After that I went to my room, only to be called down again when the phone rang and she shouted for me. 'Marie, Tom on the phone for you' the whole street could have heard, not just Tom I was sure. He took great interest in why I was still being called Marie, and suggested he come over as he had enjoyed his time with me as Marie. I bet he did I said. He let me know that he was keen to take me anywhere as Marie. When I pointed out I still had school to handle and that would be as Mark, he accepted Mark would make a second best. I told him he was pushing his luck. Later in the day, when Clarke had gone and the house had settled down a little, mum announced she was going out to the sales, but before she left, gave me instructions to get the washing out of the machine and dry it, and to prepare something for supper. I had thought my life as a girl had ended, and I would be going back to being a boy, and the jobs caused me to let out a 'muumm' with a bit of a whine. Which got a very swift response, starting with ‘Now look here young girl’? I listened as she told me that unless I wanted to get my hair cut off, throw out all my nice clothes, stop seeing Tom, then as far as she was concerned, I was more daughter than son from now on.
I stood there thinking as quickly as I could, realising this was a pivotal point in my life. The choice I made now could affect me for the rest of my days. As if sensing my conflict, she spoke again to tell me that no real man would kneel in front of another man and taste his cum, adding at the end that I was smiling at the time, so I clearly was not doing it under sufferance. She waited a moment, maybe for me to say something, then repeated the jobs she had asked me to do, kissed my cheek and said 'See you later Marie' and was gone. I sat down to consider my situation. Mum clearly liked me being a girl. Tom had enjoyed our night together. With a few reservations, I had enjoyed the night and even the days beforehand. If I did not have to go back to school, I told myself I could quite easily fall in with the role, but I could hardly go in looking as girlie as they wanted me to be. By the time mum had returned, the washing was done and I had prepared a meal for us. Symbolically I was accepting the female role, but I had some questions about how I was going to handle school.
She had anticipated my opposition and quickly unpacked some bags for me. First out was underwear. I was to dispose of all the male items she had bagged away and replace them with the pants she had bought. She had also bought training bras for the non school days, then she produced some more nighties, then she gave me a regime of treatments I was to keep to. Including depilating, manicures, and the one she knew would be hardest, eye brow shaping. She never mentioned the regular salon trips, as I had already been doing that for months. Finally, she said that I should go through my clothes and clear out anything that has not a female size label. I did ask if this was all necessary. She said it was and if I wanted to be Tom's girl as much as she thought I did, then I would have to be her girl as well. Which meant I had to be one all the time for her. I did think to myself, 'If I where a man, I would not accept any of this. I would stand up and say no, I will live my life as I want to', but I could not go against her or the idea of not being Tom's girlfriend. As I tidied the pots away, the discussion came to an end with my accepting to be called Marie at home and to being a daughter. No longer would I be her son. The name Mark ceased from that moment on. She even made it clear that the next time she saw Tom, she would explain the situation to him so he was under no illusion as to who I was becoming. She finished by giving me a hug and telling me this was what she had been hoping for since I first went with her to the salon, and I had made her very happy indeed. That was a lovely moment, but I still had to cope with the outside world.
I had to get out and meet people, as the phone kept ringing, with them wanting to know if I was fine as I had not been seen out much since Christmas. Lisa was the first to see the post new year me. She immediately remarked on the fringe and then the shaped brows, and asked if I had been having fun over the break. I told her my mother had been pushing my boundaries. She told me my mother had good ideas, and maybe I should let her guide me more often. If only she knew I had on a lace thong and a satin camisole, maybe she would not be so encouraging. She also commented that I was without my usual mascara. I said I was toning things down, which got a swift rebuke, and was told that I was the only lad to have any flair about his dressing, or the courage to try new things. I explained I was only copying girl’s fashions, and she said whatever I called it, if it was copying girls, then I should do more because I looked good. I broke down about this point and told her how I had spent my Christmas as a girl, and that mum wanted me to be one fulltime. To my surprise, as she held my hands and looked into my eyes, she told me I was a girl already, the gossip about me was all about if I was transgendered. This was a severe blow to my masculine side. Even Lisa saw me as a girl. We ended up with a hug and her telling me to embrace it. Being a girl is wonderful, far better than being a macho ignorant lad.
Where would my life go from here? I know I had started dressing differently, but things were moving on out of my control it seemed. Everyone else dictating how I should appear. I tried to recapture the pre Christmas look, androgynous, what mum called femboy, but even then I was not allowed to forget my female status in the house. If I wore tight trousers, and I had a few, and I had not tucked and hidden my boy bits in control pants, mum would point out that girls have a flat crotch. If I tried leaving the house without make up, she would make some comment about how dull or plain my face looked. But the most significant thing she did was to give me hormones. I had always had vitamin tablets from being a child, but after Christmas they changed from little orange ones to white capsules, and I unsuspectingly took them.
Tom played his part in this reinforcement of my changing gender. He and mother must have discussed me, as he became keener than ever to take me out to the gay bar. Which came to mean I wore the wedge heeled boots, full make up and anything else feminine he suggested. He hardly ever called me Mark, unless it was in front of friends who would hear. I had also let him know how much I enjoyed sucking his cock when I licked his cum off his finger, so whenever the opportunity arose, particularly when I was dressed more femininely, I would find myself kneeling before him, accepting what he gave me.
As January changed into February, and then into March, I found myself less able to challenge Tom. If he said we were doing something, I would agree without question. Mum had me doing a bigger and bigger share of the housework, and once again I never complained, just did as I was told. Then at Easter, I noticed my nipples getting sore if I wore anything coarse on my chest. The solution was to wear soft fabrics like satin or silk. The problem with this was the nipple would become hard and stand out. Mum noticed this one day, and as the nipple showed through a thin top and asked how long they had been like that.
I was so busy trying to please Tom, mum and to a small extent Clarke, when he was about that my studies were always in late and rushed. Two tutors made me aware that I needed to pick things up if I wanted to pass any exams, so I tried harder. But to no avail. The end of year exams showed how badly I was doing, followed by a letter asking me and mum to meet with tutors to discuss the results. I was getting more emotional than ever before. When the results and then the letter came, I broke down, I was in bits. My lemon hoodie was wet with tears when mum got home. She held me for an age, saying clichés like 'there there' and 'it will be alright'. Then as I calmed, we talked the results through, and it transpires that I was doing A levels because I thought it was what mum thought was the best. Now she said I should concentrate on being happy, and maybe consider getting a job. This was news to me. I had always thought she wanted me to get a degree, but seems not. We went to see the tutors who either said that my results had been dropping since Christmas and they could see the reason why, or they did not see any sign of improvement, and told me to go and think hard about what I wanted to do in the next year. They all felt I should retake the lower sixth, but I was not keen.
I was down as we drove home. My future was not looking bright, though I had never really considered anything other than taking an easy choice. She broke the silence when she asked if I had an alternative plan to studying. I admitted to not really having a plan, in essence just pleasing myself. But as she had reminded me often, pleasing myself is not always the best choice. I asked her what I could do that might please her. Be contented she said. Then as happened occasionally, the seat belt rubbed across my chest and irritated the nipple. I repositioned the belt so it lay between the two nipples. This time she noticed and asked if they were sore. The change of topic caught me out and I told her they were more sensitive than I remembered which was making me careful. We both looked at my chest together and saw how the belt was nestled between two small but distinct mounds on my chest. Again she broke the silence 'you are starting to bud you know' 'grow a bust you mean'. I asked in a slightly too high voice. 'Yes Marie, you are developing into a proper girl' She paused to let that sink in. 'Now that could affect your plans I think' It certainly could I thought. How could I go back to school to retake any courses if I was having breasts growing for all to see? Being a femboy attracted some teasing and bullying, changing sex could make things far worse.
When we got home, mum had me remove my top and inspected my chest. I felt a little embarrassed at the attention and being naked for some reason. 12 months ago I would not have batted an eyelid about walking around bare chested. 'They are definitely breasts, how long have they been like this'. I told her how the nipples had got bigger and sensitive, then more recently how they had darkened and started to swell. 'Maybe you should start wearing a bra all the time, to support and protect them'. I looked at them, then at her 'Are you sure, they are only small, and I am not a real girl' She gave me a long look 'Small yes, and female most definitely. I think you are going to have to get used to the idea of having a bust'. I asked the obvious question, how? She said maybe I was wanting to be a girl and this was the consequence, or maybe I was a mixed gender, or maybe I had been eating something. I could not think that any applied to me, but did have to accept that some day soon I would not be able to hide these two developments.
As if to compound my move towards fulltime female, that evening Clarke came round. As always mum was looking her best for him. Her mantra of pleasing the man was very evident. They were going to visit friends, but before they left, Clarke gave us both a surprise. He had booked a week’s holiday in London, sightseeing, a show, shopping, whatever. He had booked two rooms, one for him and mum, the other for me. He then added that a double was only a bit more than a single, so if Tom wants to come he is most welcome, that is, if I wanted him along. I meet Clarke occasionally and had got past dressing up for him. I either hid or made sure mum would not complain about my look, so he still thought as he always did, that I was Marie, his girlfriend's teenage daughter. This holiday meant one thing, I would have to be Marie fulltime and fully female. No sign of the femboy.
I had no choice really if I wanted to stay in mum's good books, but I did not mention it to Tom when he came round later. We talked about my poor grades and what I might do in the future, but nothing about sharing a hotel room with him. Mum and Clarke came in to find us watching TV, and the first thing mum asked was 'Has Marie asked you?’ Tom looked puzzled, so Clarke reconfirmed his offer. Tom, who was studying history, said it would be great to look round London. I said an ungrateful 'Oh great' which got a stare of mum, who was later to tell me off for my outburst. Pointing out I should be happy that he wants to come and I should be pleased he wants to share his interests with me. Then she added 'We shall need to take you shopping young lady, trousers are fine for daytime, but I am not going to a show with you looking like a student when you could look like a pretty woman. Think on what you fancy, and if that does not help then think what Tom might fancy you in.' 'Mum' I said 'He likes me as I am, I don't need to flaunt myself just for him' She gave me a long look, then closed the conversation. 'Yes he does like you as you are, but he is a lad and they like pretty girls to look pretty. Besides, he is a good lad and it would be a shame if he started looking elsewhere just because you failed to make the most of yourself. I think I might be repeating myself, but in such situations don't please yourself, try to please your man' and with that got up and went to bed. I sat there considering several conversations and events of the day. I had said I liked to please myself, but that had left me with no future at school. Now I had the words of my mother ringing in my ears, that I should be pleasing Tom before myself.
With six weeks to go before the holiday, and no plans for the next day, let alone the future, I rather drifted for a few days, not knowing whether to go to school from habit or look for work or alternative courses for the next term. Then I had two conversations. One with my mother about what I planned on doing if I was not going to school. The other was with Tom, partly about what I should do, but the subject of the holiday came up and mum's comment about how I had to get myself a skirt, which created for Tom a far less serious subject. He had said a few times before how he would like me to wear a skirt when I was pretending to be a woman, so knowing his wish was more likely to become reality, he was able to tell me what sort of skirts he would fancy on me. Later, I had to admit it was useful to know what he liked, which was fairly standard for a nineteen year old lad. His favourite was short skirts, showing plenty of leg and big heels at the other end. Though he did like a more feminine billowing style which I thought might be more modest in protecting my shaky gender position.
As a week passed and I was showing no signs of doing anything other than nothing, mother decided that I might as well keep the house clean and prepare our meals which included shopping. So I started to get even more domesticated. Cleaning, looking in recipe books and then buying what I needed so I could have a nice meal ready for us when she came home. But this was not enough. Because I was not going out much, I did spend a lot of time in jeans and a top, just being me or so I thought. Mum thought differently. I had time on my hands, so I should make good use of it and I was to present as femininely as possible, she said. So I was ready for the fulltime experience of the holiday, and to this end, when we went to the salon for our regular hair day, she also booked me in for a full set of nail extensions with white french tips. How could I hide them? She knew this and made it clear my appearance should reflect the nails. Stylish lady. Tom was pleased to find me made up that evening when he called to take me out. I even admitted to finding being Marie not that hard lately, and once again found myself knelt in front of Tom licking his prick. But what I noticed was that I never got any reaction from my own prick. Maybe taping it back was making it numb, but I was getting different sensations inside me when Tom stroked or squeezed my nipples. They went hard and something inside tingled.
The Sunday morning after, I was in a nightie eating breakfast with mum, when she asked to see my chest. I blushed and asked why. She was curious if things had changed since our conversation about sensitive nipples in the car weeks ago. I slipped a strap off my shoulder. She was amazed and let out a squeal of delight 'they are fantastic, you must be an A cup at least. Do you like them?'
I was taken aback by her enthusiasm 'not really thought about liking them, but they do fit with my current image, and I know you and Tom like them'
'how do they feel?'
'Well sensitive, the bra helps, but I fear I will not be able to pass as a boy for much longer'
She questioned me again 'Is that a problem Marie?'
'Maybe not for you, but I do still think of myself as part boy at least'
'Even though you look so pretty? They will get bigger you know, then you will not be able to hide them'
'I know, I have been thinking that, what with the holiday and everything you are asking me to do. Whether I shall ever be anything but a girl ever again'
She took her time to reply 'you know what would please me, and I think it would you as well'
I finished my coffee. 'It would certainly be easier if I just accepted I was turning into a girl and got on with it' With that, I swallowed my vitamin pill. Then mum made an odd suggestion. 'While your body is changing, maybe I should look for some different vitamins, or for now you could take two a day, help your system adapt' Innocently I took a second pill and went for a shower, taking a good look at my growing chest and shriveling manhood. When I came out, she was ready for me, and told me as I had decided to accept that I was a girl she was going to treat me to some new clothes. I asked her if she meant a skirt. She said if we saw a nice one, then yes.
What we did come back with was: a pair of flats, a pair of what I thought were sky high sandals, some black leggings and a white sixties style long top, but most controversial was the cream cotton skirt. Soft flowing and just above my knee, it was her choice and I wondered if I would wear it. To please her, I wore the legging and long top when we got home and found the look quite good. My long legs looking even better when I wore the heels and the top looked definitely female. When I went to show her, she smiled and asked if I liked it. I said it was nice and she had got me to wear something totally female again, so I knew she would like it. She agreed that she did like it and hoped I would enjoy looking completely female, rather than there being some doubt about me. We made some food together, drank wine and baileys, having a girlie night in, which seemed to please both of us.
A week later I was stepping out of the shower and caught sight of my reflection in the mirror. It was a brief glimpse but it shook me. I had not fully noticed how my chest had developed, and maybe it was the angle or the light, but my bust was very noticeable. I went to my room for a closer and more intimate look. There was no doubt my chest had changed and there was no way a tight top would not conceal my new shape. They even jiggled if I moved about. Fortunately, mum was at work and I had time to consider what this new information meant. And what it meant was, I looked very much like a girl. Even in a loose top I was aware of my nipples pushing the front out. I spent several hours trying on different outfits, until I accepted that with my chest, I might as well wear a bra and look like the girl I had become. My mother had encouraged me to have my hair done in feminine styles. My whole look was easily female, even if I cut off the nails and hair. I felt that I would be unable to hide my changing gender. When she got home, I had given myself a full make over, mousse in my hair to make it stand out more, full but subtle make up, a bra padded out, but because I knew it would please her, I wore the cotton skirt and heels. She was over the moon when she saw me and as I explained how my day had been, she told me it was for the best and was pleased at my acceptance of the situation
From then on I spent every day being a girl. I was even able to wear ordinary knickers as my male bits had stopped doing anything significant other than allowing me to drain my bladder. A few days after my acceptance, I plucked up courage to call Lisa and ask her to meet. She was used to my femboy styles, but now I had gone completely feminine, I was not 100% sure she would like it. After a few texts, she came around when her classes finished and was delighted to see me. I had spent hours getting ready for her, ending up in the long top and jeans with heels. She was sure this was how I would end up and there had been gossip that I had left school to have surgery, so when I showed her my chest she was pleased to see they had developed on their own. The next thing that came up was my lack of pure girlie clothes. I showed her my skirt, which she declared a mum style. I defended it, saying it was nice and soft. Lisa suggested I just look at what other girls our age wore and copy them to start with. I raised the objection that most teenage girls wore short skirts. Her response was 'So', but she did explain how they also wore thick tights or leggings under the skirt, rarely just bare legs and panties, which made me feel a little better about short skirts.
The next person to discuss my acceptance with was Tom. He had been behind my getting more feminine from the start it seemed. Now he just loved the prospect of me moving on from femboy to chick with a dick as he put it. He also liked the idea of short skirts, but he was a lad and that was to be expected. Never the less, when mum came in to find us chatting, she asked how we were and so on, and Tom let her know how pleased he was that I was going to wear skirts more often. Which prompted her to give me some cash to go shopping with. The only word of advice was that I take Tom, and he must like my choices, otherwise they go back unworn. When I objected that he will have me in short skirts and low cut tops, she rephrased her mantra, 'If you are his, then let him dress you as he likes to see you. I am sure he will show his gratitude if you go along with his preferences.' So that was more or less it. I did like Tom a lot and was almost totally thinking of myself as his girlfriend, the emphasise being on 'his'. So, come the weekend, I was going round the clothes shops with the cash and Tom. We bought three skirts, all short. One pleated, one bubble, one an elasticated tube. We had enough cash left for two tops, a slash neck and a sheer blouse, and one pair of shoes, which according to Tom had to be the highest we could find, which ended up being 5" platforms and made me nearly as tall as him, and certainly slower when it came to walking with him. I was going to get some leggings or tights, but Tom vetoed that, insisting I had such good legs it was a shame to hide them inside thick black socks.
Later that evening, Tom came round to pick me up to take me out for the evening. I was doing the 'keep him waiting' routine and walked into the living room where Tom, mum and Clarke were seated. I got a great reaction to my sheer red blouse, tight red mini, and 5" stilettos. Tom and Clarke just stopped talking and stared. mum got up and led me into the hall
'You told me to let him choose' I got in my defense quickly
'I know, but you do look like you are asking for it'
'I am not that sure about it myself, but it is what he likes, and if he likes slutty on me, then that is what he gets. That's right isn't it?'
'Well. err.... I suppose so, just be careful'
'Don't worry, he can't get me pregnant.'
We started at the gay bar, but moved onto straight ones pretty quickly. I was unnerved by the looks I was getting from men, which made me feel like a piece of meat. But Tom loved having me link his arm. I think he was showing off again. Without saying a word, he was letting all the men know I was his, and I was one hot girl that was not available. We got back home to find the house empty, and though I did turn the kettle on, I was far more taken with the attention Tom was giving my breasts, which were now highly sensitive and with a little encouragement could have erect nipples. Which, as he played with them, made me gasp. I did end up drinking his cum rather than coffee. Thankfully this time without mother walking in on us, but it was close. I forgot to button up the front of my blouse. More telling though was the lack of lipstick and a sticky drop in the corner of my mouth that I licked up as she gave me a motherly, concerned look. I let Tom out the back door then walked through to the stairs to find her and Clarke giggling, but stopped as soon as I appeared. Then starting again when I shut my door. It only took them minutes to be shutting her own door and making noises that correspond with passionate lovemaking, so I did not know what they had against me having some fun.
In the morning, Clarke was there having breakfast so I made an effort to look more Marie than Mark. That was if looking like Mark could be possible. As I dressed I reminded myself I would have to consider myself as Marie all the time and lose the idea of being a lad called Mark. I was wearing the pleated skirt and slash neck top, which got an approving look from mum. 'You look good, going anywhere?' From this comment, I thought that she saw me as dressed up and answered 'Nowhere special, just fancied trying on the new outfit, glad you like it' I spent the day in this short skirt, and in my new frame of mind found it appropriate if a little challenging, as the pleats allowed it to show more of my legs than I really wanted to. Another day of learning to be a girl I reflected on later, as I wondered what else I would need to master as I continued into life as Marie.
Before the holiday happened, I had a few more Marie experiences to live through and learn from. Joan from the cafe rang up in the daytime and asked for Marie. This at first did not make me suspicious till later, when I realised she must have been primed by my mother. Joan wanted to know if I wanted to work at the cafe. When I said I was unsure about it, I did not say, it but I was not that confident I wanted such a public position where many would see me. As I dithered, she explained how she had decided that waitresses should wear a black skirt. I promised to think about it and call her back the next day. She told me to be sure and call, the job needed filling. I was mulling over the significance of Joan's call when mum came home with a shopping bag. She placed it before me and told me to look in it. I pulled out a stretchy black skirt. 'Joan rang me, and said you were undecided........ Well, if you think you're sitting around here all day, and not going back to studying, then think again girl.' I recognised my submission as I sat with my hands resting in my lap and my eyes looking at the floor in front of me. 'I shall go and call her' was all I could think to say. The next day, I turned up at the cafe wearing the skirt, black tights, black ballet shoes and a white top. I was in full Marie mode and Joan told me I looked just great, and was dressed suitably for the job. She gave me a long black apron and explained my duties, but reassured me that if anyone gave me a hard time, I was to retreat to the kitchen and find her straight away.
It did not take long before the tables were filling up and my mind was more on the job, than how I looked. Remarkably, no one said anything that I heard about there being a boy in a skirt waiting on the tables. At least that was what I thought, and when I had finally tidied everything up and prepared for the next day, Joan took me aside to share the tips, I assumed. 'So convincing, I know I expected you to look like a girl, but you are so feminine it is hard to spot anything of the boy in you. I do hope you don't mind me saying this'
'Thank you, I was uncertain about what you and mother had cooked up for me, but I appreciate the compliment.'
'So, do you want a full time job?'
I could have told her I had nothing better to do like a teenage lad, but instead I thanked her and asked if the white top I was wearing was suitable. How femmy was that.
Mum was pleased to have me working, but I was not that pleased to find she still expected me to do a large share of the housework. If I was home first, I was to prepare tea. If I started late, I would have a list of cleaning jobs to do before I left, and that was on top of the effort I took to make myself look my best.
Joan knew about the holiday, so did not object when after a week I had time off. She just told me to enjoy myself. The part timers would cover for me. I felt like I was packing everything I owned as I had no idea what I would need while away. For the journey I chose leggings and my first purely girlie top, the smock styled one. Tom turned up on time, with a small case containing a few clean changes of clothes with not much to choose between them. A far cry from my selection. Clarke drove all the way, a kind of macho thing I guessed. He and Tom discussing football at the front, me and mum chatting in the back, how sexist I thought, but accepted it as I saw Tom enjoying himself being taken as an equal to Clarke.
Once parked and in the hotel, I unpacked and let Tom see what I had brought, then he suggested I wear the pleated skirt as we were going out for a meal. I dressed up for him, later meeting mum, who had dressed up for Clarke with a halter neck dress which only just contained her breasts. Pasta and wine consumed, we discussed where we wanted to go over the next few days. Tom wanted to visit a few museums, mum wanted to shop. I wanted the tourist things like Trafalgar square. But it was later that I really learned what the trip was about for me and Tom. I got ready for bed, going through my cleansing routine before putting on a short satin nightie, emerging from the suite to find Tom already in bed. This was our first time in a bed together, and I was worried, while at the same time excited about the situation. We kissed and cuddled for a bit. His erection free to grow without clothes. I was caressing it when he asked if I would like to try being his woman. I knew what he meant and asked him if he knew what to do. He said he did and massaged some gel into my arse while stroking my nipples. I was really enjoying this until he tried to push his dick into my hole. I knew this was how we would make love and tried to relax. After a little while he got inside me, then after a few painful strokes, he came. He shriveled up and flopped out of my hole, and that was it. We had lost our virginity in a very disappointing manner. Things could only get better I thought.
The next morning I was sore at first, but soon got used to the discomfort as I wore some low shoes and trousers so I could enjoy the museum we would be visiting a little more. Tom was in his element, showing me stuff and explaining its relevance to the important events in history. I must admit to only taking any true interest when I was looking at fashion through the ages and tried to imagine what the women wore. The day finished with another nice meal with wine, followed by a trip to a bar where I drank some more. That night, I was not so keen on my cleansing and changed in front of Tom, who helped me out of the blouse and skirt I was wearing. Soon we were on the bed and having a rerun of the night before. This time I was more relaxed and Tom entered me with more ease and was able to ride me for a while until he was unable to stop himself and exploded into my arse. 'Now that' I thought 'was good, I have been his woman and he has been the man. Mum would be pleased.'
The following morning mum wanted to go shopping with me. She and Clarke wanted to go to a show and she felt I needed a nice dress for the occasion. Once she had me on my own, she asked me why I was walking with more of wiggle. All I could do was keep my arse cheeks together and minimise the soreness. Over a much needed coffee and chance to sit down, mum asked if my walk was to do with Tom. I said in a way which got a smile, 'Oh tell me more' and did not let up until I in desperation I told her we had made love. For some reason, this shocked her. 'What do you expect, double bed and you telling me to make my man happy, it was bound to happen sooner or later' a woman at a neighbouring table looked over with a strange look on her face, so I lowered my voice. 'I do hope it gets more pleasurable with time though' mum in a concerned tone said 'I'm sure it will, took a while before I enjoyed it. You using jelly or a lubricant?' 'Yes mum, can we change the subject' She did onto What sort of dress I was going to get. This was her mission that day, and she made sure I was going to be involved as she walked me from store to store, trying on various styles. By five o'clock, I must have walked miles but I was kitted out for the evening. A candy pink dress with satin ribbon doing a cross over between my breasts so they stood out. The skirt flared out from my bustline and stopped a few inches above my knees. In truth it did feel very feminine, and with the short grey jacket, grey platforms with 5" heels, a small grey clutch bag and some nice costume jewelry, I felt absolutely wonderful. But as far as Tom was concerned, besides me looking so good, was that when he later unzipped the dress, he discovered that I was braless and wearing only a matching pink thong. He was smiling from ear to ear as he took me to bed that night.
Morning again was uncomfortable, but with the discomfort came the knowledge that I had made love to the man I wanted to be with, so it was a no pain no gain attitude. The rest of the week was pretty much along the same pattern. Daytime out sightseeing or some such tourist activity, Low shoes, trousers on occasion, but mostly skirts. Then get dressed up in the evening and go out for a meal. Followed by some sex, followed by sleep. Happily for me, on the Friday night Tom was taking his time and trying to make sure I was enjoying myself when his prick stroked something sensitive inside and I just wanted him to continue. I made him move his position. I moved my position until we had gone in all directions. Then he hit the spot again and I kept him on it. I had wanked before as a boy, but this felt so different, a build up, then a growing sense of tension. Last an explosion inside that went in waves through my body until it finally subsided. When I came down, Tom had come as well. 'I guess you enjoyed yourself then?' Tom teased.
'Thank you, that was brilliant'
'Part of the service, boyfriend, lover and sex toy'
I was too spent to come back at him, just kissed him and went to sleep.
In the morning, mum and Clarke were giving us side ways glances. Eventually, I said 'what?'
'Good night last night?' mum asked
'Yes thanks'
'Thought so, these walls are quite thin'
I blushed as I realised they would have heard me telling Tom to push harder and moaning as I came. How embarrassing!
Knowledge that my mum knew and did not seem to mind that I was having sex with Tom came as a bit of a surprise, but I coped. By the following Monday, I was back in my white blouse, black skirt and long apron, waiting on the tables at the cafe. Besides Joan asking if I had had a nice holiday, no one seemed to be in the least bothered about me. Over the weeks, I would go from wanting to know why I was not being called weird by customers, to wanting someone to say 'you look pretty' and flatter me a little. But life just ran into a routine of work, time at home, and time with Tom. I had become an ordinary girl with an ordinary job. Yes, most people around knew my past, but after the first bit of gossip it all faded and no trouble seemed to follow.
By Christmas, my breasts needed a B cup bra and my hips had filled out a bit, giving me a more feminine shape which pleased me, so I decided that it was about time to face my mum over the future. I started by asking if she had any objections to me seeing the doctor about how things were turning out. Then I asked her if she would mind me getting my name changed legally. Then I asked her if she would tell me what hormones she had been feeding me so I could tell the doctor. Up until the last one, she had been quite positive, but the last one meant she had been found out. I had known for months after checking them out on the internet, then accepting I liked what they had done to me and continued so I could see how much my body would change. I had to give her a hug and tell her I was fine with the drugs and that they had worked a treat, but I would need to know for the doctor. So she told me, then asked if this meant the last days of Mark. It had to come, I told her some things just gather their own momentum, and after a while as the femboy, it was inevitable that I would lose the boy part of me.
I did see the doctor who passed me onto a specialist. I was given a proper set of drugs, which would promote my female body changes. It was decided between Tom and me that we did not want any surgery. For some reason, Tom liked to still see my dick when I was undressed. He said it made me special. I was just glad to not be going to hospital.
My name was changed to Marie without much trouble, and I was able to open bank accounts and get paid as Marie, which at the time felt like a definite severing of my past.
For no better reason than I take the easy option, I stayed on working for Joan at her cafe. I was soon the only fulltimer as the quieter winter season crept up, but she kept my hours up and left me in charge on occasions, which felt very good to my ego.
Tom could have gone to university, but took a trainee job at a firm of accountants, so he avoided debt and could stay near me, which was sweet.
All in all, life as Marie looked to be far less stressful than a life as Mark could ever have been. I felt everything had come up well, even if the journey had been a little bumpy at times.
We all have our fantasises about a favourite dress or situation we might like to find ourselves in. Well, mine is to be taken to a dinner dance by a smart dressed man.
As you might guess, I am not a regular woman. I am a regular bloke who likes to pretend from time to time to be an attractive thirty something woman. But while I am dressed as a woman, I fancy men. Though I fancy women something rotten when I am just a bloke. I had been with Kerry for a year just gone, and she knew about my fantasies. Not that she indulged me, I just felt I ought to be honest from the start. She made it clear that when I was with her, I was to be a man. She did not like the idea of me looking at other men. As she put it, 'that was her job'.
Well, after 12 months of near abstinance, I got a surprise. Kerry had asked me in a drunken conversation what my best fantasy was, so I told her. And she told me hers was to make love on a beach. Within the week, we had fullfilled her dream and made love in the dunes of Southport beach. As we drove home from our weekend away, she squeezed my thigh and told me it was my turn next. I was stunned by this development. She had never wanted anything to to with my dressing, yet here she was encouraging me.
Four weeks later, she confirmed with me my fantasy of going to a dinner dance with proper gent. I nervously said yes, to which she said 'good' rather too enigmatically. I was told to keep the weekend free, as well as the Friday evening. I think you hear me gulp for another country, 'what was going to happen?'
I finished work on Friday, unsure if I should go home. Worries about what she might have planned played on my nerves, but the temptation of finding out what she had in store meant I went home as quickly as possible.
'Strip' were the first words I heard as I walked in the door. I did as i was told and found a long silk wrap to cover up my nakedness.
'Bathroom' was the next instruction. There I found a bottle of Immac waiting for me. I knew what to do. Half an hour later, I was bald from my toes to my head except for a neat bikini patch up front.
'Bedroom now' wrapped again in the robe and feeling it's soft sensuousness on my bare skin. I emerged and went to the bedroom. Kerry was waiting for me, dressed in a plain white T and jeans. 'Feeling good?'
'Umm well that depends' I was unsure if yes was going to be the correct answer.
'Does the wrap feel good on your skin? it does on mine'
'Yes, it feels great'
'Next we need to alter your shape, so you will be unattractive to me. OK?'
'Whatever you say'
'Right then, lay on the bed and shut your eyes' I felt cold glue on my chest and then I was told to hold some false breasts in place. They felt huge, but she assured me they were only a C. Then stuck in that position, on my back holding my tits, I felt something ice cold pressed against my genitals. I almost recoiled in shock, but she put a hand on my shoulder to keep me down. The pain sudsided as did any hope of an erection, as everything retreated from the cold. She quickly spread superglue over my prick and pushed it and my genitals out of sight. My balls had gone inside, and my penis was stuck rather too well inbetween my legs.
'Now then, bra and knickers, then cover yourself up, and we shall get ourselves something to eat.'
I spent the evening in underwear and the wrap. The whole situation was rather strange. Kerry kept her distance. I was clearly not her 'type' at the moment, and I was not used to being dressed in the presence of others. Sleeping was odd as well, no cuddling and relaxing together, when I went to touch her, she quickly rebuked me with a terse 'No'.
After a fitful sleep, I was up first and making breakfast when Kerry appeared in her scruffiest clothes. 'Right, some questions. Can you do your own make up? I don't think you have any clothes suitable....I have looked everywhere, have you any idea what you might like to wear for your fantasy?
This caught me off balance, So many questions.'Yes I have done make up before. No, I binned all my clothes before we moved in together, so I have nothing. In my fantasy, I wear something long and elegant, but the colour and style does change. Any more questions?'
'If you want long and elegant, it would mean you have to be prepared to look your best, and mean your feminine best' she was looking straight into my eyes.
'I know what you mean, the dinner dance is something women get really dressed up for, that is why it is my ultimate fantasy'
'In that case, you wont mind if I tell you I am going to make sure you will be dressed up, your feminine best!'
I was exhilerated and terrified at the same time. I had no idea what she had in mind, just that I was going to possibly have a great time or a nightmare. 'OK, let's start, get your pale yellow T and those tight jeans on, then you can use my make up after you have a shave.'
'Should I wash my hair?'
'Not necessary, I have that sorted for later'. The butterflies kicked in again, that must mean a salon trip. I disappeared upstairs to the bedroom and sorted out the clothes she suggested, then took a longer than usual look at her make up. I had lingered by the mirror before testing her cosmetics, but this time I was allowed. Shaved and ready, I applied the foundation, then a light blusher, some mascara and a thin eyliner. Then to finish, I chose a creamy mid pink a little darker than my own colour. She approved of my chioces, and just blended the chin and neck a little better for me.
'I think I might end up regreting this, you are looking far too good already. Next we need to go out, have you been out before?'
I nodded 'Did for a bit before we meet, used to go to a couple of bars in town.'
'So, how do you feel about shops?'
I swallowed hard 'Prefer not too'
'If this is going to work, you have to. You need a dress for tonight, and it has to fit. So you need to go and try them on really, no good me going alone and guessing'
'Put that way, I have no option do I?'
'Not if you want this fantasy to work'
'Where do you want to take me?'
'Well, we could do the stores, or I know a dress agency, they sell secondhand good quality stuff, that would be excellent'
'And more private?
'No promises, but could be, should I call them and let them know you are coming?'
'Please'
Half an hour later, I was inside a women's dress shop. It was mid morning and luckily empty. Sharon was briefed as to what was going on, no point in her getting upset if she guessed I was not the real thing. I was put into a cubicle while Sharon and Kerry fetched what seemed like endless handfuls of dresses. After about the sixth dress, the novelty was wearing off as I was stepping out of another dress that was too tight/short/long/big or just plain wrong. Then Sharon brought through a deep blue dress, saying how she was not sure, as it was so fitted. But Kerry helped me into it. I stepped into the skirt and we wiggled it up my legs and over my hips. This was where I thought it might be another failure, but it came up and then I got my arms into the sleeves and with a bit more help, I was in it more or less. Kerry asked me to breathe in as she pulled away at the zip. It slowly rose up my back and once at my chest, closed easily, but I was stretching the waist. Kerry was expressing some disappiontment, when Sharon asked me to slip it off to my hips, she had an idea. Being a TV, I knew what that idea would be, a corset or waspie. Minutes later, she returned with a plain cream basque which they fastened around me, then tightened till they were happy the dress would fit.
This time the zip rode up with ease, but I was taking smaller breaths and feeling quite uncomfortable. I walked over to the mirror and realised that though the dress was fitted and looked tight down to the skirt, there was in fact lots of pleats in a rear vent, which allowed me to walk quite freely. I think I was admiring myself too long.
'Excellent, I shall not ask how that feels, but believe me, it looks fantastic' said Kerry. Sharon was muttering agreement. Then turning to Sharon 'I don't suppose you have something suitable for going round the shops, we will still need a few accessories and things?'
'Not a problem, give me a minute' then looking at me ' do you mind keeping the basque on?' I must have had a puzzled expression on my face. 'Gives you a better figure and I have a great size 12 that will look great on you'. Moments later, she was back with a grey dress, bit of a tulip skirt shape and room around the bust but fitted at the waist. Kerry looked at the price tag. 'That is great, we will take it. Leave it on dear. Sharon, have you any size 7 shoes'
'Just these black courts, would you like to try them on'
I was soon at the till as Sharon rang up the items. Not too bad I thought. I was out the door in my new dress and heels, carrying my blue evening dress and nearly at the car, when it dawned on me I had left my jeans, T, and trainers behind. When I mentioned this to Kerry, she just pointed out the fact that I would not be needing them, and could always come back next week for them. I let it pass, but wondered what else she had in mind.
Once in the car and feeling the waspie's constraint making me sit upright, a new set of questions came from Kerry. 'Those heels seem to be OK, how high did you used to wear?'
'over 3"' I amswered
'And a stileto, I guess? Stockings or tights? the basque has loops for the suspenders, you know.'
'I think you have made your mind up already, haven't you?'
'I like to make you feel we are doing what you want though, not just a stereotype. Stockings and blue stiletto sandals, if we can find them'
'that sounds fine' was all I could think to say.
She pulled the car up outside a short row of shops. Heaven was written across the window. 'Well, I guess you know what is next'
I nodded 'Yes'
'The girls here know the score. I have asked them to make you your feminine best. They actually surprised me by telling me you are not their first, but that is by the by. I am going to have a look round some shops to see if I can find some of the other things you will need while these girls do their business, so see you later'
I was expected to go in on my own, it seemed. Kerry made no move to get out of the car, 'See you then'. Yes, I was to go in alone!
My nerves were jangling as the door bell rang 'Kerry made an appiontment for me?' I answered in response to the questioning hello.
'Ah yes, Kerry. Now then let's take a look at you, you are going out tonight and want to look your best'
I swallowed hard 'That is correct'
'well you have come to the right place' and with that, the three girls began chattering about all sorts of things I thought I ought to know about but, failed to understand. My hair was brushed out and held in different positions. My fingers were looked at, my face considered. 'What colour dress are you wearing?'
'Blue'
'That will suit your colouring. Now can we do anything?'
'Kerry said to let you decide, you would know best'
'In that case. Come on girls, we have work to do!'
The first thing was a hair wash like no other, the scalp massage was lovely. There was more than shampoo and conditioner going on, but it was too late to start putting limits on what they could do. Then, as one cut and rolled my hair into rollers, another was giving me a manicure. Then into a dryer and I thought it would be just a quiet magazine reading time, but the manicurist came back with a trolley, took my left hand and started working the nails again. It was as she placed the false nail over my own that I realised what was happening. With all ten nails fixed, she filed them into ovals and painted them a rich pink. By the time she was done, the dryer was finished. so back to the chair. The rollers out, I could see my greying hair was a dark blonde, and full of body. It used to just touch my shoulders, no longer. It was brushed and sprayed, then brushed again. They tongued and sprayed until they were happy. I had a straight fringe, which contrasted with the mass of curls that covered the rest of my head.
I was looking at myself in the mirror 'I do hope you like it?'
'Well, quite different to what I am used to'
'Oh everyone says that when they try something new. You ready for us to finish you off?'
'Oh, I thought that would be it'
'No, we think some long ear chains hanging below the hair, and could we do a few things to your face?'
'Like what?' I asked
'If we tell you, you might say no, and then you would not look your best'
'If you are sure it will benefit me, then Okay'
'Right, come over here and let Chardonay do you. Now close your eyes.
I felt a tug at my eyebrows and knew I was being plucked, but I was in too deep now to stop. Then after a facial cleansing, she reapplied make up. Before I could look, all I was aware of was my eyebrows and a tingling on my lips. Eventually Chardonay stepped aside from the mirror. OMG, the sultry eyes, narrow brows, much fuller lips in a matching pink to my nails. I looked incredible.
Someone had given Kerry a call and she soon turned up, as if on cue. She took a second look before recognising me. 'Well done girls, a definite eleven out of ten here, I think!'
Soon I was outside and feeling a real buzz from the way I was looking. Kerry spoke up 'Right, you need a bag. Shoes and stockings I have picked up. I see you have gold ear rings. Pierced or clip on?'
'Pierced' I replied
'Ow, that was not on my list, well done' We drove a little way until she broke the silence. 'Enjoying yourself?'
'Well, it is still rather nerve wracking looking like this, but it is always something I dreamt of, so yes, I am enjoying it even If i don't appear to be.'I paused 'How are you finding it?'
'Rather wierd' she replied. 'I am not used to seeing you like this, and it is a little unsettling that you look so good as a girl. I do check around at how people might be reacting to you, and no one is staring or pointing. Here we are, now a challenge for you. I saw some shoes and a bag in a shop on the high street down here, you are going to have to walk there and try the shoes on. Ready?'
'As ready as I ever will be'. She parked and got the ticket, then I had to face a street full of people. Remembering how she had told me I looked good, I tried to be confident and remember my heel walking skills from the past. Soon we were looking in a window. Blue shoes, covered toes, ankle straps, at least 4" thin heels, narrow platform sole. Fantastic. Inside, she asked for a size 7 and the assistant brought a pair. They fitted well enough, then a small clutch bag to match and we were done there.
It was getting late in the afternoon and the shops were starting to close, so Kerry took the decision to head for home, reassuring me if I was short of anything we should be able to find something among her things. But all she could think of was jewelry. By six, I was walking back into our home looking very different to the way I looked as I had left in the morning.Kerry was commenting on how well I was walking and holding my frame, and was rather worried, as she was finding it difficult to recognise the boyfriend she was used too.
After a coffee and a snack, 'Time to get you sorted'. I went to the bedroom and slipped out of my day dress and shoes. The blue dress hung on the back of the door. I was beginning to doubt this, surely this was not reality, but a proper dream? Still clad in my basque, she handed me a satin bra to support my additions, then a matching thong, the string sitting in my crack reminding me this was real. Then the finest sheer stockings, no seams or dark heels, just high quality. I caught a glimpse of my reflection, and was astonished at how good I looked.
'Ok, so you do look good. Let's get on with finishing the illusion that you are not quite what you appear to be. The dress next.' Yes the blue dress next. Again I had to wiggle it past my hips, then let Kerry zip me into it. I struggled with the small buckles on the sandals, but I was soon standing and feeling the soft smooth inner skirt moving over my bare buttocks, and the hem sweeping around my feet.
'To finish you off. A lipstick. Apply it, then into the bag. Moblie in the bag. Small brush for emergency repairs.' Then she just started picking things up. Scent. I sprayed it on my neck and wrists. A gold necklace and a big gold bangle of hers. Then a woollen wrap for my shoulders. Last, to my shock, a tampon. 'Every girl carries one' she told me. Then a condom. 'does every girl carry one of these?' I asked. 'Every girl as good looking as you, should' was her reply. My fantasy had never been sexual. Kerry had assumed that, for some reason, and I was wondering what these items meant not only to our evening, but to our relationship.
It was in those dying moments of getting myself ready that I finally plucked up the courage to ask who I was going to be sharing this fantasy with. Kerry took a seat and asked why it had not been one of my first questions, which rather stumped me. Why indeed? Surely anyone would want to know who they are going out with, especially in this situation. The wrong 'date' could be very embarrassing for both of us. I told her I trusted her judgment, which was a compliment and a good get out. So there I am, fastening the clasp on Kerry's small watch and listening to the details of my partner for the evening. Mark is a gay man from Kerry's company. He is mid 30s, sporty, intellegent and Kerry likes him. I sense she would fancy him if she was not a female. Well, they had been chatting one lunch time about a charity dinner dance advertised. Mark was saying how he had a full kilt that would be great for such an ocassion, but he was single at the time, and besides, he would feel uncomfortable as a gay couple in such a situation. He felt it was a very traditional atmosphere. So Kerry had set me up with the fantasy becoming reality and Mark was quite happy to be my partner, with one condition. If when he meets me, I look like a bloke in a dress, the night is over. His decision is final. So Kerry had it all set up for Mark to come to our house about 7.15, with a taxi booked for 7.30 to take us to the hotel where the dance would be.
Mark arrived by taxi at just after 7.00. Kerry met him at the door and took him into the lounge, then ushered me in to meet him. I was so nervous, everything hinged on this meeting. I felt that I was convincing. Kerry told me I was, but I was still sick with butterflies. I walked in, his back was towards me, as he was looking through the CDs. I coughed and said 'hello Mark'. He turned, he was quite handsome and in the kilt, very smart.
'Rachel?' he asked in a very deep, rich vioce
I smiled 'Yes', then not knowing what else to say, 'I hope I am good enough? will I do?'
At this moment, Kerry walked in with a bottle of champagne and two flutes full, gave us one each, 'stunning isn't she'
I drank mine after Mark had agreed, with the single word 'yes'. I was going to a dinner dance with a handsome man, this was brilliant!
I emptied another flute and made some small talk with Mark and Kerry before our taxi arrived. Mark went first, Kerry draped the pishmani over my shoulders and kissed my cheek in a girlie way. 'Have a good time Rachel'
I hugged her back 'thank you'.
Alone in the car, we talked about our backgrounds and current jobs. He was a technical sales executive, very nice I said. I told him I worked in a call centre for a bank, 'Interesting?' he asked 'Not often' I replied. The taxi dropped us at the hotel reception. Mark was a gentleman and took my arm as he escorted me to the function room. I was on a real high, especially when he told me me I walked with an elegant poise. I was not the only person there in a floor sweeping dress. There were quite a few shorter cocktail dresses, but the long dress was my dream length so I was happy to be in a minority. But not as small a minority as Mark, who was the only kilted man in the room. This did rather attract attention, but thankfully towards him, and not me in particular.
We found our table, a small group of six who knew each other took up the other places, so we were left to ourselves pretty much, though Mark was very relaxed and found it easy to talk with the others on the table, he never once let me feel forgotten. I knew I looked the part, but was unsure of my voice, so kept quiet and told the others I had had a cough which made my voice hoarse.
The food was excellent, the wine great, then we got to the dancing. I had done a little ballroom, but told Mark he would need to guide me as I had never danced the woman's steps before. With his hand in the small of my back, I soon picked up what I was supposed to be doing. After a couple of dances, I was relaxed enough to be enjoying all the sensations. The long dress swirling around my legs. The heels making me dance on my toes. Mark's hand firmly pressing on my back. My manicured hand resting on on this handsome partners shoulder, and him so close, and he was mine for the evening. It was a dream come true.
By the time one o'clock came around, I had danced many dances, drunk far more wine than usual,and found out so much about Mark that I hoped we could remain friends, as he was such delightful company. I was on cloud nine as we danced our last dance, enjoying my final moments in the dress. 'Rachel can I ask you something'
'Of course' I replied into his very close ear.
'I have really enjoyed tonight, I was not so sure when Kerry was setting it up, but I am glad we did this'
'So am I, it has been brilliant'
'I am just wondering....how far does the wanting be taken for a woman go?'
'?'
'You clearly enjoy looking like a woman, being treated as a lady tonight was special I can tell, but do you want to be a woman in any other ways?'
'Oh Mark. This has been a wonderful night. Right now you are making me feel like a woman. I have loved being your partner, but even though I say I feel like a woman in your arms, you must know that I am fully female'
He did not say anything more, the band stopped their last tune and we broke. Mark kissed me on the lips and said thank you for a lovely dance, then took my hand and lead me back to our chairs. The night was most certainly coming to a close, as the main lights came on and everyone started making their way to the entrance. He draped my wrap over my shoulders, ready for the evenings chill air, then took my hand and lead me out to the row of waiting taxis. We found ours and were soon on our way.
'We are going to your place?' I asked, as I recognised the streets.
'Yes, that is if you want to. I arranged with Kerry that you could, as it would be late. Do you mind?'
'Well errr no, I suppose not'
'Be nice to have a nightcap together' he said as his hand let go of mine and stroked my thigh. 'Well then, here we are'. He paid the driver then lead me up the drive to the front door. It was a rather nice house, a little big for one man I thought, but it is probably an investment I thought.
'I'm having a whisky, what can I get you?'
'Do you have amaretto?'. Soon I was sitting beside him, sipping my almond flavoured drink and wishing the dream would never end. His arm over my shoulder, soft jazz playing in the background. I truly felt like a woman beside a man.
'I had better be going'. I said, hating myself for saying it.
'Why?'
'Because I need to be getting home and back to whatever is supposed to happen tomorrow'
'Well, I have an alternative. You stop here the night, and we see what a beautiful woman and this man can get up to. How does that sound?'
'but' was all I managed to say
'Then it is decided then. You go upstairs, I am right behind you'
I had some idea of what he meant, because in some of my fantasisies, I would end up in bed with with my 'man'. I was looking around his bedroom, an enormous bed, black satin sheets, big mirrors. This was a sexual playground.
'do you like it?'
'Erm... not what I am used to'
'Would you like to get used to it?'
'Mark! behave, you know the truth about me'
'The truth being I have just spent a great evening with a fabulous woman. And in those situations, the woman ends up waking up in the morning next to her partner. Have I not quite got this right?'
'I thought it was just a dinner dance'
'And what is wrong with a man taking a beautiful woman to bed?'
He was holding me close, and finding the top of the zip, I felt it release as the tag rode down my back. The dress lay at my feet.
'Every man's wet dream, stockings, corset, heels. Now do you have any way you would like me to make love to you?'
I hesitated.
'I am your first. That seems unbelievable when you are so pretty'
'I did blow a bloke a few years ago' I was trying to find my feet on an ever changing surface.
'And?'
'It was a few years ago'
'Well, this time I think you should enjoy the full pleasure of being fucked. Hopefully I will make you want to not leave it a few years before you want sex again'
A hand strayed to my privates. 'Excellent, you prepared yourself well. There is no way your true gender can intrude on our fun'
I am not sure when my limited resisitance crumbled, but I remembered the condom and in asking him to put it, on gave him the green light to start lubing my arse and get very excited about what was going to happen with his hard on.
Thirty minutes later, I was laying between the sheets, exhausted from the excitement of a very different orgasm. Not a quick explosion. Rather a slow build, leading to a crescendo and wanting Mark to just keep on sliding in and out of my arse.
'Better than your last blow?'
I snuggled up to him 'What do you think?'
'I think you liked that enough to have been converted'
I did not like to agree, just in case it was true.
The next thing I knew was that it was light, and I was on my own in his lovely bed. I could hear vioces downstairs, so I got up and went to the top of the stairs. It was Kerry and Mark.
'Yes, we had a lovely time at the dance' Mark was saying.
'I told you she would be good'
'And you were right, she is beautiful'
'Does she make a convincing woman?'
'Very, no one picked it up I'm sure'
'And later?'
'Pardon?'
'Well, you did not bring her home'
'Yes, she was good in many ways'
Then I must have moved or a board creaked, Kerry looked up. 'Well someone looks as if they had a good night. If a picture tells a thousand words! Come and join us Rachel'
Still in my underwear but barefoot, I walked carefully down the stairs.
'And that tells me where you slept last night. Was it good?'
I blushed. She was not supposed to find out about that part of the evening.
She continued. 'Well Rachel, be a love and go make me and Mark a coffee. I have some things I want to talk with Mark about, that I dont want to worry your pretty little head about them, so run along dear.'
Without thinking, I went into the kitchen and after some looking, found the things needed to make the coffee, even a tray. So with everything set out, milk in a jug, even saucers under the cups, I carried it through.
'Perfect' said Kerry
'Thank you' I said, and did a mock curtsey.
'Even better. Now then Rachel, I have had a chat with Mark and we have come to an arrangement'
I went to sit, but Mark spoke up. 'No, you will stand!'. Something had changed in this room, but I was not quite sure what. Mark continued. 'Rachel, I had a fantastic night last night. You don't know how much it means to me that you enjoyed yourself as well.Well, it would seem my affection for you has rather altered things between you and Kerry'
Kerry jumped in. 'Good god man, get on with it. To cut it short Rachel, you seem to like being Rachel just a little too much for my liking, and as for letting him screw you,,,,,, well there is no way I want you in my bed again'
'But you gave me the johnnie' I protested
'It was a joke, I always take one when I am on a date. Anyway, you have had your fantasy and you liked it.'
'But Kerry......'
'As they say, you made your bed, now lie in it'
'Rachel' Mark was addressing me 'I know this is all rather sudden, but I have space here, and would love it if you would stay with me. Kerry has made it rather plain what her position is, but I would love for you to fulfill one of my fantasies and live with me'
I was really confused now. 'Kerry, please' I went to touch her.
'Piss off, I only do men. I think you should accept Mark's offer. I have discussed your future with him, and as far as I am concerned you are staying here. I had brought your dress from yesterday, so you had something to come home in, but I rather think it is going to get a little more wear than I thought.'
I was beginning to tear up. 'Mark, are you sure about this, we hardly know each other'
'I know enough about you, you are one beautiful T girl and I think that after I satisfied your fantasy rather well, I am hoping you will go along with mine'
'This is good, Rachel' said Kerry 'You will like it and on your behalf, I have agreed to it'
Mark blushed a little 'I have always wanted a maid'
'You want me to be your maid?'
'Yes please' said Mark.
'I could agree to that'
'You have not heard the best part of his fantasy' injected Kerry 'He doesn't like your false tits'. I must have looked puzzled. 'He would want his maid to have real ones, and a rounded butt'
'But I can't do that'
'I am afriad you don't have any real choice. Mark wants you, I don't. You will look riduclous as a man right now. As I said before, we have agreed on this for you'
'But my job, my clothes, my life?'
'I reckon your life here will be much better. You were only saying last week you needed to look for a new job after they turned your promotion down. Your clothes I will sort out, and your life is TV and work, your friends wont miss you, I bet'
I was properly crying. Mark came and put his arm around me 'I want you so much!'
Kerry went off and came back with a drink for me. They sat me down and encouraged me to drink, then things went a little fuzzy. The last words I heard were 'It's for the best, she was a crappy man anyway'
I shall let your own imagination take you beyond where the story ends here.
I came home from work to see the dress hanging on the back of a door.
'Wow that looks the business, real vintage I take it?'
Pam said nothing, I fingered the edge of the dress, 'it feels like real silk, you will look great in it.' I said confidently.
'Do you know nothing, look at the size of that waist, it is impossible.'
'Are you sure?'
'Dead sure, they even sent me an authentic corset to go with it!!'
'Still it will look great.'
'Which part of this are you missing buster, I am not being trussed up and paraded for no one.'
I tried some flattery and nice words but I was getting no where, she was not going to wear it.
'But dear we have spent so much on the outfits and there is only a week to go. You seemed so keen on the idea when Kay suggested we go to this party in vintage gear.'
'Well I am not now, certainly not in THAT.'
'Come on just try it on, see how it looks.'
'I have a better idea, you try it on, see how you like it, god knows how those women put up with corsets.'
Well that got my back, she had challenged me to do something I thought reasonable for her, and being equal in everything I rather had to accept it, besides I do rather like the feel of silk, but you know how it is, men don't do silk.
First I had to strip to my briefs, then step into the dress, that felt nice and sensual with the silk riding over my legs. Pam took delight in telling me that the zip would not close and guessed I needed to loose at least 2" from my waist. Soon I was being wrapped in the corset and Pam was working the laces steadily tighter. Maybe male arrogance or not wanting her to see she might be right in her opinions about corsets but I said nothing as she brought my 30+ waist down to 28" and then 27".
'Now we have a hope of the dress fitting.' She declared.
It did, just, I stood proudly wearing the vintage dress 'so if it looks good on me and fits then it will only look fantastic on you.'
'You really don't get it do you, that corset is horrible.'
'A little uncomfortable maybe.'
'I bet you can hardly breath?'
'No it's fine' I lied.
'Right well in that case, keep it on for the evening, I was making lasagne for tea, slip the dress off so it doesn't get spoilt put something else on and we shall see how you like it after an evening.'
'Fine' I had to lie or expose the previous untruth.
The corset had stiff bra cups which made my tee shirt stand out and my jeans most definitely needed a belt to hold them up, but worst of all was the way I was limited in movement, I could not bend naturally and had to find new ways of sitting, picking things up and reaching my feet, but I dare not say anything.
The lasagne smelt great and as I sat straight backed on my chair I soon realised that I was feeling full well before I was half way through my meal, the wine helped wash it down but I had to give up in the end.
Pam with a look of pride 'not so keen on the corset now I see.'
'You gave me a rather large helping actually and you were only saying the other day that I am getting flabby.'
She smiled 'If you say so dear.'
So as not to loose face I never once let on how uncomfortable I was, I just sat at the computer very upright and when I came to relax and watch the late news the corset would not allow me to slouch back into the cushions, I sat back but still straight backed as I ate my supper.
Eventually Pam asked if I would like some help getting it off before sleeping, I hope I did not come across as too eager but it was a relief to allow my stomach to spread once more. But before I could think my weird evening was over Pam whispered, (why there was only us in the house), that she found me dressed in the corset arousing and quickly had me aroused as well, lying on my back licking her delicate bits while she tickled mine to make sure I was still interested. This was a new position for me and virtually pinned under her so when she came I could do nothing but get her juices all over my face as she sat on it. I have never been in a situation where she has come and not me, but as she dismounted and cleaned herself up the body language was not good. So I cuddled up to her but was pushed off with a 'sorry dear I am tired, you were fantastic though, love you.'
The next day I called in on Steve on my way home. Kay met me at the door, 'Oh hi Mark, I hear you are about set for the party.'
'Oh am I ?' wondering what Pam might have said.
'Oh yes she tells me you have a nice figure.' Now I was worried what they had talked about. 'go in Stevie is just making the meal.'
I walked into the kitchen to see my mate standing on high heels and though I could not see it I was sure he was wearing a corset. 'Steve!'
'Hi Mark, sorry bit busy right now, beer in the fridge if you want one?'
'Steve the shoes?'
'Well I did question them but if I am going to have to wear them, then I am going to need a bit of practice.'
'But why?'
'Oh come on I heard about your fun last night, I was not going to do it but Kay told me you were so I had no choice.'
'I don't remember agreeing to anything.'
Kay was behind me 'Pam seems to think you did, you never once complained about the corset or dress, she even suggested you were a bit sexy and satisfied her lusts.'
Stumped 'well er yes that is nearly right.'
'Stevie, I will watch the food you go and show Mark your dress.'
We made eye contact and Steve teetered towards the door 'these things might look good but they take some handling.'
We walked to their bedroom and draped over the bed was a selection of dresses
'Oh Steve what have we got ourselves into?'
'I thought you knew, remember our holiday two months back' I nodded 'was great golf' another nod 'well Pam and Kay were not to chuffed with our choice or resort.' I nodded they had made that clear at the time 'well this apparently is pay back, they did something we wanted and did not enjoy, this time we are going to a Glen Miller big band night which is not quite rock and roll but so we don't enjoy it they have come up with the twist of putting us in dresses.'
'I get it, and last nights performance was just to get me into the dress, well you say they think we will not enjoy ourselves?' Steve's turn to nod 'well how about we make out that we are maybe not keen but interested, curious, willing to try new things, but not fighting and complaining like they did. How does that sound to you mate?'
'I had thought the same sort of thing, I mean have you felt the lining of this dress, absolutely gorgeous.'
'Ok Steve no need to go over the top.'
'No I mean it, just feel this.' He offered me the dress and I had to agree it was best described as luxurious.
Trying to regain some manliness 'right so we just make out like it is fine with us and take whatever they throw at us without objecting.'
'Sounds like a plan to me.' It just did not seem quite right when Steve said it in his heels, a long green dress in his hands and holding himself rather erect.
I was not sure what the welcome at home would be so went for the cheery 'hello dear, you had a good day, approach. To be greeted with a 'oh absolutely exhausting, would you be a sweet and get the meal started.' She was sitting in the lounge, feet up, glass of pino girgio in hand. Then came the bullet, I gave her a kiss and she told me that making dinner would help me feel my inner woman, 'oh and by the way, I got you some shoes for the party, just check they fit will you.' I remembered the plan and quietly went to start dinner in my new shoes. Maybe I am a natural but walking on my toes came easily and by the time I was carrying two plates to the table I felt reasonably in control.
'You seem to have taken to the shoes.' Pam was recovered and able to flatter my attempts at walking.
'No problem really, just need to be aware of the balance.'
'I was hoping you would take to them, Saturday is going to be fun.'
'For who?' I asked not sure I should have asked.
'For me definitely, I am not sure you will share my fun.'
'Depends how the day goes.' I replied thinking of my plan to not let her get the better of me. It was now Wednesday and followed it up with 'I supposed there are only two day left before Saturday now, anything else I should be trying out before the big day?'
'Well you should be in those heels every chance you get, and it would be good if you shaved before Saturday so the skin can recover, and maybe wear a skirt so you get used to handling one. Is that enough to be going on with?'
'If you think so dear.'
I rang Steve on Thursday evening as I cooked dinner while wearing the heels, corset and a full knee length skirt. 'How's it going with you?' he asked, so I told him of my current situation, I was shocked when he told me that he was fully dressed, make up the lot after asking a similar question to mine but Kay took it further than Pam. He even expressed his pleasure at wearing stockings, telling me I will never forget the first time I put them on. At the back of my mind I was getting nervous about my plan to take this on without objecting, I had never thought of the possibility that it might be nice.
Friday and on getting home from work Pam is terribly excited, 'Kay and Stevie have invited us over for a meal, good job you shaved in the shower last night, now I have sorted out some clothes for you to wear, I shall be up in a minute, you get changed and I shall finish you off.' I got a big kiss of someone who was buzzing. I just fed of that and went upstairs.
Lay on the bed was one of Pam's blouses, not just any old thing, but one of my favourites, most of it sheer and with huge sleeves. Clearly this is what she meant for me to wear as there was nothing else out besides a skirt and other female items to make up my change of clothing. Fifteen minutes later I had squeezed into the corset, discovered the pleasure Steve had talked about when I rolled the stockings up my shaved legs. I was just fastening the tiny buttons on the blouse when Pam appeared 'oh before you do that I have some thing special for you, undo the top buttons please.' A few minutes later the cups on the corset were filled with silicone breast look-a-likes and my chest looked and felt way too large for my regular male ego. But more was to come, she sat me down and carefully applied cosmetics to my face, followed by a wig she had. It was now that she opened the door which has a full length mirror on the inside. 'You look quite the lady I reckon, what do you think Marcela.'
'Who, oh I get it, sorry I just rather expected to look like a bloke in a dress, but....' my words tailed off as I touched the long hair, saw the billowing sleeve hang below my arm, ran a tongue over my creamy lips, put a hand to my now full chest. Pam came up behind me, pulled the hair off my neck (like I do to her) and kissed just below my ear.
'Well you can stand here being all narcissistic, but I want to see if Kay has outdone us with Stevie.'
Then the reality struck me, I would have to leave the bedroom looking like this, I had only been downstairs in heels and skirt before, now she wants me to go outside. Her words brought me back to the world of reality 'here you can borrow this coat and I have emptied your pockets and put the bits in a handbag. And don't worry you look fantastic, I bet your mother would not recognise you.'
'She is dead'
'Sorry, you know what I mean. Come on I shall drive, I know we normally walk but I think you might feel better in the car.'
I shrugged the coat on and took the handbag, all the while telling myself 'I can do this, I can do this, don't let her see how worried you are.' She took my hand and lead me out of the house and to the car. 'Easier if you sit first, then get the skirt and swing your feet in.' That manoeuvre done 'the seat belt can be tricky now you have tits. Right, off we go.' She slipped her hand off the gear lever onto my stocking covered knee and stroked the inside of my thigh 'I think I quite like being a lesbian!' Said with more enthusiasm than volume but I knew she did from the sexual encounters we had had all week, only one of which had included me penetrating her.
Kay opened the door to us wearing a pretty pink dress, kissed us both and took our coats, Steve was in the kitchen wearing an apron over his long summer dress, his vintage dress was long so I suppose it would help him get used to the style.
'Hiya.' I greeted.
'Oh hi, was hoping you would be done up as well, might have been awkward just me in a dress.' He finished what he was doing and took a proper look at me. 'fuck me Mark you look fantastic, has anyone said you make a cracking girl.'
'Well not until now and just for the record no you cant fuck me.'
Unfortunately just then Kay and Pam walked in on us 'Why cant he screw you, a good looking bit of skirt, I bet before Kay was about you would have been fair game.' Pam had a big smirk on her face while I squirmed at her comments 'and Kay you are so right Stevie does suit long hair, hope none of it is in the food, eh Stevie dear.' Steve deftly flicked the hair over his shoulder and went back to his pans. Kay left us, retuning with champagne cocktails fizzing in flutes. This was going to be all about being feminine I had realised way back but standing by a pretty Steve, drink in my hand and feeling the suspender riding over my arse cheek I had to ask 'so how is our plan going?'
'You in stockings or tights?'
'What, stockings.'
'Tights for me today, I prefer stockings, easier to get on and a nicer feel.'
'You are getting into this aren't you?' He would not look me in the eye, 'you are, you like this don't you.'
'Well it does have some nice bits, and take a look at yourself, checking yourself out in the mirror over there and posing in those heels, just how high are they?'
'They have a raised sole which makes them look higher.' I defended.
'Still 5" at a guess, and the stockings? did they feel like I said?'
'Ok ok you win, there are some nice parts to this. Now go easy on my servings I am in the corset tonight which is not one of the good bits.'
We were starting to relax now 'well it does stop you eating too much but what a figure and you have that great erect posture.'
'Stop looking for the positives and let me help you.'
Later on after the food was eaten, the champagne finished as well as a bottle of white we were getting ready to leave.
'Oh I am so sorry dear, you wont mind walking home, I don't think either of us is fit to drive.'
Merry and with inhibitions down 'anyone would think you planned this evening.'
'Well we had to have a rehearsal for the party, and I wanted to see Stevie here and Kay wanted to meet Marcela, and it would seem our new girls have enjoyed themselves, so planned or not I think it went well.'
I laughed 'well thanks for the confession but I only meant you planned to drink and walk home.'
In my normal shoes the half mile is not far but the heels were making it an effort, but I could not let Pam see I was struggling, besides which the cool air on my legs and the tap-tap of the heels on the pavement where a new pleasure previously unknown to me. Another new pleasure when we got home was making love while dressed as a woman, lipstick to lipstick and then once fully aroused I even allowed her to press her vibrator into my hole while pleasuring hers with my tongue and fingers. I had to admit it was a new experience and one I might repeat, but Pam was more positive and made it clear she would definitely be wanting more.
After cleaning up before going to bed to sleep she gave me a long satin nightie 'to keep me in the mood' she said. It was a good job I was tired, the satin is a very sensuous material when worn against bare skin especially. With the party coming that evening Pam felt it would help if I kept in character and lent me a skirt and blouse for the day, then gave me a quick lesson in applying make up and fixing the wig before writing out a housework list for me to do while she had a few bits to shop for and an appointment at the hairdressers later. On taking a good look in the mirror once I was alone I could only think 'housewife' as I took in the plain cream blouse and modest brown skirt, I even had kitten heels on to save my calves she said. Well I was not about to go and ask Steve if he fancied a round of golf or a pint in the pub at lunchtime so I set about the housework list, very aware that I was doing Pam's usual jobs while looking like a wife. I did not call Steve but he called me, asking how I was doing, turned out Kay had done the same to him and he was playing housewife as well, but he had finished and bravely suggested that housewives meet up for a coffee and he would pop over if I put the kettle on. I did think he was mad, daylight, on his own, on a weekend when lots of neighbours are about. But fifteen minutes later his car pulls up outside and my pretty mate walks confidently to the front door.
'God that was a buzz!' where his first words as I let him through the door.
'Anyone see you?'
'I think not, but who would know?'
'Well it is your car, anyway you are here, tea or coffee?'
We were soon sat at the table drinking and eating biscuits, once again reviewing our situation. Steve was telling me all about how Kay had glued breasts to his chest and taped his male bits so they face backwards, I nearly asked how he peed but it was obvious, he had to sit like a woman. And when I thought about sex and his cock being unusable I remembered my own lovemaking from the night before and wondered if Steve had been inside Kay since this started.
We were startled by Kay and Pam arriving together while we were thinking the coffee break was over and we should be getting back.
'So this is where you are.' Kay asked Steve.
'Yes this is me here and not at home.'
'wow that is fantastic, you drove here all on your own.'
'How else?'
'Just making sure.'
I tried to change the subject, 'Your hair looks great, it will be just right for tonight, I guess you have been getting a dress as well.' I pointed to the bags they were carrying.
'Well we couldn't be outdone by you two, could we?'
'Cant believe you went with the peroxide blond though' said Kay.
'Why not, make a statement.' Pam laughed and put a hand to her lacquered and stiff hair.
'The lacquer does feel odd doesn't it, not a hair out of place and stiff as a board.'
It was Steve who asked but I would have done if he had not beaten me to it 'So come on what do the dresses look like?'
'Should we show them or make them wait?'
'Wait I think, how about one of those cocktails, a bite to eat and then we get ready.'
'Sounds good to me, Stevie be a love and slip home to get your outfit and make up, it will be fun having one big getting ready session.'
Steve left, I was making some butties, Pam and Kay were fixing the drinks. I was able to hear the girls talking in the other room and I soon realised they were talking about me and Steve. Our plan to make it look like this cross dressing did not bother us might be back firing as both women seemed to think they had found some latent fetish that we were now exploring and enjoying, while they were loving the developing relationship as we became more feminine. I missed the last part as Steve returned but I got the feeling they were discussing how far they might get us to go with this new found interest.
Those bags did not just contain their outfits, they also had some new 'delights' for us. After our snack Pam and Kay took over our immediate needs as they prepared us and themselves for this 1940s party. Pam was doing make up, Kay was doing nails, theirs were already done at a salon but we were not going to miss out and glue on nails were painted pink on Steve, red on me, matching our lipsticks. Something I would have liked to object about was the plucking of eye brow hairs, I had lost a few during the week but this was wholesale slaughter of my brows, or so it felt. But I was sticking to my plan of not showing I was bothered and just let her get on with her painful plucking. Kay took on the role of hair stylist and moulded our wigs into similar styles to theirs fixing the shape with pins and strong hold spray.
Over an hour after starting if anyone had peeped in on us they would have seen four women in their underwear, sipping champagne cocktails and apparently enjoying themselves. I was rather glad that sometime earlier Pam had suggested that we copy Steve and tuck my male bits out of sight, because now the tape was stopping any embarrassing erection as I in the company of two women dressed only in bra, knickers and stockings, even Steve looked sexy in his corset and stockings and full make up.
It was now time for the final flourish as we stepped into our dresses
Pam had the tightest fitting dress I could imagine making her curves look even better than usual.
Kay's dress left no room for imagination when you looked at the stiff fronted dress, from the look on Steve's face I could tell he was approving of what he saw. The only thing that detracted from the beauty was the length of the skirt, but it complimented Steve's full length dress.
He looked fabulous and it was not hard to tell he was relishing the feelings of his outfit.
I was trying to appear ambivalent to the wonderful dress I was now fully prepared and able to look the part of a 1940s woman.
While trying to appear unconcerned by my appearance I probably gave myself away by checking the seam was straight in the stocking when I slipped into my heels and fluffed out the layers of underskirts to make the dress lie right. Nothing was said but there was plenty of giggling as we waited for the taxi to turn up and take us to the hotel where the party was being staged.
We behaved in the taxi as we squeezed the acres of fabric into the car, had a nice moment when I shrugged my jacket off and a man on the cloakroom smiled at all four of us and told us we looked fabulous and would be sure to have a good night. That was the first stranger to comment on my appearance, and being so positive boosted my confidence wonderfully.
We found a table and Kay bought another bottle of fizzy wine while the band were getting warmed up, but Pam fancied something stronger and bought four shots which were drunk in the usual act of bravado and swallowed in unison. The band soon started followed by the dancing, at first it was just Pam and Kay together, but soon they had dragged us onto the floor. It took a while before the first invitation to dance arrived which Kay accepted. Soon Pam was dancing with a man also. Me and Steve had a quick conference about what to do if we are asked to dance, Steve said stick with the plan of not appearing to be bothered, I was more nervous as we would need to dance the female role and neither of us had any experience of that. Steve just calmly said that if it was a waltz then he could let the man lead and hopefully not stand on his toes. Before I could reply Kay was back and offering her 'man' as partner for Stevie, who rose to the occasion and took the man's hand and was lead onto the floor before being taken in a dance hold, Steve responding by placing his hands in the correct places and following this man round the floor. I was shocked at how easy it looked and how graceful his long dress made him look. All the time dreading that I would have to follow him some time soon. Sure enough the same man returned Stevie to our table and then asked me to join him, I protested saying I had two left feet, he said he could dance with two right feet so it would balance out, Stevie was the one who virtually pulled me from my seat and pushed into the arms of a man. To be fair he was a good dancer and made me feel comfortable as I tried to not crush his feet, almost enjoying the sensation of being held at the waist and gently lead round the floor.
After that nervous start, we all drank more and danced quite a bit more with each other and with various men. It was quite strange to be in the role of a woman and have men asking me for a dance and chatting me up, Pam and Kay both reminding me to flirt with the men if only to get a drink out of them. I became nervous towards the end of the evening as four men had attached themselves to our table and though they freely bought us drinks I was worried where this might lead if one of them stumbles across the true gender of me or Steve.
There had been a surreal moment earlier in the evening when I told Pam I was bursting for the toilet and she rather matter of factly told me I could not use the gents, which I had worked out for myself, and she would accompany me to the ladies where I discovered they are much nicer than the urinals I am used to, nice smells and all cubicles. After sorting myself out after doing my business I found Pam touching up her lipstick and checking herself in the mirror. Being in the ladies was odd enough, but then Pam casually said 'those blokes think we are four singles, and I have a bet on with Kay that you will kiss one before Stevie does.' I guess the shock showed on my face 'don't worry, a kiss does not mean you have to sleep with him.'
'but he is a man.'
'and he thinks Marcela is a hot girl.'
'did you mean this to happen?'
'not quite like this, but it is fun watching you squirm.'
'just one kiss?'
'as many as you like, but Kay has to see you.'
'ok, it cant be that hard.'
As a man I used to look for oppurtunities to kiss girls, but this was different. Jake seemed to be the one attracted to me, and as the dances got slower I found myself in a close embrace with him, our cheeks touched and I thought 'now?' moved my head slightly and his lips met mine, I shut my eyes trying to tell myself this was not weird and kissed Jake as he squeezed my body towards him. In that moment I felt strangely under his power, like I would let him do anything. I felt his tongue on my lips but thankfully the dance ended and that adventure into weirdness ended with it. I looked up to see the other three all embraced by partners, Pam smiling in my direction, and Steve still kissing his man. I just hoped I had done enough for Pam's bet with Kay because Steve had won on time spent on the job.
The party would finish soon after that, but the men seemed to have got the sense of something to come and they became more keen to be close to us, when a chair went missing I ended up sitting on Jake's knee which was awkward, but seeing Steve with a man's arm draped across his shoulder and Steve leaning in towards him made me wonder if he was enjoying it too much. Jake managed a couple more kisses out of me, but I was the most reserved, once outside while waiting for a taxi, I was giving Jake a false phone number but Kay and Steve were enjoying a last snog with their respective men before saying goodnight.
The taxi home seemed to be even more full of dress fabric than going, and the libido was certainly up as my friends on the back seat sat very close together and did not restrain their affections towards one another. I felt rather out of it sat in the front with a bald scruffy driver beside me. Soon Kay and Steve were dropped off and minutes later Pam was paying the driver while I struggled to get the key in the door.
'A coffee I think.'
'Why not.'
I made our drinks then sat down.
'You seemed to be enjoying yourself tonight.'
'Is that a statement or a question?'
'A statement I suppose, just look how you are sat, the way you swept the skirt under as you settled down, you even got saucers out instead of mugs.'
I went on the defensive, 'well the corset makes me sit this way, the skirt needs attention or it will crease and the cups are because I do not want a big mug full before bed.'
'Alright have it your way, but I did notice how many times you checked yourself in the mirrors, the ease with which you let Jake be around you, and the way you were always making sure you looked right with constant checking and preening.'
'And I thought Pete was taking up your attention, anyway what about Steve?' trying to divert the attention from me.
'Oh I think Stevie is going to become a regular, don't you? Rather likes the feminine look a bit more than I expected, the question is will Kay like having a girlfriend or will they go looking for boyfriends?'
'What! Ok he got into the dressing up better than I did but boyfriends?'
'I think there is one last thing you should experience before we say that you are packing away skirts for good.'
She took my manicured hand and lead me to the bedroom, where we helped each other out of our dresses and caressed each other in uninhibited foreplay. We were lying on the bed kissing and petting, but with my cock out of play when I kissed her clit I did wonder what she might do to reciprocate. I soon found out as a finger went up my anus and I felt her tickle something inside which made me gasp. Soon she had lubricated and inserted her dildo inside me and left the motor running while she kissed and stroked me until an orgasm erupted in me like nothing I had had when doing our regular missionary sex. As I came down she took it out, cleaned it and inserted it into her wet hole, cumming nearly as soon as it entered.
'Now then, do you think Marcela will be wanting to come out and play again, because Stevie has already agreed to joining us next weekend.'
So by next weekend will I have
A - decided I want to have nothing more to do with dresses.
B - Agreed to be Marcela just one more time.
C - Discovered Pam and Kay are having an affair, and just wanted to humiliate us.
D - Accept a more feminine lifestyle, dressing and behaving more like a Marcela than a Mark, even preferring being penetrated to any other scenario.
E - Find myself bonding with Stevie even more than before and expressing our friendship in intimate ways that men are not allowed to by society but do not seem to mind women doing.
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A story that came out of a caption by Tiffany
In July Sue came home from work quite excited, she works for a big firm and it had been decided that this year there was going to be a Halloween ball again, I had been the year before and it was a bit of a dead loss, this year however and the reason Sue was excited was that it was going to be fancy dress. I asked what she was going as to get her so excited, turns out it is not what she is going as that was getting her going, it was what I was going as.
You see in her office there is just the two of them, Sue and her boss Robert and I know they get on well as a team inside and outside the office. Turns out they had spent their lunch break thinking up a winning costume for the ball. This is where I come in, the best they came up with was me going as Robert’s wife doing it really well so everyone is taken in and then for the tadah moment I whip off my wig and speak in a deep voice, off course everyone says ‘oh we never guessed you were a man we thought Robert had got married, here have the grand prize money.’ I pointed out that this plan had a few flaws, like I might not do it, or that I might not be at all convincing, and just how was I supposed to be all wifey with a bloke, I had hugged men for sure but in a blokey way, never held hands or kissed one.
Well the discussion came and went all evening, even into bed, she put on her pink silk nightie and let me cuddle her, she knew I liked the feel of silk, so as we got aroused she asked the question ‘you like the feel of this, just imagine having to wear something this nice?’ she was on top and riding my pole, ‘I think you should at least give it a try, we get you dressed in some nice clothes, I do your make up, you borrow a wig and we see how good you look.’ She slid down my shaft making me cum and she knew I would say ‘yes’ because I often did when I came. ‘Perfect I knew you would agree, Robert is coming on Sunday so he can be the judge. Now then dear you have had your fun time to get me there, how about using your tongue you know how much I like that.’
I was manipulated as I often was by her, she often got her way and this weekend I accepted that she would be dressing me as a girl. Luckily though I am not sure if it is luck, we are about the same size so Saturday was spent trying on various items from her wardrobe until she had worked out what looked best on me, a pink satin blouse and a flared black cotton skirt inconveniently coming a few inches above my knee. Then because the skin needs time to recover she has me in the shower and rubbing Veet all over my body, ‘you ever seen a hairy girl?’ was the answer to ‘what are you doing?’ the moisturizer I smoothed in after was lovely and without my protective hairs I could feel fabrics far better making me choose a soft cotton tee and anything but my new jeans.
Sunday was a big day, up and showered then into her silk dressing gown while she did my face. The underwear was all novel but I got it all on, the blouse and skirt were easy, a pair of kitten heel shoes, a blond wig that she had acquired from somewhere, beads and bangles and then ages sat waiting for nail polish to dry on my glue on nails while she got dressed in a very butch shirt and jeans, hair pulled back and no make up. ‘I was the girl today.’ She confidently told me.
I needed some practice in the heels and skirt so she had me preparing the meal for Robert wearing a frilly apron, then there was some cleaning to do before the guest arrived and setting the table. I was well used to balancing my foot on a narrow heel by the time all that was done. Robert was due late afternoon so we had time for a little education, sit like this, stand like this etc. Then about three she playfully tells me I am doing so well in my shoes I should try on something nicer. I found myself wearing higher heels with tiny buckles on I could not undo because the nails got in my way, with a smile she reassured me that with practice I would manage them no trouble. Not sure if she meant the walking or the buckles, but I was stuck in them until she released me.
Robert came with a bottle of wine for the meal and after the greeting kiss for Sue I was introduced as Tiffany or Tiff for short. I was given what I think girls call a visual undressing, I felt thoroughly examined as his eyes scanned me for what seemed like an age. Sue broke the silence by passing me the wine ‘Go and put this in the fridge sweetheart and pour our guest a glass of the champagne I think we should celebrate our winning costume, what do you think Robert?’
‘Oh yes most certainly, if I did not know better I would never have guessed.’
‘Liar, she is not bad and with practice will be perfect.’ She reprimanded Robert ‘Now then Tiff the champagne please.’
We sat about drinking the champagne, but it was me who refilled glasses, got up to check on the meal, served the food, and all Sue would say if I asked for help was ‘You need the practice now.’
Robert left in a taxi after drinking far too much and telling me far too many times he could not wait until Halloween for me to be his wife which got laughs out of me and Sue. But as soon as he was gone she let out an excited squeal ‘this is going to be so much fun, but you are going to have to practice, practice,practice or else people will see through your disguise and that will ruin the effect of the reveal.’
I looked at her ‘If I need all that much practice I am clearly not very good maybe we should call it all off.’
‘Nonsense you have a great body, maybe a bit in at the waist, tits that move and the like, bit of voice training and some getting you to think like a woman and we have it. Robert’s wife!!!’ When she is this excited I know it is best to let her get on with it and it should blow itself out. ‘Right Tiffany, let’s get all cleaned up in here and get us into bed, I think to help you think yourself female you can borrow my pink nightie, we can be girlfriends, wont that be fun?’
I said nothing and dried some plates wondering if this would blow itself out. But she rather hammered a nail into my resistance when she slid a hand around my waist, the satin blouse moving under her fingers made my skin shiver. ‘It will help that you like dressing in girl’s clothes, and before you object, how many times do you ask me to wear these soft fabrics. I will tell you at least seven times a week. Just enjoy the fact that you are being allowed to do what most men are denied.’ She put a hand across my skirt front and smiled ‘Proof but not at all ladylike.’
I have worn a nightie every night since that Sunday initially to please Sue but lately to please myself. Monday thankfully was a working day and all traces of the weekend besides my hairless arms were gone and no one commented on that, maybe because I had little hair before, who knows. The working days were fine but weekends were to change, no more cleaning the house, doing the food shop, going out of the evening then doing something like a walk in the country on Sunday. No my life changed from that weekend, I needed the practice and Sue was the one to make sure I got it. Initially after dressing in a skirt we did the cleaning together, then she would shop, and then because I was not for going out we stopped in. Sundays were taken up with more specific training, voice all the time, walking in ever higher heels, controlling every conceivable skirt style as I did everything else. There was makeup application and beauty treatments to learn as well. And as the July passed into August I found myself doing more of the female stereotype jobs, I did more cooking, I did the ironing, fair enough Sue washed the car and mowed the grass, but I was not brave enough to go out.
Towards the end of August I was pushed from my security of dressing behind doors into the outside world. First it was a busy gay and transvestite bar though she said we looked more like a couple of lesbians, something I was not at all sure my male ego could understand, but I looked good enough for a bloke to buy me a drink and ask if I fancied going to a club later. Sue told me that I had passed several tests all in one with that and from then on our weekends went back to a more usual pattern except I would go food shopping as a woman and get dressed up for the evening which usually involved a short dress and bar hopping.
By September Sue had persuaded me that it would help me with my performance at the party if I thought of myself as female all the time, I did ask if this was a little over the top for a grand, but was told that if something is worth doing it is worth doing properly. So to help me think of myself as female I started wearing women’s knickers and not just the thin cotton ones, no, the ones we bought were all satin and lace, some thongs, some high line but all snug and tight enough to keep my dick under control.
And then another big day happened, not just for my dressing but for quite a few of my workmates as well. We got laid off, we knew the overtime had gone and we had spent too much time cleaning the shop floor and the question was not if but when some were given their cards. Sue in trying to cheer me up told me to look on the bright side, I could spend all day and every day as Tiffany so come the ball I will be a natural and just breeze the prize money.
I did have rather a lot of time on my hands, even after cleaning and cooking an evening meal I did have time to myself. Well maybe I should not have mentioned it but Sue soon had me going round to Robert’s to clean for him and leaving a meal in the oven on a low heat for him. I was now so confident in my Tiffany role I even spent some of my redundancy on new shoes which I tried on in the shop before walking out with them on and then going and buying a new lipstick just because I wanted to see if I could.
Robert had been over for an evening meal few times since he first gave approval of the idea that I be his fake wife and near the end of September he was round, I cooked a lovely meal for the three of us and tried to treat Robert with affection suitable for a husband but it was stiff and forced. So without much discussion Sue decided that I should go and live at Robert’s, so we get comfortable with one another. Robert rather let Sue persuade him into agreeing and soon it was me being awkward for not thinking it a good idea. So a day later with a case of clothes I was shipped off to my new home.
We started off very formally, doing things almost as a copy of 1960s sitcom and soap programmes. He would come home, I would ask if he had had a nice day, he would peck my cheek then sit down to the meal I had all prepared for him. Thankfully we both relaxed into the roles, what did surprise me was that like I had become to like the feel of women’s clothes even the high heels gave me a sense being feminine which I liked, well I began to like Robert kissing me, at first it was scripted but after a week we had gone past pecks on cheeks to lips to hugging while kissing, the argument being that if we kiss in public it needs to look right. Soon we kissed like any normal couple, we greeted with a kiss, said hello with a kiss, said good night with a kiss. And that brings up another unplanned part to this practicing, Robert only had one bed a double. For the first few nights he slept on the settee but in the end he was getting tired and I insisted we share the bed. We never got up to anything but there were times when I woke with him cuddling me and others when it was reversed.
I rather got to like being at Robert’s, he seemed to appreciate me more, thanking me for nice meals, for ironing his shirts, for getting up and making breakfast for him. Sue never said thank you once she just expected it. It might have been that Robert was so nice to me or that we had got tiddly after being out on a Saturday night, but we got in, I stumbled and fell on Robert who tried to catch me but we both ended up on the floor giggling, him on top of me and looking into my eyes. It was then he gave me the first proper kiss, full of passion, tongue, lipstick and lust. And I kissed him back. Ever since Sue had called me her girlfriend she barely wanted me so maybe I was desperate for that sexual buzz and here it was. We really got quite carried away as we rolled about on the carpet, I could feel his erection on my stomach and his leg pressing against my own imprisoned cock. In the excitement of the moment I undid his trousers and let his free, he moved a hand down to mine but I told him to leave it alone it would ruin the illusion of me being a wife, so in answer to his question ‘What now?’ I did to Robert what Sue had done to the male me when I could not go inside her. In the excitement of the moment on that floor, for the first time in my life I slid my lips around the tip of a man’s cock, stroked it with my tongue and swallowed as much as I could. I have to tell you there is pleasure in knowing that what you are doing is giving pleasure to another person, and I enjoyed feeling him getting excited in my mouth. I am not sure the sensation and taste of a mouthful of cum is as good but it was part of it so I was happy to take it.
We lay beside each other on the floor for ages when he climaxed, the electricity was spent and we just lay drained and wondering what the other must be thinking. It was Robert who spoke first, he squeezed my hand and said simply ‘Thank you.’
I said ‘Sorry that was not meant to happen.’
‘But it did and it was nice, no regrets, look on it as part of the training and you just got an A+ for satisfying this husbands needs.’
‘But.’ I tried to say.
‘But nothing Tiffany, you look like a wife, you behave like a wife and that was something I expect a lot of wives do for their men. Maybe one day I will repay the pleasure, but for now thank you, that was lovely.’
We went to bed that night, our touching had new meaning and would not be accidental, and many times it was deliberate and wanted.
With two weeks to the ball we suddenly found that affection was not a pretence we could kiss without reserve and go to bed knowing a cuddle would finish the day nicely. But we also had to sort out our costumes for the ball, clearly we had to have something suitable, just going as a woman would not be enough so he chose to go as prince charming with me being his princess
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As you can see from the picture it was a rather grand costume and Robert decided that as my time as a woman was coming to an end he would treat me to what some consider the height of feminine luxury, to be pampered at a salon. So as we were cuddling one night in bed my hand on his cock he explained how he had been ringing round for a salon that did not mind someone like me going in for a bit of pampering. I thanked him as he came in my hand, the thought of being in one of those purely female shops was exciting to me as I had walked past them many times and wondered what they actually did besides cut hair. Robert arranged for two visits, the first to let them work out what would look best and the second on the Saturday of the ball so I was perfect for the event.
My first visit was like taking a child to a sweet shop, after doing my own makeup and styling my wig as Sue had shown me months before these women asked about the ball, the costume which thankfully I had taken a picture of, and their fascination that I was going to such lengths to win the prize. They flattered me, telling me how convincing I was as I walked confidently in heels far better than many women, that my voice had a lovely husky feminine quality to it that men would find sexy and I had lovely long legs. What they did took hours, they waxed my eyebrows into nice narrow lines, pierced my ears so I could wear nice dangly ear rings, they came up with a pair of false breasts which they glued in place and showed me how to mask the edge with make up, but though I did not realize it they weaved my wig to my own hair so it was secure and I would not need to worry about it moving if the wind caught or I sneezed both events that had happened before and was grateful not to repeat. They washed it and styled it into ringlets like I had done myself but did have a practice at an upstyle to see how it would look at the ball. Robert had asked them to give my nails the works, I doubt he knew what he had asked for because I treated to ten silk wraps being fitted to my finger nails and painted a glossy pink before being sent away and told to be on time on the Saturday as there was much to do. |
Robert was thrilled with the new me spotting everything and telling me how good each change was. He did not spot the adhered bust until we went to bed and noticed I still had a chest inside my nightie which got us nicely into some nice petting and me swallowing another load of his semen.
By Saturday I was loving my feminine lifestyle and went to the salon thrilled that they would turn me into a feminine beauty. Robert was going to collect the outfits from the shop and was nearly as excited as I was. The ladies at the salon made me feel special again as they fixed my hair into a ball on top with curly spindrels all round the edge. My nails were checked and repaired. My face was made up perfectly and eyelash extensions added as a special treat from the women. I felt wonderful as I walked out in my rather plain green dress but I knew Robert would have a fantastic dress to compliment the ladies work.
The dress was lovely to touch the satin skirt felt absolutely luxurious, something we had not realized was that the bodice was very fitted and had a lace back. Robert just looked at is a problem to be solved and soon had me stepping into the dress and pulling the laces tight until he had a satisfactory row of lace holes down my back, that I was feeling unable to breathe, but when I looked in the mirror I could see the result was great, a narrow waist, big skirt, bare shoulders and a nice bust which the ladies had made up well. The finishing touches were chandelier ear pendants, a matching pendant hanging off a velvet choker, and a gift from Robert a squirt of La Femme and finally putting my 4” stilettos onto my stockinged feet. I felt amazing as I waited for Robert to get into his easier outfit.
Once we had got my skirts into the car and made our way to the Hotel function room where the ball was being held the whole event was already in full swing. I easily hung onto Robert’s arm as he made his way through the crowds, chatting with colleagues and friends, buying me with a nice drink when we got to the bar. I knew a few faces but not enough for anyone to rumble my disguise. Sue had turned up in a 1960s biba dress and white pvc boots, she looked great and I told her so as we had a mutual flattery session. I was a little concerned when some blokes were flirting with her but as she pointed out she was currently single, whereas I was currently married. We hugged and laughed before going our separate ways, she to her batman, me to my husband.
We danced, had a few drinks ate from the buffet and received some praise from people I had never seen before. It was as the ball organizers got round to picking the winners that I realized a big mistake, my wig was fixed and there would be no flash of hair as I whipped the fake updo off. I told Robert who told me not to panic I was fantastic and could win without the reveal ‘but that was the big thing, the whole point.’ He told me to relax and wait and see how things go, even if we did not win he had loved having me around.
The judges called together the best and I was thankful to find myself there and smiled as I looked out to see Robert and Sue smiling at me. My life took a big dive just after that, I would have pulled my wig off at this point but could not, Sue was making gestures at me to remove it and she got more angry as she watched me stand there inert. I was given third prize and my interest in the event stopped there, I never heard who won all I could see was Sue fuming at me.
It all over Robert came and gave me a hug and kissed me rather too passionately as Sue strode up to us and pulled me round to face her angry face.
‘What the hell, what happened with the wig.’
‘Sorry it got weaved on, won’t come off.’
‘You pillock, you blew it and the money.’ It was then she noticed I was still holding Robert’s hand and squeezing it tight as she laid into me. ‘And what is this’ pointing at the hands ‘Have I missed something or have you got to liking being Mrs Robert Jones?’
Robert tried calming her down ‘Come on Sue we lost but it is not the end of the world.’
‘Might not be a big deal to you, from where I am looking from it seems you have come of this with a prize, you seem to have got yourself a loving wife.’
I could feel Robert’s hand on my hip pulling me towards him. ‘Well I shan’t lie we have had a good time the past few weeks haven’t we Tiff.’ Then just to rub it in kissed me.
‘Oh go fuck yourselves.’ She spat at us and stomped off.
I later saw her wrapped around a big bloke dressed as Shrek so I could see her, maybe she was trying to upset me, but her words had gone deep and hurt. It was all too easy to turn to Robert for comfort and sympathy, who did nothing to push me away. It was not long after that I asked Robert to take me home, he asked which, I answered ‘Ours’. He smiled and guided me out as he said farewell to a few people on the way out.
We got back and I for one was feeling rather down, it should have been a great night of success, instead I had upset my girlfriend and I was dressed up and thinking ‘How on earth do I look like a bloke after all this?’ Robert poured me a drink and tried to cheer me up with the good points of the night, but it was as he untied the laces at my back and kissed my neck and I felt my skin tingle. ‘How about one last night Tiffany?’
‘You are one randy bloke you know that.’
‘Given what I am looking at are you surprised.’
I ended up in bed with my man and soon my disappointments were forgotten we got ourselves excited. I was stroking my long nails up his extension when a finger found its way inside my thongs arse string. I did squeak a ‘What?’ But was ignored as the finger played around my hole, after the initial resistance I relaxed and enjoyed the sensory delights of being tickled there, but when he massaged some cold gel into the hole I did ask him what he was doing as I had always said it would spoil the illusion if he went inside my knickers.
His reply rather caught me off guard ‘You have been a great wife these past weeks, a more feminine person I yet to meet and you have made a man who has been single for too long look forward to having a woman with him. This might well be our last night together and I would like to make my wife feel like a woman.’ All the time he was tickling that sensitive bit between balls and hole and sliding a finger in and out of the hole.
‘But I am not gay.’
‘Neither am I, to me you are a woman and this man would like to consummate our marriage if my wife will let him.’
I kissed him and played with his cock some more ‘And you think this will fit inside me?’
‘Only one way to find out Tiffany.’ He rolled on top of me and positioned himself until his head was pressing my hole entrance ‘Now relax and let me in.’
I felt him push past the muscles and though it was tight it felt good to have him inside me. It was then the fun really started, he moved slowly in and out getting deeper with every push until he touched something inside me which felt good, I was soon waiting for the next push and pulling him in deeper. I had never climaxed in such a lovely way, as a man it is explode and relax, as Tiffany it built up until waves of pleasure and static radiated from deep inside me making me pant cling onto Robert.
When I finally came down I managed to speak ‘Oh god Robert that was fantastic, where did you learn that?’
‘Off the internet.’
‘Well thank you for looking, if you wanted to make me feel like a bride, you just succeeded. Thank you.’
The Sunday morning was back to reality, it was nearly midday when we got up, I wont say I insisted on a repeat of the night before, but I did want to make sure it was not just a dream. So when Sue knocked on the door as I was making a coffee after just getting up she got an eyeful of the wanton me. Short nightie, boobs still looking realistic inside the cups, hair all over the place, smudged makeup and an unusual gait to my walk as my arse was sore. This picture was not helped by Robert appearing in just a dressing gown and clearly needing a shower.
‘This gets even better, you were supposed to pretend to be married not be married in all but legally signing to it.’
‘And it is so nice to see you Sue, do you want a coffee?’ I tried to ignore her rudeness.
‘No I want an explanation, I was expecting to come round and pick up my boyfriend.’
‘Well that might take some time, you see the wig is rather fixed but you know that already, what you might not know is that these’ I pushed my tits up with my hands ‘Are fixed as well and need a bra. And I am not sure what to do with these’ I showed her my long finger nails. ‘Make a rather odd bloke at the moment won’t I.’
‘My god you did go for it didn’t you, let me guess you got to liking the whole girl thing.’
‘Well you knew that before I moved here, we just let things develop.’
‘I am not sure I want to hear the answer to this but you were rather good at being a couple last night, just how far have you gone?’
I looked at this furious woman and in that instant I thought ‘I don’t want to go back with you, ever.’ So I calmly replied ‘Robert only has one double bed, I thought you knew that.’
She turned to the silent Robert ‘You f****** creep, it was supposed to be a bit of fun not turn him into your real sissy wife.’
Robert tried to calm the raging woman ‘It just happened, we were just getting into the role that’s all.’
‘Well you can stay in that role, you want wife so much you can have him, and as for you I have a good mind to go home and bin all your stuff, seems like your husband here prefers his men in skirts.’ She paused for breath ‘And one last thing dear, use a tampon it stops the stuff dribbling down your leg.’
After the door slammed we both looked at each other neither of us sure who was the most shocked. Robert spoke first as he poured out a coffee ‘No need for you to change back then.’
‘I suppose not, any plans for today now?’
‘Besides spending it with you Tiff, none.’
This could be a story of morals, is it ever wise to lie, should we always be truthful and honest, even if it will cost us.
Or maybe it is just more drivel with bad grammar and spelling mistakes from Lauran.
I just hope you enjoy it, and if you don't, at least I enjoyed writing it. :)
It was only a small lie.
For the first time ever I had been unfaithful, she was young, keen and made herself very avaliable. For both of us I think, it was just the sex. But along with the sex came the buzz of it being illicit, I knew I should not be doing this with Jasmine but it was so much fun I just did not know how to say no.
The lie came one Sunday afternoon when Fay, my wife, was cleaning the car. I was busy indoors watching football when she came in with a pair of Jasmine's kickers, the nice white satin thong pair. This was a bad moment in my life, I had been rumbled and it felt dreadful. I was amazed at how quickly my mind worked in that situation, in the time it took to say 'I can explain' I had remembered our mealtime chats about courses Fay had been running at work on sexist attitudes and acceptance of sexual diversity in the workplace. Now I could have told her they were Jasmine's but that would cause huge irrepairable damage to our relationship, and I do still love her even if I would like more sex, so I decided in a flash to say 'They're mine' to which she replied 'Please explain'.
Now I had to think quickly, I knew about a shop in town which caters for men who like to cross dress, so I came up with this extended lie about how I liked the feel of the satin and wore the knickers for pleasure and comfort. She asked me to go and put them on so she could see what I meant. Now for a boxer man these were snug, I squeezed my bits into the front and thanked god I was no stud and hung like a donkey, then positioned the thin strap up my crack. They felt snug as I say but they were also quite nice to wear after I had got over the initial tightness. Fay was very complimentary about my chioce and asked how it felt to be a man wearing knickers, more lies came out, but now tinged with truth. Then as the conversation went on and I relaxed into the lie I found myself saying I only had the one pair as I usually went to the Transform shop if I wanted to have a full dress up session. Eventually after not finding a decent reason to remove the knickers from under my trousers we went to bed, after Fay had distracted my attention from the soccer highlights by wearing her gossamer thin bady doll outfit. I went to bed in the knickers and we had a smashing session that night is all I will say about it.
The next weekend she went shopping and though I thought the cross dressing thing had been forgotten because it had not been mentioned, I was in for a shock. She called me in and scattered some underwear on the table 'I hope you like them, but it must be very difficult to buy your own so I bought you a few pairs. Yours are the size 12 mine are the 10' On the table was a pile of sexy panties, not her normal plain cotton ones but lace, satin maybe silk. I had to say thank you or give the lie away, and then she told me it was ok with her if I go and try a pair on, I could hardly say 'No I was lying' could I, so I wore a pair of silk and lace french cut panties which were a bit like boxers but much nicer next to my skin.
The lie got deeper when she was asking me if I liked my new underwear, and I had to say yes didn't I, and in truth they were nicer than I expected. So she told me that if they are so nice and it means so much to me that I would have maintianed a secret from her about it, she would be happy for me to wear them all the time. I tried to back pedal saying I was fine with an occasional wear, but she insisted on being understanding and I had no chioce but to wear a red lacy thong the next day.
Seeing the washing drying was a little odd later in the week, no boxers but twice as many panties. I had worn a different pair each day all week. Three things came out of this, I got a illicit sort of buzz from wearing such unconventional underwear, I could never let Jasmine see me wearing them so the affiar was over, and Fay was more randy than I could ever remember.
Over the weeks and months that followed Fay would say she was sorry not have been aware of my needs and wanted to make up for her failings by letting me explore my feminine side.
After the first week in knickers, she encouraged me to wear tights under my trousers, which was unexpectedly nice, then she came home with stockings and suspenders for both of us. Agian another nice experience. This was followed by silk camisoles and I had to admit Fay looked great getting dressed for work in her sillk underwear and stockings, I did not look as good, but I could not stop without telling her I had lied, so I continued.
Soon after I had shaved my legs because the stockings would feel better, and they did. So now I was shaving every week, and not just my legs but all over, including what Fay called a Brazillian. Strange how no body hair makes you feel even more naked.
About this time I felt I ought to back up my lie with a trip to the Transform shop and a bit of reading on the internet about cross dressing. The shop visit was quite an eye opener. They were very impressed that I was wearing my own underwear and was shaved all over. The package I paid for meant I got to wear four outfits, have a complete make over and leave with a series of photgraphs for me to remember my day by. The first outfit was a 'day at the office', pink satin blouse with pussy bow, tight straight black skirt and black courts, the skirt limited my stride and the heels caught me off balance at times. The full make up including pink nails and some neat jewelery made me feel just like one of the girls at work. Then after some photos and a change into 'night out look' A pretty cerise cocktail dress with a flared skirt over net underskirts, long opera gloves and some big jewelery. Then onto another change. 'The wedding' I was squeezed into a corset bodiced dress, and gave me a veil, silk bouquet, the lot, I loved the silk and felt so feminine dressed in it. Then because I had read about it on websites I asked if I could try on a maids outfit, off course I could, proper corset this time, lots of frilly underskirt which did not really cover the stocking tops, black satin dress, very hard to stand in spike heeled shoes, a small apron and mob cap, then I was given a duster and told to clean the guest room while they took photos. All this took hours but I had lots of detail now to back up my lie and strangely I had enjoyed the time more than expected.
I was not sure why Fay brought it up one night after we had had sex but she asked me what sort of dress/outfit I would choose if I could have anything, I thought back to my Transform experience and could honestly say I liked all the clothes I had ever tried on. Then she said she was going to treat me to my own outfit and did I have anything I would prefer. So in my head I discarded the wedding dress, the maid as it might give the wrong ideas, so I told her I quite like the smart but sexy business woman and evening dresses. She kissed me and told me she see what she could do.
Saturday afternoon and she has come home with a smile on her face and bags in her hands. 'Look what I have found for you' she exclaimed with delight 'Let's go and get you out of your shirt and jeans' It took an hour but in that time she had dressed me in a white blouse with more buttons on the cuffs than I have on my shirt and big frilly front which went neatly with the powder blue skirt suit, the skirt being lined and tight enough to show the suspender clips through, she did my face with her make up, then the final nail in my masculinity that afternoon, white stileto sling backs. I was a smart but sexy woman, and for some reason Fay liked it, insisting I stay dressed for the evening.
She asked to wear it on the Sunday as well which rather stopped me going out, so she lent me an apron and 'let' me do some cleaning and cook our meal that evening. I was rewarded with the most fantastic sensation of having the smooth lining in the skirt riding over my arse all day due to wearing a thong as I must never have a VPL apparently, very tired feet from the high heels, and the most fantastic sex when we went to bed.
After that weekend I was 'encouraged' to get rid of all my boxers, well it was months since I had last worn them, and to always wear full underwear includiing a training bra with cups that found something on my chest to fill them. I just hoped no one ever put a hand on my shoulder and felt the strap, it was a nerve wracking but exhilarating experience doing something so off the wall.
Well she found the CD with the pictures from my Transform day not long after and let me know how much she liked them, how good I looked as a woman, which the pictures rather enhanced because of the poses I was asked to stand in. And once again I felt myself sinking deeper into this lie that I was a tranvestite when I was not.
The upshoot of her finding the pictures was that she bought me my own apron and when in my skirt suit was 'allowed' to be a housewife. Then she bought me another outfit, this time a red but loose and virtually see through top, put with black leggings and ankle boots she said I looked dead sexy and insisted I wore a shiny red bra that was filled so much it stood out against the thin fabric and clearly visible, to me anyway.
That night during our sexual adventures with her on top and in charge, she paused as I was getting close and suggested we go out to the gay bars in town, I had to ask why, her reply 'Well where else could two women go for a night out' then she rode up and down some more and I knew I had agreed to going out with her as a woman. And all because I could not tell the truth.
The next week I was worried sick, the buzz from wearing female underwear was fading as I had no chioce by this time, because Fay wanted me to get in touch more fully with my feminine side. The fun wearing thin if you will excuse the pun, all I could think about were those sad images of big builder types in dreadful outfits and hairy arms drinking pints you see on some TV programmes. She could tell I was nervous and suggested we go on the Friday evening with me as me, then when we have had a good look round we shall know what to expect the following night.
What I was not ready for was a full day of preparations, soaking in hot scented baths, shaving all over, doing as much girlie stuff as Fay could find, then when it came time to get ready I am presented with a pair of very realistic silicon breasts to put into a bra, the wieght surprised me after using rolled up tights, and then a very tight thong to keep my male bump squashed into my grion and I was ready for the leggings and loose top. Fay helped me with make up though she had been teaching me how to do it myself, this time she wanted to be sure I looked my best. A few new things appeared that afternoon, plucking eyebrows being one and at first 'just to neaten them up' but that quickly became 'keeping them looking good' which meant thinner. My hair which was mousy brown and long for a bloke had been styled before, but this time after she styled it she trimmed a few ends to give it shape she said, stop it from tucking behind my ears I found out when I went to work on Monday, meaning I either had to have a fringe flopping across my face or use gel to hold it in place, both a bit too feminine for a man at work.
The evening itself was not that bad after I had got over the initial trauma of leaving the house while thinking every curtian would be twitching to see how I was dressed. Fay just told me I looked like a woman going out with another woman. I forgot to say Fay was wearing a stunning red tube dress, red heels and a big smile. We parked and walked to our first chioce, a bar for a warm up drink, then onto a resturaunt before going round a few more bars to see what a Saturday night has to offer. I was pleased to see and chat with other wierd people like myself who I found out actually prefered to wear a dress to trousers, and was invited to their Wednesday night club. Fay said I should go, and there were two good looking girls, that is good looking for men dressed as women who suggested we go onto a club with a dancefloor and is the place trannies migrate too. They were right, lots of them, some not so good looking, but all seemed to be having a good time. I think I was the only one there with a real woman, though there were a few couples but I reckoned they were both men under the clothing, and quite a few men out to pull themselves one of the single trannies. It was all rather novel to me and Fay I think as we held hands and danced a bit before leaving for home. One last 'delight' Fay had to help open me up to my femme side was to give me short pink silk nightie with built in cups so i could slip the inserts in to keep my female body shape, she was really keen to be on top that night and played with my new chest like I would have done to her in the past.
From that day on Fay made sure I had every oppurtunity to be the woman I 'needed' to be so I could be fulfilled. She bought me more clothes and ever higher shoes until I was walking in 4" heels and only a toe strap to keep them on. Any time away from work was pretty much spent by 'indulging' my passion. We were giving each other manicures, brushing hair till it shone, reading magazines together. Gone were my sport magazines, football never came on the TV anymore, Gok Wan and how to look good naked, or model wanabee programmes as we discussed the styles. I was so involved that when I was asked to have my ears pierced I did not even recognise it as something I should not do, rather it would mean I could wear those nice chandelier ear rings I had seen.
I did go to the tranny club and made a few friends there, Mike or Michelle as he preferred was good fun to be around, he looked real good when he dressed and with his encouragement got me be more adventurous, going out dressed without Fay, even going out in daytime for a wander round the city shops and coffee shops. There was one main difference between me and Michelle though, I was striaght, Mike was gay, which was fine he did not fancy me as I was a 'woman', no he wanted a man who wanted a chick with a dick, and because when dressed as Michelle she looked hot, there was no shortage of potential admirers as I discovered they were called.
Then one weekend Fay wanted to go and see an old friend on her own, I said fine and thought it would be a chance to slip back into manly ways for a change, but she told Michelle who told me were going to have fun, I told Fay she was the only one for me as she left on that Saturday morning while I was still in my nightie, wrap and heeled slippers, she smiled back and told me to enjoy myself. Fay was hardly gone when Mike turned up in a very male style, and as I had not had chance to get out of my nightwear he got to see me in the nightie and wrap, maybe he had expected a male version of me, but was clearly pleased to see I had spent the night in such female attire. He called me darling and gave me a peck on the check. I was hoping to just slob around for the day, instead made him a coffee and when I said I was going to have a shower and change, he said 'wear the long plum dress, it looks nice on you' so much for being a bloke. Then as I walked past him he patted my bum, he was being so masculine I was wishing Michelle had come instead.
When I was getting dressed he suggested I try adhesive with my breasts, then I feel them better. Then he showed me how he hid his boy bits and encouraged me to do it. I was soon stood infront of a gay man naked and displaying nothing that looked manly. My status as a woman while he was a man was further enforced as he stroked my bare skin and told me I looked beautiful. By this time I could dress and do my make up as quickly as any woman and was soon downstairs in the plum dress. 'Right then darling, I am taking you out for a treat today, get your bag and don't even think of saying no, I think you spend to much time with Fay beinga pretend lesbian, today I hope to let you see what it is like to be with a man' I should have guessed at that point where this would lead, but I did not.
He took me out to lunch, walked around some shops, then went for coffee and cake at a local beauty spot before stopping at his house where he offered me the chioce of his/Michelle's wardrobe. I tried on several dresses, he had plenty of party outfits as well as plainer daytime stuff for me to try on. His favourite on me was a lace top which left nothing to the imagination and a red leather mini. He was clearly well planned and said it was great club gear, so why don't we go to a club. Hardly able to stop his enthusiasm I ended up on the arm of a bloke being walked through town looking liking like a tart. However it was a very different experience to that of being out with Fay or Michelle, with both of them I felt like a woman out with another woman, equal in some ways, though they have different agendas for their nights out, and I was happy to just be along and not cause trouble for myself. Being with Mike was very different, he was flirting with me, flattering me in a different way, before it had been to make me feel confident I looked OK, now it was flattery to make me feel good. And I did feel good, I had never gone out of my way to attract admirers but in that nights outfit, whenever Mike left me I could almost feel the eyes and sometimes hands on me, and the chat ups were frequent and in my mood that night, welcome.
We danced, we smooched, we walked arm in arm, he held me close, he kissed me, I melted in his arms, we cuddled. Then when we got back to my house I invited him in for a coffee and he taught me the pleasures of being a female in a partnership. He controlled me, made me feel wanted, aroused me, so when he suggested bed I was in the right frame mind, half drunk, half deluded That I wanted him to make me feel like a complete woman, to be his woman and give him pleasure. He undressed me and I undressed him, I had never seen another man's erect penis before, and definitely never one so close as when I slipped his trousers off. We kissed, we cuddled, we petted, we applied luricant, we used protection, we lay as lovers do, me on my back legs in the air, him on top pumping into me. Like I say I wanted to be there because I was drunk and he had seduced me into it, but as he pumped I got past the pain and enjoyed the sensations until I had an orgasm that came from deep inside coming in waves, quite unlike the sudden explosion I got as a man. I lay in my marriage bed not caring that I had made love to someone other than Fay in it.
That was until the morning, I woke with a sore arse and no Mike, then I heard vioces, could be the TV but it was late and did not sound right. Curious I got up, no nightie just bra, knickers and stockings on from the night before. I walked downstairs fastening the tie around my wrap, I could see Mike in my male dressing gown sat at the kitchen table talking to someone just out af sight, then I heard her speak, Fay was back. Wishing a hole would appear to swallow me, this was not a good situation, Mike turned to me and smiled and not just a friendly smile, one full of longing and lust. Then Fay spoke 'A good night I take it?' this was not a polite question, 'well it proves one thing, you cant be trusted' I tried to say 'what', but she just went over the evidence, stockings showing beneath my wrap instead of a nightie, walking awkwardly and unwilling to sit, Mike in my dressing gown looking like the cat that got the milk and wanting some more. Mike was not helping with anything that sounded like a denial, and I just felt so bad, added to which I had got used to being subservient to both of these people and dressed in just my underwear it felt wrong to speak up and challenge them.
Then came the final blow 'This actually makes what I have to say so much easier. When you said those panties were yours all those months ago, I knew they weren't but it was fun to see you squirm as you got deeper and deeper into being a girl, and it rekindled something I had felt at college with Becka, you were a dull predictable lover as a bloke but as a woman I wondered if it would be different maybe better. It was not bad but Becka was better.'
I was stood open mouthed not knowing what to make of this information, she had known from the start, the lie was in vien.
She continued 'And it seems last night must have been something of a moment for both of us, you have found out what it is like to lie on your back and let a man use you, whereas I refound my love for Becka, you see we can both be unfaithful, all we need to work out is who is stopping here, because sure as anything I do not want a fake woman when I can have a real one' then she turned to Mike 'do you want it'
'Don't drag me into this, I just thought it would be fun to be a man for a change, no I want a man in my life, girlfriends I reckon are for gossiping with and sharing clothes, I only thought it would make a nice change for both of us. But I did think you were broad minded enough to let her enjoy being screwed by a man'
There is nothing like having your world fall apart in a few minutes to crush your self worth. I turned and fled to the bedroom in tears, considering what the future held. I could stop dressing completely, it was all a lie anyway, but then the doubts appeared. Mike had given me such a great time the night before. Fay had told me I was useless as a lover. Jasmine had not seemed bothered when I broke it off with her. Maybe I should follow Mikes lead and be a girl to attract men, but it is all based on a lie that I am a transvestite when I am not.
What a terrible position to be in and all because I could not be honest in the first place.
In his position what would you do?
This story was written with the help of T Manners
This might not be how hypnotism works or people react to it, but for the sake of this story please play along and enjoy the fantasy that is Justin’s fate.
Clare was really keen on the show she had seen advertised on her way home when I met her in the pub later that evening after work, we had been seeing each other for a few months and I was hoping that pretty soon she would move in with me, she was not the super model I had always dreamt of bedding but she was fun to be with and made nice food, which is bound to be a good combination. I made it clear I suspected that hypnotists were fakes and just put on a good show with stooges being able actors who played the role of a trance well. I crumbled and agreed to going.
Friday evening I am stood in the rain outside the theatre waiting for Clare to show up, she is as normal not dressed up, jeans, sweat top and trainers, I have to admit I made more effort with my appearance than her, neat canvas shoes, skinny jeans, soft white cotton shirt. We kissed and she apologised as we stumbled in through the door. I could not believe she had got us seats at the front below the stage, the doomed row at any audience participation show, comedians had been merciless in the past from my experience and I would chose the circle from choice, but this was Clare's choice and we were in the target area. Though I did tell myself they used stooges, but being this close was still a worry.
The show started 'The amazing Bruce' (what a crap name) came on, he had a younger man helping him as the show progressed. A bit of a chat to loosen us up, then an invite to the audience for anyone who wants to stop smoking, I had heard this worked but how would we know if he was successful today? Then the amusing bits of 'innocent' people barking like dogs and a big guy trying to do a few ballet moves. My life changed as the big guy came off the stage completely unaware of why people were laughing.
'Is there anyone here who thinks this is all staged?' Bruce asked to everyone in general. Clare grabbed my wrist and held it up, 'which of you or both of you?'
'Him' Clare shouted.
'We have a doubter, come up here young man, your name please?'
I turned to Clare and mouthed 'you are dead' she just smiled back and waved.
'Justin.' I answered.
'So Justin you think all this is fake.' I went on to say I thought so and that I had only come because my girlfriend had dragged me there.
'So I could not get you to do things you would not want to do?'
'No.' I was emphatic.
'So if I could get you to do something you would hate doing?' he left the sentence hanging. 'What would you find most embarrassing? Maybe we should ask your girlfriend.' he moved to the edge of the stage 'Excuse me dear, I guess your boyfriend is straight?'
'Yes' Clare replied.
'So if I asked him to kiss Joseph here, he would not do it?'
Clare just laughed.
Bruce came back to me 'now then Justin, if I am any good at this then before the end of the show you will voluntarily want to give Joseph here your best kiss, one you would give your lover.' I was starting to get nervous and told no way was I going to kiss any lad not even Joseph 'oh I do like a challenge.' he announced to the theatre. 'Please take seat Justin, make yourself comfortable, now relax.' And that was the last thing I can honestly say I did as Justin. I was aware of what he was saying and doing, I saw other people come on the stage, but all the time I was watching Joseph helping people up the steps as he had done with me. Then it happened, Bruce's attention returned to me, he first asked the audience for a girly name for me and out of all the eager suggestions he picked out Tiffany. 'Now Tiffany, we have all enjoyed watching your eyes following Joseph about the stage, I think there is something you would like to do.' I felt a really strong urge to kiss Joseph, he looked so handsome and though I was not dressed very well, wishing I had made more effort to look pretty before I came. I got up and walked to the man of my focus, wiggling my hips as I walked. The kiss was as passionate as I could make it, well there were a few hundred watching us which can put some off. Joseph seemed to be enjoying it as well. The audience applauded though I was not sure why as Joseph took my hand and lead me backstage.
I felt like a teenager in love for the first time, I could feel his soft hand in mine but all the time thinking to myself 'what must he be thinking of me dressed up like this, anyone could take me for a lad.' The cheering and clapping ended eventually and Bruce came backstage to the dressing rooms. I said something banal like 'oh hi' as he walked past and motioned for us to follow, I just kept hold of Joseph's hand not wanting to be parted from my new boyfriend.
'So Tiffany, what do you think of my show?'
'Really good, I am amazed how you can get all those people to do those things, it is incredible how they fall for it.'
'And Joseph, what do you think of Tiffany?'
'Certainly can kiss, but can't say anything more yet.'
'Was one of the most susceptible this tour, I am constantly surprising myself at how people react.'
I decided to be bold as I might never be in this situation again, 'excuse me but I know I have only just met you and all that but I was hoping that I could see you again.' I was still holding Joseph's hand and looking directly at him.
'Well I don't know, we are going to another town tomorrow for a few days then we are taking a holiday' Joseph replied. 'Besides, what about your girlfriend?'
'Oh Clare, she is just a girl friend.'
I could see the two men looking at one another.
It was Joseph who spoke, 'Tiffany, how about you come back to my hotel and we can have a chat about it, see where we are in the morning?'
'This could be dangerous, he really seems to think he is your girlfriend.'
'I will be careful I know about consent, and you have just heard her ask me to take her out.'
There was clearly tension between them but when Joseph got up and asked me to follow I did. It was only a short walk to his hotel, hardly a word was said until we had closed the door 'Tiffany you do know that you are a special sort of girl?'
'Oh yes I have unusual bits down here for a girl' I gestured to my crotch and giggled
'and that does not bother you?'
'It has not in the past, anyway why are you asking me all these questions? I would have thought you had brought me here to do something more than talk.' I then took his arm and pulled us together and locked my lips onto his, it felt like perfection, he knew just how to make me feel like his girl.
I woke in the morning having had a the best ever sex during the night, I just loved feeling him inside me, not only using me for his own pleasure but making sure I did not go without. I could not remember an orgasm like it, no one had made me desire the climax so much. I showered and apologised for looking so bad explaining that I would have worn something more appropriate if I had know I was going to be ending up in such a situation. He stroked my cheek and asked me if I could take a few days off work and go with him to the next town, my face light up, I could feel it, off course I could, but I had nothing to wear. With a reassuring cuddle he told me that would be ok we could buy some nice new ones later on that day. I just could not believe my luck that he actually wanted me to go with him.
Over breakfast, Bruce and Joseph discussed how they planned to get to the next venue, all that sorted Joseph then dropped his bombshell 'can Tiffany come with us?'
'Good grief son what are you thinking?'
'I have tried the trigger words and none work, he still thinks she is my girlfriend.' I smiled at him possibly a little too sweetly.
'But what about her or do I mean his past, family, you saw the girlfriend, there will be a job somewhere.'
I chipped in here 'Don't mind Clare she is only a friend, my family are just a few distant relatives that I have not seen in years, and would you work in a call centre trying to sell loans. Please can I come I will help where I can, anything. Please.'
'You sure about this Joe?'
'Pretty sure.'
'And how does a gay man handle having a girlfriend who I have to admit does look rather masculine this morning.' Pressed Bruce
'It just works, ok.'
'And is good in bed.' Bruce stated. I blushed. Joseph nodded. 'Ok I will try the triggers in a bit, maybe she will stop loving you then.'
Joseph left me in the bedroom to pack his case while he chatted with Bruce, a short while later Bruce came in and asked me some stupid questions and said some random words that made no sense at all, but I have read these performers can act strangely at times so let it pass for being eccentric. Joseph drove while Bruce sat in the front and dozed. I sat in the back so pleased to be getting away from my dull boring life, maybe Monday I would call work and tell them I had left.
It did not seem that long since we set off but soon Joseph was parking the car outside a hotel. Bruce told him he would be fine and would take a walk before meeting again at the theatre early afternoon. Joseph took my hand and led me towards the hotel. We booked in and then asked if there was a salon nearby. One just round the corner, used to theatre types as well the reception proudly informed us, as well as asking if she could get a couple of tickets. He then leant over the desk and whispered something, the girl looked at me, then at Joseph, 'I will ask, but I am sure they will be fine with that, should I tell them who you are.' 'Maybe not.' Was his reply.
After sitting in the lobby reading Hello for ages, Joseph came over 'right all sorted, you come with me, I will show you where the salon is and I shall go and buy you some clean clothes, make you all pretty like you tell me you ought to be.' I smiled up at him. 'Come on then.' It was just round the corner and a quiet shop entrance opened to a luxurious den where women make themselves better or at least that what Joseph told me they would do to me.
I was left in the hands of two women, Kay and June, older women who did not seem fazed by the sight of a girl dressed as a boy and being asked to do whatever it takes to make her pretty. I remember them asking 'Anything?' and Joseph replying 'Yes anything you think will help.' Joseph left to go shopping for some clothes leaving me alone.
'Ok my dear maybe we should start with waxing.'
I was taken to a back room, asked to strip and then the pain started, my whole body stung by the end but the pleasure of being massaged with oils made up for it, nearly.
'Right let's get the painful stuff out of the way first. Ears. One, two, big, small, long, any preference.'
'Big hoops please.'
I soon had hoops hanging from my lobes.
I was then taken to the salon in a gown and asked to just let them get on with what they had to do, it would take a few hours and they would explain as they went along. My hair was washed, and then while Kay played with my hair, June took my hands and started to play with my nails. I found this all rather relaxing after the wax and piercing, allowing myself to just dream of how I might end up and would Joseph approve. The next time I looked at my nails I was amazed to see ten long bright pink nails at the ends of my fingers. I think I said something like 'wow'
Kay asked 'you like them?'
'Oh beautiful' I replied.
'Wait till you see your hair' she reassured me.
The hair took longer but when they had finished adding products then rinsing them off and drying the results I had what they called a long bob in much darker colour than my natural tone, but it looked great.
'Ok Tiffany, still a few things to do, we shall do make up next and you need to listen very carefully to what we tell you because I think you will need to be able to do this yourself.'
'Ok I think I know quite a bit, but we can never stop learning' I giggled 'so they say.'
I noticed the two women give each other odd looks like is was mad. Kay brought over a trolley and proceeded to tell me what everything was and show me how to apply it. I soon had thin outlines round my eyes with grey shades of shadow above them, my face was looking a healthy tan with nice cheekbones, but it was my lovely full moist pink lips that looked the best. I moved my mouth and circled the tip of my tongue round the pink hole. 'You are wonderful you know.' I complimented them.
Just then Joseph came back with bags in his hands, 'wow Tiffany you look brilliant, do you like it?'
'I was just telling them that they are miracle workers, I told you I could be pretty but this is wonderful.'
Kay butted in 'right then my dear, now we have some clothes, let's go in the back again and get you dressed.'
The gown off I was given some tight pants to put on first and squash my unfeminine bit flat, I could hear June asking Joseph 'are sure about this size?' and him saying yes. June then coming in saying 'well if this is what they want, I would not thank you though, double D they have here Kay.'
'Oh my god, but she is not that big herself, never mind the customer is always right, just hold still dear while we fix these to your chest.' They weighed quite a bit and I was happy to feel the bra support them, I just looked at them and thought 'what a lovely pair, he will love them.'
Soon I was learning how to fasten buttons with long nails and pull up tights without laddering them.
'Take a look at this Kay' June said as she held up my skirt 'only the young can get away with such stuff, hardly cover anything.'
Kay was opening the last box 'and whose idea was this? Have you ever worn anything like them before?'
'Oh I said I liked those really tall heels, can't be that hard to walk in them, its only one foot in front of the other.'
'Well maybe dear.' said a doubtful Kay.
I stood up and brushed what there was of my skirt down, straightened the bow and fluffed out the sleeves. I was stood on my toes and just felt that if I kept myself very straight and upright, leading with my toes I would be all right.
'Well my dear not so bad after all.' I stuck my hands out at right angles from my wrists and minced out to show Joseph the real me.
He did not say anything for a minute 'Oh Tiffany you are fantastic, I can honestly say I have never known anyone like you.'
'Can I kiss him?' I asked.
'Yes the lipstick is pretty tough, just touch it up if it starts to fade.' June advised me.
We left with a bag of cosmetics and hair products in a carrier bag, I had a small handbag that hung from a chain off my shoulder, the bag riding at the side of my hip, one hand steadying it while the other manicured hand held onto my boyfriend.
'How far do you think you can walk in them?'
'For you, anywhere.'
'Well let’s go for the hotel and get the car.'
It was not too bad but my legs were aching when I sat down in the car. 'Right then dear. Let us go and show you to my father.'
'I do hope he likes me, he was not too keen on me coming was he?'
'Maybe not but he is a leg man, and you have lovely legs.'
'I do don't I. Thank you ever so much, I will do whatever you ask for doing this for me, I must repay you somehow.'
'Just being my pretty girlfriend will be more than enough.'
His father was not quite as impressed as I hoped he would be.
'My god Joe, what have you done, or has she done. I mean this is unbelievable she looks,,,,,well she looks like a bim'
Joseph cut him off 'A girl dad, Tiffany is a girl, remember, you told her she was.'
'So I did, but a bit over the top isn't it.'
'Not if she was on the stage, or going out with me after a show.'
'But it is only five in the afternoon.' Argued Bruce.
Joseph changed the subject. 'Best go and get something to eat then hadn't we.'
Joseph took my hand and lead me into a small Italian restaurant, I could feel the waiters eyes on me as I walked in. I could also sense Joseph’s proud smile as he walked beside me. I ate a small salad as I knew I should, it never looks good to see a woman with a huge plate of food. The two men discussed some technical things about the theatre and the show which I had no clue about so just smiled and tried to look interested, but was more interested in the bum on a nice looking waiter. The talk came round to me and they were talking about me, not to me when they considered if I might be able to help out on stage. I did say I would do anything and being on stage mincing about looking pretty would be something I could do well, I thought so anyway. Joseph seemed keen on the idea but Bruce was not so sure 'what if I reverted in a show?' seemed to bother him though I had no idea what he was on about. Joseph said he would train me while Bruce was on holiday, turn me into 'eye candy' something to distract the men. I knew what that meant, I would get to look glamorous.
For the show I sat in the wings watching as Bruce did his thing and Joseph organised the show, they were very good at it, impressive at times, making people laugh and applaud at others, they were so clever. Joseph had another treat for me later that evening, when we got back to the hotel he gave me a bag and told me to go into the en suite, I needed to clean my face and do my beauty regime anyway so trotted off. The bag had bright pink nightie, soft and cool satin. I put it on and as I went back into the bedroom leant by the door frame with a leg lifted up in what I hoped was a sexy pose 'so do you like it?'
'Oh Tiffany you are perfect, I think you are beautiful.' He says all the right things doesn't he. I took him to bed and made sure his manly urges were satisfied before I went to sleep.
In the morning I found out that Joseph had bought me some other clothes for wearing in the daytime, silver leggings and a loose grey top. His only instruction to me was that I need to hide my extra bit and make a flat front. I found it easy with the tight panties and pushing it backwards. I only had the one pair of shoes which I did not mind as they looked great and I thought made my legs fantastic. After quite a while doing my make up, June and Kay had made it look so easy the day before, I went down for breakfast, just fruit and cereal, well I did need to watch my figure now I might be going on the stage.
The day was quite dull, I walked round the town centre, had a coffee with Joseph at lunch time, read a magazine in the hotel room in the afternoon. Then sat in the wings again watching the show. This was followed by the highlight of the day, getting Joseph aroused and randy, and then letting him fill me with his wonderful manhood. I could not believe I was so lucky to have this gorgeous man as my boyfriend, he looked good, treated me well and was a great lover. I was just going to have to do whatever to keep him, wasn't I?
The few days at that theatre passed quite quickly, Joseph gave me some money to go shopping with, I could have spent all my time reading fashion and celeb magazines though, the pictures were incredible and had me imagining what I might look like in their shoes, literally. I think I only made one mistake then and that was easily mended, I bought some flat sandals and Joseph did not say anything but I could tell he did not like them so I took them back and swapped them for stilettos which got his approval.
When the show was finished on the last night we were all packed for going home, it was a fair drive and after dropping Bruce I finally got to see Joseph's home, a nice city flat, with nice views and generous room sizes. But the black satin sheets on the bed meant only one thing even though it was late I wanted Joseph to be pleased with me so I made sure he was happy in his satin nest.
Bruce was away for at least two weeks and it was four weeks before the next show, so Joseph said I would have time to get myself ready for being a stage assistant. He explained my job would be to help members of the audience on stage, hand any props out but mostly to look gorgeous. I promised to do my best, and then he added it would be possible to make me even more gorgeous, like a fool I asked how? He cuddled me and cupped my bra 'by making these real', I giggled and asked 'can you do that?' Off course he could, he was Joseph, he organised things.
Two days later I had signed the papers and in a nice clinic that Joseph had found I was turned into the girl you see today. They made my chest all me which meant I could wear those low cut tops which men seem to like so much, they also put fillers in my bum giving me quite an arse. My face got some alterations as well, my lips were a little plumper, my cheekbones higher or seemed to be and my nose a little smaller. But what really surprised me when all the aches and pains had subsided was that they had operated on my neck, something about my adams apple, but also when I spoke I had really high pitch voice which at first sounded odd but I got used to it and kept it quiet as much as possible.
The next time I saw Bruce most of the swelling and bruising had gone, Joseph had had me doing catwalk walking in the highest heels we could find until I was doing it without thinking. I was not sure if Bruce was pleased with the things me and Joseph had done to my body to make me look prettier, but he was definitely surprised. I did hear Bruce ask in a rather concerned tone 'and what if a trigger happens, then what?'
Joseph squared up to him and gave it him straight 'Tiffany loves being a woman, she constantly wants to look pretty, she never wears flat shoes or goes out without make up, and between you and me she can't get enough of me in bed, besides her dick you would never know she was once a bloke. And even if a trigger did revert her I am sure she likes being a woman so much she would volunteer to stay as one.'
'And you are sure.'
'Confident.'
I came in at the end of the conversation and asked what a trigger is, 'nothing to worry your pretty little head' I was told.
'Would either of you two men like a drink, I was just going to put the kettle on.' I stood there with a hand on my hip as pushed my arse sideways, the tight short skirt showing my new shaped bum off perfectly.
'Ok she can be a stage assistant.' Bruce said with a sound of defeat.
'Oh Bruce thank you, I shan't let you down, I will do a great job you just wait and see.' I excitedly hugged him and gave him a kiss.
'Enough of that Tiffany, a tea would be nice.' Bruce managed to say eventually.
We bought a stage costume the day after, long black with a split up the leg and a neck that just about held my bust inside. I went to a salon to find out how I could put my hair up in a bun type style, showing off my neck and long ear rings. I gave Joseph a preview at his house, he made a few suggestions such as making the split open when I stood still and make my arse wiggle more so the skirt sways more. I felt as if I had made it as a woman in that dress, and as Joseph helped me out of it and made love to me, I felt like a woman, being pleasured and giving pleasure to this wonderful man.
A week later I was on the stage to help the innocent victims on stage to be humiliated, teased and laughed at. It was all done in good humour and no one ever left not having had a good time.
Six months later we were back in my home town and in the theatre where I met Joseph, I was in Joseph's favourite red lycra tube dress (I think he likes it because I wear it without a bra and once it was not high enough and he got an eyeful of my nipple as it all malfunctioned) walking to the theatre I spotted my old friend Clare. I can't understand why we had been friends, what a frump, she was in a baggy knitted jumper and blue jeans, her hair short and a big satchel over her shoulder. I know she was not the most attractive woman but she hardly made an effort to tell the world she was a woman. Walking up to her I felt just superior, like she would never look as good as me or get such a great guy like Joseph. Just imagine if I wore those hippy clothes I would look dreadful. As we got closer I could tell she did not recognise me, so I moved into her path 'oh hi Clare'
'Sorry do I know you.'
'Tiffany. We used to be friends about a year ago.'
'I doubt it, my friends are not bimbos.' but she was looking carefully at me, then her jaw dropped and she mouthed 'Justin'
'No Tiffany.' I corrected 'Anyway would love to chat but got to dash, need to get ready for the show, do come along if you can, it is very good, Bruce is excellent.' I walked away but was sure Clare's eyes followed me till I turned the corner.
I was telling Joseph about meeting Clare later while I was cleaning my make up off. He was surprised I had memories of my old friends, I asked him why, so he explained how the hypnosis can somehow delete memories and he was not sure how deep my hypnosis had been. It was as I cupped his balls in my fingers, the nails tickling his arse hole that I asked him if I had been hypnotized.
'Yes quite a while ago.'
'And did it work?'
'Very well.'
'In what way?'
'It helped you overcome your fear of looking pretty.'
'I suppose it did. But I always thought that if the hypnotized heard a word it would bring them back to who they were.'
'Well it is maybe too much for you to understand but sometimes there is no need for a trigger, like with giving up smoking, and occasionally the trigger does not work.'
'And that was what you and Bruce were talking about a few weeks ago.'
'Sorry?'
'About me and triggers.'
'Well yes it was, but we think you are one those rare people for who the trigger does not work, which is not a problem as you like being pretty.'
'That is true I do like looking my best for you, but I think you are wrong about triggers.'
'Oh why?'
'Because I remember when I heard mine.'
His face went pale and his dick wilted in my hand 'So you are not hypnotized.'
'No Joseph I have been me for ages.'
'So please tell me when did you become conscious?'
'The moment you climaxed me that first time, I was under you and had a vague feeling of enjoyment and longing for you, but that orgasm was so great it woke me up.'
'Oh I am so sorry.' he was looking really worried.
'Don't be sorry, you opened a whole new side to me, you made me feel wanted, and it should be me who should apologise, I have been lying to you ever since, but I felt the only way to keep you and have you make love to me again was for me to be Tiffany and be the person you wanted me to be.'
'So you are here willingly? Not because we tricked you?'
'Yes, I am here because I love being with you.'
'And the bimbo look?'
'You like it, so I like it, besides have you seen how men turn and stare, I never got that attention before.'
'Oh Tiffany I don't know what to say, I have been worried someday you might wake up and hate me.'
'Say nothing until you have made me scream and then you can tell me that you love me.
Another implausable story of how a man ends up living the life of a woman.
Based on an idea given me by Angela Myers. Thank you.
I was in a bar where cross dressers meet and as always there will be someone new to chat too, might be a new one on the scene or a visitor. Whatever their origins if they look nice and are friendly then I am open for a chat and possible new friendships.
Angela was chatting away about her background and I was taken by her unusually late in life conversion, late 20s at a guess, not the usual 'I was doing this as a kid' story. In fact she had only been dressing for ten months, but what a ten months.
She had been a regular bloke, working in a dead end job at a warehouse doing paper shuffling work, 'never did like to get my hands dirty' was his career choice it seemed. Was also a bit of a rocker with the long hair that is common among such fans. But that life ended when she went to get her hair trimmed, she might have been a rocker but she was a clean and neat one. The regular hairdresser was shut so she choose another of the unisex salons that apparently have no problem catering for men who want more than short back and sides. That was her first life changing choice.
Her next choice was to voice her opinions about a gay pride carnival that was being run in the city later that month. She could have said how good it would be, or even said nothing, but she made a few homophobic comments, questioning why a man would want to be the 'woman' in a relationship, whether that be dressed as a man or even as a woman. His mistake was that she failed to realise that the man washing and trimming her hair was gay, along with the majority of the other staff.
That visit turned out fine, she was happy with the care and attention they took and was very pleased with the finished cut, even if it was just a pony tail. The impact of those remarks came home to roost on her next visit, unknown to her at the time, once the appointment was made the salon owner and person who had looked after her the last time was having a bad time, his partner had left him, the gopher was becoming ever more unreliable, and the tax bill needed paying along with several suppliers. Angela's previous comments just added fuel to his smouldering fire. The intervening three days between booking and appearing gave Pete enough time to plan a stunt, which he admitted on reflection was totally out of proportion to the insults made, none the less it happened.
Angela turned up for the appointment on time, but was told they were running late and was given a complimentary coffee which tasted kind off odd, but the soon to be restyled Angela thought it was just the brand they used and drank it down. That was pretty much the last thing she remembered doing as a man. Pete called Andy to the chair, but that was about it. Andy's next recollection was as a woman, well at least looking like a woman. She was in a strange room wearing a short satin nightie and wrap, lying on a couch while in the corner a tv was playing. It took a good five minutes before she really started to watch what was on the screen, what with being in some one else's home and wearing women's nightwear and from what she could make out several other female type changes,such as long finger nails, unexpected breasts, a hair style she knew was different as it was not a pony tail, and also her arse was sore. Then just as she was thinking of getting out and sorting out whoever had done this to her, she recognised the salon on the tv, with Andy walking towards Pete and the washing station. She then went on to tell me what she saw as she sat transfixed by the recording.
Pete led 'Andy' into a back room and started washing the hair, then to Angela's surprise this man she knew to be herself had a conversation as they discussed what Pete planned to do with her hair. Still looking like Andy, she quite willingly agreed to having the hair bleached blonde and have a permanent wave. Angela said she just watched unable to work out why or how Andy was letting Pete do this to her hair. Some one had edited out what must have been a long process because suddenly the main shop lights had been put out and he was under a drier alone except for a woman who was doing his nails, she even saw herself lift up a hand and admire the newly lengthened and painted finger tips. The next clip was off Angela having the curlers removed and Pete styling the hair into a mass of curls which cascaded down over her shoulders and was clearly able to hear herself say 'Oh yes it does look nice, that is amazing'. The film then moved onto another room where Andy removed all his clothes before laying on a treatment bed. Again her own voice could be heard saying 'I know this will hurt but I also know I will look so much better once it is all removed', then the nail lady comes into shot and starts waxing her legs, Angela clearly in pain but the woman is unmoved as she continues to rip the body hair from the skin. Eventually she finishes and rubs something into the skin and Angela can see that she was enjoying this attention as a very unfeminine penis started to stand up, but it was short lived. The woman said something, Angela replied 'if you must, it would look better' the she pinches the penis hard, making it retreat until limp, then she pushes the testicles inside the groin and tapes the penis between the legs leaving a neat triangle of pubic hair at the front. The film then jumped to another room, Angela is being offered white or red knickers, taking the white ones, from the background the word 'virgin' is said, Angela says 'Off course'. The rest is shown in full. Some very realistic breasts are glued onto her chest and a very nice lacy white bra given to support them. Next Angela is being led to a spray booth given a light tan without the underwear on, then after a shower and towelling session is given her underwear back as well as the wrap she was currently wearing, which sort of broke the idea that this could be some sort of dream, but seeing the wrap both on the tv and on her body meant this had really happened. The woman next took her back to the salon chairs and turned the attention on her face. While she worked, what was being done was discussed with her, giving the technician full consent to pluck her eyebrows, pierce her ears, use long lasting make up, even giving answers when asked what colour lips and eye cream should be used. Silver eyes, gloss candy pink lips. The last thing filmed in the salon was Angela choosing a dress and shoes, a pink dress with netting under the skirt to make it flare out a little and some pink mules with a low heel.
At this point I was utterly amazed that the story I was listening too could be for real, there was an attractive woman sat across from me, but besides a drugged coffee how did she agree to so much.
Angela continued to describe the video. She was filmed walking up and down a room, someone in the background giving advice on how to walk and swing the hips, then sit down. Next Pete returned to the screen and taking her hand pulls her to him and kisses her, to her surprise she shows no negative reaction, in fact it looks like she is responding very positively. After a few minutes of this action a voice off camera says 'I have to be at Jenny's for nine if you don't mind I shall be off' The couple break off, Pete says bye, but Angela walks toward the camera and says 'Thank you so much' and from the way she walked past the camera clearly went on to give the operator a hug.
The next shot was of the couch she was then sitting on, the camera is obviously fixed, but her and Pete are not. There is plenty of intimate action going on between them. Pete has hands up her skirt, she has hands down his trousers. She then watches as first she gives Pete a blow job, followed a little while later with Pete taking her from behind, then on the floor with her legs up in the air and asking for him to push until she makes what sounds very much like an orgasm.
The film ends with her going out of the room coming back in dressed in the nightie and wrap, the couch has been pulled out to make a bed, where she cuddles up under a duvet and goes to sleep.
After a minute the recorder stops and goes back to the start where Andy is drinking the coffee in the salon. She turned away from the tv, and in her words wandered 'what the f*** happened there'
I can't help myself asking 'So why are you still dressing and I guess out on your own, no one is forcing you? Why did you not go back to being Andy? And then sue the pants off them'. But a quick check on my own position. I am perched on a stool, my leopard print mini just about hiding the stocking tops, my blouse is undone, or rather only fastened up to the bra, which is supporting my size D silicones, I have killer heels on, and my sutry make up is covering my face. I barely understand myself, why should I be asking how this woman came to be still wearing similar tarty clothes. She had a very cute way of looking down with her eyes when she was uncomfortable, and she did it then as she continued her tale.
'I was really disorientated when I had watched the recording and ended up taking a look at myself, realising that everything I had seen done to me on the tv was true, I had tanned hairless skin, my dick was between my legs, the long nails were similar to what you see now, my chest felt the weight of the breasts, then I found the bathroom and looked in a mirror and hardly recognised my face, still with make up on which was only a little smudged thanks to the long lasting cosmetics, my hair was looking slept in, but still a big head of blonde curls, the studs were there. In fact I could not believe how female I looked. But I was trying to think how to get out of wherever I was when a door opened and in walked Pete.'
She then went on to tell me how Pete made her some breakfast and apologised for what he had done, saying he had used her as a vent for his frustrations. Then apologies over she still wanted him to put right all he had done, but with the tv still running the film in the corner it came to the sex part and Pete suggested she was far keener than he had expected, he had hoped to get some sort of sexual gratification, but it seemed Angela was almost begging him in the end to make her come. The drugs and hypnosis they had used could not have explained her eagerness to have all the treatments offered, nor the positive reaction to intimacy, they had only made suggestions that she should learn what it is to be a woman.
'It was as I sat there, Pete explianing what he had done and at the same time watching myself having what looked like the best orgasm ever, something changed in me. I asked Pete if he had some clothes for me to put on. He said the dress was in the bathroom, my trousers were in the salon downstairs, and offered to go and get them as he walked out the door. While he was gone I found the dress and changed out of the nightie into it and slipped the shoes back on, brushed my hair as best I could, then when I heard Pete come back, walked out into the living room. I was uncertain why I had chosen to put the dress on other than I liked the idea of being that woman in the film.'
She looked at me 'Can you understand me wanting to do that?'
'I can understand that part very easily, good looking man, good looking woman, what is there not to understand?' I answered
She then explained how Pete, though at first a little surprised, accepted that she wanted to spend a little more time as Angela, maybe experiencing some of the things she seemed to enjoy so much the night before. Pete first took her to the salon and styled her hair back to it's former glory, then showed her the three outfits Kim had provided and left her to change. This time red underwear, a sheer red blouse and demin mini. There was also some higher heels which having no backs meant shoe size was not critical. Then after a play with the cosmetics, lip gloss and a poke in the eye with a mascara wand, she decided cross dressing was harder than it at first seemed, but considering the work that had gone into the intiial transformation, it was hardly surprising she was unable to get much done on her own she told me.
Anyway once dressed she went back upstairs to the small flat and found Pete asking what else she would like to try out, Angela descibed herself as feeling out of her depth at this point. What should she try? She had little idea what was possible. Pete then pointed out it was early afternoon and he was hungry, so he was going to get out and find some food. This raised problems such as being seen by the public and then being laughed at or worse. It took some persuasion and a strong drink to get her out of the door that first time, but soon she was in a car and being driven to a bar just down the road from where we were currently sitting. The food was immaterial to the experience, the fact Angela had gone outside dressed and looking like Pete's girlfriend was the significant event, and when Pete got teased for going straight by a couple of gay friends, the realisation dawned that Angela did look like a woman to the world. This made for a more confident girl and as they spent time in another bar drinking she allowed herself to pretend that Pete was really her partner and that she was a girlfriend even if it was only playing the role. Come late afternoon, Pete wants to get back home, so Angela tagged along with him not realising that the flat above the salon was not home. They ended up in a nice apartment in the city centre. From here Pete led her into more female experiences as he suggested that from her behaviour anyone would think she was after one thing, when she questioned him, he resited various times she had linked his arm, held his hand, kissed him in a very intimate manner and when he put a hand on her arse she had not made a move to remove it, finishing with a kiss that she did not reject either. Actually rather enjoying the experience of being the woman and letting the man take the lead. Eventually they ended up in bed with her legs in the air and this time remembering the pleasure of having something Pete called a prostate being stimulated.
She claims she fell asleep and must have been so tired it was five the next morning before she awoke. Then realised she was supposed to be at work for seven, but several things were going to make that awkward, the least of her problems being that she was miles from home and no where near her car or her work. The hair, nials, tan, breasts, not really fading make up all added up to make her choice of phoning in sick the best option. The next thing to sort out was her head, two days ago she was anti gay in a mild sort of way, now look at her, cross dressing and enjoying gay sex with a man she hardly knew, who was still asleep beside her. How was she going to get back to the normal, if rather boring life she was used to?
I was still struggling with the concept of Saturday morning Angela was straight, by Sunday night she is a confirmed gay cross dresser, and ten months later still cross dressing. So I asked what happened next, expecting to find out she got back to being a man, tried to sort her head out, but found the dressing had her hooked and she gave in like so many of us do, living a double life. As for suddenly becoming gay, maybe that was answered by the thought she had been living in denial, the homophobia a reaction to her inner truth. Who knows, but she was going to tell me, if I wanted listen.
She described the Monday as being the first day of the rest of her life. After both she and Pete had got up, niether quite sure what was meant to happen next, Pete went pragmatic and matter of fact offered to drive her to the salon, her male clothes were there and with some help from the staff, they should be able to reverse much of the changes they had done on the Saturday. With no better plan Angela took the lift with Pete, then while he got the salon opened and working, sent her to the little flat above the shop to rest until he had sorted out some spaces in the appiontments.
A little time after the shop opened, Kim went upstairs unable to believe the tale Pete had told her and wanting to see for herself that their victim was still dressed pretty much as she last saw her. Kim's first words being OMG, then a few other 'I can't believe it' phrases, followed by some flattery, telling her how good she looked, even suggesting that with a little coaching Angela would pass with ease. Angela said she argued that underneath she was a man and besides she had to get back to being who she was the week before. Kim pointed out that most people are not what they seem, what we see is rarely the real person. Pete is gay but not many people see that, her and her partner are gay as well, but the neighbours just think they a couple of girls house sharing. She was making Angela think that what is unseen need not affect what is seen, if you want to live differently to what god gave you. Then Kim went on to list all the great features Angela has, long legs, small hands, pretty face, good chin and neck, lovely hair and if she lost the stomach a cracking figure. Angela asked Kim directly if she thought she should stay as Angela, 'Not for me to say darling, but whatever you and Pete got up to this weekend surely put a smile back on Pete's face, not seen him this good in weeks, besides you do look fantastic.' After a pause Kim continued 'so what have you got to go back to, a brilliant job and career, a loving wife and family, a fantastic life just aching for you to get back there'.
Angela from the way she told this was clearly at a turning point, she had unexpectedly enjoyed herself and now Kim was asking what was she going back to, it made her pause and think again. Kim left at that point having to work in salon. Angela then explained to me her previous life, a dead end job, a small rented flat in a rough area, and an ex-girlfriend who had dumped him because in her words she thought he was dull and boring. Well this was far from boring was at the time one of her deciding thoughts.
It was lunch time before anyone else came upstairs and she had drunk all the coffee she could handle. Pete came up with a buttie and a list of things that he and the staff could do to sort her out and get her back to being a him. Over their lunch Angela tried to work out how much Pete liked her, eventually giving up and coming out bluntly telling him she had enjoyed the weekend and was there any way they could stay friends, or even go out again. Then finally asking if he knew if it was possible for her to not have any reversal treatments but to stay as Angela, at least for a few days more.
That she told me, was possibly the hardest thing she had ever done, making the choice and telling Pete what she wanted to do. The response apparently was why she never went back to being Andy. Pete told her how much he had enjoyed their weekend, he was still sorry for the actions which started it, but the results had been fantastic, and yes there was no pressure to have anything done, she could stay as she was if that was what she wanted. Then she pushed a little bit more, asking if she could use the little flat rather than going back home, which she felt would feel odd dressed as a woman. He readily agreed to that but went further and offered to take her home with him, saying with a smile that his bed is more comfortable than the fold out couch.
That clinched it really, she stayed in the flat until Pete went home, taking her with him. Then for the next couple of days she used his computer to research cross dressing and all its different forms, she would cook him a meal each evening and basically enjoy tripping around his swish apartment pretending to be a woman, even going out alone on the Wednesday afternoon as she needed some food for the evening meal.
Come the Thursday, Pete asked her what she planned on doing, she was welcome to stop as long as she wanted, but Angela could not stop without making some decisions, she had to think about work, and then there was her old flat. He left it all rather open ended with the comment that the holiday was over, however he had said Angela can stop but things would need sorting out.
Angela told me she spent ages writing pro and con lists, mulling over the options. Finally Pete invited her to join him in bed and that night spent doing things a week before she thought impossible, yet now enjoyed and looked forward too. This meant that while coming down from her orgasm, with Pete still between her legs. She asked 'So lover boy, were you serious about me stopping?' he confirmed his offer extending it to include either his apartment or the flat above the salon. But then went onto make some conditions. First was that Angela had to be fulltime, he did not want to meet Andy. Ever. She needed to get some work, he could not afford to support her completely. She had to take seriously being a woman that was convincing, he wanted to be the only one to know what was between her legs. Last she had to choose something female that would make it difficult to switch back to being a man. There followed a question and answer about what should be the defining thing that held her in the female world. Angela thought doing something to her hair should be good enough, Pete could change that easily even cut it all off, she would losose her feminity yes, and returning would be hard he agreed. The nails were too easy to trim short. More peircings, but they are removable. In the end she had a choice between a flower tattoo or a lip plumping procedure which lasted several months. What she said that followed this was a rationalisation of her options, which came down to. By Sunday she had either to get herself striaghtened out in more ways than one, or have been to the salon and had her lips injected or possibly have a tattoo, a longer term plan could be to have surgery to make Angela's breasts into real busts, but that was not an instant change but one that she could promise.
I knew what the answer must have been, but could not help thinking 'this was all rather quick, dump the old Andy, hello Angela. Besides playing house and getting shagged, she had not had much real life experience as a woman' But as I say, I knew the answer because not only was she sat infront of me, and her lips were a little fuller than you average mans. So I said 'you had your lips done I guess? the cleavage looks rather real as well, the tattoo?'
'Yes I had my lips done, amazing how it changed the look of my face. Pete did it on that Saturday after closing, he also restyled my hair, the first time he had kept the length and just gave it some curl and lightened it, this time he added streaks of golds, browns and reds, then cut the hair so I had a fringe which rested just on my eyebrow line.'
'And that was it?'
'Oh no, the Friday I had been busy, I had to go and buy some new clothes, I had three outfits that Kim had donated, but they were really going out stuff, I needed plainer things for everyday. I bought a skirt, two tops, a pair of leggings, new shoes and cosmetics. It was my way of saying to Pete, Angela wanted to stay. I had a great time that weekend, somehow being a girlfriend and having a man look after me was so nice, I enjoyed all the getting ready and being pretty, hanging around Pete as we visited some bars in town, then letting him control the sex. I did not feel used rather more a feeling of being wanted, which is very comforting. To seal my position I had a pink rose tattoo done around my navel and promised when it had healed to have a stud inserted as well.'
I was still coming to terms with this tale as she continued to tell me of how she moved on from that first week. She spent a lot of time in the flat above the salon, Kim would give her lessons on make up, a girl called Jess who had done drama coached her in mannerisms and posture, but most of the time she spent practising what she was learning of the girls and from the internet.
Winding up the old life was surprisingly easy. She gave notice on the flat, rang in work and asked if the redundancy offers were still open, they said yes, and gave his notice using holidays to work her notice. She bought a new phone and turned the old number off. Andy just disappeared she said, and Angela moved into Pete's apartment.
The final piece to confirm Angela's new life came a few weeks later, she had been keeping house for Pete, even making sure she was home before him so a meal was cooked, this meant a very public bus ride and walk down busy streets. At first it was hard but everytime she did it the tension lessened. The old car got sold, there was nowhere to park and she wanted the money for clothes which she described as mostly tart, minis and high heels. she knew what Andy had liked, and surprisingly for a gay man Pete seemed to like the 'come and get me' look. Anyway about four weeks after her sudden change she was noticing her money running out, car and last pay cheques were dwindling away so she was thinking of how to earn some money and not just live of Pete. Then Pete came back one evening in a temper, the girl who cleaned and made the coffees, the shop gopher had given her notice, or rather Pete had called to ask why she had not turned in and after a short heated exchange, he told her not to bother coming in any more. Then as he moaned about the useless teenage girls that had worked for him, she suggested taking on someone older. It took a while for the penny to drop. She started work the next morning cleaning up and keeping the customers happy with drinks and magazines.
To be honest I could not truly say I believed her story, but she was there and looking very good, clearly not wearing a wig, I could see the roots, and no false nails, if it was not for the hint of an adams apple bobbing up and down I would have sworn she was a real girl. As it was she must be living as a real girl but hiding the fact that somewhere in her past she had been a man. Whether the story of how she came to be so attractive was true, I shall never really know, but it would be nice to think it was.
Pam and Rich were relaxing after Christmas, it had been a quiet affair, the kids had left years ago just returning for family gathering as they lived so far away, but most telling was the absence of Pam’s parents who had died during the year. So with the house back to its normal quiet state, they sat enjoying a mid morning break from the housework that follows a big visit.
‘Anything you have in mind’
‘No just go and have a look, thought you might like some new clothes, maybe try something different while it doesn’t cost full price’
They finished up and set off for town, it was while they sat having a snack before hitting the shops, Pam drifted off thinking if what she had in mind would work and whether it was a really good idea. Rich had told her before they married that he was a cross dresser, he enjoyed the feel of women’s clothes and borrowed his mother’s at times even sleeping in her nightie, she felt sure he was still interested in the feel of fabrics, but trusted him not to have been wearing her things, mostly because she was size 10 and he would be a 12. Losing her parents had made her realise how brief life is and why should Rich not explore things he wanted, also like with kids who want to do something you don’t approve off, once you encourage it the interest dies. She looked at him and looked at his smooth pink face, cute, she thought, even at 50.
‘Penny for your thoughts’
‘Just thinking where we should start’ Pam replied
‘So where?’
‘The Next store’
‘So we can spend more time in the women’s than the men’s’ Rich just gave her a smile
‘Well maybe, let’s see what they have in the men’s first’
After the short walk to the first shop they looked around the men’s floor, Rich looked at his usual jeans and shirts; Pam was looking for something more adventurous she first picked out cream linen trousers, she could see him feel the linen.
‘Feel nice don’t they, like mine,’ she gave him a sly wink ‘Try them on, see what you think?’
While he went to change she continued to look and found another pair in the ladies racks, he came out to say they were too long, and she passed him the new pair, these he came out wearing to see what she thought. They were tight around the hips but flowed loosely down the legs.
‘Do you like them? She asked
‘Bit tight here’ Rich said running his hands over his bum.
‘Yeh, but it makes them look good’
Rich was obviously feeling out of his depth and suggested looking around some more.
Next they had a look through the ladies, Pam not particularly looking for herself, but was looking at things that might look ok on Rich, plain blouses, plain jumpers and trousers.
Three stores later Pam has tried nothing on, but Rich has been striped at least five times, leather pants, cashmere jumpers and a shirt with sparkly silver thread running down it.
They ended back up at the first shop, he had a brown cashmere polo neck top and Pam wanted him to get the linen pants, so he agreed and tried them again. Luckily the assistant had not put them back in the ladies, so he changed into the size 12 cream trousers with his new top. The top was not his normal long baggy fit and with the tight hipped trousers he came out feeling self-conscious.
‘Gorgeous, I think we have found you a new look’
Rich leant close to Pam, ‘they are ladies pants, I’m not so sure’
‘I know and they fit you so well I don’t care, just let me go and pay for them’
While Rich dressed himself, Pam quickly went and paid for them. Rich rejoined her and walked back to the car quiet in his own thoughts trying to work out what Pam was thinking, she had never encouraged his earlier cross dressing and now she had bought him a ladies outfit, or near enough as made no difference if you knew and she most certainly did.
‘This is a different style, are you sure about it’ he asked once in the privacy of the car.
‘Yes, it suits you and I thought you might like the feel of them’
‘Well yes, they feel nice, but you are confusing me, I have tried hard get over my early interest in clothes, and now you buy me these’
‘Maybe I am having a change of view, and after seeing you in the outfit I can’t see anything wrong’ she then leant over and kissed his cheek and slid a hand down his leg.
He turned and smiled, then disappeared into his thoughts. When they got home, Pam asked him to change while she started the meal. He obliged and came down after a longer time than expected. Not just changed but washed and smelling of a sweet cologne, on closer examination she noticed there were no lines under the tight trousers. A hand over his arse confirmed this.
‘My underpants show’ Rich informed her as he blushed
‘Commando then?’
He blushed even deeper ‘borrowed one of you thongs, hope you don’t mind’
‘Very nice aren’t they, bit tight I guess’
‘Yes’ was all Rich could manage.
Things moved slowly after the big starting day. Rich would wear the polo neck, but the trousers he felt conspicuous wearing. Pam persuaded him to wear them both and go out with her, this felt easier and he was able to relax and enjoy the clothes. As they got ready for bed she asked if he would be wearing them more often, he had to accept he would have to if he was going to enjoy them. So by Easter he was wearing them as his preferred casual outfit. Pam had bought him a pair of control thong pants that left no lines and pushed his man bits out of sight.
Clearly he was comfortable, so when they were shopping for Pam he found himself looking out for items that might suit his style as well as Pam’s more girlie statement. It was when they were home he found they had bought some size 12 knickers.
‘We got the wrong size’
‘No we didn’t’ Pam said as she gave him a big grin, which made Rich blush.
They were a lovely silky fabric, and if he had been slow to take to the linen pants the knickers were an instant success, as they became regular underwear for him. Not confident to buy some more he asked Pam too, who took it one further and bought him cami tops as well to wear under his shirts. Which he unsurprisingly did.
‘I think we could go shopping again’ Pam suggested one weekend morning
‘Anything in mind?’
‘Well you need some more clothes, and I fancy a new skirt’
Rich thought about going in jeans and rugby shirt, but it did not last long and was soon in his ladies outfit and waiting for Pam.
Shopping can be hard work, especially when you are not sure what you are looking for. Pam found her white gypsy skirt, Rich found a pair of black trousers he liked the feel of, and Pam found him a soft cotton blouse they thought would look good under a jumper so the buttons were hidden. He also bought a pair of androgynous sandals, which meant when they got home and she suggested going out to eat, he could dress totally in women’s clothes.
Rich’s office job changed and he could work form home sometimes but when at work he was in a private cubicle, which meant he only really met the people he wanted too. This lead to his wearing the black trousers to work, which meant Pam, urged him to get another pair.
Still changes happened slowly, in the summer Pam was filing her nails and suggested Rich should take more care of his, and gave him a manicure, finishing him off with a matt coat of polish, she said to protect them.
The next big event in the coming out of Rich was his hair, it was never short, but would grow till it’s length annoyed him, and at the time it was the fringe but Pam kept asking him not to cut it and soon he could hold it behind his ears.
Talking of ears, he surprised her one day coming home with small gold studs in his lobes, and to his surprise, no one at work commented which made him bolder in his cross dressing, eventually wearing all his clothes to work.
Soon it was coming up to Christmas again and she wanted Rich to embrace far more of the dressing, not only did she like the new look, but it made Rich happier. So she suggested that after the kids had gone back to their homes she treat him to a few special treats.
But first they had Christmas to enjoy. Their daughter was curious about the uncut hair and studs, but she only saw the black trousers and never guessed their true gender. The son never noticed a thing.
As soon as they were gone Pam got out her extra presents, gold hoops and a satin blouse. He eagerly slipped them on, and then Pam came out with the first of her big surprises. The blouse did not fit well as the darts made it look odd without a womanly chest and presented him with her next gift, a padded bra. This he needed help with, not only being persuaded it was the right thing to do, but also with the fastener. Now back in his better fitting fitted blouse she dropped her biggest shock. After all those months of persuading him not to get his haircut, now she wanted him to have a trim.
‘Where on earth could I possibly get a cut at this time of year, and dressed like this?’
‘Oh that one is easy, you know Denise who does my hair, well I was telling her how long yours was and she offered to sort you out’
Rich had a worried look ‘You have made me an appointment, haven’t you’
‘Yes’
‘When?’
‘This morning’ Pam said with a smile, ‘You have the salon to yourself, she is supposed to be shut’
‘Well OK, just let me change’
‘No you look great, white shirt, black trousers, slip a coat on and I shall drive you there’ Pam could see he looked nervous, so with a gentle kiss as she swept her hand through his hair, she weakened his resistance. ‘Come on and enjoy yourself’
Rich surprised himself as he got up and meekly followed her.
Denise turned out to be Denis a stereotypical camp hairdresser which put Rich of his stride at first, but after he had talked about this and that to Pam for 5 minutes Rich was feeling a little more relaxed as Denis was running his comb around the hair.
‘So what do you fancy’
‘I have no idea really, usually it just gets trimmed when it annoys me, what do you suggest’
‘Well if it is up to me. Let me ask you, would you be up to using a gel or moose if I cut a style that needed a little help staying in place’
‘I guess not, is it hard to do?’
‘Oh no, you just rub it in as you are drying usually. So let’s get started, over here to wash your beautiful locks first’
As Denis worked they chatted, Denis about his clothes and where Rich could find some more, Rich talked about his clothes and Pam’s encouragement. Denis knew all about this and more it seemed, a stylist seems to be a confessor as well Rich commented, to which Denis gave a big gesture expressing how many tales he had heard from his ladies. Denis then let on that he had been unsure if Rich would turn up, and if he did what would he wear, Pam had said that the clothes Rich turned up in should determine the style. Rich suddenly realised that wearing a fitted satin blouse with a bra underneath, would mean only one thing; Denis would have cut his hair in a feminine style. As this fact sank in Denis unveiled the new Rich. His once shaggy hair was gone, a straighter style that curled under just off his shoulders and flicked across his forehead was most definitely not a man’s first choice, but it had been Denis’s. As Rich looked in the mirror thinking how he was going to face Pam and the world looking like this Denis broke in,
‘You are a cross dresser? Right, well make the most of it; get some heels and something nice to go with that divine blouse and I shall show you around the places you and I can be accepted’
Rich could hardly string words together.
‘I have to see a man about a dog in fifteen minutes, so I need to lock up, here’s my number if you fancy a night out give me a call’
With that Rich found himself outside feeling very conspicuous and strangely elated to be out dressed so femininely. Pam turned up as the door was being locked.
‘Look at you, Denis you are wonderful, how can I repay you?’
‘Just make sure he treats it right and comes back to me for a trim every now and then’ he said as he cheek kissed them both.
Pam turned to Rich as Denis walked away, ‘Now how does that feel, because it looks fantastic’
‘Not sure yet, Denis suggested I get some heels and something to go with the blouse’ Rich ventured
‘How about some make up as well, do the whole trip’ Pam looked at him for the unspoken hints, she could see he was unsure but had not dismissed it, otherwise why was he wearing such a neat bob and not freaking out.
Within an hour they had been to a shop Denis had suggested and come away with a cream vest top, a brown shrug, brown trousers with enormous bottoms and a pair of gold sandals with 2” heels which was just enough to lift the hem of the floor. Next Pam insisted he get some make up, nothing to brazen, he did not shave so light foundation, gold and browns for the eyes, and pink for his lips. Then it was home to check out what the bags contained. Soon Rich was washed and changed into his new outfit, with Pam giving him a quick make up lesson.
‘Ever thought of doing this as a kid?’ she asked
‘No, but I would be lying if I said the idea had not crossed my mind since’
As she moved away after doing the last stroke with the lip wand she opened her mouth but nothing came out. Eventually managing ‘Take a walk over there so I can get a full view’ he moved away ‘Stunning, you are not male you know, we have created a beautiful woman’ She left Rich looking in the mirror trying to work out where his masculinity had gone because all he could see was a well dressed female.
‘Denis says he will meet us at eight in town and show us around’
‘Why have you done that, I cant go out, people will laugh, I only want to feel the clothes’ he rambled on with excuses till Pam stopped him.
‘Shut up and listen. This has taken both of us a lot of effort, you look great, let’s not waste it sitting indoors, Denis knows some great places, how about we drop all our inhibitions and just go and doing something totally out of character’
‘And me dressed like this is normal?’ Rich tried to come back with.
‘Besides I fancy a night out, and I like Denis. Now find that gold clutch bag, there is a pashmina in my drawer you can borrow, then go and call Denis to tell him you are coming as well’
The evening went well, Denis had his partner a well dressed man called John, Denis was even camper than before and wearing a pink shirt with white trousers stood out more than Rich who was looking like a woman through and through.
John and Denis showed them around the bars they used, meeting other friends with kisses sometimes more intimate than one would expect from hetero friends. Denis was a perfect girl for John’s man, but when Denis went off chatting with a friend and Pam was chatting to a newfound friend, John leant over to Rich and confided that he wished Denis would dress like him. Rich had never thought of himself as attractive before, but John was obviously flirting with him, and to Rich it felt great. As the night wore on, Denis suggested a club, as he wanted to dance, John didn’t but smiled and led the way. Another gin and Rich was finding heels were not so bad to dance in, and as men came to ask Pam for a dance which she accepted, Rich would find himself dancing with John or Denis, sometimes even a stranger. In the early hours the DJ finished with some slow songs, John and Denis found each other, Pam had been dancing with particularly well-toned man who just continued to dance with her getting closer with each move. Rich was about to leave and get a drink when a man caught his arm and asked for a dance, the grip made Rich think it would be easier to say yes, so he did, the partner soon had his hands around the waist and pulling them together, the man’s erection easily felt on his hips, then he found his lips being kissed and a tongue finding it’s way in. it was a most wonderful dance and his first as a woman, well sort of.
An hour later Pam and Rich are home and cleaning off their make up. Pam has one last gift, a silk nightie for Rich to sleep in. It was not until the morning that they have slept and got over the alcohol, and are able to consider what happened the night before.
Rich spends ages trying to work out how to get his hair looking good as he happily sits in a bra knickers and cami. Pam eventually wakes and comes to his rescue showing him how to use the moose, dryer and brush. Then she helps him redo his make up, gets him to wear the satin blouse outfit before asking how he felt about the evening. Rich said he was not happy with her being so intimate with other men, but her come back was the observations of Rich’s slow dance and how he was fighting the man off. They finished saying they would definitely be out again, neither sure how to say, as soon as possible please.
The next couple of days are spent immersing Rich in femininity, Pam shows him how to pluck his eyebrows, do his own make up and after all that time keeping his nails neat she buys a set of false nails which she insists must be a deep pink, Rich does not object as he is enjoying his Christmas break too much.
Rich knew it would come, two days after going to the salon he is fully dressed and Pam suggests shopping. Rich knew it would be for him, what he did not know was what they would be shopping for. After a long shop they arrived home with plenty of bags and even more clothes. He now had a day outfit of wrap over top, double layer skirt and boots, a figure hugging short dress Pam said would be great for going out at night in with stiletto sandals. Along with several pieces of jewellery, make up and what he considered sexy underwear. Rich was not aware but Denis and Pam were setting him up, each for their own reasons.
So when he got a call from Denis asking him out he suspected nothing. Pam suggested the dress, so he dressed in his new stockings, dress and best jewellery, then having practised in the high heels took them for their maiden outing.
John and Denis were waiting at a table in a smart bar for Pam and Rich with a bottle of ‘champagne’ which slipped down far to easily, then as they moved onto another bar Rich stumbled and was caught by John who offered his arm just in case it happened again. The evening went well, Pam and Denis kept on disappearing, then when they got to a club with a dance floor, Pam was of with the first man that looked at her and John asked Rich for a dance which he accepted. Rich noticed that Denis and Pam though around were not sitting with them, and as another bottle of wine emptied he realised he was alone with John, who finished the evening with a few slow dances which included intimated touching and kissing. John only lived close and as Pam had gone of with Denis, the offer of his flat seemed very attractive.
Once behind closed doors, John repeated how much he liked Rich and the fact he was a man who looked like a beautiful woman turned him on. Rich was unaware of where this was going but was certainly enjoying the way he was being treated. When John slid the zip down the back of the dress revealing Rich’s lacy black bra, thong and suspenders, still on his heels John pointed out how sexy he was, Rich was now completely spell bound. John explained how he knew it was his first time and he would be gentle with him.
And so Rich lost his virginity, to his complete surprise when he got up in the morning he found a bag with his other skirt and all the make up he would need in it. There being no alternative he dressed, John told him how much he had enjoyed the night and would be happy to repeat it anytime he wanted. But Rich was interested in why the bag was there and what had Pam been up to.
He turned up at his own front door looking very attractive, Pam was sitting reading and obviously waiting for him.
‘So, how the bag get there, I am guessing you had some hand in this’
‘Sit down and calm down’ Pam started ‘Did you enjoy yourself? Was it terrible? Would you fancy doing it again?’
‘What?’ Rich was confused.
Pam explained how since Rich had not been able to get a proper erection for ages she thought about the alternatives, and this was one of them, he could have sex without the need for an erection, he would just enjoy the pleasure.
‘It is painful you know’
‘But did you come?’
‘Well yes’ he admitted
‘So there you are, you can enjoy your cross dressing and a bit more’ Pam said with a smile.
‘But what about you?’
‘Don’t worry about me, if you can play away to get what I can’t provide, then so shall I.’ she said with a cheeky grin spreading across her face, adding ‘I still love you, that is why I have been prepared to do this for you’
My name is Keane Smith.
I like to sing.
I like going to bars with friends.
I did not know I would like the new life these pleasures introduced me to.
My name is Keane Smith and I had finished college with a degree in Computer Science and had a great job troubleshooting for a software company. My hours were very flexible and most of my time was spent working out of the office doing calls for other companies. This allowed me a great deal of independence to do some of the things I really enjoy. I have always loved to sing and with the ongoing craze of Karaoke bars I have been able to satisfy my passion. I have a slightly higher voice than most boys and always sang at church and in the chorus at high school. As a matter of fact, some of my friends from the chorus also enjoyed going out to the bars on Karaoke nights. It was fun just getting up to sing and some of the bars held monthly contests with some nice cash prizes. Nothing excites me more than when someone gets up sings a "knock me dead" song that just wows the audience. I have a very good voice and always get a nice small round of applause but never have been able to do that to an audience. I even tried to pick the bigger songs but somehow just never pulled it off. One night, I sang "Crazy" a big song from a great singer, Patsy Cline, and really thought I sang it great. Some of my friends saw my disappointment when I received my usual applause and tried to encourage me. Janet, my old friend from high school chorus, said something that really made me think. If you were a pretty girl up there doing that same song, you would have knocked them dead.
I dismissed the idea as daft, but at the back of my mind it added to previous comments, some well meant others cruel. Maybe my voice not breaking was the main thing that made me stand out, but my small thin frame was not a help when I was teased about being a weedy kid who could never make any team other than chess. But despite my worries that I was not your typical male I had had a few girlfriends who had appreciated my softer personality. Currently though I was just part of the group and was enjoying the option of being on my own or going to the bars for fun with friends and no ties.
So two weeks later, the comment Janet had made about 'Crazy' was fading but still sat there along with the gay and girlie comments from the past. We tried a new club, the host was an amazing drag queen; she/he could really get the audience going, and at times would make fun of the truly awful singers. Dan went up first and did a Queen number which went down well, then Janet tried a Spice Girls tune which was less successful. Next I went up to sing 'Dancing in the street' thinking of the Mick Jagger version, but when the music started it sounded wrong and in the wrong key, but as I listened, it did fit and I got into the song after a few lines. It was coming out like a Motown tune, which I later found out was where it was first recorded. Anyway by the end I had more or less got it, and to my surprise the crowd loved it, even the host praised my attempt and apologized for putting that backing track on, giving me a big hug and telling the bar to give me a drink on her.
This was all rather unexpected, good applause and a free drink, not bad for a half decent song. Later in the evening the host singled me out and asked if I would do the song again, I asked why, she said so I could give it a proper go, I asked which backing track, Motown off course she replied, apparently I have a good soul voice. Well that was news to me, but flattery will always turn me and I went to sing Dancing again, this time I was ready for it and knew what I was trying to sing, and nailed it. There are a few times something goes really well and this was one of those times. My friends cheered and the crowd clapped, then the host came and once again told me how good I was and suggested I was that nights best performance, which meant if no one else bettered me I would get a voucher for free drinks at the bar so my friends were hoping for rubbish singing from then on.
At the end of the evening I did indeed win the drinks voucher, which of course meant we had to return so we could claim the prize. So a week later I and some of the friendship group turned up at the bar to help me drink my prize. The drag queen hostess seemed thrilled that we were back, glad for some decent singers he said. With a few free drinks inside me it did not take much for me to be persuaded to do a Whitney Houston song, and later a Freda Paine song, Band of gold, another soul tune. Both of which I sang well but did need to push myself for the higher notes. At the end Dan won but it did mean we would be back to drink his winnings another night. What I did not expect was to be back on my own for a different reason.
April, well that was what he called himself when in drag, took me to one side after Dan had got his vouchers, and suggested I meet the bar owner, a big burly bloke called Pete. Being easy going I agreed to a time, when April was working and Pete would be around. So three days later I am in a scruffy back office after being offered a drink at the bar when I first entered. April has not changed yet and is looking very odd in sweat shirt and jogging pants with a baseball cap covering his hair. Pete is a big man who you could tell was used to getting his own way, though he did not seem at all threatening to me. April had obviously told his boss about me and the singing, and was telling him that he should hear me sing the soul classics, for a bloke I was great at the female tunes. I was a bit slow to catch onto where this was going and I virtually had to be told that with my voice and looks I would make a good understudy and assistant for April. At this point I got the nerves and started to explain how I only sang for fun, that karaoke was a game with friends, besides there was a strong hint that April's assistant would be in drag also. They thought I already knew that, but I was backing out of any commitment when Pete mentioned money. For an evening’s work he would pay me what I earned in two days on computers, and that was if I worked full days which was not very often as I get paid per job by the agency. He also offered to foot the bill for stage clothes and April would teach me about how to prepare myself, all I had to do was sing a few songs of an evening and help April with the hosting. Being a cautious sort of person who likes to think things through I asked if I could think about it. Their response, I had till Thursday as they needed to know if they should go with me or get a queen they knew but was a bit unreliable and did not sing as well as me. So I had two days to decide, what should I do?
I had two days to make my mind up, the money was tempting and getting paid to sing has always appealed, it was just the way in which I would have to achieve those things. I would have to dress as a woman, an over dressed woman at that, a parody if you like of them. I rang Janet who had made the comment all those weeks ago if she thought I could seriously go through with the proposal and do it well. Without a moments hesitation she told me I would be a fool to pass up the opportunity, not just for the money and the singing but to prove her right, that I could look the part and be a knock out with the Motown tunes, even 'crazy' if I had another go at it. Still wanting reassurance it was a good idea or support for it being a daft suggestion, I called round to possibly my oldest friend's flat, over a beer he listened to my dilemma. Then he quite matter of factly told me the good points outweighed the bad ones, of which he could only see one, which was I might get some teasing for the dressing up, but he knew I had put up with it before, he also confirmed that he was sure that I was a confirmed heterosexual, which made me feel a good bit stronger as that was one of the things troubling me, would wearing a dress make me gay. According to Steve it would not.
Decision made I rang the bar and told them of my decision, I am not sure what response I expected, but there was only bar staff on and they said they would take a message, I felt a little flat after all my hard thinking of the past days. That was Wednesday lunch time, I had to wait for eight o'clock that evening before I heard from the bar. Pete rang to tell me he knew I would do it and was surprised it had taken me so long to come back to him. I was to be at the bar for mid afternoon Thursday, April would sort me out with a costume and give me some instruction on makeup etc, then I could have a practice on Friday but I was to be there Saturday for my first performance. He finished by saying he knew I would be great and I had nothing to worry about, and he was looking forward to Saturday already.
Pete might have been looking forward to Saturday but I was not. I had said I would do it so I turned up mid afternoon on the Thursday to find the bar nearly empty, lunch time over and the pint on the way home drinkers not appeared yet. I told the woman behind the bar I was looking for April as I paid for my drink. Half an hour later April appears in jeans and t shirt, I was not sure what I was expecting but something more camp or feminine would have fitted my imagination. He took me to one side and chatted, making sure I was fully aware of what Pete and he would want me to do. I said I would give it a go, and if I was no good they should tell me before I can embarrass everyone including myself. April brushed my concerns aside telling me I was a natural. Then we got onto the costume, I had no idea what he was talking about, so took me through to a small room which doubled as his changing room among other things it seemed, judging by the various bits of equipment lying about. He held up a few of the dresses in front of me until he decided a sparkly blue one would be good. Then he started to get personal, asking about shaving and grooming. Suggesting that, I shave my legs and arms before Friday. And give myself a good shower, moisturizing after. Then he pulled out a few wigs, my short tight curly hair he said would be great for the Kirby grips to hold the wig to my hair and found a black one that might just be OK. Then he started to fuss over my skin color, apparently my dark skin would need different colors to the ones he used but looking at his watch told me he knew a shop where they would have supplies and would not be shut yet. So ten minutes later I am stood in a ladies hair salon having creams rubbed into my face to see if it is the right shade, and Ruby (the proprietor) telling me how she wishes cosmetic companies would realize black girls like make up just as much as white ones, but where is it in mainstream shops. I guessed a usual little rant for hers. But she made a good sale out of April, who told her I might well, be back for a nice head of hair if things went well. She replied that she already had in mind what would look good on me, I blushed for no reason I could think of, just embarrassed how these two talked about me I guess.
I stopped around so I could see how April prepared himself for the evening. It was all rather strange watching a man turn himself into a woman. First he undressed and put on some underwear, nothing like women wear, the bra was already filled with foam I guess, and the knickers were extra strong and took some getting right if the amount of rearranging he did with them was anything to go by. Next he sat in front of a mirror and applied his make up, then lifting a long white dress from the rack, slipped his body into it. Then he took out a long curly blonde wig and attached it to his head. Last he glued on some long nails which were already colored a sparkly pink. Forgot to tell you about the shoes, white narrow high heels. That about did it for me, I was expected to do all this; I was getting rather nervous that I could manage to cope with everything, but the shoes looked very uncomfortable indeed.
Friday I had one job that I cleared up easily, then went to file my jobs for the week so I could get paid for them, but all the time my mind was spinning with the thought that when I was finished I was going to go home and shave all over in preparation for my rehearsal. Now, I don't have much body hair and what little I do have will take ages to regrow, so it was with some regret that I stood in the shower and pulled a ladies razor up my leg, but having left a bald stripe up one I had to complete the rest or it would look very odd. After much careful shaving I stood in front of the mirror to check out the results, I looked the same but different, the main change was around the groin, April had said nothing about that area but I reckoned you never see women with hair showing outside bikini bottoms so I had trimmed my pubic hair into a neat V. I even strangely liked the shaved me.
It was when I dressed to go to the bar that I had my next revelation, my skin was so sensitive, my skin could feel the clothes without the hairy barrier, my jeans feeling very coarse but the cotton shirt was pleasingly soft. I arrived at six as agreed with April and this time found him dressed in a smart business suit, not a man's but that of a woman's. Blue with pink pinstripe and a pink silk blouse beneath it, and on his feet, heels. This was for some reason more the idea I had of how April would be dressed, and he did look every part a sexy lady. He swept me up and led me by the hand to the changing room. He was in a good mood and his mood spread to me as he felt my arms and complimented me on how smooth my skin was. Over the next hour April transformed me into his assistant. I had his spare bra clipped around my chest, then his 'gaff' which held everything down below out of sight. I was further complimented on my shaving when it was noticed how neat my panty line was. Then he painted my face, I can think of no other description for this as he spread colors over my skin. Then he fixed the long hair to my scalp with the Kirby grips and the new sensation of hair brushing my shoulders made my skin ticklish. My next new experience was putting tights on, rolling each leg up one at a time then smoothing the fine glossy fabric up my legs was very unusual to say the least. Next the dress, I had taken little notice of it besides the color when April had picked it out, but now as I climbed into it and pulled it up my body I could not help but notice the contrast between the outside material which was quite harsh as it seemed to have fine metal threads in it to give the sparkly look, and, the incredibly smooth lining which slid over my bare skin making it tingle. Once on I got a better look at what I was wearing after the rear zip had been pulled up. It had a high neck, flowing down to my new and to my eyes enormous bust, then pulled into my waist before hugging my hips, from here the lycra type fabric changed as the skirt flared out into what I can best describe as a short train. The skirt came nearly to the floor at the back but swept up the sides to reveal an awful lot of leg, the glossy tights showing themselves very clearly as I looked down. Now for the finishing touches April announced, big bangles on each wrist, big clip on ear rings, a couple of big rings for my fingers, then the moment I had been dreading the shoes. Me and April are not the same size, he is taller and bigger built than me, hence the stretchy dress fabric, but his feet are size 10 while mine a size 6 which he was envious off, apparently I would have a great choice of footwear and not just the specialist shops, I did not know whether to be pleased or not, but for this weekend he had borrowed a pair of shoes from a friend, white sling backs with holes for my toes to poke through, to my relief the heels were lower than I saw April wearing, but when I took my first steps I recognized they were nothing like my usual Nikes.
There being little space in the dressing room, April suggested I go into the corridor and practice walking about. It was on my own that I got a full sensory overload from what I was wearing. The shoes were making me walk carefully and with a bit of a sway as I balanced each step, this made the nylon around my legs rub, and the dress lining ride over my hips and chest in a luxuriously smooth caress while the length at the back of the skirt was brushing around my ankles, the hair was tickling my bare shoulders and entering my field of vision, all the time I could feel the bangles on my wrists and the ear rings tugging at my lobes. I was so full of new sensations that I forgot my doubts about whether this was a good idea or not, I was lost in the moment.
April seemed to be ready in no time at all coming out to disturb my reverie. He looked quite stunning in a full length halter neck dress with a side split to his panties, my first thought was 'very sexy' but then recoiled as I remembered this was not a woman I was looking at but a man. April was all business and took me onto the stage area to show me the equipment we would be using and where things were. It was now eight o'clock and things were getting busier, April took the background CD from the player and put in his choice which was more upbeat but singable tunes. Then after a slow walk to the bar for a soft drink and a chat with friends and regulars he got up on stage and started the evenings show. This being Friday it was mostly karaoke with the singers being encouraged or teased by April, but when there was no keen singer from the audience he got me to go up and sing Dancing in the street. Somewhere in that song I lost my Keane image of myself as I sang I imagined how I looked and sounded, and was portraying a soul singer from the 70s. My usual style is to just stand and sing as I would in a choir, but now I felt able to gesture with my hands and move my feet, I was acting a role of someone else and it was so liberating.
I mostly just stood at the back watching, coming on stage a few times to sing when it was quiet. Then at the end I was given the job of presenting the Karaoke voucher, April announced me as Kiki and sent me forward to present the prize to a not particularly good looking man, but a good singer none the less, I remembered what April had done when I won and gave the man a hug and a big kiss on the cheek before passing the card over. I could see he was a little awkward about being kissed by what he knew was a man, so as he parted I patted his arse and blew him a kiss, he squirmed some more but smiled back, he knew it was part of the show.
Then it was over, while the bar staff tidied up we sat and drank a very nice alcoholic lime drink while April ran over the evening’s highs and lows. He loved my singing, but maybe more movement, watch a DVD of a diva and see how they do it. Be a bit more on show, don't hide at the back when I was not doing something, go out and encourage the punters. Loved the presentation at the end, be saucy the customers love a bit of that; make the most of the ambiguity the drag queen role creates. I promised to try the following night, tonight had been a watch and learn mainly for me, and I had learnt a lot I assured him. Then it was off to clean up and get back to normal Keane clothes and back to my regular life.
But before that happened I got a completely new perspective on April. As I came out of the changing area having followed his instructions about cleansing make up and putting the costume away, I was met by the sexy image of April in business suit, minus the jacket and showing a now very revealing blouse, and smelling of a heady perfume. At about the same time a man I had seen in the bar came into the room and immediately took April in a long a passionate kiss. I just stood there like an awkward schoolchild not knowing where to look, eventually they broke their embrace and April introduced me 'Jason, this is Kiki my new girl' I smiled and said hello, Jason replied 'I have heard a lot about you, but when I saw you tonight I have to agree with April, you will be great' he leant over and kissed my cheek ever so gently, 'maybe you would like to join us?' April cut in at this 'No she wouldn't, you cheeky boy, tonight I want you all to myself' and as April went to kiss Jason his long painted nails drew up Jason's ever growing bulge at the front of his pants.
I said my good byes to them and the bar staff, and then went to get a taxi home. All the while thinking through the evening’s events, and new experiences. But the ones that kept coming back to my thoughts were the last ones where Jason had gently kissed my cheek which was so sensuous I wanted every kiss to be like that, and the way April had introduced me as Kiki and referred to me as she, while off stage and dressed as Keane, but what impressed me most was that I had not realized April had done it till I left them. Did I look so feminine or was April just used to calling me by the stage name, I expected it was the second, but had serious worries that the first could be true also, and if I did look feminine what I was going to do about, if anything. Needless to say I had a less than sound sleep that night.
By the time Janet called at ten the next morning, I was full of doubts about who I was. So concerned that after the ‘Hello, how are you?’ Greeting hug. ‘Do you want a coffee’ routine, I immediately asked if she thought I was gay. Her response was to laugh and hug me. No was the answer, and as she pointed out it might have been a few months ago but we had spent a few nights together and from what she remembered I was all man, but then with a twinkle in her eye, suggested sexuality is never black and white, but shades of grey and who knows what percentage male to female I truly am. Then as we hugged she kissed me and my erection grew until it was so hard she noticed, with her hand resting on my groin she smiled and told me that with that response I at least fancied her if not all women, then with that twinkle added, men I would have to find out for myself.
The day passed quickly after Janet left having proved that I had fully functioning male genitals. I had my usual weekend chores to do as well as have an early shower and moisturize all over, it helps the skin when you shave all over April had told me, and as I was ignorant of such things did as he suggested. I had also brought home a few items so I could sort myself out before April would prepare me, I had the gaff to put on, which I had rinsed through with the tights. I also had my hair which needed a good brushing before I wore it again. So about six I walked into the bar to be welcomed by the bar staff who remembered me from the night before, wearing my tackle tightly restricted inside the gaff, and my other things in a shoulder bag. I had chosen a particularly soft shirt to wear and my linen trousers so I could enjoy the feel of them against my skin. I don't know why but I had a good feeling about me and could tell I was smiling a lot.
April was already at the bar, this time in cream dress that flattered the bust the skirt part floating around his body as he moved, once again I had to remind myself this was a man I was looking at and thinking how sexy he looked. 'You all set for tonight?' he asked, I smiled and said I was. Then he pulled out a running order of what we would be doing, Saturday was not all karaoke, if any of the past winners wanted to come along and sing that was fine, but April would do some chat and comedy with the audience, I was down to sing about six songs, and there was a male stripper as a main attraction. Then I had to go through the dressing up part all over again, April quietly applying makeup and giving me advice on how to do things. I was in the same dress, but April chose a dress which looked like two meringues on top of one another, one around the chest the other covering the hips, with a wide belt between them pulling the waist in, his long legs coming out the bottom and wearing towering heels again. With plenty of colorful make up and a big hair wig he looked every part a drag queen and nowhere near as good as when I first saw him in the cream dress. I said nothing but knew I would think this contrast over when I had a moment to myself.
The night went well, I sang all the songs I had done before and couple more that were well known easy ones, and I even got into the character of the singer, and moved about in a way I had seen on a video I had watched in the afternoon. When not singing I would play stooge to some of April's jokes, and mingle with the customers as I went for drinks for myself and April. What did take me by surprise was my reaction to the stripper, I was on stage to just collect clothes that he discarded, and give him some help if he needed, what I did not expect was to become part of the act. He was half way through his undressing when he beckoned for me to tug a string and I ended up with his trousers in my hand, I expected it but was able to appear shocked, then he squirted some foam onto my hand and encouraged me to rub it over his very well muscled chest, then over his six pack, but slapped my hand when I went lower. He then got a customer up on stage and played with them, the whole act being quite risqué. He eventually turned his back to the crowd and deftly removed his man pouch passing it to me who was stood in front of him and could see him in all his nakedness. I am thinking my face was a picture. Then April turned the lights off and the small stage was dark for us to get off unseen.
Sean the stripper hugged me once we were out of sight, 'You were brilliant out there' I was lost for words 'you are perfect, don't ever lose that innocent look' April had put a CD on and came to join us and congratulate us on a great performance and told me I was on next to sing but missed out what was going to be played. I was left with no time to object as the music started and the words started to roll on the monitor, it was one of Donna Summer's very close to the knuckle songs about making love to a nice man, I caught a look at April who was smiling like a Cheshire cat and making suggestive gestures like licking a finger. I just went for it and played the role.
We finished about midnight and made our way slowly through the bar to the quietness of the changing room. Pete followed us in, gave April a kiss and patted my bum telling me I was fantastic. Then he gave me my pay, a quick look confirmed he was paying me more than he had said he would. Last week had been a quiet week and what I had in my hand for one evenings work equaled half that I could expect from my computer job, I was shocked. Then he took me to one side, he wanted to know if was up for doing this regularly, he would understand if the experience had freaked me out a little, I bumbled something about how there was plenty of new things I needed to get used to, but I lied when I said nothing had freaked me out, but told the truth when I said I would do it regularly. This seemed to please him as the frown on his face was replaced by a smile, then he told me to get in touch next week he would make some arrangements with Ruby to kit me out properly and stop using April's cast offs. All I could say was 'well thank you, shall be in touch'
As Pete left Jason appeared, congratulated me, then went to kiss April. I went to clean up and change reappearing to find April once more looking female sexy and Jason looking like a dog with a bone. I wished them good night but as the bar was still open stayed and had a drink and a chat with some of the staff, I could not get enough of their flattery. Eventually I went home and realized I had never been called Keane always Kiki no matter how I was dressed. At the bar I was Kiki and that appealed to me, I could keep the parts of my life separate if no one was going to call me Keane when I was at the bar and no one would call me Kiki when I was visiting sick computers. Neat.
I had a better night’s sleep and was woken by Dan ringing to find out how the job had gone. I meet him later at a local bar and told him whatever he asked, I tried to explain how it felt to play a character like the sexy Donna Summer, he was a little shocked to realize I had smooth soft arms, and asked the inevitable question was I gay, no I replied but did not tell him about my midday fun with Janet the day before. Then he asked if I was going to be getting into dresses more often, I confidently said I only wore a dress for the show I had no intentions of wandering about town in a skirt, to which he said it was shame as I could look good in a skirt. That got him a slap, unfortunately not a heavy man's slap more a weak girly one, but it was just the way we were sitting and I could not get a good swing at him.
Monday afternoon I had a call from Ruby asking when I would like to make an appointment so we could spend some of Pete's money, I looked at my diary and we agreed on Wednesday morning, she told me to come prepared, when I asked what she meant she sighed, 'I did not believe Pete when he said you were a complete novice, but you are. Don't worry we shall fix you up with everything, just bring yourself'
I arrived on the Wednesday at the appointed time outside Ruby's ethnic beauty parlor. A bit nervous if I am honest, ladies salons are were not a familiar haunt of mine then and this was like a forbidden place that men did not go into. But I walked in trying to feel confident, Ruby recognized me and gestured to a chair where I could wait until she finished with her customer. She was five minutes then came over to me, the first thing she said was 'Welcome Kiki, follow me and we shall spend some of Pete's money and make you look like a star' somehow it was being called Kiki and that she was going to give me everything for the drag role that made me nervous and excited at the same time. Nervous because it was new and totally out of my experience, exciting because it was new and totally out of my experience.
We started at the back of the shop where she suggested I might feel more relaxed, I thought less embarrassed as she took out samples of the cosmetics April had bought a few nights before and taught me how to apply them. An hour later I had cleaned and reapplied them three times, Ruby saying I was pretty good already but I should maybe practice at home a few times just to get myself easier with them. Then before I cleaned off for a last time she produced several wigs, being an ethnic salon her selection was more suited to my skin color she explained and she tried on various styles. We had discussed what sort of look I was trying for, when I said I had no idea she said great, she could use all her skills on a blank canvas, the only thing she did consider was that I was singing mostly soul numbers, but I did say that I was not certain whether this would continue. So with soul diva in mind she choose my hair style. I ended up with a long dark brown wig with plenty of small curls so it gave it plenty of body, Ruby assured me the color was great but I could restyle it to a straighter cut or give it more frizz and make it into a really big hair look. Whatever I did I was to take it back every so often for her to recondition it, and that was on top of the care program she gave me to do so it stayed in good condition. Then while sat there with makeup and hair all in place looking at myself in the mirror, Ruby went off to find some more things, I looked at my reflection and realized how feminine I looked, Ruby's efforts had transformed me in ways I never imagined. I sprang out of my reverie when she returned with what I found out were false nails. I then had a lesson in applying them, painting them and removing them. She also gave me a set of false eyelashes but suggested I call into the shop so she could put them on as they are not so nice to be putting on and off just for a few minutes. I promised to be round before my next show. Then I had to clean everything off, we were going shopping.
First stop was a specialist shop for theatre performers, a limited range for drag but enough she told me. I was fitted with a girdle that kept everything below squashed flat, two chicken fillets as they called them and a bra to put them in. There was a certain amount of fiddling with the straps, but Ruby and the sales assistant made comments about how once I was confident of the position I should go for strapless as I have such good shoulders and nice neck. In my ignorance I said that it was something I would remember to try in the future. We were asked if I needed a corset or waspie but Ruby said that would depend on the dress. They did try to sell us a dress but they had nothing Ruby said was suitable and we left with our purchases. The next part was the hardest, Ruby took me round regular ladies fashion shops, at first I thought she would want me to try things on as at the theatre place, but my fears were downgraded to moderate anxiety from terror when she told me we could return them if they did not fit after trying them at home.
We ended up back to her salon with four dresses. In a back room I had to get into the new underwear then try on each dress. A white mini dress with big bell sleeves. A gold dress with a long tail to my left ankle, the skirt hem rising across my legs to a point high on my thigh just below the panties. A red Spanish style dress with lots of frills and a big skirt. And a dress best described as a corset with lots of net attached to the bottom. All of them Ruby said would be suitable for the drag queen assistant look she had in mind, but after getting me to try on the mini and the long gold dress again, she picked the gold one.
Then we were off again, returning the three unwanted dresses, then on to get the remaining items. Shoes she insisted for the part had to be high and spike, when I raised objections about them being uncomfortable and dangerous, she just told me some women wear them all the time, and I would be expected to wear even higher ones if I could. Part of the job I said, she agreed and I had to suffer the embarrassment of trying on high heels looking like a man, but because I had a small foot I was sorted out quickly with my gold stilettos. Next we needed nylons as she called them, I knew them as tights. She had wanted me in stockings but the dress was too short so tights would be better, three pairs of nude with a sparkle in them ended up in the bag. Then back to the theatre shop and the most uncomfortable fitting I had. The gold dress emphasized the bust then fitted around my stomach meaning that a flat abdomen would look best. To achieve this I was given a strong elasticized corset, no bones or laces just a zip up the back. It not only held my stomach in but pulled me in at the sides so that when I put the dress over it I had what they termed, the beginnings of an hour glass figure, which apparently was good. What was not so good was the constriction, Ruby's answer to that was 'Go on a diet and get some shape'. I was fully dressed at this point to make sure the corset looked right with the dress and did not show. I caught a look at my reflection in a full length mirror and had to admit to liking the outfit, but was horrified at the sight of Keane's head on top of a dress, it was just so odd and wrong. Ruby saw my expression and comforted me telling me I needed to see the full thing to really appreciate the look, she could see beyond the mixed look, and I should trust her. I told her I did. Soon we were back at the salon having stopped for some costume jewelry on the way. A couple of big rings, a long string of white beads, ear rings and two chunky bracelets for my wrists. Finally I could go home, as I gathered up all my bags she brought out a small bottle, sprayed it on my wrist and asked me smell it, when I said it was nice, she told me it was a gift from her. I looked at the label 'All Woman' was she trying to tell me something?
When I had everything home I was putting things away when April rang to see how I had got on with Ruby, fine I said, all ready for the next show. April told me he wanted me to be there Friday and Saturday, and that I should get some practice in on the shoes and gestures. I told him I was already wearing the heels which got a 'good girl' from the other end of the phone. There it was again, I was being called a girl, April clearly thinks of me as female, I was not sure I wanted to think of myself in that way, but I did think that maybe I should stop thinking of April as a man and treat her as the woman he so often presented as.
Thursday fortunately was a busy day and thankfully kept my mind occupied or else the anticipation of Friday might have been too much. I did wear the heels once more in the evening, and then as Ruby advised I had a makeup session, then as I had not done it before I fitted the wig myself. By the end I had everything on and took the opportunity to pose in front of a long mirror and consider just how I looked, then spent some time walking around to familiarize myself with the costume. A quite unusual way to spend an evening I had to admit as I cleaned everything off.
Friday I got myself dressed in the underwear before going to the bar, the dress, shoes etc were carefully packed in a small case. I got to the bar about six and found April in the bar with Jason. She was dressed in what I would call a slutty style, might not be my choice but it certainly got Jason's approval. After saying hello to them and a few others I went into the back to get ready, I hoped to be able to do it all myself without April's help. When she came in I was gluing the nails on, she smiled her approval, then settled down to sorting herself out. This time a long flowing red gown was her choice. This week I knew a bit more about what was expected of me, I sang a few songs when it was quiet, and went into the crowd to encourage fresh singers to have a go. I was more relaxed with the chat and was able to play April's stooge for some of her jokes with more ease.
Saturday was a rerun of Friday evening, I had worn my softest shirt all day just so I could enjoy it against my smooth skin. I was nearly ready when April appeared in the changing room, this time she was not the usual sexy look I had seen recently, but even in jeans and shirt she looked more female than male. And the transformation was even starker as she turned herself into a gorgeous drag queen. While I was doing my face she suggested some shadow below my eyes, and if I could get one, a lip liner to define the edges better. I did my eyes bolder and had to agree it looked good. We had a good night, I sang a few tunes, April compered and a rather blue comedian was the star guest who made the most of having two drag queens to joke with. At the close I had really enjoyed myself, and when Pete came in to tell me how good it had been it was the icing on the cake. 'So you enjoyed yourself?' I could only smile back 'Good because if you leave for any reason I will want my money back for Ruby's little spending spree' this was a bit of a shock back to reality. 'Good job I like it then isn't it' I replied 'Good girl' Pete said and gave me a pat on my bum. As we cleaned up April was giving me a few tips on how to handle the men when I am flirting in the crowd, and told me to have a good week. I had a drink with the bar staff before leaving and found myself easily making friends with these girls and boys who covered every aspect of humanity it seemed, creed, color and sexuality seeming to be no barrier to them, I was surprising myself as to how easily I was fitting in with these people I would never have mixed with before.
The week was rather dull after the weekend, I worked, I did my grooming, I did some training with the heels, they had been uncomfortable by Saturday night and I needed to break them in, so I wore them whenever I was home, I also wore the girdle and corset so I could get familiar with the grip of these items. But what I would pick out of that week was the websites I visited about divas, cross dressing and drag queens, Divas were amazing, cross dressing was just weird, drag queens were outrageous. But somewhere in a mix of those three was me, and I did wonder where it was taking me.
Friday I turned up to the bar with an extra lip liner which got approval from April who showed me how to use it. We had another good night. Saturday and Sean the stripper was back, but the event that was memorable for the wrong reasons was being accosted by a drunken man who thought my flirting was for real, but almost as soon as he made to cuddle me, he was picked up by a bouncer who swiftly showed him where the door was. I said I was not bothered but went to check my make up for damage after his clumsy kiss, what I really wanted was time for my heart to slow down and my nerves to stop jingling. A few minutes later Sean came in and asked how I was, I said fine, then he gave me a gentle hug and tenderly kissed my cheek. I thanked him and spent a moment alone. Odd I thought, if Keane had been accosted no one would have bothered, but as Kiki I had reacted differently and people had appeared to care for how I was. Maybe being Kiki had unexpected benefits. April did give me her tips on drunken men once again, but this time I listened.
I could write about how every evening went, I was enjoying myself, getting paid well and singing some great songs, and getting more confident with the banter between April and myself and handling the audience. But for the next three weeks I was just getting used to the routine and how to improve my part in the show. By the third week I mentioned to April I had a set of false lashes and she told me to bring them in on the next Friday as it is not worth putting them on for one night. So the next week I turned up with them and April showed me how to fit them, and I had to admit they were an essential to a drag queen look, April agreed and explained how she would wear them for a few days at a time as she hated the pain of removing them. Leaving them on Friday night did mean I was not going out in the day on Saturday, and wore a cap with the peak down when I left the flat in the afternoon.
During the next week I had to call at Ruby's for more lashes and extra nails, she pulled me to a quiet corner and asked how it was going, I said it was good, she said she could tell, then asked if I wanted to improve my look, when I asked what she meant she suggested a list of things she could offer. I turned down the more extreme like acrylic nails which would make weekday working difficult, but I did come away with two studs in my ears, well boys do wear them so why not. What I was less sure about was having my eye brows plucked 'to tidy them up' Ruby said, and it did change my face but not dramatically so I was OK with that.
Everyone noticed the studs, but only April and Janet noticed the brows, Janet actually running a finger along one saying how nice it looked. But more of a treat for myself, while I was getting some fresh tights and a spare pair of control pants, I picked up a lacy bra and pant set, maybe I was feeling nervous about buying women's items, or just buzzed after the things Ruby had done to me, but I could not wait to get home and try them on, then spent the rest of the day wandering about the flat in my pretty new clothes.
But the Saturdays were becoming a little dull, because of the lashes I was staying in through the day, and after a week I realized I might as well leave the nails on as well, by the end of three weeks I was just changing my dress and shoes to go home so I could clean off in comfort. This was fine coming home in the dark, but leaving on a Saturday afternoon was more troubling, what if I bumped into someone I knew, I had my story about being a drag queen ready but not sure it was a terribly good one given the image of some drag artists. My friends had kept in touch, but working Friday and Saturday night meant I only meet up with a few of them mid week which seemed to always involve Janet and Dan, and Janet in particular was curious about how my new job was going, I would always tell her it was fun and enjoyable, I even allowed them to come and watch as I got more comfortable with the image I portrayed and the attention I was getting.
After six weeks of hiding on a Saturday Janet called round unexpectedly, I had left the door on the latch after going to the waste chute, so she walked in on me as I was sat putting a coat of burgundy polish on my long nails, and wrapped in a dressing gown, admittedly toweling, but a robe none the less. She let out a wow and shut the door, then noticed the bulge beneath the robe and caught a glimpse of the lace cup of the bra cradling the silicone fillers. Janet was clearly excited by having discovered why I hid on Saturdays. 'Right well I think it is time you found a way of getting out on Saturday, if you can’t go out as a man, why not go out as Kiki' I was going to protest but she was out of the door and back twenty minutes later with a bag of her clothes. She picked out a loose top and a plain stretchy skirt for me to try on. She approved and told me to put my heels on, she was going to take me for some retail therapy. I had been earning good money and she wanted to help me spend some of it.
We started in a shoe store and came away with a pair of 3" black courts and tan moccasins. So now in the lower courts we went to the fashion outlets, I hoped I would be able to do as Ruby had done and take things home to try on, but Janet said that was too much effort and pushed me to go into the changing cubicles. We came away with three outfits, Janet described them as a lounging at home, which was a neat t shirt and soft flared skirt in creams and browns, then a going out dress, russet colored with a big belt pulling the waist in, and a clubbing set of gold crop top and leopard print mini which I doubted I would ever find an opportunity to wear.
It was getting late in the afternoon when we got back to the flat, so I only had time to pick up my costume case and at Janet's insistence I changed into the russet dress. She then drove me to work promising to come and watch me later. I walked in for the first time wearing a dress, Jenny was the first to notice as she walked past, and stopping to give me a hug, asked me why it had taken so long for me to come to work in a dress rather than the awkward boy look I had been persisting with. Dave at the bar told me Pete and April were in the office, and wishing to show off I went that way and knocked on the door. As I opened it, Pete saw me and smiled 'You look good, come in' I stepped in and let them see the new dress, 'You are liking the job I take it' 'Yes' I replied. 'Good because I have something to ask you. April is going into hospital in a few weeks' they gave each other a quick smile 'And I, we want to know if you will stand in for her till she is back' I stuttered something. Pete continued 'Off course I will pay you what April gets' then April cut in 'And she will need some new outfits, that gold one must be threadbare by now. Time you dipped in your pockets' Pete was laughing 'Get out, you pair of queens will ruin me, I don't have bottomless pockets' then he laughed again 'OK Kiki a few hundred to get yourself a bit of variety if you will do Wednesday to Saturday' I turned and smiled 'That might just be enough' April hugged me as she said 'Good girl, don't let him get off cheaply'
Changing was much easier as I only had to change my dress and shoes, then use some bolder colours on my face and brush out my hair to give it more body. As I was changing April suggested I compere that evening, she would dress down and be ready to step in if I needed help, but it was to be me if possible. I was shocked, talk about being thrown in the deep end. I was still taking this idea in while April changed into a plain black dress which meant I was going to on my own. Sean was back on as the stripper so I knew that would go well, and there was a past karaoke winner who had promised to come along, plus my songs and some banter with the audience. Janet was in the crowd and would give me a supporting smile when I looked at her. Dan turned up during the stripper set and he got a good look of the show we put on which had become even more close to the knuckle, and over the several times we had done it I had got to enjoy it even more as we got more provocative towards one another. Dan was able to tease me mercilessly later given my usual staid image he was used to. I was exhausted at the close and could not wait to sit down and have a quiet drink. Sean gave me one of his tender kisses as he told me it had gone well, April came to give me her thanks, and Pete came in with my money, which when I checked it was my normal pay plus a bit more, and a few hundred extra which must have been for my clothes. I was thrilled to have so much, I had never had that much in one pay. I was enjoying my job and success seemed to be right there in my hand, if money is a judge of success?
That Sunday was a new experience for me, I had money to buy dresses and needed to work out what sort of dress style I was looking for rather than just picking anything that fits and is maybe a nice color, which is basically all I would do when buying men's clothing. This time I spent time looking through websites on fashion and style, the drag queen sites were useful too, but then I would be put off by the prices and ended up looking at auction sites, and then considered second hand shops, but that was a bit more daunting as I did not want the conversation 'Hello my name is Keane, I want a pretty dress' I imagined a frosty response. I also had a few weeks to sort myself out so I did not have to panic. Although I did bid on a nice bridesmaids dress, strong pink, fuchsia I think it was called, puff sleeves big skirt, it would be loud enough for the drag style. I gave myself a week to get at least two dresses which would give me three all together, I would also need shoes but hoped my gold and black ones might cover any dress color I got.
I now had three weeks to work at the computers, I let them know I would not be available for big jobs on the Thursdays and Fridays in a few weeks, I told them I was helping out a friend, and that I was not leaving and still wanted to work, just have a few days off for a bit, which seemed fine as they did not do holiday pay. Tuesday I won my first dress, who would wear it I could only guess, canary yellow, fitted chest, sleeveless, big layer skirt. I thought it outlandish enough for the show, white beads etc and white shoes I had one outfit.
Thursday, Janet called asking if I wanted to go for a drink. She and Dan were very close it seemed, but Steve was there and had been given there version of what my second job was becoming, he asked some questions but tended to smile and say 'interesting' a lot. I told Janet about the dress as she was the only one I thought might be interested, her reaction was 'not a diva dress is it' and I had to admit it was more drag queen, but then I would be the host not the singer.
Friday I had no jobs so decided to have a totally girl day. I kept my satin nightie on till I had cleared up from breakfast which had become some cereal now. Then shower, shave, moisturize, get dressed in the top and skirt, fix the hair, do my face, nails. Then it was time to look for dresses. I spotted a wedding dress that I liked, white of course, round neck with short skirt, but what made it were the net skirts that allowed the legs to be seen through it, the big sleeves and to make it great, white feathers around the neck and along the edge of the wide sleeves. I would need to buy some white shoes for definite. So I plucked up all my courage and slipped the moccasins on and before I could change my mind walked out the door. I made straight for the shoe store and hoped no assistant came and offered me help. I found a pair that would be good if not comfortable, a platform sole and 5" heel with straps everywhere. I bought them. Then went looking for gold costume jewelry. Ear rings were big gold discs, four big bracelets, two chunky rings and a short big bead necklace. I had everything, I just hoped the yellow dress had turned up as it was supposed too.
That evening I went to work with my new outfit in the case having decided I did not need to change for the journey there. As I expected I was host while April would do the floor walking and hopefully banter with me to help the evening along. She loved the yellow dress, I apologized for it not being very diva, she said that was fine if I was going to be hosting. For the Saturday I asked if I should be in the yellow or gold dress, gold she suggested, you can be a diva for only a few more turns. As we changed and I put my skirt and top back on I gave her a hug as we said good bye, and it suddenly dawned on me we had been doing this hugging for weeks now and I never even thought about it, somehow it had just become a natural thing to do. I even stopped behind after closing to have a drink with the bar staff who were becoming quite good friends by then. Jenny was always nice and even nicer now I wore dresses to work, but then I think she is a lesbian. Marc who is a camp gay would like to take me to meet one of his friends who he says fancies me something rotten, I always tell him I am flattered but no thanks.
The white dress came on the following Tuesday and I loved it. But was lucky enough to spot in a thrift shop a purple gown, satin I think, it fitted everywhere from the buttoned sleeves, and fitted right down to the long skirt with its short train. It was a diva dress, but it had a low neckline so went to see Ruby, who had become my friendly advice stop. It was she who had suggested a strapless bra for the white dress and now suggested some fine netting across the front in a skin tone so it looks like an open neck with a necklace to hide the top edge. She even told me where to go for the material. Then with my school learned sewing skills I altered the neck to suit my needs. And with the gold accessories I reckoned I had outfit number four. I was ready for April's job.
I had a week left before April would be having her operation and I would be the host. The nerves would not get me till the week after when I was on my own. For the next two weekends I was doing the usual routine with April, except for the anticipation of giving my new outfits an airing in public. So for the Friday I went for the purple gown which April said was a stunner and set us up for a good karaoke evening. As before I was wearing female clothing to work, this time the russet dress. Then on the Saturday I wore the skirt and top in the day and to work, and then wore the white dress to perform. This one really got a good reaction of April, even a few of the staff commented. April did mention it was a mini dress with a transparent skirt that only makes it sexier. I had not realized this, but took it as a warning that drunken men might get the wrong idea as to what I was doing in the bar. This was also the evening a few of my friends turned up in the crowd, Janet and Dan were there every few weeks, but this time Steve, Phil, Mary, Alexis and Lisa were there. April saw Dan and persuaded him to sing a duet with me, another love song which made a couple of the friends question our relationship. That is according to Janet who heard the comments. Maybe we were too convincing at portraying the song. Whatever, Dan did not seem to mind the reaction and gave me a kiss as he left the stage, and knew I would be a man the next day if we meet. So that was a surprise. Another surprise was to come out of the changing room, having my usual hug with April, a nice peek on the cheek of Jason, and money with a squeeze on my arse off Pete. Then finding my friends still in the bar waiting for me, this was a bit awkward only Janet had a real idea how often I wore a dress away from the bar, Dan had seen me once, the rest might have no idea. This could be a shock for them, Janet came to me and hugged me 'You were good tonight' then Dan spoke up 'That dress is a bit special' I replied with a thank you. Then the others seemed to relax and invited me to sit with them, I asked Marc to give us a drink, he made some attempt at saying the bar was closed, so I just asked for bottles so I could clear up, and he gave in. After a short chat we drank up and got out of Marc's way. As we wandered down the street to get a taxi I felt they had accepted my explanation that it was easier to get ready at home and travel in a dress than do the full change in the back room at the bar. It was Steve, my oldest friend who walked along side me and asked if there was not something more to my wearing dress off the stage and when I said no, it is just an extension of the job, he expressed his disappointment and told me I really did look very good in the dress I was wearing at the time, and a real doll in the white dress I had worn on stage. I did not quite know how to react to that, was he being sincere, he might be, but was he in some way chatting me up as a woman, that idea was a new one to me. Did men really fancy Kiki even though they know I am a man? I thanked him for the compliment and fortunately came to the taxis right then and the group reformed. Two taxis back to our area of apartments, we all stood on the pavement chatting for a few minutes, then for no reason I could think of I invited them all back for a coffee, Phil and Mary left us there but the rest came up. They must have wondered what they had walked into, my other three drag dresses were hung up and there were cosmetics on the kitchen table. I quickly cleared things away and Janet made the coffee while everyone found a seat. Alexis and Lisa took an interest in the dresses and told me the purple one must be divine to wear, I agreed it was very nice if a little tedious to get into, they might even have been a little jealous that I got to wear the style of dress they only wear for special occasions, but I do it regularly.
One by one they left until Janet was the only one left, she helped clean up, but instead of leaving slid an arm around my waist and gave me a French kiss 'Now I was wondering what you look like in one of the satin nightgowns we bought the other week?' 'You really want to see?' I replied by which time she was releasing the belt on the dress and pulling the zip down 'Well if you insist' I added. 'I do' she insisted. We had a very nice night together, I lent her one of the others and for the first time made love looking like a woman, which with all that satin about was very enjoyable indeed.
Morning came eventually and I took her a coffee to wake her up. We sat in our night wear silently, then she stunned me 'Steve fancies you' 'What?' 'And I reckon Dan does as well, he keeps saying how good you are at the bar, and that singing was perfect' 'What?' I was getting a bit too much information. She went on to explain how Steve's body language the previous night had been that of a man chasing a girl, as for Dan she had stopped over at his place the week before and he kept mentioning me, which did not go down well with Janet who she thought was getting something going with him and not just casual sex. I retold her I was not gay, and she said she knew I was a functioning man, but if I ever did fancy seeing how the other half lived then either of them might just like to treat me as a woman. I got out of it by saying I would be very busy with computers and doing four nights at the bar from the next week. Although the seed had been sown and I knew that sometime it would pop up and want to have its day.
Life as Keane returned once Janet had left and I had time to clean up and get myself looking male. This was followed by an awkward situation. When I went out for some groceries a neighbour who I was on nodding terms, told me I had a good looking girlfriend, I thought he meant Janet, but as I thought about it he was not meaning her, but the person he had seen was me going to work on Saturday. This worried me at first but then recognized that he had seen Kiki but not realized it was me, he had seen a girl and not a boy dressed up, the implications of this was to relax my attitude to going out as Kiki as I clearly, at least to this man, saw me as a girl when in a dress.
I had a busy week, two good days on computers, and then I went to the bar to watch what April did on the evening. It looked like a relaxed karaoke night with plenty of CDs being played as the bar was not that full. I had work on Thursday followed by being invited to meet Steve in a coffee shop. I was nervous of meeting him after what Janet had said. I was in shirt and jeans so maybe he would not be so taken with the idea of chatting me up. The friendship is a long one that has seen us comfort each other in some hard times like bereavements, so we chatted easily, but what he was most interested in was my life as Kiki, even as Keane he was complimenting me on how good I looked as Kiki and how good I was at the bar, even though he knows it is an act I had got the female look off to a tee. So I plucked up courage to ask him about the other night and his reaction to me. I asked if he was fancying his chances with me. He did not need to answer, he blushed, and said he had maybe drunk too much, but I asked again phrasing it differently and got a more definite yes. Then it dawned on me, Steve never had anything other than casual girlfriends. So as I was feeling that we were being particularly open about ourselves, asked him if he was gay. To which his answer was 'I can't be. It would kill my Dad' so he was, just denying it and locking it away. I felt so sorry for him and told him there are many gays that come to the club, he would be welcomed and how would his dad know unless he told him. I got another coffee and we sat in silence for a while then changed the subject to sport something Steve was keener on than me. We parted with a hug as friends can. I felt for him as I walked away and back to my night in a satin nightie, maybe I should have invited him home, but then I am not gay I reminded myself.
This was my last weekend with April, and we had a great time. Over the months we had become a quite competent pair, we could make comments on stage knowing the other would pick up on it and make it entertaining. She had taught me a lot about posing and gesturing and how the on stage performance is exaggerated but that off stage need not be that reserved. I also found out what the operation was going to do. She was going to have breast implants and some facial surgery on her nose and Adams apple. Wow was my reaction, bit drastic for the job I said rather clumsily. Not for the job, for Jason she informed me. And the rest I asked, in time she said, and then told me how she wanted to be as full a woman as possible without taking hormones, she did not like the idea of taking chemicals all the time, but surgery would be just as significant. She hugged me and told me to stay innocent, she had always fancied her own boobs, Jason was paying and suggested the other things, which must be something that comes from wanting to please your partner if you are happy to let them create in you their image of beauty. I told her to take it easy and that I was looking forward to her coming back and maybe letting me see what all the fuss is about. Don't worry about seeing things, her outfits would all be revealing she said quite emphatically, I just smiled at the thought.
After my two days repairing computers I decided that Wednesday would be a good day to get myself into a Kiki mood, after all I would be dressing for four nights so might as well spend the daytime in a skirt as well. First I did all the grooming things that a female image required, then made up and dressed in the top and skirt, decided I should maybe look for a few more daytime clothes as well as fitting in a visit to Ruby's to replenish stocks and let her give my hair a check over. I looked through a few stores before buying a rather plain blouse, more like a shirt really except for the room it had to accommodate my chest. I had trouble because of the large bust I carried, this was down to April, Ruby and my ignorance at the start, but I know nothing other than the D cup, so had decided once I learnt about such things that for a drag queen, bigger is better. However for a mingling into a crowd look, smaller would be better right now. I was going to stay with the D cup though, they were somehow part of who I was by then. I also picked up a loose fitting dress with little shape other than the rear fastening tie which I expected to be a challenge to fasten. My last purchase was a pair of ankle boots, I had seen girls wearing these and rather liked the look of them so bought them purely for me. Now that was something I would never have predicted a few months ago, picking female clothes because I liked them.
Ruby was too busy for a good hair do, so I made an appointment for Friday, timed so I could go onto the bar after.
Later wearing my yellow dress I had a slow night with the karaoke, but I expected that. There was plenty of time to mix with regulars and spend time talking to the singers. By the end I was tired but content it had gone well.
Thursday, a quiet day, followed by a similar evening to the one before. But maybe I needed that to let me rest before Friday. I turned up at Ruby's in the russet dress because I could get out of it without taking it over my head. Ruby had seen me before in a dress, but for some reason she made a big fuss telling me how good I was looking. Then she sorted out my hair for me, without removing it she cleaned it and reset the style so curls were tighter and stood out more. I had the biggest hair ever. The little extra she did to the hair was to replace the kirby grips with threads that somehow stitched it too my short hair. Then she suggested as I was doing four nights for a few weeks why don't I go for something else, again she wanted to give me nails but I refused as I would be working as a man on Monday, but promised if that ever changed I would come for nails. She did get to pluck my eyebrows though, I had been keeping them neat but she wanted to give them more definition. I looked in the mirror at the results and was shocked, I accused her of defining my face as female. She brushed this off with a comment that no one will notice, and besides it is too late to go back now I was far to pretty for a macho man. It was then I decided I should leave before she did anything else to me I might regret. As I changed at the bar and did my make up using some new products Ruby had sold me, explaining I was now ready for stronger colours and glossier lips. I grudgingly admitted that the brows being higher made my face more attractive and the make up more in keeping with my image especially on stage. Then with my long purple dress on, I minced out into the bar about eight doing a very affected gesture of lifting the hem of the floor with exaggerated finger holds. It was a shock to see Steve there, in my possibly sexiest dress, big hair and redefined face I was not sure this was how I wanted him to see me after our last talk. I could not avoid him, so went over and said hello, air kissed and asked how he was. He was at a loose end and thought it would be nice to come and watch me and take my advice and see how he felt in a gay environment. I told him I hoped he enjoyed himself. The show went well, I got Steve to sing a couple of songs, but possibly the best thing was seeing one of the regulars, I had chatted with a few times and was clearly a sensitive and caring gay, and not predatory one. I asked him to have a chat with Steve hoping he might find some answers to his situation. He waited till I had finished and shared my car to get home. We went to his apartment for a coffee and chatted long into the night, he was telling me of what Claude had talked about, and relating it to himself. I had hugged him when his mother had died, but now I hugged him because he was struggling with himself. And maybe it was wearing female clothes but as we hugged I would gently kiss him as tears ran down his cheeks. This brought thoughts about my sexuality to my own mind. Eventually I got to my own bed and a satin nightdress.
I woke in the afternoon my make up a mess and hair in my face, I felt shocking. As memories returned I had not bothered to clean off and now make up was smeared everywhere. The hair now sewn to me was stuck to my face and needing a good brush. In time I was clean and tidy again but my mind was still on the kisses I had given the night before, they had felt natural but were the first time I had kissed a man, I had been kissed many times by men in greeting and sometimes like Sean when he was showing concern, and I had not felt revulsion at any time. I even considered the idea of going further with a man, but how far? I resolved to try kissing a man properly if the situation arose and the man was appealing. That last part could well be the hardest part to fulfill. I had my Friday night show to do and now only a few hours till I had to be at the bar, so got myself organized and ready for my third solo performance.
Friday night had no unexpected events, just a nice fun karaoke, but my hair had ended up flat, I made an appointment with Ruby to find out how to deal with the hair when it was fixed. She also did my make up for me, so I turned up on stage in the white dress feeling great. The feeling great somehow made the show better and everyone I felt had a good night.
The next night however was full of unexpected events. I was ready for seeing Janet, Dan and Steve in the bar and was able to have a good time as well as entertaining the audience. A gay comedian was the guest and was a big hit with his own look on the world, I even enjoyed the fun he poked at me and my ambiguous image asking such things as how I look so good without a boyfriend snapping me up. He did two sets for me and did not rush off at the end coming through to the changing room while I was changing into the new dress and struggling with the bow at the back. He offered to help and tied the bow for me, then let his fingers linger on my back. 'I was not joking out there, how do you not have a boyfriend?' my mouth went dry as he pulled the hair back and kissed my neck from behind. 'Sorry' I said, 'Kiki' he said 'You are one of the best performers and you manage to look stunning off stage as well, and if I can say it without offending. You are hot and if you wanted to come out with me for a bite to eat now I would love it.' 'My friends will be waiting in the bar' I said looking for an out. 'Fine they can join us, you ready?' I was so walked out to the bar with Ged, as we walked into the bar the three friends were waiting, but what they saw I think changed their view of me. Ged was very close by my side as he introduced himself and invited them to come for a curry with us, but what I missed immediately was that Dan was holding Janet's hand and there was an unknown man stood at Steve's side. Janet was the first to say she was ready for home and looked at Dan. Steve looked at me and I hoped he saw my eyes saying help me out here. 'What do you want to do Chris?' he said looking at the man. 'I'm easy' Ged cut in with 'So I have heard' Chris blushed. Ged took the initiative 'Right well that is four of us for an Indian, the one two streets down will still be open. Maybe see you some other time' he lent forward and kissed Janet on the cheek and as we all moved to the door whispered in my ear 'Glad you came, your friend is nervous isn't he?' I replied 'Bit steamrollered really, his first time I think, go easy on him' I replied, 'I shall, it is you I am after anyway' and placed his hand around my waist and guided me towards the door.
The four of us walked a few hundred yards to the intended restaurant Ged keeping a hand on me all the way. As we entered he did the speaking to the staff so we had a good table. The circular table meant I sat between Ged and Steve, which was good as I was dying to ask Steve about the man he was with, while the drinks order was being delivered I got a quiet word. Steve told me I had taken his advice and come along to find out if men were his thing really, no point just imagining, and while he was watching the show Chris came and chatted with him, he was good company, he had asked Chris to stay when it was closing to meet the star who he loved saying was his friend, and Chris stayed. This was all said in seconds as we were brought back into the four when Ged took hold of my hand, 'For tonight, you are mine, gorgeous. Steve can have you some other time' 'It's not like that, we are just very old friends, honestly' I defended. In hoping to avert a scene I moved closer to Ged, on reflection almost an act of submission, I did not want to make a fuss and this was an easy way calm it down.
Chris was nice, not pushy, just a really nice bloke, Steve was a little reserved, but Ged was not. The comedian enjoyed playing to his small audience but I was getting to like the attention, the touching, the way he took charge of ordering, refilling my wine glass as it emptied, and off course the compliments, could I ever tire of hearing someone telling me how good I looked. The meal over and the wine empty we paid and left, Ged taking my hand as we walked out into the night, Chris, I noticed had two hands on Steve's hips as he steered him onto the street. Where to now Ged asked. I suggested my car was round the corner and could give Steve a lift, but Ged had other plans, he spun me round and gave me proper kiss, full on breathing through the nose, tongues, the lot. When we broke he asked if he could come too. My small frame and his height meant I had to reach up to kiss his cheek and whisper in his ear 'Sorry, I'm tired and need some sleep. Maybe another time.' He squeezed my shoulders 'I shall hold you to that I don't let the pretty ones away that easily' and kissed me back. I turned to Steve 'Are you coming?' then to my surprise as I focused on him and not on Ged, he was right next to Chris, 'No, Chris wants to show me where he lives'. It took a moment to register before I realized Steve was going home with this man. 'Ring me in the morning or call round' I instructed ‘and be careful' and as I hugged him 'Be careful yourself' We parted there, Ged walked to my car and told me he was serious about taking me out properly and put his number into my bag. I was tired but knew this was going to open up a can of worms in my head.
Steve came round about midday to find me trying to unstitch the wig, so as we talked he carefully removed my hair. He was now a confirmed gay, his night with Chris had proved it to him. He told me how the occasional times he had been with women seemed forced compared to the night before. Chris had made him feel special and he had never had such wonderful sex, no girl had ever made him feel wanted, Chris made him feel wanted, made him feel as though they were both participating, not like his odd experience before when the girl just lay there letting him do his male thing. Before I could ask he was telling me that they were meeting up again later at an art gallery, then who knows. He asked me about Ged. I was by this time looking like Keane. I explained how I still fancied women, but after a sleepless night I was considering taking Ged up on his offer of a date. Steve in a reversal of attitude told me I should give it a go, it would be different for me, I would be the woman, he would take me out, let him chase and seduce me until I was ready to let him in for his reward. I asked if that was how he saw women, kind off he said. I told him I was thinking about it. After some lunch we hugged as mates and promised to be in touch.
I had done a week at the bar and though I was a drag artist it had not dragged at all. Added to all personal stuff and the stage fun, Pete was pleased with the way things were going and not only paid me for the four nights but put in some extra. I had earnt two weeks money in the one week, but I had to keep the day job going for when April returned, so till Wednesday I was Keane the repair man. Things did not go so well for me though, I was given a job that would last me last me two days, but the customer made the job hard telling me it was only worth a day’s time, then on Tuesday something broke which meant I would need a part and had to be back on Wednesday, which meant I was rushing to finish. I got it all done with time to spare but the customer gave me a hard time and told me he would be complaining to the company. I was just happy to be out of there and going to the bar that evening. Late afternoon I got a call from the manager asking me about the job I had done, he was not pleased with my extended hours or the upset customer. He was a regular and had never complained like this before, I could feel the conversation not going my way as I explained my version of events, and when I said coming in on Friday would be awkward I could tell he was not happy. So when I finished and said I would be free for work on Monday, rather ominously he said there was nothing lined up or likely to be next week. I did not ask if that was a way of telling me I was in the dog house and they controlled me so I should be thankful for the work, but I was sure I was not going to be repairing computers on Monday next.
So From that Wednesday till the Saturday I had another extended period in dresses, and as I was getting more confident in daytime I had no trouble meeting up with Steve for a coffee at midday as he took a break from his office. He was full of himself wanting to tell me all about Chris. They had been to the gallery on Sunday, then out for a meal on Tuesday and back to his place, Friday they were coming to the bar, and he hoped they spent at least some of the weekend together. I was pleased for him, I had never seen him so happy, and felt that as I was wearing a dress could easily show affection without attracting comments from other clientele in the coffee shop. Then later I had a call from Janet, had I seen Steve why was he so excitable, I denied knowledge reckoning it was up to Steve to tell her, then she asked what was going on with the comedian. I told her the truth, we had a meal and I went home, the truth, but missed out the way he had made me feel and the worms that were playing with my head since. She promised to call round on Saturday a for girls talk, whatever that was.
The shows went as well as they always did, I was clearly enjoying myself and this translated into the show. On Friday Steve was there with Chris and being very friendly in public, I was by this time used to seeing men being with men, but seeing Steve with another man's arm around his shoulder was not what I ever thought I would see. But they were happy and stayed behind for a drink and chat, I could see even more why he liked Chris, just as a person he was very nice. Then on the Saturday, Janet and Dan turned up with a few of the others from the group, some who had never seen me perform in drag. I had another fun night with an unusual choice of guest booking, a folk singer who sang and told stories. It was not until a little way into the set I recognized her as a very talented artist who could write a great song and tell funny tales. This made my job so easy, I hoped Pete would book her again.
Backtracking a bit, when Janet turned up on Saturday she wanted to find out as much as possible about Steve, this man Chris from the week before and whether Ged was as close as he looked when she saw him. I put off the topic by asking her to come shopping I wanted some tights and a new top to go with the brown skirt. She was keen to shop but did not give up on trying to get gossip out of me. Telling her to ask Steve, and saying 'no I have not seen Ged' did not seem to work. So I asked her about Dan, it turns out they have been spending a few nights together, but nothing serious, just company. I managed a knowing smile, which meant, so what are you not telling me. It was a successful shop as well, a cream silk top which is what I had gone for, as well as satin shiny, baby blue pinafore style dress, some big hoop ear rings and some jewelry to go with the dress.
Sunday I had a conversation with Steve to make sure he was still ok, I knew enough about gay relationships to know they are often short term and promiscuous, so was expecting Steve to be bumped any time soon. But that Sunday was significant because I usually get an e mail with at least Mondays work on if not the weeks. This Sunday I got an e mail with nothing, I rang to see if it was a mistake, it was not, there was no work for me that week. I was gutted, when I asked 'Next week?' I got the answer, who knows, maybe. Not the usual, 'Sure something will come in' I was used too. Had that customer screwed up my prospects with this business? I was not sure but I did not want to lose the work, but at the same time I was earning more than I ever did and having a great time as well. I could live without it for a few a weeks’ anyway. This did mean when I got up on Monday and decided what to do with my free day as I ate my small bowl of cereal in the long black nightie, I could consider all sorts of options, I had not had a day off in ages as Keane, but then I had never had a day to myself as Kiki.
Carefully thinking this through I considered what I wanted to do until Wednesday evening as Keane, and besides maybe going for a drink with my friends there was nothing I could think off. But as Kiki there were a few things I could do, the first was to ring Ruby and ask her if she could fit me in, the next was to consider how far I let her go. Decision made, she was quiet that morning, so before I could change my mind I drove over there in my new blue dress. I was greeted with a welcome that was all Ruby, excitedly she asked what the rush was, and why Monday, had I no work. I told her the story that for this and very likely the next week I was not working except at the bar, so I thought it might be interesting to try living fulltime as Kiki, no switching back and forth. Her eyes lit up 'I have just the thing, well more than one actually that will keep you from even thinking of being a dull boy, come this way my dear girl' I followed her to a corner of the salon I knew as the desk that women had their manicures, I took a deep breath knowing what was coming and hoping I did not need to be Keane any time soon. Acrylic nails at least double my normal nail length and longer than the glue on ones even, painted a nice burgundy with a silver line diagonally across them. Next she brought out her piercing trolley and without asking if I wanted one fired a red stoned stud into my nose, 'Very feminine don't you think' then asked me to lift up the hem of my dress 'This one is just for you really' as she pierced my navel and screwed a matching red cap to the end of the stud in my belly. With a smile on her face she led me into a back room, 'You have on those bra fillers we bought on?' 'Yes. Why?' 'Strip off your bra and I shall show you.' I did as told as she picked out some bottles. It was cold as she spread the gel on my chest then positioned the silicones on them. 'Put your bra back on and get dressed' then looking me straight in the eye 'Those will not come off and a bit of make up on the edges they can look natural. Now, should I keep the release solvent so you can't get them off?' She said with a grin. Next she asked me how my hair was, I said it was fine, but she checked it over and then told me it was getting past it's best, I had worn it for the best part of six months and maybe she could send it away to be reconditioned properly or I could just go with another style, either way I needed some hair so asked what she thought. A new style seemed the best and after a few experiments we decided on a long sleek curling in and onto my chest style, Jennifer Aniston it was called, I called it different and nice, Ruby called it sexy as she secured it with threads to my own hair, when I asked her about care, she told me to treat it like normal hair, wash it, condition it, brush it like I would my own. Well I would but my hair is the tight wiry curls that don’t brush well, but I let it go. Thinking she was through I got up to leave, 'Not finished yet young lady, I have a few treats for that lovely face of yours' 'Oh' I answered. She checked out the eye brows and tweezed out a few extras, then she applied some make up. When she was finished she informed me it was long lasting base coats, I could brighten up the eyes of an evening, but for daytime I need do nothing, and the lips would not lose their color no matter how hard they were kissed, but a little gloss might look good at night. When I pointed out I only wanted to be Kiki for a temporary trail time not permanently she laughed, 'This is all temporary, if you ever want permanent just let me know. Now I think we are done here. Time for you to go and not even think of being a boy'
While I had been allowing Ruby to fix me up she was making suggestions for things I should do. The first I did was to buy stockings and a suspender belt. My next stop was to be the theatre shop to see if they have any interesting stage costumes. There was a nice pink one with lots of sequins and plenty of frills, but it was bit big on me and when I saw the price decided it was out of my range. I then had a text from Steve asking how I was. Text back saying Kiki had been for a beauty session, he was interested by this and we arranged to meet when he finished work. I was outside his office block waiting for him, kissed as we meet and took his hand as we walked to a nearby pub. He first asked about the holding hands 'No problem having a girlfriend is there' 'Well no but I thought you weren't that keen'. We chatted about nothing in particular, eventually he asked what Ruby had done to me, so I played spot the changes. He did well spotting the nose stud, nails and hair, but needed to be told about the makeup, navel and tits. When I explained about the tits he suggested we go and get me a low cut top now I had something to show off, I said I was not sure, but he offered supper if we went to see if the stores were still open. Steve bought a black halter neck dress for me, asking me to wear it when we went out later for the meal. It was while I was changing and sorting out the makeup on my chest that I dropped my bag and everything fell out. Like a hawk he saw the paper with Ged’s number on it. Then he teased me that he would text him asking for a date. I asked him to be sensible but even in my own mind I was not convinced, I had gone to all this trouble to be Kiki, why not see what it is like to be a woman with a man. The rest of our time together was spent listening to Steve telling me how great Chris was. When I asked him about sex he was not very descriptive but he was clearly enjoying the intimacy that he felt. He even made it sound like something I should try out for myself. And then I got a text from Ged. I looked at Steve 'You sent that text didn't you?' Steve just smiled back 'So you going?' Before I could respond he had my phone in his hand and was texting back. Moments later he had set up a date for me the following evening. I played the offended victim in his match making, but he knew I would turn up because I wanted to find out for myself if men were on the menu for me as well. What I was not ready for was Steve's 'birds and the bees' talk about how the mechanics of sex works in my situation, so I knew what I needed to know to enjoy it, and how to keep myself protected.
My first night sleeping with the new me was interesting, my nightdress fitted properly for the first time, this addition also made sleeping on my front hard, but generally the chest, the longer nails, the more mobile hair all contrived to wake me up at regular intervals but no matter how disturbed my sleep was the one option not available to me was removing the new things so I could just get a good night. I eventually gave trying to sleep and got up, to see the new me showering with breasts, long hair and nails that I could do serious injury with. I did check my e mails with a little dread that there could be a computer repair job, but I was relieved to see nothing. Once up and dressed I felt I needed to at least buy a scrunchie to keep the hair off my face at night.
As I walked out of the block a neighbour stopped me and asked if Keane was about, I said that he was away for at least a week, I knew this man would have asked Keane to have a look at his laptop. After he thought about my answer he asked if I would pass on a message to him. He told me what I expected, that his laptop was not working. I suggested that I could have a look at it if he wanted. The look of relief on his face that someone might get it working before Keane returned. So on my way back I collected the laptop and filled my day getting it working and returning it to a happy neighbor, when he asked what he owed I asked what Keane would charge, and the cheeky bloke came out with a price that was lower than I would have charged, but not wishing to say that was low and jeopardize my cover I accepted his cash.
Janet somehow got hold of the information that I was going on a date. She gave me advice on what to wear and how to handle the situation. I was so nervous I was getting ready at five and trying to work out if Janet's choice of the halter neck dress was right. Eventually after I had tried each dress on I agreed, underneath I wore a black set of lace and for the first time wore stockings. At seven I was ready and waited for him to call me to say he was on the street. He was sat in his car when I saw him, so walked over and climbed into the passenger seat. I knew exactly how the evening might go with his first actions. He lent across to kiss me with a hand resting on my thigh. He flattered my new hair, then seeing the new nails picked up my fingers to get a better look, I did wonder how many of the alterations he would have noticed by the end of the evening. We parked near a smart Chinese restaurant and rather proprietarily he walked with an arm around my shoulders, He wanted to be close and be seen with me, but I also felt he was saying 'this girl is mine'.
We had a nice meal and some wine helped me relax, by the time we were ready to leave, I had run through the options of what happened next many times, from going home alone, right up to spending the night with this man and find out if I could enjoy gay sex. As we walked to the car he kept me close, then as we got to the car he gave me the first proper deep kiss, it was a dark corner of the car park and with no one about we kissed easily. After we had raised our heart rate with that kiss he opened the door for me. 'Time to go' he said 'where?' I asked. 'Mine if you want a coffee' I had my hand on his arm as I found myself saying 'coffee sounds nice'. Ten minutes later I am entering a whole new area of experience as well as walking into a man's house. I was in the mood to find out if Steve was right. Ged made a coffee while I looked through his CD collection, he came in with the cups and picked out a Sade disc, very mellow and relaxing. We sat together and returned to the kiss. Some while later he took my hand and told me to follow him. Once in the bedroom he told me to remove my dress, then in my underwear I undressed Ged. Never really having had a close look at a naked man before besides myself. He was so hairy and his erection was impressive. Then he lay me on the bed and put some gel into my hole, and returned to the affection he had shown before. My own penis was straining inside my lace pants, but he was ignoring it while encouraging me to massage his until he rolled me into a position that suited him and started to push it into my hole. Slowly at first, this was a strange sensation, but then it got stranger as he pushed further inside me. I could feel my muscles tightening as it began to hurt, Steve had told me about this and I tried to relax, Ged was pushing harder and as I winced with pain he would push a little further inside. Soon he was all inside, I could feel tears in the corners of my eyes and his penis straining my anus to its limits. But no matter how much it hurt I was sensing something inside me tingling, and there was also the situation that this man wanted me, had found me attractive and now wanted me as a woman in bed. Then as I doubted I could stand it any longer Ged tensed and came. After a few more strokes he stopped and lay beside me, a few minutes later he got up to clean himself, leaving me on the bed. He returned in a dressing gown, 'I have rung for a taxi, should be here in five minutes' several thoughts rushed into my mind. I had five to get dressed and ready for the taxi. what a b######d he just wanted a lay. Then I really felt used. I was out of his house before he could say another word, I was so disgusted with myself and him. The taxi took me home and I had to pay him to add insult to injury. I cried quietly once the door was shut on the world. Eventually I was ready for bed and finally fell asleep.
I woke in the morning feeling quite dirty and used. Texts from Steve and Janet asking how it had gone did nothing for me. If I had not got D cup breasts glued to my chest with no solvent, long hair I would need help unfixing and long finger nails, I reckon I could easily have dressed as Keane that morning. But even in underwear I looked feminine so I dressed in a skirt and top that accommodated my bust. Then settled down to cleaning the flat. While I was doing that I considered what I was doing pretending to be a woman. I spoke with Janet and at five Steve came round and gave me a sympathy hug, I think he felt responsible for me going on the date, but I told I could have said no at any time, but I didn't.
The results of my personal investigations were.
1. I have a job as a drag queen.
2. I like the job.
3. Changing at home is nicer than at the club, so dress to work.
4. I have never felt attractive before.
5. I do like the fabrics.
6. I enjoy the grooming.
7. Male clothes are so boring.
8. I don't have to be gay. Even if Steve thinks I should try it.
9. Ged treated me as a woman (badly I know) but I must come across as a woman for that to happen.
10. I have had 6 months of fun, why let one bad night stop the fun.
11. Being flattered is addictive.
12. I like looking female.
13. Male is just practical not fun.
I also took time to think about the image I wanted to portray on stage, there was April's drag queen look and there was the sexy diva look I seemed to have gone for in the past. I planned on having a look through April's costumes after the show that evening and seeing if I fancied trying anything different. But for that evening I planned on the gold dress as it was the first and possibly still my favorite.
Steve proved that not all men are pigs and was very kind to me that Wednesday evening, coming with me to the bar and making sure I was ok. He later meet up with Chris and from their body language I could tell things were good between them. I did not look through April's stuff but felt I would rather get home and rest. They could wait till another day.
On the Saturday I tried one of April's outfits, a red sequined bodice with Spanish style ruffled train and feather boa to finish off the OTT look. It was ok but I just did not feel it was quite me, and decided I would stick with my diva look unless someone suggested otherwise. I had now done two weeks as compere, the bar was as busy as ever, Pete even said takings were up. My pay was certainly up, in two weeks I had a month’s pay in my hand, plus costume money. I felt good about the situation once again.
Sunday Janet wanted to gossip and help me spend some money. She insisted I had a good figure now I had lost weight and made me buy a boob tube, I wanting to be more modest and bought some hipster trousers that hugged my groin far more revealingly than any skirt and once we were home realized I would need to do some strong concealing in the male genital department before going out in them. She was after what Steve's new friend was in his life, in the end I told her to ask him straight. So she texted him asking if he wanted to meet up, he said yes and I was told to get ready the two of us were going out. But we had time to strip me off and work out how to give me a clean flat front for the trousers. Keeping soft was hard when she touched me, in the end giving me a lovely blow. Once cleaned up we found out that with tape my penis could be taped back and the balls pushed inside. This was not comfortable but looked good, Janet even commenting that if I misbehaved she could make it even worse with just a few gentle strokes. And a bonus was being able to leave the girdle off and wear my more feminine knickers. We meet Steve in a nearby bar, by his side was Chris, it was a straight bar so no affection between them, we exchanged kisses and sat down with our drinks. Janet beat about the bush for a while then looking directly at Steve asked him if Chris was more than a friend. There was a quick look between the two of them, then Steve quietly said yes and confirmed that he and Chris were a couple. Janet did not seem at all shocked, rather she was happy as she squeezed both their hands and said she hoped they were happy. Apparently she had been suspicious of Steve for years but never quite knew. Then she turned to me and said that it was my turn to find someone special. I told her to leave me alone, after Ged I was not ready for anyone else. As we left Steve got a full view of my new outfit, bare shoulders, breasts bouncing in the tight top and no hint of my true gender in my trousers, he hugged me and informed me that if he wanted a girlfriend I would be at the top of the list with a body like mine, I just told him to behave, he knew the truth.
On Tuesday I was invited out by Steve and Chris to meet them for a drink in the evening, I wore trousers and a looser top but still felt feminine. The pair of them were sat at a table with another man who I had seen at the bar occasionally. It was Steve who welcomed me to the table, and as we drank we chatted, Marcus the friend was nice, but it was not until an hour into our time together they got up and left me with Marcus for a lengthy time, I recognized it as a set up, and asked Marcus if he knew about the set up, he denied any knowledge. He seemed genuine and sincere as well as being nice so I did not get all nasty when they returned, but still made Steve admit to getting me there with an ulterior motive. He later told me he wanted to show me not all men are like Ged, and I had to admit he was doing a good job.
I was now into my third week and relaxing into the routine of the performance, I had also been living as woman full time for two full weeks and was relaxing into the gestures and mannerisms of a woman. I had even grown used to the feel of soft fabrics against my skin and having a 3" heel beneath my foot all the time, and that had become the minimum! I was also used to being related to and referred to as a woman. So when on Friday night I saw Marcus in the crowd I was happy for him to continue the friendship from earlier in the week, I even asked if he fancied going on somewhere after I was finished. We had a nice hour chatting over a drink in a late bar. Steve got to hear of this by Saturday morning and was keen to know what was going on. He was round later to check out I was being straight with him when I said we were just having a drink. But come Sunday lunch I was sitting at a table with Steve, Chris and Marcus enjoying the food Chris had prepared. In private Steve and Chris were far more affectionate than I had seen them before and could sense the genuine care they had for one another. They also took care to set things up so I was next to Marcus whenever there was a chance. In the end while we were alone we asked each other if we should make their day and play the couple for them. They came back in with the coffees to find us sitting on a sofa, Marcus's arm across the back of the sofa and me leaning into his body. The look on Steve's face was worth the deception, but saw the joke as we sat up and started laughing. The only thing we did not plan for was that we would quite like the situation and when we left Chris's together exchanged phone numbers and promised to meet up in the week.
Sunday evening renewed the dread of being offered work from the agency, I don't know why I was still being blacklisted, but was relieved to be. I decided that I should celebrate my continuing womanhood on Monday by increasing my female wardrobe. I spent a nice day shopping, finally taking my bags home to try them on again and hang them up in my rapidly filling cupboards. I had several tops, a couple of skirts, but my favorites were a pale green suit with a just above the knee pleated skirt, short fitted jacket with three quarter sleeves, I found a nice silk blouse to go with it and some brown heels with a lovely 4" spike. I knew I could wear the suit to work or to go anywhere, but the item I bought on a whim was a pair of satin knee length shorts with ribbon bows at the hems.
Tuesday and Marcus had called asking me to meet him for a coffee in the afternoon. With nothing better to do I agreed and spent a nice time with him walking in a park and drinking coffee. Steve found out a day later and was over the moon. I wore the suit to work and found out how easy it was to change as opposed to dresses, skirts go down, jackets and shirt style blouses button up the front, why have I struggled with over the head or wriggling over the hips clothes for so long. Thursday I wore trousers to work which took the more observant among the staff by surprise, Jenny did ask if this was a return to the dull boy look, I assured her it was not. Marcus came and watched the show for a while, but was working early so did not stop. Why was I disappointed at this?
Saturday and quite a crowd of friends came to the bar, all the usual ones, but Chris was there with Marcus. As I saw them in the room I did wonder how much the wider group knew about Steve and Chris. By the end of the evening Steve's sexuality was out and he was able to be honest, if a little awkward with his friends. I was not that forthright about Marcus, after all we had only been for a walk up till then, and managed to keep the friends from thinking we were the couple that Steve and Chris were trying to create.
But we were slipping into that situation, when Marcus asked me if I would like to go and watch him play football on the Sunday afternoon, I found myself agreeing to it rather too easily, and even more surprisingly getting up on Sunday and looking forward to going out and watching his Sunday league team that I had never heard of play another team I had never heard of. I made a classic mistake of wanting to look good and forgetting that standing on a touch line is not a place for skirts, tights, heels and thin blouses. Trousers and a warm jacket would be needed if this became a regular event. Which I doubted as sport was not really of interest to me, and football was just 22 men kicking a ball about, but better than rugby where the idea seems to kill the opposition and cricket is to bore the other team to sleep, but they would have given me a chair and a cup of tea from time to time at cricket. Anyway the football was not that interesting except for the fact that I got to see men running about in sports kit and being quite frankly, men. I considered how different to these 22 men I really was, there were anatomical similarities but in every other way I was so different from their rough macho ways I found myself considering that maybe I was more girl than boy. The post match chat confirmed this, Marcus was keen to know if I had seen his good tackles or passes, he even had a strike at goal, he missed but that was not important, well I suppose it was, but the fact I was there to watch was important. He had someone to tell of his feats and skills, and from what I could make out from the other girlfriends I was not in a unique position. We went onto his house after for a meal and as before just found ourselves chatting. It was so natural, we had similar senses of humor, liked similar music, art, books, food, wine, the list seemed endless. The only thing we did not agree on was our sexuality, he liked boys which I did not look like, and I was not keen on them generally, but Marcus was proving to be an exception.
The next week I decided it was time to go and see how April was getting on. Jason had called in at the bar on occasion to keep us updated on her recovery, the last time he said she was up to visitors when I asked. I tried not to say 'You look a mess' but she was bruised about her face still and I could tell her chest hurt from the way she held herself. She was still positive that the physical changes would be worth the current pain, as we chatted I noticed how subservient to Jason she was, it was he who had made the decisions about size and shape of the changes. My knowledge of relationships with cross dressers was being clouded by dominant men, and made me certain that I would not be told what to do. April was full of compliments for how I was looking after the stage, she had heard stories of how I was doing, she had also heard tales of Ged and apologized for not being there to warn me about this man, I just told her I hoped he never got booked while I was there. And as all cross dressers seem to do, she was flattering about my look. Loved the new hair, nails, was impressed with the bare shoulders and was one of the few to comment on the nose stud. I was honest when explained how I was enjoying living full time.
Fortunately I was given no more work from the repair agency, maybe not chasing them to see if I was needed or had I made a bad name for myself with them. I need not have worried, a few jobs came in from friends and I was still getting plenty of money of Pete who seemed more than happy with what I was doing to entertain his customers. He even complimented me on my suit saying how smart and feminine I looked, a far cry from the bloke he had first meet all those months ago. Then he asked how my day job was going, I told him it seemed to be quiet at the moment, he was clearly fishing and suggested he might have something for me if I was interested, I had to say yes as April would want her job back soon and I would need more income. He told me he would see if an idea would work, and then I was off to meet Marcus for our late night drink and chat.
We did more than chat, I gave him a lift to his house and for the first time ever we kissed properly, not just an affectionate greeting peck. Hug, tongues, passion, everything a kiss should be. He asked me if I wanted to go in for a coffee but I declined, he said he understood and gave me a quick kiss then got out to go to his house alone. I almost gave in to temptation and followed him, but I remembered Ged and took my hand off the door handle. That night was a long one thinking that I might have done the wrong thing, then reconsidering his motives and deciding that if he truly is caring he will not run away at my rejection. The kiss had been great though, I could do that again.
Before I got another kiss I had a call from Pete to meet him, he had several contacts all of which used computers and he wanted to know how easy it would be to offer a repair service. I explained my limitations and how software and hardware are different, and how people specialized in different software. But felt it might be something we could work on, then out of the blue, to me anyway I asked if I would be doing it as Kiki are Keane, he said I could choose but from the way he answered I could tell he would prefer Kiki to be doing the job. Then he sat back in his chair and changed the subject. He had been offered a dress that he thought might be just right for me; I asked to have a look. He handed me a bag and suggested I go and try it on before giving him an answer. I did as any employee does, I did as told. In the bag was a lacy/loose knit white dress, long bell sleeves, fitted body, not much room in the skirt, at the bottom of the bag were a satin bra and thong. I changed into them and could not fault the fit, but maybe Pete's taste. He knocked before coming in, I told him it was a bit too revealing, he told me it would be a great stage costume, like a prize cow in a market ring I suggested. He was taken aback by this comment, he truly did not see me as a sex object, to him it was a costume. When I asked him what he saw he replied 'A bloke who makes a good looking woman, and is one of my star attractions as a drag artist' I kissed his cheek and promised to wear it on Saturday when Sean the stripper was due on. He smiled 'that would be great'
I wore his dress plus white heels and big white bead jewelry, against my dark skin the contrast was most effective, but even more noticeable was the effect of the lights on the satin underwear, they shone from beneath the dress. I was ever so glad I had prepared myself down below with tape and nothing was revealed. As always I had a good time on stage with Sean, he was as cheeky as ever and made comments about what I was hiding in the thong. He always managed to make me blush or look shocked at something he did, but that was our rapport and it went down well. Pete after told me the dress was made for me it was great. Then to cap it all a few friends were there including the close ones, Janet thought it brilliant, Steve loved it, Lisa thought I was flaunting myself, and Marcus asked if I would go home with him still wearing it. I said no. But when I had changed I did go back to Chris's with Steve and Marcus as he lived close. After a really nice time Marcus and I left, Steve looking as though he lived there from the way he tidied up and said good night on the door. Marcus offered to give me a lift home which I accepted. When he parked we kissed. As we parted he said he had better be going, shame I replied, I was going to ask you in for a coffee. He went all caring asking if I was sure, I kissed him again and asked him again. We were in the flat next and kissing like lovers. In a pause he asked what had happened to the coffee, I said it could wait, and massaged his groin, he agreed it could wait. He was so different to Ged, he made sure I was ready and comfortable, used lube and a condom, took his time and if I flinched stopped to make sure I was fine. But I was so enjoying this attention I did not want him to stop, my own equipment was taped away, but that did not matter I had no wish to use it. After what seemed like an age of love making he finally came inside me, and I loved the way that I felt used by this man so he could have his pleasure while treating me so tenderly. This I hoped was how all women felt towards their men, though I doubt in reality many men are this tender. After lying together we got up to clean ourselves. I slipped into a nightie, so sexy he said, stop if you want I said. And he did. That was one of my best nights, nights with women had also been great, but for Kiki it was brilliant. I made him breakfast in the morning, and then he had to go and get his football kit before the match, which I dutifully said I would be happy to go and watch. Dressed more appropriately I found myself watching him through different eyes, this was very unexpected, but nice.
Marcus needed an early night as he would be in work early on the Monday, so after a burger meal we separated and went to our own homes, but not before threatening him that I did not want him talking to Chris about our weekend, I really did not want Steve calling me to ask me about how the relationship was going. I suffered the usual dread of being offered work but none came so I happily let myself continue being female. With two days off I planned some shopping and a trip to Ruby's to get the hair professionally cleaned and refitted, and the nails filled and recoated. I walked in wearing my long shorts and boob tube hoping she would be impressed with my figure. She was, noticing the near perfect groin and bouncing chest as soon as I walked in. For some reason Ruby could get me to talk about my situation better than anyone else, she was not close but did know everything about my true identity. I told her about Marcus and about the new dress. The relationship with Marcus did not surprise her greatly, she said cross dressers are not all gay but the straight ones must wonder if they are and some are bound to experiment, so I was not unusual in any way. Her views on my stage outfits were more definite, she knew April liked the drag queen look which in a way sends up women, but in Ruby's eyes April can be quite manly at times, the voice especially can come out deeper than a listener might expect, which is good for the stage, but I had my high range voice which meant in Ruby's words, I need to tell people I am a man and even then she was sure some would not believe it. This revelation did nothing for my male ego, within a few days Marcus had made me feel like his girlfriend now Ruby is telling me I should be a woman on stage not a drag queen. Whatever happened I knew I would still want to dress as a woman so shopped for some warm clothes ready for the next time Marcus wanted me to watch him on the pitch.
During the next week I meet with Marcus once and nothing happened just a pleasant time together. But I did meet Steve who got the truth out of me as to how my weekend had gone, he seemed genuinely pleased that I had found out that not all gay men are predatory and suggested we all get together soon. I said maybe as my male ego was suffering terribly from these experiences, he made me promise to call him if I planned on doing anything silly like being a boy again. I laughed and told him he was taking me too seriously. That week also was the start of Pete's new business venture; a laptop was waiting for me at the bar with a note asking me to mend it. Friday night Marcus was there in the bar at the end and without being discrete made it clear to the staff that I now had a boyfriend, not that I minded at all. He came back to mine for the night and made love to me as carefully and passionately as the first time. Then after getting up late we called in on Chris and Steve, Marcus said he had kept his word but I knew Steve would have told Chris, so for effect I walked to the front door holding Marcus's hand. And once indoors got excited hugs like only gay men seem to be able to do, especially Steve who appeared to be getting camper by the week. A coffee there and off to the bar for me, Marcus promising to come down later, and with a very nice kiss parted.
I walked to the bar enjoying the rather nice shimmering grey silk dress I had bought, it was always a delight as it was so soft and sensuous on the skin as I never wore tights with it. But it was quite long and caressed my calves, the other bonus was the generous amount of fabric in the shirt meant I did not need to hide my male bits too effectively. Well, still enjoying what had been a good week, I walked into the bar, said hello to the staff I saw, and was surprised when Jenny followed me into the back. 'Saw you with that boy last night. You going out with him?' I stumbled over my words but managed to say he was just a friend. She then told me that I was so sexy, and the thought of what I was hiding under my female clothing was driving her mad. Next thing I know she has locked lips and is kissing me passionately. I became swept up in the passion and her desire. The room was not big, but large enough for two of us to move about in. Soon she has a hand up my skirt and is releasing my dick and encouraging it to grow. Without really knowing how it happened I was sitting on a chair with Jenny riding up and down on my erection. She came to a peak and tensed above me, I came as she was relaxing. There were then the after effects, she was apologetic, it was not meant to have gone that far, I apologized for not stopping her. I then thought of Marcus and felt guilty; I also knew Jenny had a girlfriend. We agreed to keep it quiet, but secretly I had enjoyed having my penis inside a moist vagina and did wonder if the sex with Marcus was comparable.
Being Saturday I wore the lace dress, and though I was a little tender did tape myself so I could wear the thong with confidence. After the show I went to change, but feeling quite randy, maybe the after effects of Jenny I decided to just change the dress and leave on the satin underwear. Marcus came back to mine for the night as we had planned, so when I had closed the door, I removed my dress and told him his wish had come true as I paraded around in the bra, thong and heels. We made love on the floor, with the thong I did not need to undress any further, and though uncomfortable my own penis was rendered inactive by the tape. I did however have my first orgasm with Marcus, which took me by surprise, not only because I had one but by the sensations I experienced. Marcus loved it as well because he said he did not like to be the only one to get there, it should be equal enjoyment, and seeing me climax was very satisfying to him.
I woke in a quandary, Marcus lay beside me, but Jenny had reawakened something in me, the straight man. With relief I saw it was raining and that would be a good enough excuse to not watch the football. Instead I spent my afternoon weighing up my options, did I want to be a man, to be a woman, have a boyfriend, to have a girlfriend. Any combination was possible it seemed. I rationalized it down to; I enjoy cross dressing and will probably be gutted when I have to return to being Keane. Marcus makes me feel special, wanted, his girlfriend, female. Jenny though I like her was just sex, very good sex, but she did not really care for my feelings, she just wanted to satisfy her desires. And then there was that climax I had with Marcus, I wanted to do that again.
Having no one other than April I could think who might understand my dilemma I went round to hers on the Monday, I wore the suit to show her I was able to dress conservatively. But when I walked in she told me I looked sexy, I had forgotten that I like women in suits, and why. So I silently agreed and tried to play a more modest role. She was looking better and hoped to be up to coming to work in a week’s time. Her face was still bruised and a little tender, but she was keen to show off her bust, still a little bruised, she showed me what the primary reason for the operation was. Two huge breasts that were showing above her half cup bra. I was speechless for a minute; I asked if they hurt, were they heavy (I knew mine were not light) was she happy with them. She was very happy with them and so was Jason who was growing impatient to handle what he had paid for. I even considered the idea of having it done to me as well, not for Marcus but for me. I moved the topic over to my sexuality and she came over all sisterly. She had been through similar times, she had dressed for a long time before performing, but as a boy had had girlfriends, and up until a year ago had been with a girl she knew who liked men in dresses and bondage. But Jason for her had made her a one man, woman. Jason made her feel special and she would do anything for him, including let him rearrange her features to his liking. I mentioned the breasts again; they are for him I asked, oh yes, she replied, she would have gone for a C cup without Jason. In that comment I recognized how special Jason was too her. I left confirmed in my mind that sex is just that, but if I did something just to please someone they would be special. Though I was still not sure I would have such huge breasts to please anyone. Her parting comment was that I should enjoy life as much as I can, be what I want to be, and go out for what I want. I was only just starting and still young, so plenty of time to play around before settling down to find out who I am. But she did advise me to stay as Kiki, I was far too good looking to throw it away to be a straight boy with a nice straight girlfriend and live a 'normal' life.
As if my weekend followed by the visit to April's had not given me enough food for thought, Janet and Dan decided to call round in the evening, 'To see how I was'. It was clear from their body language that they were now a definite couple, and when they asked about Marcus and I answered with a 'Don't know' they suggested I was mad, he was a lovely man from the little they had seen, and I said it was more to do with who I am, am I gay or straight. Janet made some comment about my equipment working fine, which got a sideways look off Dan, but was told it was ages ago and he knew about our past relationship. They did leave me with the thought that I should not consider it as gay/straight or male/female, I should just be me. And if that I like to dress up and I find the company of one man satisfying, then I should accept that is who I am and relax. Forget the labels, just be me.
The trouble was that Kiki might be down to a weekends only again when April returned. I had made enquiries with my agency but they were saying there was nothing, so it was a relief that Pete asked me to call round on an associate of his who was having computer problems. He told me to go as Kiki, which was fine with me; until he told me they were quite sexist and liked having pretty women doing work for them, which he said made it easier to charge a decent rate. I spent all Tuesday there and had no problems other than a man who kept coming to see if I fine. Turns out he was Pete's friend and was known for liking pretty girls, but he paid well and we were all happy. Me with the job, Pete with his percent, the customer with his dreams.
With all that settled, I was to be me, but this might be the last full week of me being Kiki, I treated myself to a session at Ruby's. I explained the situation and she did my hair and make up for me, and refilled the tops of the nails. She hoped not to see me too soon for a removal job, but accepted that it might happen. I wore my long purple dress for Wednesdays show, and in a way was happy to see Jenny turn up afterwards. I asked her to help me unfasten the dress knowing what might happen, and as I suspected, once I was in my underwear she asked if I fancied a bit of action. I did not have a chance to say no before her hand was inside my knickers. I suppose I could have resisted but she was very persuading and soon I was inside her and sharing an orgasm. When I tried to say that I did not want to do this again, she explained how it was only a bit of fun as she saw it, her girlfriend knew she was not the only partner, but knew she was her emotional rock. I said my life was not like that. Jenny turned it round and asked if I preferred poking her like a man or letting my boyfriend treat me like a girl and poke me. In a rather quick response, but with long lasting implications, I said I preferred being Marcus's woman and have him make love to me, not just sex. She smiled and said she thought so, but if I ever feel the need to exercise my manhood I should just give her a call. Still naked I kissed her and said 'Friends' 'Off course' she replied, and hugged me back. Once back in clothes I could not wait to text Marcus, I knew it was late but sent it anyway. It read 'Love you' he replied 'Thought you did. I love you too' I had never said that before and it made me feel very special to think someone loved me.
The next evening I turned up for work in my silk dress feeling fantastic. Pete called me in first, he could see an opportunity for setting up a repair business, and would I be interested. Off course I would, April was coming back and I needed work. Great he said, when April was back to being the main host he would get some leaflets printed and I could go out to the local businesses and drum up some custom. Another great opportunity to stay with the me I wanted to be. Then when I got to the changing room, I was greeted with a bunch of flowers. No one had ever sent me flowers, the card read, 'So all the nosy staff know that I love you. Marcus' I was overjoyed and put on the white dress in a dream. Marcus turned up later and offered to take me back to his place for the night, how could I say no.
That week I made myself sore letting Marcus make love to me, but I wanted to be his girlfriend, to be his woman. We also talked, he thought the job Pete was proposing sounded good, and a pretty woman will be remembered by customers he felt sure. He also meet April when she came into the bar. In private he commented on the size of her chest, I explained that they were so huge because that was how Jason had wanted them, Marcus said 'really' with raised eye brows. I went on to ask if he would ever want me to have surgery. He said, only if I wanted it, but there was a between the lines yes that I picked up. So I asked the question 'If I had implants, what size would he like me to have, the size I am now, smaller or bigger?' He told me stop teasing him, but I pressed him for an answer. He admitted my prosthetics looked good under clothes but naked not so good to touch, as for size he was happy with them as big as I wanted, though the bigger the better, as a nice cleavage is always attractive. I snuggled up and told him 'One day when we are settled he could help me choose a more permanent shape for my body' he said 'that might quite interesting.'
April was back a week later to do the Saturday show, her dress was stunning, basically it was a halter neck but the soft fabric, came from behind her neck flowed down to the waist leaving a wide V down to her navel and a good view of the newly enhanced chest, strategically place tape kept the nipples covered, the skirt was just soft flowing and split to the hips on both sides giving glimpses of her long legs. By the end of the evening I was feeling envious of her and feeling a little dowdy in my purple dress. Marcus recognized my envy and tried to console me with flattery and by the end of the night making love to me as only he could, I did felt better. But after that every time I saw April flashing her breasts I would be reminded of the idea that I too could have a pair of my own.
Six months later. April is back hosting fulltime, I am doing a couple of evenings with her, and our show is getting more risqué as we develop our routine. Steve had moved in with Chris a few months back and is so camp and clearly under Chris's spell. Janet and Dan split up and went back to casual relationships. I spent a few weeks leafleting businesses, Pete suggested the suit, when I asked why he just said, I would be remembered. So I allowed myself to play a sexist role to hopefully gain custom, and it worked. I gave up my flat to move closer to the bar and work. Marcus at the same time felt he needed a change and we moved in together. As we cleared my flat out I had a big sort out, which Marcus, Steve and Chris helped me with. Unsuspectingly they removed all my Keane clothes while I was doing something else, it was not until I was unpacking that I noticed they were missing, Marcus just emphasizing the fact that he had moved in with Kiki, and by giving me a ring to wear on my right third finger he did not expect to see a bloke about the place
.
A week later he took me for an appointment with the surgeon who had done April, so we could discuss what we might do to make me even more attractive. Primarily to Marcus I said, what do you think? Who said if he got any choice in this, would I mind having a bigger arse as well as boobs? Off course I wouldn't mind and four weeks later my body was 38, 28, 36. I needed new clothes but then isn't that part of being a woman, especially when I was wanting to show off my new body, skirts hugging my bum, tops that revealed some but not too much of the fleshy mounds on my chest. Marcus insisting with April's help that I get a new stage dress. I ended up with a body stocking with three feathers placed over the important parts, which for most of the time would be hidden under long feather edged coat style of dress. I felt almost naked but nothing was too visible and went down a storm with Sean the stripper, as I used big feather fans to hide behind.
It was some months after I was having a quiet evening in on my own, sat painting my toe nails while wrapped in my silk kimono. I felt my nipple tingle as the silk carressed it, sitting back I fingered the nipple through the silk, it was so nice. It made me think back over the events and realised how much I had gained. I was happy and in love, but I also had a body I would never have wished for even two years before, and now sometimes I wanted nothing more than to make myself as attractive for Marcus as possible, which at first had meant permanent D breasts and a bigger bum, but more lately a smaller nose bigger lips. sometimes I do wonder just how far I would go to make myself perfect for him. Which is so subservient I hardly recognised myself in such thoughts.
The end.
Tiffany did this TV caption and I extended the story
This a picture of going to the leaver ball at the beginning of last month. That was after the last exams and was a significant day in my life for many reasons. Let me tell you a little about myself and how I came to look so pretty.
My name is Pete and live a few doors away from Kimberly or Kim for short. Our mum’s got on well so we would walk with one or the other to school as juniors, then at secondary we just carried on the tradition. We also played together as our mum’s shared the child care until we were old enough to play on our own and we just carried on being friends and played together into our teenage years. It did help that Kim was a tomboy and would play football with the boys, liked riding a bike and going swimming. Even into the sixth year we stayed friends, more just chilling out than running around doing sports.
There was an irony to Kim, she was this tomboy in jeans tee shirt and short hair, her mum was a mobile stylist who always looked ready for going out, never a hair out of place and make up perfect. There were a few times I walked in on the mother daughter argument ‘why do you want to look like a boy when you are so pretty?’ I was usually dragged out of the house by an angry friend who was just rebelling against her mum. Easy to see now.
Anyway enough background. The leavers ball, and me and Kim were sort of going as a pair, not a couple you realise, we never did anything like that. I was at home having my breakfast watching the TV, the mothers were in the kitchen having a coffee, I was summoned into their presence and went to find out what was so important.
‘Pete do you think Kim is going to wear a dress or even loose the jeans for the ball?’
‘Doubt it.’ I answered.
‘But she is so pretty, would you rather her look like a girl?’
‘This is Kim you are talking about, she is pretty but I can’t think how you would ever get her in a dress.’
‘Well Pete we have had this idea that might just shame her into letting Jill have a pretty daughter for one day at least.’
‘Oh’
‘Yes if we made you into a pretty woman and showed Kim that you can look good and it is not a problem for you then she might see there is no harm in looking her best.’
A pause while this sank in ‘let me get this right, I let you turn me into a girl, let Kim see me not making a big deal out of it, and hopefully she will see it is ok and wear a dress to the dance.’
‘That’s about it.’ Agreed the mum’s.
‘Just one problem, I might not look that good, oh and a second I might not want to do it.’
Jill answered the first ‘You have a nice face with good bone definition and a slim figure, not forgetting that lovely mop of hair on your head.’
Mum answered the second ‘And you are intrigued to know what you would look like, you have asked too many questions and taken too much interest in women’s style for me to be wrong.’ I stood in front of them and blushed at mum’s very true answer ‘Jill I think we have our answer, Pete will do it.’ They exchanged smiles ‘Now remember you have to make Kim think this is no big deal, anyone can do it attitude.’
‘Ok, but the dance is this evening.’
‘Don’t worry, I bought Kim a dress and you should know I have everything needed to style a woman.’
What followed was a most remarkable day, ok I was interested in the whole woman thing about how make up changed the way a face looked, how a dress style looked better on one person than another, but to experience it is a whole different thing.
While mum took me upstairs for a shower and to denude my body of hair, Jill went home and returned with everything she would need. I spent an age sat on a kitchen chair being pampered. My head was massaged with several products and rinsed even more times by Jill, mum applied soothing creams to my skin which also added some tan to my pale limbs. Mum did have to go out shopping when she realised I had a different size feet to everyone else leaving Jill to make up my face and do my nails. I don't know what I was thinking at the time but never thought beyond the moment really as Jill thinned my eyebrows, she offered supportive words like ‘not that many just enough to create the effect.’ And when she did my nails adding a good 50% to their length reassured me with ‘lots of customers have them just for a special occasion, worth it just for the whole look though.’
When mum came back I knew Jill had done quite a transformation even though there was no mirror for me to see, I could see in her face and in her comments that everything was going to plan, I was looking pretty, which for an eighteen year old lad was not the most overwhelming endorsement of my masculinity.
Sorry back to the story. I was sat in the kitchen drinking tea in a cream silk kimono dressing gown, my hair up in curlers under a cap connected to a drier, my face was covered in non male cosmetics, my nails were longer and sporting a pale pink gloss finish which matched my toes. Mum poured herself a cup and opened the shoe box she had returned with, I did not need say a word my face told them I was shocked, she had bought skyscraper heels for me, her reassuring words ‘you are young and fit, these will be no problem to stand in, we only want you to look the part not walk into town in them.’ They both laughed as my face relaxed.
It was not long till lunch but Jill wanted to get a few more things done. She felt my hair was right for styling and removed the curlers and set about it with a scissors, hand blow drier, brush and spray until she was happy with the result. I was less than happy with the amount of hair on the floor but I had agreed and it was a bit late to start saying I wanted out. I have to say my whole head felt very different as I ate my salad sandwich, the skin was slightly greasy, my lips tasted of lipstick like they should and my hair felt so stiff it might break, but the longer nails were the weirdest thing to get used to, they got in the way so often that the mums commented about how easy boys had it.
After lunch I was given some underwear to get into, the bra was awkward but fastening at the front then spinning it round worked but with no straps I was not too sure where it should sit. The satin knickers were a delight though making my organ which I felt made me male, reacted to this feminine luxury. I had been able to change in private but was embarrassed when I stood in front of my mum with in underwear with a semi on. She just ignored my condition and asked me to try the dress on. I stepped into it and pulled it up before she pulled the side zip up. It was tight on me or fits well as Jill put it.
‘Fill out the top and squash that thing down there, men are so obvious aren’t they Fay.’ Said Jill.
‘I have some control pants upstairs.’ Mum said as she left for her room, a supplementary question from the bedroom ‘stockings or tights?’
Jill’s reply ‘I think he would like stockings.’
Minutes later mum appears with two stockings over her arm and more underwear. ‘Out of the dress dear and let’s see if we can improve your figure.’
The pants did indeed squash my dick inside me, so much that when I felt the erotic sensations of a fine stocking caressing my leg as I rolled it up, the erection had nowhere to go. Back in the dress and socks pushed into the bra to fill it out I thought I was nearly done. But no, shoes to contend with as I wobbled about the room holding onto the furniture until I got the hang of standing on my toes.
‘He is looking fantastic Jill, you really can work miracles, let me go and find some jewellery to finish him off, or should I say her off’ she left the room giggling at her joke.
I soon had a chunky charm bracelet round one wrist and a watch on the other, the last shock was ‘Jill can you do his ears I don’t have any clip-ons and these long ones would look great with that hair.’
‘Oh easy enough dear, come here Peta.’
I thought who is pet-a, then it dawned on me, gave them an enquiring look hopefully saying ‘is this really necessary.’
‘Just finish you off perfectly.’ And after a couple of painful stabs in my ears I was adorned with ear rings that tickled my neck.
‘Right now then love remember what we said this morning, act as though this is not a big deal, if you can do it Kim can do it as well sort of thing.’
‘Got that.’
‘Ok you just go and make yourself comfortable in the living room while we wait for Kim to turn up.’
I went with a little more grace than I had when I first put the heels on and settled myself into a chair with a magazine I had picked up. I had always puzzled why women sit on the edge of seats with legs tucked under, well I found out the heels rather make your feet sit back into the chair and a tight dress is rather restricting, I actually found sitting on the edge more practical. I was also finding out how nice the fabrics were on my skin, the dress was a satin sort of material which was cool and soft, the stockings were just silky on my legs, the satin knickers were a delight, even the ear rings on my neck, the flicked back hair, the charm bracelet, the taste of lipstick all made me feel very different and wonder what Kim had against such nice things, ok the long nails, bodyform pants, throbbing earlobes and uncomfortable shoes were on the down side but surely just for a special occasion Kim could give it a go and see that she would look fantastic.
I had stopped my musings and opened the magazine, oh heck, one of Jill’s beauty journals, and that just had to be the time Kim walked in.
‘Oh my god Pete what have they done to you?’ she shrieked as she saw me.
‘Kind of wanted you to see if I can look pretty then you could as well. I mean I look kind of pretty like this, just imagine how good you would look.’
‘But you are sitting all prim and proper reading a glamour mag, you not only are made up like a girl you are behaving like one. I can’t believe you let them talk you into this.’ Then turning her attention from me she went to the kitchen ‘Mum you don’t get it do you, I am not like you, I don’t want to be a model, I don't want to attract some stud male, I just want to be me, and as for doing that to Pete, well words fail me.’
Her mum was first to respond ‘I just wanted you to see how pretty I could make someone, and then you could go to this dance looking fabulous, and you have to agree I am good at making people pretty.’
‘But why Pete, I know you can do things with your stuff, just why pick on Pete.’
It was my mum who had a word now, ‘He agreed to it.’
‘Pete, tell me you didn’t.’
‘I did.’ I hung my head and fiddled with the bracelet as I mumbled the answer, as I felt every ounce of self esteem drain out of me.
‘I always knew you were a bit gullible but this is beyond that, how naíve can you be to let them talk you into it.’
I tried to defend myself ‘Have you ever tried any of these clothes, they feel great and your mum’s head massage is lovely.’
She was staring straight at me ‘you will be telling me next you like dressing up like this and like walking in those heels. Tell you what get up and walk over there for me.’
Kim is a fearsome person when fired up so I walked over to our mothers. I did quite well hands out a little just for balance.
‘Bloody hell, you can even walk in those fuck me shoes.’
‘Kim enough of the language and Pete did this to show you it is no big deal to look pretty.’ Jill put her arm round my shoulder ‘and we have not done anything he objected to or forced him into, it really is not such a big deal is it Pete?’
‘Well I suppose not.’
Kim just glared at me ‘I thought you were my friend, you understood me, well if this is no big deal then you might as well have my ticket, I am not going.’
‘But we were going together.’
‘God you think I want to go after seeing you dressed like this, how my mother thinks I should look, no thank you. But if it is no big deal and you do have a spare ticket now, let me call someone.’
I just stared at her while her mum asked who she was calling.
‘Oh hi Sam.’ ‘Yes Kim here, just called to ask if you were going to this dance.’ ‘No I’m not, and wondered if you wanted a ticket.’ ‘Well yes I know you are gay and that was why you were not going’ ‘Yes but Sam listen to this, if you could take a girl who is really a boy.’ ‘Yes a long story but my mum has dressed up this friend for the dance and he has no one to go with.’ ‘No I am not winding you up, come and meet him/her yourself.’ ‘Yes you know where I live, well a couple of doors up.’ ‘Yes Pete’s house.’
I was trying to not get upset as the day was turning into quite an emotional one, but managed a ‘Kim what the hell have you done, Sam he is gay.’
‘Perfect hey, a nice big gay bloke with a sissy boyfriend partner who no one will guess is really a boy.’
‘Mum help me here.’
‘Not sure you need any help, besides perhaps where your tears are making the makeup run. Kim is right you never complained once, you do look very at ease in the dress and heels, I think you should at least give it a try. I mean how many girls have you been out with.’
I started to think of names to make it sound more than zero, but Kim shot in with ‘I will tell you none, I reckon he is as gay as me, just not admitted it yet.’
I was just about to defend myself and I could see mum looking at me with questions building when the door bell rang. Kim went to answer it.
‘Sam come in, you know my mum and Pete’s mum.’
‘Hi’ he smiled at them.
‘And this Sam is your date, pretty isn’t she?’
‘Pete?’
‘Sorry Sam this is not what it looks like.’
‘Yes it is’ cut in Kim ‘we have one gay lad without a date, and here we have one undecided sissy lad all dressed up as if he is looking for a date. Simple.’
Sam asked the next question ‘But why?’
‘They thought if I saw Pete looking pretty I would want to look ridiculous as well.’
Kim’s mum stepped in at that and ordered her out of the house, ‘Sorry Sam to have let her drag you into this.’
‘Not a problem Mrs Smith, just glad to have seen Pete looking this good, I would not have believed it unless I saw it.’
‘We called her Peta.’ My mum put in.
‘Well, Peta, you agreed to all this?’ I nodded ‘And you look great, does it feel ok.’ Another nod ‘And it is no big deal looking like this?’
I started to say ‘Well actually’
But mum talked over me ‘Peta it would be a shame to waste all this effort on making you look so good, and Sam here is wanting a date, so why not go.’
‘But mum!’
‘What! You look the part, no one will recognise you and if they do tell them you are Pete’s cousin or something, but go and experience something totally different, be Sam’s girlfriend, see the world from behind a new set of eyelashes as it were.’
‘Mum stop.’
‘Tell you what, me and Jill will make ourselves scarce and leave you two to chat.’
As soon as they had gone I apologised again, and he told me I looked great again. I made us a coffee each and answered his questions about what they had done to me and more cunningly, how I felt. As our coffees emptied I could sense myself being stared at and I was looking at my fingernails in my lap.
‘You are quite cute you know. I reckon we could have some fun tonight. Everyone thinks I am gay so turning up with a good looking girl will be great, and I reckon deep down you would like to stay in that dress and see what it is like to be seen as a girl.’
‘Sam I am not sure about any of this.’
‘Ok well I am sure you can do this, get Mrs Smith to do a few repairs and I shall be back at seven in a suit to escort my partner/boyfriend/girlfriend to the dance.’
He got up came past me and gently kissed my cheek, it felt like he had electrocuted me I got such a buzz from it.
Five minutes later mum is back ‘Well?’
‘I am going.’
‘Not quite the result we were expecting but an interesting one all the same. Now slip out of the dress and into the dressing gown we don't want in spoilt. Jill will do you make up again and I shall go and find a hand bag and wrap for you.’
Sam turned up and mum rang for a taxi. Besides the memories in my head Sam took a few pictures as well as the professional ones. The picture above is on the balcony above the dance floor at the venue. Quite a good shot really of the architecture, and of me.
Well that was the first day and I had quite a good time, a few shots before the dance and I was relaxed enough to enjoy myself.
But that was not the end of it. I woke up the next morning feeling rough, a shower, some food helped a little but seeing long pink nails at the ends of my fingers and a rather feminine hairstyle even without the styling, framing my still pierced ears and narrow eyebrows I did wonder what life would hold for me as Pete. I was discussing with mum what I could do when the answer came from a text message.
‘Peta. Mum wants to meet you. Taking us out to dinner. Posh 
Mum’s solution was simple at least for the short term, don't change anything be Peta for another day. She lent me a grey casual dress and showed me how to do make up and style my hair. I found her attitude towards me quite different, single mum and son is clearly not like mum and daughter.
Sam picked me up with his parents and took me out to a smart restaurant where I was on my best behaviour. His mum was nice if a little protective, his dad was charming but did not wear the trousers, she did.
At the end of the evening Sam’s mum looked me straight in the eye ‘Peta you are a perfectly charming girl and from what Sam tells me completely suitable for his erm preferences. Now like Sam I guess you have not found yourself a summer job, so I am going to offer you one as office junior at our warehousing business.’ I was about to say but I am not a girl when I was cut off, she was only pausing for breath ‘The job is only open to Peta, I am not asking Peter if you were thinking that. I also will understand if you need to get yourself some new clothes for such a job as the dress you have on would be inappropriate.’
‘Well er thank you Mrs Turner, I don't have job and I am not sure how much you know about me.’
‘Enough to know you made quite an impression on my son.’
Sam’s hand was on my thigh and squeezing. Flustered I stalled ‘I really should make sure with my mum before saying yes.’
‘I understand it is a big step for you to take.’
By the time I got home I felt I had been stitched up, our mum’s much have spoken by phone at some time because mum had a few extra bits of information, like the hourly rate and a clothing allowance was included. She told me I would never get such an opportunity, I asked if wearing heels and a skirt was such a great opportunity, but she countered with the point that I would be on good pay and Sam was nice boyfriend material.
Well as you can guess I took the job, filing, answering the phone, making the coffee, but also a crash course in how the female behaves and the effort taken to look pretty all the time.
By the time the results came out I had worn jeans only twice and had not dared go out as Pete for fear of being teased for the feminine alterations that had been made to my appearance. And after I got my results there was little point in hiding my female persona, I got terrible grades, no courses I wanted would take me, but Mrs Turner offered me a permanent position in the office. Mum said it would be foolish to turn down any job with my results and what with there being so many under 25s out of work. I checked with Mrs Turner that the job was for a female junior. ‘Yes Peta, now I am guessing you want to get off early and get ready, I hear Sam is going out to celebrate his results.’
And so instead of being a student at some university in baggy clothes I am Mrs Turner’s assistant and dressed like this.
Not quite the future I was expecting when I was sitting english, french and art exams only a few months ago. But one that is proving very agreeable with my mum, Mrs Turner and rather surprisingly, Sam my very nice boyfriend.
Lesley was convinced that as a woman she would never get promotion, and yet again she had been passed over for a less able man.
In the rest room later a girl friend suggested she should apply as a bloke, and see if it made any difference, it was said in fun and at the time she laughed. But when the job she wanted came up a couple of weeks later she was filling in the forms and realised how easy it would be to not be totally truthful about things like mr and mrs. Once completed she sat and stared at it trying to decide whether to change it, but thought she might as well leave it because she would not get the job as a female. All she had to do was get the references to play along, one was her friend, the other her immediate boss who had experienced such things herself, both agreed and with great trepidation she sent it off.
The next thing she has an interview, which she rarely got before, and her boss had been asked about this man working under her. Bottle out or turn up, the friend and boss point out they are all in this together now, they had lied for her so she had better turn up. She had a weekend to sort herself out, while Martin was out she tried on his suit, which was not too bad, shoes she had a pair that would do, no make up, but the hair was wrong and she did like it. A couple of phone calls did not alleviate the problem, the friends told her to get it cut, then Martin came back and caught her, she now had to explain what was going on. He just said fine but have your hair really short, there are some clippers somewhere. He found them and left her to make her mind up. But an hour later she was still sat on the bed when he returned, ‘how bad do you want the job, and to get at the bosses?’ He paused then plugged the clippers in, he knew she wanted it and motioned for her to go over to him. She sat down and shut her eyes and told him to not let her see the clippings. Ten minutes later she has a number 3, Martin tells her to get out of the suit ‘it is Saturday’ and gave her jeans and a sweatshirt, she cut her nails and bandaged her chest. ‘Right lets go shopping’ if she was to succeed she had to go out before the interview as a man, no good doing it on the day. Well things went fine, she spoke slowly and deeper than they really had before. He took her to the football where she watched the men rather than the football, then in a pub she was given a man’s glass, acceptance Martin said.
They spent Sunday doing more man type things, then on Monday she had the interview, full of terror that this was stupid and could loose her job and affect the others, but it was too late. Besides, she could do the job.
In the afternoon Martin got the call he dreaded, he had had the upset rejections so often, he was not sure how to take the ‘I got it’ call. She was over the moon. But by the time she had got home she had realised that they had employed her as a man, so how could she now go and tell them they were wrong and risk loosing the job. Martin pointed out how much she would be earning and she should go and buy herself a suit and get on with enjoying the job.
So on Tuesday she turned up for work in the suit, as she had a week to work at her old job. ?Fortunately nobody really saw her but she decided to go sick for the rest of the week, and start in the new job at the new site afresh.
The fun started the next Monday, Lesley went to her new job and quite happy with the clothes she had bought the week before, she spoke to Martin during the day to tell him things were fine, but she would be a little late, could he cook the tea. He often cooked but felt he would send up the situation and before cooking changed, he found her clothes and dressed as a woman, without much thought he got a dress that buttoned up the front for ease, tights, a pair of high heels, then a dip into make up to find red lipstick and green eye shadow he surrounded his eyes with, realising he had no tits he undressed and managed to get into a bra then put an orange in each cup and he was ready to greet her with a rush to the door and ‘how was your day at the office dear?’ and give her a lipstick kiss.
She was late but still excited by the job and the deception. The welcome she got made her laugh, as Martin teetered towards her in the ridiculous outfit, gave her a big red kiss and exaggerated hug.
‘Quite the housewife now I see’ she commented
‘well, we do have to keep or men happy don’t we’
‘Oh if that’s the case, come here my girl’ she then kissed him properly and fondled him as he would fondle her in a skirt, making it ride up.
‘Oh boxers, how romantic, not. What was wrong with those French knickers you bought for me?’
‘It was not serious you know’ he defended,
‘Just thought if you have me go about as a man, you should do it properly as well’ then smiled and kissed him to let him off the hook.
Some weeks later, she has settled into the new job and though wishing she could be honest, rather enjoyed the world as it now was, being a man at work suited her. Martin had allowed her to share his clothes and the boxer pile had increased to accommodate hers.
She decided to have a wardrobe clear out, it looked pretty much like the job would last, and with it her new identity, so she gathered all the old and unused clothes into a bin bag and put them out. Very soon she realised she had not worn a skirt or heels for months, and Martin asked her how she felt about being so butch, jokingly she replied, ‘What I really need is a good woman, people must think we are gay’
‘You are joking, I do love you remember, and it was me who encouraged you’
She tried to defused the tension in his voice, ‘I was joking, I know I have you, but I can’t help thinking what an odd couple we make, and how I would behave if I was dating a woman. I know I react to and others react differently to me with me looking like a man. Just a thought’ Martin went all quiet and thoughtful until Lesley started tickling him, but he was considering her words all the time.
The next day he was alone at home was Friday afternoon, he was really anxious about what he intended to do, but wanted to try it anyway, just to get it out of his system he said. He sorted through the bags of Lesley’s clothes that had not made it to the recycling bins, until he found a cream blouse and a denim skirt. Next he looked in the drawers for underwear and got undressed. The first thing he felt was how soft the pants were, then how awkward it is to fasten a bra behind, and tights are not socks are they. But the blouse was so soft and delicate, last the skirt. Now he looked at her dressing table, the make up was pushed into a drawer, but he found a lip stick and spread it around his lips, and brushed out his hair so it came more forward. He was just wandering what ever Lesley did for so long when she was doing her make up, when he heard the door close and Lesley call, the time had flown by and Lesley was early. Panic.
Too late,
‘hello dear, that is a nice blouse isn’t it?’
Martin changed from panic white to crimson blush in a second,
‘yes, oh I’m sorry, I was only, well,’ he started to stumble over words.
‘You were thinking about what I said about wanting a woman, and wanted to see if you could be that woman for me. How sweet. Love you’ she then gave him a hug and kiss.
‘Right’ she said,' taking a particularly bossy tone, ‘let’s do this right, strip off and start again’ she looked him over for any objections, ‘if you want, I would like to see what sort of a girl we can make of you?’
Martin looked a little unsure he was only mucking about, Lesley seemed to be taking it seriously. In his silence she took charge. ‘It’s only 4 o’clock, lets get you sorted and have a pizza delivered’
‘OK and if I look awful that’s it’
‘That’s it’, she agreed. Now she thought this has to be good, I had best go to town and do everything, and do it well
First she rubbed immac all over him, and shaved his bikini line, when asked if necessary she said yes it was, no explanation. Showered and talced, she led him to the bedroom with a towel turban and a towel dress. Next she found the silkiest bra and pants, filled the cups with tights, then thinking how Martin liked her to dress, she fastened a suspender belt, and showed him how to put on the stockings. He even commented on how much nicer they felt to the tights he had struggled with earlier. Now she got the hairdryer out and styled his hair from the pony tail he always wore, to a full of volume side parting, that swept across his face. Out came the make up next, plucked a few stray hairs from the eyebrows, and followed with a full foundation, powder, blusher, eyeliner, shadow, mascara and lipstick. All the colours being carefully chosen to create the face Martin would fancy on a woman, so they were quite bold.
‘Now what to wear?’ Martin was feeling quite sheepish by this time, ‘you like the blouse, and a skirt? Maybe trousers?’ he did not have a clue what would be a good choice but picked one of Lesley’s skirts that went with a suit, straight and to above the knee, and on Martin tight. She finished him off with a pair of low sandals, and a few bits of jewellery.
‘Now you can look in the mirror’ he stood in front of the image not speaking, the shock was complete. ‘So tell me’ she asked ‘do we have a woman in the house again?’
‘Bugger me, it certainly looks like it. How did you do this............ and what do you think’
They ordered their pizza, and sat down for a chat, and when the bell rang Lesley went to get the plates casually saying ‘You go and get the door’ as if Martin was dressed as Martin usually dressed. To both of their surprises, Martin collected some cash from the sideboard and went to the door, it was as he opened it he realised how embarrassing this could be, but he was there with the door open, the pizza was handed over, he paid, and said thank you. Lesley was right behind him as he closed the door. ‘That was brilliant, I do believe we are back to man and wife’ Martin was stunned by what he had just done, and did not take in her words, but as they ate he soon caught up. She called him Tina and planned their weekend around Tina’s learning.
Martin was always the tidier of the two, and would often cook and nearly always clear up, so he automatically cleared up after the meal, but then went on to make drinks for them, and cuddle up to Lesley on the sofa. The whole feminine role seemed so nice he relaxed into it very easily, as Lesley played a more masculine part.
Changes happened at bed time too, Lesley went up first whilst Tina was clearing up, and then washing the make up off. As she got undressed she saw the cotton pyjama bottoms Martin wore and tried them on and climbed into his side off the bed, leaving her satin pyjama’s on top of the bed clothes for him to see when he came in. without a word he removed the skirt and blouse, Lesley could feel herself getting aroused at the sight of him in the stockings, and when he put on the satin nightwear he commented how nice it felt and slid into bed, to find his wife taking a lead role in the lovemaking, not unusual but given the day, appropriate.
Next morning they sat and drank a coffee discussing how things might be. Lesley teased by saying that the side of the bed she had slept in was much more convenient for the boxer shorts drawer, and she had no need for the dressing table if he wanted it. Then she got up dressed in jeans and a T shirt which were his, over his boxers, and found a pair of his shoes and laced them up tight. The implications were not lost on Martin.
‘OK, I need to learn about make up, hair and dressing. If that can be done I will be Tina more often, would that make you happy?’
Lesley went over and kissed him long and hard, ‘I would love it, after last night and the pizza delivery I think it would be lovely, and very possible’ So they discussed and planned for the weekend.
Martin agreed to do some housework, and Lesley was to do the dirty car maintenance, and garden work. But not until Martin had been through his first make up and hair styling lesson. Which left him looking more Tina than Martin, so taking Lesley’s lead found a pair of her trousers, a ¾ top and sandals, which he wore over a very nice bra and pant set.
And so Saturday passed much as normal, just clothes and tasks reversed. Mid afternoon approached. Lesley sat with a drink, ‘How do you feel?’
‘Fine, nice to have clean hands and to see you do some work for a change’
‘Cheeky, anyway we still need to go shopping and what are we doing tonight there is nothing on the tele’
‘Well I have been thinking, if we went out of town, say the new Tesco, and for tonight how’s about going into Manchester’ it Martin was asking.
‘We need to go now, do you want to change?’ Lesley was completely taken aback by this turn of events.
‘Well maybe find a jacket and a purse’ Lesley snapped out of the stare that the answer had given her, regaining composure
‘The denim jacket is good, and here’s a purse, let’s have a wallet in exchange.’
And so they went shopping, Martin was nervous about meeting someone he knew, but was very watchful, and avoided looking at people. Lesley was equally unsure about being seen with him, but at times left to go and pick up some item from another aisle, and would stand and watch how people around responded to him, and besides looking nervous he attracted no comment at all, eventually she had to tell him to stop being nervous, no one was clocking him, and the store detectives will start following if he continues to be nervous. Martin tried to relax, and when they went into the cosmetics, he found himself engrossed, and then feeling conspicuous, as he smoothed foundation into his hand, Lesley told him it was an easy way to try out the shades, so gave it a go.
To be back in the car was a relief, for both of them, but they had had a buzz from being out.
‘Still want to go out tonight?’
‘Sure, and you?’
‘Where?’
‘I don’t mind a film, a club, a meal or just bars. You tell me I’m only the ‘wife’ after all, and the man makes the decisions!’
‘In that case I shall take my 'wife' somewhere special’
They had already chatted about what Martin thought a good looking girl looked like, which pretty much was as expected, a stereotype, so Lesley wanted to dress him in that style and take him to a few bars and see how things went. The smart look she really wanted could wait for another time.
Lesley decided they should wear clothes they had bought for each other in the past, Martin had never bought her anything sensible, whereas she would buy nice shirts for him. And so Martin surveyed his options, he had only ever bought sexy underwear, and a mini skirt, so he was limited, but he had liked the skirt, so agreed to try it. Underwear there was more choice, though it had to be with stockings with the mini, he had never bought her tights, but there was a choice of pants. In the end he chose some tight briefs, the thong he could not fit everything in and the French ones were too lose. So in a white undies set and stockings he slipped into the white flared mini. Lesley was ready way before him, and seemed pleased with her wife, ‘Just a top and some shoes, eh’ she had a rummage and found the sheer white blouse Martin liked her to wear as the bra was clearly visible through it. Next she found the 3” sandals, and advised on stronger make up colours. Finishing of with a load of bangles, a many stranded necklace, some rings and an anklet. Martin looking in the mirror approved of the result, but had reservations about the heels and whether the skirt would cover the stocking tops. Lesley just reminded him that he was dressed as he wished she had dressed before, so any idea of suggesting a lower hem, tights, or flatter shoes were dismissed from his mind. He did find a long coat to wear that recovered his modesty until he walked and realised it opened from waist and showed an awful lot of leg, but how could he argue?
Once he had walked about a bit and learnt how to walk and wiggle in heels, it was time to go out for something to eat, Lesley got the car and pulled up close to the door, making the distance from door to door a short as possible, and giving the prying eyes less opportunity.
In no time at all they were parking and Tina would have to walk down a street, in a skirt and heels. When it came to it there was no one about, and they were walking easily by the time they got to the bar they wanted to go in first. Lesley produced Martin’s wallet and ordered a beer and a gin, their usual, but gave Martin the gin, ‘Hope you like it, the lager shandy should be OK’. The evening went well, they had a bar meal, and visited a few bars, Lesley insisting on paying, she even used his credit card and forged his signature. She opened doors, showed affection in a male way, and was utterly male. Tina responded by trying to be convincingly feminine, which helped by the constant reminder of the heels that made him walk differently, a skirt that rode up, and stockings that slid down. By the time they had drunk enough, they called it a nightand went home. Lesley doing the hand on the knee position as she drove, then sliding it up to the stocking top.
‘Feels nice to me, even if I say so myself.’ She slid a little higher. ‘Seems you do as well.’ That night they were hardly in the door before they were making love. Sunday morning just had to be a lie in after the evening activities.
But the role reversal continued, Lesley got up for the papers and to make breakfast, and by midday they had got up and dressed, nothing special, just jeans and baggy jumpers, but not their own. The swapped roles hardly noticeable that day at all.
Then going back to work on Monday neither really thought about the implications of what they had done, rather reflected on the fun the weekend had been. But some things had changed, the sleeping arrangements remained reversed, and Lesley was being more dominant at home, while Martin would just fit in with her more easily.
And so it was Thursday evening sat in bed, Martin his satin pyjama’s, that they discussed the situation. Both wanted to see where this bit of fun might lead, Lesley to see how far she could go at being the man, and Martin wondered what he could get away with, or just for the sake of it.
A few months later, their roles within the home have changed radically. They both occupy the area the other used too, in chores, positions and clothes. Well at least underwear for Martin, he was not for going to work in a skirt, but there were a lot of nice panties not being used. They had a couple of week’s holiday booked, and they fancied a travelling trip, stopping in guest houses and looking around places. They choose the south coast and booked their first stop but left the rest open. They also decided they would see how it would be if they lived reversed for the two weeks.
So on the Friday they packed, Martin feeling most odd, not knowing what to take, and wanting to take everything because he did not have a clue what he would need, Lesley obviously found it easier.
Saturday they got up and Martin went for a casual travelling look of jeans and jumper, he did do his hair nice and a little make up, and his defence was they were in a hurry to get away. Lesley complained about the look, and wanted to know if he was serious about doing the wife thing or not.
Well they made good time and were booked into the hotel for early afternoon. Martin feeling a bit stung from the earlier criticism made an excuse to go off on his own, Lesley thought for a sulk, which was possibly true. But walking by the shops Martin passed some salons and after three offering walk in appointments, he thought I’ll show her, and entered.
‘Hello can I help you?’ immediately he felt panic, but he stood frozen for what seemed an age, eventually he managed to speak.
‘Could you do me now?’
‘Oh yes, depends what madam would like.’
Then from somewhere Martin did not know, he asked ‘I fancy a complete change of style’
‘Certainly come and let me show you some pictures’
‘No, I’ll let you choose, you will know what will suit best my shape’
‘If you are sure’
‘Yes sure as I will ever be’ and then seeing some one having acrylic nails applied said, ‘and I think my nails could do with a change as well’.
The girls then stood around and discussed his hair, and then started. They did explain what they were doing as they washed, then applied chemicals, and styled it, but all he could really do was worry if this was so sensible now, but then as he looked at his fingers and saw the long nails being painted a rich pink, he just thought of Lesley’s reaction. When they were finally satisfied, he looked in the mirror and smiled he was auburn with red tints, the hair was still near his shoulders, but curly and full of body. All he had to do now was get back to the hotel and see what Lesley thought. He had been gone hours and she was out looking for him, so he sat in the room and waited expecting trouble. Sure enough Lesley was really wound up when she came back to the room. She first wanted to make it plain how worried she had been, but Martin went to her and took her hand and said sorry. The nails struck Lesley then she registered the hair.
‘All by yourself?’
‘Yes, how do you like the new look?’
‘Great, I mean why’ so Martin explained the way the criticism had felt, and the salon’s acceptance, hence the result. Martin then feeling good about himself continued
‘For the rest of the hols I have decided, no more jeans, the only trousers will be those loose flares, I shall only wear heels, and I will not answer to Martin. Last can I have your purse, I had to pay cash and my card or cheque would not do, so here are mine, you can be Mr M Smith and I shall be your good wife, Lesley’
Lesley looked at him taking in what he had just said, then took out of the pocket her cards, ‘Lesley might take a little getting used to, but here you are Lesley’ she felt this was a big moment so told him what she had seen.
‘While I was driving around I found a funny shop, I think it sells stuff for cross dressers like us. Let’s go and have a look before they close’
Soon they were walking through the door of what looked like an odd clothes shop, a helpful assistant approached them and complimented Martin on looking so good. Then seeing his disappointment explained she had seen many cross dressers and knew what to look for. They had a good look around and came away with a pair of tits stuck to his chest, and a very tight g string that hid all his manhood perfectly, if a little painfully. They also bought a vibrator which Lesley could see uses for now he had lost his penis.
Then it was back to the hotel to change for dinner, which they both agreed should be something special to celebrate the new ‘Lesley and Martin’
The new Martin as good as her word wore a smart suit, while the new Lesley took ages to get ready as there was much admiring of the purchases to do, in the end he dressed in a soft calf length skirt with a flouncy blouse, bare legs and good to his word a pair of 3” heels that he had only worn about the house. ‘So this is how it will be for a couple of weeks?’ she enquired, ‘If you want it, then like I said you be Martin and I shall do my best to be your nice wife’ She took his arm and lead him out for a lovely romantic meal, followed by a romantic walk, and a particularly good night in bed, that is after the feet had been rested in a bar.
Next day he was lying in bed thinking about things, and was not satisfied with the pants that were supposed to hid his bits and felt he could do better. He went shopping after breakfast and bought some surgical tape, then shaved himself well and taped his penis backwards with the balls taped up as well, it was tight but looked really good, and he could always remove it if it was really uncomfortable. Then with the tits glued on as well, entered the bedroom to see her reaction. She was certainly pleased and liked the nude look but preferred some sexy undies to enhance the figure and hide the edges of the deceit. She flattered him making him feel brilliant, and the day went well driving around visiting places and stopping for snacks. Come the evening after dinner the got all randy and as he stiffened thought to remove the tape, but it was secure and not for coming off. So she took charge and gets the dildo out, eventually she has both relieved his hardness and penetrated him. Then after a clean up makes her tired wife pleasure her until she gives in and comes.
‘You are becoming more the girl aren’t you, what shall you do next I wonder’ she asked
‘Only responding to your masculinity, shouldn’t it be your turn to do something next’ they lay resting for a while.
‘I know what I shall do, the barbers for a proper hair cut’
She dressed in T-shirt and jeans, he in his flared trousers and pink top, and they went off to the shops to get her a proper barber haircut. She came out with a proper boy cut, all gelled to hold it as it swept backwards. They spent the day walking the promenade, and teasing each other over which could or would do the most contrary to their born sex.
The time passed quickly, they went walking on the hills, he was allowed to wear shorts and trainers for a change; they even went swimming in the sea. She wore a T-shirt to cover her chest, but bought Bermuda shorts, as being loose seemed better, he bought a tight costume with a high neck and built in cups. He managed a very obvious sunburn pattern, which would later make it difficult to take his top off in company. She also started wearing padding at the front of her pants to try to impress her maleness on others.
Towards the second week they noticed an advert for a dinner dance, she was keener than him, but insisted that getting all glamed up would be brilliant. So she bought tickets and made sure it was a smart do, then set about planning. Her best suit would do, but he had nothing, so they looked at dress hire, at salons, and accessories. She told him he had to shop alone, men rarely pick women’s clothes for them, so he rang in advance and told them his position to avoid embarrassing moments and then went shopping.
The hair would be easy as the salon he had already used took a booking, then he tried dress hire, there were three and one seemed particularly approachable. So explaining what he wanted to do, they told him to call anytime. This turned out to be a great choice, they had lots to choose from and very helpful staff, they would have him try on something and then say that’s not right and fetch something else. At last they all agreed on a cream dress, it laced up the back to giving a definite V at the front, the skirt coming down over the hips and then tapering in, with a split up the back so it was possible to walk. He left knowing the next shop would have to be for shoes, he did this by just window shopping until he saw gold sandals, then going in and as confidently as possible asking for a size 7, after 4 shops he found a pair, a bit higher than he really wanted but there was a clutch bag to match, so it was done. Just a pair of glossy stockings to find and it would be time for the hair appointment.
He was in a good mood and the stylist made suggestions that she wanted to try out so he sat back and was pampered. After what seemed like hours, he was ready to leave, they had tied his hair up and weaved some more browns and reds into it then teased it out into a star on his head, with wispy bits all round the edge, his nails had been redone in gold, and a trainee was asked to practise on his eyebrows. He felt great and went back to the hotel to put his feet up before getting ready, and see what his other half thought.
She came into the bedroom having spent the day on the cliffs, but even the windswept face could not hide the pleasure of seeing her wife relaxing and showing of such a great hair do.
‘That the dress over there?’
He confirmed it was. ‘I had best get a shower then and put my suit on.’
Lesley only had a man’s preparation to cope with. Martin had to do his face, change, make sure everything was right, then check just once more he was ok. Which meant he took ages.
‘The more we do this, the more you are becoming a right girl. Look you are fantastic, the hair is perfect, the dress flatters your figure, the whole you is screaming gorgeous woman. Now come on.’
They ate and danced until the early hours, then after the taxi had dropped them off and the laces had been released, they made it to bed to finish off their evening with some enjoyable sex.
The rest of the holiday was something of an anticlimax, Martin was still going about as a woman and Lesley was still playing the husband as they went about their holiday activities, but at the back of their minds was the nagging thought 'What happens next Monday?'
Eventually the discussion happened. Lesley it was accepted would hardly change her image, work for her was a male thing now and she would be wearing a shirt and tie anyway, but Martin could not turn up unexpectedly with long nails, a ahir style screaming 'female' let alone the idea of wearing a dress. He enjoyed his job and did not want to upset that, so come Sunday he had to colour his hair a more natural shade, remove his nails, which was hard, and try to obliterate any trace of the holiday excesses until he was happy Martin was ready for an appearance at work.
The holiday had had a deep impact on their relationship though, and Lesley was most definitely now the man at home as well as at work, and Martin was only to happy to spend his weekends in one of his skirts. His nails over time bacame more manicured, his face less bearded as the electrolysis slowly cleared the hairs, but it was his walk that got noticed most, he minced a lot and used gestures others called camp because they saw him as a man, but he considered feminine. His confidence at work overcame any teasing he recieved about his lingering femininity, ultimately he was just accepted for what he was, a camp man who was good at his work. Lesley just got on with being herself, months later learning that she had been rumbled at her initial interview, but because of the effort she had made no one challenged it and she would have got the job anyway. But after all these months looking manly, she was not ready to give it up, she felt it created a no nonsense image which made managing easier even if some made comments her behind her back.
But most of all they liked the way each other looked and behaved in their new relationship, especially at the weekend when they relaxed and could be the husband and wife they most enjoyed.
Match Making
by Lauran
I have mostly normal boring friends, but a few fall outside these boundaries. Two such people are Jerry and Phillipa.
Both are seemingly confused individuals who are unsure what they like in a partner, Jerry says he likes women but spends all his time in gay bars where he says he feels more comfortable, and has had a few relationships with men. Whereas Phillipa fancies women but will not admit to it, so goes from one man to the next each time getting all excited that this is 'mister right' only to say a few weeks later how wrong she was.
Well Jerry had split from his most recent partner a few weeks before I set up a blind date with Phillipa. I thought they might hit it off, mostly because Jerry when it comes down to it, he is such a girl, and Phillipa is the bossy controller who would look after Jerry; in my mind it was perfect.
I had felt a bar in town would make a good meeting place, of course Phillipa turned up at the time I said I would be there, but Jerry got himself mixed up with timetables and arrived late, rather as expected. Anyway after I had introduced them and they had accused me of setting them up, which I denied, but called me a schemer who one day will be set up myself. After a shaky start I managed to keep the chat going, we had a meal then went our separate ways.
It was a couple of weeks later when I saw Phillipa, I had to ask if she was seeing anyone, and admitted to having gone out with Jerry a few times, but he was hard work. She then told me his faults, which is usually a prelude to a break up, but underneath I could tell she liked him. She let slip how much she liked him, by saying that he would need to get some better clothes that suit him, and she was going to work on getting him organised. This seemed quite positive, and as I gave her a kiss, I said I hoped it worked out well; her reply was 'I hope so too, he is sweet'
The next time I bumped into them Jerry had lost his T-shirt and jeans look, instead he was wearing loose cotton trousers and a nice v-neck jumper. We kissed and I told him he looked nice, Phillipa was glad I liked the new look and told me they were on a diet. She was starting to control him I thought, but that is what he needs she would say.
I had lunch with Jerry later in the week, I wanted to know how it was going and if he was happy. Again was he dressed nicely, only this time it was a lemon jumper and jeans, which he would have had to pour himself into they were so tight. We chatted about general things, then I turned it to Phillipa, he was happy I could tell, he said he was in love and thought she loved him. I asked him about the clothes, he just said that he was rubbish with clothes, which was why he did the jeans and t-shirt before, but Phillipa was great she would find things that looked so good and felt lovely. When I asked about the jeans because there were no obvious underpants and they had a flat front, he admitted to wearing a girdle and that Phillipa does not like a bulging crutch look. So with my questions answered I left to wonder what else besides a girdle and lemon jumper she might get him to wear wear in the future.
Phillipa rang me and asked me out the next day. Jerry had talked about our meeting and she wanted to make sure I was not jumping to conclusions. So I told her how happy he seemed, and that he loved her. She blushed at that and said she knew. Then she asked what I thought about how he dressed, I said how nice he looked recently, which pleased her.
'He's not too effeminate is he?' she asked, I replied telling her he was such a girl at heart effeminate suited him. 'Oh that is good then, it was just I thought his hair would look good with highlights, what do you think?'
'Yes, but it needs tidying as well, it looks as though it has not been cut properly in years'
'I know' she confirmed 'He says he find barbers difficult, so I was going to suggest a unisex salon' I smiled at her
'When it is done let me know, I would love to see how it comes out' to my surprise she said 7pm Saturday.
So at 7 pm I found them having a coffee on the High St, at first I did not recognise them, Jerry had lost his pony tail and had lovely straight hair parted to the left a fringe sweeping across and behind his right ear, the dull mousy brown was brightened with silver and gold streaks. As if this was not enough he had a black shirt that shimmered as he moved and baggy linen trousers. He looked great, and as I leaned over to hug him told him so, and asked him to stand up and give me a twirl, which to my surprise he did. I then noticed Phillipa, she was different but not so much, her hair was slicked back, no make up (not that she ever wore that much) a plain cotton shirt and brown chinos. It was great to see them with their new image and looking so comfortable. I had a coffee with them and we chatted aimlessly. Then as we got up to leave Jerry picked up a black handbag, I suppose I should call it a man bag, but it looked so like a clutch bag, he noticed me looking at it and confidently told me the trousers did not have pockets, and if they did filling then with money, phone etc would spoil the line. Well I thought, that is not something you expect to come from a man is it. But then as we walked to find somewhere to eat he linked arms as a girl would, Phillipa just keeping her hands in her pockets. All I could think was, how right I had been, they were meant for each other.
It was Monday the next week I had a call from Jerry, obviously feeling down and wanting to know if he was right for Phillipa, if I thought his new look was acceptable, did he look like a girl or a man? I tried to keep him calm telling him they were well suited and had never seen either of them more at ease in a relationship. As for the image, he should wear what he is comfortable in and he likes wearing, but comfortable does not always mean easy rather what he can feel relaxed in. Apparently someone at work had teased him about his new hair, and ten compliments can be undone with one sour word. So I told him to think of Phillipa and ring her.
Next I had a call from Phillipa worried by Jerry's call, she needed to know if they were right together and if Jerry was being too effeminate, I asked her if she had used her new look for work. Indeed she had and it was going down well, she was finding people reacted differently, it seemed getting things done was easier if you looked a bit butch. As for Jerry, I told her to let him find his feet; a new hairstyle always takes some getting used to for the person and those that see it. She seemed satisfied with my words and rang off saying she would be in touch.
Phillipa had said she would keep in touch, but my texts fell on deaf ears for at least three weeks. I was getting worried about Jerry, as he was not responding either. Then Jerry bumped into me quite by accident, as usual he looked pretty, and when I asked why he had not been in touch he said they felt they were using me too much as a support for their relationship and they needed to work things out between themselves, well that was the short version. So I insisted he meet me later for a take away and fill me in on what I have missed while I was not 'supporting them'.
He did come later, and he had a different outfit on, something the old Jerry would never have done. Now he had tight hipster jeans and a lilac slash neck jumper. I told him how nice he looked and how much I valued his friendship. He talked about how one person teased him at work, but how the women in particular seemed to be more relaxed around him, the men he had never really felt at ease with still had the same effect, except for the one that was horrible, and another who Jerry was sure was trying to chat him up. He also told me he was going to the salon again, when I asked why he said his hair needed tidying and the roots doing, besides he had liked the attention he got being pampered. It was about this time I noticed how nice his nails were, not long, just neat and manicured, he blushed when I pointed out how nice they were, he just said he was bored watching the TV a week ago and started filing them and one thing lead to another. What he did not say was how did the polishing kit happened to be in his place to start with. He left early because it was work next day, and I made him promise to call at least once a week, and Phillipa had to call me before the weekend.
Phillipa was a stunner next time we met, her hair was shorter, like a feminine boy cut, side burns, cut around the ears but with soft edges. She was never big chested but she must had had a sports bra on to be that flat. I did not know whether to hug or shake hands. She looked happy and told me how well they were getting on, apologised for keeping a distance, but they felt stronger now. She had got promotion at work, a move up in charge of a section, apparently they liked her no nonsense approach, she thought they chose her because the men did not feel she was using sex to get things, as the other women had turned up in low cut or short dresses for the interviews. When we discussed Jerry she went a little dewy eyed, still in love I thought, I asked how she coped with him being so girly did it not attract comment. She truthfully told me she would have him no other way and had bought him clothes to try at first but now he was buying his own, on his own, and promised to get him to come out at the weekend in his latest outfit. I said I couldn't wait, which was an understatement; I wanted to know what Jerry would wear that was going to be more OTT than I had already seen. I would just have to wait.
For all my eagerness at meeting them, I was delayed and met them later than arranged. They were in a bar with a dance floor and enjoying the dance when I eventually spotted them, which had not been easy. Phillipa was so butch, combats, boots and a loose jacket hid everything female, whereas Jerry was being feminine, as she had said he would, his hair had been treated to a session at the salon, still streaked but wavy in a scrunched up way with clips to hold some of the longer fringe hairs in place. If this was not enough, and it was the outfit I had come to see, he was in a pinkie/brown roll neck top, with cream silk trousers that were tight around his groin and arse but then flared out to an enormous hem, and though I did not see them till later he was wearing brown kitten heel shoes with pointed toes. Absolutely wonderful I told them when we found a drink and a quiet corner. 'You like it?' they asked 'I love it' I replied 'the hair, the clothes, the look, just brilliant'
We had an excellent night, I got asked for a few dances, but mostly I danced with my friends. I kept reminding them how lucky I was to have such wonderful friends.
Next morning I woke at Phillipa's place, sleeping on the couch just in my underwear. Barely awake Jerry put his head around the door to see how I was, and then stepped in with two coffees. It took a moment to register, but he was wearing long lilac silk kimono wrap and without any comment sat opposite me, wrapped the silk over his shaved legs and asked how I was. After a bit he explained he did not have a dressing gown but Phillipa had this one she let him borrow when he stayed over. Maybe I was not fully awake and the restrainers were not on my tongue, but as we chatted it slipped out about how easy he could be mistaken for a girl, he said it happens all the time, so I tried to find out more about why he was wearing such feminine clothes, like a silk kimono. All he would say was he enjoyed looking that way, I asked about how his crutch looked anything but male and neat like a girls and how it must be uncomfortable, he admitted it was a bit, but Phillipa liked a flat front and the clothes look so much better flat, which I could not deny. When Phillipa turned up in a rugby shirt and jeans, I knew this gender bending was not for show, but I would like to know how far they would go, but kept that one to myself.
The times we meet after that they were far less OTT, but still most definitely butch and girlie. Jerry seemed to be spending more and more time at Phillipa's, so it was no surprise to find out Jerry was moving in and as I had a car could I help. Of course I would
It started with a trip to a tip, then a more telling one to a charity shop, all of Jerry's pre Phillipa clothes were bundled up, and what I thought were his favourite jeans and t shirts were given away. Then we had to remove all his new clothes, I was impressed that a man could have so much and such a quantity of soft and luxurious fabrics, that was without thinking about the colours, this was definitely not a dark suit wardrobe, but the most interesting find was that he had more than the one pair of heels I had seen, he also had cowboy style boots with a block heel and some colourful flip flops with a wedge heel, not high, but high enough. All I wanted to find was a dress to satisfy my nosiness, but he either did not have one or it was well boxed already.
And so a week later I had Jerry alone one lunchtime, having a coffee when I felt bold enough to ask if he would ever go completely girlie and wear a dress. He was quite shocked by the comment, but I carried on by reminding him of the things he was already doing, the silk trousers, shaved legs, streaked and styled hair, manicured nails, need I go on I asked. It was then I noticed how well defined his eyes were, and added, mascara? 'Yes' he replied 'it makes my eyes look so much better, don't you think?'
I had to see Phillipa, so I 'accidentally' meet her after work. After a pointless chat, I asked how far Jerry might go, I mentioned all the things he had changed, and she loved them all, the smooth skin, the elegance of his hands, the way his eyes looked adding that he was going to ask the salon to pluck his brows next time he went.
'So when do you get him in full girlie dress?'
'Oh I don't know, but I shall not be surprised if he comes home having seen something he likes, and asking what I think'
'and what will you say when that happens'
'depends if it looks good on him'
I left it there and went off wondering just how girlie Jerry would become.
Our Saturday nights out were becoming more common, and Jerry was becoming more of a girl, as Phillipa would complain how long it took him to get ready. It was a few weeks since his last pampering at the salon, so I was not surprised to find he had been again and followed through with the brow plucking, but they were thinner than I had expected. The fine eye liner was unexpected as well, fortunately he had only had his hair washed and blow dried, so it was not that difficult to find him in the crowds on the evening. He was once again flamboyant, in silk trousers with a brown sheer top with full sleeves that finished at a satin cuff, and below the satin bow that sat at his neck I could clearly see a chemise, added to which the kitten heels I knew about had become 2" sandals. I said nothing except how lovely he looked, but to myself asked how long before he goes over completely.
I slept on their couch again, and once again had a coffee wrapped in a blanket the next morning, Phillipa was in a grey towelling wrap, and Jerry had satin pjs on, with the kimono covering him. As I had a wash I had a nosy in the laundry basket, there were nice knickers and boxers, some nice camisoles, knee highs and normal socks, nothing that I could say was not worn by one or the other equally, though the camisoles I doubted would be under Phillipa's shirts. Then I heard Jerry outside the door 'is this what you are looking for?'
'Pardon' I said,
'I think you should be less noisy when you start rooting'
I tried to sound confused 'sorry I don't know what you …..' I nearly said mean as I opened the door, but Jerry was dressed in a long gypsy skirt and a matching peasant top, so I temporarily lost the use of my mouth. 'Why didn't you tell me, you look great it suits you' I eventually managed,
'not for work though I think'
'no not for work, does Phillipa like it?'
'Loves it, but says I have to go for the complete look if I am to wear it for going out. So what size tits do you think would look good, and Phillipa would like?'
'Never thought, how much of a statement do you want to make?'
'Well they might as well be seen'
'C or a D then. I suppose you have everything else'
'nearly' he replied ' I need to have a lesson at the salon about make up, and I want to get my ears pierced'
I then hugged him 'I am so pleased for you'
Next weekend we met for a meal, Phillipa not to be outdone was in a neat suit with a collar and tie, Jerry was in the gypsy outfit, but the top was filled with a chest, he had hoops in his ears, his face made up disguising any remains of the man, his neat nails were a delicate pink, and he had gone for black stiletto sandals, and a proper handbag that hung of his shoulder. I knew it would come, but calling Phillipa, Phil took some getting used to, whereas Jerry just stayed the same, though I guess he was spelling it differently.
Over the next months I meet the couple on various occasions, when it was daytime they toned down their obvious alternative gender positions, Jerry would most likely be in linen trousers or hipster jeans with a cashmere top, whereas Phil would be in a suit or chinos as management roles required a certain dress code she said. But of an evening and weekend, Jerry in particular went overboard, certainly he would wear some fabulous trousers and tops, but increasingly he was buying skirts, and of a more sexy nature, but no matter what he wore he was always a lady away from work, with make up done to perfection.
One night he was dressed in a silver tube dress that was so clinging it showed the suspender clips through the fabric, as always he looked brilliant, and after a few drinks I asked if the ever thought of taking it further with drugs and surgery, the look of shock was not expected. Phil who had been fondling Jerry all night was first to say 'Oh no, we couldn't loose those bits, might not be big, but quality counts don't you think' Not for the first time I had lost the use of my tongue, how could I possibly respond to that? So I didn't.
It was about two months later; Jerry was home alone with Phil working away, when he invited me round for a Chinese take away. As always he was pretty, pink top with spray on trousers. We chatted about things then there was a pause, as he seemed to be building up for something.
'Do you think Phil would like me to have real breasts?' in the silence that followed I looked at his chest, the pink top would look good with a cleavage but Jerry is a man.
'Would you like them?'
'I think so, and Phil does like me wearing the falsies, so I wondered about getting some real ones'
I was trying hard to think fast 'it would move you from effeminate, flat chested man to definitely female you realise'
'Yes I know that, and I would need to put across as female all the time' this made me smile, when had Jerry ever come across as manly?
'And how would it go down at work?'
'No problem, got a new job starting next month, working for a firm that cleans peoples houses'
I thought again and sipped my wine 'So when are you going to tell Phil? And how are you going to get the extras?'
'Phil doesn't know, and I was hoping you would run me to the clinic tomorrow, and pick me up in a couple of days' he smiled and gave me a puppy dog look. How could I refuse him, so I stopped overnight, and rang into work saying I would be late, then ran him to the clinic and left only when I felt happy he was settled. I wanted to call Phil but was made to promise it was to be Jerry's surprise.
I picked him up a few days later with a bandaged chest and a handbag full of painkillers, I made him stop at mine till Phil was back, then he would just rest. His plan was to have the bandages off and a bra on when Phil returned. The bandages come off the Friday before Phil was due home on the Saturday. He was still sore but in his soft supporting cups, the chest looked perfect. I only wished I could have been there when they meet. But I did get a call from Phil thanking me for looking after her partner, and telling me how good he looked.
I found some weak excuse to call round, though I really did not need one, but I wanted to see the unwrapped Jerry. So with time to get ready for my visit he went all out to impress, or that is how it seemed to me, forget the silk trousers and 3" sandals, it was the bustier below the bare shoulders that took me all my time to stop staring at, there was even a fair bit of bust pushing out the top of the purple satin leaving nothing to the imagination top.
'I guess you like the finished article?' they both asked,
I tore my eyes away and tried humour 'you seem to have put on a little weight' was all my mouth could come up with, while my head was saying gorgeous.
Jerry was soon at work, and enjoying his Mrs Mop job, but still found work clothes that flattered his figure, not bad when you wear a tabard with the company logo on it. Phil was moving up the cooperate ladder, but promised never to be away so long that Jerry had time to do anything quite so dramatic without her knowledge, the chest was nice, but did not want any more changes.
I had only thought that they might get on well when I first set up the meeting, that they would end up living together as husband and wife virtually was beyond my imagination. But now when I saw them together they seemed so comfortable with each other, and with themselves.
British carnivals are different to other countries. Sometimes something quirky appears in amongst the familiar sights.
I was sent to cover the local carnival, it was the usual, morris dancers, brass bands, school floats, may queens and people in fancy dress collecting for charities. Nothing unusual or worth writing about if truth be told, Sean was taking lots of pictures and I was going round looking for the personal stories to add to the pictures. I was picking up the usual things about families and local connections, then I came across a may queen story to cap them all.
It was the car that got me first, a Morgan, always liked them, anyway I went for a closer look. These girls are either mummy's barbie doll or so up themselves it is unbelievable, so I don't often ask them much, however sat on the back of the Morgan was a pretty girl but the name plate called her Samuel, so I took a closer look and if I used my imagination then yes this girl might just be boy. I had to ask some questions, the first one I wanted to know was 'Are you really a boy?' but it would not be the first, that would be rude.
'Hi my name is Amy, you are from?'
'Littlemoor' replied my interviewee.
'That is a few miles away?'
'Took about an hour to get here'
'Have you enjoyed the parade?'
'Been fun'
'How many have you been in this year?'
'This is the third, mum wants to enter a couple more'
'I can't help noticing the board says your name is Samuel, is that right?'
'Off course it is, but most call me Sam or sometimes Sammy'
So now comes one of the oddest questions I have ever asked 'So Sam I am wondering why you have entered a may queen contest?'
And then this boy I guessed to be fourteen started to tell me why he was sat on the back of a Morgan wearing a pale pink gown with organza skirts and a satin bodice, with a perfectly made face, his hair in tight curls with flowers threaded into them, pink net opera gloves on his hands and a small parasol by his side.
It started at school when it was announced that a May queen was being looked for, it was included in a newsletter that Sam took home, where his parents read it and in their usual liberal way saw it as a sexist contest that also discriminates against boys. Sammy told me they often took up fights over such issues, but they often end a few days after when they have calmed down.
'So why was this one different?'
Turns out the reason Sam's parents did not let go of this one was Sam's stubbornness. They said a boy should have the opportunity to be a may queen, and that Sam should put himself forward. He said no and that was it, he had a long talking to about equality and no sex is better than the other etc. and then to his shock they approached the school who put them in touch with the organisers, who also got a lecture on equality, by the time a week had passed Samuel was the only person who had either offered themselves or been proposed by others to be the May Queen.
'But you could have said no'
He could have but he had the same values as his parents and felt a point should be made, so he went along with it, right up to the point that it was made clear by the organisers that a may queen should look like a queen, not a king. By which time Sam and his parents were in too deep to back down without an embarrassing climb down, so at his parents insistence and the organisers muted enthusiasm, Samuel became this years may queen for Littlemoor.
'You look very err can I call you pretty? You could have played it as a drag artist might and exaggerated the feminine style'
Sam thinks that a couple of women who organised the may queen were not happy and made it as uncomfortable as possible, he thinks in the hope he would back out, but his mother just upped the ante every time they made a suggestion his mum embellished it. They said he must wear a dress, his mother found the pink one he was wearing, a plain dress would have done but he had this one. He stood up so I could take in the meringue of net skirts that created a fantastic look.
'It looks fantastic, do you not mind being seen in it?'
He had had quite a bit of teasing at school initially once the whole thing of him being the may queen became public, but he seemed to be the sort of lad who does not take such things to heart and would tell them about his views on male and female equality. In the face of strong opinions most teenagers back off. He did admit that having his hair permed was rather embarrassing.
'You had your hair permed, as in going to a salon, curlers etc?'
Turns out one of the organisers has a salon and said that she would give Sammy a cut and blow, but in a fit of not showing weakness his mum suggested a perm would look good, the organiser agreed, and the tight curls with flowers was the result. He had even gone back when the curls lost their tightness he said. School he admitted was a little difficult for a week or so and he was hardly ever called Samuel now, most common was Sammy.
'And do you mind the name and the look?'
Not really he told me, he was not a sports sort of lad, breaks were often taken up going for walks with friends or just chilling on the edges of school. He had made new friends because of the may queen, though I guessed he had lost quite a few.
As we talked I noticed how feminine his gestures were, his gloved hands sat in his lap, every now and then the breeze disturbed his hair and a very effected hand moved it back into place. He was sat very prim and proper without a back support. Then I noticed his shoes, pink off course but with heels on that I guess were 3" and high enough for wearing all day I thought.
'The shoes, you have heels on, but no one will see them.'
His mother, or mummy as he often calls her, felt that he would need to have a female gait and heels would help with that, it was not all riding around on the back of a car he insisted, there were interviews and judges to meet, so if he was going to look like a queen then he needed to move like one.
'Have you won any of the contests?'
He had not won anything, I don't think I needed to ask why, being a boy would be a hurdle to many for most judges I guessed. Did he mind not winning. No it seemed he enjoyed being able to make such a public declaration about his views. But as he did so he rearranged his skirts, tucked his feet underneath and put a wayward hair back into place, and I thought, he also quite likes this. So equality of an unexpected kind. Some girls like going around looking and behaving like boys, here is a boy who likes looking like a girl.
'Thank you for your time Sammy, could we take some photos for the paper and do an article about you?'
'Not a problem' and he struck a very feminine pose for Sean 'Just let me see what you write before you print it, daddy says newspapers don't like the truth, so I just need to know what you say about me first'
'I shall Sammy'
'It has been nice talking Amy. Can I ask you one thing?'
'Yes, go ahead'
'What is the perfume you are wearing?'
After all the things he had just told me, that was the most shocking. A teenage boy had just asked me about my perfume and it would not be to buy a gift for me I was sure. 'Obsession'
'It smells gorgeous, I think I shall ask mummy to get me some'
Lost for words I walked away with Sean already onto another photo opportunity.
I wanted this to stop, it was going only one way and I was unable to say no anymore.
I had given up wearing Y fronts in favour of satin knickers long ago, that was my choice.
It was his choice that I wear matching bras as well, he said to help me feel more feminine. When I said it made me nervous I could be found out he came out with a simple solution, stop being a Saturday girl and be pretty every day.
Well it was training bras to start with, virtually no cups but that changed when I started to grow larger nipples and then small breasts, then I needed a soft bra to stop my shirt irritating the nipples. I suppose it could be said wearing a bra is now my choice.
It was also my choice I suppose to pluck extra hairs from my brows when he said we were going somewhere specail at the weekend.
And it was my choice to let my nails grow into a more almond shape after the glue on ones broke off one Saturday night in bed and pricked me.
It was his doing that my jeans got ripped when all my other pairs were being washed, meaning the only trousers I had to wear to work were my female suit trousers, boot leg with a fitted arse. I expected comment at work but no one saw them under the desk.
I chose to let my hair grow, I just hated the wig especially in summer, but it was my sister who trimmed it so it looked more female than male. I just did not have the strength to go and get it cut short again after the months of waiting for it grow. So I had to live with a nice girl’s style.
It was work who made a decision for me. I was called into the main office, the management team facing me looking quite amused. I was wearing my white underwear, not that they knew that, a pair of grey trousers with an interesting side fastening, my eye brows had been thinned just a little more that weekend and my sister had cut my fringe so I had to use Kirby grips or gel to stop it falling across my face. Not hearing them right when they commented on my appearance I thought I had not cleaned all the makeup off from the night before but they were more concerned about the gossip my ‘alternative style’ was causing. They asked if I was transgendered, because if I was then I should be open about it, if not then dress appropriately for a man. I said ‘Oh right’ and went away to think about it.
By the following Monday I had not been able to take scissors to my hair, or deny I liked the satin underwear, and I wanted to let my nails grow a little longer, so I told them I was transgendered and wore the jacket to the trousers and a nice white blouse made of lovely silk and my comfortable heels to work.
Work has set in place paperwork to recognise my changes, and my boyfriend has asked me to move in on condition my male clothes don’t.
And all because I like to wear nice satin briefs.
My wedding dress story
by Lauran
Don’t ask me how it came up at the beginning, I was round at Mark’s house and we had had enough of his new game and were just sitting about chatting. We touched on our lack of love interest, how possibly girls weren’t keen on gamers, what game we should get next. Usual seventeen-year-old stuff, well we thought so. Mark came out with the statement that his ideal woman would be someone like me, except she would obviously be female and not a weedy lad, someone who would play x box and chat, like we did. I thanked him for what I think was a compliment and tried to change the subject, though he was my best friend and got on really well I was not sure I saw him as my ideal partner.
It was at the end of college on Friday that Samantha caught us on our way home, gave us an invite to her party then ran off with her boyfriend. We read it, looked at each other and just said no. It would be couples and trying to pretend they were grown up, and for Mark and myself a gooseberry situation. Anyway Mark’s mum found the invitation and I happened to walk in on the conversation, Mrs Jones thought Mark should go, he had not been to a party in ages, and sitting playing games with me was no way to spend a Saturday evening, besides it was fancy dress which would make it more fun. Mark was not keen and suggested we had no costume or money to hire one, then I saw her face light up, she spotted her wedding photo and told Mark he could borrow his fathers wedding suit, a proper morning suit with hat and tails, the lot. Mark was not keen and pointed out I still had no outfit and dressing up as a groom would look odd, what did she have in mind for me, the wedding dress. Her answer took the wind out of our sails, she said why not, I am about the size she was twenty years ago, and we would make a good pair. I chipped in suggesting my mother might not be too enthused about her boy running around in a dress, and after a moments thought she rang her and asked her to come round, which is only three doors away, so was there in no time. I was trying to play it cool, I did not want to let on that I had enjoyed a few evenings alone in her bedroom imagining myself in her clothes, and the idea of wearing a wedding dress was secretly quite appealing. Anyway my mother and Mrs Jones quickly covered the discussion so far, and as I brought up the fact that my mother would hardly like to see her son parading around in a wedding dress, she just asked why not? I was a little stuck for words, coming out with things like, it’s not right, men are men, men wear trousers. They both shot me down, told me not to be sexist, that men wear trousers and so do women, women wear dresses so why should men not wear them also. I gave in as I was clearly losing the argument, but inside was having mixed feelings about how this adventure would work out.
Our mothers left us to discuss our fates, Mark only had one comment, that he would get his ‘wish’ I would be his girlfriend, how could I forget his statement a few days before, and told him I expected him to be a perfect gentleman. It was not late when I left with my mother and a dress bag that I assumed correctly contained the wedding dress. Mum was trying to get me talking about how I wanted to play the part, did I want to be a drag queen type, a clown style or a proper looking woman, when I asked which she thought would be best, she was in favour of a straight forward woman look, because Mark would be a normal looking groom so I might as well compliment his approach.
Mother started on me the next morning, it was Saturday and she was not that busy so it would be a good time to get the outfit sorted, I had hoped to do this all privately but mum had other ideas, I was in my briefs letting her put the dress over my head soon after breakfast, and she was making notes, I needed a chest, the hem dragged on the floor could it be turned up? My arms looked quite hairy, that needed sorting, and my hair was a scruffy mess that needed attention. Many other items were mentioned but not noted and I was feeling this might not be as much fun as I first thought. Over a coffee Mrs Jones arrived and discussed how things were going, Mark had had a fitting also and was apparently a spit of his father back then, he needed a haircut and a good shower and that seemed to be it for him. I overheard the topic of the hem come up, and Mrs Jones asked how short was I, only a couple of inches my mother informed her, they did not want the hassle of alterations and decided if I wore heels it would fall right. Then they talked about hairstyles and make up, then how to get them organised. I was starting to feel left out of it but waited for Mark’s mother to leave.
I asked mum if all the things discussed were essential, she was sure they were, so I asked if walking in heels was difficult as I hear women complain about them, not sure what the answer would be, she might even encourage me to try them, and she did, I tried not to look too pleased at the prospect of wearing heels but I possibly did not do very well at lying as she went to her wardrobe and found some sandals that could be adjusted around the ankles and told me to give them a try. She said they were only a low one and I agreed I had seen higher, but that did not help me as I staggered about hoping to find my balance, which prompted her to say that I did need practise because the dress would need me to wear at least a three inch heel. This was not going to be easy she reminded me as she told I should wear the sandals around the house for the rest of the day, and that seeing as I have never worn a skirt, let alone a full length dress it might be good to get some practise in there also. Anything else I thought, when she came out with ‘If we are going for authentic, maybe we should get your ears pierced?’
I asked if I had any say in the matter, to which she replied, not really, if I was going to be ready in a fortnight I would need to start getting ready now. Saturday went fine, when I was in the house I wore the sandals but changed when I went to Mark’s, who was quite downbeat about the affair, his mum wanted him to loose a few inches from his waist and get a proper haircut, like men should have with ears and collar showing, I told him some of what my mother had in store for me but assured him it was fine and in fact could be something of a challenge, for which I got an odd look of him.
Sunday morning and mother had been through her old clothes and found an old maxi skirt from her college days telling me I should try it so I can get accustomed to the feel and length of a long skirt. I agreed hopefully not to quickly and as I had lots of homework to catch up on spent the day in the sandals and skirt, and came to no harm.
That is except for early afternoon when I changed into my jeans and trainers and went with her to the shops, I came back with two sore ears and ring sleepers fitted in my lobes.
Monday I had a few at college ask about the ears, most saying how cool they looked which made me feel better, but it was when I got home my good mood wore off, a note from mum saying ‘Get changed then make a start on tea, don’t forget to use an apron’ I could only find her apron but wore it to keep the peace when she got home. Then I had another shock, she was late because she had been shopping at a discount shop and had me so I had some heels of my own, a plain court shoe with a towering, at least I thought so, three inch heel, to get used to the height she assured me. They were a tight fit which stops them slipping off, and I was to wear them whenever I was in the house instead of the sandals.
Tuesday I went round to Mark’s for a rest in the evening, he loved the earrings.
Wednesday, Mark came round unexpected, I was in the long skirt and high heels, he said nothing but I would catch him taking sideways looks at me, and I told him not to tease as I would get my own back later if he did.
Thursday, mum is making plans for the weekend, I am not sure of them all but I shall be busy it seems if all the calls she has been making are anything to go by. Got the skirt and heels of to a fine art I think.
Friday, mum wants me to get into an authentic girl mood and had got me a nightie, to prepare me for Saturday she adds. What will happen on Saturday I ask, nothing I won’t enjoy she reassures me. I put on the nightie before going to bed and showed her how it looks, I get a kiss, that has not happened for years, maybe she likes this as well.
Saturday, in the morning she gives me a make up lesson, first showing me how it is done, then cleaning it off and guiding me while I try to repeat what she had created. This feels a bit weird as I am in the nightie with her silk wrap tied around me. Once she was happy I had mastered the basics she tells me it is time to get everything sorted with the dress, a pair of control pants to keep everything controlled at the hips, a bra stuffed with tights to give me a big enough chest she hopes, then the slip, then the dress. To my embarrassment Mrs Jones is invited round for advice, the bra needs to be bigger, and my waist thinner to get the dress fitting right. Fifteen minutes later Mark’s mum is back with a corset and one of her bras, twenty minutes later I am putting my arms through the sleeves again and letting them button up the rear closure. I am uncomfortable but told it fits perfectly. Stepping into my shoes Mrs Jones asks if I would mind trying four inch heels so the hem is just that little bit higher, my mother says it wont be a problem, I just let out a girlie squeak and they have a fit of giggles, and hug me.
After Mrs Jones has gone and the dress hung up, mum tells me I should keep the corset and bra on so I can get used to them, and gives me one of her knitted tops to wear along with the long skirt which now sits more on my hips and therefore lower down, this causes me to be extra careful not to stand on the hem as I walk, I had already got used to lifting the hem when I walked upstairs, but this was needing a different gait to keep it out of the way, I was developing a very affected female walk by mid afternoon. Though I was not told to keep the make up on, I made no move to clean it off which prompted mum to suggest we try something extra on Sunday, when I asked what she clammed up.
I did not go round to Mark’s, so he came round to ours and got to be the first person to see a fairly complete female version of me, he said I looked hot, and asked if the tits were real, I told him to grow up and turn the X box on.
Sunday. Woke with nightie wrapped around my legs, which was very nice. Over breakfast, still in the nightie, mum tells me to have a practise with my make up and to wet my hair. Then while I am brushing cosmetics onto my face she is brushing and combing, then using her tongs on my hair, by the time we are done I look completely different, especially now my face is framed by my neat hair style, but all the while she was talking about how it would look best the next weekend. Instead of the long skirt she gives me a pair of cream silk cargo trousers and a green vest top, saying I could do with a change.
The afternoon is spent studying and trying to tell myself I will get used to the corset and bra. Then as I am expecting mum to tell me tea is ready she comes in with a jacket and a shoulder bag, ‘Right time you had a go at being outside, and being seen. Here put this on we are going to pizza hut.’ I would have objected if I could get a word in as she explained how I needed to be comfortable out while looking female, and learn some of what I need to know about female behaviour.
The next shock was the Mrs Jones and Mark were at the pizza hut already, Mark looking more nervous than me. Our mothers got on well chatting about this and that, but mostly about us, the comment to cause the most reaction from us was that seeing as we were bride and groom next weekend, at least we should be boy and girlfriend at least once beforehand, they had even got us to sit side by side on a small bench seat. Mrs Jones was full of praise for how mum had transformed me, and that the party would be great. Then to cap it all, mum invites Mrs Jones to go with her, and leaves Mark with their car to run me home.
This was getting a bit to much, a bit too fast I thought, our mums were setting us up like a blind date other than we were best friends. We drove to our house, I invited Mark in for coffee, and as we relaxed he comes out with ‘you don’t realise how good you are do you. No one took a second glance at you. You are prettier than most of girls in our year. You are great at this you know’ all I could do was blush and drink my coke.
When mum got home she made Mrs Jones a vodka and tonic, and then asked how we had been and did we want anything, I asked what was she offering as we had already had a coke, to which she said what did I fancy, a drink like Emma (Mrs Jones to me), I said I would try one and Mark had a lager because that was what he felt a man would drink. The next set up was that I ended up getting Mark a fresh lager only to find my seat taken and the only free one was next to Mark. Emma and mum then started teasing Mark that he has a pretty girl next him and why has he not put his arm around me, they hoped he would be more affectionate to his bride in a weeks time. The lagers and vodka relaxed us and after much teasing I cuddled up with his arm over my shoulder. Last blushing episode came as they got up to leave, as we said our good byes and Mrs Jones put her coat on, she nudged her son and told him he should say thank you for a lovely evening, I imagined what was coming, he said the words and his mother reminded him I was his girlfriend for the evening and had he never said good night to a girl before? He gave me a peck on the cheek, that was not good enough, and was asked if he needed showing what was expected, so he kissed me on the lips, which got an approval, ‘Now we are just going out to the car while you two practise properly, and we shall be checking’ they both grinned as they left us.
‘So are we going to do this and keep them happy?’
‘If you are ok with it’
Then I leaned forward and kissed him properly, hand round his neck so he couldn’t escape and moved my lips in an appropriate manner. Mother came back after a few minutes, ‘There is no stopping you’ we separated and both said ‘what’ together ‘it was your idea in the first place’
Anyway after they had gone I sat with mum cleaning my face and getting into my nightclothes discussing the evening. She had had a great time, she admitted some of it at our expense, but I was a great girl and that I would be terrific in the wedding dress.
Monday, it was back to earth and college, and a hangover, three vodkas when you are not used to them is hard and Mark was the same, added to which neither of us knew how to react after our good byes from the night before, something had changed in the friendship and we could not explain it to each other or ourselves.
The evening saw me in heels and skirt preparing tea once again, when mum came in with a shopping bag, ‘For you’ I opened it to find a pair of what I guessed to be four inch white stiletto sandals, ‘For the wedding’ I let out a exasperated mother, but she assured me I should get them on and get used to them as quickly as possible.
Tuesday, I was going to put on the long skirt when mum asks if I would like to try some other styles, ‘like what’ I asked and from nowhere she produces a mini skirt and tells me to be careful not show the world my assets. It was just a short straight denim skirt, but it did ride up at times making for a different sort or care needed too the long skirt, but after a few mishaps I pretty much had it under control, but there was a question about where it came from, mum would never have bought this for herself, at least I had never seen her wear it, had she got it specially for me?
Wednesday, I have only one session in the morning so get to spend most of the day free. I got home for lunch and found mum’s note alongside a couple of round soft jelly like balls. ‘Try these in your bra, see how they look and feel. Mum.’ I played with the latex blobs for a bit, and then went to do as she asked. The initial feeling was cold and damp, but that passed and I was left with two tits bouncing around on my chest in a most unfamiliar way. Now as I was undressed and in the bra I felt I might as well carry on and went into my mother’s room and had a look through her wardrobe thinking that she would not mind now. It was a warm day and choose a lemon cotton dress that had its waist just below the bra line and felt light and cool as is wafted around my body, then with my make up applied and heels on I settled down to some studying.
I was deep in reading when the bell rang at the door, I hesitated about answering and sneaked a look through the curtain, a delivery van with a package, so I steeled my courage and went to answer, he looked at me smiled and asked me to sign for the package, then left, and I had been frightened he would say something, but it was as if he did not care, maybe he sees people like me everyday I thought.
‘Getting into this?’ was a surprise question as mum walked in behind me later in the day.
‘Just practicing’ I replied
Then she came over and gave me a kiss, ‘It is nice to see you like this, you are more relaxed and easier to get on with than usual’ then she dropped the stunner ‘And you don’t need to hide the fact you are looking through my clothes now, do you?’
I went bright red, she knew about my nosying times, what an embarrassment.
We chatted over our meal about how I felt, then later in the evening took me out to a pub she felt we would not be recognised in, but it had to be while I was still in the dress, so I got used to being outside she insisted. But not before I had depilated my arms and legs because a woman in a dress does not have hairy skin. It was worth it just for the closer feel of fabrics next to my skin. Wonderful.
But that was not the end to the days surprises, the package contained a thing she called a gaff, designed to keep my male parts looking female and flat down below, I asked why and she pointed out how I had a little bump at times and if I were to get excited it would become a big give away bump.
Thursday, I have several preparations to do, moisturise with a tanning lotion, file me nails neat, let mum ‘tidy’ my eye brows, try on the gaff.
Friday, Mark noticed the eyebrows, we had not really had a gaming session in ages and he invited me round that evening, adding that he would like me to go in a skirt so he can get used to me before Saturdays big moment.
I went round wearing the denim mini, white heels, fitted blouse, make up and a smile. I was greeted with a wow you look the part, we chatted about what I had done to myself for this effect then went onto the X box.
Mrs Jones came home a while later and just stood looking at me ‘Oh my god, look at you now, Mark this is now way to entertain a girl’ he defended himself saying it was agreed before and his girl would like gaming anyway. No excuse she said with a certain authoritarian tone, asked me to help make the tea, and told us we should go for a walk with the dog after.
We did as we were told and took the dog out and I discovered that 4” heels are not the best shoes for walking on soft ground in, besides needing to clean the shoes, my ankles were killing me, what was even better this was a local walk and though we walked past people and a couple said hello to Mark, no one seemed to know who I was.
When we got back my mother was at Mark’s drinking wine and setting out a timetable for our Saturday. They would get us to the party for seven so worked back going through everything we would need to get done before then. From their good mood we could tell they were enjoying themselves.
Saturday. I wore the silk cargo pants, which now felt delicious on my bare skin, I wore the lower courts and mum said she had a treat for me once I was ready. That treat was to take me shopping first for the groceries then onto a department store where she lead me to the lingerie section informing me a bride will always have a special set of undies for her big day. I walked out with matching white satin bra and pants along with two pairs of white stockings, the corset she was confident had tabs to hold them.
We had lunch out then headed home.
I had my last moisturising session and liked how my white skin had got a healthier colour, and then mum started on the beauty treatments. First she washed my hair, but as she was running some liquid through my hair she spoke as if to herself ‘Maybe we should have discussed this, but it will look good, I know it will’ it seemed as though hair washing had become far more complicated than I ever thought possible. In the end I asked what had she doing. She had given my hair a good wash, next she bleached some streaks into it, finishing of with a setting lotion so it holds its style better when we finish. When I asked if it was necessary she just said yes. Soon I had my curled streaked hair arranged on my head and looking nothing like it used to. Next she took my hands and first glued long nails to my fingers, then painted them a pink colour followed by doing the same to my toes, after three coats she was satisfied they looked good. Now I was to get into my new underwear and discovered the limitations of long nails, but mum helped me when she saw me struggling, it was as the second stocking was easing its way up my leg I thought ‘How odd for a son to be so comfortable with his mum while letting her fasten the tabs to his stocking tops’ that all done I was handed me the silk wrap and told it was time to eat. She was asking me how I felt again and I was trying to be honest telling her how nice the clothes felt, the feeling of being pretty and attractive, and the attention I was getting, also the bonding between us that had happened in the last week or more. She confirmed that she had enjoyed this time together, liked the challenge, and enjoyed my new personality as I became more relaxed and feminine. We hugged and thanked each other for the special time it turned into.
But we had to finish me off, first make up, mum did it this time so it was perfect, then it was into the dress, as she fastened up the endless tiny buttons that ran from my neck to the small of my back I realised I would never get it off alone. I stepped into my heels and fluffed the skirt out feeling quite special as I stood there thinking how great brides must feel on their real wedding day when they look and feel this good. Mum had some finishing touches, a fine gold necklace, her gold watch on one wrist a gold bracelet on the other, then with care she hung a gold chandelier from each ear and finally took off her engagement ring and slid it onto my third finger. I was declared ready when she had dabbed scent on me and it was off to wait for my groom to call.
Mark turned up with his mother, he had had an equally image altering day, gone the scruffy lad, in walked a smart man, neat hair, close shaved, and looking immaculate in the morning suit. Mrs Jones was looking rather dew eyed especially after she saw me, mum had warned me that seeing the both of us dressed might bring back happy memories for her and I was not to worry, she was going to spend the night with her and make sure she was alright. I got a fantastic hug off her and told I was beautiful and fit for her boy. Mark by contrast looked a little awkward and shy, maybe the clothes maybe the situation. As a last touch Mrs Jones pinned a carnation to Mark’s lapel, presented me with a posy of pink roses and out of her bag brought out the veil. I was told to sit for a minute while they fitted it with the combs to my hair; it was down to my arse at the back but to my shoulders at the front. Mrs Jones then said ‘Nearly complete. Mark’ he stepped forward looking more sheepish, took my left hand and pushed a gold band up to the diamond ring.
It was my mum who spoke, ‘I now pronounce you man and wife, you may kiss the bride.’
‘Mum!’ was all I could manage, but Mark had been primed for this little scene as he leaned forward lifted the gauze before my face and gently kissed my lips. For some reason I said thank you and kissed him back as he pulled away.
‘Sweet’ my mum commented and then took photos of us, even a family shot with the mums on it. Then it was a short walk to the car and off to Samantha’s house and the party. The car was a challenge; mum had to help me in with my dress, and make sure I did not sit on the veil, Mark had it easier and took of his top hat and tails for an easy ride.
Mark was still nervous and let me know he was not sure how this costume would go down, Samantha knew what we were doing but he still wondered what the rest of our circle of friends would make of a wedding couple, especially one like us. I told him to relax and put a girlie hand on his knee, if anyone was going to get into bother it would be me as I had got rather to convincing and I was not sure how many knew besides Samantha.
We arrived at Samantha’s rather large house and let Mark help me from the car, arranging the dress then lifting the hem to keep it of the pavement as I walked to the door. We were greeted by a rather lovely Tudor couple who on closer inspection was Samantha and her boyfriend, ‘Mark how lovely to see you’ he got an air kiss ‘and your bride’ she came to kiss me then repeated Mrs Jones words ‘Oh my god, Jens it is you, brilliant, don’t tell anyone lets see who works it out’ she pulled the veil over my head and kissed me, her boyfriend knowing the truth was a little less affectionate in his greeting but smiled all the same.
I linked my arm into Mark’s ‘Come on hubby, time we mingled and got a drink’. The night was far more fun than either of us expected, neither of us were great party people preferring our games up until then, but Mark got chatting easily with some of the other lads there, while I was picked up by the girls who at first did not know me, but one by one recognised me, mainly from my voice it seemed and then it was the oh my god scene all over again. Samantha had us play silly parlour games, and I drank more than I should, Mark as the driver had his limit and stopped, what a thoughtful partner I have I told him and gave him a quick kiss, to which he said ‘Not here’ my reply being ‘Where then?’ as I slipped my arm into his elbow playing the girlfriend part for all it’s worth. ‘Just not where everyone can see, all right’ he said in a strong whisper. ‘So later then, when we alone and you can have your wicked way with me?’ he was blushing, ‘That’s not what I mean, just not here, I am getting enough comments about you being the best looking girl here and are we a real couple, that sort of thing, so don’t reinforce the misconceptions will you’ I had one last teasing comment ‘What misconceptions, darling’ leant over and kissed his lips. He went so red it was unbelievable and I made a quick retreat to the food table.
As I said the party was much better than I expected, laughing and joking with both sexes, but it was later that as couples paired off for their private intimacies that we were left with the singles who were trying to chat up some one who did not want to be seen with the others, which left us rather at a loss, so we called it a night thanked our host and made our way back home.
Mark revealed a text from his mother, telling us that my mum was spending the night at Mark’s so we would not need to worry about disturbing them when we got home late, and that Mark should sleep at my house.
It was on the table that we recognised a set up, a bottle of champagne and a wedding card addressed to us, Mr Mark and Ms Jenny Jones that is, with a message saying ‘Lovebirds. Enjoy your wedding night. Xxxx’ I was reading as Mark poured the bubbly into two flutes, ‘Well Mrs Jenny Jones, how does that sound to you’
‘Funny, I can’t believe how much ours mums are playing along with this.’ As we sat together on the sofa drinking our champagne I explained some of what I had told my mother about feeling comfortable in skirts, then it was Mark’s turn for a confession, some time ago he had admitted to his mother that his lack of girlfriends was down to him being gay, he was not sure he meant it, but it did stop her suggesting he find a nice girl. And now this scene of me cuddled up, head on his shoulder with his protective arm around me, at some time we realised we had been set up to see if Mark was gay and how I would deal with dressing for real not just poking around in a wardrobe.
‘Well they got you right didn’t they, just look at you, the most beautiful girl there tonight, and if you get the voice no one would have known, I bet you’
I got up so I could refill our glasses, and as I crouched before him asked ‘And what of you, do you fancy boys or girls?’
Reaching out he caught my hand and pulled me onto his lap, ‘I fancy something else I have now discovered, and I fancy boys who look like girls’
‘So can I kiss you now without being told off?’
He did not give a verbal answer, rather he pulled my face towards his and gave me a proper kiss that left me in no doubt he fancied me. What a shame we were so self conscious at the party, we could have danced and kissed and done so much more at the party if only we had had the nerve too.
I have never had a boyfriend before and Mark has not had a proper girlfriend before so we enjoying the new sensations of intimacy, then as the wine disappeared I suggested I should take the dress off and go to bed, making it clear I needed his help with the buttons. At the top of the stairs my door was shut, but mothers open and my nightie draped on the bed, I was not sure that a mother should be leading a son into these situations but giddy from the bubbles I led Mark into the room and asked him to undress me. It was as I hung the dress up the Mark whistled, he had a full view of my satin undies and stockings, ‘Still gorgeous’ he declared,
‘Glad you like it Mr Jones’ as I started to unfasten his shirt.
‘And the nightie?’ he asked
‘Mine’
‘You are taking this serious’
‘Mother suggested it’
‘I like your mother’
I put a finger under his chin and gave a mock pout, ‘I thought you liked me?’ then as his trousers fell and his erection sprang free, ‘You do like me I see’
He blushed as we rolled onto the bed and continued our intimate learning. His erection kept on touching me and at times he would press it against me, until I was so high I borrowed under the covers and kissed it, nervously at first to get a feel and a taste, but then more confidently until I had the whole tip in my mouth and sliding my lips up and down its length. There were a few short thrusts and a moan just before I got a mouthful of semen and I knew that was him done. After licking it clean I tucked it back inside the boxers and returned to the pillow, ‘I think you enjoyed that’
‘I love you’ was all he managed, he was drained. However I still needed to clean my face and finish undressing before slipping into my nightie then slipping between the sheets next to my lover.
Sunday. The day after, I woke to sound of mum downstairs. I found her drinking a coffee reading the paper, ‘Good night I take it’
‘Definitely different, thanks for everything, still not sure why though’
‘I take it Mark knows about the nightie then’
‘Yes thank you, did you really mean for all that to happen?’
As I sat down with my coffee she looked at me, ‘You might never do this again, I wanted to give you as much of the female experience as possible, and sleeping with a man is one of them’
‘How long have you been planning this?’ I asked
‘Me only since the idea was suggested, Emma I think was looking for an opportunity for months now. Anyway, I think my questions about your cross dressing have been answered in that I have a pretty son sat in a lovely nightie opposite me, what of Mark, is he gay do you think?’
‘I don’t know if he fancies me as Jens, but as Jenny we had some new experiences together’
Mark came down in my towelling robe he found behind the bathroom door, and looking rather subdued when he saw mum, ‘Morning Mark, good night?’
‘Yes thanks Mrs Christen’
‘There is a bag of clothes Emma sent round for you to go home in, help yourself to coffee and toast’
Mark made a quick exit, changing and leaving, I tried to kiss him but it was only a quick one and he was gone.
‘He will need time to sort his head out’ mum comforted ‘it is not everyday you wake up to find your best friend in a nightie after wearing what you did yesterday. You ok sweetheart?’
‘Fine’
‘Well that was your end of year party really wasn’t it, so what do you fancy doing today, you could go and play on Mark’s X box or we could go shopping and get you some new clothes, that nightie for one needs a wash every now and then, and though I like the idea of you thinking my clothes are good, I think we ought to get you some of your own if this is going to continue. What is it to be?’
I went over and hugged her ‘You are the best I cried into her shoulder, I would love to go shopping, but it is no longer for a party so what if someone questions me, what do I say?’
‘Just tell them the truth, that you are a trans sexual and your true nature is female’
I mean who would have predicted my mother knew I was playing with her clothes, that she would encourage me to walk about the house in heels and a skirt, that she would take me out dressed as a girl and buy me alcohol, that she would set me up with my best friend so that we end up in bed together, finishing off the adventure with my first sexual encounter.
The summer holiday was alot different to what I had expected it to be. First of all the end of term party had been something of a revelation, I mean who would have predicted my mother knew I was playing with her clothes, that she would encourage me to walk about the house in heels and a skirt, that she would take me out dressed as a girl and buy me alcohol, that she would set me up with my best friend so that we end up in bed together, finishing off the adventure with my first sexual encounter. Though I was doubtful about my mother's motives at first, about my own feelings and about Mark's reaction, I have to say what my mother has encouraged me to do has opened up new doors and I am loving every one of them.
I had set up a summer job before term ended so spent alot of time selling ice creams from a kiosk in a local park, but when I was not selling i was home trying out new feminine touches to my appearance. No one had made much of my ear peircings, some friends who saw me after the party told me the streaks were unusual but looked good in an off the wall way, but what I wanted was for my hair to grow a bit longer and get a really nice cut, but I dare not say that to friends who think I am only into games. The summer did allow me go out with my mother on occasion as Jenny, when she would buy me clothes and make up further encouraging me to be her girl, which could be unnerving at times, other times were really good as we grew closer and better able to talk. Mark was still the gaming friend he had always been, but something had changed in the relationship. There was a day mid week when we were both at home and having bored of our game sat back drinking a lager each in the sunshine. Mark was working up to asking something, and ended up blurting out that he wanted to take Jenny out. I was not ready for such a direct request, but once I had made sure he was genuine I offered to go and change, he should call round in a while.
I was always half ready to dress as I was clear skined and hair well groomed, so i only needed to apply make up, change my clothes and style my hair to be pretty much reasonable. I choose the denim mini and a loose silk top which exposed the bra straps. Mark came round and let me know he approved by giving me a kiss. Not sure what to do next I let him take the lead, soon we were cuddling on the settee like a proper couple, but before my mother came home i made sure my face was repaired and the preparations for tea were well underway. When she came home and found me dressed and Mark watching the tv, she invited him to stay and invited his mother round as well.
Mrs Jones was a little off gaurd when she saw me dressed, but recovered quickly to give me a greeting hug and kiss then let me get on with the meal. Our mothers just chatted as though it was normal to have a son dressed as a daughter making their meal for them. In the end I served the meal before sitting down to join them, rather like my mother would have done in the past. We all drank too much wine and I relaxed enough to let Mark kiss me when he left. I knew my mother would see but the expected questions never came, just a compliment on how good I was looking.
Mark and I once tried kissing when I was not in full Jenny mode, we were alone and sat next to each other when we moved to get up and lost balance so we were on top of each other, I went to kiss Mark but he pulled away as soon as I touched. I apologised and said it was spur of the moment thing, then he tried to explain how he finds girls and not boys attractive, and how he has not really come to understand why Jenny is attractive, even though he knows I am a boy. I confessed to being confused as well, that I like being Jenny and to have Mark treat me as a girl and react to me as he does is a mystery, but a very nice mystery.
And so our eight week holiday slipped by, a lot of work and money saved, but also a growing wardrobe and the odd liaison with Mark, mostly at home on the settee, but a couple of times out in the big wide world when we thought no one would catch us.
The return to college caused my life to change, weekdays were spent studying as it was going to be a hard last year, then working either Saturday or Sunday at the park, which only left one day free which was spent doing a variety of things like college activities, going out with mother or just being busy doing nothing, well everyone needs a rest sometime. Then when I was off, Mark was often working or having to catch up on the studies, so Jenny did not get out much at this time, I could sleep in female sleepwear but getting myself fully dressed was too much effort just to sit around at home for a couple of hours while I studied. I was persuaded once by mother to join her on a shopping trip as Jenny followed by an evening with Mark going to the pictures and having a pizza after, clearly we had our girl/boy friend moments but nothing too heavy. At the end of the evening Mark asked if I would be Jenny for him at least once a week because he enjoyed my company in a differnet way to when I was Jens which was still happening at college and at home when we found time to play our games. It did not take much persuasion for me to agree to being Jenny at least one evening at the weekend, this decision was followed by a poster going up at college the following day advertising a halowen dance.
Mark did comment on it and picked up a flyer, but I was more cautious we had done it once and had fun but what were the chances of doing it again and not attracting cruel comments. I told him to forget it. That was until about a week later, it takes that time for Mark to put his clothes in the wash, his mother to find the flyer, and for my mother to receive the flyer from Emma, finally catching me and asking if I was thinking of going and what was I going to dress up as. I tried very hard to explain how I thought it was not a good idea to do a fancy dress with Mark again knowing both she and Mark would want me to go as a female partner to Mark's male. In the end I was beaten into submission when later that day Mark came round to play a game and his mum came round for a gossip with my mum. It did not take long for the subject to come up and even though it was me who would be doing the main dressing up it was decided that on a democratic vote ot 3 to 1 I lost, they had even discussed the outfits and Addams family had won. It did not need great intellegence to know that Mark would get to be Gomez while I would be Morticia. My mum had not really seen any of the films and everyone else had been younger when it was last out but Mark had a CD and nipped home to get it so we could all sat down that evening to watch what we would be imitating. The story clearly was not what we were watching and as the characters appeared we, well more they, spoke of what we might be able to achieve. Mark fancied a velvet smoking jacket look, while Morticia always seemed to be in long, tight black dresses that gave her great trouble moving around. I dreaded to think how this would turn out, but I knew I was getting steam rollered into it so might as well go with it and enjoy what I can.
Within days mum was round to the costume shop and had booked a dress she knew would be ideal, and with a week before the dance she was making plans on my behalf, black stiletoes, dark burgundy nail polish and lipstick she had wanted black but I wanted some colour and not just the blushing of my cheeks, I had black underwear so thought that would be it. On the Friday she came home with the dress and asked me to try it on, it was close fitting but stretched enough to allow movement, but the bit mum liked was the way the skirt flared out below the knees, the way my knees were kept together causing we to swivel as I walked made the hem spin out and exagerate the swivelling that my hips and knees were doing, added to that the heels affected my walk, I was just going to mince everywhere. The sleeves were another thing as well, huge frilly cuffs which started at the elbow and finished below my fingers. This costume was going to take some getting used too.
The hours at the park were getting less as the evenings got darker so I was home early which pleased mum, she had been shopping for bits she said. I recognised the false nails but there were others I was not familiar with but did not have time to look at carefully before mum suggested she helps me get ready, with a hair session first. While she washed, conditioned and rinsed my hair I did the nails when not leaning over the shower, then as she styled my hair I painted them. sometimes I am thick and dont see things coming, this was one of those times, I got up to go and dress when I caught sight of myself in a mirror, my hair was jet black. Mum must have noticed my shock and reassured me it was not a permanent colour and will wash out after a few goes. In my underwear she then applies my face, quite pale skin, burgundy lips and dark eyes with the added extra of false eye lashes making the eye look even bigger. Followed by black stockings and the dress which between us we manage to wriggle me into with her pulling the zipper up, securing me into my most limiting outfit ever. She had even got me a black cape to keep me warm, then with a squirt of perfume I was ready. It was about this time I noticed that mum was wearing a rather nice new fashionable dress that I had not seen before, I complimented her on it and asked if she was going somewhere special, just out with Emma and some friends she replied, that will be nice I told her, she then felt the need to justify her getting dolled up and going out which she had not really done since dad died. Seeing me wearing nice clothes and enjoying myself being pretty had encouraged her to do the same, and the invite they had to go out that evening seemed ideal, ending with if we I can go out looking great and have some fun why can't she, why not indeed, was the ony response I could think of.
Mark had borrowed his mother's car and parked close to the door, but it was seeing him in the velvet jacket, black trousers, white shirt, red cummerbund and slicked back hair that got my attention, that and the Gomez style greeting of arm for me to link and formal greetings, once in the car he let out a whistle 'Did not like to say in front of your mum, but you are hot tonight' I squeezed his thigh and told him he was pretty hot himself.
We parked and the first person we saw was Samantha who let out a delighted squeal and came over to hug me, she and her new boyfriend were vampires, only she had the long black spike heel boots, tight black top and a riding crop which said something different, Paul just looked compliant as he wore an ill fitting black suit and fangs, I later discussed with Mark his chances of being long term and we agreed he stood no chance unless he liked the riding crop and doing as he is told. I walked in with Samantha linking arms like girlfriends and giggling as we tottered in on our heels. That was a great start to a fun evening, lots of people did not recognise us, even Mark's costume changed his appearance enough so that only close friends made him out, a few like Samantha knew me and for some reason none of them spread it about that I was really Jens, but spent the evening calling me Morticia or Jenny, so when I was with Mark I could use him as support and link his arm as I minced along by his side, when alone he was even brave enough to show some of the affection we had kept to our private times, gradually getting used to each other and the other party goers so that we even had a few dances, though I had to make them slow ones. But the close contact was not missed by Samantha and Clare who were treating me more like a girl than I was used too.
Though the dance had opened us up to new experiences of being a couple in public and for me being Jenny in a more convincing role, it was later on that our relationship moved on. I invited Mark in when we got home asking him that I would need help getting out of the dress. Once again my mother had set us up, a note to Mr and Ms Jones-Addams, Hope you had a good night, stopping at Emma's, see you in the morning. It was leaning against a bottle of vodka mix. So we opened the bottle and settled back for a drink and nice cuddle. Things moved along very nicely, mum was round at her friends again so we had the house to ourselves, and with a note similiar to the wedding dress night I knew she had set this up. After a good session on the settee I mentioned that I would need help unzipping the dress, so picked up my glass and the bottle and minced upstairs followed by an eager Mark. If boys are ever considered to be on heat like dogs, then that night I must have been, he was keen and obvious what he was hoping for. Again my mother had left her door open with a nightie draped across her double bed, he undid the fastener and helped me to wriggle out of my second skin, then we undressed Mark and fell into bed for more passionate cuddling. I was about to blow him off again when he tells me he wants to give this time not just recieve, puzzled I ask what he means, now it was his turn to look puzzled, he had seen a tube of KY jelly on the bedside and guessed I had put it there, not me must be my mother setting us up some more, so I asked what he had in mind, and soon we had worked out the basics of how Mark could make love to me and I feel him inside me making me feel the way I looked, feminine. He erupted inside me, then sadly he shrank away leaving me wanting to feel him inside me still. I knew then I would be wanting his attentions again and soon. But not that night, neither of us knew how a man can get erect again, so we cuddled until sleep took us.
The morning found me looking a mess, as well as the pillow, I had not cleaned up so make up was everywhere, it took a while to get clean and presentable, but when I finally made it to the kitchen found Mum and Mark eating toast and chatting about the evening. Mark left after breakfast and a good kiss form me to say thank you. Then it was just me and mum, I thanked her for the card and drink, and the use of her bed, fine she said just wanting to open up new experiences for me, which made me think of the KY jelly, so I thanked her for leaving it out. This rather caught her out, the jelly was for her she had not meant to leave it out, now it was my turn to be embarrassed as she rightly guessed what we had used it for and asked how it was, maybe I was feeling a closeness but whatever the reason I told her how nice it had felt, and she hugged me telling me how lucky I am to enjoy such things, then I told her I was getting really confused over my identity and did not know if I was a boy or a girl, she just told me to be myself.
Then it was time for her confession, the night out she had had with Emma was more than just the two of them, it was actually four of them, Jack and Sean being the other two, and yes they had had an enjoyable evening, it was the first time she had been out on a 'date' since dad had gone so it was never going to be much, I was fine with that as long as I did not have to call her man 'dad' and he was good for her then I would be fine with it. Then came the bigger confession, the topic of where we, Mark and I, were the night before came up, they said a fancy dress dance as Morticia and Gomez, and somehow they assumed I was a daughter and not Jens dressed up as Morticia. She reassured me that if she saw them again she would correct them but it had been fun letting them think I was a daughter.
The Sunday was going to be a quiet day, but as I was still glued to my breasts and nails I dressed in my mini kilt and pink angora top before settling down to do some course work. Just before lunch mum came in and told me she was going out with Emma, and she was looking good again so it was not just for a gossipping chat. This was followed by Mark texting asking if I would like to go round to his. As soon as mum and Emma were gone, I was round at Mark's and kissing for all I was worth, I had the jelly in my bag and had already squeezed some inside my hole in anticipation. It took us no time at all to be on a bed with my knickers down and my legs up with Mark filling me, this time I was sober and tighter, but Mark lasted better but still came without me, though he did touch what I guessed to be a g spot several times and wished I could have done more to get him to stay in there till I enjoyed these new sensations.
The second event in what I expected to be a quiet day was to find myself meeting Jack and Sean, I was watching tv with Mark after our sex adventure when I had a text off mum asking me to be scarse or be Jenny. I was already Jenny so stuck around to see what was happening. The four of them came back mid afternoon having spent their lunch in a pub, seemingly mother had not managed to tell the truth, and I could see why, both men were good looking and seemed to be good fun, Jack being well over six foot and toned why would she risk losing him when they were just being friends by admiting to a lie. I immediately realised that if I was to ever meet these men again it have to be as Jenny, mum was not going to spoil her fun by admiting the lie, it also meant she could ask me to dress, and it also meant I had another little excuse to make myself pretty.
Later at home I questioned whether she had explained to Jack that her daughter was really a son, with a hug she asked if I was sure about that. Going on to tell me how she liked Jenny, Mark clearly liked having Jenny around, and now Jack and Sean would be expecting see Jenny if they meet me again. My life as Jens was being restricted but also encouraged by those close to me, and deep inside I could not find the fight to say no, I knew that I was enjoying the whole experience far to much to stop it right then.
Life was getting very interesting, I had a boyfriend, a supportive mother and a desire to be a girl, but a caution about giving up my birth gender.
Life through the rest of the year was pretty much one of, Jens for college, Jenny for most of the other times. After our heart to heart after the halloween dance mum offered to treat me to a hairstyling that would allow me to switch easily between genders, so when I came home I would only need to change and add light make up to feel right. They also took away the black and dyed my hair a more natural light brown.
Christmas came and I got lots of Jenny gifts off all those who knew. We had a big dinner with Jack and Sean turning up to make it a busy day. Of course I had a lovely new dress for the day, dark red stiff cotton with new red spike sandals off mum, 3" chain ear rings off Emma and a set of silk underwear off Mark, which he gave me in private to save my blushes.
I had grown more confident about my presentation as Jenny so for new year I went with Mark into town to join in the celebrations as a girl. My eighteenth birthday came next, I could drink legally but my ID card proving my age was not very flattering even though I tried to let my hair look girly, it was still going to be hard not to be questioned over who it was on the card when I was Jenny. Mum got over this by using the ID maker at work and generating a new one identical to the student card except in the gender it was female and in the photo it was a fully made up Jenny.
Mark was still keen on our dates and as my job disappeared in the winter, he was able to persuade me to go out more often if he was paying, this was not a problem as mum had virtually got me to be Jenny every weekend since the turn of the year. As easter came we both put our heads down to get our best grades, Mark suggesting as a reward when we were finished we go away for a weekend, our mother's on hearing this suggested a nice city break and they would pay for it. Exams over and summer jobs not started we had our cases loaded into Mrs Jones' car and we were off on our first holiday without parents, but the fuss my mother made about what I packed made me think she was taking too much interest. It was summer so she had me use tanning creams on my body, then sent me for a trip to the hairdresser for a trim, then she had me do the long nails and fix my chest, which only left the packing. Long ago I had learnt how to hide my male member with glue and tape, so now I could wear pretty knickers of any design, but she had thongs in mind for my time away, she also fastened me into a new corset she had treated me too, then I was allowed to choose my clothes as long as she approved. You would have thought Mark was picking for me and not my own mother. Once packed and dressed in nothing but skimpy, light or revealing outfits, I was allowed to go. Then when we arrived in York at the hotel and unpacked I found a fresh tube of lubricant and a pack of tampax, she really was setting me up for a weekend of passion, but I was not going to object, it had been weeks since the last opportunity to have my hole filled.
Mark took his chances and asked if I wanted help changing before we went to look for somewhere to eat, when he found that I was only in a corset and thong under my cotton wrap over dress, he took it to mean I was randy, soon he had me over the side of the bed while he pushed into me till he could last no longer and came in a heaving rush. While he recovered I dressed in my christmas dress, smart but short enough to please him was the idea, and it worked. We had a nice pasta meal and a walk around a few bars, before heading back for round two. Only this time he was not fully recovered and I was relaxed more, so as he touched my excitable spots I became more keen to get him to push against those spots, eventually I had my first orgasm, I had masturbated as a boy but this was totally different and far more satisfying, then Mark came. He asked what had happened to me. I told what had happened is what I want to happen every time, I might allow him a quick shag but what I wanted was a long slow fuck that made me come. And bless him he said he would try.
We had Saturday sight seeing, followed by a evening of trying to satisfy me but failing. Then on the Sunday more sight seeing followed by a new approach, while getting ready to go out for a meal I knelt in front of him and sucked him off, my reasoning being, I liked having him totally at my whim, I liked the taste and lastly it would slow him down later. It worked so well I came well before him and was able to enjoy relaxing as he pumped away at my arse. I had never had sex as a boy but I doubted it could be better than this. I was filled with cum and happiness, what a post exam experience.
We arrived home on the Monday afternoon and had time to recover from the drive before our mother's got home and wanted to know how our break had been. We ate together and chatted about our weekends, Sean and Jack had been around but we were not brave enough to ask if they had stopped for the nights as we were not there to hinder any night time activities. It was when Mark and Emma left that my mother came out with it. 'You have lost your virginity properly now, haven't you' I was at a lose at to what I should say, mother's I thought kept off such topics, but I blushed 'thought so, you seem more confident with your touching and your smile tells me something special happened, I made up the rest........am I right' I hugged her and told her I was in love, that Mark was so kind and considerate I could think of no one else I would want to be with. She hugged me back and told she was pleased for me. Next she asked if I had thought what I was going to do next, get a job, go to uni, do some job training. I had not really thought that far ahead and just wanted a break from studying.
Until the results came out I picked up my old job selling at the kiosk, so I was back to being Jens a lot of the time, except my hair was now a swept back bob that had a feminine feel to it, and did not go unnoticed as a camp look. The results came, Mark got great results and was accepted onto the course he wanted, for me it was not so easy, my results were poor, maybe all the gender confusion had taken its toll on my studies, whatever, I could not do the course I wanted or anything like it at any of the unis I preferred so I had to consider getting a proper job.
It was on a Sunday afternoon, I had been at home since I finished work on the Saturday, had got dressed for a night out with Mark and was now flicking through the local newspapers and college brochures in what might be called Jenny's morning look, tits still in place, nightie and silk wrap. I was admiring my pink nails which I had now grown a bit so they had a nice oval shape but were not too long, when mum comes in and asks if I have found anything I will apply for, I point out a few trainee jobs, but then mum picked up a college leaflet, I had not done it deliberately but it was just on top so mum thought it significant. The course was for a one year hair and beauty foundation training, with options to take the training further in future years. Mum seized on it saying it would be a great asset, Jens as a boy would be able to do the course and see it from a different perspective, male hair dressers are always the best she convinced me, and as a secondary result my time as Jenny would improve with a greater knowledge. I promised to enquire on the Monday. When they said they had places and no objections to a male being on the course, I was unexpectedly pleased that I had a way forward that could leave me with many options and oppurtunities, though I would be expected to participate fully in all aspects of the course, there was nothing that should prevent me from completing and passing the course work and final exam. I also rang some of the trainee jobs but I was either to well qualified with my A levels or not qualified enough having not got a degree. What clinched my decision was that mum offered to pay for the course fees and give me an allowance if I failed to pick up a part time job, she just explained how much Mark was going to cost Emma and if I had gone to uni she would have had to find that money from somewhere or see me go into debt. All I had to do was sign up and wait to see what my classmates and tutors would make of me.
Two weeks later I found out, I was the only boy among twenty one teenage girls, all who had made a special effort to get themselves dolled up for the first day, seemingly competing to show how much make up they could use. Myself I had chosen to wear smart jeans a nice Jens jumper which made me feel rather drab, but I was a boy in this situation and not Jenny so I settled for my boy look. The first week was finding our feet, where places are, what topics we need to study, who our fellow students are, which was interesting as I got different reactions from the girls, some saw me as an intruder others an interesting novelty. The comment that stuck me most was a tutor who explained how, when we were doing practical sessions we would be taking it in turns to be the model, because we need to know how it feels to have all the treatments done to ourselves so we can explain better to customers what is happening, and rather pointedly I was told I was to take my turn regardless of the treatment being practised. Unknown to both her and myself this instruction was to have profound effect on my life, let me explain.
Three weeks later we had been doing lots of listening to tutors doing the theory of the course, then we began to use the equipment that the college had for training, our first practical was washing and conditioning hair, we had done the theory of why and how this worked and is good for hair, now we were told to pair off and wash each others hair. I paired with Kim and washed hers, then she washed mine, followed with blow drying each others as we clearly would not want to be leaving with wet hair. Kim had long wavy hair that had got more curl from the wash, so I just dried it with a volumizer to give it body. Next she dried mine which was at the time a sort of bob cut that stopped short of my shoulders, as Jens I would sweep the fringe hair over the top without a parting, but Kim dried it with a parting so the fringe came across my face leading it into the bob which now curled under. Some of the other girls had restyled their partners hair, but I was the most self conscious of those who had been restyled. It was when the tutor congratulated me on taking a full and active part in the session, I said I had every intention of learning as much as possible, good she replied I might remind you of what you just said later in the course if you refuse to participate. Kim then chipped in with her own comment that she would make sure I did not miss out on anything, and when I looked at ther she had a very cheeky smile on her face. I just said thanks with what I hoped was a wry grin on my face.
Mum was a little surprised to see the restyled hair when I got home but told me it looked nice, I told her it should as it was how I wore it as Jenny and the cut had been designed to be that way really. What she meant was it looked nice without me being Jenny and just being me.
My next practical of note was a manicure, the girls had all been told to come in with their nails clean, I just made sure all traces of my weekend activities were removed so as not to arouse suspicion. Again with Kim who had become a good friend by this time, removed cuticles, filed, polished and buffed each others nails, Kim had brought her own polish in but I used the clear offered. Kim did comment on how I kept my nails longer than her brothers did, I said I did not like them short and stubby, it stopped me chewing them. As we chatted future practicals came up and the one where we put acrylic nails onto each other made for interesting conversation, she had long nails and hoped not to have them put on her fingers as real long nails look better than acrylics, but I had short enough nails for the nails to make a dramtic effect. I tried to explain how it might look odd a boy having long nails, but my eagerness to learn statement was returned to me and I knew that with Kim as my partner I would not get away with the excuse of being a boy, besides I was sure one tutor in particular saw me as a challenge and did not want a boy on the course and used practicals to try and drive me off the course, I also felt a couple of the girls wanted me to fail and leave, it felt a bit like sex descrimination reversed.
As the year progessed, we worked through massaging hands and feet with oils and moisturisers, waxing which we only did on arms and I knew when it was coming so did not depilated for a month before so I had something like a boys arms to show. When I said I liked the feel of smooth arms I got some odd looks from a few girls, but stated that I might just keep them clear as they felt so nice, to which Kim asked if she could do my legs, Sally then offered to do my bikini line, I told them I would think about it and if I decided I needed help they would be the first to know. What they did not know was that my pubic hair was already trimmed back to take my thong, and there was no way they were going to wax me up there.
Towards christmas I noticed an advert for a Saturday girl at a salon, and feeling brave went in and asked if a Saturday boy would do, I told them about the course I was studying, and was told to start that weekend. This would be great experience and much needed cash so I was pleased with myself, as a bonus the manager was a man which made me feel a little more confident about being there. He was not quite the stereotype gay hairdresser but not far off, his hair was long and luxurious, and his clothes had a feminine look about them. I was only sweeping up, making drinks for customers and at times washing hair, nothing hard but it was a job. Over the weeks I got to like Ray and the other two stylists, they behaved like three girls not two girls and a man, so it was no surprise that with all my exposure to the girl students as well, I too became one of the girls at the salon imitating Ray, touching customers in a gentle feminine way, chatting about nothing, letting my vioce sing a little, and make gestures with my hands that when I caught myself recognised Ray in them. Besides which Ray was the first real gay man I had meet properly, I found this out on my very first day at work, as we were closing up a man came in, very muscular, tanned and in tight fitting clothes to show off his physique. I very nearly said we were closing when Ray came past me and greeted the man with a proper kiss. I was really shocked at this up front display, the other two stylists, Sara and Kate just laughed at me when they saw my reaction, which made me blush, and wish a hole would open up below me. How embarrassing. Needless to say I was not so shocked next time, and as my demeanour became more feminine at work Sara jokingly asked if Ray could set me up with a date, when I said I did not need a date they asked if I already had one, I said yes, then as a joke I think they asked 'Is he nice?' I stumbled over my answer and stammered, which got a clap of Sara, and of Kate 'Excellent, another fairy like you Ray' I was getting truly embarrassed and upset at being teased like this, so it stopped and Sara gave me hug and told me they meant nothing by it, I had a long way to go before I was anything like Ray and some of his friends.
Christmas was a special time, no college, just dressing down for work but I could keep myself feminine if I wanted, I bought myself a pair of tight hipster jeans and a long sleeve T shirt similiar to what Ray wore, and felt at home wearing them to work. Of course Mark being home for more than just a weekend meant we had some catching up to do, he was enjoying his course, making new friends and getting into the student way of life, I told him about my life, the course and the job and the incidents that happened and laughed at the times I was nearly found out, but most of all I loved being with him, having sex again and being able to be his girlfriend was just so special.
The next term brought new challenges to my identity. We had a series of lessons on hair colouring, at the end we all knew we would be doing something to our partners and had to discuss with them what they would like doing, Kim said she would like to try an all over auburn colour, I was still unsure after my black hair experience, but I had the salon girls I could ask for advice from as well and they all felt I should try highlights. And so mid February Kim got a auburn head of hair one day, followed by me leaving the next with silver and gold highlights, the tutor was around to avert any disasters so it came out fine, and I unexpectedly liked it more than I thought I would, the texture of my hair seeming to have more life, so I promised Kim I would be more adventurous next time we have a chioce in a practical session.
For practice we were encouraged to use the college facilties outside lesson time, so myself and Kim plus a few others would spend Wednesday afternoon when we had no classes pampering each other. This usually meant manicures, pedicures, massages and hair styling. The girls would also make each other up, I did not join in with that but did Kim's make up on several occasions. The main benefit for me was the manicure, my nails became elegant but not long which was nice, and my hair was treated to several different styles though a bob cut is rather limiting compared to what I could do to Kim with her shoulder length locks.
I also started to wear more feminine tops to college, mostly the long sleeve T shirt style that fitted rather better than a boys would, plus my large shoulder bag I used to carry college work in, not to mention my more effeminate gait and gestures, I hardly could not believe it when Angie pointed out how gay I was behaving, and when I said sorry, they said what for I was just being me and I looked lovely the way I was. I gave her an air kiss and a hug, thanking her for being so nice. But it did rather let me lower my Jenny/Jens divisions. I nearly always wore hipster jeans and tops I had bought from the women's rail in stores, plus I stopped hiding my hairless arms, and started wearing nail gloss all the time. I was just feeling more myself like that rather than trying to be a college boy and dress scruffy.
Towards Easter we had classes on make up and fashion, I knew practicals would follow and worked out how to aviod being totally dressed up by Kim. After the holiday it came about and I managed to do Kim's make up but created a new challenge of what make up would work for a boy or man, we had plenty of fun experimenting with subtle shades until we had a barely noticed make up which just made my face look better with clear eyes and soft lips, no strong colours just shades. We thought it worked well and we got good marks but you could tell one of the tutors felt Kim should given me the full works.
Next we had to dress our partner differently to their usual style. Kim nearly always wore a mini or long top and footless tights, So I scoured the charity shops with her and found a pair of long black silk culots, and a big flouncy paisley top. For me, we found a short lemon kaftan top and white linen trousers. At the end of the week we had a fashion show where we all went out changed and came back to show the class our new look. Kim got a eight for hers, I got a seven, not bad we thought as we had not been able to fully accesorize the outfits. Some of the others felt the same and a new show was scheduled for the next week. We had the morning to fully prepare our partner, I gave Kim a big hair do, with eye shades picking out the paisley colours, lilac nails and lips also from the paisley, then stood her on a pair of light purple shoes she owned. She got a ten this time because she was stunning and so different to her norm. I was given a bob full of body and a fringe sweeping across one eye, which covered some of the make up she had used giving me darker eyes, paler skin and creamy lips, my nails had a slight pink tint but nothing noticable, and I wore some plain sandals on my feet. I got a nine, based on the use of different styles and that I did look good, but it was not that far removed from what I might be expected to wear. 'Make up and a girls hair style?' I questioned, and nearly to a girl they all said yes if I turned up with make up and styled hair it would not be a surprise, the lemon top was no real break with what they felt I wore already, just a slightly more camp top than usual.
When we had all been judged and marked, some did much better than Kim and myself had done, while others had not faired so well, the three tutors made general comments about what had been seen followed by a challenge that was going to affect me. It was Patricia, the tutor I felt had it in for me, who came up with a suggestion 'You have all done very well and we are all impressed with your work, but we notice that given the oppurtunity of having Jens in the group no one suggested possibly the biggest change of look' I had a good idea what was coming 'I was thinking someone might have dressed their partner as the opposite sex. So what we would like you to do is split the group in two and one from each group is restyled as a man or woman.' the pairs were all separated and we looked at each other no one volunteering in either group to be restyled, the girls were all girlie and having that stripped away would be more than they could take on board, for myself I worried I might give away my secret. With no progress Patricia intervened 'As no one is volunteering I would like to suggest Jens and Kim are the models. This will give us the chance to see how the genders are similiar or different, and the different challenges involved.' I looked at Kim she looked in shock, I was just feeling very nervous and worried how to handle the situation. 'The look we hope to see is nothing outrageous, something quite mainstream and positively cross gender' Kim was going to object when she continued 'And for Kim who I think will have the biggest challenge I will offer to take her for a full spa day to compensate for the shock she is now feeling' there was a wow from some of the other girls and Kim's smile crept back onto her face.
This decision brought about animation to the groups, most of the talking was done by the other ten girls in our respective groups, they were all trying to put forward their ideas. By the end of the session we were told to come back after the weekend and each person should have their ideas on paper and then try to put the best of them together. My more immediate problem was how would I deal with the after effects, how would my mum take it, probably well, my friends outside the course and work on the day after might be hard depending on what they actually did to me. I was right my mum had no problem with the thought of me being girl at college. The surprise was work, I mentioned what had been happening at college as I often did, they knew about my lemon top and linen trousers actually suggesting I come into work in them, and I was wearing them that day. So now I was telling them about the project to dress me as a girl, all three thought I would make a good girl if done well, and when I asked what I should do if they do something rather permanent and hard to cover up, like what they asked, I expected my hair to be coloured and restyled in some way, I also knew they would want to extend my nails. All three agreed that if I had long nails they would not be removed easily or if I had a style that would need another cut to return me to a boy look, then the only solution was for me to come into work as a girl. Then the stunning final statement from Kate 'We rather expected you to become more girlie already if truth be told, just enjoy the experience and we shall look forward meeting a new girl next week possibly' So that was it, no get out from anywhere it seemed, I could even go to work as a girl.
By the time Monday came around both Kim and me were very nervous as to what our teams would have come up with. Kim would not allow them to cut her hair, but they could shorten her nails. For me I could not think of anything I strongly rejected, my only request was that at the end I did not look like a freak, just a girl. There were a lot of ideas and it was decided to do two styles, one a student look, the other smart going out in the evening look. There was a college wardrobe that the drama courses used, plus the ever affordable charity shops to rummage through, and for me the offer of my teams own wardrobes. By Wednesday we had the styles sorted, college would be footless tights, short pea green pinafore (Siobhian's), 3" wedge sandals, tons of bangles and chunky bead necklace, Leah was in charge of make up, Suzy of hair and Emma had the nails to do. For the evening a red bias cut, one shoulder/diagonal hem dress was supplied by Suzy, red platforms, a white wrap, fine gold jewelery, a red clutch bag. Geri was to do my face, Sam would finish the nails and Alice would restyle my hair. I promised to be hair free and pick up my own underwear, I hoped I gave the impression I would need to buy some and not just look in my drawer for something suitable.
Come the Friday morning I was almost ready to accept whatever happened, but nervous about how it might affect me afterwards, I still had to go to work and finish the course, how would I do these if they did something extreme. I spent the morning with my college team. They told me to sit back and just let them do all the work. As I expected the nail trolley was wheeled over and Emma proceeded to fix full length acrylics painting them a pale green colour. Suzy gelled my hair and with small bows created and mass of tiny pony tails all over my crown. Leah then gave me a plain make up with no bright colours just a daytime style. Finally I was dressed. They loved my lace knickers, and had found some bra inserts to fit in my matching bra. I was finished and along with Kim who looked like a weedy lad in jeans, trainers and a sweat top, her hair hidden in a baseball cap, they had darkened her face to look less pretty, and cleaned her shorter nails of colour. We entered the main classroom to applause, Kim blushed I tried to look unsteady on the heels, no point in being to obvious. Then the tutors and class marked and commented on our appearance.
For Kim the next event was a shock, being lunchtime every one went to the cafe, she felt her credibility would be ruined if anyone saw her, especially her boyfriend. I tried to look nervous but told her I would do it if she did, and getting changed back just for a buttie and coffee, then having to change again would make things more long winded. We walked out of the building surrounded by our classmates, rather like we usually did any other lunch time. When it was noticed how easily I was walking, I replied that I did not know what all the fuss about heels was they were not that hard to walk in.
After a quick lunch my second team had me back in the training rooms. Alice did the full works on my hair, shampoo, conditioner, colour, then a cut. She would not let me see what she had done. Like wise Geri did my face, Leah had plucked a few eye brow hairs out in the morning, Geri now pulled more out, I did object but was told no girl had bushy brows. The only thing I could see was the red polish Sam was applying to my toe and finger nails. Then it was time to dress, I had brought red underwear, but they told me to only use the knickers, then they sprung a corset on me, I had to be strapless and this would give me a waist as well. They seemed to enjoy pulling the laces as tight as possible but I did finish up with a great figure, then it was on with the dress, short gold neck chain, gold bracelet and watch, long dangling gold chains hung from my ears. I was then allowed to see the mirror. I shall start with what they had done to my hair, my bob had gone, well nearly, at the front I still had the length and a fringe which parted in the centre, but the back had been trimmed right up the nape of my neck the longer outer layer of hair being nearly level with the top of my ears at the back coming forward in a diagonal line to the long hair infront of my ears, The short exposed hair was a darker colour than the lighter top and sides. That was not the end though, my eyebrows now had the tadpole shape the girls all seemed to like, below which my eyes had a smoky look, there was foundation and blusher but it was the full red lips I now had, something they had painted on them before applying the red gloss had made them tingle and now I could see the results. Plumped up kissing lips.
All happy besides me I was lead of the meet my partner Kim, she was in a smart suit, shirt and tie with a tribly hiding her hair now, the jacket gave her the look of broad shoulders without looking like an american footballer, she looked quite good for a girl. We made our entrance linking arms as if I were the girlfriend, again applause and excellent marks for everyone and great comments. It was now late afternoon and the tutors suggested that rather than waste the effort we have a class night out, all the other girls would go home and change meeting up about seven at a pizza hut. Kim was not keen but her girlfriends persauded her to have some fun and she could go home with one of them if she did not want her family to see her. Which left me dressed up to the nines and only a bus ticket to get home with. Patricia who seemed to have enjoyed the days activities offered me a lift home. I was relucant, but what else would I do for three hours dressed like this.
Mum was home when I walked through the door, 'oh my look at you' she squealed, she had known about the project but was not ready for the results, 'those girls have done wonders with you, they are so talented............. And you are going out tonight as well....... brilliant' She stopped making tea and called Mark's mum who was round like shot, took pictures on her phone and sent them to Mark, which resulted in me getting a text 'Gorgeous, wish I was there, remember you are my girl' I sent back 'always,love you'
The evening was good fun, some girls were not eighteen so could not drink, but still came to the bars with us, all dressed up and with no boyfriends except Kim we were like honey to any man who fancied his chances, some got a terrible time as over twenty excited girls would tease them or try and pair them off with me, I obligingly played along and Kissed a few before telling them I was really a boy, which got varied responses from 'I don't believe you' to angry homophobes calling me a pervert and the girls unladylike names.
It was back to earth with a bump when I got home, it was not late and mum was still up and clearly wanted to have a chat. She was pleased to see me looking so good but wanted to give me support as I worked through what I was going to do in the morning. I would have to go to the salon and we did not have the time or equipment to do anything then that might alter my appearance. I felt that wearing my jeans or white trousers and a t shirt, like I normally wore would be fine, mum was keen to point out everything about me looked female so why not embrace it, be brave and go to work as a girl. I still felt it was too much for me and the salon to handle in one hit, I would wear trousers and a top. In the morning mum got up to check me out before I left, she was clearly dissappionted I was not taking this oppurtunity to be Jenny, but I was not prepared to be so reckless.
In my white trousers, flat shoes, purple slash neck top a base ball cap and no make up besides the coloured nails and waterproof mascara that I did not work to hard at removing that was about me, oh and the darker lips that was a reminder not to use staining lipsticks in future. Other things like neat eye brows and still swollen lips I could do nothing about either, but I felt as though I was not to different to the Jens they saw a week ago. I arrived on time as always and started with my duties. Before all three staff had turned up, but before any customers, I had been hugged and congratulated on my look, mum had sent them pictures of me from the night before and now they wanted to know why I had come to work looking like I did. Being professionals it took no time at all once they had got me in a chair to give my hair a quick blow dry, and to whizz some light make up over my face, mum turned up with a bra and fillers, as well as some jewelry. They now were calling me Jenny and I had no excuse to stop them, besides they seemd to be enjoying the fun of transforming me. Work turned out to be fun as well, I tried very hard to be girlie with most customers not realising the change, some regulars twigged that Jenny was Jens but whoever was serving them at the time would explain how I was on a course and having to look like a woman as part of that course, which made them ask more detailed questions, which made any time I spent with them interesting to say the least.
Towards the end of the day Ray invited me to join him that evening, he was going into town after work for a 'nothing planned just see who I bump into night' I asked if I could go home and change, he said only if it was to put on my dress, I blushed and said I would think about it, the women then told me they fancied coming as well so I was steamrollered into going. As the last customer left at gone six we had some cleaning still to do, but Sara pulled me to one side and told me to use her make up bag and brighten my colours, what could I do but play along and do my face for night time, then finding her scent, tested it, like it, and used it. Going back to help with the final chores. I told mum what I was doing and when I was overheard on the phone Kate told me to invite her along, which she heard and said she should come along later, and did I want her to fetch me anything to change into, I said no but just knew she would bring me some extra female items of attire.
By seven thirty we were all in a bar eating salads and drinking wine. Mum had brought along some heels and a dress if I wanted to get changed I was persuaded into the shoes, but the dress would be too much hassle to change into given the state of many toilets in the bars. The first thing they all said was how well I walked in the heels, then over the evening I could not stop mum telling them about the parties I had been to with Mark as his female partner, they all thought it sounded a hoot and loved the idea of me in a wedding dress. They had also worked out that I was possibly getting more feminine in behavior and looks, and that it would be quite possible for me to go full time if the situation arose. They already knew I had a boyfriend, now they knew who it actually was. Ray now loved the idea of taking us to gay bars where I would easily be accepted without question. I was with my mother and not completely sure how she would take this development, nor how Mark might feel about being in a gay bar. We parted later on with everyone, but not me, being keen on me turning up to work in a weeks time wearing a skirt, I could only say maybe but knew the pressure mum would put on me would be constant.
My next problem was how should I turn up to college on the Monday, we only had two weeks left but I felt I should maintain my place as Jens, I rang Kim and asked for help on the Sunday, she told me to play along with the tutors and turn up in my college girl outfit, I pleaded with her to at least trim my hair and remove the nails, but she was busy with her boyfriend and told me to be the person the whole group knew I really wanted to be, I asked what she meant, she bluntly told me everyone in the class had expected me to come out ever since I first walked into the introduction classes, now I was speechless but struggled out a 'you are joking' she told me she was not and she had to go.
Monday I dressed in the pinafore and leggings, I did a muted face, filled my wrists with bangles, gelled my hair to give it volume, then slid my feet into the wedges. Getting to college was not too hard besides the nerves that were playing in my stomach. For the first time in ages I felt very self conscious thinking everyone was staring at me, but I had my worst moment as I went into the study room and faced my class, there was a squeal and several jumped up to greet me, Kim turned to a couple sat by her 'Told you Jens is one of us really'. No one called me wierd, maybe they had got used to me over the year, maybe they did not care, whatever it only took minutes for the novelty to wear off and our usual conversations to return. When Patricia entered the room she scanned us to see who was there, she then came over and quietly said 'Glad the true you has come to class at last' then to everyone 'Right girls revision ahead of exams at the end of the week, any one want to suggest a topic?' And that was it I was one of the girls and it was not a problem.
I had gone a year not being that open about being a cross dresser and then everything happens at once. I had had a week of going to college as Jenny. Mark had come back mid week as he finished for the summer, and loved the fact that I was a girl fulltime, taking me out every evening that week, we even had a night when we decided we should stop hiding from our old friends and went to our local pub to see who was about, Mark got a warm welcome from one of the guys there who he had been a good friend through school, I did not fare so well, no one at first recognised me, then when they did I got a hostile reaction from one who I did not really know, and I was ignored by most of them which made me think they were talking about me. A couple did chat and ask how I was and what I was doing. Cherri who had been at the parties and was not phased by meeting Jenny again, reflecting what others had said then it seemed ineveitable that I would do this after seeing me at the haloween dance especially where I allowed myself to be less restrianed. I left the pub not keen on repeating the experience but Cherri did exchange numbers and told me we should meet up some time and maybe include some of the other girls like Samantha, I said that would be nice.
The weekend was a big turning point though, mum and Emma decided that it would be nice to have a meal with Jack and Sean, they had been around all year, I had not gone out of my way to dress for them and would hide in my room if I was not Jenny, to keep the peace with mum more than anything else. Jack had stopped overnight on occasions I was away with Mark and sometimes when I got home from work mum would look less than smart, more just a got up look, so I guessed something other than chatting was going on, if you know what I mean. Well that Saturday we all ate together, Emma cooked the main course, mum and I cooked the pudding and provided the wine. It was going very well, I was wearing the red dress I had now been given to keep and had enjoyed more compliments on my new look. As we finished our puddings and I served coffee mum tensed up and went quiet, I think only I noticed at first but Emma looked at her as well. I have something to tell you, she finally said, everyone looked at her, I have been lying to you, she looked at Sean and Jack, I think I have to tell you the truth now, I should have done this ages ago but did not want to change things, she had everyones attention wondering what announcement she was about to make, 'Jack, Sean, this is going to be hard to understand but Jenny is my son.' There was a silence, Jack started laughing, I started blushing bright red, Emma was doing a good shocked look, she clearly knew this truth but the situation was a surprise. Sean was looking around, 'you aren't joking are you' he said calmly, 'I never guessed you, are a great trannie Jenny.' I could stand it no longer and ran to my bedroom, I heard Emma tell Mark to go after me. As he hugged me in my bedroom we could hear the mothers talking to their boyfriends, Jack was clearly not happy with the truth and could be heard raising his vioce, then shortly after the front was closed and Mark went to see if the coast was clear. Mum was crying in a chair, as Emma and me tried to comfort her Mark made another coffee and tidied up the table. Jack had said some cruel comments, Sean to be fair had tried to calm things down but Jack was not happy with the fact that he was going out with a liar, a woman who encourages her boy to be a girl, a boy who had managed to fool him for a year into thinking he was girl or that Mark was somehow gay. Whatever mum was hurt, she said she had to do it sometime and had run it through her mind and after my good outcomes at college and work somehow expected everyone to be OK with the idea of me being a girl, clearly she got that wrong. Emma tried to say he will call her when he cools down but she did not convince anyone.
The positive outcome from this busy two weeks of revelations was that I had nowhere to go that I needed to be Jens, if I choose my friends carefully I could be Jenny fulltime, not just at college and at work. Then as if to seal my fate the following week Ray called me to ask if I would work full time at the salon as an apprentice, he then put on a condition, that I present as Jenny while at work, my fate was sealed when I said yes and turned up to sign the forms wearing a skirt and heels, at least with these three there was no chance of a negative reaction, it was a good place to start my career from for sure.
The end
Paul could not believe what he had done, he had made a booking before and bottled out before opening the door, this time he had managed to go through the door of the nail bar. Once inside the petite woman smiled and spoke so nicely to him he melted ‘this will be ok’ he reassured himself’. 'Going somewhere nice tonight?’ she asked. He hadn’t thought of a back story, he just wanted his nails done, a real manicure.
'Oh just out with a friend.’
The woman considered him carefully, noting his pierced ears, hairless arms, neat eye brows, before showing him to her desk and placing a display of coloured nails in front of him 'If you are going somewhere special having your nails looking brilliant is the best finishing touch, now what are you wearing, but I think this pink will suit your skin and hair colouring if you have not decided.’
Flustered Paul looked down, pink! he would love pink 'I er no I am not sure what I was going to wear’ which was true, he had a few outfits at home but had not planned the day beyond the manicure. 'I was only wanting a simple manicure.’ He eventually said, but it was too late he must have been daydreaming for a moment, his right hand was in her left and the first of ten nails was secured to his finger. 'Oh I’ he stumbled over his words 'that is long.’
'That is what everyone says the first time, but you soon get used to them and they are so strong they will not break off or split’ Paul’s mind was spinning, he stopped looking at the woman and back to his hand, three nails done. His heart was racing, this was truly exciting, a fantasy come true, getting his nails done properly. He knew he should say stop but was transfixed by his hand with now five long nails on it, his mouth was not working though as she took his other hand. He sat mute unable to move as one by one she trimmed each long nail neat, then painted each tip with glossy pink polish. he had painted them at home and the smell was intoxicating, this was overload, he just sat loving the moment watching his hands transform.
Sadly the bubble burst as she polished the last coat onto the last nail. 'That will be £25 please.’ Paul struggled with the pin number machine and found tapping with the tip best. 'Have a good evening with your boyfriend, sorry I should not be assuming it is a boyfriend. Whoever it is I hope they like them as much as you.’ Paul was still in shock as he walked out, nails carefully curled into his palms, was he so transparent ?
Once in his car he unfurled his hands, they looked great even against his white jeans and lemon t shirt, god knows how he would cope with work on Monday as he tapped the number of his boyfriend into his mobile with his long pink nails to find out where they were going that night.
New Challenges
by Lauran
We were going to do it, we had discussed what was needed, and how we were going to do it, all we needed to do, was to actually do it.
Running marathons like a lot of things needs planning and preparation.
It started off with one of those idle chats about what if we could do anything, and he suggested that as a serious shopper and general couch potato I would never consider doing a marathon, I liked my heels too much he told me.
Then it was my turn, and his comment about heels made me think down a rather perverse route, he liked put across this manly image he would never go out as a woman, in heels, the full works in fact.
We both laughed and took another drink of our wine. But then as we were getting ready for bed I glanced at myself in the mirror, I was getting a little out of condition and maybe some exercise would be good for me, and told him that maybe I should do a marathon as I pulled my tummy in. the look in his face was priceless, he went pale, started telling me how hard it would be, how people die doing it, how I had no kit, but what I think was at the back of this was that if I did this then maybe I would want him to do the challenge I set him. And that seemed like fun.
The next day I had done my research, a marathon was do-able, six months proper training and the right shoes should see me get to the finish line. I choose a big city race with lots of fun runners so I could go slowly and not stand out, then ordered my shoes and some kit, then waited for the look on his face.
Three days later the packages arrived, I left them out deliberately so he would ask about them, which he did, and as I opened them he wilted a little, asking if I was teasing him, or was I serious, so I showed him my receipt for the entry to the race and he laughed but only weakly, he knew if I got an idea I would see it through.
I had my training schedule written up with how far I should run each day, or do some cross training, everything just getting gradually longer or harder each week over the next six months, alongside it I made out a schedule for Mike so he could train for his challenge, which would take him from a man to being a woman. While I would go from couch potato to athlete.
My first run was to make sure everything fitted and was comfortable, while doing a couple of miles running and walking. Mike was to look through magazines and a few stylebooks I had so he could get an idea of what lay ahead and as I put it to visualise how he will look in six months, rather like me visualising the finish line. My run I think was easier than his experience, he looked worried and confused when I got back. He had convinced himself he would never look like a woman, and it was ridiculous to try. Maybe I had given him the wrong information first, those models do look great, and Mike would never be a model, so I showed him some cross dressing websites to show him how a man can be transformed into a reasonable looking woman. When he had been reading for a couple of hours I asked him what he thought, he was a little more positive but still doubted he could do it. I used the running metaphor, I did not know if I could do the marathon, but I have to start with trying out easy stuff until I get better, maybe I would fail, and suggested he take the same attitude, small easy steps first and see how they go. This went down better as there was the option of failure, though I don’t like it, I will accept certain things just cant be done, but I knew both our challenges were possible even if Mike did not.
One thing I was going to be insisting on with Mike’s challenge was that he was going to be a feminine woman, not a butch half way woman. His training plan got more detail, but whereas mine was a daily schedule, his was more of a weekly plan
Week 1. Buy knickers, camisole, pop socks and low heeled shoes.
Week 2. Wear the socks and shoes around the house, underwear when ever possible.
And so on until
Week 29. Go out fully dressed, be a woman and do something Michelle has never done before.
The highlights were for Mike and possibly me.
Week 3.
Running for 30 minutes without stopping.
For Mike wearing knickers to work, he described it as slightly wrong, stimulating thinking it was wrong, and stimulating as the satin caressed his man tackle.
Week 4. Proper noticeable heel
We went out and bought higher heels, 40cm block but it was getting there.
Week 5. Wig
This week I ran my first 6 miler.
Mike now has a long brunette wig that flips out around the bottom and brushes across his eyes. He looks very cute.
I tried and succeeded to get an extra experience into the schedule, when I am on I persuaded him to also wear a tampon, so he can empathise with my monthly routine. On the Wednesday we were having sex and I found the cotton thread there, so nice to know he is taking this so well. He is only using light, but I think by the end I shall be giving him extra heavy.
Week 7. Wear a bra with filling
I went online and found a runners website called fetch, lots of people on there doing the same race, lots of support. Also joined a running group that makes the longer runs easier with the company.
We ordered false tits for him, and two 34C bras, without any comment from me he has included them into his evening dress change programme.
Week 9. Tampon.
I managed 10 miles, without stopping.
Week 10. Blouse or female top
His first blouse, a soft white cotton, very nice. The bra was pulling his shirts and he admitted they were uncomfortable with his shirts. It looks a little incongruous but with time he will get there
Week 11. Female cut trousers
This I thought might have been harder, but we bought black cords, the flat front, side zip fastening did raise a few murmurs of why a side zip, but it is small steps leading towards the goal. They are nice and long as well to go with heels.
Week 12. Wear trousers all weekend, and bra when at home evenings.
I did buy him a short leg pair of trousers, so he could wear them with his male flat shoes, made sure there was a side zip though, which was hard. Now he can go out at the weekend without changing.
Week 13, Tampon, (large)
I read an article about how running increases libido, I realise we are doing it more, but I had put it down to Mike turning me on with his dressing.
Week 14. Skirt and tights
His first skirt, flared calf length denim. He is wearing it around the house with dark opaque tights. I don’t know if he is just copying me, but he quite naturally wears a skirt, tucking it under as he sits, being careful when crouching so as not to stand on the hem, little things like that. Also bought more tops for variety, a vest, a pink T and thin cardigan set, and a thicker knitted cardigan.
Week 15. Full shave
This one he did not like, it is a more permanent change, and he could foresee problems if anyone saw him in shorts. But when does he wear shorts? Only on a holiday. He gave in and I showed him how to use imaac and a lady shave. Rubbing in the moisturiser got him in the mood for an early night. When he wore his tights the next time he told me how nice they were on hairless skin. I took that as a yes to there being no more trouble keeping him hair free.
Week 16. Make up. First try.
I did this on the Sunday, and I knew it would be good, his features are not heavy set so when I had given him the works he looked really good. With his wig on even he accepted I was right and he looks good and would pass as a woman, visually anyway. During the week he practised with the make up, coming for tips when he got stuck.
Week 17. Full make over. Tampon
I have done the first of my 20 mile ‘long’ runs, this is really tough.
Make over done at the weekend, by himself while I was on my run, make up, wig, full underwear, skirt, blouse and heels. He did not go out, just pottered about the house. I did though and bought him some satin pyjamas, a treat for getting this far. I am not sure who enjoyed them the most, but the satin and smooth skin turned us both on.
Week 18. Go out in trousers wig, and make up.
A week after his first complete cross dressing we toned down the make up to mascara, lip gloss and light blusher, and chose clothes so he could go out totally in female attire. At a glance you would not notice anything. We did feel the bulge at the front of the trousers needed some attention, Mike has been told to experiment on hiding his man bits for a flat front.
Week 19. As above, but with breasts.
My second 20 mile run.
He has now gone out as a woman, the full works, bra, wig, full make up and heels. We added a pale pink nail polish this time, will use more obvious colours in coming weeks. It was only a walk down a road at night, but it has been done.
Flat front sorted, he has bought a gaff, does not look to appealing when in panties, but does the job, and he will try to think of something better.
Week 20. Deportment lessons.
He is quite good already but it is on the schedule, so I had him walking with a book on his head, and telling him off if he clenched his hands or did not sway his hips.
His toenails are painted fulltime now, and today they are baby pink.
Week 21. Evening’s, full change. Piercings? Tampon
The full change he just did without prompting, I came home Monday to find him as Michelle and cooking the meal. After much deliberation he agreed to have studs in his ears, I explained how they needed time to heel, and it needed to be done now. Good job his work does not have a smart dress code.
Week 22. Go out in a skirt.
For him to go out after dark for a walk with me was easier than either of us expected, he was nervous as he always is when he worries who might see him, but he has been out a few times in trousers so to add the skirt was not as big an issue as it might have been. His female routine is getting more involved, with changing when he gets home, shaving, and now cleaning his piercings he is realising how much goes into being a good looking woman.
Week 23. Last long run.
Evening out with me as Michelle.
With a few evening walks under his belt as it were, we went out to a more public place. There is a gay area in the city that we knew would be safe, so after a Saturday spent going over all his preparations we went out for a drink and a meal on Canal St. He looked so cute and I could tell he was getting a buzz from it, as for me walking down a street holding a females hand was an unexpected delight.
I found out when he undressed that he was not using the gaff, looked great undressed, but sex was hard, as he had taped his bits between his legs.
Week 24. Start tapering.
Go out solo. Tampon (super)
Entered a half marathon, felt good at the end, pleased with the time.
He had already done a few walks alone, but this had to be more public. First off he did a late night shopping at Trafford centre, just window-shopping, but he came back with a new top and a neat flared mini skirt, said he wanted to know how it felt and if he liked showing so much leg. Next, at the weekend we went to Canal St separately so I could watch from a distance and save him if he got into trouble with men, he did look the part, possibly to well. He glued his breasts on for the first time on Thursday and kept them on until Monday, it is quite odd sleeping with him with his breasts under the nightdress, but odd in a nice sort of way. Another event of note this week was the super heavy tampons I gave him, he never questioned it, just used them.
Week 25. Long nails, and tanning moisturiser.
He was spending all his non-working time as Michelle, even did the weekly shop on Friday in trousers and heels. While out, he picked up the essentials for this weeks session. Saturday saw him with long nails fixed to his fingers, and his pale skin getting a little bit of colour. This would take time but I felt it would be worth it.
Week 26. 75cm narrow heels. Stiletto sandals?
Last long run, I start tapering.
The nails only lasted till Sunday evening, but he kept on with the tanning every evening, by the end of the week his skin was looking quite good. So we went shopping and bought him the stiletto sandals that he could wear without tights, but also bought stockings and suspenders, because we could and so he could enjoy the sensation of wearing sexy underwear. Now I felt he was getting close to the challenges final stages as we went out that evening with him in a skirt and proper high-heeled sandals.
Week 27. Decide on final event
We have two weeks left and over a drink in a bar we decided that he really had to do something totally girlie, something only a woman would experience, as far removed from Mike’s experience as possible. I did not like to say but he had already done lots of girlie things Mike would never have done, but I was looking for an extreme situation now. We considered a salon trip, but what extra would he do that was new? Then I noticed a couple kissing, and remembered the odd occasion when Mike had got chatting with men in bars when he was out on his solo runs. So I suggested that Michelle as a girlie girl should have a boyfriend, Mike paled under his make up, but I told him to hear me out, Mike was not gay, but with me we looked like lesbians, a couple of women being affectionate, to look proper female Michelle needed to partner a man. This raised questions about who and where to find such a man, but I said he should leave it to me I was sure I could find someone nice to partner him as Michelle.
Week 28. En femme as much as poss. Tampon (extra super)
Michelle is around fulltime it seems, the house is very tidy and the washing is always done now. I found a partner by going online in some of the cross dressing sites, explained what I was looking for in the classified ads and was amazed how many replies it got. Most were weird but three I followed up, then I got one to ring Mike and ask for Michelle, who was not in on this at the time. Pete was great, he rang asked for Michelle, Mike stuttered a little, then said yes in his best voice, Pete chatted and explained about how he would like a partner for the weekend as he was going to watch a marathon, but wanted to make the most of the time as he could not run, and spend the weekend with Michelle. Mike knew it was a set up but quickly fell into the charade, and went online to get a look a Pete’s blog. I came in behind him as he read. Pete was a good looking guy who liked his women different, he was a fit and active man who should have done this marathon but was injured so with the travel booked he was going to go anyway. When I said he was a nice bloke, Mike or maybe Michelle replied with a rather unexpected ‘umm, yes he is isn’t he’
This triggered a sequence of events not in the plan. On Wednesday Michelle had been on the phone to Pete again and made firm plans, Michelle would travel with me to the race, but I would go off with new found running friends I had meet on a runners website for a meal, then apart from sleeping we would spend the weekend with our new friends. This meant Michelle had to get ready and had soon found a salon that would accept a man called Mike for an appointment later that day for several treatments.
His hair was not long enough, but they weaved his wig into his own hair, he had proper false nails fixed and painted on his fingers and quite to my surprise had let them thin his eyebrows far more than I had ever dared.
Thursday he declared that he would need a new outfit, and went shopping alone, coming back with a gossamer thin red dress that lay over a red satin slip, a pair of strappy spike heels and a neat red clutch bag. His only defence was if it is worth doing, it is worth doing well.
Friday he spent primping and preening himself in the morning, and then about midday we loaded the car and set off. If he had not been driving I am sure he would have been texting Pete all afternoon, I was beginning to think I had maybe been too persuasive. We were only spending two nights away but he was acting like a woman, he had enough stuff for a week, as Mike he took a hold all, now a suitcase was bulging, as well as some clothes on hangers in the back.
He had travelled in his low heels to drive and some tight trousers, but once unpacked he went and showered then went through his make up routine finally dressing in his satin cream blouse and brown disc skirt, tan stockings and the stilettos. He was certainly doing his challenge to the full.
I had dressed in a nice comfortable running top and jeans and was ready to meet my new friends for a pasta meal, but before we parted we had a little chat about how well he had done, he knew everything he needed to know, and he could go through with it, he would be Pete’s woman, Michelle, and he was to enjoy it now all the hard work was over. Funnily enough he almost gave the same speech back about my marathon the day after. We parted at the hotel door, and I watched a very sure woman stride away from me making the skirt swish and the heels click. What a transformation, he had certainly achieved the goal, now could I?
Week 29. The race. Success is assured if the training has been done well.
We both claimed success.
Jenny asked me to write down my experience, so here it is.
She has covered much of the ‘training’, I was not keen at the beginning but there were three events that kept me going.
First was the sensation of female knickers, we had bought the silky ones and they were just fantastic to wear, even the camisoles which I felt a little more conspicuous, were very nice on my skin. When I started wearing them fulltime it gave me a sense of doing something I shouldn’t be doing, not quite wrong, just not quite right a bit like a naughty secret that harms no one.
Second was the body hair, again I was resistant, but once I did it my skin felt so different, especially when I wore tights or stockings.
Third was the thrill of going out dressed in female clothes, even the starter trousers and a white blouse that looked like a shirt, but that I knew were women’s clothes gave me a buzz, like the knickers but better, I was doing something way out of my normal and I was not caring how people reacted I was enjoying being different. This only got better with the introduction of skirts and heels when going outdoors, that feeling of ‘I should not be doing this’ was just great.
I think what Jenny really wants me to note down is my time with Pete. As I say the skirt wearing was brilliant, I had been out to Canal St and shopping many times in the weeks before, the last few days being fulltime. So I should have been confident of myself but I was going to meet someone I had only spoken to and e-mailed, what would it be like in the flesh, would I be any good at keeping up the pretence of being a woman?
We had arranged to meet at a coffee shop near the hotel, and having exchanged pictures it was easy to recognise each other. He looked every bit as fit and handsome as his pictures, I was even his height when in heels, but then I am on the small side. The coffee went well, we chatted about running and his other interests, then about work. After a while we moved onto the marathon expo, a large show with lots of stalls selling running stuff really, I felt very conspicuous in my heels, as everyone else seemed to be in trainers. Pete meet a few people he knew and promised to give them a cheer in the race, I bumped into Jenny as she moved between the vendors, she had bought another running top and had a smile on her face. She had contacted some of her group, they had a meal booked and she intended on an early night, so told me to come in quietly and make sure I get in the right bed. The hotel only had twin rooms left. With a quick peck on the check she told me Pete looked gorgeous, I smiled back and told her I knew.
Anyway Pete was not running so we could drink and eat whatever we fancied. As the evening moved on we tried a couple of bars, then a pizza restaurant with more wine, we even did the sharing sweet. I was really getting into this girlie thing, so much so that as we ate I would touch his leg with my foot, then when we left I linked his arm. We found ourselves near our hotels in another bar and I was on the gin, I asked about his liking for us special women, and about his exploits, which he was candid about, he was gay but did not like being intimate with a full on man, whereas with someone like me he gets the best of both worlds. Sex he said was better than with a real woman and told me about some of the trannies he had been out with, one he even lived with as a couple for two years until she decided she no longer wanted any male bits, and had SRS which Pete was not happy with. By this time we are well cuddled up together and I am thinking if he invites me to have some sort of sex what would I do, it sounded quite exciting to my female immersed body and alcohol dulled mind.
It was getting late when we decided we should head for our hotels. He offered to see me to the door, I pointed out it was only across the road and as we turned for a good night kiss I opened my mouth a little wider than I intended and within seconds our tongues were meeting for the first time. When suggested he show me his room I just threaded my fingers into his and followed, this was just so much fun pretending to be the girl.
His room was nice; he had got a double room and what I expect is a nice view in the day, much better than ours. He brings out some cups and offers me a coffee while I made myself comfortable on the side of the bed. Before the kettle boiled we were kissing again and getting into it, his hands caressing most of my body, undoing buttons and exploring the tops of my legs, I was not so forward, until he said I could do whatever I wanted, as he took off his jumper, his muscles looked excellent, so toned. I ran my fingers over his chest and for some reason noticed his trousers bulging at the front, I must have stared because he confirmed that I had done that to him, then stroked it through the material, I felt it twitch, wow that was me doing this, he slowly undid the fly zip and I got my first close look at another man’s penis. Completely lost for what to do, I never considered this situation, but I was being girlie and asked him what he would like me to do. Stroke it he suggested, this made his breathing get a little heavier. Then he asked if I would kiss it or stroke it with my tongue. By now I knew he would cum soon, I had been there myself, and I was just taken up with the whole experience, so as he lay back I leaned over and kissed the tip, the licked it, feeling it pulsing, then for no better reason than I always wanted Jenny to do this, I swallowed his dick and started bobbing up and down on it. About four strokes and he came straight into my mouth. He pulled me to him and kissed my still cummy mouth asking if I liked it, I had nothing to compare it too, but honestly said it was not the most revolting thing I had had in my mouth. We lay for a while until the energy returned and told him I should be going, which I did after a quick tidy up of my appearance, and left to spend the rest of the night in my single bed.
Next morning Jenny was up and anxious about how she could complete her challenge. She was dressed and ready early so she could eat early with time for it to go down. I was being girlie so I took my time dressing and doing my face. We then went to the start where I had to leave her and wish her good luck, then for me it was off to find Pete.
I had not mentioned anything of the night before, but seeing Jenny made me feel as though I was cheating on her in some way, but I was not going with another woman as in an affair, I rationalised it as two men mucking about in a role-play situation. So when we meet up a bit later I happily greeted him with a full kiss and took his hand as we walked to the point he said would be a good place to watch from. I had come prepared in my denim skirt and a warm jacket, I was not sure about a full day on my feet in heels but you only get to do some things once. We behaved like teenagers really; he would cuddle me from behind letting me feel his erection in my back. Then we spent ages cheering on people we had never meet just shouting out names we read on their vests. Pete’s friends went past, then a good while later Jenny jogged past I called her and she waved back, then she was gone. A coffee and make our way to the finish Pete suggested. His friends finished two hours before Jenny, so I did a lot of standing around while he went off chatting with mates. I was beginning to think something terrible had happened when at five hours she jogged over the finish looking quite fresh and beaming a fantastic smile. We hugged, she told me it was great, what a brilliant experience, then saw Pete behind me, gave me a kiss and told me that there was man waiting for me to be his woman. She had made lots of friends and they were meeting up for a celebration later and I should do whatever I wanted she would see me in the morning. Had I heard right, she virtually told me to go and let this man make a woman of me, and not to rush back.
We had most of the afternoon to kill, so I suggested a walk around the shops and get a bite to eat, this was done like a young couple, I spent ages looking in dress shops windows asking what he liked, and wondering what I liked. We ended up in the hotel bar, and watching some runners arriving looking worn out but happy. But this was getting boring so I asked if I could use his toilet as a pretence for going to his room. And after I had relieved myself I made it obvious I wanted to repeat the previous evenings action when I undid his pants and knelt before him. It was just so far from my usual Mike behaviour I was able to do anything I thought Michelle would like. So when he had pumped his load into my mouth, and I had given him a cummy kiss. I told him I was going to get changed for the evening and I was not going to accept McDonalds as a restaurant.
I left for my hotel room, and a shower, then a moisturise, next a careful night time make up, then my new outfit, red strapless bra, red thong, bare legs, the red dress, chandelier ear rings, some necklace and bangles I borrowed of Jenny and my spike heels, I checked I had everything in my clutch bag, then waited for his call to tell me he was in the lobby.
After a decent pause, I went down to meet him, I felt almost naked in such a thin dress and skimpy underwear, but his expression as I wafted towards him was best described as open mouthed. So I went up to him kissed it and told him to close it. He did not look too bad either in a smart suit.
We had a lovely meal, I enjoyed the walking around in the dress it was so sensual as it brushed my legs and hands I thought I could easily get used to this. But all nice meals do end, and as we had our brandy to finish with, the conversation turned once again to how good I looked, and how much Pete would like to spend more time with me, I insisted he only had that night, so he insisted we make the most of it. He then told me we were going back to his hotel because one thing he had been asked to do was to make me feel like a woman. I told him he had already done that and I knew I looked like one and was enjoying it. No he insisted in his hotel he could make me feel like a woman.
I took a while to get there because I wanted to walk and enjoy the dress, but once he had the door shut I started to kiss him, then went for his cock, but he pulled me back, undid my dress so it fell to the floor, ‘just as gorgeous without it’ he told me then started kissing me, ‘tonight is about your pleasure’ this would be hard I thought my equipment is securely trapped in between my legs, but he continued to arouse me, then with a move I did not expect slipped a finger into my arse. I tensed but I soon relaxed as I realised what he had in mind, could he make me feel like a woman by inserting his dick in my hole in a similar way that any man might fuck a woman? I relaxed and let him get on with it, trying to respond as best I could. Soon I was on my back, legs in the air with my hole lubricated and his erection finding it’s way inside, I flinched as the muscles stretched but I guess the tampons had been helping me down there, then he explained about a g spot he hoped to find, he was gentle as he slowly pumped into me, then he hit something that sent tingles through me, and a wow out of my mouth, good he asked, all I could say was wow between the ouches, he was getting more vigorous until I was pulling his buttocks into me and telling him to keep going, then I exploded inside, I am sure he came as well, but I did not care as I lay there exhausted my arse full of cum and the muscles feeling shredded. That had been one very different experience that Mike would never have done, and one Michelle had not done before.
Ramifications
For me the result of getting fit and succeeding at the marathon left me wanting to stay fit and continue running, it had been such a fantastic experience, Paula Radcliffe need not fear me but I had achieved my goal and wanted to do another race, but for the first week I was told to rest, and I was knackered so that was easy, then I rejoined my local running group and started training again.
I felt so knackered and so good at first I did not realise that the challenge Mike had done had left a legacy with him as well. First thing I noticed was a week or so later when sorting the washing, there were no boxers in there, when I challenged him over it he just simply told me that he had learnt much from his experience, and the knickers felt much nicer than his regular male pants so why not. I did not disagree; I would not choose boxers either.
About a month later I realised that his skin was still tanned and hairless, I did expect the body hair to be returning but maybe it was slower growing than mine.
Maybe I was going out more and had not been taking particular notice of Mike’s appearance but one weekend we were shopping for our food and I recognised that he was wearing his ladies cords and a top that though much like a T shirt was not a loose man’s style. Rather than come out with it directly I took a detour into the clothes section of the supermarket and picked a few items, then picked up some flat sandals that were Mike’s size, ‘Do you like them?’ he pointed out they were not my size, so I pointed out they were not for me.
‘In that case I prefer these’ and picked up a black flip-flop. I just put them in the trolley and carried on as if it was quite normal for my husband to choose delicate shoes.
But then when we got back to the car he took them out and tried them on, ‘Do you like them?’ he asked
‘Well I am a little surprised, but they do go with your outfit well. I think we need a talk’ there was a pause,
‘About shoes?’ he asked
‘No about you, your clothes in particular’
‘Why do you not like them, they are not my favourite but they are good enough for shopping’
He had never been scruffy, clean and tidy more than smart, but I had sensed he was more aware of his looks since the marathon, I was at a lose as to how I should react, ‘We never talked about how you felt after our challenges’
‘You talked about your running but I was never sure how to explain how it felt, even how I feel now’
‘Do you want to talk, the clothes have stayed with you, and they look good on you’ ‘Thanks I wore them today to see how I would feel being out in women’s clothes, not as a training exercise, just to see how I felt’
‘And?’ I asked
‘I like it, men’s jeans and a T are so predictable, I had to think what to wear, and I feel different, I am not just a bloke in jeans I am me, do you like it?’
‘Why can’t you do this with regular men’s stuff?’
‘Don’t know, I like the fact I am dressing differently I suppose, there is a part of me wanting to express differently, anyway answer me, do you like it?’
‘Yes you look very sweet, but I would like to hear about your challenge’
That was when he wrote out his piece. To say I was shocked would be an understatement, I did not think I had encouraged him to have sex with Pete, but he obviously did, and I had to think what that act meant to our relationship, was it 2 blokes mucking about, did I want him to experience a woman’s position, was he overtaken by the whole being girlie thing and lost it for a while. I was not sure, but once he wrote it, he gave it to me and took a very long walk leaving me plenty of time to mull things over, he knew what he had written could have deep implications, but honesty is one of things I love about him. For me I did not know how to take the news and when he returned just acted as though nothing had happened, made our evening meal, watched TV, went to bed, made love. Well it was Saturday.
When a week later I asked why he had not worn his new sandals, he said he was unsure how I know felt about such things, I asked if he liked them, he said yes, I said well why not wear them. This relaxed him and over the following weeks wore his less manly but not overtly womanly clothes, that is until the weekend when he wore a lemon blouse, at first glance it was just a soft yellow, but if you cared to look it had small buttons and was to short, that plus the sandals made him look quite camp, and I told him so, ‘Do you mind’ he asked.
‘Or would you rather I went for a more extreme look?’ I was on the spot, I had opened up this Pandora’s box, he had never been uber male but he was not looking particularly male as I looked at him.
‘Are you wanting to wear a skirt do you think?’
‘Not at the moment, I am happy just wearing nice fabrics and these clothes fit the style I want’ I conceded I did not mind and we went out for our shopping.
I suspect it was that moment that lead to his more flamboyant style developing, he bought tops with no cuffs so the sleeves opened out to a bell shape, linen trousers that looked so cool in the summer and more flimsy sandals that he said were so comfortable.
It must have been months since he had had his hair cut and while watching a TV programme asked if he would suit a style like a certain presenter who had his hair gelled so it swept forward and across his eyes the neck falling comfortably past his collar. ‘Why don’t you go to my hair dresser and ask to look through his magazines, you might see something else you like better’ next evening I find out he had an appointment and wants me to go along to make sure he does nothing daft. I was uncertain as to how to react but agreed to accompany him.
John spent a while chatting trying to understand what Mike wanted to do and how much trouble he was prepared for, both in care and looks. Mike said he was not bothered if the style was a bit unusual, and he was happy to maintain a style if it needed it. John was persuasive and both of us accepted he could do whatever he wanted. I had other things to do and left Mike in John’s hands. Three hours later I went to pick up my restyled man, who was a bit poorer in the pocket but definitely richer in style. His hair was now lighter with highlights around the edges, his longish hair had not lost much length but seemed to have more volume, it was standing up and pushing forward, imagine the wind blowing from behind, with a feathered edge. I was not sure if it was the colour or the shape that struck me most, but together it was striking when compared to his previous boy style.
He had gone dressed quite conservatively for Mike now, but once home changed into his cream mohair jumper, brown linen trousers and sandals. Coming out of the bedroom to ask what I thought. ‘Very nice, you are unmistakably camp you know’ ‘That’s fine with me, is it with you?’
‘Of course, should we go out tonight, no point wasting the hair style on the TV’?
He changed again before we went out, choosing a loose lime green blouse with a wide satin ribbon around the waist tied in a bow to create a belt, tight black trousers and of course sandals, he even had jewellery on if you class a short bead band round his neck and wrist as such. What was most interesting was his keenness to get out and see how he looked to others, we did a few bars and people did notice, a couple of strangers even said hello in a friendly way, and when one couple started chatting we found ourselves invited to another bar we knew nothing about, but soon realised it was for the more interestingly dressed folk. Mike even looked normal compared to some in their fetish gear.
All the while my running is continuing, and I came to realise that while I was out Mike was experimenting with his look, always careful to tidy up before I got back but things did get missed.
He was good at looking after his new hair style, washing and gelling it to keep it looking good, at times gelling it into a different style, the side parting and across his eyes being the most common.
Changes started to become common place, one time he came to bed in a new set of nightwear, he had stayed with the satin pyjamas mostly, but these were not the usual button up blouse type, they had an over the head camisole top with trouser bottoms, all in cerise. It might have been feminine but it did not stop his manhood working, if anything it improved with my being able to caress his smooth skin under the satin fabric.
Another hint as to my changing man was that I was getting through tampons far quicker than I used too, especially the larger sizes that I rarely had a need for, but he was always discreet and never let me find a cotton string hanging between his legs.
Then one day I could not find my tweezers, turned out he had been using them, and when I took a looked at his eyes I knew exactly where they had been used.
Another time he had a sore face, and admitted he was having his beard removed, bit drastic I said, he just pointed out how I never liked a man with a beard, and he would soon be able to stop shaving.
His work has always meant that every now and then he was away for a few days, but when I found out his red dress was missing on one of these trips, I suspected his dressing was going beyond camp.
On his return I offered to help him unpack, which lead us into why he did not want any help and then into why had he taken the dress, which lead to, do you want to wear skirts again, which lead to would you like to be Michelle more often, which lead to do you fancy a night out this weekend, which became not just a night, but a whole weekend of Michelle.
To be fair he did not wear anything he had not worn before through the day, trousers were still most practical for shopping and housework, but it was the make up and nail polish which defined him as beyond camp and into feminine looks, then in the evening we both dressed up, heels, skirts and full make up and for Mike some new pendant ear rings. Then it was off to visit some bars we had been introduced to before to see if our new image would fit in. At first we were taken for lesbians, but then we meet up with the couple who had first invited us and were full of praise for Mike’s transformation. We had a great night pretending to be a gay couple before going home and proving to ourselves that we were not.
That evening opened us up to a whole new life. Mike became more relaxed about being Michelle and if he was working from home would often do it in a skirt, but doing the whole thing so if anyone came to the door they meet a woman, not a man in a skirt. He was getting back to the stage before his big girlie weekend where he would quite happily go out dressed in a dress and heels without really thinking he should look like the man his body was telling him he was.
Then we meet an interesting couple; he was a very dominant man while his partner was a sexy woman who seemed to like our company. We chatted about lots of things but she kept coming back to Michelle’s great looks, and how fantastic we both looked. Later on we ate in a curry house where I sat next to Suzie and Mike next to Paul, I nearly choked on my wine when I felt Suzie’s hand brush my leg, I apologised and said there was nothing wrong as I regained my composure. Suzie then invited me to go with her to the ladies, where she apologised for being so insensitive but told me I was gorgeous and she fancied me, I asked about Paul the big man, but was told not to worry about him he was not so good when it came to pleasing women, but as for her she was quite good at pleasing women, then stroked my arse as I made my way back to our table. Mike and Paul were quite happily chatting away when we returned, when asked why we had been so long, we just told them we had been getting to know each other a little better, which got a very sly smile of Paul and a confused look on Mike’s face. I did not flinch the next time she let her fingers touch my leg, which progressed as the meal passed to a hand remaining on my thigh. Paul was being equally attentive to Mike, I could not tell what was happening under the table, but he was always offering too do things for him, I remembered what Mike had written about his weekend with Pete and wondered how much he wanted to have that experience again. It was getting late when we paid the bill and we promised to keep in touch, exchanging mobile numbers, then it was home to let Mike finish off my already wet pussy.
We did keep in touch, and next Friday Mike was getting into full Michelle style because Paul had told him he should, while I knew Suzie would be flirting with me again. I had discussed what Suzie had said about Paul not being interested in women and Mike seemed to think she was right, but would not explain how he had come to that conclusion. Mike was in his highest heels, the red dress and looking great, I did my best but went for trousers in an attempt at modesty in the face of Suzie’s flirty texts. I was confused by being chased by a woman and completely lost as to how I should handle the situation, but oddly one thing I did not want to do was cry off even though Mike as well as myself were entering a totally new experience.
We meet at a plush bar, Suzie gave us both a greeting kiss, mine on the lips, Mike’s on the cheek, Paul only gave Mike a kiss, I got a hello, the evening went well and pretty much as expected, they successfully paired us off between themselves, Suzie letting her hands touch me as often as possible, while Paul was giving Mike equal attention and making it appear they were a straight couple. The whole evening was completely strange to me, I was used to playing a lesbian with Michelle, but with Suzie it was for real and exciting, no woman had been so sexually attracted to me and she was very sensual and I was aroused by the situation. I was unsure how Mike was taking the experience, but later when we parted promising to do it again I found Mike was just as aroused only he could do nothing about it, in preparation for the evening he had taped his bits up between his legs, but after my initial disappointment he brought out a vibrator that he used to satisfy my urges, it was while he was pleasuring me it struck me why he should have such a thing, then thought that he may have been using it himself, which made sense if he was using my tampons. So when I had recovered I offered to return the favour, and was surprised how much he enjoyed being fucked. It was then I realised how much the challenge had affected Mike, I knew we could have great sex, but to find out he enjoyed it both ways was a revelation.
As we lay in the afterglow I asked if he was bi sexual, he might be he replied, but then went on to ask if I would give in to Suzie, I said I doubted it, he said I should try it, it is only sex and it will not be like ours. So I came back by asking if he would consider sex with Paul, he admitted to being asked already, well not quite asked, Paul had told Mike that he was going to have him next time if he gets half a chance. Both of us fell asleep not sure what we wanted or what the other wanted either. I knew though when I was given breakfast by a particularly sexy Michelle in the morning that somehow we would find out which way we would go pretty soon.
We ended up chatting about what we thought was being proposed by our new friends, Mike had admitted to sex with Pete and we knew he had enjoyed it the night before, but now he was wanting to know if I minded, I knew that if I said yes he would give in to Paul, I also wanted Mike’s approval for anything I did with Suzie, I knew her attentions had excited me, and I was sure Mike realised this. Our uncertain positions were pushed further when our mobiles sounded to let us know we had texts.
Of Suzie ‘we are having a BBQ, forecast is good, fetch a bottle and sun cream’
Before I could really tell Mike of the invite his went off.
‘Paul here, you will come, you are so hot I cant wait to see your sexy body’
Then Suzie sent another ‘please come and be sure Michelle is with you; Paul is on heat here for her. I wouldn’t mind seeing you either, xxx’
We were sat together and as we read the messages Mike’s first comment was ‘I haven’t got a sun dress or shorts’
‘I don’t think either will be that worried what we are wearing to be honest’ I replied ‘Suppose not really, should we say yes, or do you not fancy it?’ from that I guessed Mike fancied going,
‘You just want an excuse to shop before we go’ he then told me of these denim shorts and a black and white dress cut top he had seen that he fancied.
Then suggested ‘try it once, or even just see how you feel, we can always leave’
Our day was planned, dress, shop, get ready after lunch, go over to Paul’s, and see what happens.
Mike was all taped and glued for a woman’s weekend from the night before, so was ready about as quickly as myself. First we shopped for clothes, I got a nice long floaty summer dress, spaghetti straps and sheer. Michelle found some tight shorts and a top that nearly covered the shorts and was cut so it supported his bust meaning he could go braless. He also bought white spike heel mules; 2” drop earrings with a matching necklace.
We arrived about four, it was still hot and we sat outside and drank the wine we had brought, Paul after a while began to get the coals hot and start cooking, BBQ is such a male thing Suzie just sat and offered advise, I sat watching as Paul had Michelle running around doing his errands. I know it was while they were cooking that Suzie got me alone and told me how Paul had plans on getting into Michelle’s knickers, I said I thought as much, but then added that I thought she had plans for my pants as well, to which she blushed and laughed, ‘off course, you are so sexy, every time we have meet I have been so wet I have had to force Paul to satisfy me’ I felt myself stimulated and knew this would be a day a learnt if lesbian sex was for me.
While I was being flirted with, Mike was not going short. Paul often touching him in normally out of bounds areas between men, and when I went to the toilet I caught them being more intimate than needs be when getting a bottle of wine from a fridge.
We ate chatted and drank, then as the evening cooled we moved indoors. I sat on a sofa and not unexpectedly Suzie came and sat beside me, Paul and Mike followed a few minutes later hand in hand, and when Paul sat in a chair pulled Mike onto his knee deliberately placing a hand on Mike’s thigh. I know it was not our house but Mike was the one who made sure our wine was topped up and going to the kitchen if any of us wanted anything. It was while Mike was out that Paul came out with a shock statement ‘Jenny, I don’t know if Suzie has told you but I have been forced to have sex with her because of you, I have done it twice, I will not do it a third time, you have enjoyed our hospitality now it is your turn to finish what you start’ I was a little stunned.
‘Ignore him, he likes to bully people’ Suzie said, but followed it up with a deep kiss. At this moment Mike walked back in with whatever he had gone out for,
‘And as for you my beautiful young lady, even if they cant get it on, I promise you I intend to have that lovely arse of yours, now get over here I need some attention’ Mike just submitted to this bully and went to sit on his lap then responded to his kisses.
Suzie whispered in my ear ‘our turn now’ and pulled me up of the seat and lead me by the hand to a bedroom. Where I found out it does not always need to be a man filling a wet pussy to get me to enjoy an orgasm. And from the noises coming from the sitting room a man can enjoy being filled also.
Suzie wore me out that evening, it was coming light when I thought I ought to be stopping and making some effort to go home and see how Mike is. I found him in the kitchen in Paul’s enormous dressing gown.
‘You ready to go home?’
‘Let me get my clothes, are you sober enough to drive?’
That Sunday we did not really come round till the afternoon, then it was only to eat, shower and zonk out in front of the TV.
Monday work kicked us back into reality, Mike was a man again, well nearly, we had both had texts asking how we were and thanking us. Over a pizza I asked Mike how he felt, he said sore but wanted to know if I would consider seeing Suzie again. I hesitated and he put in with the observation that I had spent enough time finding out if I liked it, so I agreed it had been a different experience, but was not going to go rushing off as I had Mike already. I got from Mike that he only really thought of men when as Michelle, and though he liked dressing, that somehow being treated as a woman by a man made the cross dressing thing complete.
I am not sure what Paul was saying to Mike, but Suzie was sending me lots of texts suggesting what she would like to do. By Thursday I gave in and told her to meet me after work, Mike was away. Once again she got my juices going and later enjoyed some intimate moments, but I was feeling guilty about Mike.
When he got home on the Friday I suggested he have some Michelle time, he seemed unsure that I should be so encouraging, but told him no taping tonight, he wore a flared skirt and no tape, then when we got home I had full range of his pleasures and rode him before fucking him with the vibrator. He was knackered. And I was torn between Suzie and my unmanly man.
By Saturday afternoon he was looking ultra feminine in a tight skirt and I knew his dick was lost for the day, when I asked what he had in mind, he replied that he thought I would be out with Suzie so he would not be needing it. Then it came out Paul knew about Thursday and the information had got to Mike, how naive to think they did not talk. And Suzie had asked me out to a lesbian bar, so without the men, who she assured me had plans of their own.
I was later to see Michelle teetering along on her spike heels and showing a lot of leg while hanging onto Paul’s arm, but I was no better having my arm around Suzie’s back.
Over the following months I really got to liking Suzie and wanting to be in her company, Mike was also spending a lot of time with Paul who had got him wearing corsets, size D bras and padded pants, so he had a great figure, if not entirely his own. We did go out as a foursome at times, it was at these moments I saw how Mike allowed himself to be dominated, he would do anything Paul told him to do, from what to wear, to where to sit, to when to talk, we had always been equals, now he was submissive beyond belief.
A big surprise was being invited for a meal at Paul and Suzie’s, but they were not the host it was Michelle who cooked and served, sorted out drinks and made sure everyone was happy, I even suggested he should get a maids outfit, to which Paul said it had been discussed, but Michelle had wanted to eat with us and a maid would not be allowed to do that.
Gradually our relationship changed, our sex diminished while our new partners became more important, I could end up at Suzie’s three nights a week especially when Mike worked away, but none of us were very good at the housework so increasingly Michelle would spend her weekend with Paul and clean their house. Then when he spent several weeks working away only coming home at weekends he changed at ours, then went out with Paul, stopped over and ended up staying till Sunday when had had to revert to Mike for work.
I am sure our lives would have turned out differently if I had not decided to run that marathon, but I was still fit and in better shape than at any time in my life, Mike had found something in himself that surprised us both, but disappointingly we were drifting apart, we had become good friends, enjoying each others company and sharing a house. It should not have surprised when Suzie made her suggestion.
Mike was away and recently when that happened Suzie would stop over some nights. We were relaxing after a nice meal, cuddling up watching a soap.
‘We could do this all the time you know’ Suzie said softly
‘That would be nice, but I have think of Mike, he still lives here, well sometimes’
‘Have you seen some of the gifts Paul has got him recently?’
‘You mean the corsets, stilettos and revealing outfits?’ I suggested
‘Obviously not’
I asked her what she meant and she told me about a side of Mike/Michelle I was largely unaware of. He had some thongs with ‘Paul’s’ written on them, he has a classic maids outfit which Paul likes him to wear on a Saturday when he is cleaning the house, and she had turned up unexpected one evening to find Michelle in some of the sexiest underwear she had ever seen, tied to the kitchen table with a vibrator running inside her arse, and Paul nowhere to be seen. Apparently Michelle had made it obvious from the way she was dressed she wanted sex, Paul needed to go out, so just tied Michelle to the table who did not resist, then left her to get on with it by herself.
I felt a bit more distant from Mike after that, I did not really want to ask about his sex life, but did ask how things were, ok he said, and sex, that’s good as well he confirmed, and the maid’s outfit, a bit of fun he said, who for I asked, Paul likes it, I was told. Then I noticed his navel had been pierced, well his blouse was only buttoned around his breasts, I said how nice it looked and took a closer look, from the stud hung a tiny disc which read ‘mine’, whose I asked, Paul’s he replied, so I’ve heard I told him.
The next day I meet Suzie and told her about the stud.
‘Come on face it Paul can get Michelle to do anything he wants’ she paused ‘I am not sure if I should say this, or if you are ready’ another pause ‘I want to move out of Paul’s’
‘That sounds like a good idea’ I ventured
‘And live with you’ Suzie completed her sentence
I was a little dumb struck, ‘What about Mike?’
Suzie stated the obvious, he was hardly ever at home, and then as if to confirm Mike’s transformation I asked Suzie Mike and Paul for a meal and brought up the idea of Suzie moving in with me, when I asked Michelle (she was in something quite sluttish, so Mike seemed wrong) she turned to Paul, who answered for her.
Apparently Michelle would be happy to live with him if Suzie was leaving it would leave extra wardrobe space and Michelle would be free to be herself all the time. Michelle never said a word, and when Paul got up to leave he told Michelle to get whatever was in my house so she did not need to come back to collect things. Then they left.
Suzie moved all her things in that weekend and from then on we hardly ever saw each other. I heard Mike was working from home a lot that meant Michelle would be fulltime, but it was a year later I got my biggest shock, we meet at a bar and she was in a very skimpy top showing a lot of cleavage. We did the pleasantries of how well each other was looking, and then I commented on his figure.
‘Do you like them double D, they feel smashing’ she boasted
‘They fill your top’
‘Paul had my bum filled as well’ she turned and gave it a wiggle, most girls don’t like their arse being big, Michelle loved it, a hollow back and round hips looked good on her.
‘Lovely, you are never Mike anymore?’
‘Never, changed my name to Paul’s and I am always Michelle’
‘And work?’
‘Cool about it, they need my skills, and cant sack me for being transgendered, so I should say thank you, it was your challenge that got me going, how’s the running and Suzie?’
So that was it Mike had disappeared, he loved being Paul’s woman, and there seemed to be no regrets from him. I had none either, earlier in the day Suzie and myself had bought matching diamond rings and were out celebrating our intention to be a legal couple.
Another one from the archives. I don't usually like domination type tales, but I wrote this in an attempt to see what I could do. If you like this theme I hope you enjoy it.
I was just surfing web sites to pass the time and came across one called Vicki Rene, and was amazed at how many men will post pictures of themselves on the internet, well I guess there were a few women posing as men, they were just too petite to be a man surely. Some were frightening, some very relaxed in their female role, some very sexy, others looked stunning in there outfits depicting a style they particularly liked, ball gowns, maids and wedding dresses were popular but a few liked period. I was impressed by a number that had outdoor shots, some in very public places like clubs, but also open streets and public areas. Anyway I was just looking through thinking whether it took courage or a sense of fun to get all dressed up, and then let someone take pictures, maybe outside, then post them for everyone to see.
Now the tale gets interesting, my partner walked in behind me with a drink for me thinking I was working hard on the pc. There was a gentle hand on my shoulder as the coffee mug went onto the desk.
'What is that you are looking at?'
'Would you believe they are men?'
'Well that one is for sure, here move over let me have a look'
I moved to one side and handed the mouse over. There were comments like wow, and that is ugly, she has to be a real girl, no way, where is his tackle, huge implants.
I drank my coffee and watched, and then she turned to me 'I have an idea for some fun, how tall are you?'
'5'6" why?'
'And you weigh?'
'9 stone something, you know this'
'yes, but have you ever thought what a good start you have over some of these cross dressers'
'no I have never thought I had a good figure at all'
'That is because you are thinking you want to look like a butch man, well I reckon we could put some pictures on here of you looking quite stunning'
I was staring hard at her, words staying in my mind not daring to come out. No reply.
'Well that's sorted we shall have you up there looking like a princess, sort you out a myspace page and see what response we can get. I reckon this could be a laugh'
I wanted to say how? I was not sure where the laughs would come from, but she stroked a hand up my thigh and found my erection.
'Now I think we should get started by getting you ready for bed'
I did not know if I was excited or frightened she had a smile that told me she was excited and that if I went with her idea it would be fun.
That night I slept in a nightie and had the most unusual sex. Before sleep took me, she was on top and rode me like I was just there for her pleasure. And strangely I loved it, she was in charge and seemed to enjoy her ride too.
The next morning she put her plans into action, first we had to go shopping, I would need a set of sexy underwear, bra, pants, suspender, stockings and if she could find one a corset or basque. Then it was round the discount stores looking for a cheap but stylish feminine evening dress. Matalan came up with a flapper style dress, straight and plenty of tassels, they also had some nice heels. Then it was back home with our purchases some quick food and get down to the planned fun.
She had been thinking out loud all morning making suggestions, running ideas through her head. These included what sort of picture pose she fancied, what sort of look we should be aiming for, what colours to use, where to take the pictures, should there be a blog to go with the pictures and many more related topics which left me a little lost as I did not know the full nature of what she was leading me into.
We started off by getting me dressed in the clothes we had bought, it all felt rather odd, the bra wrapped around my chest felt tight on my shoulders and squeezed my ribs, the knickers felt quite unsubstantial, but the stocking just felt weird as they came up my legs. The dress by comparison was just long, next she got her make up out and applied everything she had, or so it seemed, to my face, followed by a wig she once bought to see if she liked a different style, it was cheap but it was only for a picture nothing special like going out. Then the last item to make me feel even odder, the shoes, I put them on and stood up, what a weird sensation they give you, walking on your toes but not able to really get balance of your heels as the narrow heel is unstable, we were not going to be doing moving shoots so all I had to do was get to the living room and sit down.
The camera is a digital so she happily took pictures not caring if they were good or not as she deleted the poor ones without a second thought. Slowly I started to understand her instructions and how I should stand, sit or lie so I looked less blokish and a more female model. After what seemed like hours she loaded them onto the computer while I made a drink, she clearly had deleted more as there were only a few left for me to see when I got a look at the results. There was one that looked something like I could be mistaken for a woman, the rest looked good if you were wanting pictures of a man looking like a woman shoots. But she was happy, it was a start, we had worked out how to pose, what positions looked good and maybe how to improve my overall look. She redid my make up using stronger colours and restarted. This time her instructions were easier to follow and I could anticipate what she wanted me to do and soon we were back on the computer looking through the mass of images downloaded. There was not a vast amount of good ones to choose from, but she kept a couple of dozen she would look at later to see if she could think of how to improve them. Then it dawned on me this was not going to be a one off, this was turning into a longer term project until she had her pictures of me looking female and convincing, maybe even sexy. When I expressed my doubts she would ever manage to get what she wanted, she flicked to one particular picture where I looked natural, feminine and surprisingly pretty, saying that if we can get that good after only one session surely we can get some great ones as she learns to use the camera and I learn more about posing.
We were getting hungry and when I suggested I would go and change she smiled sweetly and asked me not too, but asked me to help with the tea while still dressed. With a shrug of my shoulders I said ok and went to prepare the food. I was peeling the veg when I saw the flash, she was still at it, she told me to relax and just carry on she would click away at whatever looked hopeful, this continued until I was finally putting the food on the table and filling our wine glasses, all photographed of course. Over the meal she told me how much she had enjoyed the day and hoped I had liked the experience. I had found it interesting and different, certainly I had never spent my day off doing anything like it before and it was not unpleasant so agreed it was not a bad thing to do again. That got a good reaction from her as she clearly wanted to repeat the situation.
Her side of the story
I could not believe how I felt, it was so good to be in charge. It was like having a light come on in my head when I saw those pictures of men dressed as women, I had a look at him and thought 'Yes he would be alright' Then all I had to do was think how to get him to do it.
Quite easy really, he used to be such fun but lately he had been getting duller, he is assistant manager but gets passed over for manager, he wont move for a better job, and spends most of his free time watching TV, reading or surfing the internet. And I was not going that way, I had got on well at work and had taken on responsibilities and promotion easily, what I wanted was a little home fun and this I thought could be a nice project to amuse me and maybe put something in him.
When I suggested the nightdress he agreed with a little persuasion, then I did something I had never considered before, I took charge of the love making, and he let me, even seemed to enjoy it. I planned to have fun dressing him up the next day, but after he had submitted so easily I did start to think of how far I could push him to do what I wanted.
Me again
The week turned out to be pretty much like any other week, except she brought home a few fashion magazines and would flick through them stopping and pointing at a picture 'Do you think we could copy that one?' she was still keen on getting me to look good on camera. Something else I noticed was how she would ask me to make her drinks, change the TV channel to something she wanted when I was watching something she did not like. On Friday she asked me to wear the nightie again, and again she was on top. Same again on Saturday, but this time she had me kiss her down below telling me what to do until she came sitting on my face. This time I got no relief just a thank you cuddle before she fell asleep. I got up later to relieve myself.
Sunday, both off work and she has bought some more items for me to try on. A big sleeved blouse with a fitted body, and a soft flared skirt. So I was soon dressed and looking quite feminine by mid morning, then she started to give instructions on how to sit, walk, and hold myself, gesture with hands and many other little things that she said I needed to know so I could more easily pose as a woman for her pictures. I ate lunch as a woman, then the camera came out, she was trying new things with the camera as well as making me pose in a very unnatural way, well it felt like that to me. We had wine with lunch and opened another bottle during the afternoon. I posed all over the house, on the settee, on the stairs, at the computer, on the bed, at the mirror. Finally she had run out of ideas and memory, so while I made us a meal she downloaded and sorted the images into what she wanted to keep. This time we were more successful and had several good pictures she felt good enough to go on a website. I did question whether it was wise to show the world how I looked as a woman, her reply was that we had done this after seeing the trannie websites and saying we could do better, besides who would know it was me. After tea I had no choice but to agree as she posted the first set onto a myspace site she had created for this project.
The superior person
I could see this being so much fun, I started asking for things like a coffee and he did not do it immediately but after a smile he made it. I am already thinking of things I would like him to do that I am not keen on. Next week on his day off I think it would be nice to let him cook for me.
I have never been kissed down there before, fantastic, bit selfish just thinking of me but I was knackered when I finished and besides he has come many times and not bothered that I have not.
Back to me
On my day off I cooked on my own for the first time in ages, well rather I was told to cook something nice for when she got home, so I did. She said it was so nice I should cook more often, but then she left me to clean up as well telling me she was tired and I was rested from my day off.
The weekend was pretty much like the one before, nightie wearing, one sided sex, this time she sat while I knelt before her and licked her labia, she held my hands all the time, I really wanted to help myself but could not. Spent Sunday in the big sleeved blouse and a pair of incredibly tight trousers, she said I looked brilliant and took more pictures as I did the ironing and made us our evening meal. I tried to say that she must have plenty of pictures by now, she said she only had a few really good ones, besides we were having such fun with it, though I was beginning to think she was having more fun than me.
Again my day off was spent at home, I cooked tea, and cleaned the bathroom, but when she found some dirt she told me that I would have to do it all again the following evening, when I questioned this I got a very firm talk on how I will never do it right if I am not corrected. More in shock than anything I cleaned the bathroom again the following night.
Could not believe how he cleaned the bathroom without a fuss, then when I criticized him, he objected but complied after I used my not happy voice. I will get him doing it all soon. His meal was nice which I praised him for.
A month later I realised that my mid week day off was being taken up with housework, I did used to play about on the computer or watch tv before, but now I am cleaning all day and hoping she does not have a go at me when she gets home. I am never bored now though. I am also making her orgasm every time which is quite satisfying as I did not manage it that often before all this girlie stuff started. I got a look at the website and there are some very good pictures on there, even I doubt I am a man in some of them. A bit worrying is that she has been writing a blog for me, she describes me as a cross dresser looking to improve my looks and is making up stories to go with the shots she has taken at the weekends. One mid week entry says how good it is to be able to relax doing the housework and looking forward to a girlie weekend.
The weekend did follow the usual pattern, she had bought a mini skirt for me to try out, it barely covered the stockings and when I was not careful she would snap a picture of the dark tops which for some reason I felt was wrong for me to be showing.
He commented that I was making up things about him on the blog, I pointed out that compared to what some of the other bloggers were doing he was having a quiet life but I did mention I had a few ideas for clothes and venues that I hoped to arrange in a few weeks. He did ask for more details but I passed him off with a condescending 'Nothing for you to worry about, I will sort everything out for you' he did almost come back at me, but I asked him to make me a coffee and he just went away and did it, coming back rather meekly with the drink, when I said thank you, he asked 'anything else' in a timid voice. This was a major moment for me, he had given way to me without any real opposition.
I suggested that on his day off while he is cleaning he could wear a skirt etc, he did ask why, I said it would feel right looking female while doing housework, it would also help him with his practice for our Sunday activities, and lastly because I would like to come home and see him looking like the domestic goddess he had become. And bless him I did not mention it again, and was dressed in a plain A line skirt with a cream blouse plus all the other things I had taught him about like make up, jewelry, underwear and shoes when I came home. There was even a nice meal ready to be served when I sat down.
It was half way through my day off that I stopped to think why I was dressed like a woman cleaning the house when I was on my own. She had given a few reasons why she thought it would help with the Sundays, plus she would like me too, which was possibly the main reason for me, but for the first time since the idea was first started I actually felt comfortable sat with my cup of tea and arranging my skirt around my knees. She seemed pleased when she came home, I had chilled wine and a nice salad ready for her, she told me how nice I looked and how nice the meal was and all the worries I was wrong to be dressed like this blew away.
This routine continued for two more weeks, I would even change into something dressier before she came home. When I told her what I had done she congratulated me, she was very impressed with me. Then she told me I was ready for a new venue as we had pretty much exhausted home based pictures. Come Sunday I was up early and getting dressed as she said I had to be. To my horror she wanted to be up early so we could get out before the roads were busy. I borrowed a hooded coat and tried to control my nerves as I left the front door. She had plans which she told me about on the drive out of town, I was wearing my full flowing skirt and a loose top because she wanted to take pictures of me with the breeze blowing through the clothes as I posed on a hillside at a local beauty spot. It was chilly without a coat but she was very animated giving me instructions and taking pictures. While having a warm in the car I got a view of our efforts and they looked more alive than the indoor ones, when I said they were good, she agreed and said she had other places she fancied using as a scene now that this one had been a success. But for then she wanted to take some more shots of me posing with a big shawl which would flap in the breeze, giving a Bronte look to the shots.
Her plans could not wait till the following weekend, my day off was Thursday and as was expected she came home to find the house clean, a meal ready and me dressed as a woman. Over tea she commented how the weather was dry and maybe if she cleared up I could go and change into a mini dress then we could go and do another set of shoots. I thought about saying no, but she was clearly keen, why else would she clear up when she has not done so for months, so I decided it was not worth the effort of resistance. She had me posing like a hooker in seedy back streets and industrial areas, I felt very nervous being out in what was clearly a tarty look and worried what might happen if someone happened along, or worse the police saw me. We survived and were back indoors before it was late, which was good as we had work the next day.
I had so much fun taking him outside, he was terrified but did as I asked, he is even getting quite good at doing the feminine pose, when we were outside the factory and I asked him to look at the camera and imagine he was offering sex he did an excellent job of looking like a whore, I wish a car had driven past and slowed down. As it was, I only had our car for him to lean into the window looking like he was getting business. I can't wait to post them on the site.
The next costume she got me was a frilly maid’s outfit, complete with underskirts. I spent my Sunday doing housework while she took more pictures. I had not seen the site for a few weeks but could only imagine what pictures she was putting on there and what she was writing.
The maid outfit was a great suggestion from an admirer of the website, he did look very good in a domesticated sort of way, and I am sure the pictures will be appreciated by the admirers.
I have worked out why I have been having trouble getting to look at the myspace, she has put a password on it, when I asked her about it she said it was to stop anyone hacking in and changing things. 'Like who?' I asked 'Me?' she just smiled at me as I got up to clear the table and went to my kitchen. I did get to look at the site by finding it as a guest, the pictures of me in the country, on the streets and as a maid are all there. I look a real tart touting for business, one shot I even look like I am inviting men. The maid ones have captions like domestic goddess beneath them. On the blog she is writing how much I like feeling pretty and sexy, even asks if people have any ideas for what I might do next. I dread to see what will be the responses. Some are asking where I am doing business next time, one is asking if I will go and clean for him. I am quite shocked that people actually seem to enjoy looking at me like this, more so they want to meet me.
On the Sunday she suggested I wear a turquoise billowing sundress even though it is April and not warm, she gave me a shawl to wrap around my shoulders but up on the moors in the wind it was just another thing to flap about. She has bought a new wig, long chestnut hair, and it fixes very securely to my own hair. She was telling me how much she is still enjoying this project, I said I was pleased we were doing something together, and when she asked if I liked portraying a woman, I said it was interesting, different, but to the question is it enjoyable, I said sometimes.
That evening I came into the living room to see my Y fronts being burnt on the fire, I tried to rescue them but they were all damaged. I was kneeling in front of the fire as she came in and stood over me. 'Why?' I asked and went to stand up, she put a hand on my shoulder that might have looked affectionate but I was not sure. She told me that for the pictures to work better I need to feel more feminine, that I need to enjoy what women enjoy, and that for once in my life I could do something unconventional, I could wear knickers all the time. She said 'could' but it had more of a 'would' feel to the phrase.
He did look great if a little cold up on the hilltops this morning. I had to control myself this afternoon when I set up the disposal of his horrible unsightly underpants, to have him on his knees at my feet while I told him he would be wearing knickers all the time was brilliant, I managed to stop him getting up with ease, and when I had said my little piece about why he should do it he even looked down at the floor in a quite submissive manner, I nearly asked him to say thank you, but decided against it. I am going to have fun checking he is doing as he is told this week.
I had no choice really on Monday but to wear knickers, I was constantly aware of them under my work trousers, and then when I got home she ran a hand over my bum then asked me to show her which pair I was wearing. In undoing my trousers I felt a blush come over me, it was so embarrassing, but at least I had not bought some new underpants and changed, that would have been a difficult one to explain.
Brilliant, when I asked him to show me which knickers he was wearing he actually blushed the first time, by the end of the week when I asked he just lowered his head and undid his pants so I told him that he should start wearing the camisoles to go with the knickers, without questions he was wearing a white one the next work day. I think stockings full time will be next.
It was bad enough wearing knickers, but now she wants me wear full underwear, she says it will help with my understanding of what it is to be feminine, I am getting used to the materials now and she even got me to say how nice they feel against my skin.
That was two weeks ago, now she has bought me some training bras to wear at work, but on the Sunday she wanted to do some underwear shots and while I was trying my best she was not happy with my penis causing a bump in the knickers, she solved that with surgical tape and fastened it between my legs to give a neat flat front. I know they will be on the site by tomorrow, but the worst is I can’t get the tape off without it hurting, her solution was, leave it on then I will look far better in my tight fitting clothes. She wanted sex in the evening I could not offer her anything other than petting and oral even if she had wanted penetration, but unusually she stroked my erection, it was straining against the tape already, her attention made it painful, but I sensed her get wetter as she did it, finally she pushed me aside and used a dildo to satisfy herself while I watched helpless to do anything for her.
The idea of using tape to hide his bits was inspirational, it not only made him look far better for the lingerie shots I had in mind for the site, (can't wait for the reaction of the watchers) but come the evening he could only watch as I teased him and had a most fantastic orgasm, I am sure his watching and me knowing I had made him virtually impotent added to my pleasure. My other site, the one Gail suggested I do, where I blog about what I am doing to him, will get a good reaction from this latest incident. The knickers to full underwear saga got plenty of hits, even better than the compromising maid and whore shots. I think I shall enjoy letting him watch me come some more before trying anything else, besides he will have to get used to the pain of his taped up erection and no way of releasing the build up.
The website has a last posting with me in the almost nude shots, there is one of me hands across my chest covering a none existent bust, looking over my shoulder and you can just make out the thong in my arse, and besides the spike heels I was wearing nothing else. People are already commenting about how good I look and suggesting things I might like to do, some of them quite rude. But then she has written in the blog how I am feeling sexy and ready to try something new.
I have got him taped up permanently it seems, the tape hurts so much to peel off he is leaving it on until it comes off, then I get him to tape it again next time he is having a woman day. I bet he can't even pleasure himself when the tape is off. I told him to wear a black camisole under his white shirt to work, when he asked why I told him because he should and not to ask silly questions when he should know by now I am always correct. He complained it would show through, I replied so what, he said he would be embarrassed, I just said 'so' then when he was about to speak again I preempted him by telling him I could embarrass him far more if he does not wear it. He went to work in it, I went to work buzzing, I loved the way he buckled under with my unclear threats, and I wish I could be there to see how his colleagues react when they see the dark outline. One day I will do the same but with a bra.
Getting some great responses to both sites, the Yvette site (the one I started first and he knows about) is attracting plenty of compliments from other cross dressers, but the ones I like are the men who are sending pictures and suggestions of what he should do next or what they would like to do with him. The MyGirl site is getting some seriously domineering people coming on it, they suggest bondage and pain as the only way to get total control, seems I prefer the more subtle, mental torture of embarrassment and humiliation. It does seem to everyone that he should be going out en femme as they put it, at least until he gets used to it. I have another idea though to try first.
It was raining hard last Sunday so she told me her plans for going out to take some pictures were cancelled, but I was not to let the day go to waste, I should be her maid for the day. She had had a hard week and the website needed updating, so if I could be her maid that would be great, of course I would be expected to curtsey, call her ma'am and be
there at her beck and call. 'Look on it as training so we can get some great shots of a convincingly feminine maid' I nearly said 'why? am I not feminine enough' but remembered my last opposition had lead to me going to work in the black camisole with threats of worse if I did not wear it. I do like the silk camisoles but to have it almost visible was embarrassing, I am sure Mark from household goods noticed as he gave me an odd look.
So I wore the maid outfit, she spent the morning on the computer and calling me to fetch anything she could not reach, then at lunch I made a salad for both of us but when I went to sit down I was reprimanded with a comment about servants do not eat with there superiors. I had to just stand there waiting on her till she finished, before clearing up and being allowed to eat when I had time. The worst part of the day came later, the door bell rang, until then she had always answered it and I would go and hide upstairs, this time 'Yvette see who that is' I was about to disappear 'Yvette, you don't expect me to answer the door when I have a maid to do such things. Now see who it is' there was an edge to her voice that I was becoming more familiar with lately. I just swallowed hard and went to the door, a man introduced himself as Ryan her assistant at work. That was after he had run his eyes up and down me and given me a particularly letcherous smile. I invited him in and told her who it was. I showed him through, took his jacket as instructed then went to make them a drink being formally dismissed when I returned with the tray. After about an hour of listening to them talking and laughing she rang her little bell which was my signal to enter, Ryan was leaving and I should get his jacket. He left after she had given him a particularly friendly kiss in front of me. As the door shut she turned to me and praised me on a job well done, I was a perfect maid. Then she went on to explain that as far as Ryan was concerned her husband was no longer living with her and her new house mate enjoyed role playing as a maid, Ryan had actually thought I was a woman, on the plus side, at least he did not think I was a man.
My Sunday was great, at first I was disappointed with the weather, but having a plan B is always good. He was not keen I could tell on being my maid, but that is why I do this to make him do what I want. Anyway I was having fun being waited on and asserting my authority. When the door bell rang, I was so into being the lady and having the maid do things I never thought about answering the door until I saw him heading for the stairs, and then I thought wicked thoughts. He answered the door, took Ryan's coat and brought us afternoon tea, I made some excuse about a new house mate who enjoyed dressing up and how she had persuaded me to join in the role play, I believe he accepted it. He had come to ask advice about going for a promotion, we chatted and by the end found myself thinking 'If he was not my assistant I would seriously consider going out with him' maybe it was his confidence or his physique or maybe that my husband curtseyed and asked if there was anything else we needed when he had placed the tray on the table. Afterwards I was straight onto the MyGirl site to blog about it. What did surprise me on reflection was how he rose to the situation, a strange man at the door, yet he kept in the role of being female really well even staying with the maid part as well, all that training was paying off and I told him so as he served me my supper.
As much fun as the day had been I never felt he was under pressure from me directly, rather he was complying to stay on my good side, I wanted to see him squirm again, I insisted he wore a AA cup bra too work, the cups won't show but it could not be a neutral colour nor could he wear a camisole over it, when he dithered I gave him a red one and told him it was only going to have been for one day, but as he was being awkward it would be all week. He nearly said a ‘but’, thought better of it and put the bra on, I said good in a patronizing way, kissed his cheek and left for work.
There was more than Mark looking at me on that Monday and I could not think of a way of covering up the embarrassing item for a whole week. Tuesday I asked to be let off but she just asked if I wanted to extend the time beyond a week, if so keep on moaning. I stopped. Wednesday I had been so shamed my manager Paul put a hand on my shoulder and fingered the bra strap, I could have died, so when she suggested I could stop wearing them for that week if I went with her for a photo shoot on the evening of my next day off, I agreed without thinking. Goodness knows what the nieghbours must think seeing a woman walking out of our house, it was still light and people were about but I had to do it or face the bra at work again. I was in a sheath dress that showed everything right down to suspender clips it was so tight. I had no idea where she was taking me, from the dress I thought it would be another prostitute scene because we headed into the city. Once parked I had to walk in broad daylight along a street in front of a load of bars, it was before eight so she stopped for a drink in a nice smart bar, both drinks looked the same but I could taste the alcohol in mine and hoped she was sensible as she was driving, she then started to comment on the men walking past rating them one to ten on what she called hunk scale, and when one looked straight at me she reminded me to keep my knees together. I had no idea how many shots were in my drink but I could feel myself getting more relaxed, so when she told me it was time to move on I felt quite at ease thinking how good I looked as a woman, well she had kept on saying that men were only looking because I looked hot. I followed her into a little shop not knowing what it was until I was inside. It took me a few seconds to work it out, a sex shop primarily for gays. I hope she had asked permission because she got the camera out and started shooting, my instructions were to look around and at least appear interested in the merchandise, there was all sorts of stuff there, some I knew about, others a complete mystery. At the end she picked up a few items and promised to send the owner a good selection of the photos. It was not late when we got home, so she wanted to take some more pictures using the items she had bought. First was a ten inch dildo that she wanted me to lick and suck while looking at the camera, then possibly because I had had even more alcohol, I allowed her to set me up so I was aiming the thing at my arse. The last thing she had me do was insert what she called a butt plug, it was gelled and I was relaxed so it went in easily and after the evening I had just had it seemed easy to not ask. When she asked me to lick her labia it was soaking wet and only took a few touches for her to come. She even thanked me for a brilliant evening though I struggled to see what I had done.
That evening in the sex shop was out of this world, I had to get him triple vodkas to calm him down he was shaking so much, but he did look so sexy I am surprised none of the men chatted us up. I could see in his eyes the sex shop was totally new to him which made it even better, then the shots of him playing with the toy was so good, I am sure Franco will use some of my pictures in his publicity. The plug went in so easily and I was all prepared for a bit of resistance, maybe in the morning when sober he will object.
The morning was great, he walks with his bum cheeks clenched together making him mince a little, I wanted him to challenge me then I would force him wear a coloured bra again, but he just dressed and went to work, mincing as he went.
'Yvette is looking for a new toy' was the caption over the sex shop pictures and Yvette enjoying her new toy was the caption over the next set, I can't believe how wanton she has made me look in some of the pictures, I was only posing for her. It was only a couple of day ago and already people are commenting and inviting me to meet them. She says it is great fun seeing what reaction we get, she also suggested I reply to some of the contacts and find out if they are genuine, play them along she suggests. If I don't I know she will pose as me and make really suggestive comments, so maybe I should get in before she does, even though she will be supervising what I write it might be a little tamer than her own comments.
I wish I could think of a way of losing this butt plug, it is making me walk in a funny way that I am not sure looks that good or comfortable.
Ryan got promoted, I took him out for a drink after work to celebrate, he is really good fun, amusing, considerate and not to mention good looking. I let him think I am single and he has invited me out on the Friday night.
Friday was fantastic, Ryan took me to a nice bistro, then we walked by the river, and back to his house, we had some more wine and ended up kissing but did not go all the way, it is a first date after all.
My friends on MyGirl think the plug is a good move, but I must increase the size as he gets used to each one. They also thought the bra to work was inventive, maybe I should make him wear clearly female clothes. The Yvette site is attracting some good looking fans now, I have started writing back telling them of imaginary things Yvette has been doing with her toy, though one day I will post pictures of that thing inside his arse.
I came home from work on Saturday and the first thing she said was 'Good news, Ryan is coming round tomorrow and he likes the idea of my friend who likes playing at maids serving us a top meal. I told him you would be happy to do that' I was a little stunned, first she was home late Friday night, now I am to be her maid again.
In the morning I was getting dressed as I expected her to want me to dress when she tells me to stop, that is unless I want to go to Tesco in the maid outfit, stunned again, wear your tight trousers, low heels and a vest top so you do not stand out, you dress down for shopping. I had to sort out my recipe ingredients then we went to the supermarket and bought what I needed, she lingered a little too long at the cosmetic display, and then dropped a pack of nail tips in the trolley. This day was not being at all easy, then when we got in the car she insisted we glue the nails on straight away and paint them, then they can be drying on the way home. I then had to start the meal preparations, get changed into the maid costume, and run around after her whenever she rings her little bell, and all with long finger nails that impede my movements.
Ryan came late afternoon, I had been told to be on my best maid behavior, lots of curtseys, no eye contact my face should always be looking at his chest or lower, and besides polite 'Is that all' phrases I was not to speak, in fact I was not there except to serve. I got the message and demurely served my lady and her guest until dismissed to clear up. She called me into the living room to refill their wine glasses, but I am sure she just wanted me to see her in the arms of this Ryan while he showed her a video of his last rugby match. The other thing that stung me that weekend was that she moved me into the spare bedroom, based on the convention that maids do not generally sleep with their mistresses. I was dismissed soon after the wine incident and told they would not need me any more that evening, so I went to change and had a quick look at the website, she has put on the blog that I am enjoying my toy but want to find a hunk to do it properly, and someone has offered. I am horrified that it could be suggested I might want to do such a thing.
My best weekend ever. Ryan's date. Then moving my sissy out of my bed, followed by making him shop en femme, then maid for me in front of Ryan. And then someone has offered to fuck my sissy, and I am sure he has read the latest blog and responses. The MyGirl friends want to know if I will hire him out as a maid. Now there’s a possibility.
He is walking a little easier, so when I was retaping his bits out of sight, I suggested we remove his plug and try something different, he was so slow he did not realise something different was just a bigger size. This weekend I shall get some shots of him pushing his toy up there it should be wide enough by now.
I have just had a weird Sunday, I was asked, not told what I would like to do, I was already in a skirt and blouse by this time, and I said it would be nice to just go out round the shops or for a walk like we used to do, she said fine but as I went to change she pointed out it was Sunday and that was my girlie day. We ended up walking round the shops looking at the windows, being invited by her to try on clothes in the fashion shops that were open and then having a coffee at a pavement cafe. The weird thing was I relaxed, I hoped I looked the part as I did not want to be laughed at, but at the same time I did not care if I was read, I just found myself thinking I look female so I might as well act female. Then once home she asked if I would let her do another shoot, I agreed, we did things we had already done but with different outfits, slowly I became underdressed, then the toy came out and I was licking it and so on. Next thing I am propped up on my bed, with her taking pictures of the toy being rubbed against my arse, then she suggested I try pushing it inside, the plug was removed and replaced with the toy, she seemed delighted as it slid into me, what I did not expect was to find myself enjoying the sensations of having something inside me, I am afraid my face gave me away as she encouraged me to push it further in and then slide it in and out. I did not immediately notice that when she handed me the plug to refit it, the size had increased.
Had my date with Ryan, few drinks in his local then back to his place, I did not get home till the morning, my sissy is already dressed and had not noticed I have been out all night. Oh and Ryan was a real man in bed, my little sissy was no match in any respect.
I got Yvette to fuck himself on camera and I swear he enjoyed it, I also think he is finding being a woman easier, I can see I shall have to send him out more often now and challenge him a bit harder.
I was back to walking with that clenched bum manner, that new plug is not hurting but is uncomfortable. I looked on the Yvette site on my day off, it should not have surprised me to see pictures of me showing my arse with that thing inside it, but it was the comments she had written to go with the images, like 'So much fun' 'Not quite the real thing' 'Cant wait to get a real one in there'. I actually felt myself blush at the thought of people reading such lewd comments, what was more surprising was that there were replies telling me how much they liked the shots and even a couple offering the real thing.
She had insisted I do the shopping dressed on my next day off as well as the housework. Now a few weeks ago I would have freaked at the idea of going out dressed, but now I just made sure I looked good and suppressed the apprehension before setting of for the stores.
The next day at work was a hard one, my manager Jack called me into his office, he first asks if I am alright as he has noticed me walking awkwardly, I am, telling him it is nothing to worry about, then he puts a compassionate hand on my shoulder and I know he can feel the bra strap, he asks again and felt I had to say something, so I tell him my partner and myself are trying some new things out for fun. 'So you are wearing a bra for fun?' I had to say yes didn't I. 'Is that why you are mincing around all the time as well?' I admitted to that as well. 'Sometimes I catch a glimpse of you and think you are trying to look like a girl' I blushed 'Well I will take that as a yes. Ok here is what I want........you do your job well, keep it up.............if you want to be all effeminate, then that should be fine, but be warned there are comments and gossip going on about you...........last, if you need to talk, do come here I will listen and help if I can' With that I was dismissed as I could not think of anything to say but thank you. I told her about the incident when I got home, she seemed to think it was funny that I had been outed and rather ominously said well if people know you are a bit girlie what is to stop me from expressing my feminine side more openly. When I said I was expressing it enough, she rounded on me telling that what I thought did not matter, I would do as I was told or face certain consequences. And I just caved in terrified if I stood up to her I would end wearing a full female outfit to work.
This has been a great week for him, first off I have upped the outside exposure, I updated the Yvette site with his arse pics, some predictable replies, can't imagine how he must feel knowing men want to have him. Best of all his boss has worked it out, not publicly outed him but it seems everyone has been commenting, this has got him worried and I can see great potential for fun with this area, I had to crush his minor rebellion which always feels good. Got to decide what I will do to him next.
I had a week of relative calm, nothing new, just keep doing everything she wants me to do, dress up on my days off, keep house, go to work with only shirt, trousers and shoes off the male rack. She is obviously going out with this man Ryan, I feel like saying 'What about us' but somehow I can't find the strength to say anything or the confidence to think she wants me in that way anymore.
When I worked a Saturday and she was off I came home to find several bin bags in my room, as I looked inside and saw they were full of my clothes, she came up behind me 'Well you never wear any of that stuff anyway, so I have had a sort out, left your work wear which is the only male clothes you like to wear nowadays, so you can drop them at the charity collection tomorrow' I turned to look at her 'You could say thank you for doing this for you' all I could manage was a 'but'. Then she went on to explain how on the Sunday after I had been to the charity collection point I should go shopping as I had lots of space to fill, but I should find things that suit my new personality and image. That night she went out and I cried. I was totally unable to stop her doing these things to me.
It was hard but I did take the bags, then went to the shops with her, she insisted I hold things up and show her what they looked like, then she made me go and try a blouse and skirt on, I was mortified but relieved when I found the changing was in cubicles, they did not fit at all well, but she was on a mission and by mid afternoon I had in my hands two pairs of cargo pants for work, both size 10, and the knowledge that I would not be wearing my loose fit men’s trousers in the morning. I did go in to see Jack my boss when I had a moment to ask if they were alright, he said they were but it would only encourage the gossip, I looked at my feet as I acknowledged that would happen.
I nearly had him crying when I cleared his male stuff into bags, he was on the verge I could tell, but what a wimp, he can't even cry. Loved taking him shopping, unfortunately no one guessed his true sex which would have been great to see him embarrassed but he has got so good at this being a woman no one comments. His new trousers are lovely and snug around the arse, bet it gets reaction at his work.
She has included in my routine that I shall pluck at least three eye brow hairs out every day until she says stop, and I have to leave them for inspection. I am also to wear long nails on my days off and keep my toe nails painted all the time.
She wanted me to do a maid day for her, Ryan was coming over in the evening and she thought it would be nice if I cooked them a nice meal and served them. Apparently Ryan thinks it is fun having a maid wait on him. I did as I was told with plenty of subservient gestures. Eventually I was dismissed and left them in the living room where I knew they made love from the sounds coming from there. Worse was getting up in the morning and hearing him in the house, I had to hide until I was sure the coast was clear, no way did I want him to find out I was a man, and going about in my work clothes could easily give him the truth. I was late but got away without causing trouble, just apologised.
The MyGirl site friends want me to send him out to maid for them at parties, which is tempting, one thinks I should be using more dominant tactics like kneeling at my feet, not allowing him to speak, and being more severe with punishments when he makes the slightest error. Another thinks I could make him earn his keep as a whore. But the one I am going to follow is getting him to have sex with one of his admirers, and as luck would have it a new one has turned up and I am sure he is local which would be perfect as my sissy would then be fearful of meeting his 'lover' whenever he went out.
Ryan is just so good, it is like making up for lost time now I have found a proper man to fill my hole, I can't get enough of him, the stationary room this lunch time, was excellent with a bit of excitement due to the possibility of being caught.
She has gone out for the night again but has left me instructions that a friend is coming round, I am to wear my maid outfit, I am to serve him a nice meal and make sure he enjoys it, plus I am to do anything he asks of me. I had suspected she might want me to play at maid for someone of the site, just thought she might have been there.
Well that was a terrible evening, I got myself prepared for this evening of maid role play, the food was ready, I was ready, what I was not ready for was who the guest was. At eight I opened the door to Jack, I thought it a mistake, and was thinking as fast as I could, but he let me know he was the guest when he called me Yvette, clearly he knew why I was dressed like a maid, and invited himself in past my paralyzed self. Soon the door was shut and he told me that I could take his jacket and he looked forward to a most enjoyable evening. Still in shock and embarrassment, how could I face him on Monday, I served him the food, bobbed and curtseyed as I had been instructed, then he settled down in front of the tv to watch something he liked. I thought the ordeal was nearly over but he started to make comments which I soon realised were from an e mail conversation he had had, but not with me, in which I wanted him to show me what it is like to be with a man, and as I had said I was up for anything he was going to make sure he enjoyed himself. There had been plenty of arse patting and pinching prior, but now he told me kneel and play with his penis while he watched the tv, then he wanted me to suck it. I very nearly choked when he took my head in his hands and held it still while he pushed himself in and out until he came. I was horrified when he came and filled my mouth with semen. I wanted to just get away but as soon as he stopped he told me to get him a drink, I could not even get out to clean myself up as the bottle was in the room. Then things got worse, he told me he was stopping the night and that I should go and prepare the bed, when I came down to tell him it was ready he was disappointed that I was not ready for bed as well, I apologised and went to change, I came out of my room to find him on her bed and inviting me to join him. He kissed and cuddled a bit but without passion, then he ran a finger into my arse and found the plug, had me remove it then lie face down with my arse in the air while he pushed his way inside. I would have screamed if I had not bit the pillow, it was a relief when he came and wilted.
I had a great night with Ryan, I had to use jelly to stop me getting sore. Although reading the e mail from last nights guest that Yvette had looked after was wonderful reading. He praised me on my training of such a good maid, and after I replied asking for details He replied with every detail of how he had found Yvette's sex hole. I asked Yvette about the evening and when I got limited response read the mail out loud, he stood in front of me head bowed apologising for letting the man have him. I explained that if he is to know how a woman feels he has to know what it feels like to have a penis inside him and like most women just take it and appear grateful, if he got lucky he might enjoy it, maybe even orgasm. This got a beautiful look of terror on his face.
Monday I went into work feeling dreadful, I worked trying to imagine nothing had happened, then I got a message telling me Jack wanted to see me. I was thinking I could just resign, but when I was inside the office and the door closed behind me, he chatted clearly trying to relax me. He told me how he was single and his passion was cross dressers, and right up to arriving at my door had no idea it was me, but had been tempted to ask me about my dressing at our earlier meetings. He told me how much he had enjoyed himself and wanted to know if we could set up another night. I said I was not sure it was a good idea, but by the time I had got home there was an e mail from him that she had read and replied too, telling him I was keen for him to use me for anything he fancies, and Saturday night would be a long time of anticipation but well worth the wait. He came to me the next day at work put a hand on my bra straps and whispered 'Wish I could see what you are wearing right now' I was only too pleased that he could not.
There seemed to be no escape, she was setting up my next encounter with 'my' man, while 'my' man was making suggestive comments as he quietly came to see me over something and nothing. He even changed my shift so I finished early on Saturday. The journey home was a long one as he had caught me on the way out reminding me he was looking forward to meeting Yvette later. I got home to a stern reception, apparently there had been an e mail telling me to be in a better mood later or my secret might just slip out. She asked what it meant so I had no alternative but to explain that the man coming later was my boss, Jack. She thought this was exquisite and made it clear I was going to please him any way he wanted or else not only would she make my life harder but Jack could well do far worse. I dressed in a silver lycra dress, 4" sandals and my satin underwear. I was fully kitted out with glue on nails and breasts, and she gave my make up a close inspection, insisting I thin my eyebrows even more than they had already become. Last she told me to remove the plug and fill it with jelly. I was ready and it was only seven so had time to sit and consider how I had come to be in this position. I did not ponder long, Ryan turned up and after a rather long and intimate kiss with my wife they left for their own evening of pleasure. Jack turned up as they were leaving, she quickly realised who he was as she had meet him a couple of times, they passed a few pleasantries, he said that he hoped she would have a good night, she said she would, and that I had talked of nothing else but tonight so she knew he was going to have a great night.
Once inside he kissed me rather more passionately than I expected, and was rubbing his erection on my thigh. 'I have a table booked for later, but right now I would like you to have a little drink and relieve me of some tension, if you know what I mean' I knew only to well what he meant. I unzipped his fly and knelt before him. Job done he thanked me while I checked my make up in the mirror. He even told me how beautiful I was looking and could not wait to show me off to his mates later. The meal was a standard Italian, I remembered all my teaching and behaved like a good girlfriend, then he took me to a bar which I recognised as one of the gay ones she had taken me to in the past. It was here where he showed me off to his friends, who took delight in asking how he had managed to get such a gorgeous girl, they accused him of paying for an escort, but that stopped when he quietly told them I was a man, I could have died, but they were all in shock almost insisting I lift my dress to prove it was true. I could do nothing, he had his arm draped over my shoulders or around my waist in a very territorial manner. He did keep buying me drinks which meant as it got later I became more unsteady on my already difficult shoes and had to hold onto his arm for support. Eventually he took me back to his house and told me go upstairs and prepare myself for the evening’s finale. I knew what was coming and obeyed by finding the bedroom and removing my dress and shoes. Then as I pulled the sheets back found a white silk nightie, I undressed completely and slipped between the sheets in the silk nightie. He came in and smiled a letcherous grin and climbed in beside me. This time I lay on my back and he took it slower, he could see from my face whether he was hurting me and said he did not want to make me scream in pain only pleasure. His self control was excellent, but eventually he came inside me. It was now late and he was still wrapping his arms around me. I decided I might as well try to sleep and go home in the morning. Something I was to discover is called the walk of shame as you walk home in your evening out dress looking quite out of place in the morning.
That was a great Saturday night not just because Ryan was good, I got to go on top for the first time, he is not quite the same as Yvette was but I do wonder if he would be as cooperative as Yvette has been.
Yvette did the walk of shame, silver mini dresses do look so out of place at nine o'clock. We were having a coffee when Yvette came back, looked ok in a sort of 'in need of a good clean up' way. I asked if she would be a love and make us some breakfast, she just went straight to the kitchen and did it, then fetched it in on a tray, with a little bob and asked permission to get changed. I dismissed her and the next time we saw her she was in her maids outfit. Excellent, he did that change without prompting.
I read the website later and saw the posts from her male companion for the evening, nice to know he had a good night and that Yvette was such good company. I wrote back as Yvette telling him how much fun the night had been and was looking forward to seeing him at work on Monday, and asked if he wanted to arrange for another date. I then went to his room and removed his work trousers, replacing them with size 10 women's work trousers we had bought him.
Monday was another nightmare, first I could not find my work trousers but when I saw the new women's pair I knew that was going to be my only choice, I also looked a sight in the mirror as my eye brows were now clearly a fine line over my eyes, not even a hint of masculinity there. In work Jack complimented me on how good my arse looked in the new pants and saying he would be in touch when he has thought where to go for our next date. As for the rest of the staff I am feeling more and more isolated, either I am so ashamed or nervous about the way I look, or they are keeping their distance, but I hardly speak to anyone except for purely work related things. Sometimes people say things about how I look, today Jane told me the trousers were nice but I could not tell if she was being nice and complimenting me or being horrid and teasing me. In a way I looked forward to my day off and the dubious pleasure of wearing a skirt.
Saturday evening found me dressed as Yvette again and waiting for Jack to pick up his date, we were going to the pictures and I was in a cream blouse and brown pleated skirt, quite modest I hoped. He looked disappointed and told me to go and change into something more appealing to him and not me. I returned having changed the skirt for a green mid thigh skirt which just covered the stocking tops. This got his full approval and we left for the cinema, but not before he pointed out how my inappropriate choice of clothing had deprived him of a blow job, he said I could make up for it later. Which could mean many things but all would involve sex.
I was getting bored with Yvette now, I had taken all the pictures I could think of, short of public shaming which might come back badly on me, I could think of nothing to increase my power over the sissy. I had achieved more than I had expected and created a totally subservient, totally convincing she male who was not only embarrassed about how he looked but simply accepted any changes I made to that look. The best was when Jack made a date and Yvette was dressed to kill, he looked beautiful and though I knew he was acting did appear to be enjoying himself even to the point of publicly kissing without Jack forcing himself on Yvette. It was something about the way he seemed to initiate the kiss that looked so convincing.
I have had 2 months of nothing new to add to the website, nor change in my sissy's appearance, his own hair is getting long enough to be styled and maybe I could change his shirts for blouses with Jack's assistance, maybe he could wear some make up to work, but quite frankly I am bored with this now.
My nightmare continued on a daily basis from then on, at home I had her treating me like an object, do this, do that, I want a maid today, and I was expected to do it, and I always did. At work I felt more alienated by the rest of the staff, Jack made it clear he quite liked the feminine style I was arriving at work with and told me to maintain it, even making suggestions of his own, but not with the menace I got at home. My 'dates' were mostly with Jack, but there were others she set up off the website, becoming almost normal. Finish work, home, change, date arrives, go out, have sex, come home. Very predictable.
Then Jack suggests a change to the routine, he fancies a maid going round to his house once a week and giving his house a clean. He set this up via e mail through the website and she just agreed to it as long as I still kept our house clean as well. Jack rearranged my shifts, he said to help me, but I reckon to please his plans really. I would be finished mid afternoon on a Friday and Saturday which allowed me time to get changed if he wanted a date, and the day after my mid week off day would be a late start which I later found out meant I could spend the day at his house cleaning, then spend the night there and have time to clean myself up before work. So considerate.
My first week as his maid I turned up with a key and let myself in, changed out of my hipster jeans and top into the maid dress and made a start on the cleaning. By late afternoon I was pretty much done and had prepared the food he had left for the evening meal. He loved the fact he could just come in, instruct me to get him a drink, fetch whatever he wanted and serve his meal for him, and then when he wanted just take me sexually. In the morning he told me he had really enjoyed having me around and would like to make my maid visit a regular thing. She said it was a good idea and why did I not go from work the day before as well and spend two nights there. Jack was all for this and made sure I was set up when I went to work the day before my next day off. I had to get to his house, become Yvette, cook a meal and have sex, the next day clean and do anything else he wanted, before going to work the following day from his house.
I was beginning to like Jack more as the weeks passed, he was kinder than my wife though he did like to do what he called training. As a maid he would at times have me stand completely still for ten, fifteen minutes, sometimes longer, the other one he insisted on was that I sit correctly, which meant on the edge of a chair with my back straight, hands in lap, feet tucked beneath me. Early on I discovered he did not use idle threats, if he said I should do something and I did not, I would pay for it. This could be a smack, being told to wear something feminine to work, not being allowed to eat, or being forced to stand by fastening me to a hook on the wall, preventing me from sitting down, and having to stand in my highest heels, then he would go out for a long walk. By the time he got back my feet, calves and back would be killing me because of the high spike heels he always insisted I wear. As he released me he asked if I would do as I was told, off course I said yes, anything for relief.
To my utter shock I soon found myself sitting correctly at work, and when I lifted anything I did it like a girl, crouching down rather than bending at the hips, not wishing to show non existent knickers. What was even worse when I slouched back in the chair it felt uncomfortable and wrong.
Another shock was to realise half way to work that I had used lip gloss instead of a chap stick for my dry lips in the morning, and it would not easily clean off, she always insisted I use long lasting lipsticks that will survive a kiss. When Jack noticed he said it looked good and that I should continue to wear it. Meaning not just the rest of that day either.
But the biggest shock came after a Saturday night out, Jack had taken me out to a nice restaurant, I had been allowed to wear feminine instead of sexy that evening, and when we got back to his place found myself very relaxed in his arms. When he got me into bed he took it really slow and seemed to be more considerate than usual, even asking when I last had an orgasm, sadly with my penis taped out of the way it had been a long time I admitted. That night he made me experience a new sensation, his penetrations touched something inside me and stimulated a cascade of tingling and relief that was totally new to me. After I had stopped panting and he had withdrawn from my hole, he said to me 'Tonight we made you into a woman, did you like it?' and still coming down from the high I said yes without thinking. This was quite a revelation and a dramatic new turn in my expectations of what this role was doing to me, plus a more positive attitude towards my situation.
I can't make up my mind whether I like having Yvette out of the house several nights a week, I get some time to myself, but I miss having him make the tea and things. I also had to take a double look last night, he was sat as he seems to recently, all prim and proper sat upright on the edge of the seat, but what really took my attention was he had been to work and he had lip gloss on. When I challenged him about it, he admitted that it was lip gloss and explained the story behind it, saying that Jack liked it so he had continued, when I asked what else Jack liked for some reason he blushed, I then asked if he was getting to enjoy being the woman, his silence spoke for volumes, before this moment I was sure he would have quietly said no which was part of the fun in making him do it. I almost told him he must wear mascara to work but felt no buzz in the idea, he might actually want me to tell him to do this, and where is the joy in him not squirming.
That week he stopped at Jack's for his usual mid week maid time, but he also stopped Friday night and did not come back till Sunday night, when I asked what he had been doing he said Jack had kept him too busy to come home.
Not only am I getting bored, there is little fun in his situation, and added to that I am losing my position as alpha, to Jack.
Jack has been so nice since I had that orgasm, he still likes me to dress for him but does not say anything if I wear something to please myself, cleaning is so much easier in jeans, mini skirts are not right when shopping for groceries, but a night out at a club is definitely his choice, I even encourage him to choose by parading before him in several choices, then sucking him when he has decided, this game seems to be a hit with him.
Last week it felt like I was at his house all the time, I was his mid week maid, then when we went out on Friday I went to work from his house, then spent the Saturday evening at his house doing what he called training, which mostly involved me being dressed in sexy underwear and heels, then running around after him or sitting at his feet while he stroked my head, followed by his taking me shopping on the Sunday for new underwear, nightwear and heels, which he asked me to try on for him to have a look at, then took me to bed before I went home late Sunday evening only because I needed clean clothes for work on the Monday.
It was a Thursday evening, I remember it well, Yvette had cooked a nice carbonara, the door bell rang and she went to answer it, there was unexpectedly some chatting then the door shut and she brought Jack through, she bobbed in front of me saying 'Ma'am, Mr Speding to see you' I waved Jack to take a seat while I finished my meal telling Yvette to serve Jack with some wine after he refused a serving of pasta, it would have been Yvette's later when I had finished but I was happy to appear generous with his food. After some polite chat he got to the reason for his visit. He wanted to know if Yvette was free to leave or would there be any conditions attached if he left. I was a little surprised by this so questioned a little, turns out he has a promotion some 100 miles away, he will be taking the job but wants to know if he can take Yvette with him, out the corner of my eye I could see the sissy itching to say something but Jack gave a look that made him stand still and bow his head slightly so he looked completely demure as he clasped his hands in front of him, all the fidgeting gone and eagerness to say something suppressed. We then started with what I would have called at work, negotiations, but over a glass of wine seemed more like discussing selling a car to a mate.
I did not let him know I was tired of Yvette but quietly liked this new turn of events, I said my main concern was that I would need to take on a house cleaner, and that I would lose a good cook. Jack offered me a few thousand pounds cash and he would pay for the divorce I told him I wanted, the fact we were married took Jack a little by surprise but a quick look at my husband reminded this man that there was little if anything left of my marital partner.
He wrote me a cheque as part payment and told me he was moving that weekend as he started work on the Monday at his new job. Yvette's notice had already been submitted and accepted, so would need to pack and be ready for his picking Yvette up Friday evening, all a bit quick I said but I was looking at a nice cheque, and a rather pale but silent, soon to be ex husband.
Jack left, Yvette showing him out, when he came back I told him how he should be grateful someone wants him, and flattered they are prepared to pay for him. I swear I saw a tear in his eye, maybe he still felt something for me, unfortunately I felt nothing but contempt for him now as he stood there head bowed and no fight in him. My last words to him were that he should clean up then go and pack everything, and to leave his room spotless when he left, if I found anything after he had gone I would not send it on, I would just bin it.
As a last chance to exercise my power over him I stayed off Friday morning so I could make sure he only took suitable Yvette clothes, I had trained him to be feminine so he was not leaving my care with anything he might consider even close to masculine.
Friday evening I got home just before five, to see the final step in his female life with me, and as it turned out a rather sweet moment where Jack gave me cash and we I signed over my claim on Yvette the maid. Well I found it sweet, I doubt the sissy did, but I was unconcerned about his feelings.
When they had gone and I was enjoying the quiet of the house, I noticed on the table was an envelop, inside a note and his wedding ring. His last and infrequent act of rebellion the note said 'This is the shackle that held me to you, it no longer means anything.' but he had signed it Yvette, then I noticed a bin bag by the door, a quick look revealed it was his male clothes, just work shirts really, plus the other items I had deemed unsuitable, but still significant. I smiled to myself I had achieved my goal of creating a completely femininised man who did not want to be seen as a man but preferred to be a girl.
This is the first time I have had chance to write anything down. Last Thursday I was doing my usual evening routine, cook for her, serve it and wait till she had finished before enjoying my meal before doing some feminine treatment to myself, then bed after making sure she has all she needs. This Thursday was normal to start, she was eating when the door bell rang, I opened it to find Jack stood there, I asked if he had the wrong day, he said it was Thursday but he had not come to see me, this was business that needed sorting with the lady of the house. I then realised my place and took him through and introduced him to her as she had taught me. I stood to the side and waited for my next command. They sat drinking wine being polite to start with, then Jack came out with it, he was leaving the area and wanted to take me with him, but I was not being included in this conversation, as they discussed my future I wanted to ask if I had an opinion but Jack gave me a look that meant 'don't you dare move' he had used it when he was 'training' me to stand dutifully beside him while he thought what task he wanted doing next, and this time as every time before I lowered my eyes and stood upright and still, my obedient maid stance. From this position I heard them negotiate a price for me as though I were an object, a piece of meat. He eventually agreed to pay her for a cleaner, and when she suggested he pay for the divorce costs he took a quick look at me, smiled and agreed. I had been sold and without a say in it. He then explained the timetable, I was to have everything ready for him collecting me at six the next day, he had already sorted out my resignation from work, so I was to be his personal maid it seemed and I had to just accept it. Funnily enough by the end of the day I was happy to be going, she made it clear that I was a joke to her and Jack was welcome to me, she wanted a man not a sissy, but she still made me clear up and before I could go to bed I had to make her supper, prepare her bed, get her clothes out for the next day and sort out her dirty clothes from the day.
I spent the night wanting to get my own back on her for what she had done to me, but the best I could do was write a note telling her my wedding ring had been a shackle.
The next morning I was surprised to find that she was not going to work till later, I had to make her breakfast, then she supervised my packing, clearly any male clothes were separated and for the bin, but she also picked out the more modest items of female clothing that she considered androgynous or in some way unsuitable for my new role, such as flat shoes, leaving me with only heels which she said would be more appropriate in my new position as live in maid and sex object.
He came at five and was clearly more relaxed than the night before, I was in a neat suit and heels, he kissed me this time when he came in the door, 'Looking forward to this?' he asked 'yes' I replied. Then the most humiliating thing ever to happen occurred. Jack took out a wad of notes and handed them over to her. Then they both signed an agreement which I managed to get a quick read of. Briefly it said that she had no claims over me from that date, and that Jack had complete control and could do whatever he wanted with me or to me, and I did not even get a say in this, sign anything or agree to any of it, but like the night before I stood quietly to one side not prepared to rebel. Deep inside I knew that even if I wanted to change things, I did not have the inner strength to do anything other than what I was told to do, I was his to do with as he pleased.
He then took my bags and loaded them in the car, a curtain across the road twitched as it often did, and for the last time wondered what they must be thinking of the goings on at number 32, I waved knowing they were watching. 'Right I have still got things to do locally, my house is packed up, so while I am running around I have made an appointment for you, I will not accept any of this being a part time woman, you are going to be restyled to be my Yvette' I looked at him 'I expect you to thank me for it later' all I could manage was an 'oh'. He continued 'Women like to be pampered, and you are now my woman so you going to be pampered, enjoy it!' Without knowing but guessing what was coming he dropped me at the door of Women Only and told me to just give his name when asked for a booking reference. Five minutes later I was at the back of the shop having my wig removed and my true identity revealed. This was no ordinary salon, I was reassured I was not their first she male and I would not be the last. First my hair was washed, conditioned, trimmed, coloured, styled and set into a short out flick bob cut. My nails were sculpted as they called it, into 10mm talons which were painted a deep pink along with my toes. My eyelashes were tinted dark brown, along with my now neat eyebrows. Finally they redid my make up using top quality cosmetics which they told me would not rub off easily, and the lip cream would help to swell the lips making them plumper. Finally they told me Jack had pretty much given them a free reign over what they did but he had insisted on three piercing, I expected my ears but when they inserted a stud in my nose, then another in my navel I had no idea where the last would go, that was until they asked me to stick my tongue out, in anticipation of the pain I gripped the chair arms, it was painful and immediately rendered me unable to speak, I must have looked frightened but they reassured me with painkillers, and then adviced that a stud there will make any man do anything for me if used correctly.
Jack turned up on time and gave me a kiss which made me flinch, which made him smile, 'You had it done then, it will be great when the swelling goes down' I mumbled a yes and got into the car.
The 100 mile drive to his new home was a quiet one, it was late and I could not speak easily just letting the miles drift past. Our first night was in a hotel, the removal men would arrive the next day and my job was to make sure everything was put in the right place and to start unpacking, Jack was going to work, making it clear from the start that the house was my domain.
It took almost a week before I had unpacked all the boxes and got everything in place and sorted, by which time my tongue had recovered from its injury. It was the day that I realised he had not had sex with me since we had moved and was thinking it unusual, but on reflection this was deliberate, as later that day I came over quite funny, Jack said he was taking me to the doctors when I mentioned it, but then the next thing I knew I was in a private hospital room with bandages around my chest, a sore neck, sore face and sore heels, my whole body felt as if it had been pummeled really. The reason for these bandages did not take me long to work out, I had had breast implants along with what I guessed to be other procedures to create his female image for me. Sure enough, my adams apple had been shaved, any remaining beard had been removed, when the bandages came off I had a generous chest I was told should be at least a D cup, liposuction had slimmed my waist, and filled my bum, the soreness in my heels was caused by the shortening of my achilles which would mean I would find heels more comfortable than flats. If I ever wanted to go back I would have a real challenge on my hands, but I still had my penis. One night a few weeks later after I had been practicing what the tongue stud could do, I asked him about this. He told me that to have removed it would have made me a woman and he wanted a she male, and that if I wanted to use it then that was fine but only on my own, I was his exclusively. He also told me I could choose whether I tucked it or not, maybe when out and about I would want to keep that hidden from view, but in private he might even like to see a bump in the front of a tight mini skirt, and if we ever went to a gay night out my male vestige being visible could be quite attractive he felt, and intriguing to any one who observed that I was sporting boobs and a prick.
Jack was not to demanding when I first got home from hospital, I rested a lot but would have his meal ready for when he came home every night. Then as I got stronger and got the house clean again, and myself back to the feminine image he desired. So I started to work out what I could do with my new body, image and role. I could not see myself as a man anymore, even if I could stand to pee, buying my new DD bras made sure I was constantly aware of my new body. I would walk around the house of a morning barefoot but I still found myself keeping my heels off the floor and walking on my toes so I would almost see heels as a relief. That was a clever plan on Jack's part I often thought as he does like women in heels. He also gave me housekeeping and an allowance, at first I planned on saving as much as possible so I could one day use the cash to escape in some way, but as the savings grew things changed, I would see a new fashion and find myself trying on a different style of skirt or top, then thinking it will keep him happy and not suspecting if I buy new clothes, but it was when I started buying for the house that I began to recognise that I would not be leaving any time soon, first some curtains, then paint and when he offered to buy new furniture and I choose a real chintzy style, he let me know that he had no idea how anyone could ever consider me a man. I shocked myself by being inwardly pleased with this comment and made sure he fucked me well that night so I could enjoy being his woman.
One year on from the day I was bought by Jack and I can admit to it now, I enjoy being seen as a woman, I enjoy being Jack's partner most of the time, I like being a housewife/ homemaker, I look forward to romantic evenings, I can sometimes yearn to have Jack inside me so much I can think of nothing else.
There have obviously been costs to pay both in money and the lose of the person I was to achieve this, my previous owner (because that is how I see myself now after cash was paid for me) clearly had a big part in my initial transition, but Jack has taken it further and reinforced the role he wants for me onto my personality. Usually he has done this with a carrot, for example, he wants me to look sexy but classically stylish when we meet some work colleagues, he flatters me with a salon and new clothes making me feel a million dollars. But at other times he can be harsh, if his meal is not perfect, or I am not responding to his sexual advances how he wants, maybe I just wear the wrong outfit, whatever the cause, the punishment can vary, being easy or difficult.
Once when I wore what he thought inappropriate he decided I should walk through a busy shopping precinct in lycra trousers with my penis up front, my feet teetering on the highest heels and my chest stretching the tightest top. I dared not look at anyone fearing that every laugh was at me. This woman has a most obvious male bump. I was so embarrassed by the time I was allowed back into the car and could leave.
One time when he thought I was not responding to his advances well enough, deciding I needed time to enjoy sex more. So he tied me to the bed and took me from behind. Then left me there to consider my position with him, I did plenty of considering while a vibrator buzzed away inside me. He came back later for another screw to find me exhausted, but happy to let him have me and give me a rest from the mechanical stimulant.
One of the most humiliating things he does and without cause from me, is to go out of an evening to a gay bar he likes, making me dress in my most revealing outfit, with my male bits causing a bump, then he will put a collar round my neck and attach a lead so he can walk into the bar with me dutifully following him, sometimes he even takes handcuffs and secures me to a wall while he goes off with one of his friends.
These events have been rare and mostly I am allowed to dress like any normal woman might who is looking after the home, maybe a bit more dressed up than most, but that is my choice and definitely nothing outrageous in the daytime, I save that for the night time.
It is a year since I signed away my marriage partner, I was so smug with myself then about what I had done to him. Now I wish I could turn the clock back a few years. Ryan was good but I started to hanker after that control I had had over Yvette, he let me ride him occasionally, he would even wear knickers for me, and I was getting some way with the simple tasks I did not like doing. I am not sure how he found out about Yvette, but when I asked him to wear knickers a fortnight ago, he asked if this was why my husband had left. Anyway as the topic developed, it was clear he knew far more about Yvette and my marriage, and rather than sex that evening, he became my ex.
I was rather stunned by events, Yvette had been uncovered, and I had lost my lover. Worse was to come, Ryan did not gossip but when it became common knowledge that we had split up, some bits slipped out and though no one ever knew the full story, I was branded a domineering bitch. It damaged my work relationships, ruined any chance with any men at work, and pretty much isolated me.
So for now I have to do all my own housework, and tip toe around at work careful not to get some snide comment.
I think I need a new start, and try to learn from this, but it was such fun creating Yvette, I fancy having another go if I can find the right man.
There are many programmes out there that allow you to manipulate photographs, some might say improve on the original. Magazines do this with their models to create perfect skin etc. But what if those changes affect more than the skin and go deeper?
Having sold my business, and having enough pension to live off I only wanted some part time work for pocket money and to give me something to do. So when a friend asked if I would help out with his photography work I did not ask what was needed, just said yes.
The work was mainly school photos, weddings and the occasional studio family photo shoot. So I would help with the equipment and directing people to their positions. Paul was easy to get along with and I always enjoyed being asked to help, he was the expert but would ask my advice at times about which picture looked best if there was a choice.
So life was fine, that was until Paul got some new software. As he was learning how it worked from scratch I was able to keep up with his learning and became involved exploring the possibilities. The idea was to use it so photos could be improved by removing blemishes from the subjects, or maybe highlight certain parts by altering shadow or colour. The basics we soon mastered, and we could do small adjustments. Then Paul started experimenting by altering pictures of us, he would change skin tones, increase beard cover, alter hairstyles. It was as he increased my hair to shoulder length that we both noticed what a dramatic effect it had on my face. Paul then went off to an appointment without me so I stopped to play with the images. I had always wondered what I would look like if I did things differently, and this was a perfect opportunity to find out.
I am not sure why but I tried a few hairstyles and found a long fringe sweeping across the face my favourite. Then after a break to make a drink I came back to the image and realised how feminine it looked, so I played with the image some more, the eyebrows thinned nicely, I was able to add colour to the eyes, lips and cheeks as well as changing the overall colour of the face. It was so absorbing the time passed really quickly, and Paul was back from his last job to find me still playing. We had a good laugh about what I had done saying I had turned a Jim into a Jem.
We did not meet up for a week or so after that, but when we did Paul wanted to show me what he had done. He had proper studio shots of a woman in evening dress stood next to a smart dressed man. I looked closer and saw the man was Paul and complimented him on how good he looked and asked why the photo and who is the lady, and was it a special occasion they had been out on. He just told me to look more closely, then it dawned on me the person in emerald green gown was me, well at least my face. Paul stood back and grinned, obviously pleased with his creation 'so what do you think?' 'Very clever, I look different and you're not so bad yourself'
We spent a long drink discussing how he had done it and what else he might be able to do. So when he left me to mind the shop I had a play myself, I tried making Paul look female but he was just wrong without changing his face shape, so I went back to me and searched the archives and mixed my image with different clothes.
Over the next weeks then months we got really good at making little improvements, the odd mole disappeared, stray hair on an otherwise great photo was brushed away, the shadow of a tummy bulge faded to create a flatter stomach, the instant diet, whites of the eyes became white not yellow or bloodshot with just the click on a mouse.
The original picture of the pair of us was improved on, and became quite a good selling tool to show how much we can change the image. We were surprised when one customer actually called in and asked if we could 'do' him as a her. He seemed genuine, had a set of photos taken, paid up front, and left us to 'improve' them. It felt a little weird but I did a set for him, he asked for a cocktail dress, an office outfit and most odd to me a wedding dress. He called a week later to pick them up and was simply thrilled, and asked for one more to be done. Could we merge a picture of his wedding dress image with him in a suit stood together as man and wife as it were? No matter what I thought he was paying, so I told him a week and call back. A week later he returns and loved the wedding day photo. To say my curiosity was on full would be an understatement, so I chatted for a bit, then as it was late, closed up and asked if he fancied a drink in a pub nearby.
Well I got his full history about how he likes female clothes, and wanted a picture that was perfect. He did not have the nerve to find someone to do the whole thing for real with, so we offered second best. He then got around to asking if the emerald dress that I 'wore' was real, when I said it was not, he looked quite shocked, and insisted I was a naturally feminine featured person. After a while the subject moved on, and we went our separate ways, but the conversation kept playing over in my mind.
The next time I was with Paul and not rushing about but drinking a coffee, the subject of this man came up, so I recounted much of his tale and what else he had said. To my surprise he agreed how female my face is, I asked if he was going weird as well, to which he laughed.
Business continued, I was becoming more full time than part time, but enjoying the new skills, and enjoying the thanks customers gave when they saw the improved photos. Then Paul told me he had a job doing some publicity shots for what he called a dressing service, our bride had apparently been telling his friends about us, and this had generated the enquiry. They wanted a set of images from male to female, they had a model, but they wanted to emphasise the maleness at the start and improve on the female with the final picture.
So Paul took the set, as the man was transformed into a lady with lots of pictures showing the changes. Then after the best had been chosen, I set about improving them, the first picture of the man I made rough looking, he had not shaved, but I darkened his skin a tone, the bags under his eyes deepened, his eyebrows grew some extra hair and so on, the pictures showing the work of the dressing service did not really want any attention, but the final one I made sure the face was faultless and his dress, a lovely burgundy velvet tube was perfect.
I was particularly happy with the results, and so were they. It was some months later I went past their shop and saw my handiwork displayed in the window showing the transition of the man, and felt oddly proud.
Paul and I occasionally had conversations about these odd jobs that came in, sometimes they were pictures already taken that I improved others were for a complete works like the first man. But no matter how much we tried to work out what made these men tick, we never really got it.
So after one really nice gent had asked us to alter his image so he looked like a secretary, I made up my mind to find out for myself, he seemed such a nice bloke, as they all had, so I asked where he gets his clothes from. I was shocked when he said department stores, but he did admit to using the internet at times if he knew exactly what he wanted. He even offered to come with me shopping, but that was too far for me and declined his offer. The thought of me and another man going in to buy anything female made me blush at the thought.
So I went on e bay and ordered some knickers, then spent two days worrying someone would find out it was me who had ordered them. They arrived and I can't tell you how nervous I was opening the package, I went through the whole range of chuck it before opening it, right to getting them on as quick as possible to find out what all the fuss is about. In the end I opened the package, ate my supper, then tried on a pair. It was at this point I was hooked, silk French knickers gently sliding up my legs, then coming to rest on my hips felt to wonderful for words, they were beyond comfortable. I remember pulling my trousers back on which just added to the feel of silk on my arse.
Next morning I dressed as usual but this time without my underpants, I wore the black silk all day. Besides the feel of the knickers, there was also a subversive thrill of doing something I had always told myself was wrong. And so I was hooked. Later that day I ordered more underwear, different pants some thongs, some control and some camisoles to match, well it was cold and I should wear a vest I jokingly told myself.
Within a month I had to move the male underwear out of its drawer to make way for my knickers. The next thing to go was night wear, I always wore cotton pyjamas, so first I ordered a green satin set of pyjamas, which felt so good I would change for bed early just so I could sit around in them, then as I thought of getting a second pair I saw a red silk nightie, ankle length with a robe to match. Two days later I was sleeping in it, a week later I had bought two more.
For a month I hardly bought anything, but wore my new clothes constantly never once going back to the male thick cotton things of the past. They still felt great, but at times I would forget then a movement would remind me what I was wearing and I would smile to myself.
At the end of the month I was looking at a lingerie website and had a coffee in hand, before I clicked on the 'submit order' I paused and reflected on the last four weeks. I tried to answer questions such as what was I doing, why was I wearing a pink thong at the time with a matching camisole, could I stop if I wanted to, did I want to stop, what would happen if I was ever found out. I sat back unable answer any of the questions, except to confirm in my mind that I enjoyed it, and the thought of being found out added an extra thrill. The coffee finished I clicked the mouse and ordered my first bra, only an A cup and with no real idea if it was the right size, but the white lacy garment that had no male equivalent would arrive shortly.
Another decision I made about that time was to not have a haircut, for months I had been intending getting a trim, but being busy I had just not got around to finding the time. I was already constantly flicking the fringe back and pulling it out of my collar when I put on a jacket, so the idea of getting a short cut again seemed the wrong way to go.
The bra came and as I put it on I wondered if I could wear it to go out in, I settled for a sweat top as it is baggy and thick, the cups filled with my small fatty lumps, and did not stand out more than before, so I decided to go to the studio in it and see how it went. Paul never made a comment, and it did not seem to be obvious at all so relaxed and enjoyed the new garment and thought of what style to get next.
A week later I had five more, lacy, satin, under wired and sport, I even tried them under a shirt. At first I thought they would be noticed but Paul said nothing and nobody seemed to stare at my chest, so I assumed I was ok.
Wondering what to try next, I lay in the bath looking at my legs, and recognised that women are always clean shaven, so with time on my hands I started filling the bath water with leg hair, then I trimmed the pubic area, next my arms and last my arm pits. It had taken ages but once dry and warm it felt good. The decision was made that at least once a week I would shave unless I felt stubble before.
I was now well into my new hobby, and while I did consider what might happen if caught, I became more casual about what I wore. I bought a new t shirt but instead of the baggy men's variety I choose a nice white fitted ladies style, the two things I noticed were how well it fitted my body and the other was how short it was, this would never tuck in and stay in. but I never wore it as an outer top so nobody need know, or so I thought.
Next I bought slippers for the house, nobody would ever see these so I went mad and ordered a pair of fluffy pink wedge heeled mules. It was such fun to mince around the house doing whatever, with the slippers on my feet.
At some point after the mules, I painted my toe nails for the first time, just a pink colour then, but within weeks I had changed the colour so many times I could not remember which I liked the most, and was applying clear buff polish to my fingers as well, which three weeks later instead of cutting I was filling to get a nicer shape.
Then I almost came out to Paul, I had an image of me on the screen and was changing the hair colour to see how it changed my look, and asked Paul what he thought of a lighter shade, he looked at me oddly and asked why I should want to colour my hair, I tried to cover up saying I was just curious and playing around. Then to my surprise he takes the mouse does a few clicks, lightens the hair a few shades and says 'something like that would probably be best' and walked away leaving me to decide what he meant. I noted the colour all the same. The next day Paul casually asked if I was thinking of having a haircut and was the colour thing connected, seeing no real way out I agreed it was getting untidy. Then he goes on the computer and pulls up the first picture he had done of me on the green dress, and zoomed in on the head. 'You could have it in that style I should think, it's long enough you know' my throat went dry as I struggled to find a reply in my racing mind, all I could squeeze out was 'do you think so?'
'Do what you like, your ends are splitting, and I am sure you would like a new style' was his unexpected reply.
It was nerve wracking just making a hair appointment at a unisex salon, but going in and then being asked about how I wanted it to look was far beyond my experience of barbers, luckily I took an image of the style and in the shade I hoped for, so the nice patient lady was able to sit me down and get on without getting me any more worked up. It was nearly a copy of the picture, I had collar length hair, side parted with a fringe that swept across my face and ear. Julie (the nice patient lady) sold me a jar of gel so I could remodel it the next day, though I was unsure I could get the same volume or easy sweep that she had created. But for then it looked great.
I had a nervous walk back to my car wondering if people were looking, but after a while convinced myself it always did feel odd after I had had a haircut especially when a fair bit had been trimmed off. The evening was anything but restful either, I knew Paul had sort of encouraged me, but I now had the hair we had put on a woman's image, just how would he react?
The worry was wasted, Paul hardly looked up, just said hello and asked if I would make a coffee. It was later over lunch that he asked how I liked the hair now I had it for real, was the colour right, did I like the fringe? This all left me asking myself if Paul minded how I looked at all, I knew that a trip to the club would be difficult, drinking pints and playing pool would not be the place to ask how friends thought the new style looked.
On the Monday Paul asked what I did over the weekend, we nearly always meet up with friends for a drink, maybe golf or a hike, but I had avoided the friends fearful of their reaction, and had spent an enjoyable time researching some more about female clothes and cross dressing. I obviously did not tell him that I had been ordering tights and stockings, but was surprised when he told me that the hair looked great, and people would get used to it after the initial shock of the change. So I got used to my new style and grew relaxed with it, but when I went out I would wear a baseball cap to hide the fringe as I felt that the most girly part, and my social life returned.
Julie had told me that roots would show after a few weeks, and sure enough I felt the parting was getting to dark so rang to book an appointment. It seemed I was getting into a routine just to maintain things. I was shaving all over and doing my nails at least once a week, the salon about every four weeks and moisturising every night with a slow tanning product that was making my pale skin look far better.
I suppose it had to happen eventually, I was working at the desk and Paul came up behind and placed his hand on my back to steady himself, I had on a nice black under wired satin bra, with a black satin camisole, he could not see this under my black shirt, but he surely felt the straps. He jumped back as if electrified, apologised for being so clumsy, stammered a lot then went out for what seemed along time. I sat trying to work, but gave up and went to find him. He was trying to be busy fiddling with a camera.
'So?' I asked 'do we need to talk?'
'I don't know do we?' he almost whispered.
I offered him a coffee I had made 'do you want me to leave?'
'Oh god no'
I paused to think 'sure?'
'Yes' he replied without hesitation, 'but it was a bra strap I felt wasn't it'
I blushed 'fraid so, will it be a problem?'
'Well no I guess not, but….' And we ended up talking about me and how I came to be wearing a bra, by the end he had come to accept that though odd he could not see a problem and actually asked if I had anything else I was planning on trying, which I took as a good sign that I was more or less free to be as adventurous as I liked.
I did nothing about my new felt freedom until the week after, I was quiet so spent some time playing with my new look. I wondered what make up might change about the face, so tinted the eye lashes, thinned the brows and coloured the lips only slightly, as I sat back to think Paul came in and saw the screen.
'What are you planning now?'
'Just playing' I replied.
'Well lets see then' and he sat down and clicked away with the mouse,
'nothing to dramatic please, think of me and the customers'. he promised me he would, then I had a look at what he had done, he had defined the brows, darkened the lashes and glossed the lips, so with his unsaid approval I bought lip gloss and mascara to experiment with, and the next time I had a salon appointment I would ask them to 'tidy up' my brows.
In fact I could not wait for my full four weeks before I needed the roots doing, so booked early and asked for some extras, fine Julie said and booked me in. A few days later I came out with my usual well finished hair, but also under the fringe, my brows had been thinned, and in my ears two studs had been fixed. Nobody would see except me I reassured myself, and then went to work the next day looking similiar to the doctored picture Paul had done before.
Paul said nothing really, just stated that I had done it, and asked if it was what I hoped for. This was a changing day really, previously odd customers had addressed me as miss as they reacted to the hair I suppose, but that day nearly all the customers referred to me as a miss, one came back the next day and asked Paul if that helpful lady was in, which puzzled Paul for a moment, but he said he recovered quickly.
After a week of this I concluded that if I was going to be called miss it made no difference what I wore and might as well enjoy myself. I started by wearing my t-shirts so they could be seen, white and black at first, then I tried a yellow and then pale blue. Paul said nothing. I then bought linen trousers that I wore with thong sandals, but I did clean off the nail polish from my toes. This all took a few weeks to experiment with, so when I made my next appointment with Julie I asked if I could have a change, and a few days later she obliged me with blonde streaks which had the effect of making the fringe even more dramatic.
Next I tried a silk top, definitely not a male style with its low neck and loose sleeves. As everyone now called me miss, I started to seriously and not just because it felt right, to talk more softly, would walk differently, oh lots of things but basically copying female actions when I could. My nails all went pink, which I loved to see on the keyboard. My lips also gained a pink tint to match the nails. For getting to the studio I found a lovely coat, whereas my old coat was best described as loose, the new beige one was a snug fit and very comfortable. I was looking for a fresh pair of shoes, thinking plain women's style with laces might be best when I saw some nice pump type and ordered them, within a week I had ordered a pair of heeled courts, which once I had found some longer trousers, I wore to work.
I was still enjoying myself with the lovely clothes, and the attention I was taking with my appearance, but the buzz from having a secret hidden under my male clothes was gone now, but it was replaced with a desire not to be laughed at as a man in drag. I now wanted to present totally as a woman for fear of embarrassment. My research went into comparing men and women, how they moved, gestured, spoke and many other little things.
About three months after I first wore make up to work Paul made a coffee and looked at me carefully. I had used a hand bag for the first time, but as I sat I reflected on what he saw, heeled shoes, fitted trousers, white satin blouse, long pink nails, a ladies watch, gold chain round my neck, the hair had not changed much over time, just a bit longer and lighter, my face now clear of beard was subtly made up with just enough to emphasize my eyes, cheeks and lips, and from my ears hung dangling gold chains that showed below the hair cut.
Eventually Paul spoke 'so how long before I see you in a dress?'
'Oh' was my only reaction, then 'had not really thought of it, but trousers seem more appropriate for work'
'well have you worn a dress when not at work?'
I had to say no because it was the truth. I had looked at many dress and skirt styles but could not decide what I would go for, so had always gone for trousers. I asked why he was asking, and I got a, just wondered reply, but it got me wondering about coming to work in a skirt one day.
I now had another interest to study, skirts, there is such variety. But first I wanted to explore shoes some more as they become a bigger part of the outfit when legs are on display. So along with baggy cream silk trousers, a brown angora top I stepped into the studio in a pair of brown sandals with a slim 3" heel. As I hung my coat up Paul said 'hi Jem, the kettle just boiled' he called me Jem, I had half expected it some time ago, but to hear it as I wore these sandals for the first time, especially with the luxurious angora and silk, was like a real boost, he might as well have said you look gorgeous.
'You can wear a skirt if you want' this was Paul again telling me he had no problem with how I was dressing, I always toned it down if I was socialising but even that was getting hard as my mannerisms were becoming ingrained.
'I'm not sure about that' I answered.
'Well how about finding somewhere you would have to wear one'
'I think you want me to wear a dress don't you?'
'OK I think you should try a dress at least once, you present as female all the time, why not?' and so I agreed to go out that Saturday to a wedding were I was needed to herd the guests, but I insisted I would need at least half a day to do the shopping, and a visit to the salon in the morning.
The Saturday was a lovely day and I knew the outfit would be great. First Julie styled my hair giving the volume only she could achieve, then her friend gave my face a complete make over, and the nails had their first manicure. Then back at the studio I changed into a new blue outfit, a camisole top with matching calf length skirt that had a chiffon over skirt and a long sleeved top over the camisole. I hoped I had not over done it, I did not want to upstage the wedding, but as I meet Paul he just stood back and told me I looked fabulous, and for some reason I lent over and gave him a kiss, then sprang back to apologise. The wedding job was easy, but the feel of the skirt on my legs was wonderful and I knew I would be looking for opportunities to wear it again.
As we finished up at the wedding Paul enquired what I would be doing that evening, would I be meeting up with our usual social group later, when I told him I had made no plans but did not fancy a drink with our mates he suggested he get his best suit and we go out on our own.
'Are you taking me out then? Like a date?' I asked
'well if you want to call it that, but I can't imagine you being in a hurry to change, and you are stunning, so why not make the most of it?' I did not hesitate in agreeing.
At seven he picked me up, I had touched up my make up, put on a fancy pair of sandals and changed my jewellery, Paul was indeed in his best suit and looking very smart. There was a table booked at a top restaurant; candles, small portions and attentive waiters made it a quality evening.
After I had drunk a couple of glasses of wine, the conversation turned to me and how I dressed, Paul was still curious about it, and was obviously having no problems with it. He asked what I would do next, I honestly had not thought ahead at any time other than to think of one aspect, and at the time it was skirts that were my current interest, as it were. He asked if I ever thought of surgery, I said no, but he carried on talking about breast implants, asking how they might feel and look. At the time I just smiled and tried to answer his questions. It was later in bed that my hand felt my chest through the nightie that I felt his seed of thought take hold. What would it be like to have tits, I had a pair of inserts, but they felt unnatural so had only worn them a few times, but real ones they should feel like me.
This idea germinated over the next few days, I used the inserts to see how I might look, and I played with the computer imagines giving me a cleavage of varying sizes. Then Paul caught me, and I had to admit that I was thinking if implants but for now it was just research, size, shape, do I want them all the time. If I did it I could no longer go out as one of the boys no matter how far I stretched the idea I would still look like a woman.
Two days later I catch Paul on the computer playing with my image, he has generated a nude shot of me with a set of tits and one of me in the blue chiffon outfit.
'Do you like them?'
'They are very good' I meant the images, but I think he meant the tits.
'Did you know there is a clinic in town that does them? Takes two weeks, and there's no long waiting list.' He had me off guard.
'Oh' was all I could think to say 'is that so'
'yes, and you could stop at mine after if you needed time to recover'
'you have thought this through haven't you. How much will it cost, and what size have you got on there?' I asked as I pointed at the screen. 'Well those are D and those are CC under the top, and money is not your problem, you have helped me out so much, this is a way for me to repay you'
'so you think a D, I had looked at B'
'I know, but what is the point of just having little ones that are too big to hide, but too small to show off, I think you are past hiding now' he left me to mull over what he had said. I don't know how long I had been letting my mind wander, but he brought me around sharpish.
'you have an appointment tomorrow 3.30, and I am paying' that appeared to be it, I was getting breasts.
Next day I turned up on time with some images of how I hoped to look, he asked about the images and how it was done and seemed very interested, possibly more than in my current issues about getting a body changing procedure. He did point out D cups might feel heavy, but I lied and told him I often wore inserts so was used to how a full bra feels. Then when he asked how soon I wanted to have it done, I said I was still thinking about it. Then he tells me that there is a cancellation and if I could come in the next day. Flustered I excused myself and rang Paul, thinking we were too busy and this would need planning, he completely threw me by saying 'go for it, I can cope' so I returned to the consultant without any good reason to say no. So I signed some papers and left.
Next day Paul dropped me off with my overnight bag, reassured me I was doing the right thing, and then left me to the nurses. That afternoon while still awake I had some very small inserts fitted between my ribs and my nipples. Over next week they were inflated with a solution so my chest expanded slowly. In many ways it felt wrong being in hospital when I did not feel ill, just little tight and sore around the chest. I was then allowed to go home but was to come in daily for a top up and application of some skin cream.
It worked out well; I could spend half a day at the studio, and then go for treatment after. Paul for his part paid all the bills, and never asked to many questions, but I did occasionally catch him taking a sly look at me. The clinic provided support bras as my chest grew, but I did buy a black satin D cup bra so I could try it on and see how much farther I had to go. By two weeks I had a noticeable chest, by five I had filled my bra, I felt their weight constantly as they moved around in a most satisfying way. The whole experience was deeply stimulating, besides the weight the cream that I thought was to help the skin stretch also fed the nipples, so they too grew, no longer the size of a pip, when they were cold or tickled I had brown nipples that were the size of big raisins.
The effect of having bra fillers permanently went far deeper than I expected, besides the physical boundaries they created, they also made me feel female, I was constantly aware of them, but not the way a thong between your cheeks reminds you there is something in your arse, no this was more of reminder that told you, be a woman with these you are so definitely feminine. I did nothing to my wardrobe or make up, I just felt more deeply female.
And when the treatment finished and I went for the final checks, the consultant compared my original images to the end result and found them strikingly accurate, he promised to send some work our way. It was as we were doing some shots of me for the clinic that Paul gets the original image of us standing together as if at a gala dinner. I don't have an emerald gown only the chiffon blue, so an hour later we have most of it set up for a new set of photos to compare to the first. Then he took some proper studio type shots of me trying to look glamorous, it was such fun posing for him, lounging, sitting, and standing even one or two less clinical shots of my chest, Paul discovered how real they were as we did this, he casually asked if he could touch them, and to his surprise as well as mine the nipple reacted to his touch, they visibly grew and I felt a tingle run through the skin. I was about to shrug it off and call an end to the shots, when Paul suggests a models trick of icing the nipple, and so I held ice cubes to my nipples then let Paul take more erotic pictures of my swollen chest, to be fair it was very nice having the attention, even if the ice just did not seem such a nice way to get it. As I was in my favourite outfit with my newly enlarged chest, so we decided we should go out again.
Again a nice meal with relaxed chat, sometimes about how I was feeling, sometimes about how Paul felt. But once about how we felt towards each other, I think when I said that I saw him as the boss in some ways, yet as equal mates at other times, I set something in his mind ticking. I suppose this was further compounded when we walked from the restaurant and I shivered in a cool breeze, which resulted in him putting his jacket around my shoulders and my giving him a kiss to say thank you. It just seemed natural I told him, and then linked his arm as we went to find his car.
The results of Paul's mind ticking was on his screen a few days later, he had been editing the shots we had taken and cleverly merged a shot of me sat on the floor looking up a him as he looks down at me, with a hand on my shoulder. I just added to the image a title 'the boss'. When he saw it he smiled and said 'in that case you can make the coffees, while I sit here and watch your body' I laughed and made a performance out of doing the task, mincing around then curtseying as I offered the drink.
We joked about the whole thing, I called him sir or boss, and he started calling me Jem dear, sweetheart or petal. We had pinned the boss picture up, and quite unexpectedly Paul pointed to it and said 'you look far better than the image we played with originally, you are really good looking.' I blushed and mumbled I thought so too.
I bought my first dress, a cotton sundress, the weather was warm and the loose fit was cooling to wear. And when Paul suggested a trip out on Sunday I knew it would be just right for a stroll in a local beauty spot. We had afternoon tea, and then went back to his house for supper. I don't know if I encouraged him by linking arms, or sitting close on the bench in the park, but as we sat with our wine after supper, my legs tucked under me leaning on his shoulder, he asked if I would like to move in with him, followed by when was I going to come out with the lads again.
That night I spent a lot of time thinking about his questions, how would my old friends take the new me. As for moving in, that seemed like a good idea, we got on well, I felt secure with him and we had fun in our own way. So on Monday I told him about my thoughts and made plans to start moving in the next weekend, I would have the second bedroom, but I wanted some extra storage space. And so I moved in and rented out my house.
I also meet our friends one evening, Paul went all bossy on me, telling me I was going to do this, there was no way out, I was sitting around hiding in the house looking lovely and not getting out. I knew he had a strong character, but rarely felt it myself, but this time I was being told in no uncertain terms what I was doing. I wore casual trousers and a jacket, not wishing to be over stated. Then with Paul's inspection and certain attitude we went for a drink at our regular pub. We were the centre of attention that night and certain I did not want to do it again. But everyone got over the shock, two said they could see it coming, one thought it quite weird, and no one told me I was a freak that they did not wish to see again. We left early and once alone my emotions overwhelmed me, I hugged Paul and thanked him for his support, and that was that, I was totally out and able to join in with everything we used to do. I was so pleased how things had turned out.
Besides affectionate touches there was nothing sexual about the relationship, I just felt comfortable next to Paul at times and he never tried for anything more. So when he talked about taking another set of shots, I asked what did he have in mind, he suggested something a little sexier than before, but he said it in his manner that just meant this is what we will do, I am in charge please don't argue. And so we set up a back drop and he clicked away as I did as I was asked, slowly losing clothes until I was in bra and pants, and then just pants, and ultimately naked but posing so my male parts did not show. I then told him it was my turn and took a set of shots with Paul undressed, he had a fit body and could pose well so the results were good despite my average technique.
It was over the next few days when we had time that we edited the shots, selecting favourites and enhancing others, I liked a naked one of me sat with knees up hiding my wedding tackle while looking down in a demure sort of way. But I also liked a more full on pose standing as I could then play around with my body image, I tried bigger tits first, but that looked wrong, then I increased my hips and narrowed my waist, creating more of the hour glass figure which gave me something to think about. That was until I saw what Paul had done. Once more I was sat at his feet, but this time he was naked and I was in a very full and flowing red nightie, one of his hands was behind my head, but it was where my hand was that was most provoking, it was not perfectly done, but the image had me with a hand reaching up his thigh. I let my eyes linger on the image a while longer, 'so is this what you would like?' I asked, he stumbled for words saying he was just seeing what he could do if limbs were moved, I tried again 'but would you like to see this pose for real?' I knew he could almost get me to do anything he wanted, but for once I really had the upper hand. I told him to go and set up a plain backdrop and a delay camera. Next I told him to strip naked and stand in full shot, while he was doing this I was removing my clothes down to some very nice lilac underwear, unfortunately no red nightie was available. I then walked in to see his face a mix of puzzled and anticipation. Then I curled up at his feet and slid a hand up his leg and onto his inner thigh, one thing his image had not had was an erection, mine was hidden but Paul's was being photographed. I could sense him getting too excited and called an end to the camera shots. But before I got up I asked if he had enjoyed that, 'what do you think?' he replied. As I stood up I let my hand stroke past his genitals, I could do whatever I wanted I thought, and then wondered what do I want to do. 'Would you remove my bra and suck my nipples please' he could not get it off quick enough and soon I was feeling tingles in me as his tongue sucked my now enlarged nipples. I still had his penis in my hand when I asked what do we do now, 'nothing' he said 'I have dreamt of something like this for over year, you are beautiful, and I have loved you ever since you had your hair done in a Jem style' he then hugged me tight, kissed my lips deeply and came in my hand. We said nothing as we dressed and cleaned up. I made a coffee and added some whisky. Then looked at each other as the revelations sank in. We scrolled through the shots till we got to the one he had tried to create earlier, his erection was obvious, as was his look of pleasure, what was also obvious was the look of enjoyment, lust and something like admiration as I looked up at him.
We then looked at one another 'this changes things doesn't it'
'it certainly does, should we stop and separate, is this right?'
'Right, wrong, I love you'
'let's close up early and go home, we shan't get much work done now'
'OK' I stepped over and kissed him on the lips
'right you lock up and get home as quick as possible, there is something I want to try out.
Before getting home I stopped to buy some KJ jelly, it was no surprise to find him home before me. 'Right there are two things I want to find out, one is would I be able to have bigger hips and a slimmer waist, the other is what is it like to fucked. I think you can help with the second' he nodded
'well let me find the red nightie, then I shall see you in your bedroom'.
From the expression on his face he could not believe what was happening, and from the feelings in my body I could not believe what I was doing, but there was inevitability about it and it felt right. I did not have a crushing orgasm, just a warmth of being close and feeling him inside me. The orgasm came a week later after I had learnt to relax and feel his touch inside. For that afternoon though, he had spent himself on me, then sat with a drink and rang the clinic to book me in for body contouring. I told him my clothes would not fit if I did this; he said it would be worth a whole new wardrobe to see me happy. How sweet, now that deserved another kiss at the very least.
This association only accepts men who prefer to be ladies, so certain standards are required so everyone realises it is serious and not part time. some of the rules are to stop easy swapping between gender, others for pleasure.
The work can be in any sort of environment, and you should dress according to that place.
The ultimate goal of all members is to live in the world unsuspected, to enjoy the role of a lady, to be desirable to men and be immersed in a life of femininity.
This association only accepts men who prefer to be ladies, so certain standards are required so everyone realises it is serious and not part time. some of the rules are to stop easy swapping between gender, others for pleasure.
The work can be in any sort of environment, and you should dress according to that place.
The ultimate goal of all members is to live in the world unsuspected, to enjoy the role of a lady, to be desirable to men and be immersed in a life of femininity.
YOU SHALL FOLLOW THIS CODE OF DRESS.
The penis will always be taped out of sight unless it is needed for other than urinating. If required stitches can be used to keep these parts concealed.
Breasts will be worn at all times, size C or D cup will be considered the minimum.
All bodily hair to be removed, legs can tested at any time, so shaving is not the best option, waxing is to be encouraged.
Nails must be filed neatly, and grown past the fingertips by at least 50%. 75% is expected as the norm, double length is thought to be excellent, but can be improved on in some cases.
Hair will be grown to shoulder length or beyond, it will be styled, no flat straight styles will be accepted, and always look immaculate. No unisex styles.
Eyebrows to be plucked and neat.
Ears will be pierced; obvious earrings will always be worn. No small sleepers.
Make up will always be worn, as appropriate to the occasion.
Nails will always be painted.
Dresses and skirts should be obvious, making you conscious of them, and affecting your demeanour in some way i.e. very short, or tight, or floor length, or possibly 50s style petticoats, a very full skirt maybe acceptable if it is long and gets in the way. Whatever the style it should require constant attention and vigilance to keep it correct.
Stockings, no tights, unless with short mini, but then bare tanned skin would be viewed preferable.
High heels at least 3", but 4" or higher preferred.
Slippers to be heeled mules.
Corsets must be worn if you slouch or fail to keep the stomach in, or for generally poor posture, but can be worn for preference, a narrow waist is always more curvy and pleasing. The waist should be at least ten inches narrower than the chest.
A tampon will be worn 3 days a month; you are being treated as a woman.
A hair salon shall be visited at least every 6 weeks.
Jewellery is to taste, but at least a neck chain and bracelet.
Always sit to pee.
You shall get ready for bed before supper.
Satin nighties shall be worn.
If invited out, you shall always dress to impress, and suitable for the venue. The choice will also emphasize smart sexiness, you are there representing the association.
When out with a client, dress to please, and make him happy. Repeat clients are best.
Under no circumstances are you to untape yourself for a man, you are the female partner, and he must play the male role, not you.
Some sort of aerobics or dance will be done everyday for about one hour, gym is fine as long as you do not create muscle growth on the upper body. Of course lycra outfits will be worn
If you feel able to life within these rules, then sign below.
The association was formed with the intention of allowing suitable men to live as women. The association takes the attitude that 'if a job is worth doing, it is worth doing well', with this in mind all members shall be required to present and live a full female lifestyle. This does not necessarily mean an ultra feminine look, but at the very least definitely feminine.
To achieve this there are rules which will be adhered too.
Meeting targets will mean rewards which help create a more feminine person.
Failure to meet the standards however is not an option, after three warnings and extra tuition that will go with the warnings, you will be excluded from the association. You will not receive any support from that moment, you will be allowed to take the clothes they are wearing and any money invested but no refunds spent on their treatments, any money given to the association will not be returned.
You will be out in a skirt and quite possibly looking a sight due to your poor style that will attract derision. But the choice is always the member's own to improve and stay or fail and leave.
Each treatment will attract rewards. Permanent treatments attract double or triple points
Getting the corset an inch smaller, one treat after dinner, chocolate is popular at first. :-)
Nails reaching approved length
Hair being permed and coloured
Waxing :-
Limbs
Bikini
Permanent hair removal :-
Face
Body
Breasts being attached :-
C cup
D cup
Breast implants :-
C cup
D cup
Hip implants
Lip plumping
Tanning
Piercings :-
Ears
Lobe 1
Lobe 2
ear top
Belly button
Nipple
Nose
Lip
Tongue
Anal plug, these work differently to the points, periodically the plug will be assessed, if it is felt to have done it's job and you have relaxed your hole enough, the reward will be the next size.
Size 1
Size 2
Size 3
Size 4
The rewards can be taken as points, gathering enough points for a free treatment, or a new outfit. Bonus points can be achieved by using a treatment to deliberately accentuate your femininity.
New recruits will be rewarded for accepting the rules with a maids outfit and lessons in make up and deportment.
Their first job will be keeping the house clean, and will when passed by the house manager, attracts points for beauty treatments, plus a size 1 plug.
The basic reward for new girls is a day off from maid duties if a feminine image has been maintained all week. this does not mean a relaxing of the feminine image, rather you will have time to express yourself more fully.
Maids who are good at domestic work and have at least 4 female defining treatments will be allowed to consider working elsewhere within the organisation.
8 treatments and restrictions shall be removed allowing you freedom to choose when you wish to go outside.
Learning to dance will be rewarded with new clothes appropriate to the dances learnt. Plus the oppurtunity to perform publically at the association's night club.
Learning to cook will be rewarded with a 1950s wardrobe. A further reward will be a personal maid to help with your duties and as a personal help, it is understood that this style does take extra effort to do well.
Being able to sew will give you control over what some of the other girls wear. Clearly this responsibility means you have an impact on the total look of the association, a good seamstresses will receive a percentage of rewards from their clients. Success as a sewing room will attract rewards for the whole group, usually an annual event similar to what the outside world might call 'the works do'
Once you are confident as a maid your reward will be to be moved to one of the association projects or businesses.
These include
A bar
Night club
Mrs Mop house cleaning business
Salon
Hotel
When it is considered you are able to work in public you will be found work in the outside world, usually a clerical position, unless the talents you have displayed within the association which have potential, for example cooking, then you may be found work in a kitchen.
A full time job, earning money for the association will exclude you from most domestic duties.
When a size 2 plug has been in place without problem the reward will be to have your name on the open list of members avaliable for servicing by members of the Alpha Club (see later)
Clearly dress is to taste, but every girl must adhere to the minimum requirements, extra points and priveleges will be gained if a girl chooses to dress in a more feminine style.
4" heels.
Hair in a style which is not easily brushed into shape.
Nails being twice normal length.
If these standards are maintained for a week extra points shall be added to the total.
Where appropriate girls will be encouraged to wear mini skirts, sheer fabrics, and show cleavage, if done well and in the right situation extra points will be given, unfortunately if dressed inappropriately points shall be deducted.
Though not a uniform as such association members will be expected to dress according to the role they choose or are selected to fulfil.
All members will start as maids, this will require a black dress, white apron, black heels. the underwear will be standard stockings, corset and knickers, but a layered underskirt to lift the short skirt will also be provided. This will the beginners position, but good members will soon have a feminine manner that is reflected in the clothes. The clothes are deliberately sexy and the work domestic to encourage the girl in new members.
The house cook will have 1950s wardrobe to choose from, her assistant shall be issued with lemon twin set and satin disc skirt.
Seamstresses can make whatever they choose, but all the sewing room must wear similar, this in the past has been interpreted along theme lines. Styles from medieval, gothic and regency have been used in the past. Whatever style is chosen it must declare the wearer to be totally female.
Girls working in the bar shall be provided with red satin tube dresses and satin thongs eliminating the panty line.
Girls working the night club will receive white silk wrap over dresses if they are hostessing. Those waitressing will be given long pink satin dresses in a chinese style with movement splits up both sides.
The girls chosen to work in the outside cleaning company will have tartan pleated skirts, white blouse and tabard with the company logo on, with a line in latin which translated says 'Here to give service'
The hotel will have several roles, chambermaids are like the basic maid but pink. Reception staff will be in pink suits, with short tight skirts and white silk blouse with ribbon ties at the collar.
Kitchen staff unfortunately get plain white cotton chef uniforms.
Waitresses are as the club, but not floor length, above knee length.
Salon staff will have pink cotton puff sleeve blouse with straight black above the knee skirts.
Managers of the operations shall wear suits in the colour of their staff, jackets to flare at the hips, very full pleated skirts and sheer blouses, obviously matching bra and or camisoles may be worn if the member chooses.
Directors though not directly governed by the rules shall be expected to set an example. Their outfits should not only reflect their sexuality but also their position of power and authority. Silk, satin and sheer fabrics are the basics for them. They will always dress in a way that will inspire other members. They will have received all the permanent treatments including at least a D cup breast implant, hip implants, piercings are to personal taste and must number at least three, but shoes are not, a directors minimum is 4" spike.
Girls in their free time or when being serviced by an Alpha club member are free to wear what they like within the rules
Any member of the association caught doing anything considered masculine will be cautioned first time, the second time the member will return to being a maid and have to prove themselves feminine once more.
Association members are not required to do manual work, there are men and rather dull women who like behaving butch who can do such tasks. Gardening is limited to tending for the plants, pruning watering etc, no member should use a spade or fork. Cars are not to have the bonnet opened by a member, punctured wheels can be replaced if there are no men to do it, if you look helpless some dumb man will think he is being chivalrous.
Most important though is that you must adhere to the rule about tucking, taping or gluing your penis back, this is for urinating only, sexual satisfaction will not be sought from this organ once a member has joined the association. Any member found pleasuring themselves in a manly way will be reduced to a maid and returned to the open service list where they shall have to achieve ten scores of very good or excellent before moving off the open list. Only three can be oral, at least seven must be for penetration.
The Alpha club is connected to the association but is secondary to the main purpose (creating beautiful interesting women). Members of the Alpha club must have good facial hair, a minimum height 5'9", good body shape but most important of all consider themselves dominant (we know they are not, but allow them their delusion) and prefer the company of men. Women are for satisfying certain needs and urges. A beer with a man is for fun or furthering business, a beer with a woman is only considered as a lead up sex.
Once new girls are placed on the service list they will be expected to entertain whoever chooses to service them. The Alpha member will score your performance. When the girl has achieved 5 satisfied or better scores the Alpha Club will pay for the next treatment. After ten satisfied scores you will receive another treatment and be taken off the open list and will be free to choose which of the Alphas you service.
If any member is struggling to achieve their target on the open list the house manager might suggest replacing the plug with a remote vibrator to which she alone has access and will use in the training of the members desire for sexual encounters.
The Alphas are not generally wanting emotional relationships, but a well adjusted girl will be allowed to be a 'wife'. She is to keep house and satisfy the Alphas other needs. The alpha shall pay all her expenses including an allowance and premier subscription to the Alpha Club.
To be considered good enough for the position of a wife, the girl must have gained good - excellent scores as a maid. Have achieved at least 5 excelent scores from Alpha members who have serviced her. She must also be able to live seperate from the assocation house. but most of all be able to look and live in a female role without being detected. If selected by an Alpha member she will be expected to submit to the request.
Loyalty for a wife is primarily to the association, secondary to her 'husband'. The husband as a premier member will still be entitled to the rewards, treats and access to the associations women all Alphas enjoy within their club, the wife should not expect her man to be loyal. The wife in taking the role will have removed herself from the Alpha club service list so she can concentrate on satisfying her 'husband'. She is only allowed to be serviced by another man with the consent of the husband, it permits him to believe he is in control. The husband can offer the wife's services to other men but not for money.
One lesson hard to teach but well worth learning is how to use femininity to get what they want. Members who can learn to be cunning and manipulative will gain the most from the Alphas who think they are dominant.
The role of directors.
These are the eight people who determine and control the fate of the association and the members.
They will manage all financial and legal matters for the members.
They have CEO powers in all the businesses.
The Alpha Club does not know it, but the directors run their club.
All new members must be approved by at least two directors.
Any one director can expel a member for failure to maintain standards.
Attracting new members is primarlly a directors role.
Privileges of Directors
You are given your own apartment.
Choose a personal maid.
Have proirity with their seamstress.
Use the salon whenever they wish.
Be removed from the Alpha list, directors are the only ones who can choose their partners.
Role of the houes manager.
To keep the house in order.
Maintian cleanliness standards.
Maintian the dress code.
Keep a watch on behavior amongst the members.
Draw attention to members shortcomings and offer help in overcoming them.
Administering the points.
Administering the rewards
Overseeing and administering the plug size for each member.
Liaising with the Alpha club over requests for servicing members on the open list, and to a lesser extent acting as agent to the members not on the open list.
Keeping the Alpha score records.
Role of the house cook
To cook all the meals for members who are in the house at meal times.
As the dress style implies, the cook is to be a traditional mother figure that will allow members free access to the kitchen for a simple chat or a deeper outpouring.
She is non judgemental
Should care for all the members in the house like family.
Be homely and ultra feminine at the same time.
Aim to be the homemaker in the style seen in TV commercials.
Role of a maid
This is to be every members first role.
The time is to spent appreciating a feminine way of life.
Learning make up.
Deportment
Grooming
As well as domestic duties.
The short frilly dress is to help the maid realise her sexiness, while at the same time making her comfortable in a revealing outfit.
The maid will be given oppurtunites to explore her feminine side fully.
Encouragement will be made to achieve points and use them on the rewards.
A maid shall always be cheerful and helpful to any of the other members they meet.
A maid will be expected to learn how to satisfy a man.
Role of members who are working in association businesses
Promote the business.
Earn income for the association.
Spot and maybe recruit new members.
Be available to Alpha club men, only serious objections about a man will be accepted as grounds for refusing to service the Alpha club needs.
Role of members working in non association jobs.
Be totally convincing.
Never bring the association into disrepute. The association is largely secret.
Earn money to support the new members.
Role of a wife (covered briefly elsewhere)
Be totally convincing to all except the 'husband' when he is inside the wife's knickers.
Keep house for the man.
Offer sex whenever appropriate.
Do not be disappointed when he satisfies his needs with another member.
be happy to service his friends if asked.
The primary role of all association members is to be a fully feminine person, living a totally female life, through the clothes, body shape, accessories, and attitude which for most should be deferential, although submissive is fine towards men, the essentail being a sexy woman who enjoys the ultra feminine life.
The association started by accident really. Two gay friends, one Gareth a big rugby player, who played at a pro level, and runs a successful property business and has a very confident almost arrogant attitude but is smart enough to know how to use charm to get what he wants. The other Max, is completely the opposite, slight build, did cross country as a schoolboy and knew how to compete but stopped when he left school. His hero is his mother, she has always been there for him, worked to fit around his childhood, was always a stylish woman he was proud to be seen with as he grew past those awkward puberty years. His work career had never really taken off, college qualifications in media studies does not help in the real world, his interests were in art and creating visually interesting effects. When he meet Gareth he was working at a supermarket check out.
Mid twenties the friends have a regular friendship, in as much as when Gareth is around he calls Max who will come running, he knows he is being used and suspects Gareth to have other partners, but he is always sure to use condoms. Max will try to watch his friend play whenever he can, but understands how in the macho world of rugby Gareth will not want it known he is gay and will take a girlfriend when necessary.
The start of the association begins when Max having left home and is living in a tiny flat near the gay village. He loses his job for refusing to have a hair cut and remove his ear stud. Gareth offers to support a claim for unfair dismissal, which eventually gets some compensation, but Max is soon in financial trouble he can only get poorly paid bar work and the flat is in arrears. Gareth has a daily cleaner he pays nearly as much as Max is earning, so Gareth's solution is for Max to move in with him and keep house for them. Max has a bit of OCD and is very clean and tidy in all he does, so cleaning a house is something he can enjoy.
That was the situation that created the opportunity for the association germ to grow from. There was a significant conversation where Gareth complimented Max on how nice the house is and the meal they were eating was really good, but Max was not his usual self and Gareth had not had sex with him for over a week, saying he had things to do every evening. Max accused Gareth of just wanting cleaner who he can shag when it suits him. Gareth was also tired and snapped back telling Max that Nell the previous maid was prettier than Max and did not expect sex all the time. The defining word in the argument was the use of the word maid to describe Nell.
The next day more as a joke, or an attempt to diffuse the situation, Max visited a costume shop and hired a maids outfit, short black dress,frilly underskirt, a padded bra and wig. He also had to buy some make up, shoes, underwear and stockings. He was working of the image of the maid from porn films he had seen. Once home he created that sexy maid image using his art skills learnt at college. When Gareth came home Max was waiting at the door to take his coat, then fed him a meal not eating with him, just waiting on him. Once the meal was finished Max cleaned up then took Gareth a whisky. Max could never explain why he did the next act. He asked Gareth if there was anything else he could get him, Gareth was relaxed and enjoying the attention, but rather than wait to be asked Max knelt in front of Gareth undid his fly and sucked him off. That night Max got the shagging he was hoping for.
The next evening, so the story goes, Gareth came home to a more normal reception, Max was Max again, and though the meal was good and the house all clean etc. Gareth was disappointed that the maid was not on duty and went out to meet some rugby friends straight after the meal.
Max's mood was hurt by this turn of events and spent the evening and the next day reflecting on how the two evenings had been so different. The next evening was pretty much the same as before. So he tried the maid routine again, and was rewarded with Gareth's company and plenty of intimacy later. That experience more or less sealed his fate. Max kept the hired costume until he had sourced a good fitting dress and all the accessories. He also visited his mother and tried casually to ask for advice on how to do normal make up as opposed to the theatrical or punk make up he had done at college. Apparently she did help but gave him a 'funny' look and asked if everything was fine with Gareth.
It took Max about a week to get himself fully prepared for a first dressing in his fitted dress, in a classic maid style with frills, stockings and heels he treated Gareth to a night of luxury and was rewarded for it. Max from then on dressed and acted as Gareth's maid every evening they were home together. This did not make Gareth any more loyal but it did make Max more submissive.
Things in the house and relationship changed over time. First Gareth gave Max the name Maxine when he brought home a wrapped gift with the new name on it. The gift was a sexy red nightie, which he made clear his partner was expected to wear to bed that evening. A more defining event happened one weekend when Gareth moved all of Max's possessions into the second bedroom, explaining that now Maxine was the maid then she should have room of her own. Initially shocked at being exiled from Gareth's bedroom he found out he was not totally exiled from the bed and spent the night with him, but the next evening when Gareth told him he would be late home told Maxine to sleep in the second bedroom, so he did not disturb her when he came in. The constant use of Maxine, her and she, did not go unnoticed by Max either, but he learnt quickly that Gareth liked his maid and was generous with it.
Soon Max had three miad dresses and plenty of underwear. And if Gareth suggested something, maybe higher shoes, Max would be sure to have them for the next time Gareth saw his maid. Gifts of feminine jewellery were common as well,especially after a business trip. Very soon Max relaxed in his role of maid, and though he had first worn the heels about the house in the daytime to get his feet used to them, he was wearing them out of choice enjoying the way they affected his walk and posture. his mother a woman of style soon started to influence his dressing, the initial make up lesson extended into grooming which he was good at anyway, but not familiar with female scented products he took her advice. Every time they meet she would ask how things were and once she found out about the maid outfits encouraged him into more feminine ideas. He already had one pierced ear so naturally had the other done. She plucked some eye brow hairs to neaten them up, but the next meeting she removed a few more explaining what she was doing. With her encouragement he removed all his body hair immediately swearing never to be hairy again once he slid his stockings up that evening. The other thing his mother did was to invite herself for lunch when Gareth was away, the first time Max was Max, but she made a note on the calendar that she would be visiting again and wanted to see the maid. Max tried hard to forget this woman was the centre of his life and treat her how he thought a maid should treat this woman. He was repaid with plenty of advice from a woman who knew a lot about presenting a feminine character.
Gareth noticed many of the changes and rewarded his maid with more gifts and money to buy new clothes. After a few months the novelty was wearing off, Gareth was not appreciating his maid the way he had at first and Max was finding it hard to cope with the rejection when he slept alone for several nights on the run. They still had a social life but mostly apart, but one weekend possibly three months after the first maid adventure they went out to a gay bar as boyfriends. There was a drag artist on and several transvestites had shown up as well, one or two friends with Max already. This was the evening that Max's sexy role play idea moved up another level. Max had been chatting with a transvestite friend while Gareth had been bonding with some other macho men, but it was later that Gareth told Max that he fancied taking Maxine out the next weekend. Max tried to object but it was useless and he knew it. Gareth was very supportive and praised Max for how good he looked when dressed as the maid, comparing him to women not the transvestites he had been with, he also gave him money to buy an outfit.
The following weekend Gareth showed off his partner to his gay friends, then the next week took Maxine out for a meal at a smart restaurant. For the gay friends Gareth wanted him looking hot, so bought a gold mini and a leopard print top. For the meal Gareth wanted something sophisticated, Max dutifully bought long pleated skirt and a long sleeved blouse with slash neck. Gareth's opinion was that the mini made him look ready for sex, while the other was restrained but with the high heels and other accessories had an air of repressed sexuality, which he duly released when they got home.
Max might have been frightened to go out as Maxine at first but soon it became accepted that if they were going out together, he would be a 'female' partner, and was treated as such.
Next was being found out by his mother, she was having lunch with him, this time as Max, and after a visit to the bathroom challenged him about the range of women's clothing drying there. soon she had the full story and insisted they go shopping the next day, with him in the pleated skirt. It did not take long after that for Max to be living in skirts fulltime, his eye brows had become too fine for a man, and it became easier not to remove nail varnish and glued on breasts if he just needed to pick up some groceries. Besides which, he enjoyed way the clothes made him feel, and he felt closer to his mother than before, which he also liked.
He would always be dressed as the maid unless Gareth invited him to go out as Maxine, or if going out shopping, but then sometimes it just took a coat to hide the clearly unusual dress. He was also only having sex when Gareth wanted it, and rarely shared a bed, but Max was happy in this role, he had an easy life most of the time and when he wanted there was always retail therapy, new outfits being purchased mainly for Maxine's pleasure but was always appreciated by Gareth who only saw them occasionally as Maxine was nearly always in a maid dress when he saw him.
This new relationship of maid who went out as a girlfriend when he wanted, distanced them especially for Gareth who came to see his friend as an employee come escort when the need arose, there being little genuine affection between them since Max had been the maid, as maids do not greet their master with a kiss or embrace as Max might have done when he first moved in. So it should not have been a surprise to anyone that Gareth started to bring home friends to find out how good it is to have a maid wait on them with food and drinks. The next progession would be for Gareth to see Maxine as a sex object and offer her to his guests. Max had had several partners in the past and knew what to do, but what stung initially was being considered a chattel who could be told to satisfy one of Gareth's friends in the bedroom, even once when Gareth was showing of his dominance over the maid, made Maxine offer her arse in full view of the friends, and then be screwed by two of them. But Max had slipped so completely into his role of submissive female maid that he never complained coming to accept and like the attention he got through these situations.
Max had in less than a year become a totally feminine character, and willingly allowed dominant men to use her. And she was happy, maybe not so much about the being used by any man Gareth sent her way, but it was sex and mostly enjoyable, hieghtened by the sexy clothes which was part of everyday life in the house.
Max's acceptance of this position caused him to embrace the female role completely. He saved and persuaded Gareth to add the difference so he could pay for cosmetic surgery. After research and discussions with other transvestites and transexuals a clinic was found that would perform the alterations both Max and Gareth wanted. Maxine convalesed as a daughter with her mother before returning to Gareth's house where they were free to explore the new body Maxine now possessed. A salon had helped in the transformation so the hair was in a nice blonde bob, the facial hair was being removed, size D cup implants bounced within the bra, liposuction had reduced the waist, the hips enhanced with gel inserts, nails had already been trimmed and polished. Maxine now looked the part (as long as the male part was tucked away in the knickers) and behaved the part of a woman, and most of the time while outside the house a restrianed sex appeal was what that part looked like.
Maxine unknowingly was the first member of the soon to be established Association. While living with Gareth as his maid and sex toy, Maxine's friendship with other transvestites increased and while there were transexual friends they could not understand why Maxine had kept the male vestige, but there were transvestites who could. A few wanted to live 24/7 like Maxine but could not because of many problems they would face if they turned up at work as a woman, the families would be a problem and places where they lived might be trouble. By chance Maxine found out one of Gareth's properties was not proving easy to let, so Maxine made him a proposion. Maxine would take on the house, live in it and do it up. The timing was excellent, Gareth was becoming bored with the fun of having a maid at home fulltime. So to move Maxine out and invite whoever he wanted home, without any trace of guilt was very appealing, plus he had an empty house. He considered the idea, agreeing to it on condition that once it was ready Maxine would move out, plus Maxine was still to be available if he needed a maid, an escort or just a good fuck. Maxine agreed.
It took a week for her first friend to move in. The object was to let the friend live 24/7 as a woman and also help with the house. Cleaning was great, and Gareth had men who would do any hard jobs. The first friend was not as succesful as hoped for and did not have the desire to be totally committed to a feminine lifestyle, being found one morning dressed in boxers and needing a shave, Maxine asked him to leave. John was the second and perfect, 5'4" young with light hair growth, effeminate and gay. The day he moved in he only brought his female possessions, introduced himself as Leah (after the princess) then spent half a day making himself into a herself, before presenting herself to Maxine, who was very impressed with what she saw.
A month was spent turning Leah into a convincing woman from a raw transvestite, the excesses were polished off and grace introduced, until Maxine had no worries about letting Leah going out in daylight to do shopping. The house was improved and Gareth showed his apppreciation by taking both Leah and Maxine out in a foursome. Leah was warned about Gareth's nature, but unphased by the casualness of sex was happy to entertain Gareth's friend.
The friendship between Maxine and Leah grew, they worked well together and also enjoyed going out to the gay bars they knew. But as their female personas developed they increasingly spent time in the more generally straight areas, but for sex it was always gay men they wanted, which over time became harder to achieve because unless the men knew them, they would be taken for real women and rejected by the unknowing gay men.
Among the cross dressing community the house attracted new people for whom the idea of living 24/7 appealled. There were four bedrooms and finding new housemates would ease the cost of running the house. However Maxine did not wish it to be a tranny house, it had to appear as a woman only house share, so any new housemate had to convincing, garrish TVs were banned as were part time dressers.
It was after two more failures and one success, that Maxine, Leah and the new girl Pheobe sat down to discuss how to stop the failures and the rules were started. The initial purpose was to make it clear what was expected, that new girls had to be committed to being a 24/7 convincing woman. They also started to make it clear the financial side needed sorting out, all transvestites have trouble getting work or keeping their old jobs, so with the nominal rent they paid, it was felt they could get some free loaders, the answer was to insist everyone hands over their income, usually benefit cheques, and also put some money up front which could only be used for beauty treatments.
The rules were a success at stopping the half hearted starting and only the good ones joined what they were starting to call the association. Within ten months they had all four rooms occupied with the two larger ones being shared, making a total of six girls. The house was clearly getting crowded and Gareth wanted it back now it was in good condition. Maxine was still on very good terms with him and took on another property, a large house with fourteen bedsit rooms and scope for more, but it was a dirty mess and free. So Maxine moved her group in and they slowly transformed it. The rules were adhered to except for decorating jobs when it was permitted to were overalls and flats for safety.
They did not need new girls but they came anyway, soon one girl showed herself to be a good cook so looked after the kitchen, two found work in bars, one worked in a supermarket, all handed over their wages so that the house could be repaired and the general upkeep funded. As this fund grew it was also used to pay for treatments that helped new girls gain a more feminine image. And so the rewards system came into being.
The idea of new girls having to be maids was Maxine's, she had enjoyed her time in a maid's dress and thought it right that a new girl should serve those who were supporting her, it also meant the new girl did not need to go out but was busy and learning about being dressed as a girl 24/7.
In two years the house was renovated and fully occupied, a girl called Heidi was cooking for everyone with the help of a new girl Ann. Maxine was busy keeping things together. Pheobe had worked as an assitant accountant before so easily managed the money and rewards. A few had jobs, but the next breakthrough was being asked by Gareth to clean and decorate another house. This spawned two ventures that carried on after the first house, one was a Mrs Mop daily help, the other a derocating business. Gareth used both after being persuaded by Maxine who knew just how to manipulate a man with an erection. The income went into association funds. Next they converted the garage into a salon, they were spending so much as a group it seemed sensible for one of them to learn the skills and set up a salon for the association. It was a success as Gail was a creative stylist who could achieve some truly wonderful cuts as well as offering a full range of salon treatments. When Jill joined her they started doing outsiders and real women that they knew and could charge a proper price.
The money was coming in and Pheobe came across an oppurtunity to take over a bar in the gay area of town. A team of four were asked to run it, as expected sexily dressed men behind a bar sells drinks very well and when the hotel next door came up they took it. This created extra accomodation for the assocaition, extra income and for new girls a place to be maids.
The Alpha club in escence started about the time Maxine and Leah took on Pheobe. They knew any girl could be sexual but did not want the girls playing the male part. They insisted Pheobe permanently tape her male reminder out of use, then arranged a few dates for her with men arrogant enough to believe Pheobe wanted them, but gentle enough not to upset her. It took until the third date before Pheobe came home with a smile on her face and thanked them for setting up the men for her. Leah knew men would pay for sex, but did not want to turn the association into a brothel. What she did was to offer escorts, some descrete advertising and vetting achieved two things, income as the men paid for membership, plus the new girls learnt how to have sex, for most this promisciuos behavior was quite normal having been gay boys before, but for a few like Pheobe it was seen as necessary for them to feel the submissive female position in a relationship and desiring men over women or other members of the association.
The Alpha Club generated the idea of a night club, but due to limited number of association members it was felt that the decorating business was not quite completely within the rules and would close in favour of work that would allow the full feminine lifestyle to expressed.
Another house was taken on, and the association grew into a kind of cooperative for the benefit of members who agreed to the rules and accepted the rewards, both from the reward scheme and the rewards of the chosen lifestyle.
Reading BIG CLOSET Can Have Implications
I am sure if you are reading this, then you have enjoyed some of the Big Closet stories. Well my tale started when my wife and I were surfing and came across the site, just following links and curious to see what is out there, but we returned to it on a few occasions and read some quite interesting pieces.
To be honest we got lucky, we read the brief intros and found ones that did not offend us very often. There are some sad people and some others who really should be looking for help if there lives or fantasises are really as told.
But I digress, we enjoyed the notion of sharing or swapping roles, we already shared the household jobs, but mostly along male/ female stereotypes, I clean the car J (my wife) cleaned the kitchen, a pretty average arrangement. Both did what we could for the kids.
So we started with job swapping, J was good in the garden and I liked the change of doing the indoor work. Nothing to raise an eyebrow in this, but we tried some new bedroom activity as well where J would take the lead and get me to please her more than I knew how to before.
It was several weeks, possibly 2 months after we started the role swaps that the thing moved onto swapping clothes. This was quite easy we are very similar in height and build except for the obvious chest and hip variations, shoe size is even close. It started with knickers at weekend, I would wear her satin briefs and she borrowed my stretchy boxers that she liked. We both found this stimulating, and after an initial worry about wearing them all day. Our mothers always said when we were kids that you should wear clean underwear because you never know if you were going to have an accident and end up in hospital, where the nurses would see them. But this was somehow on a different plane, end up in casualty in the wrong pants and the nurses would not be thinking anything about whether they are clean or dirty.
As the weekends passed so did our confidence, first a camisole, then tights when it was cold one day. The underwear soon became so mixed we did not bother separating it into his and hers, it was just ours. And we would go to work in the 'wrong' clothes if something nice was on the top.
Next we tried some outer clothes, a pair of jeans possibly maybe a jumper from the others cupboard, J did have some really soft jumpers the main drawback was they tended to be soft colours as well, but there was a beige to start with. J liked mine because they kept her warm in the garden. Soon I was in a lemon yellow cashmere top and tight hipster jeans, J in a boiler suit as she fiddled with something on the car.
The kids I mentioned earlier were not to much of a problem, they are J's brother's kids but they both work shifts so about once a month they stopped at ours for the night when they were treated special. When they were around we were careful to keep the clothes discreet, but not the job swaps. It was not until later that the kids became a problem.
Some weekends we tried to be as androgynous as possible when we went out, maybe more feminine or more masculine depending on what we had and how the mixed. Other times we went for each other's clothes exclusively. J one evening when we were going out for meal got my suit out tried it on deciding it fitted fine tied a tie around her collar and picked up my brogues. I was still in my camisole, knickers and tights when she suggested her linen trousers and white angora jumper. I just thought why not and tried her flat lace up shoes on, a bit tight, so off with the tights and on with a pair of flat sandals. Fine but what an odd couple we made, me looking like a camp gay man, J appearing as a butch dyke. We chose our bars carefully and had a great time watching how people reacted to us, the gay bar we tried felt really comfortable, even if some of the looks were a little predatory. The smart straight ones were nice to see reactions as they tried to work us out and whisper to one another then look at us. It was fun and we were sure we would be out again doing the same thing.
We also tried evening classes; we both chose one then enrolled the other without telling them. J seemed to like playing with the car so she ended up on a car maintenance course. J enrolled me on flower arranging saying how nice the house looked but flowers dropped in a vase was not the best way to display them. I even agreed at the end of the course10 weeks later.
The next time we were out on our own it was decided to go a little further, J went for my striped shirt and black trousers. I had always liked her loose black trousers they seemed to be so soft and flowed with the air; with a white vest top and suede jacket I was ready. But J had an extra idea, she thought lip gloss and mascara would add a bit more to the look, moving it away from androgynous but still camp/gay. We had another fun night, and started planning our next before we got home suggesting what the other should wear even how they behave, I wanted J to always buy the drinks, J wanted me to link her arm like girls do.
We started going to a couple of bars quite regularly, maybe twice a week if time allowed, the rule being we dressed in each others clothes. Through the week we were more and more using the 'wrong' underwear, even wearing tops and trousers that were 'wrong' as well. Slowly I experimented with make-ups, tinted lipstick, eve liner and blusher mostly. Sometimes I was sure I looked quite girly especially when I started with the nail polish. Saturday was becoming more get the housework done then I can get myself ready, it was getting more involved this dressing in J's clothes as time went on.
So we did our classes and enrolled for some more, woodwork for J, cake decoration for me, well Christmas was not far off. I gave J some jeans and an old shirt to wear, she kindly bought me a piny, fortunately nothing fancy just a striped chef style, I did think it was going to be frilly and pink, what a relief.
With autumn coming, I starting wearing tights under my trousers to keep warm, or so I said. While J was borrowing my thicker jumpers and trousers for work.
One evening when getting ready to go out I picked out a lovely top but it had a lot of darts in the front so it sat all wrong on my chest, about to put it back J suggested I fill the chest with her padded bra, was this going to far? I was not sure, J was wearing a pair of my jeans that were unfilled at the front, and if she filled the jeans I would fill the top. Soon I was wearing a snug fitting top that curved around my chest as well as it ever did on J, and J had a bulge in her pants. It was then I realised that I was not going for an androgynous look, I was definitely looking feminine, what I thought was a camp gay look had been lost as soon as I had a chest.
A moment of worry hit us when the kids called round unexpectedly a week later, J kept them downstairs while I quickly showered and pulled on suitable uncle clothes, still with knickers of course, and a faint whiff of scent . The kids ended up stopping a week and it felt so restrictive, not wanting to get caught, how could we explain it to 8 and 10 year olds. I don't think we were rumbled but I was asked why my eyes looked dark, and J was asked if she ever wore a dress.
Soon the kids went back and we back to our unusual ways after the kids left, but it took a few weeks before we had completely relaxed their guard, with the fluffy lilac jumper coming out for the weekend housework session.
Christmas was coming I had done several cakes for the family, and J had made a simple bookcase whilst on our courses. We would spend Christmas visiting family, but New Year we could excuse ourselves with real or imaginary invites to parties. So we reckoned that after Boxing Day we could do as much role swapping, as we liked. But we still had to shop and there was all December to enjoy as well.
We decided to buy each other clothes, what else, but without it being said we were not only buying for each other we were buying for ourselves. For J we bought a tailored trouser suit in cream, with a burgundy satin blouse, she looked quite stunning. For me fitted trousers with wide stripes and a blue casual shirt, for Christmas day we felt they would look great while visiting.
Once home with all our gifts we sat back and discussed the day reflecting on how we had got on. J was thrilled by the looks I got, nothing unusual for me I guess, but not many blokes go out dressed in low cut jeans, a pink v neck and suede jacket and produce a purse when paying for items. J was not much better she had heavier clothes and boots on and had my wallet to carry the money in. J wanted to try on my trousers that evening, but I insisted they were mine at least until boxing day, then we could swap, which I was looking forward too, the satin blouse felt lovely but the trousers did look tight. J insisted that as I wanted to go all manly on her, she might go girly, but that after we would swing back further than before. To which I asked in what way. She felt the days of a camp/gay going out with a dyke would be over, how about go for boy and girl completely.
We carried on pretty much the same until the holiday, got ourselves cleaned up for the family, my mother in particular commented on the trousers as being unusual for me, little does she know I thought. Then come 27 December we had a second present giving all of our own. J had to do what I felt was manly and she would return the favour. In her package was a voucher for a hair cut, a false moustache, some heavy rimmed glasses and this was my favourite, a vibrator which had an extension which pointed forward and the more it vibrated the longer and harder the extension got, and I had the remote on/off for it. Not to be outdone J had adhesive tits, a lady shave and long brunette wig, which she assured me, could be fixed to my hair. We already had what we were going to wear, exactly what each other had worn on Christmas day, all we had to do was prepare. Before lunch I had a B cup chest and a bald body. J had been for her short boy cut and sported the facial hair. J then carefully pulled small sections of my hair and threaded them into the wig till it felt very secure. It was peculiar in a nice way to feel the hair between my shoulders, added to the time I had to take brushing it, I was really enjoying myself. J left me all afternoon to play with make up and her hair styling tools, as well as several books on what to do. She would pop in every now and then to see if I wanted a drink to find me still sat in bra and knickers with her dressing gown wrapped round me. Eventually I was ready, all those times spent using just gloss or mascara had helped, but getting the eyebrows neat, and eye shadow colour etc all took time. Next the suit, the blouse fitted and felt excellent, but the trousers were a problem, they were tight and showed a front bulge, fine if I looked gay but not if I wanted feminine. J came the rescue with surgical tape, securing my male bits between my legs. Then she remarked that only one of us could enjoy an erection, which was true enough, I could pee, but anything else was out, the thought of tearing the tape off was enough to make any idea of sex disappear. The trousers fitted fine now just a bit long, so I would have to wear heels, I guess it was the running I do but once I got them on I felt ok in them, but they were only 1 ½" block heels. Ready, J changed into my clothes, she looked quite good really, making sure she had the dildo device in I asked her to look at me as I tried to look sexy and turn on the device, she smiled and her trousers tightened at the front, 'pleased to see me, I see' I tried to say in a sultry voice. She just smiled and gave me a kiss, telling me I did indeed look gorgeous, but it was time to go.
Considering I have been wandering about in J' clothes for ages now, the thought of some one saying there's a bloke unnerved me as we got to the front door. J realised and paused, I checked my bag for the purse, make up tissues, zipped it up, then J took my hand pulled my wedding ring off and replaced it with her 2 rings. Then whispered in my ear that if this went well she a few other ideas I might want to try out tomorrow.
The evening was great fun, if J looked at another woman I would turn on the device, now you know how men feel when we see beauty, I commented. We ended up walking around a few bars then driving home. On the drive she started letting her hand come off the gear knob and onto my knee, then slid it up my thigh, just like I used to, so I flicked the switch and left it on until she stopped, just to let her know how I felt when I did it to her. Once inside we helped each other undress, as the night before, but J pulled out a new package, which said 'for tonight' it was a red silk nightie, I slipped it on, and switched her on again. She just smiled as I went to lead her into bed, not sure what would happen, but having read enough on storysite, knew a tube of KY jelly would help get her lubricate her extension inside me
.
We woke sore and exhausted, J had come more than once as the device vibrated away inside, until I eventually had a nice sensation which the stories had told me about, but my dick was sore as well as my arse. I looked at J, moustache still firm, with a t-shirt on and I could not help but smile. Over coffee and toast I asked what else she had in mind that she did that I should experience. 'Still keen?' so I tried to get her to tell me first, but she just said I could always say no when we got there. It took me ages to get ready, brushing the long hair, that remained firm, then shaving and doing my face, eventually I got to the clothes and realised I could wear any top I fancied, I choose a frilly cavalier style with leather trousers. J just pulled on a sweater and jeans, then said lets go. Life seems unfair at times, especially after I had taken an hour getting ready and she just waltzes in and is done in 5 minutes. We drove about 30 minutes and pulled up at a nail salon, the penny dropped, extensions, I was not in work for 10 days so why not. J left me to it as I was pampered, glued and painted with French tips about 15 cm longer than my nail, but maybe longer, they felt and looked enormous. On a whim I noticed they did piercing, and came out greet to J with a pair dangly ear rings in, which had to stay in all the time, until the holes healed. I realised I had made a mistake later when I was sleeping. J sensed I was easy and went for the all or nothing approach. She lead the way to some shops, I was as nervous as I had been in the salon, about being a bloke dressed as a woman, but now mixing with the sale shoppers I felt quite exposed. J appeared to be quite happy pushing around like a man, and first went for new boxers, and a t-shirt with a sexist slogan on it. Next it was my turn, I had to buy some silky bra and pant sets, and sheer tights, next J told me how much she liked me in a nightie so would I buy some more, I did, a pink and a black full length satiny ones. Then it was home for a rest. J had other ideas she wanted to go out again, even rubbing her groin on my hip so I could feel the extension. I agreed without much of a fight, and then she said she would like me to try a dress or skirt, this had been on my mind all day so easily agreed. J has not got much choice but she does have a nice maroon calf length skirt with lots of flaring, I wanted to wear boots but they were a size too small and had to wear sandals, this time dressy ones as they were being seen, a blouse with such full sleeves I thought I would catch them. It took 2 hours but I was ready. J took 15 minutes. The evening went pretty much as before, walk around some bars, come home undress, get excited, go too sleep.
I woke early, hair in my face, and nightie wrapped around my legs, and enjoying the sexy soktness. It was ages before J woke, by which time I had sorted the hair into a style, shaved and done my face, even picked out J's high heels and had a walk around in them. I entered the bedroom in just heels and underwear, J smiled at me and felt on the bedside for the remote and turned it on, I just saw the boxers rise as she pulled the bed clothes aside. Morning sex whatever next. My dick strained against the tape, and my arse strained against the extension, but J was enjoying herself, and soon I was there also, and tired again.
This went on for three days, I just wore sexier and sexier outfits, until I was in a halter neck mini, on stiletto sandals, with possibly more make up than I should, enough scent, and so much jewellery I chimed when I walked.
Come new year we had decided on going into the city for the night, J insisted I wore stockings with her sheer dress that went over a short slip, she really wanted no slip, but no way was I wandering about with my knickers showing, well thong actually. It was a great night mixing with loads of people, kissing and hugging complete strangers. And then making love in the back of the car, I swear she had it switched on all night.
Soon the holiday would be over, and I was actually looking forward to the rest, my face was getting really sore, two shaves a day was hard if I wanted smooth. My dick was really sore at times and talc or cream was not the answer. So I carefully unpicked the wig, and stored it away, then released the tits, my chest skin was sore from being pulled down all the time, I would also be able to sleep on my front again. The nails came off easier than I thought and the freedom to use my fingers again was so nice. Now able to face the world as a bloke again, I checked myself, holes in the ears, eyebrows too neat, I just hope nobody comments, but J has her hair cut short and a red top lip where the moustache had been. We thought we had done alright, my mother looked at me oddly but said nothing, J's friend Emma wanted to know where she had been when she called one day, and suggested she look better with longer hair. I went out running again and was really uncomfortable, without body hair I was sweating more, especially in the armpits. J persuaded me to wear the nightie still but it was so much hassle getting unwrapped in the night, without the constant stimulation of the fabric, I gave it up after a couple of times. The worst moment came about mid January, the kids were stopping and the little girl asked J why I had no hair on my legs when her dad did. J struggled to think quickly and just said I like it, this got back to her parents who a few weeks later asked if it was true. I could feel the cold sweat on my back as I said it was for a fancy dress at New Year, and then looking at J's hair asking if we had enjoyed it. I had to say it was fine for New Year but for the rest of the year I was just shaving my chin.
Swapping jobs, even roles had been interesting, even fun, but serious clothes's swapping was hard and sometimes uncomfortable, and I would be leaving it for special occasions from then on. I could easily get used to being ready in 5 minutes and waiting for J. Likewise J had missed the excuse for a pampering, even wearing a skirt because it looked good and she had the choice.
In time my body hair grew back, I stopped sweating so much, my private parts recovered and was able to enjoy straight love making once more, J's hair grew and she does look better with it longer. But we still enjoy our stereotypical roles, J is good at maintenance, and I am getting house proud, and the knickers are still nice and soft to wear, I am just careful I do not have an accident, I don't want a nurse to find out if I have clean underwear on, especially if it is on the odd occasion I could not find mine and wear J's.
Sometimes we find it hard to motivate ourselves, this is true of any human activity, and it needs something or someone to inject a little interest back into us to spark the passion once more.
I knew this was not my usual style of dress as soon as I put it on, the fabric was so smooth and slippy, it felt great just to touch but to wear it was another challenge. I first recognised this was going to be different to my usual just above the knee cotton skirts when I sat down and the sarong type skirt opened up exposing my knees, refusing to maintain any modesty unless I kept a hand on the wayward fabric.
'You can't expect me to go out in this' I pleaded with Martin.
He looked at me with an impish smile 'But it was you who suggested I choose your outfit'
I had been friends with Martin for years, well Julie at first but then as our friendship grew we would meet up in drab as well as drag depending on where we were going. Of late though I had been losing interest in wearing a dress choosing the easier option of trousers whenever we got together. A fortnight before that day we had discussed my dull clothing, Julie was in a straight black skirt and red satin blouse, while I was in chinos and a darker grey shirt. We had dressed like this for possibly six months now if we meet on Canal St, me as a man, Martin as a hot Julie. It suited me but apparently not Julie. She was recalling fun nights we had had flirting with the trannie watchers and mixing with others who make up the Canal St circus. I was not saying I did not enjoy myself, rather I had just lost the motivation to get into a frock. Julie wanted to change this, she was fed up with her always being the girl in our outings, so I was persuaded to let Martin be the trousers the next time we went out and he would dress me as his ideal female partner. I felt this could be fun, not least because I had been suggesting to Julie what she might wear on occasion, even lending some of my unused clothing for her to model at my suggestion, the blouse she was wearing that evening was in fact mine, so it was only fair I returned the favour, as it were.
And so that is how I came to be sitting in Martin's front room wearing this wrap style dress, it had felt and looked lovely on the hanger, but now it was on me I was having second thoughts about this burgundy delight. My doubts were not helped by Martin's insistence that I wore underwear that matched the dress, a D cup satin bra ( bigger than my own, but a norm for Julie), knickers with laces at the side and worst of all stockings and suspenders which might easily show when the dress gapped at the front. Off course I had the obligatory heels, well made up face with lips reflecting the dress colour, he lent me a nice long dark haired wig and made me wear long glue on nail extension, something I rarely did as they make me feel so awkward, off course they were painted burgundy as well.
I sat there working out how to stop the dress from exposing my stocking tops, Martin watching as he stood in the doorway with my second glass of wine in his hand, red naturally.
'I have booked a taxi, should be here in ten minutes, do you want a wrap or something?'
'A wrap please' I could drape it across my knees if need be I thought.
He returned with a black silk pashmina and a few extras. Jewellery, I hardly ever wore it so had not realised it was missing. A long necklace that nestled between my breasts, a chandelier in each ear, a small watch with a chunky bangle on the other wrist, but then he picked out a diamond looking ring, tried it on my fingers for a fit and when it slide perfectly onto my third finger left hand, he just smiled 'Welcome Mrs Martin Butterworth, I am sure I have a plain ring to go with that' all I could manage was a strangled, what. Not only was I dressed how he wanted me to look, but it now looked as if I was married to him.
There was a car horn outside 'Come along dear, that will be our taxi'
'Right behind you darling, your missus is following her man' a quick look in the hall mirror to check everything was fine then out the door. I had done this many times before, stepping outside in a dress, but this time I felt more vulnerable than I remembered as I regained my heel walking gait.
Five minutes and we were being dropped near Churchill's, a short walk to a nice chinese and time to relax. my legs were under the table so the exposing thighs did not bother me. We chatted rather like any other time, work, family, politics whatever. The meal over we called in at a bar to see if any friends were about, being unsuccessful there we tried another and found two trannies we had seen before and three camp gay boys who were always good for a giggle. They all wanted to know why the role reversal, and all pronounced me the best looking girl out that night. When one of the gay boys noticed the wedding ring he said something about it, I made a joke about how it had been a quickie Las Vegas marriage, but what happened next was most surprising. Martin took my hand and told everyone how I was now Mrs Butterworth and taking to being his wife well. I was about to say 'What?' but as my mouth opened he kissed me full on the lips.
It was only quick but the impact was immense. 'We need to talk' I said 'Over there' pointing to an empty corner. The kiss had not been the first, as Julie and Lauran we had often hugged and kissed but in a girlie sort of way, that kiss had been sexual. I was still reeling when we made it to the corner, Martin leading the way keeping hold of my hand. The kiss had been totally unexpected but that was not to say unpleasant, so as the shock wore off I wanted to know where it came from and if Martin was planning anything else. A quick discussion about the kiss which went something like, 'you could have warned me,' 'your face was a picture' I bet it was' did you like it?' 'not sure' 'let's try it again then' and before I knew it his tongue was playing with mine, only this time it was not a quick raid more like conquest. He was a good kisser and I never knew, but then why should I?
Having had our words in the corner we returned to our friends who were giggling and making comments like 'thought you were just good friends'. The evening continued, Martin treating me like his partner instead of a mate. Holding hands, arm around my waist, while I responded by linking his arm as we walked between bars. This was turning into a memorable evening, that got even more memorable when we decided to dance at Napoleons. At first I did not notice but the dance floor has mirrors all round so it was not long before I realised that the lights were doing something to my clothing, I forget why this happens but the fabric of the dress did not block the light and everyone could see my underwear in glorious vivid detail. I was off the floor in a nano second, and finding a chair, (they have high bar stools there,) I sat down only to have my dress part across my thighs. Martin was right behind me 'Sorry did not expect that', then stood in front of me between my knees and kissed me once more. 'You do look hot though'
'I feel hot as well' I replied 'the blush is still burning I think'
He leaned in for another kiss while at the same time placing a hand on my bare exposed upper legs. 'I mean hot as in you are making lots of blokes here hot. Why not flaunt it, you have the body to do it' and with that he gave me another french kiss while his fingers played with my suspender clips. No man had ever kissed me this way, it had always been a disappointing grope and fumble followed by a request for a blow job, which if I am honest rather put me off men and wanting to attract one.
He managed to get me back onto the dance floor when slower tunes were played, I even commented that I was his anyway, I wore a wedding ring, and the fabric on the dress at my wrists and neck stood out like the underwear did making it look as though I had a collar and wide handcuffs on. He joked that wives sometimes vowed to obey so maybe he should get some real handcuffs etc. I had to laugh, as this was something neither of us had any inclination for and as for Martin being domineering, well I just laughed.
The night ended with a taxi back to Martin's where we found half a bottle of wine needing to be finished, so curled up beside him on the settee listening to some chill music.Our wine gone.
'Did you enjoy yourself tonight?' Martin asked
'Yes I did, thank you.' and I snuggled further into his arm that was wrapped over my shoulder.
'I think we have found another side to the quiet Lauran'
'I think we have' I noticed the dress had parted once more and this time I made no attempt to cover the exposed stocking top and nearly visible panties.
'Did you like being my wife then?'
'After the initial shock'
'Meaning?'
'Well the rings, the comments, the kiss etc'
'If you think that shocking, how about this?....... Mrs Butterworth, as you know I have only one bed, you have drunk too much to drive home, so how about we go to bed together'
I was keeping up with idea of stopping so asked 'together?'
'Well you would not expect husband and wife to sleep separately on their first night'
'Well no'
'And as you know I do have some lovely sleepwear'
'Middle drawer I think'
'That is right'
I gave him a kiss and took his hand off my thigh.
I did get to wear a nightie to sleep in that night, but not before I had asked Martin to unfasten the dress, then as it hit the floor we kissed and ended up on the bed. The stockings provided easy access to my hole once the knickers were pulled to one side. My man got to satisfy his carnal desires. I got to feeling sore, but happy I had been there for him. I woke in the morning wearing a pink satin baby doll outfit more than satisfied with my performance as Mrs Butterworth.
Still in the nightwear, over breakfast I was asked if I would be going out as Lauran more often. I asked when Mr Butterworth would like to take his bride out next. We just smiled and he said 'Soon'
I never knew what fun there could be if only I tried a new style.
Well how to start? A bit of background, my name is Dan and I live with Marcus and not that we shout about it but we are more than good friends who share a house, we do have separate rooms but at times enjoy the comfort and affection of sleeping in the same bed. Marcus is a big bloke, he used to play rugby but was never one of the huge ones just a well built bloke who could run and handle the ball. Me I keep fit running and riding a bike, meaning I like to stay thin and carry as little weight as possible.
Well things changed between us when Marcus came home from work, he hardly ever makes comment about what he calls a boring accounts office because nothing ever happens, well something happened this day, the top management wanted to have a theme party and everyone was being pressured to bring their plus one. I said no problem I would go, he thanked me but recounted a story of bloke who came out of the closet to the office and eventually left because of the low level homophobia, nothing that could be taken to a tribunal but enough that he felt uncomfortable especially from a small number of staff members. So the answer was no, I would not be going with him. On the plus side to this party was that everyone had been given a decade to choose their style from and Marcus had picked 1950s out of the hat. We both loved rock and roll, Marcus even had a teddy boy suit, drainpipe trousers, long jacket and shoelace tie, going out to jive events more to watch than take part, two blokes dancing could cause a bit of a stir whereas two women went unnoticed. So unfair we would mutter and console ourselves with another coke.
A few days later I asked Marcus how his plans to get out of the dance were going, he was not to happy about how things were going, a woman who was doing a lot of the planning was asking questions about if he had got a plus one yet and one of the homophobic managers was trying to get him to admit that he was gay and would be fetching a bloke. I was a supportive as possible but he was not that positive telling me a broken leg might just be his only option with a hospital bed being his out.
That Saturday I arrived at my sisters after discussing the problem with her earlier in the week, I was unsure this was a good idea but felt it was the only thing I could do to help. With quite a few nerves and a lot of trepidation I knocked on the door.
‘Come in Daniele, how nice to see you.’ My sister gave me big hug as we kissed cheeks.
‘Please let’s just see how this works and will I make it.’
Soon I was in the shower washing my body hair down the plug hole before washing my hair with some very feminine smelling shampoo and conditioner. In a pink towel dressing gown I was seated in front of her vanity and told to look the opposite way, mirror behind me. She coated my face with her cosmetics before she took the towel turban off my hair and got to work with her hair drier and then heated tongues. I was allowed to see myself once my head was done and I was amazed at the pencil straight hair style she had got out of my shaggy locks, but on top of that my face had big eyes and very inviting lips if you like women looking pouty, and all thanks to makeup. While I was taking in the image I was seeing, she was sorting out my clothes. We are similar sizes and so I was soon wearing her scarlet bra and panties, zipping up a sheer red blouse before pulling a pair of her tight jeans on, thinking a skirt might be too much for me to handle on a first dressing, last dressing experience for this time she showed me how to buckle up the low heeled sandals to my feet.
I was taken to see what I thought of the redressed me in a long mirror.
‘Just wow, that is amazing, we look like sisters, Daniele and Christine.’
‘Well Daniele, if I say it myself, I did a good job. Now you have to decide can you walk out that door?’
‘Oh er, do you think I look that good?’
‘I think you look like a girly girl, what matters is do you? If you do then get yourself home and surprise Marcus.’
It took a while before I had talked myself into driving home.
I was home before Marcus came in from his day in town shopping. I was busy cooking when he came in.
‘Hi Dan, I’m home……………….oh sorry Christine I was expecting Dan to be home.’
I tried to make my voice softer and higher ‘He is home, just making your tea.’
There was a pause in which I did not dare turn round I wanted to see how long it took for him to work it out ‘Dan, what have you done?’
‘Come up with a solution to your plus one problem, say hello to Daniele.’ Making an exaggerated curtsey in front of him.
To be fair this was quite a bit for him to take in as he had no idea what was coming. ‘Did you buy anything nice darling.’ Hanging onto the darling to make it hopefully sound sexy. ‘Well sit down and I shall put the food out for us, do you want a glass of wine?’
As we ate I was very aware of him watching me carefully as I hammed up the feminine gestures. I explained how I thought I could pass as his girlfriend. How Christine had done the transformation. How it felt to be wearing unfamiliar clothing. How I felt about being seen as a girl. I told him I was fine with everything and actually liked the new sensations, and I was already his girl in all but name and dress, he smiled at this but it was true I liked doing the house stuff, cooking and cleaning were my domain and we knew it. At about eight he had been quiet for a while and looked at me with a serious face. ‘So let’s test this new look. Not been in the flying swan for quite while, white wine and soda for you no beer for my girl.’ He smiled and that was it I slipped on a denim jacket and picked up a shoulder bag Christine had given me to put my keys and money in.
We got back home a few hours later, a few drinks and plenty of close encounters with customers who took no notice of me as Marcus’ new friend. Marcus even commented how nice it was to be able to hold hands without fearing someone staring at him like happens when holding another man’s hand. In bed later I asked if he thought it was a good enough idea to work. I loved it when he nibbled my ear and whispered ‘yes’.
This was the start of a hard training period for me. Christine taught me how to do makeup and lent me a few outfits she did not wear anymore. The following weekend I wore my first skirt, a plain grey cotton A line. Christine made me up well before I had to make my own way home once more and be taken out by Marcus once more. Soon I was coming home and to start with walking about the house in my new heels which increased in height until I bought a pair of truly high heels thankfully with a platform sole under the ball of my foot so the 5” was really far less. I also started to look forward to getting home and changing into a skirt and tights, which soon turned into full make up and styling my hair if I had the time. Off course my weekends became purely Daniele time. Besides enjoying learning and experiencing a feminine style and life, it allowed me and Marcus to be affectionate outdoors, our reserved attitude towards one another broke down as I was slipping easily into the role of his girlfriend. Being able to hold hands, kiss and cuddle in public meant that when we got home single beds was not an option and after an early tenting in a skirt disaster, I took to using surgical tape to hold any future embarrassing erections in check meaning that I was always going to be the bottom if I was Daniele which seemed appropriate really and even more in keeping once I started wearing satin nighties to bed. At first to help me feel more feminine but later to help in the arousal of our love making.
In the few short weeks between Marcus being so despondent about this party he has changed completely to someone actually looking forward to it, he had got his teddy boy stuff out and after cleaning it found the trousers were now too tight, the jacket was fine and with a pair of black trousers and black shirt he looked quite good. But we both knew that a suit did not change much over the decades whereas women’s style was more defining, we needed to find a proper 1950 disc skirt. We looked online but once I was confident to go to shops in a skirt we went looking for the real thing and not just pictures.
Fancy dress shops had some half decent dresses but when we came across a vintage dress shop down a side street. We found ourselves looking along the rails while explaining what we were after to a more than helpful proprietor, soon I was being ushered into a changing area, this was not the plan, we were only looking. A glance over my shoulder towards Marcus hopefully saying ‘Help!’ did not help as this woman smelt a sale. She almost helped me undress as I tried to keep my back to her, I could not believe this over helpful attitude was normal, no one had ever come into a changing room when I was trying on gent’s things, maybe this is what women do in smaller shops. Whatever, I was working hard to not let her see my slight bump in the panties and socks for boobs. She had three dresses for me to try on. The first pink with bows on it was just too fancy and thankfully tight though she said a corset would sort that out. Second was a blue satin dress that felt fantastic to touch and was a possible, Marcus nodded approval when I was ushered out to show him. Last was a yellow one, net skirts, a bit more frilly and satin type underskirts, my favourite and when I showed Marcus he agreed, but being a man (I teased him about that later) felt obliged to pay. The woman found me a small clutch bag and some sling backs in a matching yellow. We thought we were sorted but as we paid she pushed a pair of seamed stockings into our bag, telling us they would finish the outfit off. I said a little too loudly that I did not have a suspender belt which she heard and told me that I should always treat myself to new underwear when getting a special outfit, I nearly blushed to my bones. But even more devastating were her last words.
‘You are so convincing I would never have guessed if you had not made so much fuss about keeping your back to me, you must really love being a girl and your man is just great, you will make a great couple on the dance floor. One thing though, there is a shop which you might have heard of, Bois and Gurls, go and get yourself some life like bra fillers.’
I did not know whether to be insulted, praised, embarrassed or encouraged.
Marcus was rather enjoying shopping with me and the thought of going into lingerie shops for the first time meant his curiosity would have me in something suitable for the dance. He teased me with black and red saying they were dead sexy and white was for virgins only, that was said with a wink, thankfully I found a set in lemon and we could leave for home. But not before Marcus followed through on the woman’s other suggestion of going to Bois and Gurls and fixed me up with a very realistic feeling pair of tits and a bag of lozenges that when sucked are supposed to raise the pitch of my voice. I sucked one on the way home and was soon speaking in what sounded to me like a squeaky voice making Marcus laugh and for me to giggle in a peculiar way which made us laugh even more.
With just a week to go I spent all my free time improving some aspect of my feminine appearance, makeup, posture, deportment, hair styling, even just being a girl about Marcus, who responded by coming home one evening and telling me he is going to treat me to a salon appointment so I can get my hair and nails done for the big event.
My sister, Christine, was never too far from developments and would come round to see how I was getting on, making constructive comments when needed, though suggesting I go all submissive now I was a sissy girlfriend did not go down well. I still saw my relationship with Marcus as the same even if in bed he was always screwing me.
The salon was a big step. I dressed as feminine as possible in a blouse and short denim skirt with my hair up in a pony tail. After a little chat about what sort of do we were going to she persuaded me to let her trim my hair, give it a colour to deepen the richness of my hair and fix it up ready for the evening. She wanted to extend my nails but I turned that down in favour of just having a manicure and polish, just how could I get long nails off for Monday but pink polish should come off with remover.
Christine was at our house when I got home and loved the sight of me walking in the door wearing a short skirt and high heels, with my hair up and nails flashing the pink. She hugged me, I asked was I being sensible, she told me I looked fantastic and would be a fool not to go through with it. And when she helped me into the dress told me I definitely had to go. She was good enough to drive us to the hotel where the dance was, giving us a lovely hug as we parted. It was now just Marcus and his ‘girlfriend’ hoping not to get found out.
We had a great time dancing, some of the others had good outfits but I reckoned ours was best even if Marcus did not really look like a teddy boy. I drank champagne most of the time and got rather giggly which only made me worse as the lozenge had its effect on my voice. I am sure no one noticed that I was really a man as plenty of people came to me and made comments like ‘We had Marcus down as gay, he never talks about a girlfriend’ ‘He’s a dark horse, where has he been hiding you?’ I tried to be ambiguous in my answers but my best reply was ‘He is man enough for me.’ In reply to someone who suggested Marcus was a bit camp.
It was late when we got home but my boyfriend wanted to impress on me that he was man enough as he insisted on making me scream as he pumped his semen into my hole. Sunday was such an anticlimax, by Monday I would have to strip away all this lovely femininity and go back to being a regular Dan again. After using the cleansers and removers I was looking more male but my hair now had a fringe which was a big change and I was sure would not go unnoticed. But it was as we talked in the evening and I expressed how much I had enjoyed playing the part and would be happy to be his girlfriend for the next party, Marcus smiled at me and asked me why wait that long, we could go out the next weekend with another couple from his work who liked rock and roll and fancied learning how to jive. I thanked him with a big kiss, it was then he added that he would not mind if I retained something of my feminine clothing fulltime. I was thinking of wearing panties all the time but with his consent I virtually threw out my briefs on the spot. I made love to him again in one of my lovely satin nighties grateful that I could pick the best bits of both genders, I would not miss makeup and heels everyday but I did enjoy dressing up and feeling the luxury of female fabrics was great.
If you remember Les Dawson and this character then you might understand this.
Oh Ada, have you seen the new girl at number 32?
Not sure what you mean.
Number 32 where those two blokes live, Marcus and Dan, you know who I mean.
Oh yes, nice people the skinny one could do with a few pies in his diet though.
Oh I know what you mean, no meat on him is there.
Well go on what have you seen?
Well (looks both ways to see if anyone is listening) you know how I said I thought they were (whispers) homo-sex-ual.
Gay you mean. You said you saw them being far too friendly in a hug the other day.
Well I think I was wrong.
How’s that?
Well I have seen a woman coming and going with the big one, Marcus I think he is called.
You mean a girlfriend?
Oh most definitely one of them, and not just holding hands, they were in The Crown last week and I had to look away, kissing in public.
No!
Yes, never let my Harold do anything like that.
I should think not, that is for indoors.
And you should see some of those skirts she wears, see her knickers virtually.
Best not let your Harold see that, be wanting to see yours next.
Not unless he is feeling brave.
So he’s not gay then.
Who said he was gay, seems happy enough to me.
And have you seen the thin one?
Sometimes, only see him going to work and coming back.
And the girl?
She must spend all day inside, only goes out of an evening and weekends, that house must be spotless what with two men in there making a mess.
Well I never, another sherry Ada?
Yes please, make it a large one this time.
Some say truth is stranger than fiction. I that case, this could be true.
The benefits of a public school education are not to be undervalued, nor posh rich parents.
First I should explain something odd about British schools, there are public schools and state schools. The public are only open to the public with money so not truly public, and these are ranked in proper public schools such as Eton, down to the lower minor public schools which have aspirations of grandeur but not quite the gravitas, but they still turn out well educated young people whose parents think a comprehensive education paid for by the state is not suitable for their offspring.
Lesson over. I am seventeen and doing my A levels hoping for good grades so I can get into Oxford or Cambridge. I have always been good at the more art based subjects, I am good at languages, drama and visual art, english as you can possibly tell unfortunately is not my strongest talent, but then you should see my science results.
In my first year as a sixth former, I put myself forward to be in the school play as I have done since I was thirteen, I usually got small or non speaking parts, this year was different. I need to explain a few other things to help you understand why what happened did occur.
The school is a mix of boarders and day boys, I was a day boy as were about a quarter of the pupils, this meant I got to see a lot more of my parents than most of the boys, though saying 'morning father' hardly means seeing my father in truth as it was our only regular conversation before he went to work and stayed out till late most days. The other unusual thing about our school was that we had no girls. Now I know you can see where this is going, no girls for the school play. Well in previous years the plays had been male only productions or some girls from a nearby school had stepped in, but only as minor parts. Once I remembered a leading female part being played by one of the older boys along with one other who had a minor part. So there was a precedent for what happened to me.
In all the previous years we never got asked which part we wanted to play, we offered and were assigned a part, end of discussion. This year however I was asked if I would like to take a role, and before answering was told to go home and read the part, maybe discuss it with my parents. I soon found out why this novel approach was being taken, I was being asked to play the leading lady in a comedy. I had not seen the play before and skimmed through it that evening, then over dinner asked my mother what she thought of the play and more crucially the part I had been asked to play. Father as usual was at his club or meeting clients that evening, so the two of us chatted about the play, the idea of me playing a lead, and of that role being a female lead. By the end of our meal, she had said she would ask my father's opinion, but as for her attitude, she felt it would be an interesting challenge and something I should seriously consider before rejecting the notion as daft.
I think my mother used to be something of a hippie liberal in her student days, but somewhere in the past that got lost with the money and security of my father's family business, or maybe I was the reason for the marriage I did not ask to many questions just in case I did not like the answers.
In the morning I asked father if he had spoken to mother, he gave me a vague answer, so I asked if he had any objections to me being in the play this year, he said not and that it was an excellent idea. Though right then I did wonder if he had all the facts about the play. But I had his consent so I went to see the head of drama to tell him that I would take on the part of Kim. He seemed unexpectedly thrilled, hugged me and told me I will make a divine Kim. I do like Mr Watts but he is a bit of a lovey.
We had two months of rehearsals, starting with the basic reading, followed with stage planning and polishing the performance. But before we got very far I was being asked if I could speak just a little bit higher, then when we got onto the stage, I heard more than once 'Russell, please more grace, Kim is a lady not a docker'. I did not have much idea what was meant as I had never played a lady or a docker for that matter. So after one rehearsal Mr Watts suggested I watch women at every opportunity and try to copy their moves, he also sent a letter home asking mother if she would mind helping me learn some basic lady like mannerisms and movements. The other thing that I suspected might be a problem was a scene later in the play where I and the leading man have to kiss. Now I had known Paul for many years, he was a boarder and a very good student, not a close friend, more we knew each other because we did the play every year. This year we had to spend a lot more time together. Mother initially after we had a couple of read through invited him to our house so we could rehearse together, 'get to know each others lines better' was the idea.
Well we got on better than I expected Paul has a natural wit and could make me laugh at the slightest thing, which made our stage relationship much easier to cope with, me being his opposite as it were.
The letter sent to mother by Mr Watts had a quite dramatic effect on my spare time as mother took it upon herself to educate me all about how to look like a lady. She might have been a liberal hippie and still at heart trying to save the planet, but she was not a scruffy hippy, she had a great sense of style and enjoyed looking good, not showing off, just understated beauty I suppose. Well it started with deportment lessons, walking with my back straight and my chin up, she even had me walk with a book on my head. So I got the idea of being upright and poised. We moved onto how I should sit, walk the stairs, where and how I used my hands. I thought I was picking it all up quite well, but not well enough. Mother came into school and had a meeting with Mr Watts, she wanted to know how I was performing, he said I was getting better but there was still room for improvement. Then she went onto find out what costume I would be wearing. This meeting had a severe consequence back home. First I was being picked up on my movements all the time, so much so that it felt like I had to walk, sit etc like a woman all the time I was at home, she even included eating into the skills I had to master. Possibly far worse came a week later, I was to be dressed like a professional woman in one scene, which according to mother meant heels. Fortunately she bought the shoes without me going with her to make sure they were the correct size, but from that evening on I would come home and instead of taking my black school shoes off and replacing them with slippers, I took my socks off as well and spent the evening in my heels. I understood the logic as soon as I tried to walk, if I had not practiced before a full dress rehearsal I would have been so distracted by my clumsiness, I would have been awful and possibly ruined the rehearsal. It took me about a week to be confident with my heels and not get a ticking off for an unladylike walk. Then I realised how little I knew about women's clothing, those had been a low tiger heel barely an inch, mother introduced me to what she called proper elegant heels, thin and high was my description. This was a harder challenge, but I soon had it mastered and could walk about the house with ease, and without criticism.
With about three weeks to go, I thought I had cracked it. I knew the script pretty well, I could do the moves and the flow of the play seemed to be coming. Then we did a full run through, including the kiss scene. That was terrible, Paul usually cool about everything tensed up and clearly did not want to do the scene, I likewise was having trouble with the concept of kissing another boy. Besides that the cast were praised for their efforts and when mother came to collect me that evening as it was late, Mr Watts asked for a quick word. The upshot was that Paul came home after school the following night. Mother took this opportunity to find out why we were so awkward with doing a kiss. Paul was more vocal, he insisted he felt uncomfortable kissing a boy, he had kissed girls, in fact if the stories were true he was something of a ladies man. Mother’s solution was that on the night I will look like a woman, so that should be alright. To get me over my fear of kissing men, I had to think of myself not as Russell but as Kim, make myself believe I am the character and so be the woman, at least while in the role. I knew this to be a classic way of acting, but to think of myself as a woman. That I was not sure about.
The next evening I was in for one of my biggest ever shocks. Mother been out and bought me a complete outfit, long sundress, underwear, the lot or so I thought. That evening I ate my dinner looking like a daughter. I was wearing the sundress, bra and knickers, my high heels, besides all that I had a blonde wig on my head and several items of make up I hardly understood on my face. She told me I was really pretty, and was shocked when I took a look in the full length mirror. She then leant me some of her jewelry, big bangles, long bead necklace, clip on ear rings (which really hurt) and a couple of dress rings. It was dressed like this I realised how different the world was, I had to think about the hem flowing around my calves, tuck it under me when I sat, and watch out for the beads dangling into things if I leant forward, keeping the long hair off my face. Then as the evening chill came she gave me a big scarf she called a wrap to pull across my shoulders, which proved to be just another thing I had to be aware of and check was neat at all times. She did however mix us both a martini and serve it in a cocktail glass. Very elegant.
The martini plus the wine we had shared over dinner meant that my resistance to her next part of my education was virtually non existent. After helping me to clean off my makeup and moisturise, she introduced me to satin nightgowns, long and luxurious are the best words I can use to best describe that first time I wore pink satin to bed. As we sat drinking our nightcap she asked me how I felt. I told her how I had been surprised that I looked so pretty, and that the clothes added to my weeks of deportment training did in fact make me feel at that moment quite feminine. She said that we should have another daughter evening soon, and to my own surprise was amazed to hear me saying in a very girly way 'that would be lovely mummy' as I went over to give her a good night kiss and say thank you. The kiss I had done when I was younger, all the other stuff was totally new.
I woke in the morning wearing the nightgown and feeling my head pounding. But mother was there to make sure I was fine, some paracetomel and a light breakfast before school, my regular words with father before he left to make the morning seem normal. Then time to rerun the evening’s events and how I had felt. To say my mind was not on my studies would be underselling the truth. I daydreamed all day until I finally got home.
For the first time in weeks I did not change into the heels, but went through to the kitchen to get a drink where I found mother. 'Are you OK?' she enquired, I told her I was fine, but she said I looked preoccupied and she was concerned about how I had felt about the previous evening. She made me sit down and talk through my worries, mainly that I had enjoyed being a girl too much, that the clothes felt so nice, that I might actually be too good at pretending to be a woman in the play, being a completely plausible Kim. She talked me through my worries, which mostly boiled down to, she enjoyed being a woman so from what she knew there was nothing wrong in that, she enjoyed the clothes, the attention to looking her best. And if I was a convincing Kim then she would consider all my training worth while. She then told me father was not coming home till very late that evening so if I wanted we could have another mother, daughter night. I hesitated but when she said she would help me with my make up my defenses crumbled and we went up to her dressing room and dressed me before dinner.
That evening followed the pattern of the night before, this time however I was less conscious of my clothes and was making the small adjustments to my appearance without thinking about them, such as touching my hair and smoothing the dress as I sat down. When mother mentioned this I was strangely proud of myself for acting so naturally. That was a Friday night and I could enjoy the alcohol without worrying about the morning, and for the first time in my life I drank enough to make me tipsy and giggly. So girly mother later told me. I also managed to get her to admit that she had been keen on this project because she only had me and fancied having, if only for a short time, a daughter. Hence the support, the training, the clothes and from my point the slow introduction and gradual reinforcing of feminine things, like the low shoes getting higher and the deportment getting tougher as the days passed.
I spent the weekend being Russell, at times thinking about this new side to my personality that I had found, and wondering what it meant. On the Wednesday we had a full dress rehearsal, so on the Monday mother invited Paul over for dinner. She had me changed as soon as I got home, Paul was to come later, so I kind of guessed what she was planning. Paul arrived on time, then after mother welcomed him in, he was introduced to the fully dressed Kim. He fortunately said the right things, such as, 'you look great' 'if I did not know'. I tried very hard to stay in character, and was mostly successful. But the challenge came after we had cleared the dinner plates, mother asked us to run through the kiss scene. I was concentrating very hard on my lines and the woman I was pretending to be, finding it surprisingly easy to touch and hold Paul's hand, I could sense Paul was having a small challenge of his own, but we managed to do the scene to mother's satisfaction, though she did suggest that our kiss looked more like fish bumping into one another. When she went out of the room I made it clear I had little experience of kissing, so he took my hand and picked up my drink and lead me outside where the air was still warm. Then he asked me to relax and shut my eyes, then with his hands on my waist he lightly touched his lips with mine, then another touch, then another, the touches getting stronger and longer each time until his lips remained on mine moving them about until I responded. We parted for air after a minute or so but he could tell I loved the sensation when I put a hand on his shoulder and pulled him towards me and kissed him. It was just a youngster’s first kiss and a clumsy learning one at that, but none the less it was a proper kiss. Our education was interrupted by a cough, and mother telling us we seemed to have mastered that part quite well, and it was time to run Paul back to his dorm. I went in the car with them not thinking of the consequences if my dressing was made public. We even followed gender stereotypes, Paul sat in the front as he was the man, I sat in the back like a good girl. What was more surprising was that when I got in the front for the drive home mother said I made it look as though I had gone to the back without thinking, I was pleased that was how it had looked, however I had realised the situation and knew that as Kim I should sit in the back. We then got onto the outdoor kissing, I tried to explain that I was hopeless and he was only teaching me. An excellent tutor he made if the scene she had witnessed was anything to go by, me hanging off his neck, Paul pulling my waist into him and lips locked in meaningful contact. I do not know why but as she described this I was looking at my feet and fiddling with the edge of my wrap. 'And that' she said 'is just perfect'
On the Tuesday we had a rehearsal that was all about making sure everything was ready for the full dress rehearsal. The lighting was checked, the props where inspected and for me my costumes were tried on. Mother had come along to help with this, there was me and two boarders who were to be playing female roles, so mother and Ms Jones took us off for a try out, our sizes had been taken, but they wanted to make sure everything fitted and we could change with ease between scenes. I had a smart business suit for a main scene, a short black dress for the 'kiss' scene and what mother called culottes, enormous long trousers really, with a big blouse. James and Philip also had what the women called cocktail dresses for my 'kiss' scene, but they were playing supposedly different characters through the play, so had various dresses and wigs to change into, James had to dress as an old woman, presumably Kim's mother, which was short grey hair and a shapeless dress. I don't think it was my mother's idea of a style she wished to copy.
The following evening we had the full rehearsal. I was rather nervous as it was to be my first time outside my home really while dressed as Kim, but I was not alone, James and Philip were just as anxious. Ms Jones had altered things so they fitted better, and soon we were remembering lines and the play was unfolding. Mr Watts was directing and making us do the occasional line again, while his assistant was taking notes. So afterwards we had a time where he went through the notes, offering advice then rather than disturbing the flow of the scenes. He made a few comments about my position on stage, but James and Philip were asked if they could try to be more feminine and convincingly female. Later mother approached Mr Watts and offered to help with the boys before the play was to start for real. He agreed and for the weekend my house became a school for making boys into girls. Father was told he might prefer to go for a golf weekend which he snapped at and was gone from Friday morning, making it easy for me to bring James and Philip home from school after classes on Friday afternoon.
Mother had collected our costumes during the day and Ms Jones had offered to come round to help as well. The evening started with mother giving us a peep talk and brief run down on what she hoped to achieve over the following two days. Clearly James would not learn how to walk like a young girl and an older woman, but if we managed feminine our instructors said they would be happy. I had an inkling of what was to follow, the boys started with bare foot walking, following a line, book on head, no looking down, then a few hand gestures before dinner was served. As the five of us sat down mother made a little speech about how she considered this to be a girls only weekend, she expected all our behaviour, speech and gestures to reflect that, starting with eating. We then had a quick lesson on how a proper lady would eat, and we all dutifully copied her.
I thought I would get an easy ride, having done all of this in the weeks before, but none of what I did seemed good enough. Maybe this was to make the boys feel better or maybe I had let my standards slip once I thought I had mastered the part. We spent the Saturday wearing our outfits with full make up and wigs, so we got used to seeing each other and not being an odd gender mix of boy and girl. We did more elegance training but this time with our stage shoes on. Then as we mastered one aspect something extra would be added such as carrying a clutch bag or wearing a wrap. Then doing jobs around the house like making our beds, or helping with some chores, until finally she gave us boys, (or should I say girls) an apron each and had us prepare our dinner for the evening. Ms Jones disappeared to arrive later in a very nice what might be called proper going out frock. She then took the three of us upstairs to help us change into our cocktail dresses, gave us tips on touching up our make up. Before coming down to find mother changed as well and offering us flutes of champagne. Mother asked and I easily complied with a request to help serve the meal, Jane and Philippa clearing away later, before we settled down cocktail glasses holding various concoctions, Jane and Philippa's being non alcoholic as they were younger.
The boys both had made big improvements in their efforts to be more girl like, and enjoyed the praise the woman gave them. Somehow the topic of why we had been chosen for these particular parts came up, Ms Jones thought it obvious, Jane and Philippa's voice had not broken, mine had but was not very deep, coupled with our body shape, for boys we were slight and in my case short. I suddenly realised that even when I had kissed Paul and wearing my heels I had had to reach up make the contact, and then remembered a film where I had seen an actress reaching up and as she kissed stood on her toes and lifted one foot clean off the floor. I decided to try that myself come the final rehearsal.
I knew I could sleep in my lovely nightgown if I wanted, but as the boys prepared for bed they too were offered similar nightwear so they could stay in role making the morning easier. They had been enjoying the day so it was no surprise to find out both of them had slept in satin that night.
Sunday followed a familiar pattern of doing everything trying to think 'how would a girl do this', only now some extra things were added once we had done our deportment session, wearing just our wigs, a robe over our nightgowns and our highest heels. When mother was happy that we had retained our skill of walking in heels elegantly she ushered us all into our respective bedrooms with tube of cream, telling us to follow the instructions and use the en suite showers, then we were to dry ourselves and use a second tube of moisturiser to massage into our skin. I am not sure what we expected but when we came out wearing just a robe, knickers and no body hair, it was definite we were all a little shocked, but were reassured that you never see a woman with hairy skin so that was the reason for our special showers. We all had satin robes that went with our nightgowns and it was clear from the way we were touching ourselves that I was not alone in finding the sensation of smooth fabric on bare skin fantastic. We were all told to go and choose something to wear for the day and to make a start on our faces, one of them would come and make sure we were doing ok in a minute.
Half an hour later we were all ready, I caused quite a stir as I choose my sun dress that was not among the play outfits and clearly something extra of my own, I picked it for it's soft cotton material and I was not alone in choosing for sensory delight, Jane was dressed in a silky dress and Philippa in a soft blouse and skirt, both wearing tights possibly because we had worn them on the Saturday but quite possibly because they felt nice on their legs. We were all spritzed with perfume given some jewelery, nothing small and discrete off course, long strands of beads around our necks, big bracelets, and noticeable rings. Then five minutes of practice at standing still, which was harder than it sounds if you want to look elegant. Before we found our aprons and prepared a lunch to take outside and eat on the lawn.
Mother and Ms Jones gave instructions and laid out the rug and crockery, but then made sure we did everything as femininely as possible, making us walk in and out with the dishes and plates of food so we had plenty of walking to do, then we learnt that girls can't sit cross legged when wearing a dress or skirt, 'Don't want to show the men your knickers' was the simple explanation. So we all sat on the rug with our legs tucked under us while we ate our picnic and drank some cool refreshing sparkling wine. It barely took two small glasses for us to get the giggles, and then when Jane lost her balance reaching over to pass me some strawberries, ending up sprawled on the grass, mother gave us a stern telling off, saying we were behaving like silly little schoolgirls. We all sat up straight and snickered into our glasses as we tried very hard not to giggle some more. It was not long after that, that we finished and cleared everything away.
Mother's next session was to put a CD one of Sex in the City the other High Street Musical. We were not to take that much note of the story, what we were to do was watch the women and take note of what they were doing. She started us discussing gestures when a woman gave a look that only women do, a smouldering come here look. She would rewind and play it again, then suggested I try it as it might fit in well in a scene. It took a few attempts before I was told I had it. Pretty soon we were all commenting and pausing the CD and trying out moves and gestures we had seen. By the end I swear we had forgotten we were 3 lads, we looked and behaved like 3 girls, posing and having fun in front of each other.
We had dinner earlier, about six. We continued to watch the CDs while mother and Ms Jones went to start the meal, then we were told to go and dress for dinner, meaning cocktail dresses. And like good girls we all went off to get changed only this time we did it together, Jane and Philippa bringing their dresses into my room, where we changed and helped each other with our make up. We made an incredible picture once we were nearly ready, Jane was changed and finished sitting on my bed hugging my old teddy bear, Philippa was sat on the edge of the bed pulling her tights up and I was at my dressing table applying lip gloss. Jane suddenly came out with 'this has been fun, hasn't it.' we all turned to look at her. 'well it has' she said defensively.
'Yes it has' I agreed
Philippa stood to retrieve her shoes from across the room 'I suppose so, I really wanted a part in the play so was prepared to accept anything and was getting terribly worked up about the whole acting a girls part, but now I think it will be fun'
'That sundress of yours, not just this weekend like us then?'
I went on to explain how I had been practicing for a few weeks and had indeed worn a dress earlier that week, Jane in particular let out a small wow, this had impacted on her more than Philippa I thought, then in a quite girly way that we had seen on a film we all climbed onto the bed and hugged each other. It had to be at that moment that mother walked past the door, 'Lovely to see you all getting along so well, I just came to tell you dinner will be five minutes'. She walked out and we fell in heap on the bed giggling.
Going to school on the Monday morning was difficult, we had been thoroughly checked over for make up remains, we only physically had our bare skin to show for our weekend changes, but I for one felt different. I no longer felt one of the lads, I had to tell myself to slouch in the chair and put my hands deep in my pockets in an attempt to counter the feminine gestures and poise that I was recognizing in my actions.
It was wearing off by Tuesday, but at rehearsals that evening they all came back, as well as the three giggly schoolgirls, Kim, Jane and Philippa, who fortunately had a changing room to themselves. Stage make up is much uglier than real normal make up which looked great when done well, but we had to be seen under the lights, so we had no choice. This was our last proper full rehearsal and it went well, the members of staff involved complimenting the three of us on finding our inner woman, and praising mother and Ms Jones on doing such a good job. They said it was easy, we were eager students, something we were not sure how to take.
After we had finished and mother was driving me home, I mentioned that James and Philip were boarders, she said she knew that, so I expressed the idea that during the three performances they might like to stop with us so they do not get teased in their dorm if they happen to forget something, 'like what?' she asked. 'Like not getting all the make up off, walking like you have taught us, flicking a wrist, anything that could be construed as girly' She agreed and said she would have a word with Mr Watts before Thursday.
Thursday was the first night and all the cast were given the afternoon of classes. I went home with James and Philip so we could find some where to relax before we had to make our public debut as women. Mother had other ideas and suggested we each go into our en suites and go through the hair removing routine once more. She did this to get us into a girl frame of mind I realised later, but for then I just enjoyed the creams I massaged into my skin and worked my way back into the role of Kim. It was a shame we had to go to school dressed as boys it took some of the edge of the time spent showering. But soon we were in our own little changing room and preparing ourselves for our first scenes.
The play went very well, we fluffed a few lines and one person missed his cue altogether, but I was enjoying myself and remembered to do my tip toe one legged kiss with Paul, it just felt so girly, I also thought I was fantastic at the part.
After the close, mother drove us back home still in our cocktail dresses we had come off stage wearing. All three of us full of our new experiences and making comments about who was good, who got things wrong. Once home after a small supper, we went into my bedroom to get ready for bed. It was Jane who asked if my kiss was as good as it looked, I told her we were only acting, but both of them said 'Oh yer' in a disbelieving tone. Pretty soon we were in our nightgowns and in separate beds, reliving of what had happened during that day.
Friday and no school for the cast. It was funny to see how easily we reverted, this was clear when we all turned up for breakfast after father had left in our nightgowns and matching robes. Mother referred to us as girls all morning while we did some school work and played in a very girly way when taking a break, just gossiping and complimenting each other really. Lunch was very civilized as we naturally seemed to just behave as we had at the weekend. Then after some time watching TV it was time to go and get ready for our second performance.
If the first night was full of nerves, the second was smoother as we all relaxed a little and got nearly everything right. Paul did unsettle me though. Just before the kissing scene we were in the wings when he said 'Are you ready for your kiss tonight,' 'sorry about last night, was not quite prepared for a real snog.' I turned to him and with a flirty look continued 'only acting dear' he smiled back and for the first time in my life I thought 'this man is attractive', then thought 'wow, where did that come from?'.
We had a standing ovation, eventually leaving the stage buzzing with excitement. Once again mother drove us home still in the costumes, but with the stage make up cleaned off. Father was home but enjoying a documentary on the TV when we got home, so we had our supper in the kitchen then adjourned to my bedroom where we behaved like three teenage girls who had drunk way too much coke. We were giggling and gossiping about the boys we knew, and even got to talking about the reactions we were getting of the boys in the cast, and when Paul was mentioned I think it was Philippa who stated that he fancied me, I might claim to be acting the 'kiss' but he was not. I quickly moved the conversation onto a boy called Gerard who was very friendly and protective of us when we were in the wings, his job being to move props and get the actors on stage on time, so we saw quite a bit of him. Eventually mother put her head round the door and suggested it was time we settled down and went to bed. Obediently we did as she suggested.
Saturday morning and I was wondering how the day might pan out, but early on I heard my father get up and leave the house, presumably to play golf with his mates. So when mother called 'breakfast is ready girls' we all knew exactly how to appear in the kitchen for our cereal and juice meal. Long ago we had been told by mother 'If it is good enough for this girl, it is certainly good enough you girls'. We sat round the table in our robes, teasing each other over which boys might fancy any one of us.
Mother came in and told us to stop being silly, we are only acting. Then asked if any of us had anything planned for the morning. We all said nothing, so she suggested that as our last day as her girls we might like to spend it together as girls. We all three of us looked at each other, and then they both looked at me, their hint that it was for me to reply. 'What do you have in mind?'
She went on to suggest that the matinee was at three, with the last performance at seven, with the after show party following that. So we had until two and it was just turned nine, so if we were up for it she suggested that we might like to have some real girl fun and go shopping. Once again we all shot quick looks around the table.
'Where?' I asked,
'nowhere close, I thought the big new shopping mall up the motorway'
'And as girls' Jane asked
'Off course, boys are no fun at shopping, girls are the only true shoppers'
Another quick look around, and almost as one we said 'if you are sure?' or something like that.
Her response 'Off course I am, I would never have asked if I had not meant it. Now shift those pretty little arses and get dressed.'
We were chattering up the stairs expressing how this could be so scary or absolutely brilliant, none of us sure which way it might come out. Once in their bedrooms, Jane and Philippa let out delighted squeals and came running into my room carrying what they had found on their beds. We all had a long top and a pair of thick leggings. 'Where did these come from?'
'I don't know, I guess mother, are we going to wear them?'
Jane was the keenest 'I have seen lots of girls wearing these styles, she would not buy them just for us to ignore them. It will have to be the black shoes though and they are so high, my feet where killing me after just a few hours in them, I could be ruined by the end today'
Mother then made her entrance 'So girls, you have found my treat, those stage clothes are not appropriate for teenage girls, that is why I choose something more suitable for today. Now off and get ready I want to leave in thirty minutes'
'What!' we cried and ran off get ready.
Forty five minutes later we are all sat in her car wearing our new outfits, soft make up on and unfortunately heels on all our feet. Mother drove and made conversation with us asking about what school was like, what the other two planned for the future, about their parents. General stuff adults ask young people about, but at no time did she suggest why she wanted to take us shopping.
We started by mingling with the crowds, getting used to being out and very much in public, no excuse that we were in play or rehearsing now, though it was really, at least I rationalised it that way. Then we went into a couple of department stores and just mooched around the rails. Mother fingered clothes on the racks, occasionally picking something out and holding it up. In time we copied her, Jane was the first to pick out a white lacy top and ask what we thought, mother said her bra would be seen, Jane replied that was meant to be the idea. This was followed by going into an upmarket boutique where mother found a nice short summer dress, and after a quiet word telling us to behave, she went into the changing rooms, coming out to ask our opinions. We all said it suited her, so she bought it. I could tell she would have loved to have a daughter but for whatever reason she had a son, which normally made such shopping, delights impossible, so she was making the most of her opportunity. The last shop we went in before lunch was a jewelers, she knew the school did not allow ear piercing, but she felt that a necklace might be acceptable, if worn inside our shirts. So she asked us all to pick a necklace so we had a memento of our time as her girls. Philippa picked a plain chain, I choose a more delicate rope necklace, Jane however went for a very intricate chain with a pink stone pendant on it. I think that said something about our levels of commitment to this new way of life we were learning.
All too soon it seemed we were going back home. Mother thought it might be good if we went to the theatre in our opening outfits then all we needed to do was stage make up, and no word of objection was raised by her three girls. Mr Watts greeted us at the door, 'Welcome ladies, looking divine I must say, you have certainly come prepared. Ready for the final round girls. And Mrs Edwards are you coming along to our after show party? We have room booked at the Jubilee Hotel just down the road.' We left them chatting as Mr Watts seemed to being a little OTT with mother and her efforts to turn us into passable female actors.
The matinee went smoothly, lots of pensioners in the audience who were not really that good at picking up the comedy, but did clap heartily at the end. Jane said her gran went to anything that had cheap tickets just for a reason to go out, so maybe there was lots of Jane type grandparents out there just in the theatre for something to do on a Saturday afternoon.
The evening was different, many parents had tickets for this one, a lot lived some distance away so Saturday was a good day to make the trip and see what their sons had been up to at school, while spending their money on an education. My father would be there as well as mother, Philippa said her parents were planning on making the long trip from their posting in Scotland down to London for the play. Jane however was not so lucky her parents were diplomats in China and she would not see them until the summer.
The show was the best with everyone out to prove themselves before their parents it seemed. I was doing my best to play my part as convincingly as possible, maybe a little too convincingly, because, by the time we had got to the kiss scene, me and Paul had got the flirting looks off to a tee, so come the embrace and I am stood on tip toe, I felt myself being lifted off the floor as he pulled me up to his lips. I am not sure how many of the audience knew that I was in fact Russell most of the time, certainly my father, and as he held me and kissed I could not help but think 'this could be an awkward conversation later'. Kiss over we finished, took our bows and encores. Then there were speeches to be made, people to be thanked, flowers to be given. One of which was for mother, Mrs Grace Edwards made her way out of the audience to receive her thanks for helping the 'girls' in the cast, who were then presented with bouquets themselves, we curtseyed and said thanks to Mr Watts while we all blushed a bright crimson beneath our heavy make up.
Back stage everyone was hugging and patting each other on the back, we were all on a high. Parents started to come back and congratulate their offspring. Father appeared and slapped me on the back, not to hard thankfully 'Jolly good show that, enjoyed it enormously, Grace had been saying you was putting everything into this one. She was right' I was wondering if he was pleased with having a son dressed in a cocktail dress and heels. When he came out with 'one day I must tell you about some of the things we did as students, make you smile I'm sure' and with that he gave me a hug and asked if he should call me Kim while I was looking like a daughter. I said Kim would be fine, 'Right well then Kim, you have a party to go to, I have a table booked for me and your mother, so if you give me a call when you are ready to leave, I shall come and pick you up'
Jane was looking a little lost so mother included her in our family for the moment, giving her a hug and telling her how good she had been. Reality came back when Philippa joined us, 'Our clothes are at your house, what can we wear to the party?'
Mother came over all apologetic, she had forgotten to pick up their bags and so until they got to their dorms all they had were stage clothes. 'You could go as you are, those are party frocks after all.'
Just at that moment Gerard moved into our group, 'Well then ladies, would any of you like me to escort you to this party' we all looked at him.
Mother chipped in 'Well it looks like at least one of you has a date. Gerard remember to be a gentleman won't you' he put an arm over Philippa and Jane's shoulder.
'I'm afraid you are not included, I think Paul would fall out with me if I made a move on his girl'
'What!' I said
'Just ask anyone, we all have you two down as an item'
Just then Paul came near. 'Paul. Have you heard this, Gerard says everyone thinks we are dating.'
His response was to step over to me, kiss my cheek, everyone cheered. 'So it seems' he then turned to my father, 'Good evening Mr Edwards, Mrs Edwards, do you mind if I escort your beautiful daughter to the after show party?'
Mother got in first 'Off course Paul, you go ahead and enjoy yourselves'
As Paul said thank you to my parents he took my hand and lead me out into the evening air for the short walk to the hotel. Closely followed by Gerard who was walking between my girlfriends, one on each arm.
The party was great fun, Paul and some of the older boys had sneaked in some spirits and added it to our soft drinks, which just made us behave even more girly, like the champagne had before. There was music on, but only the brave danced, except for a couple of boys who asked female staff for a dance and Mr Watts who asked each of us girls for a dance. For a slow dance Paul and I were pushed onto the floor, followed by Jane and a willing partner Gerard. We did what seemed like a very long shuffling waltz until the song ended and I could make my escape from the clapping party. I grabbed Jane and said 'Ladies. Now'
Once in the safety of the room no man will go into, 'What are we doing?' I looked at her, she was very pretty in her silver tube dress. 'We have school on Monday'
She took hold of me and pulled me into a hug. 'It is ok, everyone knows the truth, just enjoy the moment, see where it takes you. This might never happen again, if Paul wants to kiss you, let him, worry about Monday on Monday'
'Have you and Gerard, you know....kissed?'
'Only a quick one, nothing like your stage snog, but who knows'
'You think we should just....... well for tonight anyway'
'Yes, now come on, Philippa might be wondering what we are doing in here'
We walked out the door to find Paul and Gerard waiting for us 'Just like real girls, hiding in the loo for a gossip'
'It was not like that at all, Kim needed to freshen up her lipstick and I needed the toilet. Now then Gerard Mann you were making some rather interesting suggestions back there' she took his hand and walked away from the function room towards the hotel lobby.
'So just me and you' I said
'You are totally believable you know, I don't know how you did it but from that boy we did our first read through with to this, I would have said impossible, but now I can tell you, if there was some way to keep you as my girlfriend I would jump at it.'
With his flattery and Jane's words echoing in my ears, I reached up put my arms around his neck, pulling myself up to his lips.
'Oh my god, is this how a girl feels?' I thought to myself. Paul put his hands into the small of my back and pulled me to his body 'When did he learn to use his tongue like that, ummm very nice' my mind was drifting while my senses enjoyed his attention. Then for some reason I was kicked back into reality, I have school on Monday as Russell. Then after a moment of indecision I felt his lips and tongue press on mine and thought 'Enjoy it, who knows it might never happen again' and pulled myself towards him for more urgent kissing. And a very interesting time which might never be repeated, so I just let go and stopped thinking of Monday, enjoying the moment.
Second Life
by Lauran
Some while ago there was a news story about a marriage divorce happening, the cause adultery, but the man had never meet his mistress. They meet online in a comunnity called Second Life. The wife was given her divorce.
*****
She moved gracefully along the concourse, her skirt flicking up as her hips swayed and the knees pushed forward, the metallic green sleeveless dress looked fantastic as she dropped onto a pavement café and ordered a latte, the waiter came over and gave her approving smiles and moved onto another table.
It was five minutes later that the smart suited man that was expected, turned up, he leant over and gave her a greeting kiss then sat next to her, her hand gently slid onto his thigh and caressed the inside. Within seconds it seemed the waiter was back with an espresso he had ordered as he walked into the cafe.
They made small talk, then rose together and walked away, the waiter paused a moment and with a knowing smile watched them leave. It was a short walk to her apartment, as the door shut she released the bow which held her metallic green wrap around dress fastened, as it fell to the floor it revealed some very nice sheer stockings held up by a fine red suspender matching the red thong and lacy bra which was pushing her large breasts into a stunning cleavage. He stood transfixed as she removed his suit slowly, eventually he was just in his boxers which she pulled down his legs, as she reached down to his feet, her lips wrapped around his erection, his whole body stiffened as his pent up emotions erupted through his penis and into her mouth. This was just what she wanted; he would be erect again but more in control so she could have her fun without him finishing without her.
‘PETER, where the hell are you?’ the scream seared into his ears.
‘OMG’ he thought Carol is home, he had been so enjoying his time in second life he had lost all track of time, and now he was trying to shut down and hide the history before she came in.
‘You’ve been on that all afternoon? Be a love and make me a coffee I am knackered and still need to send some e mails’ he had shut the screen down but the link was still there if she looked. He had to leave it or look suspicious, so rose to give her a guilty kiss before heading for the kitchen to make her coffee.
He hoped she was just going to do e mails then stop for the evening, but she was a long time before she appeared in the living room, he could hear her in the next room busy typing most of the time, but he still had to ask ‘Lots of e mails going there’
‘Not all mail, doing some research as well, fascinating what you can find on the internet these days’ she gave him an odd smile that unnerved him slightly.
The next day he logged onto second life, the first message was from Guy ‘you left all of a sudden, I was having fun, can we make another date, xxxxxx’ followed by ‘just had a weird conversation with you but it did not sound like you, has someone taken your identity?’
Peter quickly replied ‘Sorry I left so quickly, yes to another date, I was having fun also xxxx. Victoria. xxxx. Not aware of being copied what were they asking?’
Peter got his avatar dressed for the session, the red silk mini today he thought and no underwear, but the red spike courts will look good.
‘See you at the café in five’ the message said.
Victoria walked the same path to the café, her red dress rippling around the top of her legs; Guy was already there with a latte waiting, she flicked her long blonde hair back to kiss him firmly on the lips.
‘So the odd conversation with someone impersonating me, tell me about it’
‘Not much to tell, you had disappeared then half an hour later you contacted me, you said hi, then started to chat, it was not till later I thought it odd, and the questions seemed queer’
‘How queer?’
‘Well like you were asking things you already know, like how much I look forward to our meetings, how your pink dress is my favourite, and that you are the best partner I have ever had, in bed and out’
Peter did not reply immediately, could Carol have got into his character and pretended to be Victoria?
‘Sorry, I was thinking, how about we finish of what we started last night?’
Guy’s image rose and took Victoria by the hand, soon they were behind closed doors, she had swallowed his first load and he was pumping away in her hole hoping she would come before he did; she arched and pulled his arse to hers.
‘Fucking brilliant’ Victoria announced
Then after a few more words they parted and Peter logged off so he could get on with some household jobs.
Carol came home in a better mood, he made her a coffee and unusually for her went straight for the computer, he had tidied everything up this time, but there was still the nagging worry that someone had impersonated him and the bigger worry that it was Carol.
That night Carol wore her sexy nightie, then sucked Peter off then made him ride her until she came. When she had stopped panting she looked him in the eye, ‘Not bad, did you like it?’
Peter muttered something but was worried about the similarities to the Victoria and Guy sex, but put it out his mind eventually falling asleep.
Before he knew it Carol was shaking his shoulder, ‘Come on sleepy head, you have so much to do’
‘But it is Saturday; let me have my lie in’
‘Not today, I have something special planned for you’
Peter got up wiping the sleep from his eyes, before the first of many unexpected, uncalled for and unprepared for events happened, Carol passed him her short silk robe with the words that cut him to the quick, ‘This will help get you in the mood, Victoria’
The silk wafted around his shoulders, he was instantly awake ‘What?’
‘You heard Victoria, it seems you have been hiding your delights from me, I thought it might be nice to bring Victoria from the virtual world into the real world’ she smiled at Peter with a look that conveyed several thoughts the main one being ‘don’t cross me’ but there was also a sense of fun in there, ‘Now lets get on I have so much planned for Victoria today and the clock is ticking already’
Peter was trying to think quickly, she knew about his second life but how much, she had called him by his game name and then the sex the night before was that a coincidence. Rather than challenge her he asked what she had planned
‘Oww just enough to see the real Victoria, now bathroom and let’s get started’
Without a better plan other than fighting, Peter complied with the added notion that he could be about to learn an awful lot about being a woman, something he had always dreamt of.
Within the next hour he had shaved all the hair on his body he could see, then Carol finished the job clearing his arse crack and back, then to his embarrassment shaved his pubic hair into a neat triangle. Next he was shown what she expected him to wear, first it was a very tight thong which held his man bits all tight into his body, which to Carol’s delight had no pubes showing at the sides, next it was the chest, she was well organized, the glue worked so well that his generous breasts hung from his chest in a very convincing manner, and then when supported by his new bra and matched to his skin with make up from the neck down Carol declared him female.
A more worrying event was about to loom into Peter’s life, Carol dressed him in a loose sweat top and pants, then with a beanie on his head Carol informed him they were off out, he tried to point out he did not need to go out to experience a woman’s world, especially as his chest was most definitely unmanly. His defiance was quickly blown out with a few short words and a very good stare which meant business; soon he was in the passenger seat, the seat belt nestling between his breasts and feeling very uneasy about where the destination might be.
His worst fear appeared in front of him as she parked the car beside her usual salon, he had never dared enter before, so he knew they did not know him, but also knew they would soon know him far too well, and that would be on top of what Carol might have already told them. Sharon invited them in and had a quick word with Carol, the words he picked up were ‘as discussed’ ‘you sure’ ‘at least’ and ‘definitely’ which did nothing to reassure Peter’ nerves.
Then Sharon came over to him, ‘Apparently Carol wants you to look pretty and stunning, I feel I should make sure you will cooperate with everything we have booked here, and that you agree to let us do whatever is needed to achieve the result Carol tells us you want’ Peter gulped and considered what would happen if he walked out now, one Carol would get a serious look on her, and two this was a once in a life opportunity. He nodded his consent and Sharon lead him to the shampoo sink, from then on for next few hours his life was in their hands.
The smells of the salon brought back childhood memories of sitting while his mother had been given a perm, he was half expecting the perm to be his fate, but he was intrigued when after the bleaching products had done their work and his shaggy mop had been trimmed, that Sharon started to fiddle with his hair, soon he saw that she was attaching foot long extensions to his own shorter hair. This he was informed would take some time so Helen was going to do his nails at the same time, but Sharon politely asked if he would not move his head which meant he could only feel his fingers being manipulated as Helen worked.
He had no choice but to sit quietly and patiently waiting for the women to finish their tasks, Helen finished first, and after two hours of immobility Sharon asked if he would like a coffee, he relaxed and saw his fingers, long square French tips finished the tips of his fingers, ‘Wow he thought, just like Carol’s, they are fantastic’ then his attention moved to his hair, he had been aware of the increased length but now he turned to get a good look in a mirror and touch it with his manicured fingers, he always liked long hair and this fulfilled his dream, running down his back and in front of his shoulders he admired it’s length and colour fully, ‘I just need to tidy up the ends and sort out the fringe and I will be done with you, would you prefer a sharp end or feathered?’ Sharon had brought him back to the real world, this was his hair and he had to decide, he suggested feathering the ends. She quickly finished and then to his disappointment fastened it back. ‘I will leave you in Leah’s hands now, then I will just get you all neat before you leave in a bit’ Sharon smiled at him and left.
Leah stepped up, ‘Hello, someone is going to a lot of trouble, must be something special for all this. Now I have some ideas and Sharon has told me of your suggestions, so if you don’t mind I shall just ask you to relax and let me work my magic’ Peter tried to relax but her words about how much effort all this was taking struck home, why was Carol doing this to him, but then he felt the first of his eye brow hairs leave it’s follicle in his forehead and he started to worry about the why and the afterwards as what seemed like every hair was being dragged from it’s home. Next he was having lotions, creams, powders and liquids applied to his skin, he had some idea what might be happening but had no idea what the end result might be. It took Leah half an hour to finish, her final comments being ‘I have used good long lasting products on you so there will be no need to do any repairs, but there is a lip wand if you want to give your lips a little more of the wet look and a mascara to use if you need to use it tomorrow.’
Tomorrow Peter thought, what does that mean. Sharon was back and brushing his hair out, placing the fringe so it swept across his face and gelling it in place. She was fussing around when Carol returned and gave Peter a smile which spoke of satisfaction, ‘You are wonderful Sharon, that is just perfect’ then turning to Peter ‘and you my dear are more beautiful than I ever expected, I hope you like it’ Peter was about to say something when Carol asked ‘Sharon, the ears?’
‘I was not sure, the studs are supposed be in while they heal’ Sharon defended
‘Why not pierce them, remove the stud and insert the hoops, then they can heal with the hoops in’
Sharon had made her point, she was not keen, but asked Leah to do as Carol asked. Peter soon found himself flinching as the needle shot through his lobes followed by a lot of wiggling as she tried to insert the ear rings Carol had supplied.
Peter was now allowed to take a long look in a mirror while Carol paid, ignoring the baggy clothes he was looking at sexy woman, stunning eyes, creamy lips, long blonde hair flowing past his face and resting on top of his full chest, and then there were the gold hoops showing through the hair, 3" across if he was not mistaken, he brushed a hair from his face and saw the nails. This was too much, it was brilliant. His reverie broken by Carol, ‘Come on plenty of time for that later, I have a few more treats for you in store’
They thanked the women and left, Peter feeling a little easier about being out in public now that his face and hair made him look very female, which was far better than being a man with a big chest.
As they drove home Carol chattered away about nothing in particular, all the time Peter was wanting to ask ‘Why?’ but not having the courage to really want to know the answer as it might be something he did not wish to hear, he settled for enjoying the moment, reveling in the sensations of his long hair, the inconvenience of his nails and the throb in his ears reminding him that beauty comes at a price.
‘Now then’ Carol spoke as she pulled into the drive ‘I shall prepare some lunch, you slip upstairs and slip into the things I have left out, and then we shall eat.’ She looked for his approval.
‘Now you mention it I am hungry’
‘Well then Victoria you run along and I shall see you in a few minutes’
Peter was hit with his avatar name again, just what was she up to? He found on the bed a pair of jeans and a white satin blouse, none of which proved easy to get into, first he had to be careful taking the sweat top off without harming his hair, next the blouse would not fasten up because of the boobs pulling at the fastening, so he had to settle for leaving it unbuttoned from the neck to the cleavage, then the jeans were tight and needed to be pulled up with care as his nails were getting in the way, then he found the shoes, white pointy toed heels, he had never walked in heels properly before and now he was on something like a 3" narrow heel and hoping his balance did not leave him, a few circuits of the landing and he heard Carol tell him to hurry up. His clicking heels announced his entry to the kitchen, ‘you look the part now, here eat up dear, I have few more surprises for you once you have eaten up’ Peter looked at the salad and yoghurt before him, Carol saw his face ‘Don’t be daft, you cant eat your doorstop butties now you are a girl Victoria, this is full of all the good things you need plus it is low on calories, now eat up’
Peter ate his salad and accepted it as part of this peculiar day, a glass of water to wash it down hardly added to the experience. An experience he was not ready for followed lunch. Carol tutored Peter in how to walk in the heels so he had the poise she felt he would require if her plans were to work well. She was giving him tips on how to place his feet and then how to hold his arms and hands while he walked, he was getting towards a wiggle, but then a cruel thought arrived in her mind, if he held his buttocks differently then maybe that would do the trick. It took seconds to find what she wanted then called Peter into the bedroom, told him to lower his jeans and lay face down on the bed, it was then Peter experienced his next new experience, Carol pulled the thong to one side and inserted the tampax tube in his arse and withdrew it leaving behind an ultra towel. A gentle slap on his bare buttock, she then told him to get up, and meet her at the front door.
He approached the front door his buttocks felling strange and clenching slightly, which had the effect of making him walk with a sway, the walk pleased Carol, she handed him a shoulder bag, ‘Now for the next step in your female day, follow me’
Peter was now a little more nervous, his last outing had been to the salon and look what that had done to him, but on reflection, nothing terrible had happened, and nothing had happened that he had not dreamed of in the past, so his throat went dry, but his feet walked to the car. Thirty minutes later Carol parked the car outside a parade of shops, ‘Now I reckon your taste in underwear will be stockings’ she looked across at him, a glint her eye ‘so how about we go in and pick up something nice for you to wear’
Peter was steeling his nerves as he looked at an up market ladies shop, ‘Come on don’t think about it to long’ Carol was out of car and closing the door before Peter had started to move, remembering the tips Carol had given him he walked carefully towards the shops, ‘Relax’ she whispered ‘walk easy, now come on’
They entered the most feminine shop Peter had ever been in, Carol fingered along the racks, Peter was clearly uncomfortable so Carol took the lead and picked out a white lace suspender, then a red satin one, ‘Any preference?’ Peter looked around and fingered some himself and realized he was a child in the sweetie shop; soon he was walking out with a bag full of goodies he had only dreamt of owning.
‘Right now Victoria I have another treat for you at home, fetch you bits and lets see you done up like a proper lady’
That reference still worried Peter but the bait of looking as Carol indicated meant he would go willingly into the future. After a drink he felt much calmer, and Carol wondered why she had not thought of slipping a small dose of her tranquillizer into his drink before. He was so much easier to guide now that he stripped of and dressed without prompting in the cream satin knickers and suspender belt, then rolled the sheer gloss tan stockings up each leg and clipped them on, ‘Now for the real treat, slip the bra off dear and step into this’ she took a deep pink dress from it’s hanger and had him step into it then pulled it up his body. Carol took care to tell him how it should fit and how it fastened. The pink dress was a halter neck with wide cups that came up from a waistband that circled the chest just below the breasts then fell as a flaring skirt to the thighs, covering the stockings with a good margin of modesty, she clipped the fastening on the back of the waistband, and tied the tails in a bow, that made the halter, behind his neck the excess was hanging down his back, before she gave him his white shoes, she settled his tits into their supports, he was feeling their weight but said nothing, the dress was a soft cotton that caressed his skin so gently it made his skin goose pimple. The shoes were to be a challenge she knew, he had coped with the heels in the afternoon but these white stilettos were higher and only had a toe cap and ankle strap to maintain the contact with the foot, but she had felt them perfect like the dress for his special day. The buckles fastened she told him to take a few steps, much to her delight and she felt his also, he walked without much trouble in the new higher heels. A few circuits of the house and stairs and he was looking quite confident, and from where Carol was looking the dress was moving well and his legs and hips had a lovely wiggle to them. Peter however was realizing that he now looked just like his character in second life, Victoria. She had long blond hair, elegant nails, big hoop ear rings and he was wearing a pink halter neck dress and white stilettos, which was a favourite on his alter ego, Victoria, when meeting up with Guy. Being Victoria was both a thrill and a fear all rolled into one, he loved the image but dreading where it was going.
He had little time to think, besides his mind was not working to well in it’s relaxed state, so when Carol clipped a wide gold bangle to his wrist, and a neat watch to the other, then slid three dress rings onto whichever finger they would fit and declared him ready and showed him the full length mirror, she knew she had him, he posed before the mirror turning this way and that, stroking a hand up his leg so it lifted the hem of the dress. ‘Now a few final touches’ first scent, then the lip gloss and last a white clutch bag. ‘Now I think you are ready’ she kissed his cheek ‘Come along Victoria I have one last treat for you, though it is likely to seem quite familiar when we get there. First I want you to practice your walk while I change; it should take me a few minutes not all day like you, but who knows you might be that quick one day. Now off you go and remember to move your hips.’
Peter was trying to guess what she was up to as he walked an imaginary line placing his feet on it and letting his hips move compensating for the rotation. Carol shouted from the bedroom ‘Nearly forgot, between your legs is a string, pull it and get your tampax out dear’ a few minutes later he left the toilet to find Carol dressed in a smart trouser suit and looking very sexy,
‘You look very nice’ he commented
‘Thank you, but this is not for you, this is for me, I am hoping we both enjoy ourselves tonight, come along’
As they rode in the car Peter plucked up courage to ask where they were going, ‘I thought you would have worked it out by now Victoria, maybe not the exact where but at least the situation’ she paused while she manouvered a junction ‘I thought a coffee shop would be a fitting place to take you’
‘How much do you know, and why are you doing this?’
‘Not sure I know everything, but certainly enough, I am surprised you like the pink dress best, I would have gone for the green metallic if it was me, but Guy insisted the pink was the favourite’
‘You spoke to Guy’
‘Yes Victoria, he seems like this guy will do a Guy’ she laughed at her own joke ‘Now let me see if you can imagine where we might be going’
Peter starting to sweat, how much did she know ‘The coffee shop near the library in town, and what else has Guy been saying?’
‘Look in my bag and get my roll on, it will stop your arm pits sweating……... No not that shop, the one in the square by the Midland Hotel’
Trying to calm his rising nerves and join in ‘That is a nice one’
‘I thought so………. Guy knew he could find it as well’
This hit like a bolt ‘Guy is coming, how?
‘Didn’t I mention it, I had a most interesting time with him this morning, while you were enjoying Sharon’s care, I was online and learnt a lot, fascinating world second life, and Guy is such a nice bloke. That’s good luck a parking space’ the sudden change of topic and parking jolted a raw Peter
‘You did what’
‘I spent a while looking through your profile and virtual world, you do have a nice wardrobe, and I have to say Guy is a looker, and showed me how you like to spend your time together’ Peter made some odd noises ‘Sorry didn’t catch that, lost your voice?’
‘What have you done? It was only a bit of fun’
‘A bit of fun? Lots of fun I think, but I think reality is far better than the virtual’
Peter was catching up quickly ‘You have got Guy to come here, that is why I am dressed like this and going to a café’
‘Brilliant isn’t it, luckily Guy does not live in another country, he only lives about 60 miles away, so I have invited him to come and live out your second life, isn’t that a fun treat’
‘What have you done, you know I am not a woman how could you put me in this situation, you have got him here to meet a woman that does not exist’
‘Shut up, you are that woman; you are Victoria, just look at you even I am impressed how good you look.’ They were out of the car and walking towards the square ‘He has come all this way to meet Victoria, and that is what he will do, you will wiggle your arse down to the café, you will give him that passion filled greeting kiss, drink your latte that I didn’t know you liked, all the while giving sly touches and caresses just wanting to get up and walk your seductive walk to his room where you reenact your passionate scenes from second life, then some time tomorrow morning you shall wake in his arms etc etc’
Peter is petrified at what Carol is proposing ‘But he thinks he is meeting a woman I expect, I am not what I appear to be, this could go terribly wrong, you cant have thought it through. Please I will do anything just don’t make me do this, please’
‘Too late for pleading, if I had not found out the other night, how long would your affair have gone on? No I have spent an awful lot on you today so you could live your fantasy, I had rather hoped you would thank me’
Peter tried for another tack ‘He might not be nice in reality; I doubt he is like his avatar, what if he is ugly, smelly and rude’
‘Well then you will not be the only one lying will you? Now get that walk into gear, and live your fantasy, and don’t worry I shall be watching from a nearby table, just to make sure you don’t get in harms way, and to make sure you do everything Victoria loves to do’ Carol said the last words with a particularly stern smile on her lips. ‘And you need not worry about recognizing him, I asked him to come dressed smart like we know he does, and he will recognize the pink dress for sure he told me it was his favourite as it looks real sexy when you walk and he loves to help take it off when you close the bedroom door, so that should be easy for both of you.’ Carol was enjoying this but her eyes were not smiling, then a pat on Peter’s bum ‘Run along, you don’t want to keep Guy waiting’
And with that she walked across the square towards the café. Peter stunned momentarily then realized he was standing alone and there was a man walking past him staring at his legs and smiling. Quickly weighing up his options, go back to the car, Carol has the keys, somehow get home, that means a taxi or bus, and he has no keys, go to the police and tell them he has lost his memory, or he has been the victim of a cruel joke, he could hear them laughing already, or walk to the café and hope Guy bottles out then Carol would drive them home.
As Carol had taught him he wiggled his hips to the café, feeling the soft fabric play around his body and legs in a delightful way, the breeze gently blowing the dress about. Selecting a corner table as far from Carol as he could he carefully settled himself into a chair, the waiter took the order for a latte and left. He was assessing all the men who he could see, even grading them casually from ‘I hope it is not him’ up to ‘he would be fine’. Then he jumped, from the opposite direction Guy had approached, ‘Victoria?’ Peter startled said nothing ‘Sorry I didn’t mean to make you jump, you look just like a friend I was supposed to be meeting here’
Peter having regained his senses ‘Guy isn’t it’ he confirmed and lent over to kiss his friend on the cheek, Peter froze a little, but got over the ‘this is a man kissing me’ phobia and relaxed, mainly because he knew Carol was watching him, but also knowing he had to play the part at least until he revealed his true identity. The kiss over, Guy orders the espresso he always had when with Victoria, and made small talk about the weather and the traffic, Peter is keeping his voice to a loud whisper hoping it sounds feminine enough. All the time taking in the man sat next to him and stroking his hand very softly, he was not the athletic build of the avatar, more a man who could have been fit but is carrying a few extra pounds but stills look smart and very presentable, definitely well past half way on the earlier man grading scale he had used when he first arrived.
Then they moved off the small talk, ‘You look beautiful, the real life is way better than your second life, and that dress is wonderful, I am so happy you decided to wear it’ Peter returned the compliment and asked how Guy had got there and if he had any plans, just so he knew how to handle the deepening crisis.
Guy had driven up after his mornings session on second life with Victoria, which unknown to him was Carol, who had encouraged him to drive up and book into a hotel so they could get to know each other better, and just having had virtual sex the prospect of real sex was to tempting to resist, and Carol had expected this in her set up, and was enjoying the unfolding scene as Peter, beautiful as he appeared to be, was being flirted with by a man who wanted to have sex with her husband.
Right then Carol was distracted when a man sat next to her, it was Sean a colleague from work, recently separated from his wife and someone Carol enjoyed the company of, and had been there when he needed an ear to listen and a friend to hold as his life fell apart, but he was stronger now, and the friendship was flourishing. ‘You seem very interested in the couple over there, do you know them?’ Sean asked
‘Sorry’ Carol replied ‘Just watching, do you think the woman is beautiful?’
‘Don’t try and trap me with that one’
‘No not a trap, just something about her intrigues me, what do you think?’
‘Well she is not a attractive as you, but I suppose some men would find her attractive, maybe a little to big up front and flaunting it, attractive yes, but not my type unlike you. Is that the right answer? She is that man’s type though, he really fancies his chances there I reckon’
Carol lent over and kissed Sean passionately on the lips ‘I guess I got that answer right then, what do you fancy doing this evening, I haven’t eaten so food would be nice’
Carol had to tear her attention of her husband who at that moment was flaunting his assets in the direction of a man who was going to get a big surprise sometime soon, she just hoped it would happen quickly otherwise she would have to imagine the scene where Guy finds out Victoria is a guy and it all kicks off.
Over at the other side of the terrace Guy is asking why is there a woman staring at them, Does Victoria know her? Peter is getting deeper into his crisis, Carol his wife is sitting with another man, a quite good looking one according to his scale, and has kissed him with more passion than he would expect her to kiss a friend, and Guy is asking who she is, does he say ‘My wife, she set this up to get at me, don’t worry you are just a pawn’ which would cause a scene, so Peter decides the best way to deal with the situation is to distract Guy from noticing the ‘staring’ woman and flirt as Victoria would in second life, he had done it in the virtual world, surely he could pull it off for a while in the real one.
Peter finishes his latte and lets Guy know it would be nice to move on, Carol was making him feel very uncomfortable and he would rather let Guy down without her watching. Guy paid at the till and as he exits Peter gets up to leave with him, ‘Where now?’ he asks
‘Anywhere you fancy’ Peter replied
‘Well I am booked in at the hotel round the corner, but I haven’t eaten since you invited me up here. We don’t eat in second life but this is different’
‘We could eat’ this would buy him time while he worked out how to escape this nightmare.
Carol watched as Guy walked up alongside Peter and slides his arm around her husbands waist, Peter never flinched and continued to walk with the grace of a woman, she was getting disappointed but as they turned the corner had to let the image go and concentrate on her more manly partner sat beside her.
The arm on his waist felt very nice and reassuring, and the feel of the clothes was tingling his raw senses, ‘If this was for real it would be great’ he thought ‘If we eat, Guy relaxes with a few drinks then I can maybe just walk out, or tell him the truth and he will be chilled enough to have a laugh and we just be mates’ he hoped this would work because it was the only plan he had working at the time.
‘So Victoria, where should we eat, this is your city’
Peter suggested an Italian a few streets away. The meal was fine, Guy was flirting even more, he had discovered the suspender clips through the dress and voiced his approval, another thing Peter did not approve of was the way as the evening air chilled his fake nipples reacted and grew, pushing big nipple sized bumps out in the front of his braless dress, and the following thought of what would Guy and any other man looking think when they saw them. Peter was also finding that he was enjoying the attention, he had never seen himself as attractive, but now clearly Guy was attracted, so until the charade was ended he went with the role in which he found himself.
They were holding hands a lot and Guy was doing his best at flattery which going down brilliantly, Peter was even responding positively and doing his best to think how a girl would respond in the situation, he was flirting, running his foot along Guy’s leg, and doing the ‘Would you like to try a bite of mine’ then feeding him with his fork.
Guy was getting all the right signals, for all the wrong reasons. The bottle of wine finished, Guy asked for the bill and paid it. Peter had to think quickly, reality was about to hit soon and he hoped to survive the truth. They would obviously head for his hotel room next, Guy has come for sex and that was not going to happen, the truth had to out but not in the restaurant, on a busy street then he might be safer thought Peter.
He picked his moment, ‘Guy, you are great and I have had a fantastic time, but there is something you should know’ this was hard work for Peter.
‘That your real name is not Victoria, I know, that someone has been playing with our lives, I guessed that this morning’
‘So why did you come, to humiliate me?’
‘To find out who you are, I was intrigued that someone I thought I knew suddenly changed, and none of us are 100% truthful in second life I’m sure, so I fancied finding out who had been giving my character such a good time, besides I might get to meet a gorgeous lady and have terrific sex myself’
‘Guy. I’m a man under all this, please don’t hit me, we have been set up’
‘The woman at the café?.............. Besides you left a few clues to your real identity, I guessed you might be a very interesting man, and no I could never hit you, you are gorgeous and so far I have had a great time’
Any one who had cared to watch would have seen Peter visibly relax as he realized he was not about to be beaten up or abused in some way, ‘I am so sorry for deceiving you I just set up Victoria as a bit of fun and it sort of escalated till I couldn’t wait to log on and continue being that person, I really enjoyed being her, but the reality is I am not her. Thank you for being so understanding and kind’ Peter lent over and gave Guy a kiss on the lips more out of relief than passion, but it was a kiss.
Guy was thinking quickly also and had worked out the situation and what he could get out of it, ‘Tell you what, I have a double room, why don’t we go there, have a drink and see where we go from there. You are still one great lady Victoria, no matter what you say you walk so sexily, you look so pretty, and those nipples just scream, well better not go there I suppose’
Peter was close to tears, he had survived possibly the most humiliating moment in his life. Guy had been so understanding he could feel the anxiety draining from him and a euphoria filling its place. ‘Guy I am so glad you came’ and then flung his arms around Guy’s neck and kissed him.
They moved to the side of the pavement and used a wall for support while they kissed in a way Peter had never know, Guy just controlled him, he was taller and Peter was on unstable heels, so as Guy responded Peter just submitted to his advances.
It seemed like ages but was possibly only a few minutes, ‘Now Victoria, I have a bottle of nice wine in my room that needs drinking, would you like to help me?’
Peter just took his hand and let Guy lead him to the hotel, unsure of what might happen next, but so relieved that Guy was being so lovely. They walked the few streets to the hotel, Peter able to enjoy to the full the sensations of the dress, his breasts bouncing in front of him, the hair tickling his bare shoulders and the affected walk his heels were making him do, besides which he was living out his fantasy of being a girl with a man, and that man clearly didn’t mind it was a fantasy which could never be real.
Guy picked his key up from reception and showed his girlfriend to the stairs, the receptionist gave them a knowing smile as Guy placed a hand in the small of the woman’s back guiding her towards his room.
Once inside the second life scenario ended, Guy did have a bottle of wine, and they did take a glass each and sit on the bed talking, hardly the passionate embrace that normally followed the closing of the door, but this was real and Peter needed to get used to the situation, no matter how much he was enjoying it.
Chatting had been easy all evening and Guy explained how he had grown suspicious of Victoria that morning, and how he had found out some of the true Victoria. They talked of how they saw their avatars and what they enjoyed of their second lives, by which time it was getting late, ‘You can stop if you want, I guess you don’t have any plans right now’
Peter was nice and relaxed, the offer seemed very appealing, ‘No plans, right now I have no idea what waits at home, indeed if I am welcome there at all’
‘That’s decided then, you will stay here, let me use the bathroom first please, then you can do whatever ladies do for so long in there’
Guy reappeared five minutes later in a toweling robe, for some reason Peter was not quite sure why, but he was standing by the door waiting and as Guy came out he said ‘Thank you’ and kissed him, Guy responded taking his friend in his arms. The kiss turned into something more than a thank you, Peter was hugging and caressing Guy as much as Guy was fondling Peter. Then Peter had an OMG moment, Guy’s erection was unrestrained and pointing straight at him.
‘Guy I am so sorry, I never meant to get you excited, I shall go and clean myself up’ he tried to break away but Guy held firm.
‘Victoria I bet I am the not the only one who has felt this way tonight, you are the perfect woman, I would love to see where this goes, real life is different to fantasy, but I reckon we can still have fun if you stay with the Victoria character’
Peter was still in his elated state and replayed what his character would do now, he pushed Guy against the wall undid his robe, kissed him and let a hand wander down the man’s body till it was touching pubic hairs, this was a first for Peter. But at the same time another first was happening, Guy was undoing the bow that held the dress around Peter’s neck allowing the breasts to hang free, then he undid the fastener at the back allowing the dress to fall to the floor.
‘Victoria, I hope you don’t mind me saying, you are even better without the dress, I am not sure what is real and what is fantasy, just that I loved you online and I love you even more in the flesh’
Peter was high on the kissing and returned to tonguing Guy, then the idea came to his head, Victoria nearly always gave Guy a blow job, and so with one hand holding the erection Peter lowered his pink lips onto his first penis, swallowing as much as he could, he had done it plenty of times virtually, all he had to do was transfer that knowledge to this hard on. He suckled, and ran his tongue along the underneath all the while gently going in and out with his lips, each time seeing if he could take a little more into his mouth. Then it happened, Guy tensed and exploded inside Peters pretty mouth, he automatically swallowed the semen as it filled his tongues taste buds with new pleasures, so filled with the ecstasy of his first successful blow he kept on sucking and licking until Guy’s penis was empty and going limp.
Guy pulled his Victoria up to his mouth and kissed, ‘that was the best ever, you sure about this?’
‘No, I am not sure, but that felt so nice, I wish you was able to take me like you do in second life’
The embrace renewed and Guy’s erection returned Peter knew this was how it worked online but to find the penis touching him again was unbelievable.
‘Victoria I have never done anything like this, but the next thing we usually do is fall into bed and see where it goes’
Victoria was now taking over Peter’s thinking and just wanted to see what this man could do, sitting on the edge of the bed undoing the heels before climbing under the sheets next to his/her first boyfriend. It took a while but in the heat of the moment they found out that Victoria had a nice tight hole very close to where a real girl would have a regular love hole, and to both of their surprise and pleasure they discovered that Victoria screamed when the prostrate gland reacted to a penis rubbing against it, then collapsed exhausted. ‘That was brilliant, I always dreamt of being here, and now it is real I cant believe it’ then cuddling up close and Victoria fell asleep.
The morning brought new realities, Peter only had the clothes he had walked out of his house in and they seemed inappropriate for a man in the morning, but then having fake breasts stuck to his chest was not helping. A trip to the bathroom with the lights on added to his helplessness, his hair had been in his face when he woke and it looked a mess, his face though still looked good, the gloss had gone from his lips but beside that everything looked just as Leah had done.
Back in the bedroom Guy sat up in bed and smiled as Peter walked in wearing nothing more than a thong, ‘You still look stunning Victoria, do you want some breakfast?’
‘Well yes I am a bit hungry, but what happens now, how do I get back to my real life, the one I had last week, how do I get home, what happens when I get there, just what has happened to me, I loved last night and you are so supportive and kind but….’
‘that was quite a speech, I know that to me you will always be Victoria and I will be there if you need me, now lets get dressed and go down for breakfast, then we can sort out your life’
Peter took ages to get dressed and feel happy with the visual result, his hair was not gelled so was falling in his face all the time, he still was not sure if the make up not washing off was a good thing, but for the immediate future it was a bonus as he had no idea how to do it himself, Guy was only to happy to help him put the dress on getting a last cuddle in before fastening the dress at the back and behind the neck. A little over dressed for a Sunday morning, but his body shape meant it was his only choice.
Guy was a good man and his offer to drive Peter to his home was easy to accept. Guy’s car surprised Peter a new Mercedes, which is a very comfortable car to be driven in when going to an uncertain future.
Guy stayed in the car while Peter walked up to the front door, the woman he recognized from the café opened the door the man who had been with her stood behind her in the hallway, there were some words, he could sense Peter getting upset, and then the woman gave him a small suitcase and a letter, then shut the door leaving Peter standing on the doorstep. He turned and looked at Guy and walked towards the car. Guy without a word got out of the car, opened the boot and then the passenger door, putting an arm around his girlfriends shoulder, took the bag and shut it in the boot. Then silently drove away.
Carol had had a great night, Sean had taken her for a lovely meal, then onto a club, finally they got a taxi to Carol’s home, and she was so ready for Sean the front door was hardly shut before they started. Peter had not wanted her for ages, she had needed to work longer hours and when she came home late he would always be on the computer, and in months they had hardly touched let alone kissed, so Sean had thought his own sex desert was ending as the evening progressed, indeed it did end several times as Carol seemed insatiable.
He was confused when the ‘flaunting’ woman turned up and Carol had some harsh words with her and gave her a bag and a letter, then shut the door in her face. But once shut Carol turned on him and had his trousers undone before he could ask ‘Who was she’ a tongue in the mouth only added to his speechlessness.
Peter sat quietly in Guy’s car as he drove away, the envelop lay on his stocking covered thighs, until looking at it was getting to much, and it had to be opened to find out the contents.
Victoria
Best I write this down so I don’t forget anything.
I hope you had a good night, I am hoping mine will be.
You should be reading this on Sunday, so you will have found out your breasts are well fixed on, the glue I am assured will last 3 weeks. Leah’s make up is good for two weeks before it will start to fade, but the new eye brow shape is with you till they regrow. The extensions can be cut off, but they are good for 10 weeks which is very good apparently. The nails are acrylic and will damage your nails if you remove them, if you keep them you will need to get them filled every few weeks as your own nail beneath grows out. The ear rings will just pull out and heal, but what the hell with everything else why not keep them.
In the bag are your clothes, don’t think you might find anything useful, just the clothes you wore yesterday some extra pants and stockings but only enough for a few days. Being the nice person that I am I have found you a green wrap dress like the one in second life, I thought it your best choice, hope you enjoy the reality of it. I am guessing that was all you wanted, if you want the rest of your boring unsexy male clothes they will be in the charity shop if you want to buy them back.
I have had a moment of sympathy for you, going to work on Monday might be awkward for you, I have considered leaving you to sort that one out, but as I am such a nice person I have rung your work and told them you are sick, but not how sick I think you are, that gives you a week and then you will need to get back there, I am loving the thought of you trying to remove all those wonderful alterations I have done to your image, or not being able to get changed back and turning up for work looking so different.
One last thing, I really hope Guy, or whatever his real name is, is as repulsed by your fantasy as I am.
It will be no surprise to you; I am going to find a solicitor next week.
Good bye you sicko.
Your soon to be ex wife
Carol
Guy was getting more concerned as he drove, his passenger was starting to cry and get more agitated. He had no idea what he should do next or where to take his fantasy woman. A supermarket car park looked empty so parking in a corner he comforted Peter, telling him the usual things like, things will sort themselves out, there is always a silver lining to a cloud, like I say the usual glib untrue phrases. Then he read the letter and was fuming.
‘Right that does it, maybe she wants a divorce but there was no need to do this to you, did I tell you I work for a law practice? I will make this woman suffer’ he thought for a moment ‘I think if you come home with me, I am part of the reason for you being here, so let me help get you out of it.’
Peter was struggling to get his head around how his wife had dumped him, then Guy is offering to take him to his home, was that wise? Did he have any alternatives dressed how he was? ‘I am screwed aren’t I? Are you sure about taking me back to your home, will no one mind, I could find a hotel while I sort myself out.’
Guy was in a serious mood now, ‘it is no trouble, I live alone in a nice large house with plenty of rooms and space, I also work a lot so you might not see me even. You are more than welcome to stop as long as you need to’ Peter said thank you and told him how kind he was, Guy continued ‘Today is Sunday so most shops are shut, tomorrow we can get you back to your more natural look, then see about you filing against your wife for everything we can think off, and then think of getting you back to work. How does that sound?’
‘I can’t believe you will do this for me’ Peter reached across the car and kissed Guy before he realized what he was doing ‘Sorry that was wrong’
‘Don’t worry I am having trouble imagining what you might look like when you change, I still have a very attractive woman sat next to me and I am more than a bit confused’
‘I have no clothes; I shall need to buy more’
‘Men’s or women’s’ Guy said with a smirk on his face.
Peter started to laugh for some reason, he was calming down now ‘thank you’
‘No problem, tomorrow we get you some solvent to remove the breasts, make up remover, we find a hairdresser and work out how to clear your nails, but until then probably best if you stay as Victoria, are you ok with that?’
‘No problem, I would like to get into clean clothes though, hopefully there should be enough in the case’
‘Right then Victoria we have a plan sorted, home, change, rest, get you sorted, and that woman truly sorted’
‘Has anyone called you a knight in shining armour?
‘No’
‘Well this damsel in distress is telling you that is what you are’
‘Thank you’
They set of to drive the hour left of Guy’s journey home, sitting mostly in silence the only conversation was started by Peter
‘If I am to be Victoria until tomorrow, please would you treat me like you did yesterday, I quite like being your girlfriend, I never expected to when I was sat at the café, but I have surprised myself how much I like being Victoria for real, virtual was interesting and fun, but reality is so much better, do you mind’
‘You can be my girlfriend whenever you want, I enjoyed the virtual too, was intrigued by the events leading up to last night, and enjoyed the reality far more than I ever expected, you are one special lady no matter what Carol says’ a few tiny tears rolled down Peter’s cheek as he allowed his relief to show.
Soon after they arrived at Guy’s home, as he said a bigger house than one man needs, but he said it was an investment. The décor and general feel was of a bachelor, Guy did the host part of bringing the case in, making a coffee, then showing Peter to the guest room where he was able to undress, shower and put on clean clothes, with the choice of jeans or a green dress he went for the jeans thinking maybe the dress would give out the wrong signals. All clean and spruced up as well as he could manage he went to find Guy who was busy preparing a meal. Without thinking they kissed as Peter walked over to stand by Guy, and then asked if he could help.
‘Just get the wine out and we are about ready.’ He put a salad bowl on the table ‘I don’t think you realize what a gorgeous lady you are, even in jeans you look hot’
Peter smiled back ‘You possibly don’t realize how nice it is to be told you are attractive, but I only had this or a green wrap dress which I thought might be wrong given the circumstances’
‘If you wanted to walk about naked I would see nothing wrong, you just wear what you fancy and don’t mind me.’
Over the food and wine they discussed more of what Guy intended to do come Monday, but as they talked they both realized how much Peter liked being Victoria and how much Guy liked Peter being Victoria as well, so they revised their plan. First they would take some photos to prove what Carol had done to her husband, then they would get whatever products were needed to undo the work that had been done on the Saturday, but they would only buy them and keep the receipts, they would hold of using them for a week as Peter’s sick would be up then and he would need to become a man again for his job. Which could give the appearance of his getting cleaned up without actually doing it, and then they could enjoy each others company for a week. Guy did stress that Peter for the best effect would need to appear wronged even humiliated by his treatment so he would need to be discreet and back in male mode before going near his home town. But a week of fun seemed a delight.
Peter tidied up after the meal and Guy went off to do some work, an hour later the kitchen was spotless and Guy had finished so he could watch some sport on TV. Somehow they both ended up sitting together and Victoria cuddling up to her man. Carol had taught him so well about walking that even in jeans and bare foot he wiggled his arse, making Guy keen for some fun.
‘Would you like me to take care of that’ Peter said as a manicured finger stroked the front of Guy’s trousers. Without an answer the finger undid the fly and released the excited part, Guy was having trouble controlling himself in the situation and when the pink lips once more swallowed the head he was soon squirting his semen into his lover’s mouth, who thanked him by licking it clean. They transferred to the bedroom undressed in anticipation of what was to come, neither were disappointed and enjoyed it even more as they used lubricant to help with the fun, Victoria this time knew what to expect and made Guy do all the right things, so when the orgasm came it was a delight if exhausting. There was no surprise that the guest room was not slept in after the love making had been so successful. What was a surprise, at least to Peter was that in two days his world had changed so completely that he wanted to be Victoria and stay with Guy forever, he wanted to wear dresses and heels, have make up on his face, wiggle his walk and have Guy fuck him, in a perfect world this is what he wanted, he hoped it was what Guy wanted also.
Guy was up early and away to his office to tackle the weeks work, but was back at lunch time. His assistant had been sent out to find appropriate solvents etc and to buy a new set of clothes for a man, he had only the sizes for Peter and no idea what his taste was, but the story of a man being totally femininised intrigued him so he took care to do the job properly.
Over lunch Guy and Peter discussed the future, Victoria could stay but to be safe would need stay out of sight just in case Carol contested the fact that Peter had not enjoyed the experience, and going about as a woman would be damning evidence. Once the week was over Peter would definitely have to renounce his feminine form and return to his job, find a place to stay and get his life back, Guy would take care of the divorce and settlement. That all seemed fine except for the week of hiding so Victoria could have some more time around Guy, it might feel like a prison. But of the more distant future they could only dream.
Victoria put up with the indoor experience and enjoyed the time with Guy, who not only enjoyed his lover but also a very clean house and fresh meals every evening for a week. Over the weekend Peter lost all his charming good looks and Guy had to get used to the sight of his lover being a real man. Peter had found a friend at home who could put him up for a few weeks ‘while he got himself sorted’ and that was it Victoria was deleted.
Guy kept in touch as he pursued the ex wife, but it was very business like when they spoke. But then one day after Peter had found a small flat to rent and got a computer connected to the internet he was looking once more on second life, he had changed his log in and covered up his tracks so Carol could not accuse him of being back on there, but Vicky was back, hair shorter, she had trousers in her wardrobe because after a week at Guy’s he had found the jeans very comfortable for daytime wear, but he still had some very sexy dresses that if he meet the right man would be just right for that nearly realistic liaison. As I was saying one day after Vicky had returned the avatar was sitting at a pavement café, when a good looking man came and sat beside his avatar, ‘I have been looking for many days hoping to find you here’ he started ‘you have changed, not sure I like the trousers, but the top is very nice’ he ordered his coffee and they chatted like old friends, eventually walking off together to a place a lot more private.
Six months later Guy was able to tell Peter that his wife had accepted she had been unreasonable in her handling of the separation and would pay all costs including compensation for Peter’s humiliation. The house was on the market and a buyer was eager to complete as soon as possible. This meant a celebration, Peter spent some of his savings on a new Vicky outfit, but the hair was a wig and the make up not so well done, nor were the breast forms as they were just placed in the bra cups. They had a meal at Guy’s and then a session in bed, but it was not the same.
‘It’s my fault, I’m sorry’ sobbed Peter ‘last time was so much better, the masquerade far more accomplished, this is hopeless’
Guy comforted his friend but really longed for the original Victoria. Peter was up first and dressed in his male things making ready to return when Guy appeared ‘if I was to set it up for you to spend at least a week here as Victoria would you come?’
‘I doubt it, I can’t see the point in not doing it properly’ Peter answered dejectedly.
‘In that case if I make enquiries so you can do it properly, would you be interested?’
It seemed strange for Peter to tell another man ‘Off course I would, did you keep the clothes from before?’
‘Off course, so you will do it, please let me arrange things with salons etc and then we can have you back as we both want you to be’
Over the next week Peter booked some leave, and Guy did his arranging asking Peter what was required, until finally Peter drove down to a shopping mall near Guys and was once more transformed. His hair was long enough now to be cut into a page boy style and streaked, his chest was enhanced with realistic C cup silicones, his fingers had only just grown out of the damage the last set of acrylics had done but he allowed new almond shaped nails to be fitted to his fingers, his ears were repierced, and then for a new look he was given a spray tan. When he walked out to meet his lover in the pink dress and spike heels no one except those who cared to look very closely would suspect Victoria was anything but Guy’s ultimate wet dream. Which in reality the pink dress and what it enclosed, was his ultimate wet dream.
Another story about what might happen when the secret is out and the closet door flung open.
I hope you enjoy my rambling
It had been a normal sort of day at work, the usual jobs that got done or put off till it became more urgent till they got finished. Followed by my usual drive home stopping at the store to pick up some fresh food to make the evening meal with. I was expecting the usual welcome at home, son slouched in the front room watching TV or playing on his PS, making a drink while I prepared the meal and nagging Sean about not doing anything around the house while he was on holiday.
But the normal ended that evening. I got home to find Sean reading the computer and a few telltale signs that he had found my secret case. On the computer was a site I recognised, one like this with cross dressing tales on it, on the table were some magazines and on the floor the case in which I stored my feminine clothes. This was not a good thing to greet anyone after a days work, I had to switch from laid back get things done and relax mode, to wide awake how am I going to handle this situation in an instant.
'Hi Sean' I started 'what have you got there?' stupid question as I knew exactly what he had, all of Stephanie's possessions.
'Dad?' uncertianty in his vioce, Sean was unsure how to handle the situation as well.
'I think we need to talk son' now there was an understatement. Should I play it down, try to dismiss it as something that happened years ago, maybe a response to Kay's death, his mum and my wife, should I be frank and honest, I could even have a breakdown and try to get some sympathy as I seemingly crumpled under the strain of goodness knows what.
'These aren't mum's are they?'
'Well no,' I had to say something, truth or lie 'they are mine' there we are, a start at least with an honest answer, 'let me try to explain'
Even though Sean might be your average sixteen year old, full of uncertainties about who he was, not sure what the outdoors are for when on holiday, alien to style, smartness or even at times soap, I knew under the facade he was a good caring kid. We had lost Kay five years ago and with the help of his grandparents had managed to raise him to be a decent lad. So I decided he could probably handle the truth, he had coped with the grief of seeing a mother die, this should be easier.
'You see I am what is called a cross dresser, maybe not like the ones you have come across on the websites. I just like to wear female clothes at times, it is nice, a bit of an escape, relaxing, but also has a bit of thrill and recklessness added in as well.' Not bad for a quick resume.
I went on to explain how I first started dressing when I was about ten with my sister in games and make believe stories to entertain a younger child. I moved onto his gran's clothes stored in the loft before giving it up when I married, but once I was widowed I found myself drifting back to the dressing for some sort of escape from the reality of how sad I was, pretty much the same emotions Sean had had only expressed differently. He had been withdrawn, my mother being his support as she was not quite as raw as his other gran or myself, and we came through it, he was still quiet, I still dressed.
I tried to keep it calm and Sean being Sean was thoughtful in his expressions, not giving much away. Fortunately no histrionics or anger, he did ask some questions though, like did his mum know, which she did, I had been honest with her though she disapproved. There was of course the 'why do it?' question, straight answer, 'I don't know' and tried to explain how it was just a part of me.
The evening wound down after the trauma of being discovered, I tidied everything away, we discussed how we felt about not having a woman in the house. We had not talked of Kay for well over a year but this brought her up and we talked openly about missing her, and how I was glad Sean had been around as it helped me cope with my loss. There were many positives to be taken from his discovery, but what hung over me that night and into the next day was how he would react to the fact that his dad was a trannie. He might go back into his shell, rebel and go of the rails, expose me to family and friends. I was doubting whether honesty had been the best way, but lying would have been so hard to handle, for me then and possibly in the future as he would certainly find the truth. At worst I rationalised I get banished from the family and he goes to live with one of his grandparents, a poor outcome I know and not one I wanted, if only I could have kept my desires under control and just been a regular dad to him.
Before I went to work the next day I bobbed into his room to say good bye and ask him to tidy the kitchen, hoping to keep things normal, but did ask if he was ok after the night before. He grunted something that sounded like ok from under the covers. I left him not knowing how this revelation was going to pan out.
I was not to sharp at work, my thoughts constantly drifting of to think about dressing and Sean and the future. I drove home wondering what he might be thinking and dreading opening the door. The first thing I noticed was the kitchen was clean, then the tv was off and music was playing, the nice soul music we both enjoyed. Then I got the shock of my life, he came to the kitchen door said 'hi' and I nearly fainted as I turned from the kettle to see him. He was wearing my black stretchy dress, a bob wig, tights and black heels, there was red lipstick, mascara and eye shadow but not well applied. I was speechless, so he stepped into the silence, 'I can make your coffee' I must have continued to stare, 'so how do I look?'
The kettle clicked off and he went to get me the milk as I poured the water. Then we sat down and he told me about his day. How he wanted to be angry with me for not being normal, how could he bear the embarrassment of knowing I was one of them. Then he thought about Kay. Next he logged onto some websites luckily not the porn type ones, saw some pictures and blogs of people who seemed to be enjoying life even if there were some issues going on with them, he also commented how good looking some were, especially the young ones. So sometime during his day he had got the case out once again and sorted out an outfit he liked and tried it on to see what all the fuss was about. By the time he had finished talking I had prepared our meal with his help and were sitting down to eat. I had to ask as he seemed to be coming to the end 'And how does it feel?' he did not actually have to say anything, his smile told me enough, he smoothed his hands down his dress as he sat, then brushed some hairs from his face. 'I think I get it' was his reply.
This left me wondering if the storm was over, he was not about to go screaming pervert at me, but was this an acceptance of me or had I encouraged him into a life of internal and eternal conflicts about who am I and why do I want to look like a woman.
I slept a little easier that night, and was better applied to work the next day, but returning home was not a comfortable moment not knowing what to expect when I opened the door. I was pleased to see some housework done and the table laid for tea, the tv was on and Sean was lounging in front of it, back to normal I thought. Had the past two evenings been a dream, we went through our routine of pleasantries, thanked him for his help, ate, then he went off to one of his mates till late, which left me alone with an opportunity I used to consider as Stephanie time, maybe a long scented soak, a quick change and relax in the front room. Whatever I might have done, I was in uncharted territory, he knew, so what if he came home and found me dressed, what if I spent the weekend dressed, maybe I should seriously think about shaving my legs. In the end I did nothing but went on the computer to look at where he had been surfing curious to see what sort of information he had been seeing. To my surprise it was not all ladyboys and she male sites, there were sites that talked about how to hide your male features, where to get make up, clothes and more intimate stuff, as well as blogs mainly from younger men who were pretty good looking I had to admit. I wished I could access his e-mail to see if he had written to anyone, but maybe that was pushing his privacy too much, it would be nice to read what was peaking his interest though.
It was Friday evening that the dressing subject cropped up again. A very big trannie who could never disguise his frame as being anything but male even with surgery was pictured in a TV magazine advertising a programme 'transvestite wives' not that we watched it but Sean commented that he did not get anyone wanting to be ridiculed as a man in a dress, but he could see the appeal of nice clothes in private and if you were good enough then going out as a girl could be something of a thrill. He asked how good I looked and if I had ever been out, I told him I was eight out of ten at my best, and I once went out late at night to post a letter, nothing more just a nerve wracking short walk.
I asked him what he had found out on the computer which lead us into talking about different sorts of dressing, I was relieved to hear he was not interested in the more bizarre branches but just stuck with the basic looking like a girl. So I ended up asking if he wanted to go shopping on the Saturday, being naive he asked 'what for' I said to get you some things of your own so he could dress if he wanted in clothes he chose and not my more mature styles.
That night I wore my favourite nightie, the first time I had dared when he was at home. Then in the morning we both did some cleaning before I asked him if he had decided about going shopping. He clearly had thought about it and asked the obvious question, how? I told him we just go to big stores try to look as if this is something ordinary like buying food, hopefully people think we are buying gifts, but what if they think we are buying for ourselves, they don't know us and probably don't care. I could tell he was still unsure so I suggested a trip to a shopping outlet village some way away, we look around if he sees something I would go back, pick it up and pay for it without him. This seemed to get his approval and we were off.
We got there for lunch which was good because we could eat a burger and watch people passing by and comment on what things we liked about the way girls dressed. We soon had a good idea what we were looking for, tunic top, leggings, ballet shoes, or a short dress and heels. This proved to be easier than I imagined, yes he was nervous, but from a distance he would pick out what he liked. Soon we had leggings and ballet shoes, easy stuff. As the shopping continued he got confident enough to let his fingers browse the rails, maybe father and son in the ladies section was unusual but no one seemed to take any notice, it was busy and lots of men were there, mostly with partners admitedly but we were not the only males in this female enviroment. By mid afternoon we had found his two outfits, had bought some make up to add to my selection and bought another coke. This gave us chance to consider what we had done, and give him the chance of returning anything he was not keen on, or the whole lot if he wanted to forget the whole idea. He said no, he wanted to keep everything, I did suggest he take the shoes into the gents and slip them on in a cubicle to make sure we had the right size, gently reminding him to take his thick socks off first.
We were home for five and unloaded his bags from the car. 'What now?' I asked 'do you want to try something on?' he nodded a yes. 'Do you want me to help you with some make up' he mumbled a no and disappeared to his room. An hour later he reappeared in his cream and pink dress, tan tights, cream heels, my longer blonde wig and a perfectly made up face. I looked him up and down and told him how pretty he looked, then gave him a hug, I could feel tears welling up in my eyes, this was such a relief to have him accepting my fiobles, even embracing them.
'I was going to make some tea'
His reply was unexpected 'Dad would you get dressed as well please' I did not need asking twice, after asking to make sure, I was into my room and stripped before I had thought about what I might wear. seeing as he chose a dress I went with that, my LBD, black stockings, 4" heels and my bob wig. Finished off with some jewelry and scent. I came into the kitchen to find 'son' putting a chicken salad on the table.
'What do you think?' I asked as I stood in the doorway.
'Oh dad' he came over and hugged me.
'Whatever is the matter,' I soothingly said into his ear as I hugged him back.
'It's wrong this dressing up as women'
'No not wrong, unusual yes, but if you enjoy it where is the harm?'
'I have had such a great time today, and you look great, and it ought to feel wrong, I should want to be a boy because that is what I am, I am confused by all this'
We hugged and told him I knew how he felt, I had been through the same confusion, self doubts, questioning, but if we harm no one and enjoy it, then why not do it. I wiped his tears and told him to go and repair his make up, thinking that he might just as easily clean everything off and come down as a lad.
He was too quick for a complete change, he came in looking good again if a little puffy around the eyes. We sat and ate his meal and opened a bottle of white wine, this time I did not water his down, he had been so understanding about the whole situation I felt it right I treat him more like an adult than a kid at that moment. We talked about how he had done his make up so well, I knew he had been in my make up, but not by how much, he had been on websites and practicing on himself while I was at work, until he was pretty good. He must have spent hours looking in the mirror to get that good, I was impressed.
It was a lovely evening, after we ate, we sat and watched the tv, well we spent a lot of time watching each other, I wanted to see just how feminine he was. I was not sure why he was checking up on me though. The end of the evening was good as well. I was able to change into my nightie before cleansing my face and going to bed, he even saw me through the bedroom door and made no comment other than 'Does that feel as nice as it looks' meaning the full length nightdress I had on. So I pointed at the drawer I had moved my other ones too and suggested he chose one to try. He took a short pink one, shoe string shoulders and barely covering his arse. Very pretty.
Sunday we had breakfast in our night clothes and rather disappointedly had to dress more coventionally as we had offered to visit my parents and help with their garden as they were struggling to maitain it. It was a fairly unforgettable day of weeding and eating my mother's cooking, all except for her getting me in a corner and in a hushed whisper telling me she thought Sean had been wearing make up, I just said lads his age try lots of things, I knew about the mascara, he does it to make his eyes dramatic when he is going out, seems to work as well. She just tutted and muttered 'not in my day' sort of words. I did tell Sean he had been rumbled and what I had said to cover for him.
Monday everything was back to normal, Sean at school, me to work. I would get home to find him doing school work with the tv on, he was coming up to exams and was taking them seriously. If you did not know about the previous week end and the days before, you might never know what had happened, that was until Friday. On Friday evening I had decidded that I could let my barriers down a little and shaved my legs while in the shower, then filed my nails to a neat curve. But it was after Sean had gone to bed that I got a more significant decider. I was locking up when he came downstairs for a drink, nothing unusual in that, what did take my attention was that he was in the pink nightie. I said nothing just went to bed in my own.
Come the morning I was sat eating my toast in my cream satin nightie and matching wrap when Sean appeared in his pink nightie but with his bulky cotton dressing gown on. Once we were awake and talking I asked what he fancied doing that day. He said he had some homework to be in for Monday, so I suggested we go and get him some new nightclothes. He smiled and said thank you.
We were back for lunch, two nighties, one long, one short and a long silk wrap, plus a pair of fluffy slippers. He went to his room I thought to try them on but was gone too long, so was not surprised later as he came downstairs in the green tunic and black leggings outfit, again beautifully made up and looking like a daughter once more.
Once I had done my errands and outside jobs I too changed into a casual look of satin blouse with neat straight denim skirt, hoping to compliment his female look. He spent the rest of that day and the following in a combination of his feminine clothes and mine, stopping in and studying. I could not find any reason to dissapprove of this behaviour, in fact I was enjoying his new found enthasiasm for looking pretty. I also liked the way he was talking more and not just about clothes but about feelings. There was also a closeness that was new to us, even a physical closeness that had started in the first encounters with hugs then by sitting next to me and letting me put a parental arm around him. These were special new developments in our relationship that both of us relished it seemed.
Sean was already a studious boy, but if he dressed he would be confined to the house which meant he would study more, which in turn I felt sure was reflected in the marks that he achieved at school.
I did need to make it clear that our 'hobby' was not universally accepted and he should be descrete about leaving non male items on show as they would raise suspicion in our house, his grandparents did call as well his friends, fortunately never unannouced so we always had time to have a quick tidy up if someone was calling.
During the term up to the summer holidays we fell into an easy routine, both of us slept in nighties, I started wearing knickers fulltime, and come the weekend if Sean or myself was not going out then our femme side got to come out. It was a lovely time where we got to know each other better and our feminine sides flourished. As the weeks went by I also increased his allowance as it felt mean to limit his money to that of a boys when he had female expenditure as well. Soon I was seeing new skirts and tops, and make up that I called experimental but required products I would never buy, and colours I did not know existed.
He had found something that had taken his interest and like many teenage passions it became consuming. He was reading everything he could on the subject especially while dressed, there were hours spent practising and experimenting, I was pleased to see this had no effect on his school work, rather he cut down on his PS time. I used to come home to a lad slouched on the settee or involved with a hand controller intensely watching the screen, then I would come home often to a call from upstairs 'be down in a minute' when I shouted my welcome. Like I say it was a good time for both of us. Some of our conversations were not atypical of father/son relationships. I still remember clearly the first time sexuality came up, he asked me directly if I was gay, I told him I loved his mother and even though she was not about, still did or at least her memory. He however over the weeks revealed he was getting confused over his orientation. Did he like to imitate girls because he wanted to be one and have boyfriends, or did he dress like a girl as a form of worship for the females he knew and fancied, and why did he look at both sexes thinking which of them were good looking. The other hard topic to work with was his dillema of the future, he had seen what hormones did to his friends, the girls long ago developing womanly curves, and some of his lad friends starting to shave, most having got the deeper voice already, and he wanted to know which would be better, to grow facial hair or breasts, and I could see he was torn between the two. There was discussion about getting drugs that would stop his male hormones kicking in and put off the time he had before the testosterone ruined his girlie looks and voice. What could I say he was my son, we, now I, had raised him as a son but I loved having a daughter around, I found his questions just as challenging maybe because I never had the choice really but had dreamt of the situation, and now I had to find some answers to help my child.
After school broke up and he relaxed into the holidays, he made some changes that I was not entirely sure about. For the past few years he had spent time with his grandparents doing jobs for them about their houses, gardening, heavy cleaning, painting sort of work. They liked having him about, he liked going and he liked the money they paid him. In years past he would spend the money on games and going out with his mates, this year he still went out with mates but he also went off on his own feeding his new hobby. His first purchase was a lovely ankle length sun dress, fading from chocolate brown at the metres long hem to pale cream on the shoe lace shoulder straps. I had seen it on one of our shopping trips and knew it not to be cheap so was unsettled that he was spending so much of his limited income on one item. He did look good in it though. The next surprise was far more significant, I came home one day to find him making us tea fully dressed, which was not that unusual except he was not wearing his wig. He had been to a salon and had his own hair styled, it was now blonde, the sides were tongue iron straight with the top being a randomly spiky quiff with plenty of hieght, a style I had seen on a few women and one male. He sensed I was clearly shocked and asked if I liked it, 'Will take some getting used too' I offered. It was then I noticed two small studs in his ears, 'You seen your gran yet?' she was very distinct about gender roles I always felt, but he said he had been round earlier and she had said nothing, just remarked that he had tried something new. It certainly was new. The following morning in a nightie and flattened bed hair it still looked dramatic, and even when I saw him that evening in his lad clothes as he went out with mates, the blonde quiff still struck me as feminine even with a hoodie and jeans below it. He knew that his mates might well tease him because he mentioned it before he left, and he was right. I was still up when he came in and he wanted to talk I could tell. He had been teased, his hair had been called 'gay', some had tried to flatten it but the gel held it too well he said, it was not all negative though some had liked it especially the girls that hung out with them, which unfortunately did not help diminish the gay tag at all.
What was surprising was the reaction of his grandparents,especially the grans who said nice things about his new style, Kay's mother even saying he reminded her of Kay, which I kind of got at the time, but really got the next time I saw him with make up on, simply stunning. Yes, just like his mum I thought.
A big turning point for both of us was when we went away for a week to a caravan a friend let out. The caravan was only part of the big event, the start was a conversation a week before. We were sat in on a Friday evening, Sean in his long sun dress, me in a plain blouse and floral skirt. He had been home all day doing nothing much so had had time to think, 'Have you ever been out?' he asked I thought I had told him about my night walk a long time ago, but I told him the tale again. 'Do you never want to go out as you are sometimes, we get all dressed up and never do anything, just sit around here' he was asking what I had long ago decided I never had the nerve for, going out en femme. I prevaricated with the dangers of being caught, not looking good enough, wanting to pass, not wanting to arouse comment, getting teased, seeing someone I knew. He came back at me with the words I had complimented him with, that he looked great and that he was so feminine, his argument was that if he was that good and he also considered me to be very passable, then why don't we go out as girls sometime and see if we can do it. I remembered how terrifying and how much of a buzz my night walk had been, but Sean was not thinking about dark lanes I sensed he was thinking of daylight in a busy place. I was apprehensive of his ideas to say the least.
By the time we were packing to go away he had it all worked out, he had done research and found that Blackpool, which was not far from where we were going had plenty of gay and trannie friendly places, so he was packing with trips to those places in mind. But it was the Saturday morning as we packed the car that I got a full sense of what he planned. With it being the weekend we had breakfast in our female style wraps before getting dressed. While I put on jeans and a cool shirt, he appeared in a new outfit of pale blue top and what looked like white track bottoms but were not, they fitted rather too well and had ribbon ties at the ankles and hips, his feet had delicate white sandals on them, off course his hair had the big quiff looking very dramatic to finish the look off. After I gathered myself together, I asked 'new clothes' to which he replied 'yes, do you like them?' 'Not your normal' was all I managed. 'What is my normal?' was his reply. I had to agree I was not sure what his normal was by then.
We arrived at the caravan site and booked us in at the gate where I got my first indicator of where this week was heading, the man on the gate passing the pleasantry that he hoped me and my daughter would have a nice holiday, I nearly corrected him but thought that this is what Sean wanted to try and do, he wanted to be my daughter even if I was not sure about going out as his mother. He clearly heard the comment and once inside and unpacked added to his look by doing his face, then sitting down and painting his nails a strong pink colour. 'So what do I call you, Sean will sound odd if I need to use a name?'
'You were going to call me Tamsin if I was born a girl, and I like it as well, so Tamsin or Tammy would be nice'
'Ok Tamsin, you have thought about this far more than I have, anything else you should tell me?'
'Well besides not having anything I would consider boyish to wear you mean.'
'What?' I was struggling to get my thoughts together 'what if........'
'I hoped you might like the idea of having Tamsin around for a week' he was looking nervous and hurt.
'Oh well yes it will be nice to have Tammy about, it is just if anything goes wrong and we have to explain why my daughter is really a boy. That sort of thing'
'Sorry, did not think about that, maybe I could borrow something of yours in an emergency'
'I suppose you could, just a bit of a shock to the system this having a daughter around'
We spent the remainder of the day looking round the local area before getting some food and settling down for the evening and making plans, or rather I listened while Tammy told me about all the places my daughter would like to go and explore over the next week.
To be fair we did have an excellent week together, not many parents get to spend time with their sixteen year old children so I made the most of it. Sean/Tamsin did also, the track bottoms were fine for around the site, but for going out he always wore a skirt or dress with low heels or flats in the day, heels at night. We started off going to some resturaunts that were on his list and from the clientele clearly a lad in skirt was nothing to raise an eyebrow at. But we progressed as confidence grew to going anywhere we fancied, walks around local towns, rides on the pleasure beach. By Wednesday he was taking me into shops so he could show me clothes he fancied, and hoped I might buy for him. And by Friday he had persuaded me to return to one of the nice places we had eaten in I was not going to leave the caravan in my dress though and came up with a very complicated plan for getting partially ready, then driving to a secluded spot and finishing off my tranformation, Sean particularly good at make up by then enjoyed doing my face for me which I always felt was a weakness in my disguise, but with his expert skills I felt far more comfortable as we left the car for the short walk to the pasta bar. The owner even remembered Tamsin and commented how nice her parent was looking that evening, I blushed so much my face burnt, he had read me, but seeing my distress he calmed me by saying how he often got customers check out the place first before returning again in their special outfits. He gave us both a mediterraean kiss before showing us to a table. I was so nervous by the time we sat I drank a full glass of water just for something to do, I then realised Sean was very calm and I was a wreck, this should be the other way round I thought and accepted that if I was read in this place then it was not a problem, people half excepted to see cross dressers anyway so they would be looking. This made me feel better and Sean helped with reassuring words as well.
Like I said this week away was a big moment in both our lives, I had been out en femme for the first time really and Sean had not only been out but had lived as a girl for a week. Thankfully once we got home Sean toned down the girl style to nearly where it had been before.
It could be said that what went through the washing basket would be a good indicator of the influence cross dressing was having on our lives. At first we were putting nighties then knickers through the wash, Sean was putting more of his skirts in though because he wore them more often than I did, but what was interesting was the subtle changes, I say knickers but that could be broken down into plain cotton right through to satin, silk and lace materials, and styles including thong, french, boy cut etc. I tended to stay with plain styles but in nice fabrics, Sean was trying out different styles, he said to see what was comfortable and felt good. When we got back from the caravan I noticed that he was wearing more thongs than ever before and no socks, which was down to the deck shoes he had bought while away that he wore bare footed.
The week had been a peak but niether of us really came down to where we had been, Sean continued to wear his hair up and now had some fairly asexual clothes like jeans which were rather tight and fine knit tops that we both knew came from the girls section but could easily have been in the mens. He also spent more time with girls in the area, of an evening he would hang out with three girls who lived close by and loosely meet up with the wider group of teenagers, but for a few weeks these girls were his best friends and somehow inflienced his mannerisms. This was most noticable when I took him to the registration at college for the next stage in his education, he was in what I might call proper Sean clothing but he was walking and sitting as if he was wearing heels and a skirt, I swear he even went to tuck a non existent skirt under himself as he sat down. But then at another time I noticed myself sitting with my hands gently resting in my lap with my ankles crossed under the chair. For anyone really studying us I think we would have given off enough signs to have been rumbled. Sean got on the courses he wanted mostly art and design modules with english literature as the sensible extra.
I was just coming to terms with how his discovery of my hobby had now taken over his personality when he asks if he could make an appiontment with the doctor, for what was a simple request, but the answer was not simple. He had been doing research and found a puberty stopping drug that he wanted the doctor to perscribe, he even had his reasons worked out for the expected questions in the surgery. He would say he was troubled that he was transgendered and stalling puberty would give him time to think before his body became more defined as male. I could see objecting would be wrong so we went together but I waited outside in the waiting room while he went in alone. He came out with a smile on his face but the doctor asked me to go in for a minute. Sean was sixteen so he was in a transition period as far as doctors were concerned, he did not have to get my consent but it was better if he did. Sean had convinced this man of his problem and felt 12 months would give enough time to sort himself out, but he would have to see a counseller during that year and be assessed. I was asked if I was aware of Sean's situation and said that I was, then asked if I had any problem with Sean being possibly transgendered, I said not in a less than convincing way, I liked Sean and was not sure what having a daughter all the time would be like, for the mean time Sean would basically be an undeveloped boy amongst his developing peers which would be odd in itself.
I was glad the drugs were not bought of the internet but I was still nervous everytime I saw the bottle and wondered what they might be doing to him. More noticable was what he was doing to himself. Without the restriction of a school dress code he slowly changed his everyday appearance, by the christmas break his baggy jeans and sweat tops had gone, fitted jeans and tops were everyday now, he wore thongs now because he wanted to avoid any unsightly pantie lines and would eat sensibly so as not to put on wieght. Our bathroom was now a problem if anyone visited, lady razors, Immac, scented bath oils and sillk dressing gowns would look very odd in a two man household. But Sean was also pushing his boundaries with his make up. He started with a single coat of mascara before christmas, but by easter his friends he said had encouraged him to be more adventurous. Clearly these friends were not the ones who had said his blonde quiff looked gay. Come easter I saw him go out of the house in trousers and a warm jacket that could be Sean's but his face had bold mascaraed lashes, a hint of colour on his lips and I felt sure some blusher highlighting his cheeks. Add to that two pretty stones in his ears and now with a longer hair style I was unsure whether to call him Sean or Tamsin. I even told him to be careful as he minced out of the front door, something I had never said before.
Well easter maybe was not a big moment for Sean but it was for me. His grandparents had been making comments about his changing style and seemed to be happy that he was 'finding himself' and expressing himself as an individual, very liberal I said but was surprised as I had expected a more conservative attitude. But it was the comment from my father questioning whether my son was turning into a girl that was most disconcerting, I suggested that I had had the same sort of thoughts, but felt it best to let him find out for himself, no point in challenging him, he might rebel, and we were getting on really well at the time so why rock the boat? Then there was the time I came home from work to find no one downstairs but could hear voices upstairs and when I shouted my hello, Sean appeared with a very pretty girl just behind him, a little off gaurd I was polite to them as they said hello and Sean apologised for not preparing the tea. I had come home to find Sean entertaining friends in the front room before, but in his bedroom was a concern.
When Sally had gone and I had got myself together and worked out what to do. I broached the subject over our meal. I started by making the mistake of assuming they were in the bedroom for sex and was telling him to be sure and use precautions, but I was speechless when he worked out what I was on about and told me to stop worrying Sally had been using his make up. I was stunned. This girl would doubtless have seen his more feminine clothes, clearly his varied selection of cosmetics, and if she had used the bathroom my things also! He told me Sally was 'cool' with his dressing, found it exciting he said, she had been using his blusher and tweezing some of his eyebrow hairs. And checking out his wardrobe? I asked, no he reassured, but you did not hide everything I guessed, no he had not tidied up for her. I could only imagine what she would make of pink baby doll nightwear and the heels he usually left out. I excused myself and went to the toilet as an excuse for taking a peek in his room, and yes the heels were out, not the nightie, but the make up was all out and looking very much a girls room.
By the time I had rejoined him I was settled again, asked him about her and was thankful she seemed to be a good friend from college, the emphasis on friend being clear. Then he asked if I could let him have some money to get his hair done, he had been dying it blonde himself but Sally wanted him to go to a salon she knew and get a new style now it was longer. When I asked where? he said in town somewhere called Wannabes.
Two days later I came home to find my child looking different again, gone the spiky quiff, now he had what looked like all his hair brushed forward around his face feathering to a soft edge, and the strong blonde was gone, replaced with ash colouring and darker tips on the feathers. It suited him and I told him so, inwardly thinking he was looking real pretty if I was honest. He chatted easily about his visit and the nerves he felt about changing the style, but how Ginger the stylist had put him at ease as she had explained and worked on his hair. Seems she has a few men and boys who go to her for the hair cuts and styling. He even suggested I should go next time I needed a cut. Now that was a step way to far for me, but I was happy with how his had turned out.
If Sean was becoming more relaxed with his feminine looks I felt that maybe I should let go of my male stereotype a little, meaning when I was out of the house. I had been keeping myself clear skinned since the previous summer and had been letting my hair grow, just having the ends trimmed to keep it neat. I was fulltime in panties and nightwear, sometimes wearing a camisole as a vest. I had also been making contact with other cross dressers and exchanging e-mails, some were brief but other contacts flourished into good relationships even if we would never meet due to us living on different continents or neither of us having the nerve to meet up publically. That was until I made contact with Julie, a dresser much like myself, been at it for years, until recently never went out, looked pretty when she made the effort, and lived only a few miles away. We chatted for a few weeks, Julie told me of her visits to a shop that caters for trannies and what she had bought, there was also the visits to Manchester and it's famous gay village where she had gone to the Concord and then openly gone to bars in her heels and dress. I had always know about Canal St but lacked the courage to go just in case I was seen, or worse liked it and wanted to go again.
That was February, by March we had meet up as men for a face to face because you hear of people pretending to be someone else, wierd isn't it. We got on alright, Julie was not as slim as me, but had a more mature figure that could easily be mistaken for a woman's. We e-mailed some more, Julie went into the gay area twice more and was pressuring me to go as well. I did not know what to do and it slipped out when I was chatting with Sean one evening that Julie wanted me to join her in town, I knew he would encourage me, and he did. That evening I e-mailed Julie with Sean looking over my shoulder, and without much delay had a reply inviting me to visit her at home or go into town. Sean wanted me to go into town, but I settled for the safer visit to Julie's home that Saturday.
I was a bag of nerves all morning, not able to decide what to take, how much to prepare before I left (there was no way I was going through our door as Stephanie). Eventually I left Sean about four to make the short drive to Julie's. She came to the door already dressed in a plain grey dress, big heels and a bob cut wig. I got a full on hug greeting and told to go upstairs and use the spare bedroom. A short while later she came to check up on me, I was in my underwear with a short silk wrap covering the top half and applying my make up. I was still very tense so the glass of wine and friendly chat helped to ease me down a few notches on the stress scale. I had taken a chioce of outfits, a plain white blouse and blue skirt for if Julie was being conservative, and a light blue dress that barely covered my stockings and fastened up the back with a series of buttons I usually asked Sean to finish off after I had done all I could reach, this time I asked Julie who willingly fastened those hard to reach buttons, then after I had attached my jewelry and dabbed some scent on me, took a long look in her massive mirror. I felt great stood there posing with Julie beside me looking excellent too. I turned and hugged her, this was a big moment for me, I had never dressed in front of a stranger before and Julie was making it so easy.
She had made us a salad to eat, which by seven was gone as well as the bottle of wine. Sitting in her living room, listening to and chatting away about our likes, dislikes, past and possible futures, she suddenly tells me we are wasted in her house, we should go into town and let her show me around. I initially said no, but as we cleared the pots away she complimented me so much on my looks, my bum wiggle, my sexiness. Flattered I did not put up more than token resistance when she got my coat and told me we were going in her car.
The rush of cold air on my stockinged legs and bare thighs was a bit sharp and cut through the nerves that I had about going out of the front door. I made it to the car and after a few miles relaxed. That was until Julie parked on a side street and I worried about how silly I would look, Julie almost dragged me out of the passenger door, then walked with linked arms, like I saw women often do into Paddy Goose, a dump of a bar but Julie said was always a good place to start. It was just gone eight and there were plenty of men in there, and a couple of trannies sat in a corner, they smiled at us and we got ourselves a drink. Found some seats and Julie told me about her last visit when a bloke had chatted her up, I said no thank you to anything like that. Then I heard 'Hi this is Mandy and I am Crystal, you new round here?' Julie explained how she had been a few tiimes but I was a virgin, they squealed in delight and offered to look after us.
They took us to the Union, then onto Mantos and Churchills before finishing in Napoloens. I was not fit to drive by the time we were thinking of going home, I had danced with all three of my new friends plus two men, I had felt a hand stroke my arse more than once and been kissed by Crystal, and not a gentle friends kiss, full on passionate kiss that I did not know how to handle, besides it being years since I had kissed anyone properly, this was a man in a dress like me and his tongue had licked my lips teasing them apart. It did not last long and she apologised after saying I was too f***ing sexy for my own good. Julie reckoned she had not drunk enough to be illegal so about two in the morning we made our way carefully down the emptyish Manchester streets to my house. She obviously wanted to know how I felt about my first night out and recounted all the good parts and some of the less tasteful ones, like having my arse groped. She was interested in the bit about Crystal kissing me because Mandy and her had had a private moment, and though she did not fully explain I am sure one of them got to taste the others semen. I should not have been shocked, from her e-mails I should have guessed she was open for sexual experiences and was pleased that she had never come on strong to me. Arriving at our house, I invited her in for a coffee. We were chatting some more when Sean comes downstairs in his baby blue long satin nightie, with the pretense of getting some water. Julie said 'Hi' so I introduced Sean 'This is Tamsin, did you have a good evening dear?'
'Yes thanks, just getting some water, nice to meet you Julie' he replied
'What a lovely child, very pretty. Just like her mother'
I said she was pretty like her mother before I realised Julie was refering to me as the mother, what a disturbing compliment though it was meant in good part.
By something past three, the house was quiet, Julie gone and I was cleaned up and ready for bed, as I tried to calm down and find sleep I went over the night once more considering what things I might wish to avoid and what I might plan on exploring as Stephanie some more.
Those plans were quick to be organised, by the end of Sunday I had e-mailed Julie and set up my next Stephanie outing. Basically the same as the first time, start at Julie's, change, go out, see what develops. Julie also went out mid week to the trannie club called Concord and told me what a good night it had been. For my part in this new relationship I did my best to be as well prepared as possible, by Thursday I was well and truly clean shaven below the neck, my eyebrows had thinned a little and my skin was being miosturised on a daily basis in the hope it made a difference.
By the time I walked into Julie's house that Saturday I was well psyched up for my first planned night out as Stephanie. I had my blue dress because I had been complimented on it the week before, I had some killer heels to match it, I had cleaned and revived my long blond wig and was ready to strut my stuff, as they say, down the streets of Manchester. Julie greeted me at the door in a short wrap barely covering her lacy black underwear, we hugged and I went to get ready. An hour later we are eating penne pasta and drinking red wine, me in my blue dress, Julie in a sheer black blouse and leopard print mini skirt with the nicest boots I have ever seen on anyone, on her feet. Eventually I summoned up the courage to say I thought she looked a little slutty, maybe looking for sex I ventured. 'Brilliant' was the response, exactly the look wanted. It transpires Mandy would be going to Canal St as well and it would seem Julie had planned something more than sticking with me, and showing me around for her night on the town. Thankfully Crystal was not going so I would not have to work out if being intimate with trannies was for me that evening anyway.
The evening was better fun than I expected after I heard about Mandy's presence. We drifted around a few bars, had a few drinks, got chatting with other trannies, they are quite easy to spot when you know what you are looking for, got chatted up by a couple of trouser wearing blokes and had a few dances later on with the same men. I was amazed at how much I was enjoying myself even without Julie metaphoirically holding my hand as it were. She was actually missing for quite a while once she had seen I was busy chatting with some new friends. The evening ended with us getting a taxi back home, dropping Julie first then me. Like the week before except I would still need to go and pick up my car sometime, but the taxi was safer if very public I felt, which was part of what going out with Julie was all about.
After the easter break revelation that I could venture out in a dress and survive, I was more or less out with Julie every weekend, even going to the Wednesday night club a couple of times, but that was hard with work the day after. I made lots of new friends mostly trannies but a few real men who seemed to like their women to be unconventional. There was one called Pete whose company I enjoyed and he seemed to make a point of being around when I was on my own, he never came on strong like many men did, he just enjoyed chatting and complimenting me on whatever I was wearing. After six weeks I had quite a contact list and was prepared to go without Julie if need be. I also for some drunken reason had given Pete my e mail address and our conversations continued mid week which for me kept the anticipation of the weekend fresher in my mind.
During this time from easter to summer, I was getting far more involved in Stephanie than ever before, I was buying new outfits and preening myself in the evening for no reason other than I could. I was trying to keep an eye on Sean but on reflection I was possibly preoccupied. I had noticed a check shirt/blouse he was wearing to college had a nice pink cast to it and clearly had buttons on the wrong (or right) side, depending how you looked at it. He had white linen trousers he wore with white canvas shoes and he had taken to wearing silver rings and bracelets as well. Sally seemed to be around a lot more than ever before, but was constantly reassured that she was just a friend, not a 'girlfriend' in the normal way. But I was going out early on a Saturday and getting home late, so Sean had a lot of leeway then to do whatever he wanted, if get what I mean.
It was early June I discovered just how much leeway I had allowed when I came home unexpectedly about eleven on a Saturday night. In the front room were four teenagers, Sally and Sean or should I say Tamsin, with two boys. They were drinking cheap lager and when I came in they were behaving like boy/girl couples, Sally and her boy on a single chair, Tamsin and another boy on the settee. I don't know who was more shocked, me or them. I was in a thankfully respectable long cotton sundress but it was still a dress, and the room was full of adolesent hormomes. Tamsin's boy almost jumped off the settee and Sally actually got up and apologised 'Sorry Mrs Bates we were doing nothing just mucking about' It took a moment for my entrance to have destroyed their fun and for them to have made their excuses to 'Mrs Bates' and leave.
I made myself a drink and tidied up the beer cans while I considered what I should do. I took a longer look at my son, he was wearing a loose top that revealed his bra straps, his mini skirt was pretty but very short and his heels were simply sexy, that added to his pretty made up face meant he was looking very much like a girl really.
'Does your friend know what you really are?' I started
'Oh John you mean, yes he is doing a modern art module with me'
'And Sally's friend?'
'He should do, he is John's best mate'
'you do realise what signals you are sending out to lads with the clothes you are wearing'
'Yes I do, and John is alright, he is cool with all this, likes it when I dress up actually' there was then a pause 'but can I say the same of you', it was then I looked down and saw my very strappy skyscraper spikes showing below the hem of the cerise dress. I nearly said 'but I am not snogging lads' then remembered how I had given Pete a deliberately passoinate kiss before we had parted that evening.
We ended the evening sat together apoligising for the way we had reacted to each other and rather unexpectedly discussing what it is like to kiss a man as opposed to a woman. Both agreeing it is nice to have a man want us and make that clear in the way they behave by allowing him to take the lead. Just before midnight as we were going to bed I asked if he had tried girls, he said yes he and Sally had 'practised' kissing but it was odd kissing your best friend, I suggested there might be other girls out there besides Sally but for the moment he was rather hooked on John.
This event triggered something in me though, I discussed with Julie the differences between men, women and trannies, I had kissed Pete properly and some trannies in a friendly way, so Julie suggested we set up some dates, where we try going out as a straight looking couple. To start with the next Friday' Cluade (Julie's male name) would escort Stephanie out for the evening. Still unable to walk out of my own front door dressed I changed at Julie's. This time the door was on the latch and I let myself in, I went to my usual room and dressed in a nice white shift dress, bare tanned legs and white sandals. I came downstairs to find Claude in a smart suit and ready to take me out. We had a lovely meal, I linked his arm as we walked, he paid for everything and made me feel like a woman, in the way I had done when I was trying to impress Kay all those years back. Then back to his house for a nightcap and what turned out to be some intimate experimenting. Claude played his male part and at times forced himself on me, but when I resisted he would tell me to relax and enjoy being the centre of his attention. Before the night was over I had lost my dress and dressed only in my underwear had played for the first time with a cock that was not my own, even succombing to the excitement of the situation and kissing it, then accepting it into my mouth where he ejaculated before collapsing on the chair he was sat on the edge off.
I was unsure about how I felt about the whole experience, but all too soon it was Saturday and my turn to repay. I dressed smart/casual and called round to pick up Julie for our date. She was lovely in a chocolate coloured wrap dress, she had kissed me as a greeting but not in the way Stephanie was kissed. I took her to the pictures and for a drink, then took her home all the time trying to treat her like the woman she appeared to be. I did try to be a dominant male, but was not very good at it, in the end Julie in a reversal of our previous night activities lost her dress, which was not that hard only having two ties holding it fastened, then set about me like a sex starved woman, kissing my dick and then using the erection to rub against her arse, eventually she knelt over me and sucked me until I came, then instead of me collapsing in a spent heap, I said 'sorry' and offered to wipe her face clean.
During the next week we came to the conculsion that I was not a stereotypical man who only thinks of sex, I was more caring and thoughtful, but when I was asked the question 'which did I enjoy most. Being the man and coming. Or being the person who made the man come' I took two days to answer but in the end said I felt more at ease being Claude's compliant woman than trying to be an assertive man to Julie.
I was glad I had never left the house in one of my dresses because on day early in July a nosy neighbour got chatting as I was clearing weeds in the front garden. She was telling me how she had seen Sean, well at least she felt sure it was Sean, going about with a group of teenagers and unless she looked hard it was not easy to say Sean was a boy unless she took a good look. I told her it was a phase he was going through, maybe the art students he was going about with were influencing him. Well I could hardly say 'Keep your nose out you nasty old witch, what does it matter to you that we both like to wear women's clothes.' I did bring the topic up with Sean though, I told him about the old witches comments, he seemed amused by it, but I tried to explain how people like her start whispering gossip all over the place and soon you feel everyone is looking at you and making up stories behind your back. His grandparents on the other hand seemed to have accepted his ambiguous gender style, maybe there would the occasional teasing but nothing spiteful, just the way they always had treated him from being a baby.
Maybe it was paranoia but I was feeling like we were being watched even more, or maybe I felt it was time to move away from the memories of Kay. Whatever I put the house on the market, sold it and moved out of town, close enough for Sean's college and my work, but far enough to aviod gossip and get a more private location alllowing us to come a go without curtian twitching in the windows opposite. I also stopped refering to Sean as son, just child, so our new neighbours could make their own minds up probably able to find out from other teenagers about him if they so desired. One big change for me was to have more courage to dress at home, I could even leave dressed if I put my wig on once away from the house due to the concealed position of the house.
The privacy and distance that his friends had to cover to visit threw up new situations of their own for Sean. Of a weekday he was looking fairly camp and gay with his tight jeans, canvas shoes, and pastel coloured tops, but come the weekend unless we were going somewhere and I asked him to tone it down, he was Tamsin, make up, skirts, heels. I was fine with this even before we moved, but once we moved he stopped dressing down if his friends were visiting. Sally was the first I knew to come and be welcomed by Tamsin, but it was not long before John called on a Saturday and Tamsin was the person who opened the door to him. I even had a little bet with myself as to how long before he went out with his friends as Tamsin, walking out the front door in his heels. I was not far off, he went to a christmas party with Sally, not in full female mode, but enough make up on you not recognise he was a boy under the cosmetics and clothes.
Around about this time his sessions with a counsellor finished along with the drugs, his vioce had not broken and he still did not shave, the counsellor had delved into his past looking at childhood influences, losing his mother, and eventually my part in opening him up to wanting to be pretty. They talked about sexuality and his likes and dislikes, but I could also see he was experimenting to see what he preferred. I found it helpful myself to chat with him after his sessions as it allowed me to think through some of the issues I was having within myself, maybe even work out who I really wanted to be.
I was still friends with Julie, but I had a wider circle now which included real men like Pete, and after my dates with Claude and Julie found myself looking for oppurtunities to be the female partner in a relationship, no matter how brief. Sometimes it was just a dance and a groping kiss, other times like with Pete it could be a nice evening with some serious petting at the end. That was until Sean made arrangements to spend a Saturday night out, sleeping at Julie's and coming back Sunday. I told him to be careful, not to get drunk and look after himself. I hoped he would heed my advice but he left wearing leggings and a long pink top with goodness knows what in the pack he was carrying. As it turned out it should have been Sean/Tammy giving me the talk. With Tamsin gone I ran a scented bath and removed my silk trousers and soft cotton blouse. I had rung Pete to invite him over for a meal that evening as I had the house to myself and this was the start of my preparations. I did the food prep in just my satin wrap, then prepped myself for his arrival. I wore my silver tube dress which worked well if I used adhesive on the false breasts, the long blonde wig was securely fastened which more than could be said for my white sandals that only had a toe strap and felt very loose under my heel but looked fantastic. Pete turned up at eight with flowers and wine, we ate my food, drank his wine and enjoyed some close intimacy as we did so. I fully expected him to leave after I had satisfied his carnal desires, which up until then had been me kissing his dick and catching his semen in my mouth. But that night I took his load washed it down with some wine fully expecting him to leave shortly after, how wrong was I. First he had drunk to much to drive and second he was still randy and wanting more. Realising he would be stopping the night we drank some more and got quite silly, which lead to us going upstairs giggling like kids, I offered him Sean's bed but instead he pushed me against a wall and kissed me. It took seconds for him to pull my dress up above my hips and then guide me onto my own bed. I was so relaxed and enjoying the attention that I hardly noticed when he removed his trousers, I did notice when his prick rubbed between my arse cheeks loving the way he was making me feel like his woman, the cold of the gel he then massaged into my arse soon warmed up, then he was back to rubbing his dick into my arse. I remember flinching when his cock pushed inside me, but his mouth was over mine so I could not moan, only tense up. Then he started to rhythmically move in and out, every time going a liitle deeper, and all I could think of was that I was being made love too, and wasn't it lovely to there. I don't think I had an orgasm, reckon I would remember something like that, but he must have come inside me because when I woke in the morning, I was wearing my powder blue silk nightie with him lay beside me and dried spunk between my legs. I am not sure I remember all the details, but I knew enough to know that had been the night Stephanie lost her virginity properly, even if alcohol had denied me a clear memory of the facts.
Tamsin came home around lunch time, Pete was long gone and the house was tidy, I was still on a high and wearing a pretty flowered dress. Tamsin noticed the flowers and picked up on my mood instantly.
'You had a good night while I was away'
'Not bad, how was yours?'
'He brought you flowers' I did not pick up on the he straight away
'Yes, nice lilies aren't they' I replied
'He made you happy I see'
I thought back over the previous evening 'yes he did'
Tamsin was giving me a knowing look, so for some reason I said 'and before you ask young lady, he behaved like a perfect gentleman'
Tammy's reply was 'and you behaved like a perfect lady I expect' which was said with a smile. 'Oh mummy, I am so pleased for you, was it good?' she stepped over to me and hugged me.
'Whatever do you mean?'
'Was he good, did he make you feel loved?'
I evaded that with silence.
'He did didn't he, did your boyfriend became your lover?'
'Stop it Tamsin. You are embarrassing me now. How was your night at Sally's?'
'Not as much fun as yours, we went round to a girls called Alice, played some silly games, paired off, did some snogging, went back to Sally's, stayed up till four chatting. You see very dull by comparison.'
Trying to keep the focus away from me 'The snogging........ with a boy or a girl?'
'A boy off course, girls are just too soft, some boys are really good kissers, but you know that don't you?' it was back to me, so I changed the subject and asked if there was any college work to be done, as for me I needed to get some more cleaning done, not that I said it but a stained nightie and a make up smeared pillow needed attention.
Christmas that year was a mix of Sean/Tamsin, Stephanie/me depending on who we were seeing, relatives was a male inspired look, anyone else could be quite feminine. We bought each other presents, I bought Tamsin a nice bottle of perfume, Tamsin bought me some jewelery nothing to expensive but included were a set of ear rings which would require me to have my ears pierced if I was to wear them. Initially I said no way but on the day after boxing day we were sharing a bottle of vodka and I found myself having my lobes wiped in antiseptic then numbed with an ice block from my drink, ending up with the small gold studs being fixed to my earlobes, even thanking Tammy for doing it.
I had a holiday between the christmas break and new year, so from December 28 until Jan 3, fuelled by the vodka we pledged to be mother and daughter for 5 days. Julie came over, stopping the night and called me Mrs Bates once more, seemingly unphased seeing two men dressed in satin as we ate breakfast. An interesting development was Pete meeting John. John had come over after lunch and had spent the afternoon chatting with Tamsin who was in skirt and heels, making no attempt to look like Sean as we had agreed. He had seen me before as Tamsin's mother but this time was less awkward. I was in a warm top, trousers and heels when he arrived, the conversation was stilted but he seemed a nice boy and I left them to it as I pampered myself in anticipation of a date with Pete. My man turned up about seven and I still was not ready, I had my red underwear on, and had picked out the red silk blouse and leather skirt but my face was still under construction. Tamsin played host very well, offering him a drink and chatting sociably with him. Eventually I came downstairs to find Pete and John discussing the latest signing the manager at City had made after the discovery that they were both season ticket holders and not far from each other in the same stand, before Pete finally escorted me to his car he and John had made arrangements to meet up at Eastlands in two days time when they played Spurs. By comparison the rest of the evening was uneventful, nice meal, nice chat, nice cuddle in his car, nice blow job for Pete. Nothing I would not consider extraordinary at that time.
Following the match Pete had arranged to come over as it was an afternoon kick off, but he turned up with John and they had clearly had a good day, we did not have to wait long to find out City had won and they were in celebratory mood. Tamsin was looking lovely in a lime green tunic and leggings, I was more mature in loose trousers and a long cardigan, but this did not stop Pete making it clear he still fancied me, and in front of the 'kids'. I made some food for all of us, Pete hardly able to keep his hands off me as he drank more beer. Tamsin and John descretely disappeared into another room leaving us to it, well Pete to it anyway. We all regrouped around the dining table eating and drinking. Topics covered football, work, college, weather and surprising both me and Tammy, could we live as men, give up our skirts. The men thought we could not and did not want us too, and after some debate, Tamsin agreed with them, even saying it would be impossible to be a fulltime, I was more resistant but agreed after Tammy told everyone that no one in the house wore anything but knickers in the daytime and nighties to bed, even on a normal male day. I was sunk acknowledging that I had no male underwear. So then we played 'what if' and soon found Tammy saying that if he could live as a girl he would. John saying if he could, he would marry him. Pete asked what if I could live fulltime, and I said foolishly said yes.
By midnight it was clear Pete could not drive so I invited him to stop, and when Tamsin quietly asked John if he would like to stay as well I did not object like a normal parent might have done. I can only think I had drunk more than I realised and when we made some sort of noises about who should sleep where I slyly slipped Pete into my bedroom, well it does have a double bed. AfterI changed for bed, I bumped into John on the landing when I went to the toilet, he was looking flustered and through Tammy's door I caught a glimpse of the long satin nightie. I too was in a satin nightie so leaned towards him, gave him a peck on the check 'I think you will regret it if you sleep on the couch' and he blushed. I did my business and returned to find Pete in bed and ready for me, and I was ready for him, no way was that night going to be all about his pleasure, I was going to be made to feel like a woman once more.
The next morning I gingerly crept downstairs not wishing to wake anyone, and was surprised to find Tammy in the kitchen, I was walking carefully as Pete had left me sore between the legs after I discovered what an orgasm was. Then I noticed my child moving with care and a big love bite on the neck. 'You enjoyed your night then' Tammy would not look me in the eye 'come here I understand, was it your first time?' I asked.
She came to me and I hugged her 'He is a nice boy, and I can hardly tell you not to have sex when you know I did'
'Oh mummy' that was a new one on me 'I think I am in love, and having him last night was so great. It can't be wrong to feel like this? can it?'
'No dear I don't think it is'
We stood and embraced for what seemed like ages.
'I want to start hormones'
'I thought you would, let's see what the doctors think'
Postscript
Five years later our lives could not be any more different.
Once eighteen Tamsin became fulltime and transitioned completely, John was a good friend but she now lives alone and has a settled job in a publishing house doing clerical work.
Her grandparents were on the whole accepting, a little reluctance from Kay's father who eventually accepted the situation even if he did not understand. A harder acceptance for them was when I moved in with Pete, my own mother said she had seen the softer feminine side in me from being a child. Kay's parents however rather distanced themselves from me, I still wonder if I had taken up with another woman whether they would have felt the same. Possibly not because when I moved into Pete's house it was on the condition that I move in as Stephanie. It took me a while to actually move in fulltime as I did not feel able to keep my job and knew I would alienate some friends and family. In the end Tamsin persauded me by example and we had a ceremonial trip to the recycling bins with all my male clothes, followed by a full make over at a salon including hair, make up, waxing and nails before turning up on Pete's doorstep unable to return to my previous life.
WE both still have uncertainities about who we are and why we have this need to be accepted as female, but on the whole we are happier as mother and daughter than we ever were as father and son.
Good grief, I was thinking out loud as I looked at myself. Cat was by my side telling me I looked good, I was thinking this joke had gone a good bit further and far deeper than I expected.
It was our second year summer break, and 8 of us had rented a house in Blackpool for a fortnight. The idea was to just chill out and have some fun, before going on to summer jobs, home or whatever. A problem arose when we arrived and realised that the house had 4 double rooms, and there were 3 girls and 5 men making the 8. Being well prepared, we had all brought cases of wine or beer, so the first thing we did was to have drink as we brought our bags in, then we discussed the room allocation. Two girls siad they would share, but no two men fancied sharing a bed, and there was only one room with twin beds so we spent ages trying to persaude the men to share beds. Then for what reason I don't know what, I suggested we were all good friends and liberally minded, why don't we share with the opposite sex, this got a reserved nod, non of us had strong relationships, if anything we all tended towards promiscuity as a way of life. The men liked the idea, the girls wanted to select who they had to sleep with. Then Carl noticed that there were only 3 girls so that meant 2 men would be sharing. It was Cat who offered the solution, I become one of them.
There was a good laugh and a few more beers opened, and someone offered me a glass of wine instead of beer. I tried the 'You are joking' line, but over half were in favour of seeing me going over to the other side. I was the smallest, least manly, most delicate, and a few other things that I don't wish to repeat, but no matter how much I squirmed the fun had started and soon everyone wanted to see me as a girl.
Cat, Dawn and Steph took me to one of the bedrooms, first they discussed what I was going to wear and which of them was going to do what. Cat was in charge of hair, Steph clothes, and Dawn make up. I was showered, shaved all over, shampooed, conditioned, then allowed to dry myself, when I asked if anything was necessary they just put me down with 'Off course it is'
My hair was a mop on top of my head that I was always sweeping off my face, so while Cat dried and used her heated tongues on my hair, Dawn was combining their make up kits to create a pretty face on my facial features. When they were done Steph produced my outfit, a bra and knicker set, a sheer pink top, denim mini, footless tights and after some looking a pair of heeled sandals. It was now I said 'Good grief' I surprised myself at realising how feminine I looked, if I could stand on the shoes I would have really convinced myself.
The next stage in the evenings fun was to be presented to the rest of my friends, with a bit of a fanfare, the girls lead me into the main room and introduced me as Maria. They all said welcome and offered me more wine, then left to collect a take away as we were getting hungry. I stayed with the girls and found plates and cutlery, I was allowed to remove my shoes if I promised to walk on my toes and wiggle my bum, 'Like this' I said 'Bit more hips' they suggested and I was mincing around elbows in wrists out and feeling like a fool, but being told I was looking great.
Over the food we now discussed the sleeping arrangements, the result was two cups, one with 4 girls names, one with 4 boys names, and they were picked out randomly. Cat was first and got Pete, Steph got Paul, then it went quiet when the slip with Maria written on it came out, two men left, which would get me? Carl's name came out. He made a big show of taking my hand and getting me sit on his lap, even putting a hand around my waist. The other couples made no great show of affection, that was until later when the various sounds of sex could be heard in the building, all except my room. Carl had played the part downstairs, but once alone he backed off treating me like a man again. I did give him a peck on the cheek and told him it would be his turn tomorrow night with a real girl. And with that lay on either side of the bed and hoped neither of us touched each other.
The morning was a strange one, I had make up smeared about my face and my hair felt odd presumably from the stuff the girls had put on it the night before. I showered but soap did not seem to have a great effect on the redness of my lips or the dark colour around my eyes. I went to see what we had for breakfast and find out if they had something to clean me up properly.
Carl was already being ribbed about how had his night been with Maria, he was blushing and stumbling over his replies which made the game even more fun, but I was in my Mark clothes so the temptation to tease him with a kiss and tell lies about his performance would not be as much fun. But the girls did tease me, about Carl and about why I was in jeans and a sweat top. I clearly dissappionted them, I had thought it was just a one night bit of fun. I guess it was my reaction that made them bait me more, I fidgetted and blushed, they told me how good I had looked and that I had clearly had fun with Carl at least before everyone had gone to bed, so why not continue. I put up my defenses, basically saying no, then went of for a walk in what could be described as a sulk.
I had what turned out to be a nice refreshing walk along the seafront, found a nice bar and enjoyed just looking out at the sea. I thought about my situation in the house and amongst my friends, and considered how I should react if they wanted me to play at being the fourth girl again. I had plenty of time as it was late afternoon when I got back. Everyone else was there and the beer was out already, soon I was drinking wine and having it explained to me that they had discovered one of the gay bars, The Flying Handbag, and that would be our venue for the evening, and that they had already drawn for partners and moved bags about, I was with Paul. He seemed fine with the set up and added to the calls for me to go with the girls and refind Maria.
With a bottle of wine, I spent the next few hours listening more than being involved in their chat about what they should wear, but more startling was their talk about how the men performed, they were far more crude than I expected, until then I had only thought it was men that bragged about their activities. I was so wrong, but did learn an awful lot about how to please a woman. After the chat came the serious work of getting ready, all three had decided on a clubby look, they were in body clinging dresses and high heels, and looked gorgeuos, it was pointed out that I had a manly bump up front so tight clothing was not an option, and so I was dressed in the sheer pink top, with a black bra underneath, and the denim mini, but no leggings, this time they rubbed tanning lotion into my legs, as well as each others so we did not need tights. My nails, all twenty of them were painted pink, and my face was painted in a similiar style to the others, the going out look they called it, I just had it down as making them look great, on me not bad. My hair as well as theirs was restyled into rather fantastic shapes. Cat had two pony tails sprouting from her head that were fluffed out and spiked, Steph who had long hair, coiled it up on to her head leaving tendrils all round her face. Dawn had dyed her hair and now a rich red colour, she added gell to make her hair stand out with loads of extra body. Mine was wrapped in the curling tongues until my head was a mass of random curls except for the fringe which was gelled in place so it swept across my right eye and tucked behind my ear. The hardest part was shoes for me, my feet were a bit bigger than Cat who had the largest, so I had one chioce of heels with an ankle strap that adjusted for the extra length, the other thing I noticed was that my coloured toes looked very noticable poking out of the open end, which for some reason made me feel quite feminine.
The boys had been watching football on the TV and took 5 minutes to get ready, but before he left Paul told me I looked great and then gave me a kiss. I had prepared myself on my walk for the possibility of getting dressed as Maria again, and the chance that I might have to behave like a girl towards whoever I was paired with, but this kiss threw me. Paul returned changed and smelling of after shave, then taking my hand lead me to the kitchen, 'You look better than last night,' he started 'and you know what Maria I think we could have some fun tonight' he kissed my cheek, and I quickly thought, I could be a prude and not let him get near me, or I could just play the part and loose myself in Maria. It took seconds but seemed like minutes before I answered 'ok' and kissed him on the lips. When we parted he said 'Great' and put a hand on my arse and squeezed it, making me jump and swipe for his hand which he caught as we entered the main room, looking like we were holding hands. We were ready to have some fun.
The evening ended up being great fun, a few scary moments such as walking out the house thinking everyone must be staring at me, wobbling on the heels and a stranger taking a double look when I spoke. But mostly I saw myself as Mark having fun dressed up with friends having a laugh, though there was always that contact with Paul, I used his arm to steady myself, we sat together in the bar, when the others did some cuddling or dancing he would suggest we do the same. My position in the group was different as well, I was no longer one of the lads, and would be more in the girl group if there was a split, such as going for a pee, or getting up for a girls dance, I was even invited along when the 3 girls got up to go.
No the big, and new turn came when we got back in the early hours, after a coffee, we all split up into our seperate sleeping arrangements. Steph had made sure I knew more of what to do before going to sleep, cleansing etc, but she also lent me a short nightie. I had not made my mind up whether I would sleep in it, but once I was alone with Paul he gave me a real kiss, 'wow' I thought as I did not pull away, maybe I had drunk more than I thought, then he asked if I was up for new experiences, I replied 'usually' 'in that case, shall we see how this situation works' 'uh?' 'as in, me man, you good looking girl' 'oh, I see' and I put my arms around his neck and pulled myself towards him.
That night was a revelation to me, Paul spotted the nightie and suggested I wear it over my bra and knickers. Once in bed and close I felt his erection pressing on me, and felt my own strengthening in the panties. This was such a turn on. By the time we gave up and slept, I had wanked him off, he had done the same to me, but most unexpected was that I sucked him off. Mainly because it is something I like girls to do to me and was very much feeling in the girl role at the time.
Monday morning rolled around, Paul was awake and looking at me when I woke. 'Did you enjoy last night?' still a bit asleep 'the bar was fun, yes' 'No I mean later' 'Oh as in ............' 'Yes' 'Did you?' 'You are one hot girl you know' 'oh' was all I could manage and made for the toilet.
I had to wait for Cat coming out, still in the nightie she looked me up and down 'Good night?' 'Think so' 'Well Maria we had better get you somethings of your own, we can't have you borrowing our stuff all the time' 'What' I replied 'If you are going to be Maria, then you need some clothes of your own' 'Is that necessary?....I thought it was just a bit of fun' unfortunately Paul came out of the room and joined in 'Fun? definitely, eh Maria' then slide his had around my waist and kissed me. I blushed deeply and went to relieve himself in the toilet.
I entered the kitchen some time later wearing a sweat top and the denim skirt, because no matter how hard I looked my own case seemed to be missing and had to borrow one of Paul's much larger tops and the denim skirt to hide my modesty, which was not really that necessary as the top came well below my hips. As Paul pointed out a particularly hot look, a woman in a loose mans top. This hunting meant that I had missed an interesting and for me important conversation, the other seven had discussed if I should stay as Maria for the duration of the holiday, or be allowed my case back. The vote was unanimous, though Carl, I learnt later was slow to be included. Then at Dawn's suggestion everyone contributed £20 so Maria could get some clothes of her own, this was less enthusiastically welcomed but eventually she got each member to pay up.
As I took in the results of their discussions, I did consider complaining and being angry, but I remembered what conclusion I had come to on my walk the day before, to go with what seemed fun, and the night with Paul had been a rather novel and interesting experience, so I asked just one question 'Do I have any choice?'. There was not a totally committed 'no' from all of them but enough to allow me to shrug and say 'In that case, what do I need?'
Dawn lead me away and told me I would have to start learning how to do my hair and make up myself, but for today she would style my hair and help with make up, Steph was going to lend me a knee length skirt, a cotton blouse and a jacket so I could go to the shops. That thought brought home that this dressing was not going to be just evenings mucking about in bars, but the duller and possibly more scary daytime stuff, like going to shops and really hoping no one took me for a man in drag.
It was a scary day, the three girls escorted me around the cheaper stores, buying tops, skirts, a jacket, 3 pairs of shoes, a selection of underwear, a red nightie and a pile of make up. I had little input into the chioces but trusted them not to pick anything which would make me look ridiculous. Then once back at the house I had a chance to try everything on, and have it critized by the three girls. Essentially what I had was two plainish skirts, three different tops, two going out sparkly tops and a couple of more revealing skirts as well as a pair of shorts I could wear anytime they said.
That evening dressed in a gold vest top and cream layered skirt, stood on top of some 3" heels I was partnered with Pete, who had decided they were going to visit a nearby pub, get some chips and return for a football match that was showing that evening. This order followed pretty much to plan, except only Cat of the girls stayed to watch the football, Dawn and Steph taking Maria into the kitchen to drink some wine and discuss boys. It was felt that Pete was the best, he looked good, respected their feelings and was good in bed. The others were better than Pete at something, but overall though not top scorer he was consistent at most things. I did wonder what the bedroom might hold later with that sort of recommendation. The football ended and a film followed, during which several drifted of to bed, either alone or as couples. Pete had got me to sit beside him and was doing some intimate touching which I responded to positively, then when I said it was a dull film and was going to bed he followed upstairs.
He caught me as we got to the top of the stairs, 'Paul tells me I could be in for an interesting night' 'Did he indeed' 'He said you had fun last night' 'Did he?' there was a pause while I turned to look at Pete and consider what Paul might have said, then stated 'We were experimenting.' 'Well I am up for some experiments as long as they are enjoyable' I then lent over to Pete and kissed him. He responded well and lead him into our room for the night. 'First experiment. How was it?' I asked 'Fine, what is the second?' In no time at all we were side by side on the bed kissing and fondling each other and generally getting ourselves aroused. 'Experiment number 2' I said as my hand went inside Pete's trousers and cupped his erection. 'Fine with that?' 'Yes' came the muffled reply as he brought himself under control. A little more massaging and I considered what to do next, kneeling above him, Pete's trousers became undone and I slid my lips over the erection infront of me. For the first time I felt like it was a truly female role I was playing and had no desire to use the erection in the knickers like a man would. I felt like a she as I bobbed up and down on the shaft, until Pete arched his back and exploded into my mouth. This felt so satisfying to me and I licked the retreating flesh making sure all the taste was gone. We lay alongside each other for a while, then I had to get up to clean my face and get ready for bed, coming back in the red nightie, 'My god, you are so sexy, bet you dont even realise it do you'. Pete pulled me into the bed and kissed some more. I tasted cum three times that night, leaving Pete sore and exhausted, but happy.
Tuesday morning and I needed no votes to persaude me to stay in female character. On reflection as I had lain next to Pete, the prospect of not seeing what else this role had to offer was slipping down the priorities. I wanted to try on a different skirt and top, have a go at doing the hair and make up, and then later see how Matt shaped up in the manhood stakes. Dawn helped with the make up, teaching how the different cosmetics work to create the face you want, then taught her student what the difference detween gel and mousse is and what curling tongues can do to create a style.
Later we 4 girls went down onto the beach and sat about gossipping, eating the food we had picked up on the way there, and enjoying the summer sun. I had a female moment when we were walking along the sea front and noticed the long sundress Cat was wearing and liked the way it swirled around her legs, there was nothing that new in thinking a girl is attractive, what was new was the thought for me, of how would I look in something like that.
Come five o'clock everyone was back at the house and there was no partner ballot that evening, everyone only had one person they had not partnered and I knew mine would be Matt. We had discussed earlier what we fancied doing that evening, the rest of the boys wanted to watch a boxing match on TV, but niether Matt or myself liked the idea, so Matt suggested going to the gay bar again, I felt this was a pretty safe option and dressed for the evening, mini puffball skirt and a lycra crop top, darker eye shadow and deeper lip colour and I was set for her first 'date'.
The walk on the 3" heels was not a fast one, but Matt did not seem to mind and would let me hold his arm for support. Once there and comfortably sat down with a drink, we chatted, clearly Pete had mentioned the experiments and Matt made it obvious from the places he put his hands that he was up for some experimenting. We danced to a few tunes and enjoyed the closeness of some moves. Then as I needed to pee I left him, while he went to get a drink. This would be a first, the ladies on my own, not with the others. After doing my business and a quick check in the mirror to ensure the face was still good, another girl struck up a conversation, at first the deeper than expected vioce did not register with me, 'You look good girl, and that man is divine, where did you catch him?' I was a little off gaurd, men's loos dont do chat like this 'He's a friend' I answered. 'Not seen you in here before, new round here?' then I twigged that this was another cross dresser, 'On holiday and it is my second time in here, good isn't it' the new friend gave me a good up and down look 'There are a few of us over in the corner, come over and say hello, and bring your hunk' Five minutes later me and Matt are chatting with four other TVs and surprisingly Matt was quite relaxed about it. It was getting late when they left to get a taxi back, but not before Cheryl had written a mobile number down for me.
Matt had played the boyfriend part very well, his hands had been all over me, I especially liked it when he stood behind me and put a hand firmly on my arse and squeezed a cheek, thank goodness for two pairs of knickers restraining my reaction. When we got in we went straight to our room for the night and continued the kissing we had started earlier, then as Matt undressed and his appreciation of my attentions stood out in front of him, I fell before him and used my mouth to encourage him further, but he stopped me before he came. 'I would like to suggest I treat you as a woman, lie down, take off your panties and let me see if I can make you happy' He massaged some gel into my hole then slipped a condom over his pole, then took up the passion where we had left off. Soon he was entering a quite tight hole, and telling me to relax, which I was trying very hard too. Eventually he was inside me and starting to ride in and out, going deeper every stroke. Slowly I relaxed and Matt could move easily, then it happened I tensed and let out a sound of delight, 'Good?' 'yes, do it again', so he did until he thought he could last no longer, and I arched my back and panted as I came, clinging onto Matt. Lying beside each other I cuddled up close, 'That was great, where did you learn that?' Matt paused a while before answering 'I once had a friend and we tried out all sorts of stuff as teenagers learning about hormones.' 'Well I am glad you did, that was so fantastic.......I had better get myself ready for bed, see you in a bit'
Wednesday morning was a shock to me, first was how sore my arse now was, and how everyone looked at me when I went into the kitchen to get something to eat. Cat broke the silence, 'Well you lost it then?' 'what' I replied 'your cherry' Cat answered. The blush was noticable but I denied again 'what?' there was a collective tittering, Carl joined in, 'We could hear you, and you are walking very gingerly this morning, which sort of confirms what we suspected' I took a coffee and walked out not wishing to get into such talk so early in the day.
As a distraction I offered to go with Dawn to pick up some groceries for the day, in just a plain skirt and top I felt girlie but dull. I mentioned this to Dawn who commented how some girls like to be ultra feminine while at the other end of the spectrum are the almost boy looking t shirt and jeans girls, and it did not depend on how pretty the girl was rather how the girl felt that made the difference. I expressed the idea that maybe as a girl I was more to the feminine end of the spectrum, Dawn remembered how the long sundress had been commented on the day before and suggested they go and buy her something long and flowing. Two hours later they arrived back with the food and a dress that had a full bodice and from below the bust line had acres of soft material flowing down to an uneven hemline somewhere near the floor. I loved the feel of it, but more importantly I had chosen it, it was mine and defined something of the girl in me, not what others thought the girl might be.
Over lunch there was talk about bedroom arrangements now everyone had shared with everyone else. A couple did not want to do the random again, maybe they had had a bad night with someone and wished to aviod a snorer, who knows. This discussion lead to a complicated system where everyone put down their prefered partner as well as their second and third, then Pete would go away and work out if he could get everyone with their first or second chioces. No one knowing if they had been first chioce or not. I put down Matt as first chioce, and Paul as second, Pete as third. Then went of to read a book I had brought to read.
Dawn and me cooked a big stew for the evening and as everyone sat down, Pete produced his results. I had got Paul who came and sat beside me. He was obviously up for a good night as he took me for a walk along the beach later, then a drink, followed by a long session in bed. I was thankful I had been prepared and had bought gel and condoms during the shopping trip. Maybe because Paul was not the first, or he was still unsure of how to make love to a woman who did not have a conventional pussy, but it did not have the fireworks of the night before. It was good and reconfirmed that I liked being the woman, but Matt was still the best.
Next day I had a call from Cheryl, inviting her to meet for lunch at a cafe. In my long dress I kept the appiontment with a now modestly dressed Cheryl, who looked like any other woman if a little tall, unlike the tart she had appeared to be the other night. We chatted about what we were, how we came to be cross dressers, Cheryl intrigued that I was doing it to even up numbers in the group. Then we both went back to Cheryl's house some way from the front. We had talked of styles and how to disguise the male give aways when dressing, but as it was all new to me, Cheryl offered to show her what she meant in a practical way.
Once a cup of tea had been organised, Cheryl showed me the tricks to her figure, as she undressed the corset was obviously pulling the waist in, but the realistic bust and neat crutch took a bit more explaining. I was fascinated as I saw the naked Cheryl emerge with hidden cock and balls below, and a false chest above. Seeing how I was enthralled by this, Cheryl who enjoyed the flattery she was recieving, as well as the oppurtunity to show off, offered to give me a good naked look. An hour later I walked out of the house with a realistic bounce to my chest, due to me now having C cup falsies glued there, and tape restrianing a flat crutch that did not matter in the dress I was wearing but felt sure would enhance anything a little tighter. The girls noticed as soon as I walked into the house, the more prominent chest was clear beneath my dress. I was immediately taken into a bedroom and asked to reveal my changes, for some reason I went all coy about being naked when a few days ago I happily stood in front of them while they transformed me into Maria. I did not go past underwear but they all told me I should try something tight fitting later.
About eight, the four of us were ready and went to collect our respective partners, I had got a good reaction from the girls, but the boys just stared at me. The tight skirt revealed nothing and the sparkly vest top revealed everything, I went over to Paul put a finger under his chin and made a joke about shutting his mouth, while the others reminded theirs that they were supposed to be with them. We had a good night out, I felt most at ease in the gay bar, so that is where we ended up. I would even say I was getting used to heels as I managed to dance in them, but did hang onto Paul's arm on the walk back. Once in the bedroom he helped me underdress and was shocked that I maintianed the figure in bra and pants, he was so excited his erection was rock hard without help and just went inside me without any warm up routine. I did get some tingles before he came, but nowhere near as good as I wanted. Later when I was cleaned up and ready for bed, I explianed to him that I was not going to be any easy lay, I wanted my moment as well. If he wanted me to satisfy his needs he would have to fulfill mine. He promised to make me come next time, maybe the fact that I was sucking his cock at the time had some bearing on the answer but I had made my point.
We were half way through the first week and I was totally taken with whole new experience, and just wanted more. I dressed in a tight top and the shorts that day. I went for a bus ride with Paul to Fleetwood, wandered around the shops, then walked barefoot along the sand to meet the others. As we walked I tried to explian how I was feeling and expressed my desire to experience as much of this femme life as possible in the next week and a half. I also tried to understand how I was enjoying gay sex, liked looking at boys and being Paul's partner, but had never before considered myself gay at all. Paul just kept it simple, I looked like a hot girl, so he would treat me as one. That night he was as good as his promise and made me pant before I tensed and arched into his thrusts. My last words were thank you, before I fell asleep exhausted.
On Thursday things got a little tense around the house, Matt and Steph who had been sharing made it clear they wanted a change and the others fell in with the idea of have a change around, the outcome of this was that I ended up with Matt, who in his preferences this time had put me top. So after a shuffle around of clothing, I was sharing with Matt and quickly asked for a little passion which I willingly complied with, soon I had my skirt around my waist and his knob inside me making me want him more. We did venture out to eat and get a drink, but by the time I finally put on my nightie to sleep in, he had been inside three times and made me come every time. This only reinforced my desire to live out the holiday as Maria and make the most of this short time.
Friday gave me an oppurtunity to live out a new part of the life I was creating. Cheryl called and asked if I was free at the weekend, of course I was, I was on holiday. Well she had a costume for a gay pride float and the girl who should have been wearing it was ill so would I fill in for her, I did try to resist and thought of a few negatives like I was still unsure of myself, but she just said nonsense, and I should be at her house for seven for a fitting. I explianed to Matt where I was going and told him I would be looking forward to satisfying our needs later which seemed to make him happy. Any way I turned up at Cheryl's in a loose top and puff skirt. I was treated to kisses all round and told to make myself at home, the drinks were in the kitchen. I had two shorts before I had chance to take stock and take a soft drink. My costume was a spanish looking outfit, bolero jacket with puffy sleeves, and a wrap around skirt that did not quite wrap all the way round, leaving my bikini briefs on show, I objected to being so exposed in public, but then I got a look at the others, Cheryl was in a similar outfit but with less of it, Julie was in a gold swimsuit, and Kay was in a body fitting black catsuit that made her look quite severe, but at least she was not going to be showing her knickers. It had been explianed that it was to raise funds for AIDS care, and found myself agreeing to meet them the next day. I also found out that CDs are quite varied sexually. Kay's wife came by later to pick her up, and Julie made a pass at me asking if I fancied going out after then round to her place, the implied sex was easy to spot. I was a little confused that another man in a dress could fancy me and told her I needed to get back, but not before she had made it quite clear I was her type as she kissed me very passionately before I left. I was ready for Matt when I got back and I was not dissappionted with his attentions.
The next day I meet up with the women as they decorated the truck they were using as a float, Matt came along to give a helping hand along with a few very well toned men who made it clear Matt could join them anytime, but I was just a girl. With an hour to go I found myself in a camper van changing into my costume and doing my make up in a more dramatic stage style, Kay produced some platform heels for me to wear, they looked frightening but when I stood still I realised the heel - platform hieght was not that great and soon gained the confidence to walk in them. Matt loved the look, and as we kissed slid a hand over my exposed bikini knickers, which just made me more uncomfortable as the tape fought with my penis.
To say I had a fantastic time parading around, letting holiday makers take photos with me, teasing men who clearly knew we were men, yet still reacting well to our our flirting, and being given drinks along the way until I had no idea how much I had drunk just that I was very happy with the world. The afternoon left me with a great feeling and buzzing from this new found experience, I was really enjoying dressing up as a woman, and behaving as one even in a very public place like a carnival. We came to the show ground where the trucks parked up and we got a rest, Kay's wife had made us some food to eat and four outragouesly dressed men sat around and ate quite understated sandwiches and drank coffee from a flask, before we let the judges assess our float before we dismantled it. I felt a bit deflated to see it all go and as the truck drove off I did wonder what next. We were still all in our costumes and with Kay in her dominatrix outfit and us looking like drag queens, she took on the role of her outfit and told us we were going out, when I asked if I could go and change she went all severe and told me I looked great, why waste it, then looked at the three of us, and she started telling us we were her sissys to do with as she pleased, any displeasure would be punished and we were to follow her instructions without question. I was getting worried as I had heard about domination games and did not fancy it, then Cheryl started laughing followed by Kay and Julie, I missed the joke as it was at my expense, but apperently my face was a picture. We did go back into town still dressed, just to see what reaction we would get from the places we visited. Matt joined us and got sucked into the general high spirits of playing to the crowd as we paraded around. Eventually tired and drunk I made it to bed and for the first time in days went to sleep without sex.
The Sunday was a bit of an anticlimax after the fun of Saturday. I was quizzed about the parade by the girls and Matt obliged with showing his pictures on his camera. Me in costume, me on the float, me flirting with the crowd, Kay trying to look dominating, Matt kissing me. All had some story to them and the girls loved the idea of me, the quiet lad being so extrovert in my new persona, all I could do was smile and make no comment as I knew there was some truth in what they were saying.
Later we went out as a group, I modestly wore trousers and a feminine top. All we did was walk along the front, sit on the sand and chat. The significant part for me was that I was either in the girls group or with with Matt, I was not one of the lads anymore. In a week I had shifted my own self image to that of a girl and was behaving as one more and more. In one conversation the girls asked me what I would do with the remaining week. I was certainly going to stay as a girl but beyond that I did not have much idea of what I could do. So as the boys went of the play in the water they came up with a plan let me experience some of the more feminine things involved in being a girl, then we walked back through the shops to pick up some vital products before heading to the house and my new experiences.
First off they made me washed my hair and then without telling me what colour it was they dyed my hair, while that was working a lump of ice and a needle had my ears peirced and hoops inserted. The hair was then rinsed and finished, my shock when I saw I was now blonde with what to me looked gigantic 2" hoops left me wondering if I was right to want more girlie experiences, but before I could air any concerns they were plucking more eye brow hairs out. We decided that enough had been done for a day, but that I could be finished off properly Monday morning.
Matt made me feel better by telling me how great the new hair colour looked, and asked if I was planning anything else, I answered truthfully that I was not entirely sure as he lifted my arse and pushed his dick inside me until I moaned with pleasure and pumped his semen into me.
The next morning once we were all up and functioning I was told the next stage of my femininisation would happen. First up was having long nails glued to my fingers and painted a rich pink colour, then I was given what they called a master class in make up, which was very informative as they shared tips on how to do things, then at the end before my lips were made up a clear liquid was brushed on them which made them sting, when I asked what it was Cat would only say wait and see. I had no chioce and watched as my lips swelled from their normal thin line to much a fuller mouth, then coloured I knew I had much sexier lips. But they were not finished with me, I was taken to a hair salon much against my wishes, firstly because it would be expensive, then because I might be found out, then because I did not want a new style. They just railroaded me into the shop, paid for me, had a word with the stylist, then sat and waited. It was like a torture being watched by them, and being under such scrutiny by the the staff. But in the end my blonde hair was striaghtened and curled under my chin, giving it a very nice look. The girls all approved of the new look and told me one last thing that we had to do was shop. I was not given much chioce once again I was taken rather than went. By mid afternoon I was all kitted out. A black slip with a sheer black over dress, niether barely covering my black thong, and on my feet they had found what were termed fuck me heels, I just knew they were high and thin. Early evening I was given a final once over in Cat's room before Matt was told they had a treat for him, at which point I was paraded out infront of him and the other three lads. I felt so embarrassed to be there on show, rather like a prize animal being offered up to be judged. Matt came out with a 'Fuck me' comment which got the response that, that was not the idea, rather he fucks me and he had better go and smarten up and take me out somewhere special so I could get the full benefit of looking so great. Then one by one the other girls came into the main room all dressed up and telling their partners that they were not being left out. Soon four very sexy women were being escorted by four ok lads to a bar, then a club and finally to bed where their hours of sexual frustration were released.
The Tuesday morning was largely missed due to hangovers and tiredness, but as Matt and myself came to life I realised how much I liked the feel of my silk nightie and the soreness between my legs reminding me of past pleasures, so when Matt said 'Penny for your thoughts' I told how much I liked being his girlfriend, how it was not planned, or even considered before we came but I was now a committed girl who only had a week left before I had to go back to being a lad and start my summer job packing boxes in a warehouse. Matt's response was encouraging if a little selfish, he suggested I make the most of the week, be as girlie as possible and for his part he would treat me as his woman, and when I questioned if that included screwing me, he just said of course it did, and being girlie in his eyes was to be sexy. When I suggested he would like me to flaunt myself all the time, short skirts, high heels etc, he only said 'That would be nice'. I let me hands explore his body while this conversation ran its course, finishing up with an erection in my hand, which I rather too willingly ducked under the sheets to bring to a climax with my mouth. When I came back up I told him 'Treat me well and I shall make sure that dick is sore by the time we leave' he turned to smile at me 'That could be a challenge, but one I will enjoy taking on. Now then my lovely chick, I think a mini skirt this morning and the see through top if you don't mind'
The week rather continued in this vain, I would dress as he asked, which was usually in a tarty fashion, and I looked forward to getting his prick to touch that button inside my hole which made me tense and shudder until my body erupted. I also lost any sense of decorum, shamlessly flaunting myself infront of him encouraging him to get randy even in the morning in front of our friends who later told me that they were growing sick of my exhibitions, but at the time I did not care.
I managed a couple of nights out with Cheryl and her friends, and without Matt realised that I could have quite a selection of interested parties who would like to be entertained by a person such as myself, I was slowly recognising how many different oppurtunities could be available if I ever fancied to live a wilder sort of lifestyle. But for then I chose to stick with Matt as it was proving to be great fun.
That was until Saturday, we had to be out for midday and this meant I would have to be going home as my parents would expect me to be, their son. Friday saw us all out having a good time in the bars, then back in our beds entertaining our partners until the early hours if the sounds of sexual activity was anything to go by, for Matt that meant he penetrated me twice and I finished him off with a final blow, before he gave me his leaving present, a dildo, which he inserted and switched on so I could continue my pleasures and remember him when he was not around to service me. I lasted one orgasm before I removed it and had to accept I needed sleep.
The morning was not just about packing and tidying, for me it meant also removing all the femininization bits. I was sad to see my body regain it's boy shape, and the genitals reappear, then the nails came off, but even with a good shower and plenty of make up removal I was unable to do anything about my hair, the girls suggested I dye it back to my natural colour and mybe get it cut, I could let the ear piercings heal, but probably because I wanted to hang onto the echos of the holiday I replaced the hoops with small studs and did nothing to my hair letting fate decide what would happen to it when I judged the response from home. As for the clothes I put them at the bottom of my bag so it was not to obvious if I needed to get something out.
The parting at the station as we seperated either in cars or onto a trian for me was awkward, I was now a bloke the same as Matt and that meant our view of each other had somehow changed, I managed to hug the girls but without the familiarity of the past days. Then as I finally said good bye on the platform to Cat when my train was due to leave I felt a deep sadness at what I was leaving behind and would possibly never experience again. I had a couple of hours to watch the scenery go past and I felt my holiday being left behind, but that was replaced by a sense of forboding as the train get ever closer to my home town and the inevitable meeting with my mother at the local station as she had promised to collect me and my luggage, but what would she make of the blonde neat hair I now wore, and with no option of calling anywhere on route to change it, I could only sit and worry about the possible outcomes...............................................................
What will happen to Mark when he gets home, what will his mother say, what will happen when he meets up with his friends when the new term starts. I leave this open, maybe some one would like to write a part 2 or make suggestions for a continuation.
Lauran (keep smiling)
I carried my bags along the platform, I could see her waiting beyond the barriers but she kept looking at the other travelers clearly not spotting me. I was nearly stood infront of her before I saw any recognition, then it was a mixture of her usual pleased smile and a questioning look. I put my bags down and we hugged as usual, she said the usual greetings but as we stood close after the hugs her hand went to my hair and she ran her fingers through the side, 'This is a surprise, quite a bold statement' then she saw the pierced ear lobe 'And those are pretty' I was starting to blush but knew I had to just take whatever was coming, I was there and with no way of going back in time to change things I was going to find out how she reacted to me, the only thing I could keep to myself was the history of why I had done these things. She continued 'I am taking it that you had an interesting time with your friends?' We picked up the bags and started to move towards the car park, but she stopped as we passed a coffee shop. I had said nothing until then 'Let's have a coffee before we drive home' I understood this as we need a chat as we never did this detour as she considered station coffee a rip off and tasteless.
'So Mark, you are very quiet, I can see you had some new experiences, care to tell me about them'. Even though I had spent hours thinking about this conversation, now it had started I was nearly panicking in my head, not sure what to say, lie, tell the whole truth or something in between. I stared at my steaming coffee and mumbled 'It was just some fun with the girls really, they wanted to see how I looked and I went along with it' her hand came over and touched mine 'The hair does look nice, takes a little getting used too but I like it, do you like it?' I looked up into her eyes 'Yes but I am not sure I should keep it, a bit shocking and girlie isn't it' 'Perhaps it is but it suits you, maybe we could get you some plainer studs but I do like the hair' after a minute I asked 'I was thinking of getting it dyed back to my natural colour and having a trim' she came back immediately with 'Why, you are young and if you don't do these things while you are less restricted you never will, once you have a job and have to conform to dress codes such fun with how you look will be missed. No if you like it then you keep it and don't mind what others think.' We sat and drank our coffee, she filled me in on home gossip, but besides very sketchy details I hardly gave any information about my time in Blackpool. But just as we were finishing she came out with 'Those hoops are very pretty, not at all what a boy would choose, and the hair has been cut well and coloured properly, those girls must have been having a great time making you look this good, I am guessing it was not a drunken dare.' I was blushing again as I agreed that they were having fun, but did let her know I had been a willing partner in the fun, I had allowed them to do these things to me. 'That is interesting, I would have thought you might have been under some pressure to let them carry out the styling in particular, but if you say not then you clearly must like the idea of looking like this as well as the reality'. Sometimes I do wish my mother was not a solicitor as she can put things into words in such a way as to make me squirm. This time she had voiced how I had got my feminine hairstyle willingly, she made it sound almost as though it was my chioce, which when considered coldly it was, I could have said no at any point or left the house, I did not have to end up looking like this. So I asked 'What do you think dad will say? I can get it changed easily' she was looking into my eyes when she answered 'We can stop somewhere on the way home if you must, but this is part of you, your personal expression of who you are. Your dad might say something, but just remind of those student photos of him in his hippy kaftans and long hair. Besides I like a prettier Mark, for some reason it suits you in a way that your past style has always made me think you were just following your groups style without thinking, this has shown some thought, and quite a lot of courage. Yes I approve. Come Mark lats get home.' And that was it she had concluded her discussion on the subject.
Once home I unpacked and carefully hid my Marie items, I replied to a text from Matt who asking how things had gone, I answered, OK. Mother even lent me a pair of small gold studs which proved tricky to get in as the holes had not healed completely. My next challenge was when father came home, I kept that image of him as a student in my mind as he walked in wearing his pin stripe suit. 'Good hoilday son?' 'Yes thank you' and that seemed to be it, he went through his coming home routine of kissing mother, undressing to his shirt and trousers, getting a scotch, then looking at the post. A short while later we were eating our family meal when out of the blue he asked 'Is that it then?' I was unsure what he meant or even if he was talking to me, 'Do you have any other fashions you are going to try out, or is this it?' he was looking directly at me, I just said 'Sorry?' he continued 'Well are you going to go for reds or greens, have a mohican, tattoo yourself, pierce your nose etc?' I was understanding now 'Oh no this was it, I don't think I shall be trying out anything too extreme' he smiled at me 'So you are happy with your feminine style? Good, it suits you though I was unsure when your mother told me on the phone, but now I see it in the flesh as it were, I can see how it does work well'
That had gone far better than I had ever hoped for, no serious objections from my parents, even positive acceptance it appeared if being told I suited a feminine style was positive. The next day I had to start work at the warehouse so covered my hair with a beannie hat and spent my day working harder than I have ever done in my life. I managed two days and then my world changed. We had our evening meal together and I don't know what I ate or drank, but I was relaxed enough when getting ready for bed to catch a glimpse of my nightie and decide to wear it that night. The big event happened in the early hours, I woke feeling really sick and just had time to make it to a toilet and throw up, as I knelt there in the post sick weakness my mother, as she had done since I was child, came in to make sure I was alright. She wrapped me in a dressing gown and gave me a glass of water, before making sure I was over the worst and taking me back to bed and making sure I was comfortable.
In the morning I woke feeling terrible, father had looked in on his way to work and made some remark about hoping I felt better soon, then mother came in to see if I was wanting any breakfast. I was alert enough to keep the duvet pulled up, but also had to acknowledge that she must have seen my nightie in the night. She rang work and told them I was sick, then brought me some toast. Soon I was feeling better and it was decided I had eaten something which had disagreed with me and now my body had got rid of it I would soon be up and about.
When she came in later with a drink she brooched the subject of my nightwear. 'I think you need to explain why you were wearing a nightie last night' the truth was I could not think of a good excuse 'I can't explain it really, I got it while I was on holiday and I like wearing it. That is about it.' She looked at me for a moment 'It is a very nice one, silk?' 'Yes' I confirmed 'Good chioce, have you any others?' 'No I only bought the one' she was clearly thinking about how to manage this news 'Would you like me to lend you a clean one, that one will need a wash now?' I was taken aback by this offer, so she said nothing more just got up and left, returning a few minutes later with a cream full length satin nightie and a matching wrap. 'You ought to have a shower now, get the smell of you and freshen yourself up' as she said this she lay the garments on my bed in full view, there was no mistaking the offer she was making, but I was very worried about this development in the opening out of my secrets.
Slowly I got up and showered and allowed my weakened body to enjoy the warm water washing over me, I washed my hair as well, then dried myself slowly as speed was not going to happen at that time. Then as I went back into my room and saw the satin clothes mother had left for me I just thought 'Where's the harm' and slipped them on and went to get the hair dryer so I could get my hair looking right. Because of the niose I did not hear mother come into the room until she was beside me, 'Here let me do that' and she took the brush and dryer from me and very carefully brushed out my hair curling it under at the bottom. When she was finished, she left me of only to return with some spray lacquer and told me to close my eyes. 'All done. You do suit your hair like that you know.' I could feel her hand through the satin as she rested it on my shoulder. 'You feeling any better? because you are looking much recovered' I told I was feeling a bit better and thanked her for doing my hair, then after a pause thanked her for not being mad at me for wearing a nightie. I was stood at the time and got a big hug 'If my child wishes to wear something as nice as silk or this satin, then I have no problem with it' she stepped back then asked 'Do you like the satin?' I was a little lost for words but managed 'Very soft isn't it' she smiled 'I would say sensual, men don't know what the are missing' I noticed but did not comment on the way she had used the word men there, as though I was not one of them, this was to much for my frail state to handle and went to lie on my bed and watch some daytime TV. Alone I tried to watch, but all I could think of was what had happened and seeing and feeling the cream outfit wrapped around my was not helping me get any rest.
Mid afternoon there was another probing by my mother. She came in with a sandwich and a drink for me to find me sitting up, so she invited me to join her downstairs, immediately I said would get dressed, her response was to pass me a pair of her slippers, and tell me there was no need. So we ended up sat at the kitchen table eating when the probing started 'So I am guessing there's more to this holiday than you have let on so far, anything you would like to tell me dear' She never called me dear, but then she had never styled my hair or given satin nighties before. 'I am thinking somewhere along the way your friends got you all dressed up as a girl, was there just you or did the others dress as well? And I am also thinking you liked the way you looked, not surprising as you do look very feminine dear, even without make up.' Maybe it was because I was still weak, maybe I could see she had worked out most of it for herself but I felt a tear in my eye, and the stress of keeping this from her cracked me. I told her everything, well nearly everything. The dressing so we had four boys and four girls, the having my clothes hidden so I had to live fulltime as a girl, the being taken for a girl when out, the deeper friendships I made with the girls, the fun I had discovered from having such a different chioce of clothes to wear. We left the kitchen for my bedroom where I showed her my small collection of clothes which she studied carefully making sounds which refllected her view of certian styles. Eventually I stopped and she summed up what I had said 'So you have lived as Marie for two weeks and from what I can tell you have found it very satisfying being taken for a woman, but you never mentioned the boys, where did they figure in the picture. If you were not one of the boys and was one of the girls, can I assume you paired off in some way' she was still probing, but I was getting myself together again after the crack in my defences had let her know how much I had liked being Marie. With me clamming up she decided to make up scenarios and see how I reacted. She touched a few items like a mini skirt and the high heels, and commented that these items were definitely not designed for comfort but for their effect on the opposite sex, and seeing as how I had more than one such item as well as a short silk nightie, she surmised that I been playing the part of a girlfriend to one of the lads, and seeing as there was a sexy nightie in my things, then it did not take much to think I had slept with a man. My head was down as she worked out the truth from the evidence, in the end all I could say was 'Sorry' 'What for' she asked, 'Your son has let you down, I am supposed to be a man, be like my father, get married, have kids, all that stuff' I was beginning to tear up again, so she sat beside me and hugged me. 'There is nothing to be sorry about, you have enjoyed yourself, seen another side to life, experienced things I never thought you would, but I am pleased that you have, there, there, dry your eyes, good job you had not got make up on, it would be a mess right now' that got a smile from me 'That's better. Now what you have to think through is, whether this is just a phase you will grow out of, or something that goes much deeper.' she paused so she could lift my chin and look me in the face 'As far as I am concerned, and I know your father will back me up, you have to be you, if you deny yourself who you truly are it will just frustrate you and cause other problems if you try and be someone you are not.' a pause for breath 'Right, that's enough I have some work to do and you have some thinking to do princess' she hugged me and kissed my cheek. 'I suggest you get some paper and make notes, then see if you have a clear answer' and with that she left. My clothes were all out and needed putting away which would be easy compared to the task she had given me, which was not helped by the final word she spoke, she had called me princess, a clear indicator of how she thought I should proceed.
The evening was thankfully easy to handle, father was working late and I was not up to eating a full meal so ate some toast in my room. I had done as mother had asked and made notes, and for and against lists, but had not come out with a clear chioce. I must have fell asleep on my bed as I woke with a start to find father in my room sat at the bottom of my bed looking concerned. 'You feeling better' waking up I said 'much better thanks' then he looked at my body or more precisely my mother's cream satin wrap that is was wearing. 'I hear you and your mother have been having a chat today' I thought of him in his kaftan 'Yes we have' 'Come to any conclusions yet?' he asked 'Not yet I'm sorry, all a bit complicated when you think about it' He looked at me and seemed to be taking care of his next words 'Well you have not changed out of the feminine things your mother gave you earlier, so I would take that as a strong indicator. You could have refused at the time, you could have changed knowing I was coming home, but you have not, therefor I think this is going far deeper than a student prank.' He gave me time to absorb what he had said 'It is for you to decide, but whatever you feel is right then I shall support you be it as Mark or Marie' this was all said in his serious vioce, then he got up to leave and put an affectionate hand on my arm and quite casually said 'Sleep well, you should be fine in the morning dear' he always called me son, this was getting as though they wanted me to be a girl, what with all the words of support and terms or endearment, it was as though I could dress and no one would bat an eyelid.
The next day I made it into work, but still not 100% it was tough with all the lifting and not having eaten much the day before. I got home completely washed out but ready for a nice meal and sleep. Mother took a call from her sister after the meal and I cleared away the pots and tidied the kitchen while father went to watch the TV. It took me a while to finish but as I did she put the phone down on clearly what had been a more serious call than a gossiping chat, she thanked me for doing the cleaning then went to sit with my father and shut the door behind her, clearly I was not to be included in this conversation so I went upstairs to rest and get ready for bed though I still had a couple of hours before I would sleep.
An hour later my parents knocked on my door and entered, I was wearing my mother's night clothes curled up on the bed reading a Cosmo magazine. Father started 'There you are, something has come up with you auntie Jen' I could tell from their tone and body language this was not going to be an easy chat. 'Thing is' mother put in 'Jen needs some time away and was hoping her kids could stop here for the summer' I was confused 'Why ask me, we have spare rooms and they can't be that horrid' 'Well not as we know, but then we have not seen them for years have we? Anyway Lucy is eight and she looks fine, though besides at the christening I have not seen her and Brendan is sixteen and looks ok.' an awkward pause before mother continued, 'What we thought was, they come and stop here, they will need looking after, Lucy especially, and we were thinking that this job of yours seems a little beyond you at the moment with you being sick. What if you let Brendan have the job and you stop home and mind Lucy' I nodded to say I was following their suggestions 'And what if because you no longer are going to work, you live as Marie while you are minding Lucy?' That last sentence stopped me in my tracks, 'But they must know I am Mark, your son' they had clearly thought about this, 'Lucy does not know you, and Brendan is old enough to understand such things' 'And what happens When Lucy tells her mother' 'We will explian everything to Jen beforehand to make sure she is fine with the arrangement. Any more questions?' I thought for a minute 'Why are you so keen to let me do this, most parents would want their son's to become men not women?' Father answered that 'We think you need to be helped making your mind up, and this will commit you to being Marie fulltime, and then all of us can see how well you handle being a girl, with there being a date set for the end of this trial period. It just seems a good oppurtunity if you want to use it' I was letting this offer sink in as they left, mother saying she was going to call auntie Jen and tell her I would not mind looking after them. Five minutes later I went downstairs to tell them I would do it as Marie, mother gave me a big hug and phoned her sister to explian the arrangements.
Mother sorted everything out, she spoke with auntie Jen, who I was told was fine with the situation, she rang work and they accepted that I was not up to the job and were pleased she could send a replacement, obviously they would need to make sure he was suitable but in principal it was fine. Then she decided I needed some more suitable clothing if I was going to be Marie all the time, the kids would be coming on Sunday, so that meant Saturday was shopping day. I had not shopped with her for years but did remember she was good at it. I was not sure if it would be a good experience or not.
My parents fit into the gender stereotype very well, father is a man and wears suits for work, has a set of scruffy gardening clothes and a small collection of not so casual clothes for when he is trying to be not at work. Mother though a successful solicitor does not wear trouser suits and do the power dressing very well, she wears softer and more feminine styles almost stating that she is not trying to be a woman in man's world as some women do with their masculine styles.
The Saturday morning started with me dressing for the first time fully as Marie at home, I had given the breast forms back so had to rely on socks in my bra, and to keep on mother's good side wore the long sun dress instead of a mini skirt, which had the bonus of not needing to hide my male bump to tightly. I had had a shower involving a full body shave, mother had dried my hair and given it the volume I had seen on holiday, I used her cosmetics to do my face, keeping it simple and impressing her with my abilities, even getting a compliment about how good I looked, how well I applied the products and how I must have taken the situation on holiday more seriously than she at first imagined. Once ready I was given a little pep talk about how I should behave and look from that day on. Until the cousins went home I was not to wear any Mark clothes, in fact I would have to bag everything up and put them in the loft. I was going to hopefully project the image of a feminine girl, therefore I would not be getting any flat shoes, a heel she reckoned would keep me in mind of the fact that I was a girl, at least to those who saw me. She would prefer I wore skirts and dresses, but even if I wore trousers I should wear heels and the trousers would need to be tailored women's styles. She had done some research and had found a local supplier of breast forms which she said were not cheap but would be toned to my skin colour and I would be expected to wear all the time, even in bed. She was also prepared to buy a contraption which hid my genitals between my legs and importantly for her it seemed would make it impossible for me to stand when urinating. I had little trouble agreeing to these wishes as I had already spent over a week in that situation, but nodded and said the right words so she knew I was in agreement. She did however make some demands which as she put it would limit any easy flipping between genders, she wanted me to have extended acrylic nails, I had the choice of french tips or ovals, but not whether I had them or not. My eyebrows were to be shaped, and tinted along with my eye lashes. And I should have a nose stud, this was something she had seen on young women and thought it appropriate that I have something so definitely female in the middle of my face. While on the subject of peircings, as soon as my ears had healed I was to wear clearly visible jewelry, her suggestion being hoops no smaller than 30mm or pendants no shorter than 50mm, just so I know they are there and others can see them, necklace, bracelet and a ring were also on the list of regular decorations she wanted me to wear. Then when I was all sorted I should have a spray tan while wearing a bikini set, I asked why, so I have clear girl tan lines which will stop me from going anywhere as a boy and being topless. She also said when it tones down I will look good.
For my part I did not have any immediate problems with her proposals, I wanted to find out just as much as she did, whether living as a woman was the future for me. Mid morning we left father reading his paper and drinking coffee. He gave mother a kiss as they always did, but followed that by unexpectedly kissing me on the cheek and telling me to have a good day. Up till then we had barely touched, he barely touched other men other than to shake hands, but women he would hug and kiss in greeting. This simple action told me I had moved gender in his eyes, I was his daughter now, which took a little getting used too as the reality of what was happening sunk in.
The day with mother was exhausting, interesting, illuminating and totally enjoyable. We first had an appointment at a place that helps men like me, cross dressers, she had found this shop on the internet and was assured they could supply breasts and what they called gaffs. Mother rather took control and soon I was in a changing room, stripped and being examined for skin colour and size. The whole procedure took about an hour to complete before I walked out to meet mother fully dressed but sporting a very realistic pair of gel boobs, tear drop size D I was told, and was not sporting anything visible between my legs. With the use of ice, surgical glue and a specially shaped penis holder I now looked female naked. I was completely amazed and knew mother would want to see the new me when we got home, but I was a little unsure as to how she might react to the transformation. Anyway we paid and left for the shops. After a preliminary look around to see what styles we liked, we rested for coffee and cake. It was in the cafe that I had a few more rules laid down, just so I was clear about things, I was not to look 'common' anyone can look like a cheap tart she informed me, her idea was that I should be feminine, chic if possible. I agreed to aim for chic, but did point out how many girls my age do wear flat shoes, mini skirts, jeans and revealing tops. She just said that was no reason for me to copy them, but did point out again why flats and jeans were not to be in my current wardrobe, though did accept that depending on how this trial period went she would not be controlling my wardrobe in the future.
After our coffee we started buying. A soft cotton skirt. Sleeveless cotton blouse. Silk blouse. Knitted vest top. Several underwear sets. A lightweight jacket. A handbag. Two pairs of sandals. They were clearly for summer and the colours reflected that, pastels, cream and white, nothing strong. All fitted into her image of a smart young woman that I was going to be. This was she explained just a basic starting wardrobe, I would expected to add to these clothes over the next few weeks as my style developed. This bare list does not convey the fear I had as we tried on things to make sure they fitted, nor the embarrassment of having your mother come into the changing rooms with you, to check that I looked good. Anyway that fear overcome and feeling quite drained she informed me we had an appointment at Nailz, and directed me to the shop where an over made up assistant escorted me to her station and asked me what I wanted, I told I was not sure and asked what was popular and most of all smart, not tacky. I walked out some good while later with long french tips, the tips a dusky pink the same colour as my toes. Then I spent time with a girl who waxed my eyebrows into fine arches and tinted them and my eyelashes black. Physically I had rested but psychologically I was shattered. so I easily accepted the offer of a nose stud, not because I did not want one or anything like that, more I could not be bothered thinking for myself, if she had said we are going to put a bull ring through your septum, I would probably come out of the shop with a nice gold ring below my nostrils. Instead I came out with pink stone on the side of my nose which honestly looked very much the part we were aiming for, obvious and pretty.
We got home to find father in the garden, he wanted to know about our day and what we had bought, so I went and changed into the silk blouse, and a long skirt. When I returned my parents were sitting on the lawn drinking white wine and looking pensive. 'Princess, we feel we ought to explain some family history to you.' The princess missed me that time, it was the tone that caught my attention. I took a glass and sat down then they told me why I had not seen my cousins for so long. My father and uncle had fallen out big time possibly ten years before when father accused his brother in law of beating auntie Jen. Jen admitted it was true but would not leave him, father responded by saying that he could not be held responsible for his actions if they meet, so the two families never meet, mother and her sister did meet and talked on the phone, but we also lived at opposite ends of the country, which suited father as he never had to find an excuse for not visiting. Aunt Jen now had cancer and she was starting the chemo which she knew would lay her out for long periods and looking after a family would be too much for her to cope with, so that was why we were hosting my cousins. Quite straightforward really.
As I listened and the wine relaxed me, and my feet stopped aching I was able to enjoy the summer sun on my skin and feel the breeze run through my skirt and over my bare legs. I could get used to this I thought, it just felt so luxurious as I sat back on the lounger. Then I thought what about my uncle and maybe neighbours, my concern must have shown in my voice, uncle would not be told, the kids sworn to secrecy as he would not be understanding, the neighbours I was reassured hardly knew who I was since we had moved with father's job, I had started uni and they had not made many friends, and I had only meet the odd local such as postmen on the few weeks I had been with them. So it was easy for Mark to just disappear and for Marie to take over. I was then asked 'Are you sure this is what you want to do?' I looked at them, then as I took a moment I emptied the last of my wine and I considered how I looked, 'Yes.......I am sure'. 'Good, because this is how you will be until the end of summer, we will not have you doing this living as a woman at anything less the 100%' I topped up the wine glasses 'I do understand, and I do want to find out if this is the real me' Then gave each of them a hug and thanked them for being so generous in giving me this opportunity.
That night I had a new nightie to wear but it did not help me sleep, I was still concerned about exposing my new self to our visitors. I spent an age getting ready not knowing what to wear for such an occasion, in the end I wore a white skirt and pink top and joined my parents for the drive to the airport where we would collect the children from.
The meeting was as strained as I expected though mother did try her best to keep the chatting going. I knew this was going to be hard but just focused on being the feminine me that I had developed over the past weeks. Lucy was a cocky young girl who was a proper girlie girl, she was all dressed to look pretty, whereas Declan was a boy, well built and scruffy in jeans and hoodie, very stereotypical, but that was fine with me, just as long as they did not expect me to conform to their image of what a lad should look like.
We had a very formal evening, they were shown their rooms, and around the house. We had a meal mother prepared while they unpacked, everything was ok, just a little stiff and conversation forced. Possibly the shock of knowing their mother is so ill, maybe being in a strange house, maybe being with a boy who wants to be a girl. Who could tell but I decided to let them have some space and did not go in being pushy and over friendly. It was once I was alone with Lucy on the Monday that I had my first question 'Is it true you are really a boy?' I answered honestly 'Yes I was born a boy' she let this sink in 'so why do you want to be a girl?’ I had rehearsed this one. I asked if she liked being a girl, she said yes she did, so I asked what is wrong with me wanting to enjoy being a girl as well. This logic stopped any more questions, she just asked if I was somehow born with the wrong body, like I should have been born with a girl’s body but I came out with a boy’s by mistake. I liked the idea and said yes I was a girl inside, just the outside lets me down.
After the first few awkward days with Lucy we seemed to click. I took her shopping, on top of the house keeping money I had of mother, there was also a clothes allowance which she said I would need as I would not want to be wearing the same outfits all the time, nor would she want to see me in the same stuff day in day out. So we went to the stores to see if I could find something nice. I came home with a nice lemon sundress, a bikini which was not skimpy, and a sarong. Lucy took great delight in helping me choose, and though I treated it as a game I think she rather took her role as fashion advisor more seriously. I treated Lucy to her first proper bikini as well, which went down well. Mother came home to find us sunbathing in the garden talking about Lucy's boyfriends.
Part of the deal was that I look after the house as well, so I would clean and cook, sometimes with Lucy helping. But I made the effort everyday to do something with her, taking her swimming, to the ice rink, the pictures or just a walk in the park. But what she liked most was being a girl and shopping, sometimes we just went to the shops and looked around never really intending to buy, just browsing and trying on. She soon found out I was easy to manipulate, during the second week I was up late so made everyone’s breakfast in my night clothes, I was still in them when Lucy got up who told me they were gorgeous, within minutes it seemed I had been persuaded to buy her something similar because she was getting to grown up for little girl pajamas. Sure enough that night she slept in a pink satin nightie proudly showing it of to mother before bed. Unexpectedly this incident gave me an insight into why my mother had been so tolerant, as I took Lucy round the shops I got pleasure from helping the little girl dress up, which I reckon could have been subconsciously in mother’s acceptance of Marie.
A change in the parent child relationship happened quite unintentionally, the children were encouraged to ring their mother often so their contact remained strong. This lead to a conversation with Lucy that mother was listening too. I asked Lucy if she was going to call her mother, to which Lucy replied she would call her mummy after tea, but followed it up with another question about why do I call my mummy mother and not mummy. I said I had never thought about it, I had always called her mother and was not that sure she wanted to be called mummy. Lucy with childhood confidence assured me that all mothers like to be called mummy, and when she has children they shall call her mummy. At this point I turned to mother and asked which she preferred, mother, or mummy. Lucy went over to her and informed her she was a mummy, which seemed to sway her answer. 'We could try mummy, now we have two princesses in the house it will fit us better I think' And so from then on I always referred to her as mummy or mummy dear, and she hardly ever called me by anything but an affectionate term like sweetheart or princess.
The six weeks of the holidays rolled by very quickly, Lucy had become my best little friend who would confide in me some of her deeper thoughts, but she was at her best when she was being really girlie and guiding me through the maze of women's styles. Our best times being when we styled each other hair, she had some curling tongues which meant I could make her long hair into a mass of curls. She in return would blow dry my hair giving it such volume I was genuinely in awe of her abilities.
All this time I had kept in touch with Matt and the others, letting them know some of the developments in my personal affairs, for some reason I did not feel able to fully admit to them that I was living full time and could not imagine returning to being a dull boy any time soon.
September came and auntie Jen was still not well, mother or should I say mummy took the kids back to see her and for whatever reason when she came back a few days later, Lucy came with her, Declan it was felt could look after himself and help his father look after Jen, but Lucy given half a chance asked to come back and stop with us. This meant school enrolment and other stuff that my parents sorted out, but what it did mean was that the conversation I was going to have with my parents when mummy got back was impacted on by the presence of Lucy. We were supposed to be having a chat about how the summer had gone with me being a girl, and what was going to happen from then on.
The first thing to discuss was whether I had succeeded in my aim of living as a woman. It was agreed that I had, surpassing any worries that I might have been an odd looking or behaving girl. The second topic was how to proceed if I stayed female, I was unsure about going back for my final year, but father wanted me to complete the course, and then there was Lucy. I suggested that I take a year off, which would mean I go back and continue with the year below who would not know me, which would make things easier. In the mean time I would be around for Lucy. I also included that during that year I could seriously move myself towards true transitioning which would make my return to uni easier. I could see the permanency of this idea was unsettling my father who though he said nothing was reluctant to admit the loss of his son. So made special efforts to be as girlie as possible, highest heels, most body flattering dresses and most important, treat him like a man, let him feel in charge and pander to him so he feels important. Within a week he had been onto the university and arranged everything, even down to my name being changed for when I start in a year’s time.
Then the topic of how far does wanting to be a woman mean when it came to my physical body. I said I was 99% sure that I wanted to live as a woman, the odd things that tugged me towards being Mark again were more than outweighed by the prospect of giving up my new life. Within the week I had seen our GP, been referred to a specialist and had a series of counseling sessions set up, which culminated in the professionals agreeing that I was suitable for gender reassignment. They advised a period of full time living but I was impatient persuaded my parents to at least allow me to get me breasts enhanced. And for my Christmas present, that is what they gave me. They also made me work at father’s office doing telephone answering and filing while Lucy was at school, so I was forced out into the big wide world.
My transition I know went very smoothly, no major obstacles outside what went on in my head. By the time Matt called to tell me had got a 2.1 and a job in a retail chain, I was happily wearing a bra which supported my very own breasts, was due to take my final year, following which I would go for the full reassignment and besides not having ovaries, would become the full woman I desired to be.
This is from the archives, I hope it is not too bad.
It had been at college for my first term, and was looking forward to going home for Christmas. My father had said he would come to collect me, which was unexpected, but welcome. The reason for his generosity was related to mother, she was a frail woman who had not really wanted me to go away, now I was being told she was becoming confused. It seemed since I had left, my absence had brought back some uncomfortable memories. And rather than confront them, my father had gone along with them. As we drove he explained how after two sons, I was supposed to be a girl, and mother was devastated when the midwife proclaimed me male. I remembered being encouraged into dance class and not football, and while my brothers played rough, I was told to play quietly. Still, I had enjoyed my childhood, and had enjoyed my term at college studying drama. My mother without me to remind her of my sex had forgotten I was male and referred to me as Lauren instead of Laurence.
So prepared for the worst I arrived home hoping that my male image would remind her who I was. Unfortunately as soon as she saw me it felt wrong, she wanted to know why I was dressed like a boy, and what had happened to me that I should come back looking so unfeminine, after she had spent so much energy bringing me up to be a girl. I gave up after a while and went to my room.
The next day I hoped everything would be back to normal, but before he went to work, father came in for a word. Mother had had a bad night being upset at my return, and she was now adamant she had two sons and a daughter. He left wishing me luck. I eventually plucked up courage to go downstairs, but was meet with a mother upset that I persisted in dressing like a boy, I made an excuse and went out to see how my friend Neil had fared at uni, not intending to return until late. It was dark when I returned, and father was home. He was looking out for me as I arrived, he had a proposition for me. To help mother we go along with her fantasy and let her see a daughter, apparently she had been really upset at me dressing like a boy, and then going out. I was not keen and objected saying that I only had my own clothes. Father had already thought of this, we were going round to my brothers where Jill (my sister in law) would sort me out with clothes so I could return as Lauren. I suppose I was still young enough to do as I was told and just accepted that he knew best.
Jill had already sorted out a jumper and trousers, they were definitely ladies clothes and I was not sure this was right, but father was in a hurry to get home so I changed into a lemon top and embroidered white jeans, then followed him to the car. To my relief it worked, mother was as I remembered except she kept calling me Lauren, but we chatted like before and I forgot about the clothes, happy to be at home.
Next morning I got up as usual and drifted downstairs for breakfast, only I had dressed in my black T shirt and jeans, and when mother saw me she had a face which expressed the disappointment, she did not need to say anything, I ate and went round to Neil’s where I stopped until the evening. Neil had been my best friend for years, and as this was the first time we had been apart, it was not a surprise we had plenty to talk about. Although there was one subject I could not mention, no matter how close we were. At home I got a cold reception, and went to my room, to hide more than anything. Father after a suitable pause came for a heart to heart, this was distressing him to see his wife so upset, and there was no other solution he could think of, he wanted me to dress like a girl. I had only been home a few days and feeling this was no way to carry on. What about therapy I kept on suggesting, he said he had tried but she refused to see anything was wrong, if I would play the role it might calm her then he could get help for her, and maybe sort things out. All I could offer was to think about it, and said I would talk to Jill and Bruce about it tomorrow, as it was by then too late.
So in the morning I crept about, rang Jill to see if she was working. She was on a late so I went round but with only an hour before her shift started, I had to get to the point. She had seen this coming for weeks, it was no surprise when I borrowed the clothes, and father had already talked to her and Bruce about what to do, and they had all tried talking to her, to no avail. Ultimately only I could make the choice, if I went along with being a daughter at least for the holiday then something might get sorted in the new year, but for now I had their support. Adding ‘I don’t know what you are getting into, it’s up to you to work out if you can handle it’ so that was about it, there was support but it was my choice. I asked if I could spend the afternoon there and see Bruce later. She agreed and went to work, while I mulled over the options hiding out in their living room watching daytime TV.
Unfortunately Bruce only repeated what Jill had said, but I could tell our mother was a concern to him, and was really worried, if anything he hoped I would give it a try. I then rang Phillip my other brother who had moved away, he had seen mother a month ago, and felt rather helpless being so far away, but if I gave it a go he would also support me. It seemed the balance was in favour of pleasing mother short term, then get her some help and everything goes back to as it was. I made my decision and asked Bruce to be more open with the help, which turned out to be Jill’s job as she is female and a little smaller than me. I went of home knowing I would have to sneak in, but also wondering what the next day would bring when Jill called round.
I had not slept particularly well since getting home, but that was not a good night, I just kept on going over and over in my mind the reasons for taking this action, and trying to convince myself it was right. In the end I decided to dress up while in the house, but would change to go out, realising this would mean a bit of sneaking about, but I felt I could keep something of my own life this way, and it was only for a short time till I went back to uni.
Jill turned up as arranged; she had a holdall full of clothes. Soon I was in my room stripped off in front of my sister in law, not something I ever expected to happen. She had obviously given this some thought, and was able to convince me easily that it was not just a case of swapping jeans for a skirt. The collection of Jill’s cast offs were spread around the room, and I was soon persuaded into a white blouse and a stretchy tartan skirt, I thought that would be fine, but I needed a bra to fill the chest, and tights to make my legs look ladylike and cover the hairiness, I should also get some knickers as boxers in the washing might upset her, she could only find one pair of shoes, strappy sandals which allowed for plenty of adjustment, she assured me the heel was not hard to walk in but I doubted her. Once dressed, she brushed my hair and lacquered it in place. She complimented me on my nice long hair and smooth face, which had been a problem before as I had wanted to shave so I could prove my manhood, for once it was an asset. I thought that was it, but one last thing, she had a bag of make up but only suggested mascara and lipstick for now, that would be enough to high light the lips and eyes, and satisfy mother I was not being a tom boy or going all butch and lesbian. As if I could do either I argued
I might have felt a great cascade of emotion when I looked in a mirror, rather I saw me dressed as a girl and feeling awkward, I did look like a girl but I was still me. ‘Well Lauren what do you think?’ Jill asked, ‘odd I suppose, the clothes feel different, my lips taste, my eyes are sticking together and my feet are unsteady. Not a good start but I’ve known worse costumes in plays, so I will cope, lets go and see what mother thinks’. We found her preparing lunch, I thought there might be some great response on my entrance, a comment on my attire or feminine look, but she just seemed to accept this as normal, nothing new had happened, this was how things had always been, at least for her. She then offered us some of the meal and sat and talked about allsorts, but not about the absence of Lawrence. The whole experience felt peculiar, because I was dressed in unfamiliar clothes and my mother was relating to me as a daughter, which was different to being a son. Jill left after lunch, and I went to my room, the plan was to study a lot, which meant I would hide away for long periods, then in the evenings slip into the garage and change so I could visit friends as myself.
The studying went fine, when father came home we all ate together as normal, then I quietly went out to see Neil and go for a drink. Creeping back in at about eleven. It seemed to work fine. Jill rang in the morning to check up on me, I was already dressed as the day before, and asked for advice on mascara putting on and cleaning it off, as my pillow had black marks on it. The day was spent in my room only coming out to eat. But the following day Jill promised to call, and she did not say why except to help me get used to being Lauren.
First she was disappointed I was still in the same blouse and skirt, so she sorted through the clothes and hung them up insisting I try them all on when I have some free time, boy’s might wear one choice till it drops of their backs, girl’s do not. Next she asked if I had got any pants, of course not I replied, so she would take me shopping. I insisted on changing before I left, she called me a coward but accepted; going public was a daunting challenge.
Well I sneaked out past mother and made our get away in Jill’s car, soon arriving at the town centre where all the popular stores are. We parked and set off towards the ladies departments. It had been a long time since I had been in the ladies wear section of any shop, and now Jill was intent on buying clothes to fit me I felt everybody must be looking at me. As long as she doesn’t hold them up to me for size I will survive I thought. Mercifully Jill picked stuff so it looked as though it was for her, which is what I hoped people thought at least. The basket filled with packs of opaque tights, six pairs of pants (very soft and silky texture), three bras to match the pants and two panty girdles, which Jill said she would explain when we got home. Next she took me too Boots and the cosmetic counters, she discretely rubbed foundation on my hand, and choose a natural colour, followed by all kinds of products to apply to my face, then she picked up a sample scent bottle squirted it on my wrist and asked me to smell it, I blushed and she smelt it, ‘somebody might buy you that for Christmas’ I let that one sink in a moment before I said ‘eh’. We paid and left, but Jill was not finished, ‘one last shop, I guess you sleep nude’ I nodded ‘thought so, now imagine meeting your mother on the landing looking so unfemale, could be a shock’, ‘yes’ I said ‘so you need some night clothes don’t you’ she paused, ‘where is this leading?’ ‘That’s obvious I would have thought, you need a couple of nighties. Now what sort would you like to see a girl in? Plain T shirt, long cover all, satin and soft?’ my thinking was a little behind Jill’s and gave an honest answer when if I had thought I would probably gone for the T shirt, but described a long red satin nightie from a TV programme, and soon we were looking at the sexy going to bed stuff, Jill held one up to herself ‘do you like this one?’ I had gone sheepish, ‘fine I guess’ look for your size and we take a long one and a short one. ‘Who’s paying for all this?’ I enquired ‘your father of course, it’s his idea, so he has to fund it, I assume that’s all right with you?’ ‘Yes, fine just as long as you are not going to ask me to pay’
We got home while mother was out, so getting in was no problem. I went off to change in case mother returned while Jill made some lunch. I emptied all the bags and choose a white set of undies, padded the bra and pulled up the new tights; I picked up the first of the clothes Jill had hung up, a blue dress. Unfortunately I could not get the zip up my back so returned to Jill for advice. The hem was down at the calf and the knitted material fitted closely. After lunch I had a long lesson on dress sense, colours, and what to do with the cosmetics. The blue dress was removed, not with black tights I was told. There was a long black skirt and a pink top. The panty girdle was demonstrated on me as necessary with tight skirts. Then I learnt how to use the make up, Jill leaving me a book to study later, but it was not that different from stage make up, just more subtle and neater. Mother returned mid afternoon, and finding Jill still there asked if her and Bruce would like to have dinner, Jill thought it a wonderful idea.
With the full make up and a long skirt on I was feeling different and could sense myself behaving differently. I still retreated to my room to study until Bruce and father appeared.
As I heard Bruce arrive I realised he had not seen me dressed like this, and had a bout of nerves, but pulling myself together I went to face him, he had offered support after all, and I was acting a role. So I acted the role and went to greet him with a peck on the check, he froze for a moment ‘just acting’ I said and he relaxed. The evening went well, I got used to the long skirt, Bruce got used to calling me Lauren, and father seemed more relaxed than since my return. That night I dressed in the long nightie, but its satin texture was so sensual I had trouble relaxing and going to sleep.
I got up late and realised I could now move about the house without dressing, so ventured downstairs for breakfast, mother pleased to see me said nothing about the nightie except how comfortable it looked. I then choose to dress, then study for the rest of the day. I would always get concerned when I heard people knock on the door, but they were all for mother and I just wondered what she was telling them about her daughter when everybody knew I was a son.
I had a few days a relative calm, studying and going out at night. One day mother was telling a tale about a friend who she had been telling stories of my time at uni, and had been greatly offended when the friend had questioned my name, of course you mean Lawrence, was something like it. I envisaged more such awkward moments; just as long as I kept out of sight I would be fine.
The Christmas weekend arrived and Phillip arrived with Angela and their two kids. They stopped in the spare rooms, I was over my nervousness after meeting Bruce, and I had spoken to both of them on occasions, so I greeted them with a kiss, they complimented me on how good I looked, and the kids gave me some strange looks, but had been threatened not to say anything to Grandma. They had arrived late so it was the 23rd when we really saw each other, they both wanted to get me alone and see how I was, then ask how did it feel. When Jill and Bruce arrived I sensed a conspiracy between the women. It was not until Christmas Eve I found out their plans. For Christmas dinner mother always likes to have the family meal with everybody dressed up, I even had a suit I usually got out for this occasion, but I was assured this would not do this year. Jill would lend me a cocktail dress, and Angela would give me make over. I just said a resigned 'great'
They started mid morning, and had me standing in my undies feeling like I was being inspected. First I should immac my legs, and shave the bikini line, my arms were light enough so I left them. I washed my hair and Angela blow dried it into a much fuller style which needed gel to hold it, next they tried the dress for fit, it had tight sleeves a round neck and tight bodice in emerald green, then from the waist layers of light green net skirts which fell to below the knee. We all agreed it looked good except I was to big at the waist, no problem say Jill and pulls a corset out which she had needed the last time she had worn the dress. So with some complaining I was fastened into this thing, padding inserted and the dress tried on again. It fitted, next it was pointed out the corset had suspenders so Jill being prepared produced some stockings, even I could tell they were really good, they felt so sensual as I pulled them up my now smooth legs and fastened them on. I realised the whole thing had been planned and just asked them to get on with it, so they did. A pair of high heel sandals, a careful make up lesson, nails polished after being extended with falsies, last a necklace, wrist chain and a couple of rings. I was lead to a mirror and could not believe my eyes. I was used to seeing myself in a skirt, but now I saw a woman, a very attractive woman. ‘I think this will do for tomorrow, don’t you?’ ‘Easily, just remember the corset will be tight so eat small amounts, and do not do anything energetic’ was their joint response. Then I had to undress, Angela then smirked, ‘I’ve just thought, you keep on crossing lines, you wore a skirt, then you did your hair, then you got your own undies, now you’ve shaved your legs, and seen how great you can look, how’s about crossing another line and coming out with the four of us to the regular pub for our Christmas Eve drink?’ I was undoing the corset at the time, ‘you are joking, go out dressed like this, well not quite like this’ Jill smiled ‘go on it would be fun, we’ve never had a sister in law, and your brothers never had a chance to look after their little sister’ they watched for my response as I fastened my bra, ‘it’s me crossing these lines, not you, what if I’m recognised’ ‘ we’ll be with you, and we could go into town to escape the locals’ Angela finished with ‘think about it, and now you can wear natural tights, the blue dress will look good’. They left me to finish dressing, but I knew I would have to be sociable so went downstairs after a while.
They asked what I had decided, which attracted questions from Bruce, he thought it a good idea, it would prove to me how good I look, then Phillip was included, and somehow mother got to hear and added her encouragement, saying I had not been out much since getting home, and it was an excellent idea. Rather trapped how could I say no. We ate and the kids went to bed, then after much checking my appearance, I ventured out of the door. We sat men in the front me in the middle on the back, no escape I joked, but I recognised a familiarity of me sat with the girls, Bruce and Philip at the front, maybe there was a pattern. We entered a bar I had never been in but had a reputation for being lively, I was surrounded to give me support, and once inside drinking white wine I found it easy to talk about the usual family things, as well as mother and myself. They were genuinely interested in how I felt but we did not dwell on it, talking about everything and nothing in particular, as normal.
I could not believe how much I enjoyed myself, it was a real buzz to be dressed so unconventionally, and not be jeered as I had expected. And to be outside with the air on my shaved and tighted legs was totally new. We were not late home, but sat up with a drink until midnight knowing the kids would be up early. I could not wait to slip my nightie on and enjoy it’s satin softness, a suitable finish to a most exhilarating evening,
Like an excited child I woke early and lay awake for the youngsters to drag their parents out of bed. A family tradition is for the presents to be left in the living room by the fire, (who says Santa does not exist) then in the morning we get up and open them before we do anything else. Of course we watched the little ones rush in and excitedly rip into their gifts, then we more gracefully opened our gifts to one another. I had bought CDs or books as gifts, and people usually bought me something similar maybe a shirt from mother or a new pen. I was in for a surprise with every packet. Jill had bought a bottle of the scent she tried in Boots, Angela had bought a book, but one on make up styles and fashion tips, as well as how to be a model, my parents had bought me the same as they had bought Jill and Angela, jewellery a gold neck chain with a matching bracelet, we had a set each but I also had a signet ring engraved inside ‘to Lauren our special daughter’ they had guessed my size and got it right, I was completely taken aback.
I sat in my nightie, it covered my obviously male body, while I received gifts intended for a woman, my mind switched from pleasure to incongruity and back again many times, it was not until I dressed properly that I began to feel right with the ring and perfume.
The meal had been started very early and everything was prepared, but when my parents suggested going to church I adamantly refused, everybody else went but there was no way I could handle that situation, something about deceit or feeling naked before god. It gave me a little more time to get ready, as the green dress and all it’s accessories were difficult to unprepared fingers, but I was ready when they returned. The dress covering the corset and stockings, while the make up book had been followed carefully, then the chains and ring placed in their correct positions. I stood on my heels as I greeted them back home and served them with sherries or coke.
The day continued like so many other feasts, we ate and drank, played with the games, slept and chatted. Only I had the added interest of a skirt that looked great when I stood, but seemed to expand when I sat and all the net went upwards and having to brush it down, a diverting amusement to me, and at times the others. Eventually we all went to bed and slept well into the next day.
On Boxing Day there was an anticlimax, Jill and Angela both took their families to their parents, and left me with my parents. It was quiet and we cleared up the house together. I spent some time reading and taking in the books I had been given, with a little experimentation added for fun. Neil rang to see if I wanted to go out that evening, and I came back to the reality that I was only playing and accepted. In getting ready for the transformation into Lawrence, then smeaking out to the garage to change, I felt a tinge of deceit towards my mother, and a sadness that the fun of the holiday was over. But a drink with lads would be good. I spent the rest of the day at Neil’s or the pub, sneaking back in late, to avoid upsetting mother.
The rest of the winter break I expected to continue in the same vein, I would be Lauren at home to please mother, and Lawrence when out so as to be myself. I did take time off studying to check the books Angela had given me, and at times you might find me trying to simulate a walk or stance described, or playing with colours around my eyes, only in the interest of theatre and trying to play a proper part in the home, mother says she never brought me up to wear trousers, so why should I start now I was a student, being a student did not mean going scruffy, and in the situation I was in I obliged by doing as many girly things as I could.
There were two notable breaks from this norm. One fun, the other rather frightening. The fun one came at New Year, Jill and Bruce had tickets to a party and Jill was called in to cover at work, as nearly everybody else on the ward was sick. This created a situation where Bruce had a spare ticket and wanted to know if I would like to go, of course I did not, Jill offered to lend me the green dress, Bruce would be a gent and pay all night, the alternative was midnight with my parents and the TV. Bruce did not wait for an answer, rather he just told me to be ready in fifteen minutes and he would pick me up. Sure enough he was on time, then told mother why he was there, she said it was a wonderful idea. Rather unnerving me by coming to help me collect a few things, she wanted to know what I would be wearing, and gave me advise on how to behave. I bundled my bits into a bag and really wanted to sneak out and change but that was not going to happen with mother watching. I tried a couple of diversions but she did not take the hint, I was left with no choice, I had to step outside in the daylight, and travel in Bruce’s car to his house wearing a pink top and black skirt. Felling very exposed while outside I checked nobody was about, then made a dash for the car and sat well down in the car hoping the neighbours were not looking. Bruce was very kind and took a quiet route, but teased me about my performance; he tried to convince me I looked fine, I begged to differ.
Jill was going on duty at nine so was able to make sure I was perfect before she went. I wore the green dress with its tight bodice and layered net skirts again, I felt able to do my own make up, using bolder colours than Angela had done at Christmas, Jill styled my hair. Then with my jewellery in place I was ready, Bruce had a very smart suit on, looking a gentleman. So Jill saw us off at eight, and we drove a good half hour, most of which I spent keeping the skirt out of the driver’s way. Once there I realised this might be foolish, last time I had been out it was in a group, now I was alone with my brother. Nervously I followed him into the hotel reception and were shown to the function room, Bruce introduced me as his sister, Lauren, it sounded funny to hear it in these surroundings, but I let Bruce do the talking, it transpired he knew a few people there and chatted quite happily, while I said I had a sore throat and kept quiet. There was a buffet dinner, plenty of wine, then a dance with one or two silly games, at midnight we all cheered and sang, then carried on dancing. Most of the dancing was old time stuff to suit the majority; luckily we had all been taught waltzes etc as children so as long as I concentrated on being the woman we managed very well. Being held closely was a new experience; Bruce had somehow managed to switch his responses to me so I was a sister and not a brother. He held me close in the dances, would gently guide me with a hand on my waist as we went to dance, as a boy we hardly ever touched, I was surprised that he did it and that I liked the attention. About two I was getting tired, and the corset pinching, so we left. He was full of it all the way home, how nobody realised I was not a real sister, how well I danced, how good I looked. I tried to return compliments, but he made sure I took the credit. Then when we got home I had to ask him to help undo the dress, he then saw the corset and stockings, uttering something like ‘bugger me’ he just stood and stared, ‘if Jill had been dressed like that we would have been home long ago, do you realise how sexy you look, and that’s knowing the truth about my little brother’ I told him to leave it and help undo the corset. I think he went to bed a little shocked, I went to bed tired and wandering how I get home the next day.
Jill came home about ten, and we were just about getting up, ‘you should have borrowed a nightie’ Jill said as I came out of the bathroom in a dressing gown I had found. Then over breakfast Jill wanted to know every detail, she smiled as we talked, asking about some people I did not know, I felt worried enough to insist they would not say anything to anyone even to shock them. In the whole conversation one statement left it’s mark, Bruce said it but Jill agreed, ‘I never noticed before, but with no make up you still look feminine, you have mothers looks and build, I knew you were not a rugby player like me and Phil, but I could go as far as pretty’
Jill wanted some sleep, so I dressed and Bruce took me home hoping again the neighbours would not be looking.
The frightening event happened when I had relaxed into my regular routine, when the door rang I would make myself scarce, but if you relax too much you get caught out. It was the next-door neighbour Mrs Price, who caught me. I eating lunch engrossed in a book when they walked in, mother had meet her outside and invited her in, I was now unable to escape, especially when mother said ‘Lauren be a dear and put the kettle on’ I looked at Mrs Price and she at me, then smiled ‘nice to see you, Lauren’ I mumbled some response and went as bid. Mother left us together for a few minutes and Mrs Price approached me, ‘I wondered what your mother was saying, I thought she was confused, do I call you Lauren or Lawrence, I am right aren’t I’ I felt there was no other way but to be honest, I told her Lauren was for mother’s help, and that it was not for me. She explained how mother had been talking about a daughter, and that had confused most people, because everybody knew she had sons, and it was known Lawrence was about. She then wanted to know how mother was, and would her condition improve, she herself had noticed changes in her but did not know her well enough to understand the history of the problem. Then to my surprise she complimented me on my appearance, and told me she had not recognised me at first. I was flattered, but asked her to keep it a secret, which I think she did to her credit, she might be nosy, but not a gossip, thankfully.
That was a particularly worrying moment, and I must have gone white as Mrs Price found me, more worrying though was the fear of friends finding out about my new style of dress, they might not be so sympathetic towards the situation. I had a week left till term started and it seemed an age, I was hiding at home and not going out just in case someone said something, so it was a relief to leave home.
I left all the dresses and underwear behind, and thought of the ease life would offer being able to be Lawrence all the time, but I found myself thinking about the parties, and the textures and sensations of the clothes, and confused myself as I did not know how I should feel. I had done it for mother, and I hoped she would recover, but I had grown to be comfortable in the female role and now missed it. There was no outlet in the drama course; boys were not expected to play female roles as in all male schools, or centuries ago, so I lived as a man until Easter.
Easter and summer holidays
The return home was full of anxiety; I had spoken on the phone to family members and they told me mother still called me Lauren, but I was being optimistic and hoped to have things as they were. This hope was shattered when father picked me up from the station and asked if I would mind calling at Bruce’s so I could change before going home. Nothing had changed so I agreed, as long as he got a doctor to see mother. My life would be as restricted as it had been last holiday, but at least I would get the studying done. I was also anxious that the more I lived like this the more chance of another Mrs Price type incident happening, and that would not be good for anyone I felt. Even with all these negative sides to being at home I did like being with mother, she was lovely, and strangely I enjoyed the clothes and the role she was making me take on.
I was still relieved when we had a visit from a doctor, not our GP, but father said he was someone referred to by our GP. I accepted this and met the man in our home, he wished to see mother and talk to her without her feeling she was seeing a doctor, he would also like to see me and how she reacted to me. I felt this would help move things back to a normal life. He came and had lunch with us, spending time talking to mother. He found out things I never knew, there had been the a miscarriage of a girl, which would have been her first child, there after, with each son she had, she hoped to be a girl, and when I was not a girl, she could not handle it. By the time my memory starts she was over the depression, and I just accepted her the way she was. Now my physical presence had gone for a long enough period her reality now included a girl, somehow her mind had flipped me into what she hoped I had been. Once he had seen her he asked to see me alone, he explained the above, then asked how I felt. There were three options, one was to try and treat mother psychiatrically which would mean drugs and time at hospital for assessments, he was not confident mothers reality could be brought into agreement with mine, and the drugs may affect her in other ways. Option two is to be Lawrence, this would mean that she would reject me, I would not be able to see her as a son, as she would be hostile if I insisted on being known as her son, then I would be the one in need of counselling, and somewhere else to live. Option three he felt I had already taken, that was to meet her reality with a change of appearance by me, this I knew held risks for me, but he went over them again. As he recapped I did wander whose side he was on, we could drug mother, I could be rejected as a son, possibly permanently, or I could fit in with her reality, even if it is different to my reality. The choice was mine, if I left I see a counsellor, but if I stayed he could put me in touch with people used to helping cope with changing gender, but he always referred to me as Lauren and said he thought I was a girl when we first met, so I was not to dismiss the last option on the grounds of it not being physically practical. I could almost tell which choice he favoured, and he was not on Lawrence’s side.
A couple of days later I decided on shock treatment for mother, she saw me naked, I did it deliberately, but all she said was to comment on how little my breast had developed, and ignored my genitals, which is not hard as there is not much there anyway, but I hoped they might provoke a response something like ‘oh what is that? You are a boy’ but nothing happened, even physical truth could not invade her reality. It was the final hope I had of getting back to being a son, now I only had two choices, to leave or fit her image of me. I spent time with Bruce and Jill, and then went to see Phil and Angela, before going back to college. Nobody had an answer except, father would finance everything and they would accept my decision either way, but there was a feeling that as Lauren I would still be part of the complete family, as Lawrence somehow the family would be broken. So with all this I went back to my studies and hoped for someone else, or something else to precipitate an answer, instead of it all being down to me.
In looking for an answer I found a postponement, I was offered a summer job in a theatre near Phil’s which I took and stayed with them. But I did need to go home at the beginning of the holiday to drop my study things off, and accepted the now normal role swapping procedure. While I was there father said they felt it time to redecorate my room, as it was still a little boy’s room, the same as ten years ago. He said it would only be painted so if I did not like it I could easily repaint it. I agreed without thinking, so when I returned for a week before the second year started, I found a room painted in blue and yellow pastels, with matching drapes (no curtains), new bedding and a dressing table with a stool, by the side of a big cheval mirror. It was a girls room, if I had thought I would have seen it coming, but I did not object I had come to the acceptance that I wanted to be with my mother and if this was the way to do it without hurting her then I would be her little girl. How I would cope long term I was not sure as there was no way we could keep it secret forever. As if to underline that Mrs Price called round and I stayed instead of running upstairs, the future would have to be considered, but not yet I hoped.
Second Christmas holiday
I went away for a term of being a lad, little knowing what was brewing for me back at home. Father picked me up from the station in December, and we went to Bruce’s so I could change as I expected. It was the welcome at home, I knew about the decorating, but my room now had a fragrance to it, and an overall female feel to it, and it did not feel wrong which surprised me. A more worrying event happened after I left in the summer, Neil had called to borrow a book I had told him about, he asked for Lawrence first and was blanked by mother, when he mentioned this to his mother, she suggested asking for Lauren, and hey presto he was in, and she found him the book. The effect of this was felt when I met Neil a day after coming home, I had sneaked out and had been round at his house for a while when the subject came up. He caught me unawares with his questions, he wanted to know why I always came to his house or the pub, never inviting anyone home, why I was behaving oddly, and why he had had to refer to me as Lauren to get the book. This was the first time I had really been confronted by the dual role I now had. I must have blushed then gone white as I thought what to say deny or be honest. Neil had know me since juniors and he sensed my distress, we had always been a couple of gentle souls, not for the rough and tough, and we were used to being teased and bullied, but we understood each other, now that bond showed. He went to make a drink whilst he left me to rally my thoughts. Denial I discounted as he already had strong suspicions something was odd, so I went with can you keep a secret line, which I knew he could. I told him almost everything about mother, about the lines I had crossed on the way and a little of how I felt. He sat taking it all in prompting as necessary, then when he sensed I had finished he asked if he could call and meet Lauren. I was reluctant at first but he persuaded me to go home and he would call an hour later.
This was a worrying hour I had difficulty deciding what to wear and how much make up, in the end I choose the stretchy red tartan skirt and polo jumper with light make up but enough to emphasise the fact there was make up, and a pair of heeled courts. I was still fussing when he called, he asked for Lauren, mother said how nice it was to see him and why did he not come round any more, then she called me, I met him in the hall and took him to the lounge. His face was a picture, total disbelief, he swore if he had seen me outside he would not have recognised me. Later I decided to show him my newly decorated room for his opinion, he approved of the colours and said it suited me, and then fortunately he had to go. That was enough for one day, it had been quite stressful, and I retreated to my room to find some peace.
Neil was now full of his new found secret, he rang and asked if he could call, he wanted to ask me some questions. I could not retreat now and waited for him with a sinking heart wandering where this might lead, and just when I thought I had got me head sorted out as well.
What he wanted was to see if his eyes had let him down, but he was again stunned (his word) at how good I looked, then he wanted to know everything about how the clothes felt, how I felt, how the role felt, how long the secret double life would continue, finally he asked if I was comfortable and enjoying the role. I tried to be honest as far as I understood the answers myself. Then he said he wanted to prove to me how good I looked, that I was not a grotesque man in a skirt, he insisted he call that evening to take me into town to a bar both of us knew but were not known in. I wished I could have said no, but he was so keen and I wanted to know if I was able to go out dressed. I spent ages dressing; I was immaculate having done everything I could think of at least once. He pulled up in his mother’s car, and had made an effort himself, it took a tremendous effort to leave the front door as I was shaking so much, but his enthusiasm never waned, he took my arm and lead me to the car, I remembered the times out with my brothers and knew I had coped well then, so I could again. The cold air was fresh on my legs making the car very cosy, when we arrived after a halfhearted attempt to change Neil’s mind we left the car and walked to the bar. I said if anyone as much as stares at me I was off, we found a quiet corner, Neil bought us drinks and I waited to be stared at or someone to make a comment. After an hour I was enticed out of the corner and into another bar, then into a club where we could dance but I had difficulty thinking of dancing with my best friend. In the end we left for home, Neil had won, people had looked but no more than Neil or I looked at other people, Neil insisted people always look at a pretty girl so it would be strange if nobody had looked, and I agreed he was right, for the first time accepting I looked like a pretty girl, that was another line crossed, acceptance that I looked fine and not a freak.
The week before Christmas was a usual mix of sneaking out to do shopping or see friends, but now Neil knew he would call, and twice enticed me out in the evening for another drink in town. The buzz from going out with Neil was very nice, and Neil seemed to like the recklessness of being with me, I suppose we liked being different and daring people to challenge us, except the last thing we wanted was to be challenged, if we were ever suspected we would have run a mile.
As the family would gather for Christmas day I did wonder what would happen when Phil and Angela arrived, they had not seen me dressed for a year, how would they take it? I need not have worried, they could see mother was well, and upon questioning realised I was fine as well. We decided to go out again on Christmas Eve only after Neil called he got invited as well. It was amusing to see his face when my niece called me auntie Lauren.
I had bought a pink skirt and top from a catalogue and had saved them for this outing, along with a ¾ coat I felt wonderful, the first clothes I had bought for myself, Angela had expected to give me help but she was pleased to see I had got to know a lot in the year, her only suggestion was to pluck my eyebrows thinner, which I promised to consider. Once we were all ready we left for town, I had been in a few of the bars and pubs now so felt easy walking around, what was interesting was how Neil behaved when I was with Jill and Angela, I had not noticed but I played a more feminine role when I was with them. I was copying and being encouraged, and my brothers being so masculine took on Neil as a bloke, this made us respond to each other differently from before when it was two friends out for a drink, Neil felt he ought to have held my hand or something like my brothers were with their wives, and when we went to a club we both were left as they went to dance, and we felt we should be a couple. At the time it felt odd stood together looking like we ought to be much closer and something that we were not.
Well the Christmas Day meal was as much fun as usual, Jill leant me her green dress once more, and I tried to do it justice. I hoped to give more appropriate gifts this year; I bought silk dressing gowns for Jill and Angela, and silly ties for my brothers. In return they gave me some surprising prosthetic breasts and some new bras and pants to go with them. Angela in particular wanted to see how they looked and I promised to try them later. So after we had eaten and tidied up, as some went for a walk or fell asleep, I went upstairs to change, I tried to be alone but Angela and Jill noticed I was missing and came to find me undressed and reading the instructions. They had adhesive pads or a type of superglue to stick them to me so it was a case of working out where to place them, how long I wanted them to stay on for, and how I should remove them. After much playing around they were stuck in place and I could feel their weight pulling on my chest, I quickly refastened the corset to find they are much larger than the foam shapes I had been using, they were in fact a size D, the argument being they were wanting to give me as good a figure as possible and a good chest is important. They certainly filled out the dress an added to the visual effect of my narrow waist.
Neil came round in the evening with a gift, he was a picture when he saw me, eyes nearly popping out, and when Jill told him I had stockings on as well it was not hard to see he was getting excited. Very nervously now he gave me the gift, I had only given him a CD, he gave me the sort of thing you give girlfriends, matching camisole and French knickers, we both blushed and he said it seemed like a good idea at the time, and he meant nothing by it just fun. We invited him in and had an enjoyable evening playing with the kid’s games. When we finally went to bed, I was faced with what to do with the breasts, and because I would be putting them back on in the morning I felt it easier to sleep with them on, as long as I did not sleep on my face and squash them I should be alright. So with a nightie now filled at the front I went to sleep feeling the unsupported weight of breasts for the first time.
On Boxing Day, before Phil left for Angela’s parents, we went for a walk with his kids; I was even brave enough to go out as Lauren. As we ambled about the paths he opened a new can of worms, he asked how I thought Neil looked at me, was I attracted by men, and was he right in thinking I was becoming more Lauren than Lawrence. I hesitated on all the questions but they did crystallize in my mind some things that I had started to think about myself. I kept myself busy the rest of the day, and when Neil called told him I was busy, really just avoiding him.
I had another day of introflection, then on the following day Jill asked me to go to the shops with her, I felt it would be fun and reckless, she was a little surprised when I was ready to go in a dress, but she hardly turned a hair and drove us to a shopping mall some distance away. This was a thrill, we went into shops, I looked at clothes we had lunch, generally I did all the things I hated doing with girls, but now I enjoyed it. I did not have the nerve to buy anything but the challenge was set to do so and soon.
When we got back I returned Neil’s call, I felt I wanted to know how we felt about each other. He came round and the talk got round to what I was wearing, and what he thought would be nice, I boiled it down to short and sexy, fairly typical male I thought, but on your best friend, did he really want to see me in that style? I suggested we go out for a drink later on, sent him on his way, then after dinner found the shortest skirt and tightest top which was not hard now with a pair of whoppers on my chest, the highest heels and boldest make up, I would have worn stockings but they came to low for modesty, all covered up with the coat I was ready to test his response. I kept the coat fastened until we were in a bar, he became all protective when I opened the front and he saw how much leg was on show, I was a little surprised at myself but it was for his benefit I told myself. When I took the coat off later he leant over and whispered ‘I’ve never been seen with anybody so good looking, I cannot believe it, if only you were my girlfriend’ I did not respond but kept it in mind for future reference.
The next day I spoke to Jill, I could think of no one else to confide in, telling her of the previous nights events and responses, and asked if she thought Neil fancied me, the reply was unexpected, how would I feel if he did fancy me, something I had not considered was how I felt about being in a sexual relationship, I only looked at how people saw me. How did I see Neil, or any blokes for that matter? Then Jill asked if I would like to go to a New Year dance with them, I said it would be nice, then she suggested I needed a partner, as she was definitely going with Bruce this time, I dithered and she said she would ring Neil for me, and ring me with the answer, fifteen minutes later she rang to say she had two tickets, and Neil would pick me about eight on the evening.
I hardly had time to reflect on the implications, when mother appeared at my door, ‘Jill tells me you are going to a dance, I would like to treat you for being so good to me, please come shopping with me this afternoon.’ I had two days to the party and maybe she wanted to buy something special.
My assumption was right, there is a shop she particularly likes to buy from, but they also have an agency, so she had rung in advance to see if they had anything suitable for her daughter, this fortunately forewarned the owner who knew her well, and had noticed how the offspring had changed. I was greeted with courtesy, and a whispered word of understanding, ‘don’t worry we have sussed out the situation, and will kept you private’ I thanked them and we were lead into room at the back. The whole experience was thrilling, the owner kept bringing clothes, encouraging me to try them on, offering an opinion on them all, but most of all she made me feel special, I know she was after a sale but that did not detract from the fun. I finally picked a yellowy gold dress; it had a high neck, no sleeves, built in bra cups, a bare back from the collar to the top of my arse crack, a skirt that was tight around the hips but long with a split up the front. We then went looking for shoes and a clutch bag, I was nervous as we entered the wide world, but mother’s confidence did for both of us. She initially wanted to find gold but we settled for white.
All done and tired from walking about in high heels for so long we headed home. We hung the dress up, and discussed make up and hair styles, not something a son usually talks with his mother about, she went of to phone someone, returning saying tomorrow would be busy, her salon could squeeze us in. This meant little at the time but by the following evening would have made a dramatic change to the future.
Almost as soon as I woke I looked at the dress, I had it for a week and could not wait for New Year’s Eve. After lunch mother drove us a few miles to her salon, they knew her well, and when she introduced me I knew they knew the situation. Mother wanted her hair washed and styled, but she had more plans for me, my hair had not been cut for a year and just reached my shoulders, her and Sarah the stylist talked about me rather than with me, mother said it was a shame my hair was short and non descript brown, Sarah offered to change all that if we wanted, she showed colour charts, then photos of models, I was taken with a pretty picture of a long bob in a very light brown, not thinking Sarah would say if you have the time, then we can do that. In disbelief I looked back, mother just told her we had plenty of time. My head was fussed over for ages, the hair extended and recoloured, then styled. And while all this was going on, a girl called Helen came to do my nails, but with having to keep my head still for along time, it was some time and four fingers into the job before I saw she was adding acrylic nails that were at least double my normal cut length, but it was a bit late to object and the pampering was nice. After hours we emerged, my hair now fell both sides of my shoulders brushing the top of the breasts and moving very freely, my nails were long and polished pink, becoming more obvious to me as they stopped my fingertips touching things I expected to touch.
Father was at home when we returned, with a big grin on his face, ‘Lauren, I hope you don’t mind I’ve booked seats at the theatre’ mother did not wait for my answer, just told him to prepare some food because we were off to get ready. She disappeared into her bedroom, and then called me to ask which dress to choose, she had three evening dresses, we picked a full long blue dress that swished a lot. Then she told me to go and get ready but to leave the dress off just in case I spilt something on it. With great care I did my face, made sure the breasts were secure, and taped myself backwards and used a panty girdle for extra concealment. When it came to the dress itself I had to ask for assistance as the nails got in the way, the buckles on the sandals only just working for me. Father had his best suit on and complimented us both before escorting us to the car and onto the theatre. The play was nothing special, and not one I would have gone to from choice, but the exhilaration of being out in such a lovely dress with gorgeous hair, and feeling the warmth from my parents. We went to a small wine bar for supper after and enjoyed every minute of being so glamorous. The anticlimax was getting home and having to undress and trying to sleep after such a high, but I did eventually.
Late next morning I was having breakfast in my nightie, as I had become accustomed to doing, when father appeared, he was usually gone to work and he had never seen me just up before. ‘Last night was good wasn’t it?’ I agreed, then he continued ‘you enjoyed yourself didn’t you?’ not waiting for a reply ‘you seem to be less hostile to being a girl now, I guess you did not realize how pretty you were’ he paused ‘ I can afford to spoil you, you know. If you want I could give you a clothes allowance, and pay for the other things which you never had to think about as a boy, but now have to be considered.’ all I could think to say was ‘that would be kind’ but somewhere at the back of my mind I felt I was being manoeuvred by him, I just was not sure if I should let him.
Neil called later, he loved the hair and the nails, and my eyebrows had had a few more hair extracted. I enjoyed telling him about the theatre, and the new dress. The conversation moved on, and then out of the blue he said ‘you will have trouble going to the pub with those nails and long hair you know’. In all the excitement I had forgotten the implications for the future, I acknowledged that if I went out now I really had to do it as a girl, then he listed the things which had changed, hair, nails, eyebrows, shaved legs and arms, he missed one thing, breasts, he did not understand so I undid my blouse, his eyes were starting to stare, then when I undid the bra I could almost see his trousers move, ‘see they are fixed, it takes a few days to come off easily’. He was not really listening to me, ‘do you wear knickers as well’ I asked him if he thought anything else would do. ‘You just don’t realize how splendid you look,’ I blushed ‘are you going to stay like this for good then, or just for now?’ I asked him which he would prefer, he confessed that Lawrence was his best mate, but as Lauren it was getting difficult to think of me as a friend like Lawrence, he was being confused by having the image of a girl he would really fancy if she was available and real. We then circled round the subject of why he had not really had a girlfriend, and why I had split up with mine, and onto sexuality. We were very honest with each other, but I found myself thinking as Lawrence but behaving like Lauren, now I was confused. We concluded nothing, there was no point at which we said ‘that’s how it is’ rather we would talk as though we meant somebody else, the ‘I have a friend’ sort of statements. After an afternoon of being honest, but not understanding anything more about each other, or ourselves, we parted. Neil said he should be able borrow his father’s Mercedes which would compliment the beauty I would become, ‘can’t turn up in an old banger can we’ he insisted.
New Years Eve I was so excited, I wished Neil or myself had made our minds up as to how we felt about each other, or maybe we were avoiding rejection by not actually taking the friendship into new areas. Anyway besides wanting Neil to take the lead, I had a day of making sure I was perfect. It started in earnest in the afternoon, mother styled my hair, it was so soothing to have my hair brushed, I was shaved and thoroughly checked, the breasts were checked, and glue packed just in case. Whilst I was swaning around in just bra’n pants and a dressing gown, the belt became untied in front of father, and like a girl I hide myself, as Lawrence I never bothered to be modest, and as I sat down later I considered how this role was taking over. The response had been instinctive not considered in any way. I could not decide if that was a good thing or not. Well after all the water treatments it was time for make up, I took great care to get everything perfect, the eyes, the lips, the blusher, then I recoated the nails. Only the dress left, but that would wait until the last minute if I was sensible, but I was so excited I had to wear it. I removed my underwear, and was looking for clean knickers when I saw Neil’s present and slipped on the French knickers, then I stepped into the dress fastened the collar behind my neck, rearranged my breasts and slipped on the shoes. I was ready, the feel of the dress against my skin, the legs in particular was lovely, and I could feel the breasts moving about in a most natural way, I presented myself to mother who approved greatly, leading me into her bedroom, ‘here this is for you’ she passed me a ring ‘it was your grandmother’s’ I looked at it, there were two really, matching wedding and engagement rings, she pushed them onto my right hand, then we admired them. ‘Those are to keep, but you can borrow these and gave me a handful of gold bracelets, and a gold ladies watch. I put them all on and played with the bracelets, they seemed to be constantly moving there were so many of them.
I sat and waited for at least an hour but he was not late, and arrived in the Mercedes and wearing a suit. I met him at the door to stop mother inviting him in, he grinned ‘your carriage awaits Cinderella, you shall go to the ball’ I smiled back ‘you look smart’ ‘not as good as you, you are beautiful’ he replied. I kissed his cheek ‘thank you’ I whispered in his ear. I picked up my coat and bag and we left.
We met Jill and Bruce in the function room, they had saved us seats, Jill was lovely in the green dress I had borrowed last year, ‘Bruce insisted, he said something about seeing this dress in a new light’ Jill told me later, I asked if she had the corset and stockings on and smiled. I spent plenty of time with Jill because I would not go to the toilets alone. It was at such a moment Jill asked how Neil and I were getting on, I shrugged, she said she had been watching him and he could not take his eyes of me, I suggested she was mistaken but I knew she was not. We all danced and ate and drank till we had had enough, I danced with Neil and Bruce, but the way they held me was different, Bruce held me as a dance partner, Neil held me just that little bit closer, and I him. A few days later Neil told me Bruce had told him he saw nothing wrong in us being together, in a way that meant he had no prejudice about my new look, or us having a relationship, and that he should get on with it before some one else moves in. I could guess when this happened because he started leading me to the dancefloor by holding my hand, and the holds got closer. At something like two o clock, we made our excuses and left, I linked his arm and as soon as we were out of sight I kissed him, and I don’t know how but we made the kiss a real one with real passion, like I had never kissed before, he responded and we held each other tight. A magical moment. As we held one another I could feel my crutch straining at it’s controlling tapes, I was used to it getting excited when I had worn certain things before, or even in exciting situations, but know the tape was being well tested, I just hoped it held and did not embarrass me with an unsightly bulge. I pulled away not sure if this should be happening, Neil took my hand and walked me to the car, he opened my door like a gent then got in his side. We drove back in silence, the shock of what we had done stunning us both. As we neared home I had to say something, ‘what do we do now?’ I asked, his hand came across touching mine, ‘would you like to try again?’ he was not answering but getting agitated. ‘Stop the car’ I commanded, he stopped safely then I leant over and kissed him, again there was the same electric between us. I pulled back ‘I think that answers our questions’ he pulled me back to himself ‘I think it does, you keep on being Lauren, that will suit me just fine.’ Holding each other we relaxed, ‘lets go home’ he suggested, ‘whose?’ I asked ‘there’s nobody home at mine’ he offered ‘lets go there then’.
Within minutes we were on the drive, and we entered like teenagers trying not to let go of the other. ‘Do you want a drink?’ ‘I think a big vodka if you are having one’. We eventually disentangled our bodies a couple of hours later, the tape had survived, as had the dress. But Neil had a tell tale damp patch on his trousers to let me know he had enjoyed himself. He then walked me home, passing several people on the own way home from their parties, nobody gave us a look, except one friend who acknowledged Neil but not me, as he had not recognised me. After a long doorstep kiss I went to bed very excited but exhausted.
About midday Jill called round, she wanted to know what happened, and I wanted to know if the green dress was a hit. We told each other everything, then very directly she asked if I was a virgin, I blushed, she guessed I was, and Neil, I did not know for sure but I thought not. Then she pointed out that for now I would have to remain a girl, a boy would not have long polished nails, breasts, narrow eye brows or such a long hair cut, some things I could cover up but not those, so my sneaking off times were over for now. Jill then hoped I would make the most of my new identity, buy clothes, go out, enjoy the new identity, and maybe see how Neil wants it to go. I assured her that the amount of effort that had gone into making me look like this, I was not going to throw it away at least until the new term started.
It was raining so I decided to make my first walk from home alone with the aid of an umbrella to hide behind. I would walk to Neil’s then walk back, not to far, nice and easy. There was no problem, I turned the umbrella towards anyone and was soon at the door. He was certainly pleased and surprised to see me, though we started off as if nothing had happened the previous night, we sat with a coffee and talked until I had to come to the point, ‘I like being Lauren, and until the end of the holiday shall look like this, now what I would like to know is, do you want to be a part of it?’ he looked back at me a little stunned ‘I am surprised you need to ask after last night, I was hanging back so as not to come on strong and upset you, this is really all new to both us’. So we agreed to be honest with each other, and free to ask questions. So started a long evening, I wanted to know if he had sexual experience, what sort of clothes he liked me in, what sort of things we could do together, or where we could go. He wanted to know how I felt, how far I would go sexually, what sort of clothes I would wear, how public I dared to go.
We spent three happy days while his parents were away, going round the shops, visiting bars in town, nothing too close, and watching television until late then walking home. If we bought some clothes he always wanted me to show him when we got home, I did not mind because I would not use the changing rooms, and having Neil there meant he could do the talking. We bought mainly underwear, but one skirt (the shortest Neil could find), a fresh nightie, and a pair of trousers, and very high stilettos, again to please Neil. Money was no object, father seemed keen to be generous so I took it and enjoyed it.
The sexual side developed as well as the wardrobe, on the day we bought the mini and the stilettos, I promised to wear them that evening, he dropped me at home to get ready, I found his camisole and knickers, and with stockings expected to please him. We went to a bar then a club, we danced a little but the shoes were a bit too much and I was refusing to take my coat off as the skirt barely covered the stocking tops. We ended up back at his house, watching late TV and entwining our bodies. When he started to undress me, the blouse first then the skirt, not to be out done I insisted he do the same, then we really got excited. It was apparent he was enjoying himself, and I still am not sure why but in the excitement, I knelt before him and took his dick out, it did not take long for him to cum and then sink to the floor. As we lay on the floor together I had a definite sense of crossing one of those lines, I just wondered how he could satisfy my own aching genitals and me.
I also had a few public outings in this period, I had grown comfortable walking to Neil’s, I had met Mrs Price, but everything else was in secret. One day I added another person to that list, Neil’s mother, she came home unexpectedly and found me drinking a coffee in her kitchen, after a careful look, more an examination, she asked my name, I said Lauren, Neil came to my defence and explained who I was, then she sat down and wanted to know how mother was. Then asked about how I coped, and how pleased she was Neil could still see me as a friend. This did make it possible for me not to be secretive with Neil’s parents, his father seemed sceptical about me though. I got braver about being out, though I never went out to be seen. There were times when I passed people I knew, had a worried moment, then a flush of calm as they went past.
And so the holiday continued, some trips out, time spent with Neil or at Jill’s, but mostly it was my studies that benefited, my room being a most comfortable place. Mid January I had a final fling before going back to uni, I went for a day in town with Jill and mother, then in the evening I wore a tight skirt and short top to excite Neil, and we had a night in a club dancing and being affectionate. It all ended to soon, and in the morning had to get ready to return to being a bloke, the nails came off, the breasts removed, I found the jeans and jumper, and was thinking of going to a barber but decided the hair was far to good to loose, so I put it in a pony tail and hoped nobody would make a big thing about it. Then with my bags packed I was ready to travel, it just felt so strange to be dressed that way after so many weeks in a skirt.
One big plus to returning to my course was that, the terms unit was on costume and design, needless to say I was far more interested now than I was at the beginning of the course, and took great interest in the making, as well as the great variety of styles. The end unit assessment being to select styles suitable for three different plays, a pantomime, a period play, and a futuristic theme. All were fun to do and I enjoyed it immensely, such a pity it was only a small part of the work. In the final year I can spend more time on it I was told, I hoped they were right.
Easter holidays
The Easter holidays had a surprise, as all my returns home seem to have been. This time after father had picked me up at the station, and I had changed he locked my bag in the boot, and dropped the surprise, mother had been tidying my room and found some male clothes, this had lead to difficult times, so he had been in and cleared the room, leaving only Lauren’s clothes. How could I sneak out, and meet anyone but Neil. I felt trapped, and asked if I could hide some clothes in the shed. He said he did not want to run the risk of mother finding anything again, and besides after the last holiday I would have no problems going anywhere as Lauren. Once home I quickly retreated to my room to find it exactly as I was told, every trace of Lawrence had been removed.
Next morning I rang Jill for her advise, she was surprised at their actions, but suggested I take advantage and ask for a bigger clothes allowance, a hair appointment and the use of a car. Then take some lessons in deportment and voice coaching, show them they are not overpowering you, but meeting the challenge. I made a lame attempt to say I hoped mother would soon have me back as a son, but I was sat in a very nice nightie at the time and I did not really convince myself.
I asked mother if I could use the car, to my surprise she agreed, then I asked if I should have my hair trimmed, and she rang the salon to make an appointment for that afternoon. I almost knew that if I asked for an allowance, father would say yes. So I went for my appointment and enjoyed the pampering of a salon. Then once home I filed my nails that had now grown to a length that was unusual for a boy. I had already sugared my limbs and glued the breasts onto my chest. I was now ready for the finishing touches, eyebrow plucking and full make up, and then it was of to see Neil. What took me unawares was how much I relaxed, and felt comfortable once I had finished dressing. I left my legs bare and wore a long soft skirt so I could feel the texture on them.
I was feeling quite excited about meeting Neil and resuming our friendship, but it took a while before he grasped the situation that I was enjoying myself, and that due to circumstances beyond my control, I was not able to go out as Lawrence during this break. Full of enthusiasm I suggested we go out and visit places taking risks, but I wanted to see how well I could be accepted, at the back of my mind I was thinking if mother did not improve, could I live like this all the time, and lurking deeper in my mind was the thought that even if mother did want a son back, would I be happy to give that son back to her.
We sat around and suggested places to go and things to do. Neil’s ideas got dafter as we continued. By the end we had several easy ones, like going for a walk at different locations, such as parks, shops, etc. there were a few evening places, see a film, watch sport, obviously we could go to pubs as we already had, but how about a country pub or a bar meal, somewhere we never thought of going before. The daftest was going swimming, I just felt the costume would be too revealing. The most daring was to visit the local pub and meet our friends, Neil had said nothing up to now, and maybe he could feel the temperature before I went in. But one we both fancied and were keen to do was to go away for a weekend.
I put the idea to father as a learning exercise, it would help me to get used to being Lauren away from home, which would make it easier to move about if I had to dress as a girl all the time. Father seemed surprisingly enthusiastic about the last comment, not only did he offer to pay for an Easter break holiday, he made a booking, but also asked if I would go to see the doctor who had seen mother before. He had been to see her since and had said he saw no change in her, and had asked how I was coping.
Two days later, father drove round to his surgery, I was dressed as Lauren, but there was no choice really. The doctor saw us both then asked father to leave. He took some blood, asked questions about how I felt I was coping, he seemed pleased with my appearance, and was most interested about Neil. He had a challenge to set me, in that if I wanted to take the role further then I would have to go completely public and face the possible problems it may create. On the other hand he could suggest various people who could help teach me to act femininely. As a drama student I thought I was doing quite well, but a second opinion would not do any harm. He asked me to go back in a week to discuss the blood results and possible feed back from the specialists.
The specialists were interesting; the voice coach was impressed with how I controlled my speech with only a little advice. A woman I went to see about deportment was something of a perfectionist, but my time with her though not fun was useful. I was shown how to walk, stand; sit, along with how to hold my head and where my hands went. She insisted I come back a week later so she could see how I had improved.
The doctor had spoken to several people when I saw him next, besides those I had seen, who had given positive reports, both saying they thought I could live as a woman if handled properly. The blood test confirmed a low hormone level, and was asked if I would consider hormone supplements which would help raise my voice and slow beard growth, the thought of not shaving, even the little I did, was very appealing. I left with a book he thought would be useful, as it explained the biology of what was being proposed. He also advised taking counselling, which he would sort out, and finding out as much as I could before I made my final choice.
All this fell into the background as the weekend away approached. Neil was possibly as excited as I was; he wanted to know how I would dress, and what sort of things we should do. We agreed on a play and a museum (he was doing history) that very conveniently had a fashion and costume section. Come the morning I took great care to shave all over, secure the breasts and tape the male bits away neatly. I carefully styled my hair so it looked like a star on the back of my head, made up, then choose stockings and satin undies, a nice new dress which had ¾ sleeves, a round neck and knee length hem seemed appealing in deep pink, with black shoes I was ready. I packed enough for a week because I could not decide what would be best. Neil called looking smart and showing off the car keys, somehow he had persuaded his dad to lend him the merc instead of his mum’s fiesta. And so the weekend set off well. We drove too York had lunch, looked around then found the hotel, father had booked it through his business but in Neil’s name. It would have been difficult to explain that I was Mr Allan, or at least his son. The room was lovely not too cramped, a nice comfy couch, big bed and en suite. We looked at each other then the bed, asked who’s idea that was, then Neil pointed out that I was wearing my grandmother’s rings on my left third finger, they assume we are married. There was a twinkle in our eyes at that thought, and all evening made comments, and addressed each other with married type words, Mrs Philip was Neil’s favourite. The theatre was good, though Neil’s hand on my thigh was an endless distraction. After a late drink we went to the hotel, I made it to the bathroom and without thinking cleaned myself up put on a nightie (short black) and wandered back into the bedroom. I am slow at times but it was when Neil called me Mrs Lauren Philip as he invited me to join him in bed, that I realised we would sleep together. It started as a cuddle but once I had recognised the situation and was being encouraged in the right way, it was not long before I was allowing Neil to enter me and be my first. I slept badly as I had not come so I leaked in my sleep, making my side damp. I resolved next to come myself before sleeping.
The weekend went too quickly, we visited a museum, the pictures, a theatre and many cafes. We also spent a lot of time in bed. We became sex mad, morning and night, even in the day when I found Neil erect we found a quiet place and I wanked him. I also found that Neil could kiss my end and get me there, or I went to the toilet for relief. Clothes choice was not a problem, just choose the tart look and Neil was happy, though I did go smart to the theatre.
The weekend was over and we were driving home too soon we felt, but stopped in a car park for a last fumble, before we had to start being careful.
The summer term was upon me quickly, and another unit of the course to do. But this term we choose our third year topic, where we specialise in one aspect of drama. I was hoping not to appear over eager to do the costume as it is normally a girl’s topic, and you spend a lot of time with the textile art groups, another mainly female group. But in a discussion in the tutor group I said I was undecided, and three of the group told me I had to do the costume, the tutor agreed that I had done well in that unit and I seemed to have a flair there. Later in the union when I had had a drink I asked Mat and Sara why they thought I should do costume. Sara took my hand, looked at my nails then at me, ‘sometimes it is nice to have a man who understands how an outfit can change the look, and you do it with yourself anyway’ I replied with an oh, she continued ‘when you started you were a dull boy, now your style is quite outlandish, the nails, then there was the long hair a bit ago, and you never wear the usual student clothes’ I took my hand away and had a drink, ‘besides me and Jo want to do costume and we reckon it would be fun working with you, you don’t seem to have boundaries, we reckon you would wear anything if the time was right, or suggest a braver idea than the expected’. ‘Is that a compliment?’ I asked. ‘Take it as you like, but please do the costume with us, it will be a fun year’
And so I put my name down for costume design, and spent the next week spending my allowance on female cut trousers, unisex tops which had a more feminine look. If I was seen as eccentric, then I might as well live up too it, and dress in an androgynous style to suit myself.
Last summer holiday
After the exams, and the play we had to produce. The summer was our own, I meet father at Jill’s so I could change before going home. Jill did comment on how my trousers had a flat front, then smiled saying it was none of her business, and wished me a good holiday. Everything was normal, all traces of Lawrence were being eliminated, photos had gone, clothes all gone, I even found some little girls clothes that mother had bought hoping I would be a girl. The first things I wanted to do at the start was to confirm my female identity, so I booked at the salon for my hair to be done. Clair did the roots and gave it body with a soft perm. Then with all the feminising touches such as skirts, breasts, heels, and make up I felt more comfortable in the home.
Father and the doctor had sorted out some speech coaching, and deportment sessions, which were fun and though I felt accomplished did learn new tricks, the thing was to remember them and apply them. I also got a job delivering leaflets, I could remain anonymous, while out and avoid to many challenging times. I could also wear pumps, shorts or loose skirts allowing the summer breeze to caress my legs. Neil got a job in a museum for the summer, which meant we did not see much of each other. A shame as we had got so far in our relationship, but then on the days we did meet up neither of us seemed confident to rekindle any passion. Somehow we had blown ourselves out in a flurry of activity during the last hoilday and now could not find it again.
Autumn term
The best thing about the summer was the end, and I started my third year. Sara and Jo found me to let me know the three of us were doing costume design and wardrobe, but commented approvingly on my hair, the perm obviously had not grown out and asked what I had been doing over the holiday. I could only smile, I was not about to tell them I had had a great time living as a girl called Lauren, but some how I sensed she guessed part of it.
The term was spent designing and making costumes for a pantomime, cat and dog outfits and ugly sisters, all very traditional but we had fun with the students who were to be the sisters. My favourite was the wedding dress; Jo bought one from a charity shop and adapted it for quick changes. The material was satin and lace there was a pang of jealousy as she tried it on and I remembered some of the dresses I had worn and felt uncomfortable now being unable to have the choice of trousers or skirts.
Events conspired to change that before the term was over. One afternoon we were busy drinking coffee in the workshop, I think we were making a cat outfit, when the fact that “Rocky horror show” was on in town and I had never seen it, I knew what it was about, and about the childish antics that go with it, the rice and water throwing, not to mention the dressing up. Sara rang and got tickets for the following night. Then Jo started to persuade Sara they should dress as girls in 50s style clothes. Sara was not sure and made uncertain sounds. Jo then turned her attention on me, how’s about Frankenfurter fishnets and a basque, I was tempted but tried to appear diffident. No she agreed, I think you could be less obvious than that, Sara and I looked questioningly at her, then she explained how much fun it would be if I took a less predictable character in terms of what was expected, yes we said, she disappeared into the rows of costumes and came back with a disc skirt on, and proceeded to point out how we could put our hair in bunches, and look all sweet and innocent, and she knew there were three outfits like she had on. Sara and I looked at each other first then at Jo, who was all excited about her idea telling us what fun it would be to go so outrageously dressed. Then Sara turned to me and related a conversation she and Jo had had the week before, they had been discussing why they got on with me, and how feminine I was in appearance and manner, then looked at me very carefully, long permed hair, narrow eyebrows, smooth face, long nails, that nice ring, an heirloom I put in, and where is the lunch pack? It’s the way I like to look I lamely replied asking what was wrong in that, nothing she replied but if you go with Jo’s idea then I shall also. Jo was now given new enthusiasm and kept on at me telling me how much fun it would be, even if I had not wanted to go along with the idea I am sure she would have worn me down. Having agreed she disappeared to find three outfits, then started asking about make up, and discussing rather inappropriately with Sara about what I should do, I played it innocent, just suggesting I had picked up a lot from the course. We went back to the project in hand eventually and the subject died away. That is until the next day, we meet after lunch to continue the costume, but Sara was showing signs of cold feet, and not wishing to miss this opportunity told her if I was doing it then she was, adding I had shaved my legs for nothing if we renege. Let’s see, ohh that is good, arms as well, yes, ohh. Jo went to sort out the skirts; she bounced back in a twin set, disc skirt supported with net underskirts, bobby socks and pumps. Then announced she had the pastel green, which we could see, Sara would have the pastel blue, and for added effect there was a nice soft pink for me. I said how lovely, but she was on a mission now to make sure we were ready on time even though we had all afternoon. I knew I could be ready in half an hour, though I dare not say so. Sara and I tried to work, while Jo was asking us to let her brush our hair into bunches or plaits, then try on clothes, or go of hunting for something amongst the wardrobe. By six she had us ready, I had a ready filled bra, and not the ugly sister giants she found first, I tried to appear manly, but was told to be myself and stop mucking about, so I let the clothes influence how I behaved, I had no problem with that. I was feeling so comfortable in the skirt with it’s layered underskirts and satin outer skirt, the bra did not feel right being just foam, but that aside it was nice to be in a dress again. We had an excellent night; we sneaked out of the college, and found ourselves amongst hundreds of other idiots in the theatre. Still on a high we went for a drink, and then had a burger, ending up in Sara’s room and falling asleep on her floor.
I woke up feeling groggy and soon became aware that Sara was watching me, Jo lived around the corner and had slept on her own bed, so it was the two of us and I was being watched. Under the blanket I knew I had female clothes on, and my face had the remains of make up though goodness knows how dreadful it looked. ‘Would you like a coffee?’ she asked, ‘thank you’ I managed. I sat with the blanket pulled up but not sure why, other than it seemed the right thing to do. Sara started reminiscing over the previous night, the show the atmosphere, and eventually the costumes. She matter of fact told me I had no reason to be coy, I looked so feminine she was tempted at one point to shout ‘we’ve got a bloke here’ because nobody was looking at me because I did not look a freak like the other drags. In the end she says she just had to accept I appeared to be a woman, and people were treating me as such so she just went with it. I said thank you for the compliment, but I still feel a little silly because I was dressed in a 50s style outfit which even on a woman in the 90s would look odd in the morning. About this time Jo turned up and we went through the ‘what a good night we had’ again. Then I asked if one of them would go to the workshop and pick up my clothes for me. There was a quick glance at one another and a slight smile, followed by no. ‘we want to see what you look like in normal skirts, and whether you are as good in day light’ ‘please’ I begged ‘I feel rough and just want an easy life’ they offered me an easy life if I agreed, if not unspecified things would make my life uneasy. I tried to look the resigned to it martyr, and asked what had they in mind. Their trousers were too short or tight, so it had to be a dress or skirt that was loose on them, Jo looked through Sara’s clothes, and pulled out a micro skirt, ‘not for daytime please’ they agreed, but the skirt she did hand over was just over the knee and stretchy so it would show every bump, next a knitted top was found and a jacket. ‘Do you want tights?’ and if you wait I think Janice has your size feet’ she returned with sandals, ‘I thought the straps would allow for adjustment, sorry about the heel, now you can find out what us girls put up with’ and smiled. ‘Do you need help with make up?’ I said I had a fair idea but they could offer advice. I asked them to go out while I changed, as I was not sure how they would react to seeing me in knickers. I was soon changed and a with mascara, a little eye liner and lip stick I found by the bed I was ready.
They soon returned, and both said ‘told you so’, when I asked what, they confirmed their thoughts, I was able to pass off being a girl they had thought it for ages and it was nice to see it confirmed. ‘OK so I pass the exam, now what. I would like to get my own clothes’ Jo then pointed out the difficulties, if we went to my room I would surely be spotted in the halls, if we went to the workshop then other classes would be in progress, she was persuading me it was to risky to go anywhere I could get trousers from Rather I spend the day with them. I did ask why they could not go to the workshop, get my clothes, bring them out and let me change in the toilets, to which they refused. I either went on my own or with them. There then followed some odd negotiations, I asked what I got for going along with them, they wanted to know how long I could avoid going out, or being thrown out of Sara’s room. What I wanted to know was how far would they go, and how far would I go. I knew I could easily walk out, but they did not. By the end they had offered to feed me over the weekend, allow me to use their bathroom, (much better than mine), and finish the latest costume. All this to see me walk into town, and return to college later when it was getting empty to retrieve my own clothes. I felt I had a bargain.
The day went smoothly, like riding a bike, I walked easily in the heels, remembered the feminine posture, mannerisms and movements without thinking about them, I even spoke softly when people were around. The experience of being out with a man in drag was obviously exciting for them, and I played along looking in shop windows and asking their opinion on a dress, or seeing a girl and asking if I could look that good. We had got up so late we only had the afternoon to play with before we went to college for my clothes, Jo went in and picked them up, and I reluctantly went to change.
I left the skirt with Sara and asked what time to call for the meal on Saturday, then left for my room to rest my aching legs.
Saturday evening, and I turned up early, Jo was cooking, Sara was still out shopping Jo said. We chatted, Sara returned we chatted and ate and drank. Once relaxed I was quizzed, I was too good, had I done it before? Would I do it again? Did my parents know? Was I gay? Could they set me up to embarrass an odious student who letches at them and thinks himself irresistible? It was obvious they knew I dressed frequently, and that they enjoyed delving into this hidden side of me. I suggested if they had any reason other than embarrassing me I would consider dressing again, which pleased them.
That was October, and early November I went home for an unexpected weekend, the aim being to collect some clothes for wearing at uni. I had worked out where I could change away from the halls, and the fun of walking in on Sara when she was not expecting me in a dress would be worth it.
I felt so at ease now when at home, I felt disappointed to leave, but with a bag of goodies, and wearing female trousers and accessories for the trip back I felt better. I also returned with plenty of undies and nighties for my own comfort.
I restrained myself on the first day waiting till lectures had finished, only using mascara to make up, and wearing a unisex top and trousers. I went and hid to change, and did a fuller job on the face, changed the shoes for heels, brushed out my hair, then painted my nails so they could dry on the way to Sara’s. To say I was elated was understatement; I was showing off and enjoying it. Gently knocking I attracted attention only from her, but when she saw me it was loud ‘look at you comments’. She had noticed me at a lecture, and felt I looked a bit different, but this different, no. She insisted on going out for a drink and calling Jo and Mat (her boyfriend). But no problems, I felt at ease in the role and even Mat soon got used to me.
The next day was more difficult, Mat had told one or two friends, who told others and soon it seemed everybody who knew me or had a vague idea who I was knew about the drink the night before, there were sideways looks, staring, even the occasional comment. There were also one or two signs of support from unexpected people who told me to be myself in a hippy sort of way. Others invited me to a gay club, to which I said I would think about. But having controlled my secret for two and a half years, for it to be out was hard and took some getting used too.
Sara came round for a few nights to encourage me out if she could, but it took best part of a week before I went to anything other than lectures I had to attend. Eventually she suggested we get dressed up and go out, and I felt the effort might cheer me up, and I was right. We decided to get ready at her room, then onto a club. I had a shiny mini and top, with heeled sandals and bold make up soon I was ready. Sara had a new pair of trousers and a crop top, but she had dressed in front of me as if there was not man in the room, and I saw the very sexy underwear she had on, and her good figure, she was very attractive indeed. We had a good night then got a taxi back to my room, I invited her in and she accepted, as everybody seemed to know I wore skirts I saw no need to hide and we walked in bravely, but it was late and no one saw us. We were having some vodka I had left, when she sits very close, asks if I am gay again, I reply that she is very attractive, then she says I am attractive too. In what way I ask, and so she tells me she fancies me, has done for ages, does not really like men, but I was so effeminate, and now I look feminine she certainly did fancy me. I muttered something about being flattered, but was tired and fell asleep soon after. I woke up in the morning as she was leaving for a lecture. I had to clean up and change, arriving late. Jo caught up with me later and gave me a hard time about falling asleep, Sara was trying to be open with me, tell me how she fells and I fell asleep. I was told to find her and grovel. I did and told her I was sorry, which was true, I wished I could have stayed awake; nobody had said they fancied me before (maybe Neil, but you could see his intentions when he said it). The conversation grew easier and turned to the fact I had few truly female outfits, and that on Saturday we should go shopping, it was an idea I liked so agreed.
She turned up wearing denim jeans and jacket, a cap with her hair tucked inside, trainers, check shirt, and when I looked closely there was a bump in the trousers. I was only dressed in my now common androgynous style, to which she commented on how dull I was. If we were going shopping I should at least have tits, then some make up, jewellery, then heels. At last we were ready, I had meant to show her the works in the evening, but I seemed to have to start earlier. Shopping was an experience, did all girls pick up things and loudly ask what their friends thought, or pick something and virtually push you into a cubicle, then insist you come out to show them. Neither Jill nor Mother had been so loud or embarrassing. In the end we bought a sort of his and hers outfit, a silver trouser and vest, with a matching crop top and mini. Then we looked for silver tights, some body glitter, and silver shoes. This took most of the day and exhausted me, what with the lack of practise walking in heels and nervous energy, I needed a rest and fell asleep on her bed. When I woke I found her cuddled up to me that was nice. We then had to get ready, the clothes needed an outing. She just washed and dressed, I had ages to make up dress and generally prepare, you know how it is, and it was well past eight when I was ready. I had done everything, gel in the hair for volume, and make up for definition, clothes and glitter for effect. We had a good night at a club, which was a new one to us. Jo happily bought drinks, eyed up girls, and watched men eyeing me up, always nudging when one made it obvious. We danced, drank, cuddled and then got a taxi back to her room. She then got very intimate in the crotch area, asked how much I fancied her, I kissed a response then asked her the same, her reply was to ask if I had a working dildo, I was puzzled, of course not in these clothes. Her hand slowly slips inside my knickers to find a restrained stiffness, you have down here she announces and undresses me to the knickers and bra. I then watch as she undresses and climbs on me, the rest you can imagine.
The fun continued, we became a fixed couple and spent most time together. She wanted me to wear skirts and express my feminine side more openly, but I was more cautious wanting to offend no one, and not be embarrassed. So I would get dressed up if we were going out special, but for study time it was trousers, although I did use mascara more frequently and wore only female clothes. I had a lovely time when we decided to go to the Xmas dance, Sara and Jo wanted to go in fancy dress as that was advertised. Jo and her boyfriend found some mime artist costumes, and reckoned they would be fun. Sara wanted to be lavish and suggested Fred and Ginger, guess who would be wearing the top hat and tails. We borrowed from the drama wardrobe and I had a wonderful time going along the rails, Jo had to alter her trousers but found a jacket that fitted well, the hat sat smartly on her head. I came out with a powder pink gown, the body was tight fitting, but the skirt and sleeves were made to fill out and float, and with the copious material it flowed with grace. There were some draw backs, my waist was a little to big and I thought we could let it out to my size, but there was no material spare, the alternative, a corset to reduce the inches, Jo seemed surprisingly enthusiastic for me to wear one, we managed to find a pair of pink 4” stilettos, these felt like stilts after my usual high heels. Last of the difficulties was the hair, looking at period photos, I should go for bleach blonde or ginger, my hair was lighter but peroxide? It would also need to be set and lacquered with a big fringe and bobbed neck. Sara meantime had found a cane and some neat brogues. I pointed out how easy it was for her to change, but I had to get used to the corset and heels, not to mention getting used to the hair, blonde we thought would go better with the pink. So on the Thursday I bought a bleaching kit and hid in the bathroom and let it work. I left it for a little extra and the result was startling when I rinsed it, I was a beacon blonde, no one would have natural hair this colour. Then on the Friday I had booked at a salon Jo recommended, I dressed in a skirt and tights so as to blend in, but Jackie asked if I was Sara’s friend and told me how much nerve I must have, then set about the hair. I was curled, and put under the drier, then brushed out and set in place, the fringe was big and would not move, the neck was a little softer, but it was the look I was after and I certainly had it. Sara meet me and I was grateful as I could feel people looking at the outlandish hairstyle I was sporting. Once at her digs I started to make up and dress. Sara had bought a set of white satin undies and white stockings for me. She seemed to enjoy pulling the laces on the corset tight, but it was worth it to see the gown fit so well. Sara then appeared in the top hat, tails, cummerbund, cane, shirt and bow tie, but the shock was the thin moustache, and short hair. She pinned a carnation to her lapel, and fixed the lilies to my hair as Jackie had advised, I pulled a stole over my shoulders and wafted out to meet Sara. She made all the right comments to us, then we made our way to the dance.
There were many good outfits, and some rubbish, it was also easy to spot the drama students, they were the best. I drank babycham, and enjoyed the gown floating around me as Sara lead me around the dances that were suitable for a Fred and Ginger routine. Sara was genuinely shocked at how many people did not recognise us, and got our genders mixed up, not helped by me calling Sara, Sam. And Sara calling me Lauren. We had a smashing night, walking back in the early morning, Sara swinging the cane, me trying to keep the hem off the pavement. It was some time about then that she invited me to visit her in the holidays; at her parent’s house but only if I came as Lauren and left every piece of male clothing and mannerism behind. I expect it was offered in the excitement of the night, and I must have accepted in the same way, because when I thought about it next day I had never gone for prolonged deceit, people either knew, or it did not matter if they did or they did not, only on the weekend with Neil had I done anything like this. But when Sara called in the afternoon because we had to return the costumes, she asked if I would come before or after Christmas, oh what suits you I said without thinking, straight from here then, leave your stuff here till next term and come and meet my folks, I’ve agreed it already. Then she told me how straight they were, and how I would have to live as a girl totally.
Well the last week of term was odd to say the least, I was thinking of reasons why I should not go with her, but then she would turn up and I knew I wanted to spend time with her. Finally our last day came and I packed my bags, dressed sensibly for a rail journey, and waited for her. She arrived as butch as she could, then offered to carry my bag, which was nice. I made some comment about me having to be all girlie and she dresses like a bloke, tomboy she corrected. I let her do all the work, she seemed to enjoy being in charge of ticket buying and train platform selecting, I just followed on like a helpless the female she wanted me to be.
Her parents seemed very nice; I had the spare room, her mum made sure I was comfortable. It was clear I was just a friend, not a partner, but I still had plenty of time private time with Sara. Her parents critised her for liking of trousers, I felt it sounded like my house at times some years ago. The days passed pleasantly, until Sara asked if I had any tampon, of course not, well she pointed out all girls do, so she gave me some to leave out for her mother to see, then suggested I try one, or leave the wrapping in the toilet to be convincing. I can only say it was like a little dildo and got me in the mood for the evening.
We were left alone and got up to intimate things, but when Sara’s hand strayed up my skirt she found my tackle though excited, taped up as it had been for the duration. So then she disappears and returns with a real dildo, and asks if I know what it’s for, next thing she finds the string hanging from the tampon, and tells me she is going to only think of me as a girl from now, I thought it a little hard myself, I had stick on boobs, a taped back willy, and only an arse, but was ready to go along with the idea. She made me open my legs so she could work the dildo, and to my surprise I climaxed, this really pleased her and set a fresh level in the relationship, she had reversed the roles in her mind. This became evident when she asked if she could visit my home as Sam the partner, I was unsure as she looked like a butch girl, but a girl all the same. She could come as Sam a friend and see how my parents took her, which she accepted.
The main impact of staying with Sara was that I felt totally at ease in my skirts, and no one saw through the disguise which surprised me at first, but I grew not to even look as the days passed. I had to be careful not to be seen undressed as her parents would go berserk she said, but I kept everything taped or glued in place and thought nothing of it. I felt liberated.
I arrived home in a skirt, which always pleased father, but the freedom of nobody knowing my past evaporated, I was unsure about going out too much, just in case somebody recognised me and caused a fuss. I wanted to be with Sara, for her confidence, affection and I suspect bossiness. But we spent Christmas apart; she arrived on the 27 Dec, and left a good impression on my parents. For the student fancy dress she had cut her hair, since last seeing her it had been cut by a barber, into a very male cut, neat parting, fringe and square neck, she looked like a 5’6” bloke in jacket, trousers, shirt and tie. She introduced herself as Sam, and mother asked if it was short for Samuel, to which she asked to be called Sam, as Samuel sounded so old. I helped her unpack and she made it clear that if I could spend time at hers as Lauren then she would be Sam, even down to the boxers.
We could use a car, and went out quite a bit. One afternoon we visited Jill, who by now treated me like a sister, and would chat about make up, clothes practically anything but men were avoided, when she met Sara, she said nothing at first was just polite, then quietly pointed out it was ironic I should find a partner the same as me, just reversed. I was shocked and told her it was not my idea for her to be so masculine, but I was told to calm down, I was doing the same just the other way round. Then when Sara came back, Jill asked if we fancied going to a New Year dance, I knew how dressed up these were, and told them we had not got smart enough outfits, Jill winked and said she had the green dress, that I could borrow and the extras if needed, and Sara could go and hire something formal. To which she asked for a yellow pages and started ringing round, and as I regained my senses asked Jill why she had to encourage her. She then virtually told me off, she called me she, and never referred to me any other way, and I had had to be persuaded at first, but now I expect to be seen as a female, Sara wants to do what you do, don’t look down on him. More was said but the centre was, think of Sara as a male.
On New Years Eve we had a busy day, Sam had to collect his dress suit, and I had to get my hair done, I had tried to soften the effect of the blonde, but the roots and general colour was poor. So I allowed Claire to sort me out. Coloured to a light brown, and then styled with sponge padding, to give a swirling spiky effect. Mother treated me to a manicure; needless to say I came out feeling great. I was the last booking so I went straight home to get ready, mother was keen to help and laced the corset for me, bringing me in tight enough for the dress to zip up, which was surprisingly firm, she left me to fix the stockings, but wanted to help with the make up, she assured me she had been reading the magazines and had been trying out current colours, I expected to need to check, and change things after, but it was fine. Then she lent me her emerald jewellery, it looked and felt gorgeous on, pendant earrings, a pendant necklace and a ring. Then she was of to see if Sam was ready, obviously checked him out, then gave me the car keys and told us to have a good time, and commented on what a lovely couple we made.
Sam had the works, smart suit, wing shirt, bow tie, cuff links, that father had lent him, and patent shoes. We complimented each other, then agreed we would hate to be wearing the others clothes, which was lucky as I did not want to give up such a special dress, for such a drab outfit. Jill and Bruce took a lift of us and we had a great time dancing, eating and talking. Sam was able to dance the male part with ease, and I did not know if Bruce had been told about Sam, but he said nothing and treated him like a bloke, which I know thrilled Sara. About 2 PM the party started to unwind, Jill had not drunk much so we agreed she drove, but this meant not getting home. No problem, we could use the spare room, fine we accepted.
Once back Bruce made a coffee, and Jill said she was going to clear a space in the spare room. Once alone we found the spare bed to be a double, and hidden under the covers was a satin nightie and vibrator. ‘Bruce tells me you will need help undressing’ Sam said, so I explained the New Year a couple of years ago, and as I slid the dress off there was a sigh, ‘lovely’ I then undressed Sam who was in boxers of course, and we used Jill’s gift to effect. I was very securely taped so I used it on Sara first, but then it was cleaned and lubricated and the attention centred on me, and no I did not lie back and think of England.
In the morning, Jill asked if we had slept much, then Bruce laughed, and commented on the noise the bed was making. ‘Don’t know how you do it but it sure sounds like you enjoy it’ he said. I just blushed.
Sara spent something over a week with me, and father was making comments about what I would do when I finished the course. Only the doctor wanted to know how I was getting on, and was asking about the future plans. I talked about how I had felt when I stopped at Sam’s, and the feeling of ease I felt when dressed. He would smile, and nod. Then one day he asked Sam how serious we were, and how I was. Followed by a question about whether Sam thought I would consider surgery.
Sara and I discussed this, and the friendship moved onto a more serious level, I fancied the idea of implants, and Sara suggested we look for work together, maybe set up home together. This was getting all very definite, and mother asked a few subtle questions, the answers that she relayed back to father. Who then took it as firm that come the summer we were going to live together, and I was going to have implants. Mother then let slip that father was really pleased I wanted surgery, I almost freaked, she had always ignored my male body, now she acknowledged it, followed by ‘your father is really pleased you want to be a real daughter’. It sank in that father had been a prime mover in the daughter creation, I felt deceived by him. But Sam got me to be practical, what did I want, and if father would pay then make the most of it. It still left a bad taste, that if I had been left alone how would I have turned out. Sara’s response was ‘I love you as you are, lets go shopping and buy you a complete new outfit, get your hair done, go out tonight somewhere smart. If he wants a daughter he has to realise they are expensive to keep’
Spring term to finals
Soon we were back at our final studies, but we had become a definite couple now, and at college dressed interchangeably, at evenings we became more obvious in our preferences. Our main pastime, especially when Jo was not around, was to go hunting in the costumes and come out with a couple of period outfits, and dress complimenting each other. Over the term we must have covered every century back to the middle ages. I liked the stiff and formal Edwardian styles, Sara went for anything like a uniform, even armour.
Just before Easter two related events happened to catch me unawares, first I got an appointment with a surgeon who performed implant surgery, with a possible date for the operation, and my tutor asked me in for a private word, because the dean had had a request for my degree to be made in a woman’s name. He would have been blind not to see that I was dressing feminine even to college, and he was realising the request did have substance, but he wanted to be sure, and I would have to actually see the Dean for such an unorthodox request. What connected the two was my father, he was setting things up, the doctor, the Dean, and I did wonder what next.
I went to see the Dean, in a skirt (Sara’s idea) and he gave me a hard questioning about if it was correct, but he had to accept my life would be easier if I were to live as a woman if my qualification had an appropriate name. The doctor was more matter of fact, he was asked to do a job, various people had supported the operation, he said he would do it after I finished the finals, so I would have breasts for the graduation. Now there was a thought, graduation in a dress, my parents would be proud.
I called Sara and asked her to call round with a hard job. I was going to go through all my clothes and dispose of anything remotely male. Sam could do all the carrying; a girl should not if someone else will. During the clear out Sam suggested all the trousers should go, but girls do wear trousers so why couldn’t I, was my argument. She accepted but insisted I wear a skirt to college for the rest of the week, reinforce the decision she said, more like please her. But I obliged with suitable skirts for her.
Then it was down to the final study, get the assignments finished, and revise for final exams. This meant little time together for fun, just work. But it had to be done. Eventually the last exam was sat, and all the course work handed in. We were free, along with loads of other students and with them we got embarrassingly drunk. We found ourselves the next morning in our underwear sharing a bed with Mat and Sara. What had we done, fortunately nobody knew for certain, but we were all cuddled up, Sara, Jo, Matt, and me across the bed, with sticky fluids still evident. I had a vague recollection that Jo had said the best person to have sex with is someone of your own sex, because they know best where the G spots are. Which meant Matt and me had done it with Sara watching? Jo later confirmed it had always been a fantasy to get us all in bed and swap partners. It seemed her dream had happened.
Pretty soon after our last night all together, we split up going home mostly, promising to keep in touch, Sara wanted to know if I would like to keep in touch with Matt, when I said that would be nice, she asked if she should be jealous, then smiled and slide a finger up the inside of my thigh, ‘jealous, never, we are the couple, you are mine, and I am yours, unless there is fun involved’ then she winked and touched my dick. She was right; I would do anything for her/him.
Father had all my life planned from the time I got home, I had papers to sign about change of name and status, and a day to pack before going into hospital. Sara had been insistent on bust size, she wanted a D cup after I refused to have F cups, she wanted to emphasize my femininity, I wanted some comfort, and so D was a compromise Jo would not go below. She stayed at my house and visited at every opportunity, along with the rest of my family. And once I was home wanted to nurse me, but there was competition with my mother for that job.
We also had to find work, Sara had not changed her name or status like me, so had to go for interviews as a woman, which made her a bit prickly and possibly did not help her chances. For me I was coping with a sore chest when reading the newspaper, I saw a business for sale. I showed it her who thought it could be good. So I thought the time was right to do some manipulating of my own, my parents had got me to be the daughter they wanted. I used this and a daughter’s charm on them to agree to look into this business.
To cut a boring story shorter, the books were good, the position great, and potential excellent. So that September we took the keys to a fancy dress and costume shop, best of all it had a flat, and father had covered all the costs, we were to pay him back out of profits.
Now we could do what we enjoyed, and be the people we want to be. As well as having a shop full of clothes to muck about with doing role-play when we closed the shop up for the night.
Paradise.
I was staring at my friend Andy, no Amy, no Andy, no Amy. She, no he, was standing in front of me in a set of grey satin underwear, which included a suspender belt that was holding up some glossy stockings. The hair was perfect, the make up ideal for the situation. The voice neither falsetto nor too deep, just sexy, no wonder I was confused.
'Oh fuck me' I exclaimed.
'No darling, that is what you are going to do to me later.'
I was staring at my friend Andy, no Amy, no Andy, no Amy. She, no he, was standing in front of me in a set of grey satin underwear, which included a suspender belt that was holding up some glossy stockings. The hair was perfect, the make up ideal for the situation. The voice neither falsetto nor too deep, just sexy, no wonder I was confused. I knew this was Andy, my friend, but tonight had he had been set up so that he was my 'girlfriend', and Amy was perfect, even if somewhere in a cupboard marked 'Do not open', was the truth that my 'girlfriend' was a lie.
It had all started a few weeks ago as I was coming to the end of A level exams, with summer holidays ahead, school behind us and university to come. What could go wrong? Andy, that's what. He had been up to something and once more he asked me to cover for him by saying he was with me. I have no idea if it was girls, drink, weed or other lads, he did not want his parents to find out about, but every now and then I got a call for a favour. I should have known better. He should have known better, our mothers knew each other and would talk. I was 18, about to leave home, where was the harm? Even if he was rumbled, I was ok.
That is not quite how it worked out. The Tuesday after the weekend of covering the lie, Andy and his mum are in our house. Andy is looking cocky, his mother flushed with fury.
'So Mark, Andy was with you?'
I was set up. Mum was there, she knew I was home early that evening.
'Yeah, we were together'
'Till when?' His mum was being unusually frightening, I always had her for a soft touch. I tried to side step her questions until I had squirmed enough, then she just came out with the obvious. Our mum's had been talking. Andy's reason for being out late was a lie, and I had lied to cover for him. I thought that was it for me, I had let a mate down, but it was his lie and he was found out. Now he had to face the music, not me.
They left, with Andy being bullish, saying more or less 'So what'. My own mother gave me a hard time about the lie, and how she was dissappointed in me and the shameful situation she had been in when her friend had accused me of not being honest. I made the right noises and apologised, but I did sense that it was not going to be dropped that easily. Sure enough, I half overheard a conversation that our mothers were having on the phone, Andy's mum clearly still livid. I still had no idea what he had done, other than string her along for years with his lies. I knew it was not over. Without introduction, mum walked in front of the TV and announced 'Tomorrow, 7pm at Mary's, do not be late.'
Of course I had a text conversation with Andy. He was having a rough time with his mum. She had gone ballistic. This last lie had been the straw that broke her back and there was much shouting and tears, plenty of laying the law down. He was indignant that she was treating him like a child. He kept on saying he was old enough to leave home, all the usual stuff I had thought of saying to my parents, but never actually had the guts to say, just in case they called my bluff and said, 'Ok there's the door, let us know when you find a place.' The texts went on right up until I arrived at Andy's and was ushered into the living room. Andy was there looking worried, his parents looking determined, my mum looking nervous but serious. All this just made me feel very uneasy about what might happen in the next few minutes.
I was right to be worried. Andy's mum started by explaining to us all, how Andy had been pushing the boundaries for far too long. She knew he was lying when he was out late. She was sure he was up to something and until last weekend, had just let it go rather than challenge his behaviour. Well, that all changed when someone said something and that person really rattled her cage, and this time it was not being forgotten. This time she was going to make up for all those times she should have pulled Andy up and had not. Why was I there, was all I could think of. Andy was in deep, but why me? Then it came. I knew there would be a punishment of some sort and it was very inventive. She was in control, which was unsettling me, as she explained that seeing as how we had lied, she was going to make us lie in a big way. Now I was confused as well as worried. Andy, she said, was going to a wedding party with me. I knew the one. In August, some cousin we never saw who lives miles away. I was going with mum and dad, so what? Well, the lie we would have to pull off would be that Andy was going to go as my girlfriend! I am not sure how Andy reacted, though it did involve some swearing. I just asked why me? What did I do? My mum simply pointed out that I had helped him with the last lie, so I could help him with this one, as I quite probably knew what Andy was up to when I covered for him. I was floored. This could be so embarrassing. What if and it would be a very easy if, someone spots that my 'girlfriend' is a lad. Her answer, best make sure no one does, or else I shall look a fool, because they will have all sorts of lies to tell about me. 'In front of family, you will make me take Andy dressed as a girl to this wedding, and if he looks like I suspect he might, you will just disown me and say it is the way we are? Have I got that about right?' Her short answer was yes. I tried a few attempts that I did not know what he was up to, that this is unfair, this is out of proportion, this could backfire on you. All had no effect.
Andy was having a similiar time it appeared, when we later compared notes as it were. He could not believe his mum would make him do this either, but he had to accept the final crushing reply. 'My house. My rules.' He could leave. No he could not, not without living rough. He was broke, having spent all his money and some more on his nights out. I still did not know what he was doing and did not really want to know now. Andy tried to make me feel better by pointing out that at least I was not going to dress as a girl. True, but I was going to be humiliated in front of family. We spent the rest of the evening commiserating with each other and planning how to aviod this disater.
I got a text next day, telling me to get round quickly. Andy sounded desperate so I went over. His eyes were bloodshot. Clearly he had been crying, but that was not the first thing about him that struck me. He was in his room, wearing black leggings, a short denim skirt, a red girls tee and a defeated expression. Not only had his mum made him wear these clothes, she had removed all his regular 'Andy' stuff. Andy wanted to know if he could borrow some of my stuff, but I did point out that I was much bigger than him. He was possibly 60kg tops, and maybe 5'6". I am 6' easy and over 80kg. There was the problem of getting my stuff to him or him to my stuff. Even if it did fit, his mum was bound to find out. I left, promising to be back later with some of my smaller clothes.
This was not a good plan, as I am sure we were overheard, because when I tried to leave with a bag full of stuff, mum intercepted me and asked what I was doing, there being an emphasis on not lying when I answered. I told the truth and returned the clothes to my room, and let Andy know we had been found out. He replied he already knew, and his mum had put an end to his ever showing his face outside again. I asked how? He told me she had given him breasts. Not understanding, I went round as quickly as I could. He had worn a bra the day before, which had made him look quite feminine. What was different now was that with the use of threats and force, his mum had glued on him some fake tits, like the ones women with breast cancer use, and if anything they looked bigger, more rounded, actually quite real. No way could he go out and hide something as obvious as that pair. I nearly said 'nice pair' but held it back, he was suffering enough. I left him to try and reason with his mother, but instead of the nice woman I had known for years, I got a stern response. You supported him in his lies, now you support him in this. Make him live this lie or you both will be humiliated if anyone works out that 'Amy' is really Andy. I nearly asked 'who is Amy?' but the penny dropped quickly enough. Seems I might not have to dress as a girl, but I was most certainly far too closely linked with this to walk away. I had to go back and try to calm my friend down and make some plans for our next few weeks.
His mum came up with a few things that helped. She had told people who rang that Andy had got a job working away. Her niece was staying the summer, which would explain why any possible similarity to Andy, Amy's cousin. We had £500 to spend on clothes, make up and anything Amy might need while she was staying. His phone had mysteriously vanished so he would not be contacting mates without going out. And a final threat that my mum was fully behind her, so I had better do my best or share in Amy's failure.
We spent the rest of the day in Andy's, no Amy's room now, drinking coffee and trying to find a solution. In the end, we both were beaten into the realisation that the only solution was to accept the fact that Amy was going to be about. This I knew was tougher for Andy to accept than me, but I also realised that I was going to have to be the main support for my new 'girlfriend'. I did tell him about the helpful things his mum had done, though I do not think he took them as positives, more like nails in a coffin. But when you are dressed in a skirt, it is hard to find the silver lining to your particular cloud when you think you would be more comfortable in loose jeans.
I did all I could to help lift his dispondent mood, but after a couple of days of trying, I was getting worried that it was not going be a good outcome if Andy did not stop sulking, and at least start trying to be Amy. Then I called round, and he was his more normal bubbly self. Don't ask what happened, I have no idea, maybe he just saw that what I had been trying to say was right. 'The best and easist solution is to just get on with this bizarre punishment and get it over with, who knows it might even be fun.' He was overacting quite a bit, playing with his skirt, flicking his hair off his face, that sort of thing, but the biggest change was how he looked. His hair had always been long and straggly, but now was washed and brushed out. When I mentioned it, he said 'us girls have to look our best for our boys' and fluttered his eyelashes at me. At least he was not sulking. I got him to sit down and we discussed how he should play his role. We decided on a regular girl, no over the top dizzy girl like some we knew, nor an earth warrior type, just a girl next door look. His mum had some magazines we looked at, but they seemed too old for what we wanted, so it fell to me as the only one decent to go out to visit the news agent and buy some magazines, cosmo and the like. That had me blushing as I put them on the counter and paid for them. I know men buy them all the time, but this was my first and it was awkward. We had an interesting time reading, looking at pictures and discussing what was there, but we felt that the clothes his mum had given him, short skirts, leggings, tees were about right for now.
For the first time in years he was home on the weekend, but seeing as it had fallen to me to make sure this punishment had little impact on either of us, I set about planning what should be happenning before our big day. I even had a chat with my mum, who had clearly had a chat with Andy's mum, who wanted to see him getting out and living like a real girl might. Shopping, going out with lads, dressing up, preening, all things he was currently not doing. But I could see that if he got used to being out as a girl, come the party he would be more confident and carry off the lie much better.
Sunday we asked his mum to show him the basics of make up. I was amazed at how much this changed his face. I could tell from his expression when he looked in mirror that he was surprised too. She brushed his hair about a bit too, and lent him two hoops to replace his boy ear studs, and we just had to call him Amy. I spent the day helping him learn to behave like a girl. We picked Vanja from his tutor group, as a model to copy, and having donr drama as one of his subjects he picked it up quite well. After another day at home, and he was getting better. No lad in a skirt or hamming it up, he was coming across as a girl more and more.
Things seemed to be going fine. I suggested that I could borrow a car on Wednesday and we go out, maybe see how he felt in the big wide world. It went not too bad, he was terrified to leave the front door at first, thinking every neighbour would be watching, but then he sat really low in the car. He need not have worried, his mum had done his face and hair and he looked great. We drove out to a park on the edge of the city. I went and bought two ice creams which we ate in the car, then the big moment. I persauded Amy to go for a walk along the river, not a great scenic idyll, more a track by a quiet stream, but we did it, Amy had stepped outside.
By the weekend we had been out a couple more times in the evening, and on Saturday Amy was persauded to go to the Trafford Centre (a large shopping mall) and just blend in with the masses. This was a big step, and stressful for both of us. Amy might not be recognised, but I could be, and Amy would be rumbled on close inspection, but the mall was a good way from home and we would just run if we saw anyone we knew. That was the plan and it worked, as we saw no one we knew. Eventually we relaxed and bought a coke in the eating area and watched the throng of people milling about us. I started to comment on particular looks of girls , Amy even picking out the odd style she might try. Now we were getting somewhere. I suggested we spend some of the money, and after a few false starts, as we only got just inside the shop door, we finally made it to looking at the racks of clothes hung up. We were looking for a batwing top. After a couple more shops we found a cream one. No way was she trying it on, so I just paid for it and we left. Exhausted from the nervous energy used doing this, we retreated to the car and home. His mum was very impressed with the purchase and wanted to see it on her. We chatted a bit and told her how uncomfortable the experience had been, she just pointed out that lying should be uncomfortable.
This I reckoned would need to be the first of many such adventures, as we got Amy used to being outside and seen. Amy wanted to make herself look as different as possible, hoping to hide any feature that might hint at the true Andy. We decided that Amy should have a new hair colour, made into a proper girl's style, and maybe a fake tan. I ran these past my mum who seemed to approve. Unfortunately by the time I meet with Amy the next day, something had happened and the sulking was back. All that feminine poise was gone, a slouching teenager had returned. The reason for the regressive Amy was that her mum had made an appiontment at Kut Hair, a salon not far away, and one she would be recognised at, as that was where our mother's went. I managed to get the booking cancelled, but on the condition that by the evening, Amy had blonde hair, a tan and long nails, which was not on the original plan. I rang round distant salons and found one that would handle the tan and nails, and another which would do the hair later on.
Amy was not happy, but unable to really complian or fight, accepted what I had arranged with a resigned attitude. Like a lamb to the slaughter I thought, as I dropped her at the first shop. I waited, not knowing how long it would take, and was relieved that I did, as a distressed Amy came out only minutes after going into the back. They needed her to strip off, which we both knew would mean revealing her true gender. I came up with some quick lies about how Amy was doing it as part of a bet with a girl who had challenged him to have salon treatments done. On hearing this, they giggled and were apparently taken in, suggesting that to impress the girl, they could wax Amy as well. I only asked how much, not will it hurt, and because of the tan and nails, they did it cheap. I suspected later that it was to see Amy's reaction when the strips were pulled off.
The treatments were successful. Amy was now hairless, including most of her eyebrow hairs, with a very unnatural coloured skin, which we were told would fade with a shower later, and some extended shiny pink nails that seriously impeded her dexterity. As for looking like Andy, well with skin that colour, it was anybodies guess who it was. One last little treat the girls did for Amy was to suggest a shop across town that catered for men who like to be girls, and get something to hide the obvious male feature. Two days later, we called after phoning and bought a sheath that glued to the penis and secured it between the legs, creating a flat front and making Amy unable to pee standing up. Anyway after the tanning session, we went to the hair salon to get her hair done. No drama here, they accepted Amy as a girl, commented on the tan and gave advice on how to handle it while putting liquids and gels on her hair that not so long ago had been a pony tail. By the time we got home, Amy looked very much a girl. The mixed blonde hair with just a little wave and a long fringe clipped to the side made my 'girlfriend' look nothing like my mate. I felt Amy was not quite as pleased as her mother, who had a rather satisfied smile when she got a good look at her part time daughter. Not that she knew about the willy sheath thing, but I am sure she would have approved if she knew. I did though, and thought it might be interesting to see how Amy looked in a tight fitting skirt.
That weekend we went into the shops and shopped with more success. Amy bought a nice, cool looking summer dress. I choose a leopard print, stretchy skirt and another first, we bought some shoes, low heeled espardrills to go with the sundress. Another first happened that day was that Amy found the experience quite a buzz and was clearly on edge at times, but also showed times of enjoying the novelty of being someone very different to who she normally appeared as. This was a watershed in some ways. Amy realised that with care, this new look could open up a whole new range of oppurtunites, and the bubbly character she had had as a lad more or less returned. There were complaints about how long it took to do makeup and hair, the awkwardness of the nails and the thinness of the clothes when the wind blew, but overall there was a big change in her, which would make the lie easier to carry off.
His mum though was still wanting to push the situations we should be getting into, and encouraged us to go out in the evening. This could be difficult. I was 18 but even if Amy had been 18, then how could we show an identity card with Andy's face on it, without admitting the lie. Amy became a teatotaler that first night we went out. I was in my usual tee and jeans, but Amy made a effort and wore black tights under denim shorts, and a rather tight vest top which showed off her bra straps. I told her she looked good when I picked her up. She rebuked me with 'only good!' I took the point and remembered to be more flattering in the future. As we sat with our fruit juice and beer in an unfamiliar pub, hoping not to see anyone we knew, the topic of Amy being my girlfriend for the wedding party came up and different ways in which we might behave. We were still mates and hardly ever touched each other, well lads don't, do they, unless they are gay. We needed to work on a believable relationship and wondered just what this might entail. We could hold hands to start with, maybe cuddle if sitting close. Kissing Amy I was not too sure of. I could see this was challenging her personal gender view, but from my position, I was looking at a good looking girl who was my girlfriend. Why would I not kiss her, it would be unnatural not to. We tried holding hands on the way home. It was a little strange to start with, but once we had got comfortable, the warmth of another's touch was rather nice. When I dropped her off, I suggested a cuddle next time, she said wait and see, one thing at a time.
For the first time in a couple of weeks, I felt that I would not be needed to keep Amy on track, that at last she could be left to develop her feminine personality without me. She would probably practice the walking and posture, do some vioce training with a recorder, have a go with the makeup and see where her artistic tendencies took her. With my day alone, I considered what might happen if we were seen, would anyone recognise Amy, would the lie that Amy is Andy's cousin work, does holding hands with a mate make me gay, does holding hands with a pretty girl make me straight? Will I be laughed at come the wedding? I knew better than air my concerns with any family member, who would just give the standard response 'well you should not have lied.'
The next day, I texted Amy 'what are you doing today?'
'Shopping'
'Oh'
'Will you come?'
I was round like a shot. Her mum had told her in no uncertain terms that Amy was going to be dressed up for the wedding, and in her opinion, that meant heels, so she had to get some heels and get used to walking in them before the big day, or else her feet would kill and any feminine poise would be lost as she staggered about trying to stay balanced. We bought some black ankle boots with a 2" narrow heel. She said they were fine in the shop but later, after she had walked about in them for a few hours, did admit her mum was right. 'Heels need practice'. I asked what sort of a heel was she expecting her to wear for the wedding. Amy looked dismayed as she told me her mum wore 3" heels as routine, her dressy ones were 4". I could only make sympathetic gestures, while inwardly thinking how hot a girl in high heels looks, and I saw no reason why Amy should not look just as good. I suggested we go and look for something higher that afternoon, but she declined, saying it would be an excuse to go shopping another day. I accused her of getting too much into character if she wanted to go shopping. She went to slap me, but I caught her hand, then as we stood there, her wrist in my hand, I looked into her mascara-ed eyes and saw a playful glint. She was getting into this so well now that I could easily believe Amy liked being Amy. We made our way home holding hands, and on the train sat deliberately close, so our arms entwined.
'You're being very friendly' I observed.
'You are as well' I blushed at that one. 'Just getting into the role, don't flatter yourself into thinking I fancy you.'
I denied I was thinking anything of the sort, and if we had not been squashed in the seat, I might have tried to wriggle myself free. As it was, I had to remain while she told me I had nice soft hands. I did feel that she was playing with me, so later as we stood at the door waiting for the train to stop, I put my hand on her shoulder and pulled her close to me. She stiffened a little, as she felt the pressure of my squeeze, but in my mind I was the boss, her mentor. As we walked home, I took her hand to make sure she knew what I wanted her to be seen as, and then it happened. Joey, a friend from school saw us.
'Hi Mark, how's it going, good to be finished at school, waiting for results is a pain! What do you reckon, got my aunt stopping by, and her horrid babies, best out of the house' he went on like this for ages it seemed, all the time I am thinking he is going to take a longer look, or at least a more critical eye than the checking out he had given Amy so far. I was not listening when he said 'so this is Andy's cousin, that did not take you long' he nodded at our hands.
'Just showing her round, being a friend you know.'
'Oh yeah, right well, best be off, got to see Steve about going to a gig tonight.'
And he was off. I am not sure if either of us had taken a breath the whole time he had twittered on, but the release of tension was audible as he moved away.
'We did it, or more like you did it, Amy, that was brilliant!'
'I was sure he was going to to say hi Andy or something'
'But wow, how did I stay composed, I expected my voice to crack when I spoke.'
'So now that the town gossip has seen Mark out with a girl, what do we do now?'
'Nothing, that is what your mum wanted us to do. She wants us to pretend to be a couple, lie, as she puts it.'
'I know, but now we are a real public couple. Where do we go from here?'
I thought quickly. 'Well in that case, I think my girlfriend should have a' I turned, faced her and kissed her lips.
'Mark!'
'what?'
'I was thinking more along the lines of where should we go as a couple in a geographical sense, not a spiritual or intimate sense.'
'Well anywhere we fancy really, I suppose, but this boyfriend is going to do his role right and get a proper kiss out of his girl some day soon I hope.'
'Come on you randy thing.' And she walked off, ending the conversation there.
Her mother seemed pleased to see the heels, and commented how they affected Amy's walk, hinting that higher ones would look even better. We arranged to go to the shops in two days time, as I had promised my father to do some jobs for him the day after. So I left Amy unsupervised by me for 48 hours, and wondered what she might get up to now that she was growing in confidence.
Nothing it seemed. She took a day off and just did some housework for her mum it turned out. I decided we would get her some of the highest heels we could find and some underwear. My logic being that all lads like their girls in sexy underwear, so why not me? An uneventful train journey, a few resistant noises to my choice of shoes, but eventually she choose a pair of black courts with a thin platform sole, but refused to wear them home like she had with the previous pair of heels. Next, the underwear and this was more fun in a way, I had never looked at so much female underwear and could have bought her everything. I was not sure if she was thinking like a man or a woman, because this was clearly something new to her as well. The lad thinking like me 'this would look great on a girl' yet I could also see the other side saying 'what, me in that, soo tacky'. In the end, we had a red and a white set of satin underwear, plus a few different styles to try out. Thongs, french cut knickers, underwired, and half cup bras, hoping the size was right. No way was Amy going to try on anything for fit, and she did not seem to mind the prospect of returning items that did not fit.
Back at her house, I asked if I could see the purchases on her and she went all coy on me, and pushed me out of the room, not liking the idea of me seeing her naked. She was changing for sure, because it was only a few months ago we had both been in the same changing rooms after a PE class and her naked body had been seen by many. Most fitted, I was told, but a few would need returning, which she pointedly informed me she would do alone on the weekend. I was amazed and a little hurt that she did not want me to go with her. I could see that it would help if she had confidence to be out on her own. I still felt a little redundant.
That evening our mother's decided to have a bottle of wine together, to keep each other up to date with our progress I assumed. Amy came with her mum and after a polite glass of wine with them, we took our glasses into another room. Amy looked great, hair had been curled specially, make up more obvious, her longer looser cream top, black leggings and the new black stilettos, with a new accesory of a scarf, which was purely for decoration. The revelation that evening was to come as we sat and sipped our alcohol.
'I am wearing the thong' she casually commented.
'Oh' I stammered 'and is it nice?'
'Don't get a panty line showing through my leggings.'
'And that is important?'
'Of course it is silly, no girl wants everyone to know what knickers she has on.'
'Oh right, and do they feel nice to wear?'
'Odd having the bit between my arse cheeks, but yes they are nice.'
'Oh good.' I was feeling unsure of myself about this. Then she continued
'You should try them sometime, these female clothes are so nice.'
'Oh err' I was stammering again.
'The satin in the bra is so soft, those french knickers, they are silk and soo nice. And tights, they feel great on my legs.'
'I will take your word for it.'
'Here, feel this.' She held out the hem of her top for me to feel 'really nice soft cotton, Andy never wore anything this nice.'
I felt the cotton between my fingers and had to agree. All my cotton was stiff and thick textured. Then in a moment of pure lecherous thought 'So do I get to feel what a satin bra is like?'
'Mark!'
'I only asked, to see if I agree with you.'
I think the wine had got to us both, me for asking and now for Amy's response. She took my hand and slid it up inside her top until I had a breast cupped in my hand. I had to agree the satin bra did feel very nice. It was also the first breast I had felt,, and was getting a bit excited with the whole situation. While still feeling the cup, I leaned forward and kissed her.
'Oh Mark, I do believe you like me.'
I pulled away 'well you do look great, and we are supposed to be a couple, so maybe we need to practice the more intimate parts of being a couple.'
To my surprise, she answered 'suppose you are right, couples do kiss and stuff, just remember that under all this I am not a real girl, so don't go getting your hopes up too high!'
The converstation changed to what was on the TV, but when we heard 'Amy love, going now' instead of getting up and just saying 'bye then, see you next time' I gave her a full kiss on the lips, and she kissed me back. I felt tingles go down my spine as I realised this was my first proper kiss, not a stiff quick peck like I had had with girls at parties in the past. This kiss had emotion in it somehow, and finished with my sighing 'oh Amy' but all she said was 'better be going' and gave me a quick goodbye kiss before walking out to meet her mum at the front door.
I lay awake for quite a while before dropping off to sleep that evening. At first we had resisted the idea that we should lie in this a way. Amy being more resistent than myself, but we had both seemingly accepted the situation and Amy had learned to live the lie that she was a girl. We had moved on to living the lie that we were a couple, but that kiss seemed to have changed the relationship between us. I had from quite early on seen that Amy could be a good looker, even a girlfriend I would be proud to show off. It had been harder for her to see this and was seeing the friendship still as one of mates coping with a difficult situation. I know that I had pushed her into more and more girly things, but now had I pushed her too far, or was it the wine doing the talking. I woke in the morning, not really coming to any conclusions, but feeling that the kiss had been given and returned with equal passion, so why not pursue the idea of us being a couple, at least until the wedding?
That evening I called round and took Amy to a pub for more social exposure. I met a friend who did not know Andy while I got our drinks and made some lewd comment about my chances with such a good loooking girl. I said we were just friends, to which he suggested he might try and take her off me if I was not interested. We chatted about nothing in particular, until we ended up in silence. We parted and I went back to Amy.
'Last night'
'Yes'
'Did you mean what you said?'
'Yes, some of these clothes are lovely to wear'
'What?'
'Maybe not the high heels, but some of the satin, silk, soft cotton fabrics. I can see me wanting to wear them after this is all over.'
'Oh' this was new to me.
'You mean be Amy beyond the wedding?'
'Maybe not that, but at least wear some of these nice clothes. University can be a very open place for trying new ideas, don't you think?'
'Oh I had not thought about that, no, what I meant was last night when we kissed, well you kissed me back.'
'I did.'
'Why?'
'Err, because it felt the right thing to do, because I don't want to be found out, and if kissing will make the lie more believable, then we should kiss.'
'did you like it?'
Amy leaned back and considered 'I think it was a good one, once I kissed Lucy Lockhead, now she was good.'
'Pardon, you kissed Lucy'
'Yes, at a party last winter, she looks like butter wouldn't melt, but I tell you she can kiss.'
I took her hand 'That was not quite what I was meaning,. The kiss last night, I think we should do it more often, for realism if that is what you want to call it.'
'Ok Mark, if it means that much, then we shall kiss like a couple.'
After that evening, we spent less time together. Other things just cropped up that I should be doing, but it did mean that our meetings did become more like those of a normal couple. We went out a few times, we stayed in and watched TV, but the development of those days was our ability to kiss. Standing up, sitting down, lying down, we could cuddle and kiss for real. Well I was doing it for real, and I could not believe Amy was just doing it to please me, as she initaited the kissing sometimes. I was not sure but enjoyed it all the same.
With a week to go before the wedding, Amy was taken shopping by her mum for a suitable dress. Amy had worn dresses before and been out in the shops quite a few times, but this time was different. Her mum insisted on Amy trying on dresses in the changing rooms, no bringing things home and taking them back. From what I could make of the tale, the first store had been quite nerve wracking, but with each store the nerves faded until Amy was able to casually take the garment in and come out, show her mum how the dress looked and get her opinion, before going back to take it off. They bought a lovely grey and black dress that looked perfect on her.
I was given the money and task of taking her to buy some grey shoes, silver jewelry and suitable underwear. Amy by now was quite confident and could have done it alone, but her mum felt I should be included in this experience. We found some ridiculously high grey heels with a bow on them. Amy was not keen, but they were the only grey ones that matched the dress, so I insisted we take them. We found a small grey clutch bag to match, and felt we had made some headway into the list. Next we looked for underwear, and after my success at getting her to accept the heels, I pushed her into buying stockings. The bra and panties were white satin, a matching white suspender belt held up some delicate shiny stockings, which I hoped would look fantastic on her. Last, we bought some jewelry, a full set of silver 2" ear pendants, a neck chain with a similiar pendant that pointed down her 'cleavage', a delicate watch, a bangle and a couple of dress rings.
When we got home, her mum insisted on a full rehearsal and invited my mum round to make sure she approved. Our mum's never saw the stockings and assumed they were tights, besides that, both of them liked our choices. Told me I had better make sure my suit and tie are up to the same standard. Amy was encouraged to keep the dress on and pleased us all by mastering the heels quickly, and her feminine gestures, such as sweeping the dress under her as she sat. She even sat with her hands in her lap and put across a coy look at one time, then got up and wiggled her arse provocatively as she walked across the room to collect the wine bottle so she could replenish our glasses. This caused Amy's mum to whisper to my mum, but not quietly enough, 'I think I could get used to this new version of my child.' Amy looked at them, but it was hard to read her reaction as she just smiled and finished pouring, before mincing away to the kitchen with the empty bottle, then coming back to sit beside me. I took a nervous breath as she took my hand in hers. I was unable to read our parents reaction because I dared not look up and meet their expression. I did not need to look at Amy to know that the confident cockiness that sometimes got Andy into trouble was starting to re-emerge as she grew more relaxed in this new role. The last thing that happened to give our mothers something to consider was the incident that happened as I left with my mother. Mum went to the door chatting, but then as she turned to see if I was following, got an eyeful of us both enjoying lip contact together. Not a word was said though.
With a few days left till the weekend Amy, had to get her roots done and get her hair prepared for the event. She also needed something else neither of were aware of. She had to get her nail extensions filled as the false part had moved down the nail as they grew. Our relationship was also changing. Andy had been able to get me to do things in the past, and though I had been a lead partner in the making of Amy, Amy was now taking more of a lead. This was clear in the way we changed after we decided to make our relationship more credible with intimate shows of affection. I was enjoying my first proper relationship, which was more than a couple of dates. Amy I think, was enjoying it but also enjoying my enjoyment. A couple of times after that time we kissed in front of our mothers, we had some intimate moments and as we got closer, I became aware that I was stiffening in the trouser department. This had happened before, but what was significant this time was that Amy became aware of the effect our kissing was having on me, and would move so her body was pressing against mine. Then move gently so as to encourage my erection to grow even more. Two days before we were to go away, she placed her hand on the outside of my fly, squeezed it, at the same time slipping her tongue into my mouth. I was going weak at the knees when she released me.
'I think my boyfriend likes me.' she calmly whispered in my ear.
'How did you guess' I breathlessly managed to say.
'you have not forgotten that I am not a real girl.'
'No, but you look the part perfectly, I am just responding to the Amy I see.'
'I see, but most lads would want to at least think they could take their girlfriend to bed, and you can't.'
'I don't think about that, I just think of the girl, Amy, and how lovely she is, I am not thinking of sex.'
'I might believe you, except for this' she cupped my prick again, making it stiffen.
'Yes I know, but I also know you don't have girl plumbing.'
'Are you still a virgin?' this one was unexpected, I stumbled over the answer.
'I will take that as a yes.'
'Yes' I managed
'Has a girl ever seen your prick?' again I did not answer.
'So what if this girl took a look' I could feel the zip being pulled down and her long nails going inside my pants. I was beginning to breath rather heavily and having trouble knowing what to do.
'I think my Mark is enjoying himself' she kissed me deep and hard as my prick felt fresh air surround it.
'Now then Mark, something I don't think you have ever done before, and something I have never done before, but for the past few days have wondered what it might be like to do.' she paused and kissed me 'I would like to give you your first blow job.'
After much silence from me, I managed an 'Oh'
'Now I will do all the work, all you have to do is try not coming for as long as possible.'
'OK'
And with that she stooped down and licked my very sensitive tip. It twitched, then I felt licks surround the head. I concentrated as hard as I could, trying to stop the inevitable. Her tongue slid along the underside as she moved up and down a few times. It was so unlike any wank I had done, my whole body tensed. I held Amy by the side of her head and exploded into her mouth. I then crumpled as all the tension drained out of me. Before standing up, she licked me clean and tucked me back inside my pants.
'Well then Mark, that makes us something other than mates I guess.'
All I could think to say was 'sorry, I tried to not come, but it is so hard not too'
'it's fine, you did fine, no complaints here, as long as you have no complaints.'
'Oh no, no complaints, that was..'
'wonderful 'she completed my sentence.
As I regained some composure 'have you done that before?'
'No'
'I know that, but has someone done it to you?'
'Yes'
'and did you like it?'
'what do you think? I did it to you'
'thank you'
'that's alright, but I also wanted to see what it was like to have a cock in my mouth also.' said Amy
'and did you like it?'
'it was nice to give you pleasure'
'but all that spunk'
'part of the deal'
'but is it not gross' I winced at the thought.
'unusual taste and having it squirt down my throat was odd, but not unpleasant'
'not sure I could do it'
'not asking you to, remember I don't have one at the moment, but who knows if you ask me nicely, I might do you again'
She then kissed me, bringing the conversation to an end. I got a taste of my cum and did wonder if I would be prepared to have a mouthful of that sticky salty stuff in my mouth.
The next time we met, she made it clear she had no intention of being anything but the girl in our unusual friendship. It was an afternoon and we had the house to ourselves. She said she was practising wearing the heels, but minced about as provactively as possible, until we ended up kissing on a couch. I was soon getting stiff and she played with me until she had me sitting with my trousers open and her kneeling before me with her lips wrapped around my cock. This time I lasted longer, but as I wilted, she remained in position, licking and massaging my retreating erection. This lead me to think she actually liked giving me a blow job.
With one day at home before we left for the wedding, and while I was relaxing, Amy was busy going to the salon to get herself primed and prepared for the weekend. I had a meal with Amy's family, my parents there also, so no quiet moments on our own. It seemed our parents were happy with Amy's progress and the possibility of us making this lie work. I was working on bravado much of the time, and I am sure Amy was as well, but with the big day looming, we just had to be confident and go for it.
The next morning, we drove round to collect Amy. I could not believe the size of her case, she must have packed every piece of clothing she had. I had a suit and shirt plus a change for the journey home. Amy could have changed every hour! I did the macho thing and lugged the case to the car and found space in the boot for it. A boring ride across the country and we were there. My parents had booked rooms at the reception venue, so they could drink and not worry about driving and had booked a room for us as well. They told me singles are far too expensive, so they had booked a twin, which they assumed would be fine for a couple such as us to share. I could only smile to myself and hoped she never found out just how intimate our relationship had become. Once more the manly thing was to carry Amy's case, made a note that cases with wheels are much easier and would make sure I had one if travelling in the future. My parents handled their own cases with ease while I struggled with ours. I did get a 'that is sweet of you' and a kiss of Amy in a very HOT manner once inside the room, which clearly made up for everything.
I had never been to a hotel like this. Maybe the older and more experienced will have had a tv, kettle, fridge etc in the room, it just. It just seemed special, went about playing with everything, made a coffee, put the tv on a sport channel, while I killed some time before meeting my parents for an evening meal. If Amy had been Andy, I expect he would have sat on the other bed and watched with me, but Amy disappeared into the ensuite after unpacking her case. I did not really notice what she took in or how long she was in there, but she came out changed. Gone were the leggings and short skirt and tee, out came a girl dressed for going out.
The straight dress with fringes all over it looked great. She wore her silver jewelry and with the black heels and a black bag I had not seen before, asked if I was ready. I made some excuse about going as I was, as I did not think I needed to change. She then produced one of my shirts and told me it was a good job I had her to look after me, and a mum who knew what I had not packed. She then pulled my tee over my head and got me into the shirt, which she very slowly fastened up, letting her nails stroke my hairy chest. By the time she reached the last button, my trousers were tight at the front, then to add to my troubles she said.
'My Mark does seem to like me getting him dressed. I think he is going to enjoy letting me undress him later.'
My cock went solid and she had not touched me, just suggested what might happen later.
'Oh er Amy' I was all flustered 'what time are we meeting my mum and dad?'
'Plenty of time yet.' she said before bringing her lips to mine. She was in charge and doing to me what she wanted. Early on I had thought of kissing her when I was encouraging her to be more feminine, to walk with a wiggle, to get her hair done, to wear make up. Yes I at times had wanted to have her as my girlfriend, but only a few weeks ago I never imagined that Amy would be the one initiating a kiss, let alone teasing me with sexual favours. As we kissed, her fingers slipped down to me crotch and found the pulsing problem.
'You can't go to dinner with that, can you' unable to speak as she stroked a nail along the underside 'I think I need an apertif before I eat.' Knowing what was coming, I twitched and watched as she lowered herself onto my pole. I hung on like she had asked me to the first time, then let go into her mouth. We collapsed onto the bed.
We lay there together, 'Is that more comfortable?' she asked as she pulled the fly zip up.
'Yes thank you, not sure what my parents would think of us lying on the bed like this though?'
'What, with your cum all over my lips'
'Well, that as well I suppose'
'Better not tell them and keep the door locked.'
'do you really like the taste of spunk?'
'I am getting to like the taste more, what I do like is the pleasure it gives you.'
I could almost see her grin 'and I think you like having a bit of power over me'
'what you mean like I have your most sensitive body part between my teeth and at that moment you would do anything I say rather than get bitten. Well no, I do just like pleasing you, and enjoy the fact that I can make you react to me in this way.'
'I hope to equal that somehow, not fair just me getting there, I would like to make you cum if you would let me.'
'But you don't like the taste of your own cum.'
'I know, but for you I would do it.'
'That's sweet of you' she said as she turned to me and kissed me with her sticky lips, giving me a taste of what I had just offered to take a mouthful of. 'Come on, time to go and get some proper food. I shall do my lips and check my hair while you make your self presentable, don't want your mum thinking we are enjoying ourselves do we?'
Two hours later, after a nice meal and no hint that anyone had mistaken my girlfriend for a lad, we were back in our room and wondering what we should do once the door had clicked and locked behind us. Amy read my mind and while still standing in front of me, pulled the zip down on her dress, let it fall to the floor and stepped out of it. This is the point where my story started, I was looking at Amy and thinking how I had dreamt of such a situation, and now I was in one, all I could do was swear.
'Oh fuck me' I exclaimed.
'No darling, that is what you are going to do to me later.' she smiled and stepped towards me 'but first let's undo those buttons I fastened earlier.'
I swallowed hard, this had to be a dream, a half dressed girl is undressing me. I remember thinking how I was glad I had looked at those gay websites because this was not going to be anything like I had imagined my first time with a woman to be if you had asked me only a few months ago, but right now I was in no mood to reject the oppurtunity. All these thoughts went through my mind in a flash. I looked down to see long painted nails undoing another button, so rather than get in her way I put my hands on her hips and kissed her lips, working my tongue between them. Soon the awkward part of removing trousers occured and I had to sit and undo my shoes, leaving me sitting in my boxers next to Amy in her underwear. I rolled Amy onto her back and lay beside her while my cock continued to enjoy itself. We had been kissing and cuddling for what seemed like ages, when Amy asked.
'So are you going to?'
'Going to what?'
'Fuck me.'
'Oh I er you know, well, not sure how to ask.'
'Do you have some lube?'
'Well as it happens, I have.'
'You naughty boy, you thought you might get laid did you?'
'Don't tease, you are the one looking fantastically sexy, you could have just gone to bed.'
'I could, but where would the fun be in that. So you lube my hole and I shall do your cock.'
We played with each other for a while.
'I have never done this before, but I think it might hurt.'
'Funnily enough, I have not had any lads screw me before, but I want to know what it feels like to be filled my a man.'
I needed no more encouragement. I recalled those late night films of love making and got myself between her legs, then lifting them higher. I found her arse was more open, I pushed in and made her gasp.
'You ok?'
She recovered 'fine'.
I pushed in a little more, she gasped again, so I pulled back a little. She grabbed my arse cheeks and pulled me to her. Soon I was well inside and wanting to push deeper, she was beneath me panting I hoped in pleasure but it could have been to cope with the pain. As I pushed in and out a few more times, she arched her back and grabbed me so I pushed in deeper. Her panting got more excited as she buried her mouth in my neck before moaning something I thought sounded like 'ooohhhh Mark gooo ooonnn.' I was struggling to hold myself and just lost it, emptying myself into her. We collapsed onto the bed in a sweaty heap.
'My god Mark, that was incredible.'
'The first time is supposed to be difficult I heard.'
'No, that was just fine, you my boy, have just opened up a whole new world to this girl, I never believed sex could be so good. Now if you don't mind, I think I should get cleaned up and ready for bed.'
Ten minutes later she was back, makeup removed, clothes removed and wearing a short black nightie. Without hesitation, she lifted the sheets on the thankfully large single bed and slid in beside me. 'your turn now.' She was right I was sticky down there and I needed a pee so got up, returning to find her waiting for me, the sheets turned back, inviting me to join her.
That was possibly the worst and best nights sleep ever. I had never shared a bed before, and hopefully will never share such a small one again, yet at the same time I was close to someone who I had shared my first real sexual experience with, and would not have wished to be with anyone else. Morning came round and I felt dreadful. Amy got up and disturbed the other bed to make it look like it had been used before going and taking a shower. I was still amazed at how feminine my friend looked, even after a night in bed, her hair a mess, no make up and minimal clothing. What seemed like ages later, she came out in bra and knickers, letting me take a shower. Something else that amazed me was that even though she went in the shower first, I was ready before her. She had to dry and curl her hair, do make up, decide which dress and umpteen other things I had never considered before. Eventually we made it down to breakfast and joined my parents, the pleasantries of 'Have a good night?' Could have been answered in so many improper ways, but we both resisted and said 'yes, nice rooms' or something equally banal. I noticed another new twist to Amy, with a buffet style breakfast I could have a full english just like my dad, but Amy had cereal and a crossaint and ate it so daintily I was wondering where Andy had actaully gone. The wedding celebration started at twelve, so with a few hours to kill, I went to use the gym, but Amy and mum decided that it would be nice to spend some time together and help each other get ready, hair, nails that sort of thing they patronisingly told me in a way that made me feel unwanted,which I quite probably was.
By eleven I had sweated enough and went to get ready and suited up. Amy was already waiting for me, completely prepared but without the dress, not wishing to chance spoiling it. I went to give her a kiss but she moved away 'not a chance' I was informed 'took ages to get this make up right and you are not smudging these lips.' Half an hour later, I was in my suit and she was straightening my tie rather like I expected mum would have done, was that a female thing, straightening ties?
The wedding was pretty much like any other wedding, a ceremony to start with, lots of staged photos, women saying how nice the bride looks, some drinks then a meal, funny speeches sounding better because most listeners are drunk, a disco and more drink. That was the basic pattern this wedding took, for me and Amy it was slightly more involved what with the lie we were having to carry. The ceremony went fine, sat with my parents, said little myself, mum liked the dress and unexpectedly Amy chirped in with her own admission that she liked it as well, teasing mum by telling her if she got married her dress would be something similiar, maybe less lace and a higher neckline. I did not catch mum's response. The photos were fine as we managed to hide at the back of most. The meal was fine, Amy discovered she likes champagne. The more interesting part came later on when the dancing started. We had been doing the boyfriend/girlfriend part as best we could. I even had the odd dance with Amy, who was full of surprises as she had a slow waltz style dance with my granddad who was not in on the lie and told me I had a lovely girlfriend. She also danced with a few other girls that were there. I just did not expect her to know this stuff.
No, the real interesting part came from mum. We had all drunk enough to relax our normal limits on propriety, but it was mum who in a private conversation with Amy asked her how she was doing, how did she like living a lie. Amy had got over any nerves and knew she could carry this lie off, so told my mum she was fine and rather enjoying herself. 'I can see you are rather good and convincing, but as a lad how do you like having to spend time getting ready, the heels, those long nails you have, the patronising way some treat you.' Amy responded by teasing, I hope it was teasing, telling her how she loved the novelty of it all, the dressing up, the limitations of the heels and nails were worth it as they looked so good making her feel feminine, and what is wrong with getting a man to think he is superior when he will be nice to you. Mum also intimated that she thought we looked good together, like a proper couple. Amy really teased her with this one by telling her that was because we were a real couple. I wish I could have seen her face at this revelation, but I missed it, getting the backwash as it were when I returned with a round. Mum was looking at Amy as she got up, took my hand and lead me to the dance floor where she danced rather close and told me what had just passed between the two of them. I tried to say 'you didn't tell her everything' meaning the sex, but got a vague answer 'she helped set us up as a couple, what does she expect a couple to do.'
'Don't tease her too much, I have to live with her.'
'Only telling the truth'
'Maybe but I am not sure she is ready for that.'
'You ashamed of me?'
'No, of course not, I think you are smashing, I am just not sure how open minded mum is.'
'Open minded enough for this?' my lips then had a lipsticked pair pressed against them.
'Oh heck' or something more colourful went through my mind, mum is watching for sure. Grateful the song ended there, we broke and made our way off the floor, Amy to the toilets, me to face my mum.
'You having a good time?' I asked as I sat beside mum.
'Very interesting time.'
'Oh?' I was going to take this head on, alcohol reducing fear, and no common sense making this easier than normal.
'Yes I am not sure making Andy live this lie has worked out to be the punishment me and Mary thought it would be.'
'Oh' I was becoming repetitive.
'He seems to have taken to living as a girl rather too well, and seems to be enjoying the experience rather than being embarrassed and humiliated by it.'
'Oh' must try, um next time.
'Do you think it is going to affect him long term, I mean will he want to do it after this weekend?'
'Umm, not sure.'
'He just seems so confident. I know he was cocky before, but now he is just confident in a nice way, quite charming really.'
''Oh'
'Do you think he might be gay?'
I had a different answer for this 'do you think I am gay?'
'What? Why should that affect Andy?'
'Well he is as gay as me.' gosh that was some confession.
She looked at me with an expression I could not understand but possibly concern 'It has crossed my mind you might be gay.'
'Why?'
'No proper girlfriends' she paused 'that's about it I suppose'
'But I do like girls, they just don't seem to like me in that way.'
Then she sneaked in a trick question 'But Amy does?'
'We get on well.'
'And she fancies you.'
'What, no, that was just for effect.'
'No, she watches you, she gives you the attention, and she does a very good flirt look when she wants you to do something.'
'No she does not.'
'Whatever you say, but I think this has started something we never expected.'
'Like what.'
'Like you and Amy being a couple after this weekend.'
'Ask Amy, but I am planning on uni in a few weeks.'
'And she is going to do what.'
'no idea, fail to get good results we think and go get a job.'
'Not what I meant. I was thinking more that Amy will come to visit you from time to time. Would you have a problem with that?'
Quick, don't answer 'Would you?'
'Don't think so'
'Then it should not be a problem'
Amy turned up at this moment and came to sit beside me 'Mum reckons you can get me to do things with a flutter of your eyes?'
She looked across at mum before getting up and moving herself onto my knee 'Like your mum gets your dad to do things? I am learning.'
Smiled at mum, who smiled back, I just felt outwitted.
As if to prove the point 'I am getting hot, I fancy some fresh air.' she gave me a nice smile followed by 'you coming?' Before I had realised what was happening, she was on her feet and I rose with her. As we walked away she turned to wink at mum, I dared not turn round just in case I saw mum's grinning face.
To be fair, Amy was not just wanting to go outside to prove a point. No, she wanted some intimate cuddling and who was I to deny her the opportunity. I was soon displaying my pleasure from her attentions in a far from modest decent state my trousers were bulging in. I moved to return to the reception room but needed a minute to calm down.
'Mum thinks you might be gay.'
'And?'
'I said you were as gay as me.'
'I should think so, because we are straight, aren't we.' I could feel myself being teased, but let her continue.
'Well you know what she means.'
'No I don't, take a look around, you look like a bloke, I look like a girl.'
'Yes, but.'
'You are a bloke and have one of' she slid a hand down the front of my trouser re-exciting my cock 'these. Whereas I have a perfect flat' she took my hand and guided it to her pubic area 'front, no cock there I believe, can you feel one. And if I remember correctly, there is hole a little further back that you seemed to enjoy filling last night. So that makes me your girl, and you my man. So we are straight. Yes?'
'Put that way, then, yes.'
'there is a but there, isn't there?'
'Just what happens when Andy comes home?'
'Lets just enjoy today, because today I am loving not being Andy.'
'After all the hassle you gave me when I tried to get you to be more girlie, remember the heels, the pressure needed to get you to have your hair done, how you have changed your tune.'
'And not just the hair and heels. I love the way I look, the nails, the makeup and this dress is gorgeous. Have you noticed how many people look at me' I must have looked a little blank 'thought not, I have done it a few times now, get dressed up just to enjoy being looked at.'
'I never took you as that sort of person.'
'I am not really, but I have felt special today.'
'oh'
'And you have helped make it special, you have made me feel like a girl, and a desired girl at that.'
'I think we should get back inside.'
'Don't want mummy thinking we are doing something improper in the gardens do we.'
'No we don't' I tried to say firmly.
Back inside, mum was missing. My father told us she was getting tired and had gone up to the bedroom and that he was following her, now that he had seen us. I told him we would finish our drinks and maybe have another before turning in ourselves. Once out of hearing, Amy turned to me and asked if I was joking, another drink! Did I not want to see her underwear that night. We drank up, giving my dad a chance to get back. We did not fancy bumping into him in the corridors. There was hardly anyone to say good bye to and we were gone.
The bedroom door clicked shut behind us as we fell into the room. Our progress through the hotel had been frantic, a pause for a kiss here, a fondle on the stairs, an embarrassed giggle as we turned a corner, a fumble with the key while Amy is unbuttoning my shirt. My god, she was getting me excited. I made a move to grab her and just take her there on the floor.
'No, I want to do this properly.' she pushed me away and stood up. Then with a deliberate gesture, she invited me to stand with her. Her fingers soon worked on the remainder of the buttons, then my fly. I was stood in my boxers, which were unable to hide my excitement. 'someone looks happy.' She smiled then turned round so I could undo the zip at her back. I kissed her shoulder and let it slip down, creating a puddle around her heels. 'Now give me a minute to slip into something sexy.' She disappeared into the ensuite, coming out in the short nightie, her lips refreshed and scent reapplied. 'Are you ready Mark?' I just pulled the sheets back and invited her to join me. Within minutes, we had massaged cream into the right places and I was happily inside her hole and trying hard not to come until she did. I failed, maybe just too excited.
'Sorry I mumbled in her ear.'
'What for'
'Not getting you there'
'That is not necessary. I just wanted to feel you inside, making me feel like a woman. I wanted you to use me like you would a real girlfriend.'
I held her close 'but to me you are a real girlfriend' then I made an admission 'and I want to see Amy again, and to be honest, not that bothered if Andy doesn't come back.'
'You mean that, honestly?'
'Yes Amy.'
'Thank you Mark, you will never know how good that makes me feel.'
I knew nothing of post ciotal emotions or hormones back then, but as I lay there with Amy in my arms I felt as though I was in heaven, my girl in my arms her warm smooth body against my bigger hairy bulk. Bliss she wanted me and I certainly wanted her. I just lay there wishing that the night would never end.
It was not often that I went back home, I had done the usual thing from school, gone university not thinking what I was leaving, then the job with prospects and soon after a husband and a couple of kids and I was comfortable in my middle class suburban life with the occasional trip home to see my mum. Well on one of these visits I was out shopping with mum when I bumped into Alison, an old friend from college, she looked great, we said 'hi' and she invited me round for dinner that evening, mum insisted I go as we had nothing planned for that evening and I was not driving home till the day after, so I accepted.
It was as she walked away I realised I had nothing to wear, just an overnight bag and what I stood up in, trousers and a baggy top. I had to shop for at least a nice blouse. I found a nice gold oversize blouse which went well with my jeans and brown shoes. A good while spent in the bathroom styling my utilitarian hair cut and some make up and I was ready, mum said I looked great but next to Alison I had always felt dowdy. But for old times sake and we had been great mates in our teens I did not cancel just because I knew she would outshine me.
Half seven and I am stood on Alison's front step being invited in by someone I was not expecting to see, another woman.
'Good evening, you must be Kate. My name is Julia. May I take your jacket. it has gone a bit chilly this evening.' I shrugged my jacket off which she took. 'I'm sorry but Alison sends her apologies, please come in. What can I get you, tea, coffee or something stronger, there is a pinot Giorgio in the fridge or there is vodka, rum and baileys in the cabinet?' I followed her through the house to a conservatory on the back. The house was immaculate, a virtual show house. I plumped for the wine and made myself comfortable in a chair while Julia went back to the kitchen to check on things, returning every few minutes to give me an update on where my host was.
I had chance to take a longer look at Julia as she flitted in and out, slim, not that curvy, no bum and small up top, but looked great in a plain grey sleeveless dress which was clearly tailored to fit her, a nice long bob cut which turned in perfectly as it reached her shoulders, great long legs and grey peep toes heels on her feet, I was surprised at the length of her nails given she was doing so much cooking, but she looked great and I had to think, maid or girlfriend. You see me and Alison were not just mates we had a teenage crush. We went through high school together as mates then at college we still saw each other though I did A levels and she did a vocational hair dressing course. And one day she found me upset after a break up with a boy, and somewhere in her comforting me we kissed, and that was it, until I left for university we had six months of being very intimate friends and no one knew because we linked arms like girls do, could kiss as long as it was toned down in public, but in private we learnt what a woman likes.
After ten minutes of looking through Alison's cosmo magazines I heard the front door open, a muffled conversation followed by a flustered host who came in full of apologies, we greeted each other with a kiss on the checks though I had wondered if she would go for the lips, and I half told myself off for thinking she might seeing how I am a happily married mother now. She left me saying she needed to change and freshen up, accountants offices always leave her feeling grey. I honestly thought she looked good in a cream suit with a green satin blouse beneath it, the high collar looking very no nonsense, the cream stilettoes striking another image of a sexy self assured woman. It did not matter what I thought as she hurried upstairs calling 'Julia have you a minute.' Julia followed in her wake.
Five minutes later Julia was back in the kitchen and my friend reappeared, hair down, suit changed for a calf length silk dress which somehow managed to float around her and cling to her every curve at the same time, and if anything her heels were even higher. She looked fantastic and in five minutes, I only wish I could change my shoes in that time!
This time the greeting was less formal, a real hug, I could feel her breasts pressing into me sparking long forgotten lusts in me. We did the usual you look great, no you look fantastic female routine, Julia brought Alison a glass of wine and topped mine up as she sat beside me holding my hand and inviting me to tell her all about my recent history. We chatted as we moved to the dining table where we were served with a salad starter, then a seafood pasta. Julia being attentive to our needs being there when required but absent for most of the time. Alison told me about her chain of beauty salons she owned, she was not just a hair dresser, they did everything including a part share in a country spa for real pampering. I was feeling rather outclassed by this elegant, clever, successful business woman, my civil service job with easy hours and good pension seemed dull next to her.
Julia came and took the pasta dishes away, topped up the wine which I tried to refuse but was overruled as Alison told me Julia could run me home later as I was already well over the limit. I accepted but followed it up by enquiring about Julia's status in the house, suggesting I did at first think she might be her partner but thought that unlikely as a girlfriend would have eaten with us, and then I got the most interesting story I have possibly ever heard.
'It started quite innocently' Alison smiled at me 'Julian was a stylist in my city salon, we get some real classy women in there and they are not shy about letting you know if they feel the job is not right. Well one day Julian (who is Julian I thought) cut this woman's fringe too short for her liking, there were words and Julian left in a flood of tears. The woman calmed down after an offer of complimentary treatments, then I went to find Julian who was hiding in the rest room. He was not the best stylist to be honest and I prefer to employ women but he was gay and camp which some clients like so I had hired him, but now I had a wreck, deeply upset who it seemed was not that distressed by the fringe woman but by the fact that his boyfriend and he had had a big row the night before, Julian had stomped out, followed by the boyfriend locking him out and Julian sleeping in the shop overnight. I did my best to calm him before telling him to take the rest of the day off and go home. Well an hour later he was back unable to get in, the lock was changed! that was quick.
So I had one homeless upset gay man in the salon with no idea what to do. As you know it is not unusual for gay men not to have a great relationship with their parents so he could not go there, he rang a few friends all of which distanced themselves from him and for fear of this boyfriend, all refused to put him up. In the end I offered him my spare room for a couple of nights until he got himself sorted.
Grateful comes close to his reaction, after giving him a key he took himself off, later calling to ask when I would be home. I got home about my usual time to a house full of cooking smells and a rejuvenated employee. He had also cleared the rubbish of several take-aways and done the pots. The food was every bit as nice as what we have just eaten and though I would never have a man stay overnight, Julian was such a non threating person I had no misgivings about letting him stop.'
It was about this time, Julia/Julian came in with a sorbet dessert and liqueur, the person could be a fella but why and how did he end up in a dress? Alison was about to tell me.
'I love it when there are guests the food is always divine, if I had been on my own we would have been out in a busy bistro or some place and this is so much nicer isn't it? Anyway where was I? Oh yes a homeless gay stylist who come the next morning was up early making my breakfast wearing a dressing gown he had found on the back of the door, big fluffy white one I think, his face mess of red eyes and bags under the eyes. I told him he looked dreadful and we agreed he should not go into the salon. So I left him to hopefully get himself sorted and a place to stay, but as you can tell that did not happen, I came home that evening to another nice home cooked meal and an even camper cook. He admitted to doing some cleaning and found a bag of charity shop clothes, and in his words had nothing to wear while his were in the wash so he borrowed a few things, like a cerise blouse he wore that first evening, the full sleeves were definitely not manly even on a camp man. We had a chat over his meal and I agreed to let him stay until the weekend when he would hopefully have found somewhere to live. Two days of nice dinners, I could go with that.
Well the house got cleaner and tidier until I hardly recognised it after it being such a neglected mess, and Julian was enjoying my cast offs, a white silk top the next day, and on the Friday a plain black tunic top. By the Saturday evening he was in his own clothes but stressed out completely, a day of flat hunting and calling even more friends had resulted in nothing and he was worried my welcome would end, I was out on the evening and told him we would sort something on Sunday. So on the Sunday with us both sat in dressing gowns drinking one of his lovely lattes I came to an arrangement with him. He did not want to go back to the salon, the women were too stressful he said but he had enjoyed his days cleaning and cooking for me, so what I agreed to was that he could stop a while longer till he got himself a flat and a new job, in the mean time he would do all the housework, sort out the garden and have a meal ready every evening for me getting home, this I knew he would agree to what surprised me was that he also agreed to my other rule, no men in the house which included him. He was not to invite any of his gay men friends round and though I did not feel threatened by him as a precaution and a test of his resolve to stay I informed him that he would have to be locked in a chastity cage.'
My mind was racing with this bit of the tale, surely he could just say no, I understood not wanting a man about after the things she told me about what her 'uncle' did to her, but surely locking a mans bits up is extreme. I am sure my face showed surprise when she said 'He took a moment to consider things before accepting my terms. I doubted he was the masculine one in any relationship but I did not want to find out if he had desires to be a man with me.' Gosh was all I could think he is cuckolded I thought they were just a fantasy thing, men being locked up, cant think my Roger would go for that. But I needed to know how this wimp of a man ended up looking so perfect as a woman. Alison continued.
'I was quite liking have the house kept for me, no cleaning, gardening, shopping for groceries, just a nice clean place to come home to. I hardly noticed after the first few things he borrowed from the charity bags but after a couple of weeks he was wearing some tight white jeans and another time a pair of loose linen trousers, as well a selection of my old tops. Then one evening over dinner I asked why he had not made an effort to retrieve his clothes or buy some new ones. I was shocked to hear that as well as being locked out, so unable to get his clothes, the ex boyfriend had his bank details and emptied his account. I told him I would have a word with one of my clients a lawyer who dislikes bullying men, only took a few weeks and a couple of letters and he had his money back, but in the meantime his choices were becoming ever more feminine, loose tops, pastel colours, you know what I mean. Then one day I gave him a packet of tights and told him to try a skirt as it was about the only thing I had not seen him in, he suddenly went coy on me and asked if I minded him using my cast offs, I assured him I was fine with it just so long as it is only cast offs. The next evening he was in a longish flared skirt but his shoes, a pair of deck shoes, looked out of place, so I explained how skirts take a nice shoe to show the leg and ankle off. Later that evening he was looking through some fashion magazines. Two days later a pair of low heeled courts arrived in the post and the real start to his feminine development began.'
'He only bought online and kept it simple, trying out things to see how they looked and felt. He was still mostly in trousers and when shopping, exclusively in trousers and plain tops, but the skirts were more common. His hair already long was styled by himself into some very pretty shapes, but when make up started coming in with the supermarket shopping and his lips were changing colour as well as his eye lids I decided to give him a little push. I have a policy that before I take on a new range I send someone to a salon that is using it, they report back on their findings. Spray tan was the last one and the product did not live up to the sales pitch, had to give Heidi extra pay and detanning after that one. But at the time I was being pressured into taking on a new nail range, tougher, longer, stronger, they were supposed to be the best, but everyone who wants long nails already had them so who to send, you guessed, Julian. I asked him if he would do it, he said yes, I think he felt he owed me and this would be a small payment, so I explained how he would have to go to this salon across the city, and no man would go in for nail extensions so he would have to go looking female. To be honest there was a moment of hesitation then, but he nodded before asking if I would supervise him doing his make up before he went. Off course I would, I was curious to see just how feminine he would look.'
'And I guess he went through with it?' I asked.
'He most certainly did. We made the booking, I went into work late after making sure he was looking just right, he actually had quite good skills, said it was being in the salons for so long you just pick stuff up. Well he left the house in a skirt for the first time that day, some nice new heels, I think he was doing 3" by then, and off he went. To be honest I did not think he would go through with it, he had to look the part first, then he had to walk out the door which I guess was a big thing for him, suppose a neighbour saw him and guessed, how embarrassing, and then there was going into the nail bar and staying in character the whole time, and worst of it was I had lots of meetings lined up for that day so it would evening before I saw him again and would find out if he had done it. And yes you are right he did go through with it. I got home that evening to a nice meal and my housekeeper sporting the most incredible set of nails. Shocked I was but could not help myself I had to ask about the products while all he could talk about was how do women do things with long nails, he very nearly cut the end of one while chopping a carrot.
It was the next day the true reality of what he had done dawned on him, these nails were almost impossible to remove without damaging his real nail underneath, and part of my product testing is to see if they are as strong and long lasting as was claimed. He had them until they grew out which would be weeks, possibly months. His calm response was to go out and buy some more make up and few packs of tights. I could not believe he accepted living as a woman so simply.'
'And now, does he ever try to be the man?'
'God no, one of my rules, no men in the house remember. He if a fulltime cross dresser now, been out and bought clothes from stores while dressed, he went back to the nail bar to have the tops filled every few weeks. He just fell into being Julia from then on, I treated him to the grey dress so he could have something that really looked classy on him.'
'So he does everything as a woman, the shopping, the gardening, everything? And he does look so convincing I thought he was your latest girlfriend when I first saw him.'
'He would be flattered by that, but no he does the housekeeping, we do not share a bed as well, I know he would probably go down for me but there no attraction in a person with his bits, I like a nice clit.' She gave me a wicked smile 'and he just has the one hole.'
I was still digesting Julia's history as Alison told me about her love life or lack of it, her success it seems puts other women off getting close so she has one night stands and a few friends who share her desires. I asked if Julia has any sex now, assuming he was still locked up, more than her it appears, there are plenty of blokes out there who love dating him and know that under his skirt is a locked up cock, but I don't suppose that bothers them if they are gay does it.
Well past midnight and few more drinks later and after refusing to share Julia's bed, not because I did not fancy it but because I could not think how I could explain to mum why I had stopped out unless I lied, and I am a rubbish liar. So Julia as promised by Alison drove me back to mum's.
The next morning as I was recovering from my unusual amounts of alcohol and thinking of getting a taxi to run me to Alison's so I could get my car and go home, Julia turned up on the door step offering to run me there, apparently she had offered last night but I did not remember. I was bowled over by how feminine this person was yet again
Shiny black leggings, a long top that would pass as a mini dress in a night club and heels that Roger would love me to wear but I would dread, they were so high but Julia walked with ease in them.
I accepted the offer of a lift feeling dowdy in my baggy top and jeans sat beside her.
'You off out somewhere later?' Not believing anyone got so dressed up to run errands.'
'Not really, some groceries to get that's all.'
'Alison told me an interesting story about you last night.'
'I wish she wouldn't, and you want to know if it is true?'
'Well you do look all girl to me.'
'Well, why should she make up a story like that about me if I was a girl just having a hard time, or do you want to cop a feel of my groin and see if that confirms anything.'
'Sorry I didn't mean to offend, but you are so pretty I actually thought you Alison's partner.'
Julia blushed 'no that is one thing I am not, you an the other hand, she fancies you something rotten.'
'But if she asked would you?'
'You are very cheeky you know, but the answer is yes, I owe Alison loads and if she said Julia I want you to do anything, you know I would probably do it.'
'Being cheeky then, do you ever take the chastity off?'
'When she is away o business or holiday.'
'But your boyfriends?'
'They find it amusing and gets them all the more excited thinking I am cuckolded, but it never worked well so I don't miss it. Now here we are back home and I hope you have a safe journey home, and somehow I expect we shall be seeing each other again, I am sure Alison wants to keep your friendship alive.'
I gave Julia a hug and kissed her cheek, the scent was lovely and nearly asked what it was, but smiled and said good bye to a most interesting person.
It only started with me sitting waiting, all ready to go out and Fay looking great as she fastened her ear rings on. An idle comment can have major consequences. I only said 'your dress looks great, those underskirts that make the skirt fill out are back in fashion, they always looked good in those old films.'
Fay smiled at me, 'yes it's new, I bought it last week, glad you like it.'
And then the comment that changed everything 'what does it feel like to wear? I mean the skirt is so full and the underskirts must feel different against your legs.'
'It's hard to say because you wear nothing like it so there is nothing to compare, I'll tell you what, if you are really good to me tonight I will let you find out for yourself.'
Now when Fay suggests I be good it is not a warning but an encouragement, meaning that she was feeling randy and wanted to enjoy the evening to the full, with more fun when we got back home later.
At two in the morning I was exhausted and so was Fay, we fell asleep the comment at least my on part, forgotten.
It was early afternoon before we were both up and functioning properly, and we both happened to be in the bedroom when Fay was sorting out her dress from the night before.
'You still curious about how this dress feels?'
'Oh er yes I suppose so.'
'You don't sound so sure as you did last night, you aren't frightened by a dress?'
That did it, I was no coward 'Well go on then lets give it a go.' and I lent over to pick the dress up.
'Not so fast, you don't just put a dress on, you need to sort out the preparations first.'
'Like what?'
'Like you need a bust to fill the top, and then some nice tights or stockings always make a dress feel better.'
'Oh come on I only need to put it on to know how it feels.'
'You are so wrong, to know how nice this dress is you cant just put it on, its like looking at a motorbike, sitting on one and riding one. to just put it on would be like sitting on your bike, no if you are going to know how nice this dress is then there is no way you are just putting it on.'
'Ok so I get the bike thing, what do you actually want me to do?
A long lingering kiss happened before Fay told me. 'I want you to just do everything I tell you to do, no questions, no being awkward, you be good and I am sure you will like the results.'
Resigned to it now 'ok what's first?'
Soon I was in the shower rinsing off her immac cream and watching my body hair going down the plug hole, I wanted to ask if it was necessary but when I dried myself i knew the answer, yes it was, my skin felt so different, sensitive and smooth, even more so after I moisturised. The satin wrap she gave me felt amazing now as I made my way into the bedroom, I thought that it would be put on the dress next but she guided me to her vanity and made me sit down. 'Now remember be good for me.' she repeated and then plucked a few eye brow hairs out, 'just needed to be a little neater, now lets see what features your face has.' She skillfully brushed powders onto my skin making me feel pampered, next she surprised me with some of her special evening underwear and told me to put it on, knickers were no problem besides getting my stirring penis to settle inside, the bra was trickier so she came round my back fastened it and kissed my neck 'you look great already.'
'Pardon'
'Just wait till you get the dress on.'
From somewhere she produced a wig and secured it over my neat manly cut, brushing it into a style she wanted before spraying it with lacquer to fix it. Next rolled up tights pushed into the bra cups gave me a chest I had never had before. I could sense that I was looking more female with every action, but it was as I rolled the first stocking up my bare leg that I actually felt how nice this was, the second confirmed it and the tensioned suspender running over my arse just helped me along.
'You seem to be liking this' Fay smiled as she looked down at my extended knicker front. I dared not answer because I was not sure I should be reacting this way even if the evidence was there for us both to see. 'Nearly there.' She handed me the underskirt showing me how to step into it, my first skirt of any kind and I was not having a problem with it. 'Ok before you get the dress just a few small extras, and then we let you find out what this motorbike is like to ride.' A squirt of the scent I liked on her was evaporating from my skin as she clipped some pendant ear rings to my lobes, those hurt. 'I hope these fit, they are a bit big for me but you are not that much bigger than me, are you?'
'Heels?'
'Yes heels, it would be like riding without your boots, it's part of the package.'
They were tight or snug depending on your point of view. 'Right you ready?'
'As ready as I ever will be.'
'Lift your arms and put them through the sleeves while I stop it ruining your hair.' She carefully maneuvered the dress down my body until it was sitting about right, then with a swift action I felt the zip rise up my back and pull my stomach in. A bit of fluffing out of the skirt and a necklace hung round my neck, she took a step back and smiled, 'oh silly me I forgot lipstick.' Carefully she applied the nice cream to my lips. 'Now come over here.' she took my hand and lead me to the full length mirror we have, the skirt was swishing round my legs, my free hand was caressing the smooth skirt as it moved. 'Now I think for a first time, you look rather good as a woman. Tell me how does the dress feel?'
'Er. I. Er. It is very different.'
'Obviously, but how does it feel, smooth, rough, tight, loose?'
'The dress is very nice and smooth, but you know I like your silk clothes, the underskirts feel like they are brushing my skin ever so gently.'
'Ok so walk about a bit and feel it moving.' I walked to the door and back, taking another look in the mirror watching the skirt move round me 'So you know how it feels, what I want to know is how it makes you feel, because you look amazing.'
I thought for a moment 'well the heels make me feel a little awkward, but I certainly feel different.'
'Nice different or unpleasant different.'
'Nice different.' I confirmed.
'Well in that case might I suggest we go downstairs and get something to eat and maybe watch a film.'
We ordered a Chinese and ate it with a bottle of wine, Fay remarked how nice it was to spend a night in with her girlfriend and how it would be nice to do it again, but next time both of us getting dressed up for the occasion. I just smiled and picked up another piece of chicken, thinking 'next time! does she like this?' We relocated to the sofa and watched some mindless rom com letting the wine relax us until it finished and Fay came out with another comment 'I know you like skirts because it allows easier access to my pleasure zone, well how does it feel to be in my position?' as she spoke she deftly slide her fingers up the inside of my thigh. 'Someone is enjoying themselves.' she said stating the obvious as she hit my pleasure zone and pressing her lips to mine, ' I must teach you how to do lipstick, yours has all worn off.'
'Is that necessary?'
'Oh you have so much to learn about what wearing a nice dress involves.'
'Do I?'
'And one thing to learn is just how sexy a dress can make you.'
'Oh' I was not expecting that.
'Not sexy in the way the usual way, no you make me want to take you not you taking me.'
'What?'
'Oh come on, sexy woman that you are, I want you to be a sexy woman in bed now.'
This was getting out of my comfort zone, what was she suggesting. Then I discovered that Fay was not quite all she had lead me to believe, before we met she had enjoyed other women and assured me that I had got her randy, my next revelation was that hidden at the back of a drawer was a toy she had not let me see before, and until later that evening I had not known about. She left me to tidy up the glasses and plates before I followed her upstairs.
I was already aroused by her earlier attentions and to find her in seductive clothing only encouraged me, I started to get undressed but she soon put a stop to that and showed how it is to be made love to from the other side. I was aching to go inside her or for her to touch me but she refused and massaged my rear entrance instead, slipping a finger or two in, which I admit to quite enjoying, there was a brief pause while she said she wanted to introduce a toy, which is when I discovered more of her past and something of my future. She rolled over to face me once more only this time she had a cock to rival mine between her legs. 'on top or from behind?' she gave me no choice as to whether or not I wanted it, she was going to enter me one way or another, and I was putting up no resistance to her advances.
Half an hour later I was removing my make up and putting soiled clothing in the wash. My outer appearance would soon resemble the person of the night before, however the inner me was changed forever, I had enjoyed wearing a dress, looking pretty, being sexy, I had even enjoyed Fay fucking me until we both came in a fantastic orgasm. I would certainly be having more girls nights in with my girlfriend.
A common theme, drunken dare turns into something more!
Thanks go to Tiffany for checking through. So don't blame me for the mistakes :)
It was funny how it started. We often had a meal together the six of us, that is three couples, each couple brought a sweet or starter and the host cooked the main. We usually drank plenty of wine and generally had a good time. What was funny about this meal last summer was not funny at the time. Our friends Mark and Kath had brought the sweet and to be honest it was inedible, well it would be if you put salt instead of icing sugar into anything that is meant to be sweet to taste, well Mark went off on one and Kath got upset, the whole evening looked like it was going down the pan, that was until Sara my wife defused the situation by offering a daft solution. That solution was meant to get Mark off his high horse but did a little more than that in the end. What Sara proposed was for the men to cook the next meal, it was our turn to host, so I would cook the main, Mark would make the starter and John the sweet. There was a general agreement to this especially from the women, that was until Kath (still smarting from Marks tirade) suggested that just cooking was not enough, they should be required to make themselves look attractive as well. By the end of the discussion the women had decided that in a months time we would have another get together, and the whole evening would be a turnabout night, essentially the men would cook and dress as the women had that night and the women would do what ever us men had done. We joined in with the idea because we were drunk, the idea sounded like fun and we, that is the men, thought it would all be forgotten in the morning.
How wrong was I. The morning was a slow tidy up and read of the Sunday paper followed by a walk in the park. It was here that Sara recounted the evening before, first with 'What are you going to cook for us?' then after some thought based around a pasta meal that I could reasonably produce came the bombshell 'What are you going to wear? I'm going to wear your tuxedo' To say I looked at her in stunned silence would be no exageration 'Well we are about the same size' seemed to be the final word on the subject. At our next get together Sara was going to wear my suit and I would be wearing something of hers. Now here I should explain we used to be in an amateur dramatic society and were used to dressing up and playing different roles, but we had never played each other as it were.
The rest of the walk was quiet as I tried to work out how this could be undone or at least minimised, but by the evening the girls had been talking and it was, as far as they were concerned a done deal, it was going to happen, and when I meet Mark in the pub later had to agree we were rather well stitched up. There seemed no way out without big trouble and managed to talk ourselves into believing it would be fun.
Again how wrong was I. Sara decided that at least I was going to do this turnabout thing properly, even if the others did not. She began by pointing out how Mark was six foot, John was a broad rugby player, whereas I was a five foot six bloke who has trouble finding trousers with a small enough waist to fit me, so I at least could look like a feminine female even if the other two ended up looking like men in drag. I tried to dispute her statement by explaining how my body shape was wrong, simple to alter with padding. My hair was too short, she had a wig. I don't know the first thing about her clothes besides how to get them off her, she laughed at that and then told me it was time I learnt. She thought the first thing I should learn was how to walk in heels and took me to the second bedroom we used as a dressing room. She picked out a mint green chiffon dress which she had worn to the christmas does the year before and made it clear if she was wearing a tux, then I should compliment her. I had to agree with the logic but could not help thinking the logic was flawed. Her cream shoes were too small for me so I hoped that was an end to the idea, 'Don't worry, I will sort that tomorrow while you are at work'
I came home the next day to see a pair of cream shoes waiting for me where my slippers should have been. 'Do you like them?' there was a pause as I tried to think of an answer, but before I got there she chipped in with 'Well put them on let me see if they fit' I sat by the front door and took my shoes off, then my socks once I realised they were too bulky, then slid my feet into the ladies style shoe. Sara came to meet me 'How do they feel'
'Snug' meaning a little tight.
'That's how they should be, they wont slip off........ good. Now try standing'
I stood up and had to hold on the chair while I found my balance.
'Now you see why you can't just put heels on a hope to do them justice, you need practice. Come through and help me set the table and serve dinner'
I followed rather cautiously not wishing to fall and hurt myself, then with cutlery in hand I managed to get around the table and set our places. It was a relief when I did not have to carry hot plates while wearing the shoes. She teased me into keeping the heels on all evening, and much to my surprise did get better at walking in them. I soon found out that any evening when I came home straight from work she felt it would be good for me to wear the heels for good practice. What changed over the week was that she began to give me tips on how to walk. 'Imagine there is a line, and put one foot infront of the other' or 'Heel then toe' and 'Stand with your feet heel towards the instep'. It was not just advice there were plenty of compliments as I improved, which helped boost my flagging ego.
My femininsing took little steps every day it seemed to me. If I was home for about six then Sara would want to try something new on me, or at least practice what I had learnt the day before. So after a week of walking in heels, I then spent a week of free evenings wearing a skirt so I got used to wearing something other than trousers and became familiar with the - what I felt was excessive material. I am sure she picked the largest, longest most floaty skirt she had for me to try on. Again I surprised myself and was soon sweeping it under my legs as I sat down, smoothing it out as I sat, and making sure it was straight when I stood up. She even had me admit that it moved better when I wore heels than when I was barefoot.
That weekend I practiced making the pasta meal. I had to admit that it was very nice and Sara even flattered my cooking suggesting I do it again on the Sunday. Only that time I was to do it wearing the skirt, heels and a blouse, then when I started she added an apron so I did not splash anything on her clothes. I coped quite well with the added hieght and clothes which were not as practical as my own. But the meal was possibly nicer the second time round as I adjusted the herbs to taste.
My next week was to include the wig, a shoulder length 'Jennifer Anistone' I was told, what I did find was that whenever I lent forward the hair would hang infront of me, I only put it in my food once, but it seemed to be in my mouth countless times and in my eyes on numerous occasions. Sara showed me how she dealt with the hair in a ladylike fashion, then encouraged me to follow her example. Mid week she changed the skirt to a mini which presented new problems of how to keep things looking decent and I learnt the art of crossing my legs and pulling the hem lower when I stood up. The mini did cause me to ask why, when the green dress was knee length. So I am familiar with as much about being feminine as possible, which I found out that night was to sleep in a silk nightie, while she slept in my cotton T shirt and boxers. I told her she looked very sexy, she said I was more alluring than sexy but managed to get me to stay in it for the night after we had spent our last energy doing bedroom gymnastics.
The last week came and when I got home early, it was straight to the bedroom, change completely, skirt, blouse, underwear including stockings 'might as well have you sexy' she said, wig and as the week progressed, nail manicures, some eyebrow neatening up and to my deminishing male ego anther big step, complete depilation except for my curly bits which I shaved into a neat V. Then before bed a routine of creams to help make my skin softer and better hydrated, whatever that meant.
On the Friday night we had a full practice dressing up, Sara put on my tux and gelled her short hair back into a dramatic male style. Then it was my turn, underwear, the chiffon dress with it's acres of soft fabric flaring out from my hips, the soft round neck hiding nothing of the extra large chest I now had thanks to a padded bra and the long loose puff sleeves with there long cuffs made me feel even more odd. Sara then put a towel round my neck and proceeded to apply all sorts of cosmetics to my face until she was satisfied with my pink lips, cream and brown eyes, all adding to the base of foundation and blusher.
I had got almost used to seeing myself in some form of femininsing attire, but to see the whole thing was more shocking than seeing Sara for the first time in my tuxedo, she looked strangely masterful and handsome, whereas I just looked like a very well turned out woman. Sara said I was pretty, but one thing was for sure, I was not looking at all manly and after all those evenings spent practicing, I even moved and stood like a woman once I put the heels on. There had been a stew slowly cooking in the oven while we had transformed ourselves, and all that was left was to set the table and eat our meal, Sara encouraging me to take the female role and set the table and serve her while she opened a bottle of wine. Later on after we had finished the wine, and I had been shown how to clean myself up before going to bed, Sara once more in my bedclothes made love to me saying the whole turnabout thing was quite a buzz.
The Saturday of the gathering was an unusual day. Sara insisted I had to do all the food preparation on my own and I had to do it in my feminine style. She left me a plain biege dress out for me to wear during the day but first I had to go through a list of what she called 'getting me in the mood' things. A bath with scented oils after I had shaved my body just incase any hair had been missed the last time. Then I washed and dried my wig while still on my head which took ages. This was the first time I tried to do my own make up and it was not too bad, but Sara did take me for a touch up when I appeared very late in the morning. It was also the first time I wore a pair of control pants to squash my little man out of sight as the dress was rather too well fitted for a male bump to be showing. Last thing I slid my feet into my heels and presented myself before her. She said she was pleased with how I looked but before I could go and make her lunch I needed a few touches to my make up and as a 'treat' she glued false nails over my own then painted them a pink that would match my lips later on.
How I did not feed her some part of the false nails in her lunch I shall never know, they were so disorientating, but with care I made lunch and settled down for a bit of a rest. Sara had other ideas reminding me that she usually does the washing on a Saturday and gives the kitchen a good clean, for her part, she was dressed in jeans and a loose jumper of mine and told me she was going to try and understand how an afternoon spent watching football could be fun.
I did the washing, then cleaned the kitchen and after a short rest prepared the ingredients for the main I was cooking. About six I reckoned I should go and get changed into the green chiffon dress that was to be my evening outfit. I had to fall back on a phrase Sara had used in the past 'Darling, could you come a give me a hand' I found it impossible to pull the zip up fully and the small cuff buttons were so hard with my long nails I had to ask her to help me get dressed. but she approved of my make up, a little more blusher, bolder more defined eyes and creamier lipstick. She offered me her pearls, a single strand for my neck, long drop clip on ear rings and a bracelet to match, then her watch and a spray of scent. It felt wierd when I was told I looked beautiful.
I watched as she got dressed in my clothes,amazed at how her chest disappeared in a sports bra and her trousers bulged as she fixed a pair of rolled up socks behind the fly. We chatted about how we were going to play this charade and came up with the idea to ham it up, she would be as sexist and overbearing as possible, I would be the dutiful little housewife, she would welcome them at the door, I would take their coats and offer them drinks and get on with the cooking while she just stood around chatting. When I said that was nothing like our normal roles she said it would be better to go over the top and make our characters almost cartoon like. I agreed but felt I was getting the harder part of the deal.
Mark and Kath came first, Kath in a very nice lounge suit I later found out she had hired, Mark was wearing a trouser suit Kath had bought for him from a charity shop, the suit was a nice grey, but he was so tall it fitted badly and he looked ever so uncomfortable. John and Mia turned up last, Mia in a sport jacket and plain trousers her long hair tucked inside a cap, but John was so broad he looked like a comedians send up of a woman, again his dress was nice but on him looked wrong. I could not help thinking that I was the only bloke amongst us who looked like a half decent woman. As the evening went on, the wine and beer was drunk, I became the focus of discussion, it was noted that I was a good cook, as were Mark and John I pointed out, no they weren't, they had bought theirs and just put it on plates to carry over. I was the only one wearing heels, well the other two had such big feet, it was still noted how well I walked in heels, and all the fussing over my dress, and the long nails. It all added up to make me look like I had been too keen on this turnabout theme. Sara was also seperated out for special consideration as she was the best dressed man there and was asked why she was being so sexist and domineering towards me, she defended herself saying it was for effect, then turned to me and asked 'Do you have a problem being my little wifey. Darling?'
Almost automatically I replied 'No dear, does anyone want any more wine?' playing the host just as I had been doing all evening. Then as I went round the table with the bottle Sara stroked my stockinged leg.
'The perfect wife, can cook and looks fantastic, what do you reckon boys?' then gave me arse a slap as I moved away blushing. The other women were looking at each other and distanced themselves in some way that did not involve actual movement but was clear to all that they were not agreeing with Sara. I continued to play the female host but Sara calmed the domineering husband down and we ended up having a great time even sending me up when I did something overtly feminine like smoothing the dress under me as I sat down.
The evening came to an end and for some reason I never did fathom I found myself sat at the dressing table cleaning off my make up, wearing a long silk nightie and wrap, just like I had on previous nights when I had worn make up and Sara suggested I would feel more in character dressed that way. It seemed Sara was only to happy with this last moment of role reversal as she made it clear I was still her little wife and as such would satisfy her needs. Which to be honest was not a problem.
The morning was quite dull. I reverted back to being a man and helped Sara clear up the house after the guests. Then I read the paper and went for a walk. Life had returned to normal.
How wrong was I. Later in that week I was having a drink after a gym session with John, he rather awkwardly and almost in a whisper asked if, me and Sara would be up for a bit of hosting at a dinner party they were involved in. I remember looking at him with what he later described as an odd expression on my face, I could only think of all the many ways the word why could be incorporated into my thoughts. So I asked him why and for more information. Turns out him and Mia have organised a party for the end of some project at his work, they are doing it at their house, the food is organised, but they were going to do the hosting themselves, but after seeing Sara and myself doing such an excellent job wondered if we would care to do it for them, and get paid off course. I said yes without thinking much more about it, then he added that I might not have understood what he was asking for, they wanted us to be turnabout butler/waitress for the event, not as our regular selves, add a bit of novelty and variety to the event. Now that put a different light on the situation and made me put a condition on my answer 'I shall have to ask Sara and check our diary' how fast can I back pedal is what I was really thinking.
Later on when I saw Sara, Mia had rung her and asked her the same question, would we be up for doing a bit of cross dressing as a bit of fun for their guests. We then spent quite a while trying to work out what the other was thinking, and in my case, what I was thinking. Should we do the dressing up again, was it fun, was it too much effort, were just a few to get us started. We left it on a maybe, but we had both agreed that we had enjoyed hamming it up as the opposite sex. The point at which we said yes was when John rang me and told me the budget would cover our expenses for hiring something suitable and several hundred for doing it.
We had about 10 days to organise ourselves and to start with we went to a formal outfit hire shop, and once they had realised that it was Sara who needed to tails and me who needed the smart frock they soon got us fitted out. Sara was soon sorted as she just picked a style, got measured, got changed and was seen to be decent. I had far more options, I had taken a bra and was wearing my control pants so as the dress what ever the cut would fit as well as it ever would. We were shown several dresses, the requirement was to be black or dark, not too dressy I was not a guest so I should look like staff in some way. The chioce was not great as they really did dressy and after a while could feel myself wanting to see what a long gown might look like on me, but I was given plain black dresses to try on. The one we chose was a fairly understated dress, a shirt collar, wide belt, some net underskirting to make the skirt part flare out a little, but not in a big way, sheer sleeves with wing cuffs. I then needed to get some black shoes to go with the dress, stockings and underwear. Black underwear was easy to find, but we could not decide on stockings or tights and what colour, in the end we bought fine black denier seamed stockings which seemed to go with the stileto shoes we bought. Sara bought a pair of black brogues to complete her outfit which was much easier.
We had a try on session the day after with both of us going through our own transformations. I could not get over how different the black dress was to the green one, with the skirt flaring out a little, my hands felt the fabric all the time. Other things to get the hang of were the narrow heels which I swear were higher than the cream ones, and having to get seamed stockings straight is such a faf. It took a good hour to get both of us dressed, so we sat down to have a coffee while thinking 'what next'. I was not so confident in the new shoes, so we decided to stay in our roles, change our outerwear but I needed more time in the heels to get used to them and we had time to get reaquianted with our roles. Sara lent me her little black dress that barely covered the stockings and required constant monitoring, while Sara took jeans and a shirt to relax in. I did not get that much time for relaxing, Sara thought it would be good if I practiced carrying a tray of drinks, and when I had had enough of that suggested I set the table for ten, then clear it trying to look professional and not carrying one plate at a time. This was harder and took more skill to balance the plates on my arm, all the while feeling my ankles and calves fighting for control over the narrow heels that my shoes had.
That Sunday was not so bad, but I did wear the heels about the house so I could get my legs used to the more difficult footwear, besides that I was just a normal bloke. That was until Saturday. We ran a few errands that had to be done first thing, then I was sent off to get myself into the role, scented bath, hair removal, wearing my practice blouse and skirt along with everything else for the afternoon so I got to do the feminine gestures that go with the clothes. Sara told me I looked great and started to get a little bossy as she told me it was my job to polish her shoes and give her suit a brush over to removed the fluff. When I queried this instruction she informed me that a butler is more senior to any staff in a household. I gave up, bobbed a neat curtsey picking up the hem as I went down and asked if there would be anything else. Fortunately she took this in the manner it was meant, a tease, on reflection she could have taken it as a submissive act and followed it with more demanding behaviour.
We rolled up at John and Mia's house in good time, the cook was well into her work and we just had to get ourselves used to where things were and what they expected us to do. Mia in a rather too girly way told me I looked great, but I was nothing next to her in a blue patterned maxi dress, her hair all done and looking like she had just come from the hairdresser's. Sara was to welcome people at the door, I took their coats, then later I would circulate with drinks. Sara would be a master of cermeony calling people to sit, then we both served with the help of the cook who plated everything up. It was me who cleared away and Sara who asked various people to stand and make speeches. From the sounds of that last bit it sounded quite straight forward, the twist being that I was in a dress which in itself caused me to become quite a talking point as well as being chatted too when I was supposed to be working, I noticed Sara having similiar problems at times. Most people wanted to know why we were doing it, for fun was the best answer, some women asked about the dress, some men commented on the stockings and shoes, bemoaning the fact that their partners never wore anything so sexy. A couple did ask if we did this sort of stuff as a lifestyle chioce, my answer which I thought quick witted at the time was, not been doing it long enough to know but will let you know if I end up in a salon having my hair done.
We went home as we had arrived, in our outfits, Sara had my long coat on and I borrowed Sara's 3/4 length. In the quietness of the night I could hear my heels tip tapping so clearly on the pavement I found myself listening to the rhythym and enjoying the experience of the cool breeze on my legs and the affected way the heels made me walk. So when we got home after the short walk and I started to undress and clean myself up it was easy to pull the silk wrap around me, but no nightie. That was until Sara noticed I was getting into bed withouut it and asked me to put it on. Easy short hand for I want to make love, and we did.
It was as I lay next to Sara the following morning wrapped in my silk nightie that she quietly whispered in my ear 'that was fun last night' I replied with a dopey huh. 'and you do quite like this dressing up malarky' again huhhuh was my reply 'good, because I was asked if we would do the same thing in a months time'. That got me awake pretty sharp.
'You did what?'
'I told them we would be happy to host a party, just ten of them, so we do the catering as well'
'what ?' I was completely lost for words.
'well you look good, you enjoy yourself, we can make some extra cash, what are you getting so upset about. Is it that I took the man's role and spoke for the both of us'
'pardon?'
'You heard me, I was the man last night, they talked to me and not you, if that felt bad, get used to it, this is a man's world and you will need to learn that when you are in a dress my dear'
'Do I get any say in this?'
'Well only in that you get some say in what you wear, as long as it is pretty and feminine' she smiled at me then gave me a lovely kiss. I was stiil not sure how serious she was about her being the man.
After some time to let the shock subside I talked with Sara about the event more fully, we would get paid well and it would be hard work but not that challenging, we had done it twice and been successful at being a pair of cross dressing role reversal people, so why not do it again.
Well twelve months have passed and we have had our first repeat booking after doing quite a few parties, the theme this time was a sultan and one of his harem. It was pretty much the same as before but in different clothes, what has changed is that we now keep ourselves sort of ready for the next booking. I spend time every day rubbing lotions into my skin to keep it soft, I had my ears pierced six months ago so I could stop using the clip on earrings, my hands are well moisturised and the nails well manicured to a length that is just on the edge of what a man might have. I am clean shaved all over all the time and have a weekly appiontment to reduce facial hair, close shaves are such hard work on the skin. My hair is getting to a point where I might consider ditching the wig but I have not really got up the nerve to give up my man cut yet in favour of a more feminine style. Sara on the other hand has started to go to the gym to build up her muscles, in the summer she had a short hair style and has kept in short with her ears showing. She still likes to be feminine at times and she can look really good, but most of the time she looks about as feminine as I look masculine, we possibly meet somewhere in the middle, then when we have a booking go off into the extreme of the oopposite gender. Quite a lot of fun really.
Well that was a busy twelve months and can you believe two years since I first wore a dress. The party hosting was a big success and we have been getting 2 maybe three bookings a month, more around christmas when the parties really came into their own. We have also done a few stage appearances doing things like karaoke or presenting shows even a fashion show once. I have been asked if I would like to do a panto next winter, I said maybe to that. My regular job was getting too much, what with the time it took to do a turnabout event, and the money was not that good anyway, so I earn as much from just mucking about now. Sara still works and has got to be a manager now which means she is getting paid to be bossy instead of pretending to with me.
It might seem strange to the outside world but we still see ourselves as man and wife, I still identify as a man, Sara still sees herself as a woman, but to the outside world we are hard to read quite alot of the time. I was doing tele sales so my appearance should not have mattered but just before I left, it was obvious I had been doing things which affected how I looked, everyone knew about our turnabout events but the ear studs first, then my beard thinned until it disappeared, my nails gradually went from just neat to rather long for a bloke over time, but I think it was possibly my thin eyebrows or maybe my longer well groomed hair which made it clear I was looking more girl than boy.
It was after I left and had my final pay check that I felt I might as well take the plunge and have my hair styled properly. I booked at Sara's salon who knew all about us so were not thrown by me making an appointment. For effect though I did turn up with light make up, a cream silk blouse and black trousers on, I felt I could be taken for either sex with my hair in a pony tail. That was until I left later on with a shoulder tickling bob which had been streaked in silver, gold and blonde making a big statement about how people would take me in the future. The fringe needed gel to keep it from falling in my face, but besides that it was an easy style to maintain and could be hidden if a more outrageous wig was needed for a particular event, or wrapped up into a hat if I needed to be masculine looking.
We moved house a few months ago and we are not sure what the neighbours make of us, they see Sara going off to work in a dark suit and short hair, then they see me about the house in the day, with my bob cut hair, long nails and to be honest rather feminine chioce in clothes, I do wear jeans but I have grown to like women's blouses because the fabrics are so much nicer than any shirt I have ever worn, and if we are going out to an event we go dressed ready for the customer, even if we are to wear something out of the ordinary I shall wear a dress just so I am prepared in myself for being the woman in the team.
Sara was teasing me the other night I might as well box up all my old clothes as she has not seen me wear anything without a ladies size label in it for months. I did not throw much out as I still wanted to have something to be a slob in and who knows I might need to present as the gender I was born one day.
If you have any ideas for a party this couple might host then feel free to make up your own story, write it out, or send me your suggestions.
Happy dreaming.
Lauran
A short part of a person’s life, but was he totally surprised by the outcome or was he leaning that way and just needed a push? Were the girlfriend and his date in league together? But most importantly will the experience change him forever?
We had been together for a year and I thought we were doing fine, I had moved into her flat when my lease came up for renewal and after a few teething problems we got used to sharing her flat all the time. That was until two weeks ago we had had our Saturday night sex and I thought it was ok but she clearly did not, can you believe it she turned to me and said ‘Rob, there is no easy way to say this, you are pretty useless in bed, you never consider what I want, it is just play a little then you get stiff and thank you I’m done.’
‘But I thought was what you wanted?’
‘Like you ever asked.’ She replied tartly. ‘Anyway I have been thinking and I reckon it would help if you got to see things from the other side.’
I was confused now ‘How?’
‘Oh easy, Marcus has agreed to take you out and show you a good time.’
‘What!’ Still confused ‘Marcus is gay, nice bloke but,,,,,,,,,,oh I get it, you want me to be his date and let him flirt with me.’
‘Not quite, I want you to be his girlfriend and go on a date with him. He will treat you like a woman and hopefully you will do your best to respond like a woman.’
‘But, but, but, I am a straight bloke.’
‘Is that what you think, all that body lotion and special soaps, you even have manicures.’
‘Well that is because they are good for me. Anyway what makes you think I will agree?’
‘Because little Robby’ her voice went quite stern ‘if you don’t you will not be coming near me with that’ she squeezed the end of my limp but tender dick ‘and you will need to find yourself somewhere else to live.’
‘But that is a bit harsh, date Marcus or else, what kind of a deal is that?’
‘One you have to agree to or leave.’
‘But what if I just listen to what you want.’
‘No deal, you never listen anyway.’
Well that was two weeks ago, by the following Saturday I had not only agreed to her crazy idea, but had accepted what she termed training, which was supposed to help me pass more easily as a woman, Marcus was not wanting to be taking a horrible bloke in a frock out. It started with spending Sunday walking about in heels, but as the week progressed the heels got higher, I lost all my body hair, she plucked a few hairs from my eyebrows and on Thursday so I knew she was serious, with a mixture of superglue and tape, pushed my balls inside me and secured my dick so it faced backwards. It would swell a little but the worst was having to sit when I peed, just like a girl. When I complained she kissed me and said ‘perfect’ in a very satisfied tone.
Saturday itself was a day full of new experiences. My first was to feel what it was like to have a bust and be grateful for a bra, the glued on prosthetics pulled at my chest unless they were supported. Then there was the sensations of wearing a satin thong, a matching black corset and fine stockings. My trapped dick wanted to come and play in response to these delights but I just had to sit on it as it were. I had always loved my hair and taken care grooming it, it shone like a girls my mum had once told me which I was quite proud of and now it was quite long, I am sure she would have said it looked like a girls. Beth washed, conditioned then adding some new products before rolling it onto rollers and leaving me to sit under her hair drier hood until she was happy it was ready. As she unfurled the rollers I could see my normally straightish hair had some serious wave going on and I remember thinking, ‘that looks good’ but she then starts backcombing and pinning it up in a pile on the back of my head. So much volume and with just enough tendrils escaping round the edges.
Next she informed me that my ears were to nice to go unadorned, so with a block of ice and a needle I was given the addition of a couple big pearl studs. ‘Classic’ she told me. I think I agreed with her. It was about lunchtime by now and all the ‘training’ and now Beth’s pampering was making me feel quite different, even feminine. So it was no surprise to hear Beth tell me I was mistakable for a woman already, my hair was up, I was wearing some sexy underwear I once bought Beth and sitting rather erect due to the corset and involuntarily stroking my stocking covered legs which felt so nice.
‘This feels rather nice, why do you never dress like this?’
‘That is the point, if I go to all this trouble, yes it feels nice but you never appreciate it, you never compliment me, and when I do it makes no difference, you treat me the same as you do when I am in jeans, so why bother?’
I apologized.
Lunch over, and it was back to completing my transformation so I can stop with Beth. She glued some long nails to my fingers and painted them a deep shiny pink, matching my toes. I thought I must be nearly done as she set about my face with cosmetics, base coat, blusher, powder, eye brow pencil, eye liner, various silver shadows round my eyes finished off with a few layers of lengthening sticky mascara, and last the same deep pink colour lipstick as my nails was applied to my lips but with an extra coat of clear she said would make a huge difference, initially it just made them look wet and glossy but then my lips started to tingle and swell, my normal narrow lips pouted without me doing anything. I looked completely different but did wonder what sort of signals the way Beth was dressing me would be giving off. When she pulled the zip up the back of the fitted dress I got my answer.
‘Now then Robby, slip into the heels, a dab of perfume and these pearls and I think we shall have it.’
‘Have what?’
‘Restrained sexy.’
‘Pardon.’
‘I think I have made you look like the sort of woman men take a second look at and think they wish they were with someone like that, because you look good but also because you look like you are enjoying flaunting your sexuality without being a tart.’
‘What!’
‘Marcus like I said will treat you as a woman, you need to respond like a woman and a sexy woman is always a good place to start.’
‘You think I look sexy and so I should act that way?’
‘No should about it, you will act sexy, act like you wished a girl would behave for you. I expect you to flirt, encourage, kiss, cuddle, flutter your eyes, whatever it takes to make you look sexy and for him to feel he is the most special person in the world.’
‘But.’
‘I know you are unfamiliar with most of this but that is why you are doing this, and if you don’t and Marcus comes back saying you were a right moody miserable cow then don’t bother coming back and expecting a welcome.’ The reality of what I was supposed to be doing just hit home. ‘Got it?’
‘I think so.’ I replied in a rather weak submissive tone.
‘Ok you have until seven to get that sexy wiggle into your ass, and some grateful attitude into your demeanor. So I suggest you get in front of the long mirror and practice.’
I was just about to ask if I could have something to eat, when she appeared with a drink for me, I looked at the clear liquid.
‘Gin and tonic. Get you in the mood hopefully.’
I took a sip, it was a strong one but nice and I would need some dutch courage.
Seven came and I had been resting for a short while, though a corset hardly lets you lounge, I sat upright as I was encouraged to by Beth and the underwear. My feet ached a bit but I had got the wiggle as I walked by dropping my hip as the weight transferred. She gave me a final pep talk about making sure he felt special and to let him take the lead but saved the most shocking to last, a small clutch bag with a little cash, a few bits of make up for repairs, my phone, I was fine with these, but the tampax and a condom were there as well. Her explanation, all real women carry a towel, and all sensible women on a date carry a condom for just in case the guy is not well prepared.
The penny did not so much drop as crashed. ‘You want me to let Marcus screw me?’ my mouth somehow did not close as I further realized just what Beth was setting me up for.
‘But that is the whole point, I want you to be on the receiving end and learn what it is like to be a woman.’
‘Ok right got that, but sex?’
‘And sex, I don’t expect you to let him just screw you anywhere, he will have to take you somewhere nice, the back seat of a car is never good.’
‘But he is gay.’
‘And yes you only have one hole down there and not two like me, but he prefers the one hole arrangement and who knows you might be like plenty of men and women and actually like the feel of something deep inside them.’
Just then the door bell rang and a casually dressed man I knew as Marcus stood there, he kissed Beth on both cheeks who then stood back and introduced me. ‘Marcus, this is Roberta.’
‘Gosh Roberta you look fantastic.’
I tried to look coy and angled my head down and looked up at him with a smile on my lips. ‘Call me Robby please.’
‘Ok Robby, are you ready?’
I picked up the bag ‘As ready as I ever will be.’
Beth never gave me a kiss or even a farewell word as Marcus took my hand and lead me out to his car. I was sure every nieghbour would be watching and laughing at me as I made my public debut but it passed without a hitch. Once I had overcome the technical problems of getting into a car in a tight dress and heels I relaxed a little.
‘Right then Robby let me just get this straight, this is your first time out in public as a woman?’
I nodded.
‘And you want to experience as much as possible the female side of a date?’
I nodded thinking it was not quite how Beth put it but close.
‘And just to be sure, Beth is ok with her boyfriend going out with a gay bloke while dressed as a very attractive woman?’
‘It was her idea and it was she who dressed me like this so she must be ok with it. And less of the attractive please I am sure there are lots of better looking women about than me.’
‘Not that I look so much, but you do look very convincing and believable as a woman maybe just keep your voice softer and you could pass as the real thing.’
I was blushing under the makeup and changed the subject ‘Thank you, but are we stopping here all evening or are you going to take me somewhere?’
‘Oh sorry, yes, going back to my house, drop the car and get a taxi into town, a nice wine bar then maybe a club. How does that sound?’
‘Sounds fine to me.’
A short drive to his house where we meet the taxi he had ordered as we left Beth’s. The wine bar was softly light so I felt safe from noticing eyes. I did my best to make him feel special, I asked him about his life, linked his arm as we walked, though that was as much for support as I controlled my balance on the heels, then as we ate I let my manicured fingers touch his hand and my foot stroke his leg. Beth had done these sorts of things to me and I did them as an act to start with but when I got a reaction from him I did it for another smile or a returned touch. The meal over I was rather enjoying myself in trying to make Marcus feel special he was making me feel special also, I felt comfortable with him, looked after, taken care of, his. And besides how he was making me feel, the clothes were having an effect as well. The soft satin dress fabric riding over my bare buttocks as I walked felt sensuous, the bouncing breasts in my bra reminded me if needed that I had the shape of a woman, and my heels stopped my clomping about like a man and forced me to walk in a different manner which I hoped was with a wiggle as Beth required.
The club Marcus took me to was one with a diverse clientele, every sexual orientation was there I guess so I did not feel threatened or to weird. As I drank my first drink there I saw men kissing openly and two women elsewhere not hiding their lust for one another if where their hands were was anything to go by. I remembered what Beth had told me and put my hand on Marcus’s thigh as he put an arm round my shoulder. Soon we had danced, cuddled and even kissed properly. In the toilet, ladies off course I was about to wash my hands when I noticed the women checking themselves in the mirrors and repairing their makeup, so I followed suit. As I touched up my lipstick a big woman came beside me, looked me up and down, and then in an unusually deep voice for a woman asked ‘You with Marcus?’
‘Yes.’ I replied.
‘He is gay you know.’
In that moment I realized I was being taken for a woman, this person thought I was a woman. Now do I answer ‘Yes I know’ and revel myself, or say ‘Is he?’ so concealing my sex and affirming their belief. I said ‘Is he?’ I rather liked the idea of being taken for a real girl. I could tell I had given a confusing answer so when I found Marcus I made sure I kissed him like I always hoped Beth would kiss me, and in view of my interrogator.
Marcus took my kiss as a turning point he later told me, it had felt as if I was playing a role until then but with that kiss I signaled to him that I had stopped acting and was for real. Before he had chatted with a few people he knew, after that I got his undivided attention and I enjoyed being treated that way, I felt special. Soon it was gone midnight and we were having a slow dance and my mind was flitting between going home and feeling Marcus’s erection pressed against my stomach with the added thought of ‘does he want to stick it in my arse?’ and even in my tipsy state it scared me.
We left the club and made our way to a taxi office nearby, and as our taxi pulled up Marcus asked ‘Mine or yours?’ and though it scared me to think of what might happen if I went back with Marcus, to go back this early to Beth would almost certainly mean I would be house hunting in the morning.
‘Yours’ I replied.
‘Sure?’
‘I think so.’
We had a night cap and some arousing kissing once we were behind closed doors. He kissed cuddled and touched me in such a way that I lost my inhibitions as I thought about how I would just kiss then screw Beth. My next shock was handling his cock and recognizing that compared to mine it was huge or maybe mine was just tiny, after all it was the first erect cock besides mine I had ever seen in the flesh.
He ever so sexily removed my clothes before laying me down on his bed, I was then treated to Marcus doing a strip for me, by the end all I wanted was to see his cock fully exposed. OMG it was as big as I thought, how would that fit inside me? And did I want to know what it felt like inside me? I had come this far, off course I did. I held a hand to him and invited him to join me. Soon he had massaged jelly into my arse pushing his finger inside so I got an idea of what was coming, then with my condom safely slipped over his pole he gently but firmly started to enter me, there was no rush he was savouring the moment. He treated me with respect, if I flinched in pain he stopped and caressed me before pressing further in. I could not believe it when after several slow ins and outs I felt his body press against my buttocks, all that cock was inside me, amazing. Next he slowly started to screw me, pumping as he did something inside me that seemed to inflate, a rising sense of excitement. His pumping increased in rhythm as my excitement grew until I reached out and grabbed his arse pulling him into me, my back arched as I reached bursting point, somewhere a voice was saying ‘go on’ in between moans. And then I came, not a quick sudden rush like I did with Beth but a deep panting as waves of delight flowed through me.
I relaxed, exhausted by my experience. I lay in Marcus’s arms holding me tight feeling wonderful in the post coital euphoria. I had learnt so much in just one evening about how wonderful sex could be, my question was, did I want to go back to Beth and show her what I had learnt or be Marcus’s girlfriend again and enjoy being screwed like a woman. I very much preferred the latter if I was totally honest.
-----
I often wonder who watches Springer and other such programmes, and more puzzling, who for a free night away would consider having the world sticking it's nose into their lives. Clearly a lot do. It also gave me the idea for this unrealistic fantasy :)
I came home to find my partner watching Jerry Springer, not her usual viewing I know but she was transfixed by the characters who would put themselves forward as people prepared to have the nation see them, possibly laugh at them, most certainly question their judgement. At a glance I noticed two women being interviewed, but then as I listened it was clear one of them was a man from what was being said, but not from how they looked. I went to make myself a coffee and came back in to find her still there, glued to the screen.
-----
'This is incredible, one of them is a man, can you guess which?' she asked me.
'Well no they both look great, it must be a wind up, it will be two women wanting to make a few quid off the programme by pretending one is a man.'
'No Springer says they have been checked out and the one on the left is really called Chris Norris.'
'Fascinating' I said sarcastically.
The programme ended, then I noticed she was looking at me oddly.
'Come on then, what is it'
'I reckon you would make a good looking woman.'
'No I wouldn't, I have man bits and no woman bits, and I am not having some doctor chop me about to alter that'
'No without anything drastic, you could pass as a woman.'
'As easily as you could as a man you mean.'
'You think I can't be masculine then'
'I was not saying that' this was getting out of hand and I just wished I could put the shovel down and stop digging the hole any deeper. Carrie is a great girl, a bit taller than me, but then I am bit short at 5'5", and she keeps fit, so has a pretty well developed muscled body. But she is not butch, her face is pretty and has lovely neat hair.-----
'Tell you what, tomorrow night we are going out as two guys.'
'What?'.....'Why?'
'To prove something to you and me'
'What?'
'I don't know, but I just fancy dressing up as a man and see how it feels'
'Ok, tomorrow we can go down the pub and we see if you get served beer in a pint glass or a ladies glass'
Deep inside I dreaded her being successful because I just knew she would then want me to dress as a woman. It was going to be a long 24 hours.
-----
I got home from work the next day, was about to flop in the armchair when a dark haired man walked in the room, it took nano seconds for me to recognise her but it was enough for her to sense success. Gone was my blonde girlfriend, before me was a man complete in pale chinos, brogues, blue and white shirt giving no hint of anything but a flat chest, her face even had a darkness on the chin, and like I said dark hair tucked behind her ears, ear rings completely gone, she even smelt of aftershave.
'Well say something' a rather husky voice enquired. 'Good eh?'
'I suppose so, not sure what to say, I can't call you Carrie now it seems wrong'
'I thought Carl, what do you think?'
'I think I am sunk, can I get a drink and change before we go out?'
'Off course......mate' well she could hardly call me dear or sweetheart could she.
-----
I drove us out to a country pub and with her by my side ordered two lagers, 'pints or halves?' the woman behind the bar asked 'halves' Carl replied. We got two beers in identical straight glasses. We took a table and she drank to her success.
'Let's try another pub' she suggested.
'I could really do with something to eat'
'Fine, let's go to the indian'
-----
At the restaurant she was treated just like me, no pulling the chair out for her, no stemmed glass, no fawning over her. We were just two blokes out for a curry. By the time we were home she was so excited with her success that it took a good half hour before she was calm enough to be ready for bed, which in itself was odd. I had just spent the evening with my partner looking very unsexy and now she was getting into bed with me, it just did not work for me, and after a cursory kiss rolled over and went to sleep.
-----
That was Thursday evening, so with dread I imagined it my was turn on Friday night. But I came home to find her still dark haired but in jeans and a loose jumper, looking quite normal but still there was the masculine edge.
'My turn I guess then'
'Well yes it is your turn, but not tonight, I have been out and got a few things but it took me the best part of the day to transform myself into Carl, so I thought maybe Saturday would be a better day, plenty of time you see'
'Oh'
'Made your favourite for tea'
'Thanks' I said without enthusiasm. I now had all night to worry about what she was going to do to me, and would I look as convincing as she had, I dreaded to think that I might.
-----
Come Saturday morning I was awake early and slipped downstairs to make breakfast. Before I had finished she appeared in my towelling robe carrying her satin one.
'Get you in the mood, slip this on' I did and felt a shiver run over my skin, it was so soft and sensual. She must have noticed. 'Nice isn't it' I passed her some toast without comment.
-----
From then on my Saturday was one shock or new experience after another. The first shock was to see you body hair wash away down the drain, the next new experience was to massage miosturiser into my skin then put the satin robe back on. Even better than before. I then had to master fastening a bra, getting all my male bits into panties and pulling on tights. Then I dressed in a dark blue pleated skirt of hers and grey woollen twin set which hugged my newly redefined chest shape. Last she gave me some low heels shoes to put on my feet, before making me sit down so she could make up my face and fix a wig to my head. At last we were done, she stood back and then came back to hug me.
'You look fantastic'
I got up and looked in the door mirror, fantastic was not the first word to spring to my mind, more OMG she could be right, deal with it, were the thoughts that crashed through my mind.
-----
I had no idea what to do next, so when Carrie said we should get the house work done, I just felt I might as well, so went to the kitchen to start clearing up and cleaning.
'Do you want to come shopping?' she asked.
I tried to seem calm, 'No you go on your own this time, I will get on with things here' and gave her a smile.
'Right then, see you later darling' she picked up my jacket and wallet, then gave me a kiss and squeezed my bum.
I said 'What?' rather to high as I moved my hand to my back so I could move the offending hand.
'Cute, do you not like being fanciable?'
'Go and do the shopping' I said trying to end this moment.
-----
Just before lunch Carrie returned with the carrier bags loaded with her purchases. I was helping put the groceries away when I came across an odd box. 'Oh I was wondering where those had gone' she took it from my hands 'sit down and we shall make your fingers look fantastic as well' I looked at her, worried what she meant, I had worked out the box contained nail tips. It took a while to sort out the correct sizes and then glue and paint them a deep pink colour. I did not admit the longer nails did make my fingers look better, but my liking of them was short lived as I started helping with lunch once the varnish had dried. I was unable to use my fingers in any ways that I was familiar with, so had to work out ways of doing things now my finger tips were restricted by the long nails. All Carrie could do was smile as I struggled. This was all getting too much, as was coping with the long hair that straying into my face, not to mention the skirt wafting around my legs making me reconsider how I moved particularly when I went to pick things up, the increased height had caused me to bump my head unexpectedly on a door frame I normally walk through. I was definitely beginning to think she had got the easier of transformation, well being a bloke is just easy, even I can do it without thinking.
-----
We were done with the cleaning by mid afternoon and relaxing with a tea, when Carrie asked were I fancied going that evening.
'Good film on the box tonight and a take away would be fine by me'
She smiled back at me 'You know that is not what I mean. I did it, so now it's your turn, besides I have a few more treats for you'
I dared to ask 'treats? like what?'
'You will never know unless you keep your side of the bargian'
'do I have choice?'
'not really'
'thought not' I was resigned to my fate and finding out what her treat might be.
-----
I spent the afternoon watching moto GP, then she came in with a bottle of wine and poured two glasses. 'do you want to go out with Carl or Carrie tonight?'
I had not considered this option 'I don't know, rather too worried about going out as a woman to have thought about you. Which do you fancy?'
'I thought I could be your boyfriend for a change, any objections?'
'Guess not' and that was it the evening was set. We drank our glasses, had some snacks and drank some more while we sat together watching the football results.
-----
'Right then Stephanie time you was making yourself beautiful'
'Beautiful will be a challenge, can we go for not embarrassing' smiled at her then gave her a kiss.
With that she took me by the hand to our bedroom, there I stripped while she got out want she wanted me to wear that evening. I was down to bra and panties and feeling oddly naked, happy to wrap myself in the satin robe once more.
'You like that don't you?'
'There is a bit of a chill' I hoped might be enough of an excuse.
She then stroked my leg through the satin and a very clear bump appeared at the top of my leg. 'See you do like it'
'Stop it please, that is not helping'
'Now we have a problem, I don't want my girlfriend having a bulge down there' she had not removed her hand and was moving it further up my thigh.
'Please stop'
'I could make it limp, or do you want to handle it?'
Just at the wrong moment I let out a low moan, this was hard to not respond. Next thing I know her hand is wrapped around my penis and the satin is having it's expected response. I was going to brush her hand away, but she bobbed down and kissed the tip, and after a little more attention I had exploded.
'sorted' she just stood up and smiled at me 'better wash yourself now'
How awkward, she had me completely in her control then and I could do nothing to stop her, but the satin and blow had been so nice I was not going to kick up a fuss.
-----
Cleaned up I returned to the bedroom, to see more wine in the glass. 'Right time to get ready, I have some clothes for you so you can dress as the woman you would like to take out, and I have looked out some clothes so I can look like the sort of man I would like to be seen with. Fair?'
'I suppose so' thinking I could imagine some of the outfits I had tried to get Carrie to wear in the past. I had my next novel experience, wearing a suspender and stockings. The fresh panties were holding any resurgent bulge in place. Next she brushed mousse through the hair and blow dried it into a big curly mass, without the earlier clips this was going to be even more in my face. Next she applied cosmetics to my face, this time detailing what she was doing and getting me to use the brushes to apply them. I had thought the earlier make up disguised my features well, but now, I had defined cheekbones, sultry eyes and lips that looked so kissable I was shocked.
'You like?'
'On you, yes'
'No, on you, I saw you smile. One last thing, this will stop the lipstick coming off' and she coated my lips with a stinging liquid, 'now we can kiss and you stay great'
'Am I supposed to say thank you'
'If you like. Now if you slip into the dress and shoes I will go and get ready. Sorry about the dress, I know you like cleavage and bare shoulders but I could not think how to do that, so I hope you like it'. Hung on the back of the door was a dark grey and silver cross over dress, I took it and slipped the silk over my shoulders and pulled it around me. There were only two fastening, a hidden one on my right hip, and a tie on my left hip which fastened into a large bow with tails that came to my knees, way below the hem of the dress, the top was a plain V with no sleeves. By the door were a pair of high heels with little ankle straps, I sat on the bed to put them on and noticed the dress parting across my thighs revealing a glimpse of the stocking tops, all I could think of was 'this is going to be such hard work'.
'Do you like it?' came a question from the bathroom.
''Just trying to get the shoes on' I would have loved it on her, but silk carressing my skin was lovely though I was not going to give her the satisfaction of hearing me say I liked it.
'Pick some jewellery out of my box, try the green necklace and silver bangles, some rings might fit as well'
I had the tiny buckles fastened and could feel the height before I stood up.
'wow wah' was all I managed as I staggered across the room.
'Walk on your toes' was her advice. I made it to the dressing table and jewellery box, I found the bangles, a small watch and a couple of dress rings that felt so bulky but I always liked on Carrie.
-----
Carrie or should I say Carl walked in the room at this point. A very smart gent stood before me, a grey suit, darker grey shirt and tie, cuff links, brogues and that smell of aftershave once more.
'So how do I look, will I do?' she asked.
'Bugger me, you look so convincing, better than Thursday. Very smart by the way, does it feel ok?'
'Yup feels fine' she said with a deeper vioce.
'how did you do that?
'Let me show you, open your mouth' and she surprised me as she sprayed something horrid tasting into my mouth.
'What was tha.....' my vioce was not my own, it was up an octave at least.
'Great isn't it, one for higher, one for lower' as she showed me the aerosols.
'Here let me help you with the necklace' and as she fastened the clasp I pulled the hair out of her way. The scattering of small green stones around my neck was nearly the final touch, I was given a bottle of scent and told to give my neck and wrist a squirt.
'Right Stephanie you were moving alright before, but these shoes will need some practise' She took my hands by the fingers and helped me to my feet then walked backwards as I walked towards her.
'Imagine a line on the floor, and drop your hip as you move your wieght from one leg to the other'...........'keep your head up don't look at your feet'...........'right and back to me'
She left me walking about as I grew accustomed to my new footwear.
'Ok taxi in twenty minutes, how you feeling?'
'Nervous'
'This will help'
She meet me at the bottom of the stairs with two shot glasses.
'To Stephanie'
'To Carl' I replied then tipped the vodka into my mouth. 'You sure about this?'
'Definitely, you look fantastic, sooo hot' which seemed to encourage her to put a hand on my hip and finger the suspender clip. 'and this is so much fun, can't remember getting such a buzz for ages' I was clearly not as fully into this buzz as she was. 'Oh come here' she leaned into me and kissed my lips with a forcefullness I was not used too, then I felt her press against me, I jerked and she smiled 'good isn't it' I had felt a bulge in her trousers exactly where I would have had a bulge if I was in the suit.
'Just not ready for it'
'Well you added some bumps to your figure, so I am only keeping up'
-----
I went to get a drink of jiuce and settle my thoughts, she was taking this more seriously than I ever expected, she looked very smart, but the bulge and the dominant kissing were a bit of a shock to me.
-----
'Come on sweetheart the taxi is here' I walked to the front door, this was going to be a big challenge, everyone down the street will be watching I was sure, but my concern was diverted as Carrie wrapped a dark pashmina round my shoulders and gave me a clutch bag as she pushed me out the door. All of a sudden I was on the front step and could hear the door closing behind me with a deafening bang. The taxi ten yards away seemed like miles, and then he is bound to make some comment and call me a pervert. Carrie opened the door for me, I concentrated on not showing my stocking top off.
'You look great love, my missus keeps asking me to take her out. If she looked half as good as you I would agree.' I was blushing as Carrie climbed in the other door, the taxi driver set off 'nice place you going to?'
'We hope so' Carl said
'Must be a special night, anniversary or something?'
'Birthdays, Stephanie's today and mine last Thursday'
I looked at my partner with a puzzled look, quietly the deep vioce said 'Stephanie was born today, yes?' I smiled back understanding what was said. Then with fingers entwined we kissed, this time I was better prepared for my boyfriend taking charge of the situation and let the kiss develop.
-----
The resturant was a really nice place, low lights, lots of space around the tables, lovely food and to say we fitted in would be an odd thing to say, the other diners were dressed up, so we fitted in on that level, but on any other level we were completely different. It was nice to have the chair pushed behind me as I sat, being asked first what I wanted, being served first, having my man taking charge of the proceedings, I just sat back tried to stay calm and take everything in. Soon enough all the courses had been served and we were discussing what to do next, we knew of an expensive bar that we had never considered before but that night we were not caring about cost and went to a high level bar where views of the city were spread before us. The drinks were expensive so we made them last as we chatted and watched the lights twinkle below us.
It was not late but I was getting tired, it had been an exhausting day what with one thing and another, it just had not been quite the usual you might say. I felt Carrie had had enough as well. So she got us a mini cab home and paid the fare, I had not spent a penny all evening, Carrie was doing the man part completely, and I had to admit it was rather nice not to think about such things, just trip alongside my partner and let them do the leading.
-----
Over a night cap we had a final chat about how we felt as the opposite gender. Carrie loved the simplicity of the clothes, and the way people talked to her, she said she felt some people gave more respect to her as a man, she also liked being in charge, something I had already picked up on. For me I had enjoyed the freedom of not trying to be the man, it was nice to just let her organise me for a change, I had also found the clothing a trial at times, but I did notice people looking at me and I was sure I looked good, so they were not looking at a freak, they were checking out an attractive woman, and I had never felt attractive before, which made me feel vulnerable as I wondered what might be going through these mens minds.
-----
Carrie suddenly got up 'Right as Carl your part time husband, I want us to do one last thing. If you have a look under your pillow, you will find something that you have always liked Carrie to wear, now it is Stephanie's turn.' I got a sly smile 'Go on, of you go, I shall lock up and be up in a minute'
-----
Under the pillow was a silk nightie, I had a good idea where this was going and continued to play my role as Stephanie. The dress came off easily, I was trying to undo the bra when Carl came up behind me. 'No leave it on' the silk being slipped over my head. Then the kissing started in ernest, soon I had an unladylike erection pointing forward. Carl to charge and lay me on the bed while she climbed on top and after we had removed enough clothing, let her ride me. It was one of our best ever love making times together, and as we lay in the afterglow agreed it had been good. So good in fact that we planned on having another reversal day the following Saturday.
It was a simple enough mistake, I thought Adam was gay, or at least I hoped he was. He was a friend of my sister, it was a large group connected by a football team they all followed. So home games especially she was out and watching the match, coming home late evening after going on with some of this group for a few drinks to celebrate or commiserate.
Now as I said I am gay, I share a house with my sister who behaves quite laddish, and with me being anything but laddish we sort of compliment each other. There were times when work allowed that I would tag along with her and go to a match, which is where I saw Adam the first time. I didn't speak to him I don't think, but I got a good look at him and admired his good looks and ease with which he handled himself.
After a couple more matches I had introduced myself and tried to be friendly, I was also hoping that he may just be gay because he was even nicer once I got to know him. A few more matches and I think I have a problem, I can't stop thinking about him. And then I bump into him on a weekday evening, we go for drink and get a kebab on the way home. He is just gorgeous, he never seems to have a girlfriend, so my hopes of him being gay ramp up. I haven't had a crush since I was a teenager, but I was having a crush.
When I got home my sister asks where I have been, so I told her. It was then my secret was aired, 'you fancy him don't you?' I went all pathetic and camp, but she isn't heartless, a hug and words of sympathy about understanding how all the nice guys are unavailable. I went of to bed realising that I was just normal in fancying the wrong person and maybe I should just abandon the hope.
Well my sister isn't the most discrete person, I didn't need to tell people I was gay, she did it for me. And you guessed it, she told someone, in confidence she assured me, but soon that one was two and then three, until it seemed everyone must know. Including Adam.
That he knew became knowledge to me when I happened to bump into him again midweek. I felt so nervous worried that he must know by now, and he did. 'I hear that you fancy me?' slipped into the conversation with such ease I was catch off guard, but it was what followed that threw me 'I like my partners to look pretty and wear a dress' I was staring at him trying to work out what he was saying, I was expecting him to go off on a homophobic rant or at least say quite bluntly I had no chance, but he didn't, he paused took a long swallow of beer while I nervously fiddled with a beer mat ready for the crushing blow. 'Can you do that?' Like an idiot I asked 'Do what?' He smiled and laughed a little 'wear a dress and look pretty?' I stumbled over words trying to work out the best ones to answer with, but my mind was working out if I could comply with his wishes just so I could go out with him. I tried a laugh 'very funny, but am just a regular guy not a cross dresser. If you aren't gay just say so, I have been there before' He was keeping eye contact as he replied. 'No you missed the point, I would go out with you, but only if you look like a woman' On the one hand he had said he would go out with me, and then took it away with his conditions that I felt unrealistic.
As you can imagine that more or less ended the evening. I got home in a miserable mood, I had never been rejected in such a way before. Amy might be many things but one thing she is good at as spotting my moods. She had me sit beside her while she hugged me and listened to yet another of my rejection tales. When I had finished and a silence was lingering she quite quietly said 'so what's wrong with wearing a dress, even I have a few'. I turned so I could face her 'but I am a lad!' 'So what' she replied and went on to point out how she wore men's clothes, why not the other way round, and in this age of trans everything what was stopping me from expressing me feminine side? In the end she summed it up 'if you want to go out with Adam then wear a dress. If you don't want to wear a dress then forget Adam' Why does it have to be so hard?
I tried to bring the subject up again two evenings later, wondering if he actually meant it, and could I possibly go out as a girl. She bluntly told me the only way to find out was to say yo would do it, and yes I would look fine as a girl, then went on to list all my 'good' points. Plenty of hair, not much beard, long slim legs, ability to walk camp, small hands. I told her to stop she wasn't helping. It was an away match that week, so she suggested I see how good I looked and then see if I could pass in public. My thing for Adam was overriding all common sense and I agreed, Amy asked my shoe size and said she would get everything I would need.
Saturday, I finished work at midday and went home wondering what Amy might have in store for me. She was waiting for me outside the store, making sure I went home. Then talked non stop all the way home, maybe she was as nervous as me, but possibly more excited than me. Once inside the the house I lost all my clothes and nearly my dignity as she pointed out I am not very hairy for a man. A good point she said 'be easy to get you hair free' as she pushed me into the shower with a lady razor. All showered and smelling of shampoo she passed me unfamiliar clothes. A tight pair of panties, all elastic so it flattened my little man. Next a bra with some very realistic forms inside them, bit of adjusting to make sure they were in the right position. 'Now to make you pretty' she sat me down and proceeded to put stuff on my face explaining what she was doing. My lips tasted different and my lashes stuck together with the mascara, but until I looked in a mirror I knew of nothing else. So I am looking in her mirror as she is positioning a wig on my head, and all I can do is stare at the reflection, I unbelievably look the part. 'Ok stop day dreaming, you look gorgeous. Now let me finish you off'. 'Stockings?' I asked 'Every bloke has a fantasy about his girl wearing stockings, so why not you? They feel good?' I said nothing because I didn't want her to know how much I was liking this experience. 'Right because this is just an experiment, nothing to fancy, a simple blouse and an easy skirt' The blouse was so soft it was luxurious, and the skirt was just long enough to cover the stockings. A pair of plain shoes, some modest jewelry and a squirt of scent and she declared me finished. I stared once more in the mirror at Amy's incredible transformation. 'Now have you thought of a name, can hardly call you Richard' 'what? why do I need a name?' 'Because my dear sister, when Adam asks you what you want to drink, he can hardly say, which cocktail do you fancy Richard. It would be a bit of a give away'
Amy left me to get used to the new version of me, the mirror and the heels were both proving a bit distracting.
In the end I just wondered round the house trying to be busy tidying up.
My next surprise was for Amy to come downstairs looking like a girl for a change, still in jeans, but in heels, makeup and styled hair. She looked really pretty like I had never seen before. 'Sisters are know for their rivalry' she informed me when I kept on staring at her. 'Can't have you looking better than me'.
'Right. If this is going to work you will have to get used to going out, it's what couples do, and you still fancy being a couple with Adam?' This was now real and I was nervous, did I want Adam to see me like this, never mind all those people I didn't know but may well spot me as a bloke in a dress, bad enough being gay in some places, being a tranny could be even worse. 'Well you just have to make people think they are seeing a woman, not a man then' was her simple solution.
'Right then, next step in this plan is to see if you can walk out the front door. So how about I get you a coat and handbag and we see how much you want to be with Adam?' This had been fun, the idea of being with Adam as a girl, the dressing up and disguising the man I really am was amusing and amazing to see, but this was going to be a challenge, walk out the door, along our street of terraced houses wondering how many might recognise me, frightened that strangers might see through the disguise. 'Right you have to do this, I have spent all day prepping for you, so think up a cover story just in case you are spotted, though I am quite proud of how pretty you are.' We agreed that I was a cousin if I was not rumbled, if I was outed then we are going to a fancy dress party.
The door opened and I stepped out, the cooler air hitting my near naked legs, then the click of Amy closing the door behind us blocked my return. 'Remember. Walk upright. Confidently. Don't make eye contact. Just act normal'
'But this isn't normal.'
'Maybe not for you, but for everyone else we appear like a normal women on our way out' So I followed her advice, looking down only when I had kerbs or steps to negotiate. Thankfully the walk didn't last long, but the bus ride seemed to last forever, even though it was only a few stops. Thankfully we were in the anonymous city centre. A bar that was serving food was our first stop, though how I ate when I was so nervous surprised me. Then a walk round, to get me used to being seen, she said, to make my feet hurt I said.
As the minutes ticked by I began to realise that Amy was right, nobody was taking an interest in me, yes people looked at me occasionally but no more than usual. Outside on the street I felt ok but when we went in a shop and had to stand in a queue I felt one or two were staring, Amy just pointed out I was the only one there in heels and a skirt, and people look at dressed up women.
With our mints bought she fancied another drink. I thought we were just looking for a pub that looked ok and walked past a few until Amy pointed at one 'Let's try that on, I've heard it's good'. I didn't have a choice really as she walked straight to it leaving me struggling to keep up with her seasoned walking on heels style.
I caught her up at the bar as she ordered two glasses of wine. 'I'll pay for those' a familiar voice said, I turned round to see Adam stood behind us with a note in his hand. Amy casually said 'thanks', I just stood there dumbstruck as I realised Amy had set me up. 'Thanks Adam, not sure you know my cousin Bella'. He gave Amy a hug then hugged me long enough to whisper in my ear 'You look fucking amazing'. He then lead us over to a table and deliberately sat next to me so we were squeezed into each other on a bench seat, Amy sat across from us smirking as she looked at me clearly not sure what to do but also clearly got myself on a date with Adam.
The conversation quickly became stilted because it was obvious why I was there, but it was still a surprise when Amy picked her glass up, tipped the contents down her neck and stood up. 'Well I'll leave you two to it, I don't think you need my help any more' and before I could get myself out from behind the table, she was gone. I was standing there wearing women's clothes with Adam in a strange pub, I felt panic rising as Amy disappeared. I felt Adam touch my hand 'At least finish your drink' I sat back down, only this time Adam's arm was round me. 'So Bella, you wanted to go out with me, and you have gone to all this trouble to make this date happen, so how about we go to a club and see how the night develops?' How could I refuse, I had wanted this date and allowed myself to get dressed up as he wished, he hadn't rejected me because I looked like a bloke this time, he was actually holding me in a way I wished more of my ex's would have done. 'So you are happy to be seen with me looking like this?' He gave me a squeeze 'more than happy, when I said I would go out with anything in a skirt I was maybe not being to honest, what I actually like are feminine boys dressed in skirts. Let's just say it is my kink, I like men but don't want to be an equal, I also like how some boys can look so pretty and behave like a coy girl'
I was sitting there fiddling with the hem of the skirt, pulling it down and feeling self conscious about showing so much leg. The silence was dragging and I felt the need to fill it. 'So you are sort of gay, why have I never seen you in any of the gay pubs?' 'Oh that's easy, I don't like all that macho stuff, and like I say, I don't want guys chatting me up, I want to take the lead. So drink up, I think I should take you to a club I like that plays great music and the bonus is girl's get in free' I was liking him even more, some gay men just want sex, Adam wanted to spend the evening together, I tried one more question 'so I guess you like being the top' 'obviously, but only with a willing partner who asks me' I turned to look in his eyes 'are you this nice to every girl you meet' 'I try to be, but then there aren't many girls like you so I don't get much chance to find out'. And then he kissed me, a gentle meeting of lips before he got up, took my hand and led me out of the pub.
'Come on, this might be your first time being a girlfriend, who knows it might be your last, but you look great and I fancy spending time getting to know you' I didn't know what to say, I didn't fancy just walking away, besides him being a perfect gentleman it was no getting late and the thought of walking about looking like this on my own was not a great option. I took hold of his hand 'So where is this great club that play fantastic music?'
By two in the morning I had learnt that dancing in heels is something I had not mastered, I had learnt an awful lot about Adam and why he disguises his homosexuality behind trans people. I had also learnt that he was a great lover. I had come to the conclusion that if he asked me out again it would be worth getting dressed up for him. I had also realised that I need to plan better, because come the morning I will have to get home and will only have the clothes I was wearing when I followed Adam to his house. Just how was I going to get home? Much to my surprise I had few qualms about putting the skirt back on, but before a next time I had better learn how to do makeup, just so I can feel more complete as a woman and girlfriend.
Sometimes it is easy to see how the dots join up in your life when you look back, but if someone at the beginning of a journey said this is where you will end up you would not believe them.
For me it was the early death of my sister, a sudden and tragic accident that left us all devastated. It took weeks before I could look inside her room, it took weeks more before I stepped inside, it still smelt of her, mum had been in a cleaned but moved nothing. It was almost a shrine. But I wanted something to remember her by, so the first thing I did was to just sit on her bed and breathe in the scents and remember her. But it was when I opened her wardrobe and the smell was strongest, I could pull a blouse to my nose and inhale. The next day I picked up a nightie to sleep with, just put in my bed so I could have the memory. I have no idea why I felt the need to wear it to bed, but I did. It was short silk and pink, so very girlie and possibly a gift from a boyfriend, it just had that look about it. It also felt good on my skin, I immediately saw the attraction of the nightie as a nice thing to sleep in.
A week later I was sitting on her bed thinking about her again, laid out on a small vanity was her makeup, I picked up a lipstick, it was her favourite colour, without thinking I smeared some on my lips and looked in the mirror. What a mess! I cleaned it off and carefully redid my lips taking care to get the shape right. The colour was just so her, I wasn't looking at the rest of me, just my lips and smiled which made them look even better. After a while I came out of my reverie, cleaned my lips and went on to what ever I was supposed to be doing. But the next day I did the same thing, put the lipstick on then smiled at myself in the mirror.
It took about a week before I was trying a sample of everything that was there, foundation one day, eye shadow another and so on. Mum would look at pictures, I looked at her belongings, both dealing with our loss in different ways.
It was a Sunday afternoon, I was in the house on my own, mum had gone out to see a friend, I had been out for a run and instead of going to my room after my shower, found myself slipping her dressing gown over my shoulders and sitting at her vanity. Maybe being alone, maybe having the robe on, I don't know why but I went further than I ever had before, foundation, eye shadow, mascara, lipstick. I didn't look anything like half decent but it was my connection with her.
I have no idea how long it had taken or how long I had been reminiscing, but I was not really listening for mum coming home. So it was a shock when I realised she was watching me from the door. My immediate reaction was to apologise, not sure what for, but wearing makeup is not conventional for lads. I rushed off to the bathroom and cleaned my face wondering what would happen next. Would she be mad because I somehow desecrated her memory, mad because I was wearing makeup. Eventually I could see no traces left and could stay in the bathroom no longer, so I stepped out and into my room.
'Adam. Come in here please'
Mum was sat in her room going through the makeup.
'sit down please'
A big swallow, ready for the telling off.
'Let me show you how to do it properly shall I?'
I was lost for words, instead of a rant she was applying makeup to my face and explaining what and why she was doing it.
'I'm really sorry, I just come in here to remember and think'
'I know you do, and this is a sort of connection I guess'
I nodded feeling she was ok with this weird situation. She had me blot my lips and then reapply the pink lipstick.
'Not your colour really but I understand why you used it, something a bit darker would be good on you'
This was not the conversation I was expecting.
'Now have you ever tried on a dress?'
Dare I tell her about the nightie?
'I know about the nightie, you forget I go hunting dirty clothes every now and then'
'Sorry' I repeated.
'Don't be. Now its a lovely warm day, how about a loose summer dress?'
Ten minutes later she has got me dressed in a long soft cotton dress, with bra and knickers underneath.
'There how does that feel?'
Could I tell her it feels nice? but I don't get chance, she gives me a hug and I can feel my tears forming and then her tears on my neck. She pulls us back from the tears.
'Let's get a tissue and dry our tears and repair the damage, then you could come and help me make something to eat'
As Adam I never got a look in at the cooking, it always seemed to be a women only area.
Half an hour later, I am sat across the table from her still wearing the dress, having helped make the chicken pasta, and slowly sipping some cold fizzy white wine, I had been told that a beer was wrong when I went to get one out of the fridge. After that I cleared up, mum took the wine into the living room where I joined her to watch a serial we both liked.
'you seem quite comfortable this evening'
It was true, I was more relaxed than I had felt in months 'it's nice just sitting here watching TV with you'
'But we have done that many times before'
'we have' I agreed.
'so if you want do this again then I shall be ok with it'
I looked at her with a puzzled expression on my made up face.
'Maybe buy your own clothes and like I say, a darker lipstick'
I took a long look at her before answering 'and you are sure about me wearing a dress?'
'Maybe not sure, but it is nice to see you relaxed, you do look very pretty, and you have been a great help this evening. So yes if you want to be a girl, it is fine with me'
I got lost in my thoughts considering what had happened, coming to the conclusion that I would like to wear a dress more often, maybe not in memory of my sister, but because I liked how I felt while dressed and I liked how I was getting on with mum now I was in a dress. But maybe wearing my dead sister's clothes is a bit strange, perhaps I shall be online during the week seeing what sort of dress I might like to wear next weekend.
I was at that awkward age, hormones everywhere, half child half adult and being a right pain.
I had let me hair grow out of neglect really, I could not be bothered getting it cut so it just got longer and as my father increasingly got annoyed with my unkempt style it had the added pleasure of winding him up.
That was until I was seventeen, and at breakfast the issue of my hair came up again only this time mum made the comment that the ends were splitting and I should get it cut, at least a trim or the whole lot will end up a frizz. She showed me what she meant as she examined a few strands of my hair. Then father chipped in 'No way are you going to John's (his barber) Liz can take you to her salon, I guess they will hardly notice the difference seeing how you look like a girl.'
Mum stood up for me 'Fred that is unkind, he doesn’t look like a girl.'
'Well I bet if he gets his ends trimmed and give him a nice style you could not tell the difference.'
'Fred stop it, do you want him to look like a girl?'
'Might as well accept he does not look like a boy anymore.'
'He does.'
'I bet if he had one of those long wavy styles like you he would look like our daughter, if we had one.'
I decided it was time for me to get involved 'do I get a say in this?'
Father just stared at me 'Yes you get to choose, a cut like mine or a style like your mother's.'
He was really winding me up, how could he threaten me like this, I was old enough to make my own decisions. Then out of spite and bloody mindedness I made my decision. 'Mum, I think I would like to go to see your hairdresser.' Whether I did or not, it was worth it to see father's face go a bright red with frustration.
As he stormed out his last words were 'Why not dye it the same colour as well!!'
Two days later on the Saturday morning my fate was sealed. Without checking with me first, mum had gone ahead and made an appointment for me, she later said my father was being unreasonable and needed to be shown he can't always dictate how others look and behave. Some of my bloody mindedness had faded but when the trip was mentioned to father he made some comment about me being his girl which just helped fire me up again.
At the salon, mum had a chat with a woman called Dee who kept on looking over at me and saying 'yes' in a questioning tone. Then mum left us and I was settled into a chair, 'You sure you want me to do this? she asked.
I just replied 'My father's idea.'
'And you are happy with what Liz has asked me to do?'
'Can't be that bad can it?'
'Well no, not if you were a girl.'
'I just want to see his face when I get home.'
'OK then, let's get started a good wash, sort out those ends and then we see about colour and style.'
Well I never knew what to expect in terms of how long or what would happen, so I just sat back and allowed Dee to get on with whatever she was planning to do, all I expected was for my hair to look something like mum's at the end. How bad could that be, but then this is a teenage mind thinking not quite straight.
This is a studio shot of mum and though I thought it was great on her, when Dee showed me the finished cut on me I was stunned. My dark hair was gone, the tucked behind the ears look a distant memory, true I did not have the makeup but at a glance I was very much looking like a girl, and a good looking one as well. Mum came to collect a short while after, I spent this time feeling very self conscious as I was sat in the front of the street window for all to see.
'You could be sisters' Dee told mum when she arrived.
'Give over he is 20 years younger than me.' and they both giggled at the thought.
Turning to me 'Right then let's go and see what your father has to say now. You do know what you have done don't you?'
'Yes, I called his bluff.'
'Oh more than that, you questioned his authority fair enough, but you are also making other statements about your sexuality and how you see him as a role model. Anyway we had better go and face the music. It does look fantastic though, Dee always does a nice job.'
Father went virtually apoplectic, phrases such as 'no son of mine', gay, queer, nancy boy, even 'why not go the whole hog and wear a dress. At this point I retreated to my bedroom and left him to simmer down. I stood in front of my mirror and played with my new hair, it was really quite nice, I liked how it held its shape and yet I could run my fingers through it, and sweep it from my face, and even though I had had long hair for ages the way it tickled my neck and shoulders was a delight.
Later on Pete a friend called round, I was not sure how the hair would be accepted but after I had explained how it had happened he just said 'cool, does look like your mum's' and that I thought that would be that, only it wasn't. We chatted about some course work we were supposed to be doing jointly when he came out with a ridiculous but fun sounding idea. We go round to his house, borrow some of his sister's clothes and he takes me out as his girlfriend and we see how many of our mates recognise me. After a few moments of 'are you serious' and a call to his sister. There was nothing left to do but tell my mum not to wait up I was going round to Pete's and maybe onto some friends.
Kate, Pete's sister was 20 and a drama student back for the weekend. She loved the new hair and asked why, I told her. Then asked a few personal questions centred on me being a Pete's girlfriend. Then she got to work. She decided that I did not have time to do the job properly, so according to her, if I do it again I would need to shave my arms and legs, pluck my eyebrows better, get my nails manicured and maybe get a tan as I look so pale. But for now, long pants, long sleeve blouse, flats as she did not think I would cope with heels and a full face makeup. We made up a story about me being my cousin and over for the weekend, for ease this cousin, Becky, just happened to do the same courses as me. By eight I was ready, Pete and his sister rated me a 9/10, 'room for improvement then?'
'Not much but with more time I could make you into a stunner.'
I was concerned about this ease with which I was being considered good looking as a girl. 'Just the once and it is for a joke. Right.' 'Whatever you say Becky.'
Pete was 18 and could go to the pub, I was a few months off but a coke would be fine and I certainly did not want to be asked for ID. As we walked in Pete took my hand 'now remember Becky, you are a girl, we meet at a party last week.'
'OK OK, I got it.' I replied in my softest voice.
'Oh and that voice, sweet with just the right amount of huskiness, so sexy.'
'Stop Pete, just get me a coke.'
The evening was great fun, there were half a dozen of our college mates there and not one of them recognised me at first. By the end of the evening Pete had stopped pretending to be my boyfriend and we were just mates having a laugh, what was nice was that I never bought a drink even though I had cash in my handbag all the lads treated me as an honorary girl.
The walk home was interesting, three off us set off in my direction, Pete, Sam and me. We dropped Pete at his house, I promised to return the clothes in the morning, Sam then insisted he walk me to my home stating that girls do not walk alone at night and given my current look could be mistaken for a girl very easily. He then went on to compliment me on looking so good, asking if I had done it before and would I do it again, when I said no, he said shame because I looked better than many of the girls at college. I did ask if that was meant as a compliment. He confirmed it was.
Well that was where the fun stopped, I let myself in and found my parents still up watching a film on TV.
'Good night?' mum asked.
'Yes thanks.' but I forgot to alter my voice.
'Sean, a minute please.' I stood at the door hoping not to be seen, there was no way them seeing me like this would go well, I was sure they would not see it as a joke. 'My god what are you wearing? My dad was staring straight at me.
Rather lamely I tried 'It was for a laugh, Pete's idea.'
'Where did you get the clothes?'
'Kate.'
'And she did not mind?'
'No.'
‘and you have been outside like that?'
'Yes.'
That was it, the TV went off, I was told to sit in front of them, unfortunately I was so nervous I sat as I always did when in similar situation, I perched on the edge of the seat, tucked my feet under the chair, played with my fingers in my lap and looked down at them. On reflection a very feminine pose. Father went sarcastic when I told him I was wearing trousers because my legs needed a shave, 'Well maybe you get them waxed.' I was humiliated, far worse than the initial time at the salon, I just wanted out of this situation really, but the more they went on at me the more I felt my resistance building until I told them I actually like looking like a girl, it was far better than being a son. It was then mum told me she was going to have had my hair returned to my original 'style', but if I liked it so much then she would cancel and I could see how it much I like on Monday when I go to my classes. I tried stomping out of the room but with such thin soled shoes on it hurt. 'My makeup remover is in the cupboard under the sink.' These were the last words I heard of them that evening, but I could hear them talking for ages after, their voices raised at times. I had clearly caused friction between them.
The next morning my hair looked the same colour as before but the style was not as good even after a good brushing. Father just glared at me most of the day, mum caught me alone and more gently asked if it had been for a joke which I confirmed, but then told me I did in fact look really good as Becky and thought it a shame it was just a one off. Then there were the texts, friends congratulating me on a brilliant effort, Matt even asked if I would do it again for him and Sam very nearly asked me out on a date. Now I was confused. Did people actually think I wanted to dress like a girl?
Monday at college had its awkward moments as you might expect, my hair still looked very feminine, I could not sweep it behind my ears without it almost immediately coming forward, and that was without the short fringe hairs not even reaching my ears and framing my face. One unfunny teacher asked if I was a new student, Sinead perhaps. Several students pointed and made whispered remarks but nothing to hostile, a few girls asked where I had had it done, I never worked out if I was being teased or they were genuine. Anyway by the end of the week things seemed to have settled down and my hair raised hardly a comment. And after initially trying to push it behind my ears I spent time teaching myself how to use the products Dee had sold me so I could maintain the style she had created for me.
Well six weeks must have passed, my hair was still cause for a little comment which I tended to play along with by doing exaggerated girlie gestures, a la Ms Piggy. Father had pretty much calmed down as well, so I was surprised how things went when mum asked if I was going to keep my hair like it was, because if I was the roots need doing.
'Don't encourage him, bad enough he has long hair like yours, what next a facial, waxing a spray tan perhaps, why not suggest he grows his nails like you as well.'
He was just so over the top my immediate reaction was to contradict my own plans, which had been to dye it back to something like my natural colour, but with this tirade my back stiffened. 'Well I like it, and the more you hate it the more I shall enjoy it!' And with that got up and walked out to voices saying things like 'now see what you have done'
I called Dee and asked her if she would do my roots for me, surprised at the request but still able to say yes, I turned up on time at the weekend and had lovely head massage as well as having my hair restored back to it's former glory. I got home to a tense father, 'my god he has done it, I don't believe it why would a lad want such a haircut?'
'Because I like it.' I calmly replied.
'Next you will be telling me you have a boyfriend.'
Why I said what I did I am not sure 'What if I did, plenty of gay couples about you know.'
'But Sean you are a lad, you are supposed to fancy girls not act like one.'
'Well maybe I don't want to be a man if you are the model, maybe I prefer to follow mum's example.' I said it on the spur of the moment but as soon as it was out I knew it could have devastating effects. He went bright red with rage and stormed off.
Mum spoke up 'that was not very nice, he does love you.'
I just turned to her 'Could I borrow your tweezers and epilator?'
'Pardon, What for?'
'I have some unwanted hair I wish to remove.'
'You can't be serious?'
'I can't say what I just did without following it up with actions, surely that would be a sign of weakness.'
'Oh what the f##k he might stop fighting you if he sees it that way as well.'
Before he could calm down and even consider if removing my body hair and thinning my eyebrows was not a sign of weakness I had done my arms and legs, mum even offered to do my brows as she said it takes time to learn which hairs to remove for the best shape. She did not go mad but they were neater, thinner, higher and a bit farther apart.
'Mum' I asked as she plucked away 'do you think I will ever grow a beard?'
'You dad can't, so I guess you will be the same. Why?'
'Oh nothing just day dreaming.'
'Does this dreaming involve makeup?'
'Could do.'
'Well if you ever want, and I hope for your father's sake you don't, to try makeup, please ask me, I shall try and help you and hopefully stop you looking dreadful.'
'Thanks mum ' I smiled 'I might just take you up on that.' she did not smile back.
That evening I happened to be at Pete's and his sister Kate was there, we had not seen each other since she had dressed me up and immediately noticed that my hair was looking far better than it should after six weeks.
'Had my roots done today.'
'Oh' she replied 'and the eyebrows are looking very neat.'
'Yes my dad wound me up.'
'So you plucked your eyebrows.'
'No my mum did actually.'
'Your mother did, wow, she did a good job, anything else Becky (that was the first time since I had dressed that anyone had used that name) has been doing.' I slid my sleeve up to show her my arms 'and your pits?' I nodded, 'serious stuff, do you want to dress up again?'
'Not really I just do it to annoy dad.'
'Oh sure!' she then went on to suggest I was enjoying my feminine side and that mum was not as resistant as she might be, encouraging even. Then Pete joined in with a blow for any male ego, Sam, our friend, had commented quite a bit on how good I had looked in the pub, even speculating on if I would do it again, he had even been asked if he fancied me which he denied according to Pete.
'Besides your father Becky it would seem there are few barriers to you getting out there and enjoying yourself.' Kate concluded. That I hoped would be an end to all this 'me being a girl' stuff.
It was warm the next day and I wore shorts and a tee to sit outside while I studied. That was until the peace was shattered by father walking past.
'You did it then.'
'Did what, shaved yourself like a girl.'
'Oh that, yes,' then because he was being so anti, or maybe because it was true 'you should try it, makes the skin feel so much nicer.'
'You think all this is a joke, the hair the shaving.'
'No joke I assure you.'
'So what next, long nails, makeup maybe a dress just too really wind me up?'
'You are winding yourself up without my help, but if I wanted too I would see no reason to pay attention to my appearance so I look (I nearly said better but pretty came out)'
He walked off calling for mum 'Liz have a word with that son he wants to look pretty, give me strength.'
Mum came out with a cold drink and sat beside me. 'Oh I do wish you two would stop fighting.'
'Not me mum, all him wanting me to be the alpha male.'
'Oh I know you are not like him in many ways, both stubborn though.'
'Mum can I ask you a question,’ she nodded 'why did you help me yesterday?'
'Wanted to make sure you did not make a mess.'
'Nothing to do with you quite liking me being a bit feminine, a substitute daughter perhaps?'
'Can't deny I would have liked a sister for you, but we could only have you.'
'I know, but you did my brows and did offer to show me makeup.'
'No that was just a caution to stop you making a mess. No if you was to push this as far as I think it might go, then I would expect you to do it properly, men in skirts who look like men, well besides Scots in kilts, look well, weird. If you ever wear a dress and I have anything to do with it you would have to look like a girl.' then she seemed to look into the distance, 'perhaps I do miss not having a daughter.' then she snapped out of it 'that is still no reason to wind your father up.'
It was now time to tease her 'so mummy if I got myself a nice dress you would help me look pretty.'
'Don't twist my words.'
'But Sam has been asking if I would go out with him and I was thinking of saying yes, and it would be brilliant if you would just make sure I do it right, don't want to look like a clown do I.'
'You what, is this really true, you are winding me up?'
'Nope apparently Sam fancies Becky.'
'I hope you told him no.'
‘not had chance, but why not?'
'Just not right.'
'But your friends Shirl and Jane are gay, why not me?' I was making this up as I went enjoying the reaction I was getting.
'That's different.'
'Not really, so if Sam was to ask would you mind helping me?'
She had had enough, she got up and walked away clearly annoyed with me or herself, maybe both.
The subject of how I looked did not come up again, an uneasy peace descended for a couple of weeks. I kept up my hair grooming regime because I liked the attention and the way it looked when finished, I even tweezed out a few more hairs making the brows thinner, and even though no one had noticed yet I was filing my nails rather than clipping them. Then two things happened separately but together made for big change. First dad told us that he had been asked by work to do a site job, he usually avoided these but maybe he wanted a break from home, anyway it would mean 10 days away. Mum made all the right noises I just felt relieved that I would not be confronted with his attitude for a bit. The second thing which unexpectedly coincided with this was some friends calling round when mum was home, she knew a few of them including Sam and had a casual chat with them before leaving us alone to decide what we were doing that evening. Later Sam caught me on my own and relayed an odd conversation he had with my mother, in a round about way she asked Sam what he thought of Becky, being blunt Sam had said it had been a good bit of fun, but got the feeling she was up to something. Later on after he had had a beer and me a coke, he asked if I still dressed up, I said no, he said shame, he could do with a partner for a party he had been invited to. I automatically said 'what, you take a girlfriend not a mate to a party.' Then the penny dropped, he was inviting Becky. 'Are you serious?' he nodded 'but it was not for real, we let you know after a bit.'
'Yes, but you were believable, and I could do with someone to keep me company, and I think your mum would help.'
'What' I looked at him open mouthed. Then Matt and Pete joined us, quickly picked up the conversation and confirmed I could pull it off and from stories Sam had told of these parties his parents took him to, Sam could do with a friend for company. I felt cornered even my mates wanted me to be a girl, at least for Sam. It was when I got home that I really felt the pressure.
'Sam is a nice lad.' mum commented.
'I know a good laugh. Why do you ask?'
'He was the one you said fancies Becky the other week when you were winding me up.'
'Yes that is the Sam who' I swallowed nervously 'fancies Becky.'
'I was just thinking, what with your dad away and you on half term holidays' now it was her turn to swallow nervously 'do you think Sam would like to meet Becky again?'
I stared straight at her 'Mum, what are you saying?' I was starting to sweat and possibly blush.
She took both my hands and took a moment to look at my neat nails, then she looked me in the eye, 'I suppose I would like to challenge you to be as feminine as possible. Then you might get these silly notions out of your head and your father can relax around you again.'
'But what if I like it?' I asked rather cheekily, thinking that I might.
'A risk I am prepared to take.'
I swallowed hard not sure how my next words might be taken 'Sam has asked if Becky would go to a party with him.'
'I suppose that is a good focus for us. When?'
'While dad is away.'
'Perfect, I suppose. Do his parents know who Becky really is?'
'I have only met his mum once, don't know what Sam will tell them.'
'Right if my plan is going to work you are going to have to accept whatever I suggest, no questions, no sulks, and no fights. You do what I say and you will be the best girlfriend I can make out of you for Sam.'
It was my turn to be nervous, if I accepted without asking what she planned I could be letting myself in for all sorts of trouble, if I say no then they have won I will have backed down. I said nothing at first, looked at my feet, then at mum's high heels, then moving up, her skirt, soft blouse, until I reached her smiling face. 'A deal' she asked.
'A deal' I confirmed, feeling my confidence ebb from me.
'Ok your father is away from Tuesday, you break up?'
'Already finished.' I interrupted.
'In that case, while we are at work on Monday you will go shopping for some clothes, your choice but you will need panties and bras as well as at least one pair of shoes and some outer clothes.'
It was at that moment I thought that maybe I had bitten off more than I could cope with, mucking about as Becky was one thing, shopping for girls clothes and having to be subject to mum's rules was another.
Monday I did after much careful planning and working out where to shop without being too closely watched, I finally got home with a pack of panties, three bras, a pack of tights, one pair of denim shorts and a plain white tee. Along with a pair of black flats. I also had a visit from Sam who was certainly pleased that I had agreed to his request, even offering to cover some of the costs.
Tuesday, mum told me flats would be no good for a party I needed heels, the higher the better, then suggested I take Sam and let him choose. It was my first day in girls’ underwear and though I did not fill the bra I felt rather self conscious that the cups might be showing. Sam chose black platforms, peep toe, sling backs and a towering spike for a heel. Mum smiled at his choice and asked if I had tried them on, I said they were really difficult to balance and walk in, she just told me I had till the party to get used to them. Tough.
Wednesday, dad has gone, mum has made me wear my girl’s clothes including the heels and told me that she expects a daughter to help about the house and gave me a list of cleaning jobs she wanted doing. By the time she came home I was shattered and my feet sore. Mum just remarked 'Not so easy?'
Thursday, I slept in a satin nightie mum lent me, that was very nice. She had given me a quick run through of what cosmetics she has, then told me that with the aid of a book I should practice a daytime look and one for the party. she also lent me her maxi dress for the day. My first ever dress and it was quite awkward to get used to I can tell you. I had tea ready for her when she got home and my face done as well as could manage.
Friday. I had to go out dressed, she allowed me a pair of her flip flop sandals. My fright for that day was to go to a shop called Nailz and get my nails done. Sam said he would pay but when he booked did not know what he was asking for. I came out with french tips extending at least 5mm past my regular length. Oh and pink toe nails.
Saturday. We were up early mum wanted to go shopping for a dress, she had me wear the maxi again and do my makeup again. I was hoping for a quick in, pick pay and leave shop. No mum said girls shop slowly, probably going back to the first thing they saw but the pleasure is in wandering around just looking and hoping something strikes you as perfect. Well I was not sure it was perfect but she chose a green dress that I felt looked ok when I tried it on for her. Next she took me to Dee's who smiled at mum then nodded to me, 'Becky is in safe hands here Liz, don't worry, see you later.' Mum left me there stood in the reception area 'Well Becky this is a turn up, did think you might be in for a trim and roots, but your mum tells me you have a date.'
'Not quite, helping a mate out.' I put in
'If you are getting all dressed up, in my books that is a date. Now we have discussed what should look good on you, so just sit back and let me get on.' As before I rather liked the attention Dee gave me as she did my hair. I had no idea what to expect, but was not surprised to see my hair change to a blonde and sweep back and down my back more than before.
Last thing on mum's list was to get me home, changed and ready for Sam picking me up at seven. I was presented with a skin coloured long line strapless bra, a pair of control panties to start with, then a suspender belt (might as well have the full works was her reasoning), sheer shiny stockings, then the green dress. The satin fabric felt really nice to touch and I was fondling the skirt possibly too much. Mum lent me a short gold necklace, a ladies watch, a bracelet to match the necklace and a couple of dress rings. To finish me off she clipped on ear rings (they hurt), sprayed me with perfume and made me walk up and down in my heels till I had got the dress to swish as I walked. Last a black shawl and small black clutch bag which she had filled with my phone, some cash, a lipstick, small brush and most shocking a tampon ( a girl should always be prepared) and a condom (for the same reason) I just stood open mouthed that she could even think I might use them.
I was ready and in truth actually felt I looked very good, the dress felt weird with its straight skirt and one bare shoulder, but it looked good and that is what mattered. Sam turned up on time looking very smart in a suit. He did not hold back on the compliments as he admired his partner for the evening.
Then mum interrupted 'Right one thing you two have not practiced I think is being a couple, right let's see you hold hands.' 'Sam put your arm round her like you want her.' 'Becky, look up at him, you are supposed to be his girlfriend, act like one.' 'Ok try kissing.'
I baulked at this.
'Becky remembers the deal, now kiss.' 'No not a peck, like you want more.' 'Sam that is better, think of it as foreplay.'
'Mother' I exclaimed.
'Well it is, so just kiss with the thought of what might happen later if you were a real couple.'
After a few rather intense kisses and a repair to my lips we were told we our body language could do with improvement but it was ok. So mum wished us a good evening and hoped we both had a good time at the party.
The party was organised by Sam's father's company and had been an annual event for years but this year, for Sam at least it would be more interesting as he had someone other than his parents to talk to. It was not too far to the venue and after our role playing with mum we had time to discuss how we should be behaving. Clearly a couple should sit together but how far we should go in the touching and affection ratings was what we differed on, Sam wanted to give the image of 'a pretty girl on his arm', I was happy with being mates not every couple are at it all the time, I argued. As we parked Sam suggested we try kissing again, only this time I think of myself not as a lad but as a partner who is more than just a mate, maybe a lover or at least thinking of it, maybe even think of myself a girl. Maybe I could think of being submissive and trying to please him, or imagine I actually wanted him and would take any opportunity to show that desire. I laughed at the last one, so he asked what do I see, I replied that I saw a good looking guy, he told me I was a good looking girl so what is stopping us being a good looking couple.
'Ok you kiss me in a way that you want to.' He touched my lips so gently it sent shivers down my spine, I responded gently as well.
'That was better' he whispered.
'You kiss like that and I will have no problems.' our lips touched again, I felt all my frustrations that had brought me to this situation flow out of my body, I had cornered myself into this ridiculous situation where I dress as girl rather than back down in front of my parents, and now a kiss off a mate is melting my soul. His tongue flickered along my lips and without planning it I put my hand round his neck and let my tongue meet his. It all happened within a minute but felt like ages.
I broke 'Oh, come on Sam, I think it is time we were getting inside.' He kissed me gently once more then got out of the car coming round to my side to help me out as I struggled to get to my feet. I had no problem after that kiss holding his hand as we walked across the car park and to our seats next to his parents.
I had got myself into a frame of mind that I was playing the part of a girlfriend and just played the role, Sam had made it easier with that kiss, but I still had to remember the walk, the elegant sit, the eating, the smile, the voice. All those things I had had drilled into me by my mother over the past few days, looking back I would not say I was accomplished just reasonably good. Sam's parents were nice, his mum was very pretty and chatty, his father was charming and in a way I could see Sam following his father's charm. Besides being the first time out as a dressed up girl with no one knowing, it was also the first time I had more than a sip of champagne to celebrate a toast. I drank white wine because I knew it was a girls drink, I finished the champagne because I liked it. The alcohol and the general mood of the party relaxed me so I enjoyed myself far more than I could have possibly imagined, I even danced with Sam and managed a slow waltz sort of shuffle with his dad. A rather unexpected moment was when I felt like some fresh air and Sam went with me to stand on the balcony, as we stood there next to one another, looking over the city, I felt his arm cuddle my waist, I responded by moving closer so he could hold me tighter. I was telling myself it was part of the act but I would have been lying if I did not admit to rather liking the feeling of having a strong man holding me making me feel wanted and secure. I happened to look up just as he looked down, maybe I meant to or maybe it was an accident but our lips meet and this time I did not need to act, he made me feel like a girl, at that moment I was his girlfriend. The evening might have just been a wonderful new experience that was like nothing I had ever done before, maybe I could have just walked away from this cross dressing world except for an unexpected invite. During the meal Sam's mother who as I say was chatty casually invited me to go round the day after. I can only guess I had been to convincing as a girlfriend and she had believed the act and wanted to maybe get to know me better or give Sam more time with me, I was not sure but even though I had said I was not stopping around she seemed quite keen for me be Sam's girlfriend.
Mum was waiting up when I got home but gratefully was not peeping through the curtains when we parked outside and Sam gave me a goodnight kiss, I am sure she would have seen that as unnecessary, for that evening it seemed natural, as Sam put it 'If he had taken any other pretty girl out and things had not gone wrong he would hope to have at least a quick kiss.' It was not a quickie, I had to repair my lipstick so mum was not alerted to the situation. Once inside and Sam gone I had a rather long chat with mum about the evening, the people I meet, the venue, the food, the hassle of being a girl. I was trying to be as negative as possible, she had put me through this to try and make me be more manly in my appearance so I lied to myself and her when I told her the shoes were terrible, the nails inconvenient, the skirt a hassle etc etc. But in truth I had really enjoyed the challenge and had enjoyed looking attractive, something I had never considered I could be as a lad. But there was one thing I dreaded telling her, the invite to go round to Sam's the day after, I knew she would not like this turn up and I was right. She complained to start but I explained how I had declined and said I was going home i.e. Becky the cousin was going away but his mum insisted and Sam said Becky could easily stay another day at least. She accepted that I tried to get out of the invite, though in reality I did not fight too hard. Mum however pointed out that I only had the dress I was sat in and some shorts so what would I wear next. I flattered mum by telling her she had some great clothes and I could just borrow something of hers for the afternoon. There was no answer, she was thinking about how the night had turned out and just reminded me to clean off my makeup before going to bed.
I had a strange night, while I was awake I went over and over the events of the evening in my mind and when I was asleep I was dreaming of long flowing dresses and standing on hilltops in the breeze, or big strong men often looking like Sam in romantic situations with me dressed in really pretty dresses. I was shattered when I got up feeling like I needed to go back to bed.
I was greeted in the morning with a very feminine hair style that without much brushing fell back into the shape Dee had created, and when I looked at my face it was clear I had not been thorough the night before, my eyes still had a darkness to them and my lips a redness that I was unfamiliar with. I was also greeted in the kitchen by a mother who had not slept well either, but for completely different reasons I guessed.
Her first words were 'is there any way you can get out of this invite?'
'I told you last night, she is very persuasive and Sam would like me go as well.'
'So you can't just call and say something like, you had to go for this or that reason.'
'No I can't, I said I would go and I would like to go, please help me'
''Ok if I can't persuade you not to go, then same rules apply, you do as I say'
'Fine with me.'
'Right any idea of a look you want?'
Mum was a woman who liked clothes and looking good and was a good role model for anyone wanting to be feminine, so I rather allowed her to chose, I would have loved a long gown but I knew that would inappropriate for such an invite, but when she gave me the rather plain outfit to wear I did feel I wished I had taken a more positive approach.
But I was wrong, the white blouse was lovely soft cotton and the mini something any teenager with nice legs would be to wear. She made me wear the heels, so I don't forget to behave like a girl. By one o'clock I was ready, my hair perfect, face redone, more training on how to gesture and move like a girl. Sam turned up in his car again because I did not fancy walking out onto the road looking like this and maybe meeting a neighbour. So I was ferried the short distance to his house. I had not invited him in just in case mum had a go at him, and just in case he tried to kiss me without it being part of mum's coaching like the night before.
'You look nice Becky.'
'Thanks' he leant towards me 'not here, mum might be watching.'
'Ok, but am I still your boyfriend?'
'Would you like to be?'
'Oh, yes please'
'In that case boyfriend, please take me to your home.'
The afternoon was just as I expected polite conversation with Sam's parents, along with periods of time when Sam sat in the garden alone with me just talking about our studies, friends, TV programmes, just about anything you would expect two teenagers to talk about. There was one extra topic though, how it felt to be dressed as a girl. Without trying to appear too keen or letting him know how much I actually enjoyed being Becky and being with him as Becky, I told him about the preparations I had gone through to achieve this level of femininity, about how it feels to walk in heels, about how fabrics and women's clothes feel on hairless skin. He flattered me whenever there was the opportunity which always boosted my confidence, but possibly best of all was just being accepted as someone different, Becky, by his parents, I was no longer just a mate of Sam, another lad, I was Becky, his girlfriend. That was until late in the afternoon as I was helping clear away the pots with his mother on our own that we had a 'Becky can I tell you something in confidence' talk. She explained how she was so relieved that Sam had found a partner that suited his needs, I was confused and a little concerned how this was going as she told me about some gay magazines she had found in his room, and then asked when I had first been Becky. I was in tears as I realised she had seen through the disguise but she comforted me telling me I was really very good, my height and size clearly helped but I did one or two things which alerted her, mostly my knowledge of Sam's courses when I was supposed to live away. I was told not to mention that she had rumbled me and that if I was happy being Becky then she was happy for me to go out with her son. She left me for a while to let this revelation sink in, not only did she approve of a cross dressing boy, but was fine about her son being gay, two things I would have never considered even that morning.
At the end of the evening I walked home with Sam and because of the way the day, even the weekend had gone, I took an 'I don't care' attitude to being seen by anyone I might know. I was on a high and loved being dressed as a girl, being treated as a girl and looking forward to more opportunities to be Becky. Something in me had changed, before I was being a belligerent teenager, now I was loving what that fight had created.
As soon as I walked in mum realised I had walked home and I was holding Sam's hand which was another clue. After a few minutes I kissed Sam and said 'good night' because I knew there was going to be a conversation with mum and it could go either way, good or bad.
Where to go from here.
1. Move in with Sam, get a summer job working for his parents.
2. His parents have a big bust up, separate, he goes to live with his mum who insists that he live as a daughter.
3. Dad backs down and accepts, has some skeleton in the cupboard that caused him to over react, ie, gay friend who died and he feels guilty.
Two friends who grow up together, but as puberty hits their relationship changes, and there is always the contest that will affect how they go from firm friends to lovers.
Our relationship started when we were in reception class, the teacher made us sit in alphabetic order and because my name is Kyle and my soon to be best friend was Kylie we ended up sitting next to one another whenever we sat at desks. This was the start of a very strong friendship. We went through school and childhood as close friends in a very asexual way we shared everything and did everything together. When I played football in the playground Kylie joined in and was able to put some of the boys to shame, and when the girls played netball in games lessons she would get me to make up numbers if they were one short. Neither of us thought this strange. Neither did we find it strange that in the summer we could go into the woods near our homes and come back covered in mud after playing in the boggier bits, but we had also picked some pretty flowers to take home for our mothers.
Kylie got called a tomboy, I got called a sissy by other children. Being a tomboy can be flattering, but sissy is not so generous and got me and Kylie into fights on occasion, the outcome being our bond got stronger, and name calling stopped as anyone who knew us was not going to name call us twice.
We had ten years of innocent childhood just being best friends, Kylie was a girl, I was a boy but it made no difference we just got on so well together. The first signs of us growing up came when Kylie was asked to be a bridesmaid for her sister, she had started to change physically about 2 years before and her personality on reflection had altered with it, we did less of the childish mucking about but I grew up with her. We started to do baby sitting jobs together, walking dogs together, no one that saw us thought anything of it. We could have been two girls enjoying the friendship, or for that matter two boys.
The friendship was changing though, Kylie was discovering that clothes did not need to be jeans and loose tops there were other styles just as appealing and comfortable, and I was discovering sport a little more and had joined a cycle club which took me out with new friends. We were still close, just our other friends seemed to be changing. Kylie's body was getting hit with hormones and her moods could be difficult, not having a sister I had no idea why she would refuse to see me some days until my mother explained about periods and every woman's monthly nightmare. I learnt to be more understanding but forgot regularly why she could be grisly for no reason until the penny dropped.
The wedding did open up a whole new side to our friendship, because of our friendship, our families knew each other quite well from the constant contact, so me and my parents were invited to the evening reception, not the smaller sit down do in the afternoon but the evening dance and cake cutting bit. I was not that pleased when a few weeks before I was told I needed new clothes for this occasion, and school trousers and a clean shirt would not do. I ended up with a pair of trousers unsuitable for school while at the same time could not be worn for going out with mates, plus a jacket that I had no intention of wearing more than the once and that would only be from the car to the reception room. I felt really awkward in my clothes but when I found out what Kylie was going to wear I had some sympathy for her. It was full length to the floor, very straight with a split up the back so she could walk, a laced waist that made her look stiff with a ruffled fabric around her bust and small capped sleeves. My mother helped me with a few of those details at the time. All in cerise or dark pink as I called it, but my biggest sympathy went out to her when she showed me the shoes she had to wear. Really high courts in a matching colour, even though she was not always wearing jeans then, she was nearly always in trainers, so these would be hard work I expected.
The day of the wedding I kept well away not wishing to get in anyone's way, so until I had to get ready I avoided being seen and took myself round to John's to play on his X box. My discomfort at wearing the new clothes and being told I looked ever so smart was forgotten when I arrived at the reception. My family found the bride and groom, gave them a gift and thanked the parents for inviting us, then I saw Kylie, I knew it was her but she had been transformed, her hair styled and laced with flowers, her face made up, her female figure evident to all and looking very nice, she even had long polished nails. I did not know how to say it, but she was beautiful.
Later on we sat together and enjoyed a coke chatting about the day and how things had been, she said she was not mad keen on the dressing up and would rather be in jeans, but I could see she enjoyed looking good and getting compliments of lots of people. The shock I think for both of us was that her sister got us both to go on the dance floor and dance together, neither of us knew how to dance, but we had seen it on tele so made it up and copied others. This was my first dance with anyone other than my mother and definitely the first with a girl and I felt good being with Kylie looking so great, I even told her so, which got a kiss in return, creating a blush in my face. But it was only the start, we ended going outside when she felt hot and wanted some fresh air, then as we stood on a terrace I felt her hand link my arm so I responded and copied what I had seen in films. Clumsily we held hands, then got around to a cuddle of sorts, eventually when we felt we had been out long enough, we managed a quick kiss on the lips before joining the party hoping no one had seen us doing anything.
Besides a few guilty feelings, for me that was about it for the wedding. However those hours spent together dressed up had changed our lives. We still meet up at school, and we still spent evenings and weekends together but now we would go for walks and sit on benches letting our fingers touch and loving the sensation of that touch. We also, in the interests of education, practised kissing, saying that one day we would need to know how to kiss on a date. The whole experience was rather surreal and interesting, we were not dating but in a way we were. If we ever discussed the touching and kissing we just laughed it off as a game, but if we had been honest we would have admitted to liking the new side to our friendship.
We were now sixteen and had taken our GCSE exams and had a summer of doing student jobs and lying on a nearby hillside watching the clouds go by, my cycling took a back seat, and my wardrobe took a few new items with the money I was earning. Kylie would come shopping with me to make sure I bought nothing to stupid, and she was wearing more flattering clothes which made her far prettier than I ever realised.
Come the start of the new term and having got the grades we expected, a whole new world of college opened up to us. We went along to register on the courses we wanted to do, then looked around at what else there was to get involved in, there were a few social clubs which did not appeal, but there was an advert that took Kylie's interest. 'Womanless beauty contest' I was not that enthusiastic, the whole idea was to have some fun dressing as the opposite sex and then go on stage and take part in a contest to see who is the best. Kylie was talking about it all the way home, how we could go as each other, we were similar sizes, I pointed out she had changed a lot of late and had a very different shape to me, which she dismissed, I said I had nothing to wear, she said she did so I could borrow a dress of her. We walked into my house still arguing and finding my mother in a relaxed mood, she asked her what she thought of a womanless contest. Kylie had to explain what the contest was, but once my mother had understood she just gave me a big grin and said it would be a wonderful idea, she even pointed out that I had once said how nice Kylie looked in her dress, so why should I not look good as well. I felt resistance was futile and gave in but planned on ways to get out of this potentially embarrassing situation.
There was a few weeks until the fateful date and my first plan was to keep quiet hoping the barmy idea would be dropped or just fade away. I was thinking the plan had worked when the two most important females in my life were found discussing the practical issues around making me look like a girl, not just wear a dress. Words like bob cut, c cup, waxing and acrylics all new ones that I had no idea about, I did understand piercing though and felt myself sink. As they noticed me stood at the door I was invited in, I must have looked worried as they started reassuring me that the whole womanless event would be interesting fun, then turned the talk to what Kylie would need to transform herself into a boy.
The remainder of that day was spent letting her borrow my little used jacket and trousers along with a shirt and tie borrowed from my father. Somehow she lost her breasts and with subtle make up changed her face into a more masculine image. The strangest part of this time was having a person with me who I knew was Kylie but looked like a lad. At a deeper level this was quite disturbing, we had always been mates and until recently not considered the gender differences but now the visual change was odd to my senses. But even more worrying was that before she went home she did not change back into her own clothes, she packed them into a bag and walked home in my stuff. She wanted to find out how her parents would react to the new Kylie she said.
The following day at college she was full of how much she had enjoyed herself the day before, her mother had not made much comment about the male Kylie walking in the door, I had thought her mum had been a motivator behind the more girlie Kylie, now I was not so sure. Her good mood was a precursor to the activities that overtook my life later that day. Based on the argument 'I did it yesterday, so it is your turn today' when we were finished with our classes that afternoon I found myself at Kylie's house and being treated to my first experience of a girls personal care.
I had been swimming with her before so she had seen me in trunks, but it felt so different in my briefs as I stood in her bedroom. My briefs were not suitable I was told and changed them for some quite insubstantial knickers, I had been putting up a brave fight of resistance but those bright red satin panties destroyed my resolve as I tucked myself into their smooth cool caress. I capitulated within a moment. She next fastened a matching bra around my chest and filled it with socks, that was just tight. The tights I put on next restimulated my senses, she explained how to do it but a combination of the fine material and her helping hand on my thigh was wonderful. The kiss that followed was just as wonderful. When we parted I would have done anything for her, I had never felt like that before and all common sense had gone. Within minutes I was stepping into her long bridesmaid dress and feeling the shiny lining brush over my body, the disappiontment was that it was to small around the waist, but she said close enough to be able to make fit with some adjustments.
My next plunge into feminine preparations was to be sat in her dressing gown while she made up my face, all I could tell was that creams and powders were being brushed onto my skin, it was not until she had finished and seated a long curly wig in my head that I was allowed to see. I stood in front of her full length mirror amazed that the person reflected was actually me, the body had a female curve, the face was pretty and the hair was definitely not male. I looked at her and tried to say how wierd I felt, the whole experience was way out there in the unknowns, for me anyway. She told me I was pretty and kissed me again, this time we were stood up and as she was close I am sure she must have felt my penis making an unwelcome appearance in the satin panties, but she said nothing. It was still early so she gave me a short skirt she sometimes wore and a vest top, then we looked for shoes, she had her bridesmaid shoes, trainers and old school shoes, so we settled for my own trainers and she declared me ready to be called Kylie, I struck a pose and pretended to model for her. I was relaxing and starting to muck about so she invited me to go and watch TV in the lounge with her, her parents were out so I reckoned it would be fine. I had relaxed too much. Sat watching another repeat of Friends the front door opened and in walked her parents. I was paralysed with fear. Kylie was quick to distract them and try to get them away from meeting me, but her mother just said hello as if it was normal to have a boy dressed as a girl in their front room. When I politely said hello back, she replied 'you look very pretty Kyle, you will win this womanless thing, hands down'
I was wanting to escape clean off and go home, but she invited me to stop for tea, not that unusual, but I did not change and spent the evening in the skirt and top, her parents not making anything of my peculiar attire. My next problem was that I needed to go home but Kylie thought I should show my mother how I looked, this took a lot of persausion before I gave in. It was dark and Kylie's mother offered to drive me home, very reluctantly I accepted and ten minutes later found myself being appraised by my mother, who basically agreed with all the previous spectators that I was pretty and would make a good candidate at the contest. To my own surprise I was even feeling more confident that I could pull off my part in this nonsense, but I was not mentioning how nice the clothes were feeling on my unaccustomed body.
The following Saturday was a shock to my normal male lifestyle. First I had to go shopping, something I had done before but never for high heels, mum and Kylie were looking for some shoes to match or coordinate with the dress, and I had to go along and try them on to make sure they fitted. Eventually we found some a pair of thin strappy sandals with the most enormous heel I had ever seen, well not quite, I had seen them on girls but not on Kylie. Then we were off home to have a full rehearsal with the outfit.
I was told to take a shower and use some cream, when it started to tingle I asked what it was and was told to wait another minute before rinsing off, it was then I noticed my body hair swirling down the plug hole, my ego had taken a beating in the shops and now it was being reduced to a whimper. 'My hair is gone' I said in a pathetic vioce.
'What did you expect, how many girls do you know with hairy arms and legs?' my mother informed me 'now use the razor to do your armpits and get any hairs the cream missed. Oh and tidy up between your legs, nothing should show outside your panties.' Being in the bathroom with your mother when you are nearly seventeen is difficult, having her talk about my boy bits even more so. 'You know what I mean don't you?' and gave me a smile. All my fight was gone, I stood in front of the mirror and did my underarms then concentrated on the knicker area. I emerged wearing mum's pink silk kimono and loved the cool softness on my bare skin. Kylie and mother were waiting in mother's bedroom, they were all organised with lots of stuff laid out on the bed, my modesty was preserved when I was handed the red knickers and allowed to put them on in private, returning when the emerging erection had subsided. This was followed with a bra which this time was filled with a pair of silicone forms my mother informed me she had borrowed from a collegaue at work, I just thought who else knows about this. Next I was introduced to the item that would allow the dress to fasten, I knew what a corset was but until then never seen one close up, and as the laces were pulled tighter and tighter until I had a waist the same as Kylie's, I got even closer to this garment. Next was some stockings, even softer than the tights from the other day and fantastic to have on my legs. I was now feeling totally alien with all these strange items on my body, but I knew we had a long way to go yet. Kylie made up my face, while mum painted my nails, fingers and toes once she had removed the stockings. Next was the wig another borrow it seemed, a long straight style with a swept fringe and curling in at the ends in a light brown not quite blonde colour, it was secured then fussed and brushed with until they were both happy. Nearly done and I stepped into the dress, this time the zip ran all the way up my back and fastened. Now I had to balance on my new shoes. Last mother had picked out some jewelry for me, a ladies watch on one wrist, a gold bracelet on the other, a diamond ring on my wedding finger she said it was the only finger it would fit and a ruby on my right hand, a gold chain around my neck with a ruby pendant pointing towards my imagined cleavage and two long gold chains clipped to my ears. I was declared ready and helped to my feet so I could look in the mirror.
Truly amazing was all I could think, I knew I was a boy but looking in the mirror was making the connection between the reflection and what I knew very difficult. Mum said I was looking great and Kylie announced I looked so good she was going to change so as to not miss out in the fun. I had half an hour to wait before my 'boyfriend' was created. The time was spent trying to learn how to walk on such high heels, mum giving me advice on holding my head up, hands out etc until I could walk reasonably confidently along the hall without tripping or stumbling.
Kylie reappeared looking boyish once more, walked up to me, took my hand, kissed my lips and said 'Hello dear, you look fantastic' in a very hollywood actor imitation. Mother was smiling with the joking and started taking pictures with her camera. It was nearly lunchtime and mother suggested we have something to eat but I would need to take the dress off, it was to nice to risk a food accident. So I went upstairs with my boyfriend who helped my out of the dress then still in everything else as I hung the dress up she came behind me and stroked my satin clad arse. 'Darling before we go any further there is one thing I must do' which she followed up with a french kiss and more arse stroking. We broke 'you like this don't you?' I was wanting to say 'no I am doing this to please you' but she touched my erection to let me know she knew I was getting turned on by these activities. She then offered me the clothes I had worn the other night, the short skirt barely covering the stocking tops and the vest top emphasising the fake chest more than seemed decent. As I was fastening the skirt mother shouted up that lunch was ready, my cue to teeter down stairs and let her see that I had not reverted back to being a boy.
I walked into the kitchen not quite sure what reaction I would get and was surprised when she truned to Kylie and said 'Kyle sit down' then turned to me 'Kylie would you sort out something for us to drink'
I made a stunned comment 'muuummm'
Kylie just took up the name reversal 'Can I have coke Kylie. Please'
After that I just accepted I was the girl and got on with it. To be fair even if I had not been dressed that way I would still have sorted out the drinks for us, it was the name change that threw me.
We chatted over our meal and they felt I needed more time in heels so I did not disgrace myself at the contest, and my boyfriend felt she needed more time getting used to the male image as well, so with my mother's blessing I was persauded to stay in the skirt for the rest of the day. We watched sport on the TV and helped mum with some cleaning. My boyfriend went home without changing, later ringing up to ask if me and mother wanted to go round later for supper, but it was clear the invitation was for Kylie the 'girlfriend' to visit, not Kyle the regular me. Mother showed me how to refresh my lip stick and what to put in a small shoulder bag she gave me. I was going outside as a girl and there seemed to be nothing I could do to stop it, and as mother said, I would have to do it for the contest anyway, so I should get used to it in easy stages, starting then.
The evening was not that much an ordeal, Kylie's father did look at me in an odd sort of way, maybe it was difficult for him seeing a lad he had known for years appearing in his daughters clothes and looking pretty good in them, I was not sure. The way our parents can just sit around and chat was not how I imagined the evening to go. We drank wine and talked about anything and everything to do with their lives, then we had some supper and a coffee before mother and myself went home.
The days surprises were not over though. We got home and mum complimented me on how well I had taken to pretending to be a girl, she was still calling me Kylie to reaffirm my look, but the next surprise was the getting ready for bed. I used to undress, clean my teeth, climb between the sheets, sleep. That evening I had to learn about make up removal and skin cleansers, taking off unfamiliar clothes like a corset and a bra, massaging my feet to help them stop aching plus many other little things I never considered before. Thinking I was done, mother then asked if I would like to try something else new, I asked what, and she offered me one of her long silk nightdresses to wear to bed. I said mum with a question in my tone, but she just placed it in my hand and said 'try it'. I did once she had left me alone and boy was it nice, I slid between the sheets wrapped in the soft fabric and replayed the many experiences through my mind as I lay awake wondering what I had opened up inside myself. The Sunday was no less wierd, mum came into my bedroom as I had slept in late, I tried to pull the duvet up but was not quick enough.
'You tried the nightie then?'
I was feeling guilty for some reason, and mumbled a 'yes'
'Nice isn't it'
I did not answer that one.
'So what do you have in mind for today?'
'I have an essay to write for Monday'
'I was thinking more, what were you thinking of wearing, your nails are still painted and it would not take long to sort you out, and besides that you do need to practice walking in the heels'
'Is it really necessary?' I asked
'Well maybe not, but I think you were enjoying yourself more than you let on yesterday or why else would you be wearing that nightie this morning?'
'Ok in the interest of heel walking practise I will wear a skirt, but no corset please.' I was compromising with myself if not with mother.
Half an hour later I was eating breakfast in one of mother's long flowing cotton skirts and a big loose silk top, face made up and wig refixed, off course the shoes buckled to my feet as was the main reason for this days dressing. The skirt took more managing as I had to think about it when I sat down, stooped to pick something up or walked upstairs, the floor sweeping hem and acres of fabric made for a good look but a challenging one as well. The top just had sleeves that I had to keep out of things as they could drape across a table and into something like food if I was not careful.
That evening I had finished my work and then got myself cleaned up early, I wanted to be sure everything about my feminine weekend was erased before I went to bed. I could not regrow body hair and was thankful that college did not do compulsory games like school had done, I just wore long sleeves and knew nobody would see. I did however sleep in the nightie once more, this time I had a lovely dream which was interrupted by the sudden appearance of a damp patch on my stomach, something I later found out was going to happen quite a bit.
I had a relatively quiet week, well if your consider still wearing the satin bedclothes once it had dried after some descrete cleaning and for some reason never getting round to cleaning the polish off my toe nails, as being quiet, but compared to the weekend it was very subdued. My mother encouraged me wear the heels every time I got home and just walk about the house in them so I would become familiar with them, by the Friday I reckoned I was OK in them, or should I say on them. Kylie's week was very different to mine, while I tried to keep quiet about the contest preparations she was wearing more asexual clothes and looking fairly indistinct from a distance, and we were being taken for two lads more often than seemed normal for our relationship. When I mentioned this she said we could always try it the other way at the weekend and get mistaken for two girls, once more I had let myself into a situation I had not planned for and was being manouvred into dressing up again.
My mum said it was a good idea that I spend time as a girl, it would be excellent experience and even went out of her way to buy me a shiny white blouse with short puff sleeves and a pleated short skirt so I had some clothes of my own. I was shocked at this escalation of my dressing up but spent Saturday with Kylie in town walking around the shops and being persauded to buy packs of underwear and some make up. Kylie had even worn a skirt for the day and had bought some more heels so I was not alone on my stilts.
After a meal in Pizza Hut we made our way home, knowing her house would be empty that was our destination. Having drunk wine the weekend before with our parents we sampled some of the alcohol in the house which lead to us getting silly and as Kylie put it playing lesbians, we got quite steamed up and my enjoyment displayed itself in the front of my skirt, this made her laugh that I was too obvious a real girl does not show herself so openly, but followed this up by slipping a hand up my thigh under the hem and into the crutch until she had a hand cupping my privates. I was breathing deeply unable to control myself, we were kissing passionately. The kiss broke and I was left unsure what was happening as she released my throbbing penis, I thought she had had enough, but to my surprise she pulled the skirt up and pulled my tights down. Standing erect she told me she had never seen a penis before and inspected it carefully which made me feel like a specimen, the next shock was that I had closed my eyes trying to regain some compusure when I felt a tongue stroking my dick, this revived my stiffness and when she slipped her lips around the head I felt that uncontrollable spasm that heralded an eruption from my one eyed snake. I guess she swallowed it as there was no mess afterwards and as I tidied myself up she admitted her girlfriends had been discussing blow jobs in the week and she wanted to know what the fuss was all about for herself. I had to acknowledge I had enjoyed myself far more than I had done before, she said it was nice to see the pleasure on my face, but the day had been great messing about as two girls who could be lesbians. I decided it would be best to be away before her parents returned so left soon after and walked a sore footed walk back to my house.
That night I did not sleep in the nightie, things were getting a little out of hand and I wanted to try and regain some perspective, reality and composure into my very confusing life. This was not helped in the morning when my mother asked if I had had a good day with Kylie and I blushed at the memories, and then she went on to ask if I had tried on the new nightie she had bought for me as the one she had lent me was needing a wash. My inner voice screamed 'what......I now have my very own womans nightdress !!!!!!!! this has to stop'
Sure enough when I went back to my room in a bag on the bedside cabinet was a white floor sweeping silk nightdress, I could feel my resolve crumbling once more, how was I going to cope with all these confusing assualts on my previously held view that I was a normal straight boy.
I tried abstention, I cleaned every trace of make up and polish from my body, I put all the clothes in a bag and out of the way, college work came first as a form of distraction. It worked for a few days, but Kylie kept reliving certain parts of our gender swapping days as she got more excited by the soon to happen contest, and she was not going let me back out because I was feeling threatened as a man, her response was be positive, embrace it as a woman then. No help there then.
By the Wednesday my mother had noticed I was not wearing the heels around the house after college, she also had hung up the skirt and blouse in my wardrobe, washed the stained nightie which was now in my chest of drawers and laid out the new one on my bed, pretty much as she did with her own. She also had a talk with me about not backing out of the contest, reasons being, we would do well, Kylie would be disappointed, I would learn valuable lessons from it, but maybe most interesting, she had always wondered what a daughter would have been like. With pressure from both of them I was going to have to do it. Then on the Thursday I saw Kylie's mum who asked some question about how my preparations were going, which added to the pressure. This was followed by finding out who else was going to enter and realising that I could win the contest. Friday evening I repainted my nails and slept in my new nightwear. Saturday I had breakfast wearing it before getting dressed in all the girls clothing I had. There was a week until the contest and I was going to make sure I was ready for it.
Mother was pleased to see me in the skirt but did improve on my make up attempt. With nothing much planned I spent the day doing college work, Kylie came round in the evening and took me out to the pictures, nothing to wierd in that given the past few weeks, except she choose an action movie instead of the chick flicks she normally liked. Getting in the role she said. Later snogging the face of me making it clear she was excited by this relationship.
The contest was the next Saturday and I was getting focused on my preparations, I was getting good enough in the heels to almost run now, I had borrowed a skirt off mother to simulate the long bridesmaid dress and I was experimenting with make up so I knew what to do if needed.
Friday night and I hardly slept, nerves were taking over, this could go horribly wrong, the teasing, the humilation, then on the other side, possible failure, falling out with Kylie. Mother had a sleepless night as well if the time I heard her getting up was anything to go by. She brought me my breakfast in bed then told me of her plans for my day.
Get up.
Shower.
Check for hair growth, use the cream and shave.
Secure wig.
Secure breasts (new one on me)
Make up
Glue on long nails
Dress in casual
Then in the afternoon.
Restyle hair.
Redo make up.
Get into underwear.
Finally get into the dress.
Car to college hall
Win contest.
I was ok with everything, even when she glued the fake breasts to my chest and felt the wieght bouncing about in my bra, I was keeping in mind the ultimate goal. I was let off the heels around the house, saving my feet for later she said. I helped about the house trying to be occupied but all the time just wishing to get on with the contest. After lunch I changed into the corset and put on a pair of stockings, mother did not lace it up tight so my body could adjust to the restriction gradually she advised. Soon after that Kylie came round with the dress and I knew things were serious, she too was already getting into the role, which for her had meant a hair cut, now she had a short cut with a upstand fringe popular among the lads, when I said 'What have you done?' she replied 'You are supposed to say, it looks nice' but all I could think of was, what about after, her come back to that was, her legacy would be a boy cut, mine was my eyebrows. I had removed a few to tidy them up, but now we went went to my room and I had many more plucked from their home.
After this painful episode she started to talk about how much she was enjoying the mixed up genders we had experienced, we had been lesbians, gay men, the reversed straight as well as the regular straight. And she was not sure which combination she had found most interesting or satisfying. It was about this time she found out I was wearing the corset and stickings under my skirt and blouse which for some reason turned her on and when I heard mother shout up that she was going out to the shops for some food. Kylie became even more assertive. We were lay on my bed, her hand up my skirt and stimulating my growing erection, when she asked if I was enjoying being the girlfriend there was no denying it, she held the proof in her palm. I responded by undoing the fly on her trousers and slipping a long nailed finger inside, in the past I had massaged her breasts but these were firmly wrapped in bandages to make them flat. I am still not entirely sure how or why what happened next, but my skirt was around my waist and I felt her release my dick, I lay wiating to fell her lips on me, but after a few seconds nothing had happened and I looked to see her half naked and kneeling over me, her kissing resumed as she handled my stiff genital until I felt it touch what must have been her own genitals. Slowly she manouvred me into her hole, then with a few small wiggles of her hips I exploded into her. I was lay on my back but I still collapsed. We lay on the bed and cuddled, and I told her I loved her, she asked as a boy or a girl, I said I didn't mind, which at that moment was true. The sense of warmth between us lasted until we heard the front door open and suddenly realized we had better not let mother know what we had just done, so after a quick clean up I started to put on my contest make up ready for mum coming to style my hair.
In a way the contest was an anticlimax, yes the dress was lovely to wear, the corset was tighter but bearable, the shoes did hurt by the end of the evening. Mother made sure my hair was perfect, straight but not lank, fringe sweeping across my beautifully made up face. Kylie wore a tuxedo she had hired and looked as much a man as I looked a woman. The hall was packed with students and families, all three parents coming along to watch. The drama department provided the organisation and the student union the stage people. The compere was very good and ran through the different stages briskly so as to keep the show moving. We all had individual on stage interviews the questions for which we had already seen, I got a lovely round of appluase when I went on stage and gave corny beauty queen answers to the questions, yes my ambition is to ride horses and be a model etc, Kylie had to do the same along with all the other students who had put themselves up for this form of embarrassment. Those of us with partners had to do a waltz on stage, a few others had worked out a dance routine to a chart tune. Then we had to all line up and be questioned by some 'judges'. Finally there was a quiz game followed by the prize giving.
I should have recognised way back when this contest was first advertised that boys would take it as a joke mainly, I walked into the back stage and I was far too well prepared, some big lads just got undressed and draped an old dress of their mothers over their hairy bodies and wore their own shoes, my full on female look got an awful lot of comment, some not that complimentary. But I was still on cloud nine from earlier and though we did not win the quiz, nor the dancing (3 lads vaguely dressed as cheerleaders) won that, when it came to the best turned out man, woman and couple, we took the lot. I won a salon session, Kylie won a voucher for a mans clothing shop, and as a couple we won a meal at a nice restaurant.
Clearly we swapped prizes and enjoy the meal together. Life at college was difficult after that, many jokes were made at my expense if gender issues came up but mostly sexuality was not a problem as most had matured enough to recognise that we are not all the same. But mostly this tale for me is not about how I wore a dress for the first time, or whether I liked it or not, but about how I came to lose my virginity while pretending to be a girlfriend.
This is a different story to the womanless contest so don't get confused yet.
This story takes you through two kids growing up till events conspire to bring them together in a happy union.
Also for your amusement, but mostly for my friend, Naci Rema, this story has been rewritten with an american background.
I have know Terry since we were kids, we played in the same street, went to the same school got up to similar things when we were little. As we grew up I got good at sport while Terry just did not seem to grow, in fact out of the class we were in he was always the smallest boy, by the middle of senior school he was best described as a runt, the weakest smallest of the bunch. It was always his skill at imitating teachers that kept him out of trouble though, other boys would have been picked on, but he managed to stay on the right side of the bullies, and off course he had me as a friend who could stick up for him if no one knew the playground rules. The other difference between us was our home life, my parents might have started in the same area as Terry's family but they worked hard and we moved into better houses until we had a big house with separate bedrooms with en suites, it was luxury compared to Terry's house, he did have his own room, but that was because he was an only child, the house was tiny but his mother was always sick, she walked with a stick and looked pale most of the time. I suppose having to look after your mum and not being any good at sport lead to Terry getting teased, but he handled it well and clearly felt that to look after his mum was more important than being seen with the right people at school.
We even ended up going to the same college, I was going to do an engineering course, Terry was entered for A levels with a dream of university. The friendship was not as close because we only meet in the refractory but if we were there at the same time we would sit and chat. A very significant event occurred about February, while in a queue for our food I was stood reading a notice board with Terry and we both read the advert for a 'Womanless Beauty Contest', Neither of knew what one was so read about how this american idea was coming to the UK and the students union wanted to be one of the first to try it out on the British public. We were eating our cold pizza and cokes without saying much until I blurted out, 'You should have a go, reckon you could look like a girl.' He just said 'No way' but I ploughed on with ideas, I could get some clothes off my sister, his mum though frail, never looked anything but well dressed so would be able to help in making him look good, and there was prize money, something I knew Terry had little off as he did not have any time for a part time job like many of our friends. I kept on pressuring him though I was not sure quite why, in the end making him promise to tell his mother about the contest and see what she thought of it. He was never a strong willed lad and relented at this saying he would ask his mum what she thought.
I am not sure how long it was until we saw each other again but it was not immediately, and it was not me who brought the subject up but Terry. He had mentioned the contest to his mum and she was keen for him to have a go. I could tell this was not the answer he had wanted, but he had promised me to ask her and now he had promised her to let me know the outcome. Before the day was over he was sunk, we had been to the union office filled in an entry form, and I had paid the fee. Our little Terry was going to be in this pageant for definite now. The date was four weeks away just before the easter break, so we had time to prepare and plan for his performance.
My first job was to ask my sister if I could have some cast offs, when she asked what for, I was honest and she looked at me with a funny smirk on her face, but agreed, I swore they were not for me but for Terry who was out to win some cash. I left her room with several bags of clothes that had I no idea she had, and an offer to help with getting Terry to look like a girl if it was needed, I told her it might be an offer we take up, and left it at that. Next I took a trip to Terry's house to find him cleaning the kitchen, his mother was sitting in a chair watching TV. I was greeted as always with a smile but she never got up, just tucked her pill boxes out of sight. Terry came through with his yellow rubber gloves on looking strangely feminine already. I told them about the bags of clothes and saw in Terry's eyes a resigned look. I was invited to stop, but after a polite chat got up and left. Terry and his mum said they would sort through the bags and see what there was.
I would have loved to stop and be a fly on the wall as he tried on Maria's cast offs but I could not find a good excuse for stopping, so had to make do with an update when we meet at college two days later. In a hushed whisper he let me know they had been through everything, almost everything had been tried on, and he now had more girl clothes than boy stuff hanging in his wardrobe, I said that was excellent for some reason I never worked out. Then he produced a list of things he would need if he was to look anything like female. Shoes, my sisters nor his mothers were the right size, make up, his mum had some but not the right sort apparently, his mother did however have a wig and some fake breasts, cancer jumped to mind but I did not wish to pry in case I was right. I was getting carried away with the whole thing by this stage and offered to buy some shoes and ask Maria for make up and advice. Maybe this was going to hurt my pocket as much as it would hurt Terry's male ego, time would only tell.
That Saturday found me round at Terry's again, this time was very different, his mum answered the door with a big smile on her face, a peck on my cheek and I was ushered into the living room. I was sitting down wondering what to expect next when Mrs Jones called upstairs 'Come on Teresa it is only Brian, come on down and show him how good you look.' First thing I had not expected was that Terrance as his mum always called him would now be Teresa, the next was the person who stood at the doorway, head bowed looking very nervous, 'come on Teresa, let our guest see you' Terry stood in front of me and I was speechless, wearing a long silver top, a pair of tight shorts, shimmery tights was only the start, the chest on 'her' was just right, later I was told a C cup, the hair was a long mousy bob cut and when she looked up I could see the minimal make up had made a difference to the boyish face. From that moment on I knew Terry or Teresa would be a hit at the contest, but more than that I found the thought of Terry dressed like this unnervingly appealing, I had had girlfriends before, and I had looked at girls and rated them on an attractive scale, but Terry just looked fantastic. I wanted to say how good he looked but it seemed wrong for me to say something I would say to a girl when the words were meant for a boy. His mum had no such hang ups and enthused about her daughter who dutifully went of to make us all a drink, rather like he would have done anyway, but dressed as a girl he just seemed more in the role than before.
We chatted about what Teresa would need to go any further, and as I had told Terry before I would pay for anything extra that was needed, she patted my hand and thanked me for my support. She made plans for me and Terry to go shopping the next day for shoes, and if Maria did not have spare make up then we should buy some. I was wondering how two boys might get away with shopping for girls stuff, but that was something to be overcome if this idea was going to succeed. After a respectable time we left Mrs Jones on her own and I went upstairs to Terry's room, it was transformed, my sisters clothes were hung up all over the room and in front of a mirror was the few make up bottles he had used. I started of with 'wow, I thought it would just be wear a dress on the day'
Terry looked down at the floor. 'It is not that easy, she is really enjoying this project it has given her a bit of a perk up, but she says I need to get used to the ways of femininity if I am to make the most of this contest'
'Which means?' I asked
'I need to live as a girl as much as possible, immerse myself into the role so when I walk out on stage I think of myself as Teresa and not Terrance.'
'Sure?'
'She seems sure'
'If I was to say you already look great, would that be wrong?'
'guess not, do you think this all a bit pervy?'
Quickly I replied 'No, just fun isn't it' I was not going to admit to my earlier thoughts that I had felt attracted to him.
He changed the subject to college and who was going out with who, but after a while he asked which girls did I find attractive, soon he condensed it down to the ones who have nice legs, show off their chests and do their face and hair nice, a typical bloke he said. I asked what did he expect, he suggested I might look for friendship, a common bond, why were looks so important, because that is what we see first I said. But quickly followed it up with, 'with us though it is friendship, a common past and now a common purpose'
'And you are not just saying that because I have nice legs and a good pair up here' he was teasing me I knew, which was good as it meant he was relaxing in his new look.
'The nice tits do help, and when you wear a mini skirt I'll pass judgement on the legs, OK' for that comment I got a playful slap, not a hard boy strength impact more a gentle affectionate, don't tease me tap.
I looked in his eyes 'Teresa or Terry?'
'Mum says it should be Teresa when I am home or in a skirt'
'I think your mum is right Teresa, if you practice you will make an excellent womanless beauty'
Nothing much else happened that evening, but I had arranged to meet up in town at eleven on the Sunday to buy him some shoes. He was there looking nervous again but not nearly as pretty in his boy stuff.
His first words 'mum thinks I need some new underwear as well, if you can afford it' I did not answer so he continued 'just panties really and maybe a bra'
'I see'
'Hope you don't mind but the benefit cheque has not come this week'
'She said the undies will be easy, just say they are for a girlfriend'
'Easy? buying lingerie, I think not'
The knickers were surprisingly easy, we went into a big store, blushing a lot as we walked along the racks of soft pretty underwear, picked some in Terry's size then went to the till and mumbled something about them being for my girlfriend, which made the assistant say 'I hope she appreciates how embarrassed you are getting these things for her' I just went bright red and paid. Terry meanwhile had worked out how to try on shoes. We avioded proper shoe shops and went for the stores with rack upon rack of stock, he would slip his shoe off revealing a foot encased in girls tights and try on the shoe while I looked out for anyone watching. His mum had given him a good idea of what to look for and in the third shop we found them, black court shoes he had said, all I knew was that no boy would wear a shoe with a heel that high or with a bow across the top of the foot, but he seemed pleased to have found them so I blushed again as I went to pay for them. No comment this time from me or the assistant, just a no when she asked if I wanted their cleaning products. Luckily for make up Maria had said she would go out and buy what she called a starter kit. We parted after buying all we needed to get, then on Monday passed on the make up Maria had brought home. He was all set up now for his big day, I could almost see him shiver at the thought.
A week of college and not much talk of Teresa until Friday, when Terry tells me I was to go round on Saturday afternoon for tea. I did ask why but was told to just turn up and be polite. As if I could be anything but polite. I was greeted at door once more by Mrs Jones, a peck on the cheek and an invite into the house. This time Teresa was in the kitchen, I could see from the back she was wearing a shiny puff sleeved white blouse, a pink pleated tartan short skirt, tights and the new shoes, I was going to say something corny like 'You look good' but stopped myself when Teresa turned around, soft pink lips, big defined eyes and the blouse fitting tightly over the chest was the cause of my open mouthed gape. Mrs Jones then spoke up 'she does look beautiful, doesn't she' I was at a loss for words 'I tell her but she does not seem to believe me, you tell her Brian, I am sure she will trust you'
'Well er yes....you are very well....er... pretty'
She looked at the plates in her hands and softly said 'It's alright, I know I look like a girl, I just don't want to believe it'
'You had better believe it' I managed 'because you are fantastic'
Teresa then walked confidently in the new shoes across to the table and laid out the food for our meal.
Mrs Jones went out later with some neighbours leaving us in the house alone.
'Do you realize how hot you look?'
'Please don't tease me, I feel awkward enough as it is'
'No I mean it you do look very good even hot if you want the truth?'
'Not sure I do. Anyway mummy wants me to go out as Teresa and get used to being seen as a girl before the contest, boost my confidence she says'
'mummy, since when did you call your mum mummy?'
'Since this week, she says it sounds nicer in my girly vioce. I need someone to look out for me when I do this going out, will you help me?'
What else could I say 'Off course I will, when do you want to go out, and where do you want to go?'
Later that evening after it had gone dark we ventured outside, Teresa borrowed a hooded coat and we slipped out the door after I had made sure no one was about. A bus ride into town, a walk around deserted streets, a coke outside a Burger King and back on the bus. We were home for nine. Mrs Jones was so thrilled to hear about Teresa's first time out in the world and thanked me for being such a good friend. As I left Mrs Jones thanked me again, and I said anytime Teresa needs someone to take her out I would be only to willing to help out, Mrs Jones said that would be wonderful, Teresa I doubted was being quite so enthusiastic. So when asked if I was free Sunday evening, and I said I was, Teresa just quietly said, 'see you tomorrow then' with no warmth.
I arrived as requested the next evening, I took her for a walk around a nearby park, the hooded coat help hide her from possible meetings with people she knew. I was still cold so we found shelter and shrugged our coats around us.
'Mum is really liking me like this you know'
'I guessed as much'
'I have to be Teresa whenever I am in the house now'
'Thought so, you are very good on those heels'
'I know and she would like me to get some proper dress shoes as well'
'Oh'
'Do you mind me doing this?'
'Not in the least, happy to oblige a pretty girl'
'Stop teasing'
'but you are a pretty girl'
'Please this is so confusing' Teresa then turned to me and buried her head in my shoulder, I think she was crying, at least that was how it felt without seeing the tears. I put an arm around her shoulder and for the first time hugged her, it felt very much like having a girlfriend beside me, so I hugged her like one. In time she calmed down and wiped her eyes carefully so as not to smudge her eyes, 'Time to be going home' I said and took her hand in mine and lead her back to her home like that. Now I was feeling confused.
On the Monday we meet for lunch, Terry's face had changed, yesterday it looked right, but today his eyebrows looked rather too narrow and when I looked I could see a stud in each ear, his mum had done it with an ice cube to numb the needle. Ouch I thought. We found a quiet corner and I tried to say I was confused, but was rebuffed by the reply, 'you are confused, how the hell do you think I feel'
I told him I was mates with Terry, but Teresa made me feel like I should ask her out. Too which Terry asked that I never suggest that to his mother, she wanted him to try more of the female life than he was at that moment ready for. Then he floored me by asking if Maria has a ballgown or something fancy enough for the contest, I said I would ask but felt unsure if Maria would lend something like that.
To my surprise Maria did have a dress, and yes we could borrow it, it had been her prom dress and probably would never get worn again, so that was sorted. I was able to give Terry the 'good news' about the ball gown, he said thank you and followed it up with a request to stop at my house for the weekend. He explained how he was too well known around his house and was worried he might get noticed, whereas no one knew him on my estate so he could come and go as Teresa without question. I asked about his mum's care, he said she would be alright for one night and Mrs Phillips next door would look in on her if needed. So we made arrangements for Teresa to stop at my house the next weekend. My parents knew about the contest but were still a little skeptical about having Terry round looking like a girl. That was until thet meet Teresa and realised how good she looked. A few other things we had to do that weekend were, buy some shoes to go with the dress, this time Maria came with us and helped pick some blue sandals to match the dress, we also picked up cosmetics to go with the outfit and a small clutch bag for Teresa's bits. I was a little surprised to see how like a girl Terry was behaving in Maria's company, but he said the clothes influenced how he behaved, heels make him walk differently as well as the extra chest wieght, his long hair affects hands and face and the skirts make him careful about how he does many things like sitting and picking things off the floor. I could only say 'ow' as he linked my arm and thanked me for buying the new shoes. That evening Maria took Teresa into her room to give her a full try on of the outfit. What seemed like hours later they reappeared, Teresa was unrecognisable, Maria's blue dress fitted well, the bust was full, the line of the dress said sexy and when she turned around the lacing up the back revealed a hint of bum cleavage that looked so hot. I hardly noticed the spike heels, the redone make up, the long earrings, the big bracelets or the perfume. I just looked and realized I was not confused, I was in love, the confusing part was that Teresa was not a complete woman but for that moment it did not matter I just drank in what I saw and could worry about the details later.
After a short while of Maria and my mother fussing around Terry making sure the fit was fine and he was happy with the outfit, he was ushered out of the room and back to the spare bedroom he would be sleeping in that night. There he changed back into a tight fitting dress Maria had lent him. He came back looking so sexy I could feel myself stiffening in the trousers. This was going to cause trouble later I imagined.
After some tea, Maria invited us to go out with her and some of her friends to a pub nearby, as long as we stuck to soft drinks we would be fine. Terry seemed to accept this trip out like every other one, as good practice for the contest. Maria clearly enjoyed Terry's company and made him feel at ease, that was until she introduced him to her freinds as my girlfriend, later explaining how it was easier than telling the full tale. This left me an open door to behave like a boyfriend to the hot girl I was with, well I did have to maintain the cover story for onlookers. Surprisingly Terry never once rebuffed me, I sat close, held his hand, put an arm over his shoulder even put a hand on the exposed thigh. Like I said never once was I rebuffed, in fact I felt the opposite, when I put my arm over the shoulder he snuggled up to me, when holding hands it was not just me holding a limp hand but his fingers gripped mine as well. I even took a chance as we moved onto another pub and Maria was not about to get a quick kiss on the lips, no instant passion but I was not rejected or screamed at, I was beginning to consider the possibility that maybe he likes being my girl as much as like him being my girl.
We got home quite late and just said our good nights to Maria who was chatting with her boyfriend at the door. I took Teresa to the spare bedroom and asked if there was anything required, then before I could stop myself I kissed my friend on the lips, proper full on kiss, it lasted only seconds before I pulled away 'sorry' I said 'but you look so good and with us playing a couple, look I am sorry I shouldn't have taken advantage' he said nothing for a minute fiddling with a bracelet he was wearing, then apologised for leading me on and suggested I would rather he stopped asking for my help. I just took him in my arms and gave him a cuddle then kissed him again, this time teasing his nice tasting lips apart with my tongue. This time I did not apologise when we stopped, instead I told him he could lead me on anytime he wished.
The Sunday I took my girlfriend for a walk in the woods suggesting that maybe when the contest is over Teresa would like to come and stop another time, he made it clear that the whole Teresa thing was to win the contest, I suggested his mother liked having a daughter, I liked my hot girlfriend and even he seemed to be enjoying being a she. His reply was to say it was getting all mixed up, he was a boy but everyone seems to like Teresa more than Terry, I just said 'give in and be my Teresa for today at any rate' and took the hand that was near me, leading my girlfriend back home and to an empty house.
We had a bite to eat along with some wine my parents had left out, then when I invited Teresa to sit beside me on the settee she did so, leaning into me and tucking her feet under her arse.
'You know if you let me I would love to go out with you' I ventured
'I know' came the reply
'So when can I take you out properly next time?'
'Please don't rush me, I am just seeing what it is like to be a girl, and next week I have the contest unless you had forgotten'
'Ok, so that is not a get lost'
'No not a get lost, now give me a cuddle, shut up and watch the film'
By the time my mother had packed Teresa and her belongings into the car I was sure I was going to see much more of this girl. With Terry gone my father had a quiet word with me pointing out that Teresa was a boy, and a boy they all knew well, yes he did look convincing as a girl, but he was still born with all the boy bits and none of the girl stuff. I said I knew all that, he said that was good, he was just wanting to make it clear that what I seemed to be doing might be thought of as gay, I nodded and asked if he had a problem with that, he said not and left it at that.
Meeting Terry at college was odd, he still had the narrower eyebrows and he even walked a little differently now, but I had no desire to touch him like I had at the weekend, which I think we were both grateful for. In fact we hardly spoke of Teresa other than to plan our activities for the contest preparations. Most of the organising was out of my hands, Mrs Jones, my mother and Maria had been in touch with each other and Terry's life was not his own come Saturday.
First off Terry would be prepared by his mum, I was told complete hair removal, prosthetic breasts would be glued on, his wig sewn into his own hair. Then in the afternoon my mother would go and pick him up and bring him round to ours, where Maria would make him up, style his hair and get him dressed for the evenings performance. All I could do was get in the way, so I made sure I was about but not near if you know what I mean.
The contestants were asked to be at the hall for seven, Teresa was ready for six and eating a light snack while wearing a dressing gown borrowed of my mum. At six thirty I went with my father to pick up Mrs Jones, she looked fantastic. It must have taken a huge effort on her part to look so good but there was no way she would miss this, nor be upstaged by a son, though I reckoned she would be, and easily. Mum and Maria would take Teresa and the dress to the hall and make any final adjustment required. At sometime in the past weeks a conversation was had about how we would approach this contest, would Terry be a drag queen, a hairy lad with a poorly fitting dress draped over him or go for the full thing, I was not sure who had made the chioce possibly his mum, but as we stood around we could see all sorts of ways in which the contest had been interpreted. There were some shocking sights, big lads with big dresses and bright red lipstick, some drag queens looking like Marge Simpson, and a few who had had the nerve to hide their masculinity beneath a feminine disguise, and though I was biased, our Teresa was the best.
The contest started with twelve contestants walking onto the stage, in the middle was Teresa looking nervous or coy depending on how you viewed him. They all had an interview with the compere, they had some interesting stories as to why they had entered and why they wanted to win, Terry just told the truth that his mum was unwell and the money would be a nice boost for them and added that I had been his sponsor and said thank you publicly. Next was the catwalk parade, off course we won that what with all that heel walking at home he was a natural in the stilts. Last a panel of 'judges' asked random questions such as one who asked Teresa 'did he prefer high st clothes or boutique?' the answer 'niether, borrowed is cheaper'. Then while there was some heated debate over who was the winner a DJ was brought on stage and the dance music started. The contestants went back stage and then came into the main hall, none were allowed to change and had to mingle in their finery. I had to say Teresa mingled very well, all that taking her out was paying off, she eventually made it to our little group and thanked us all for coming, kissing the women then giving the men a peck as well. We all said ours was the winner, and we were right. Half an hour later the contestants were called back on stage, and the judges verdict announced. Terry Jones had won first prize, this was £500 plus a make over at a salon in town, plus a gift voucher from a mens boutique. The smile was brilliant and lit up the room, for someone who had never won anything to come away with such a good prize was great.
The evening continued, the DJ played his tunes into the night, Teresa was able to dance with who ever he wanted, some girls but also some men asked for a dance with the winner. Mrs Jones stayed to see him win then asked my father to run her home. I managed a couple of dances with my girlfriend, copying what some others had done, placing a hand on the small of his back and letting a finger carress that cleavage, and I was not told to move it. I got the imoression he was enjoying the attention but was never sure. Maria had the same number of dances as me, but who was counting I was just enjoying seeing my beauty being flattered by so many people.
Before the lights were turned on and everyone told to leave, we had gone. Teresa came back to ours for the night, and as we sat up reminsing over how well the contest had gone for our girl, I felt myself once more wanting to make Teresa a more permanent part of my life. After a while the women went to clean up for bed, Teresa obviously went with them. While I sat downstairs with my dad he told me how good looking Teresa was and he was not shocked that I found such a girl attractive. What did shock me was that all three of them came back downstairs for a nightcap, I had seen mum and Maria do this in the past, but to see Teresa come in with hair and tits still in place under a short satin nightie and longer wrap, then curl up beside me on the settee. Now that was a shock. Maria left first, then mum and dad reminding me to turn off the lights when I went up to bed. After the footsteps had died on the stairs and doors had closed, I turned to face Teresa 'I just can't believe what I have seen tonight, in fact what I am still seeing' this got a warm smile. 'Just for tonight will you be my girlfriend' I got a nod and my girl moved along to sit beside me, 'Everyone loves you, you know' I then took that beautiful head in my hands and brought it towards my mine and kissed those lips once more, this time I felt a tongue searching into my mouth and before long I was massaging what I knew to be fake but very realistic feeling breasts. The satin fabric felt very erotic and the smooth skin was luxurious, but when I realized there were no panties and no erection, I did ask what was going on. The answer was for Teresa to lift the hem and reveal a triangle of hair and no dick.Somehow Maria had fastened it back between his legs using surgical tape, when I pointed out he had to sit like a girl to pee, he smiled and told me that was how he thought I liked it, I just said it was best if only one us has a dick, he smiled and put a hand on my crotch. Now, until then no one had put a hand on my cock and right then I was enjoying the sensations. A few careful strokes and I erupted into my pants and the moment passed.
'Is that what you wanted?' my girl asked
'That was more than I expected, thank you'
'My pleasure, you helped me me win today, think of it as payment'
'Some payment'
'Indeed' as my beauty got up and walked away wiggling the satin covered arse.
I eventually calmed down and slept after that wonderful evening. An unexpected surprise was to find that Teresa was still with us in the morning. I had not realized, but Teresa had come the day before, and had brought no Terry stuff so unless some one went to get his unattractive drab gear from his home, he would have to look like a girl, and I was not rushing to sort that one out.
Later in the morning my mum drove Teresa back to his house, we stopped a little while to make sure Mrs Jones was ok after her tiring day, and go over the high points once again. All too soon I was leaving my beauty and going home to catch up on college work, such an anticlimax.
I think it was mid week before I saw Terry next, I accused him of avoiding me, he said his mum had not been well so had skipped some classes. He told me how his mum had been thrilled to be given the salon voucher, and had refused to accept the cash he had won, but I guessed he would spend it on her over time, better food, little treats when she was down, that sort of thing. As for the clothing voucher he wanted me to have it which was nice but I refused saying I can afford anything with my job and allowance. He did not know what to do, so I made arrangements to meet him and we would take a look and see if there was anything either of us liked, thinking I get something inexpensive and we spend most of it on him. Nice compromise I thought.
We turned up at the boutique and a very effeminate man served us after we had browsed a little. Now remember Terry still has the narrow eye brows, his nails are neat and he has not lost that walk he developed while wearing heels all those weeks. The assistant must have picked up on this and showed us some tight white vest tops, fashion jeans and stylish shoes, effusing over Terry as he tried things on. At last we left with a white T shirt that was so tight you could see hairs on his chest, if he had any, a check shirt but not one I would choose, the assistant had picked one with a pink thread in the check, but the eye wateringly tight jeans was the most outrageous item in my eyes, how he got in them I have no idea but they made him look so slim it was like he had leggings on again, so I liked them. For my part I picked a T shirt, loose and grey so as to keep away from any gay stereotypes that Terry and the assistant seemed to be happy entertaining. When we had made our choices the assistant asked if Terry would like to wear his straight away, within minutes I was walking out of the shop with a person I could tell was somewhere between girl and boy but not sure if either of us liked to look or understood what it meant or how it looked to others.
One person who liked the outfit was his mum, she maybe said the wrong thing when she called the shirt 'pretty'. She was clearly happy as she had been for her salon visit as well that day and looked so much better for the pampering she must have received.
Life for a couple of weeks went back to my old routines, college, working, family, all the normal teenager things. Terry was still around, we would meet on occasion, and on ocassion I would tease him that I was missing Teresa, a feeling only hieghtened when I saw him in the tight jeans and pink shirt. He always quietly told me Teresa was gone and I should find myself a real girlfriend. Luckily though Terry reminded me of Teresa I did not fancy Terry, in my mind to have kissed Terry would be gay, yet kissing Teresa was fine, I know it is confused but that was how my mind was working then. Anyway after four weeks I noticed that his nails were still very neatly filed round which made me look elsewhere, his arms were still hairless and I could swear his eyebrows were not growing back, I would have had a bet on them still being plucked in fact. My problem was I could think of no way to prove my suspicions, nor did I have any reason for him to be doing these things, so confident in my own attractiveness I felt sure that if he wanted to be a girl he would want to include me in that part of his life. The truth came out by accident really, I had expected Terry in college on a Thursday, we had lunch at the same time and always ate together, this Thursday however he was missing, so being a good friend I wanted to know if he was ok, he was one of the few without a mobile, so after my classes I went home via Terry's house, this was when everything I had suspected fell into place. I was welcomed at the door by Mrs Jones, she was not looking at all well, but had enough strength to welcome me in. Then I got my shock, Mrs Jones called out 'Teresa, Brian is here to see you' then turned to me 'She is just making the tea for us, I am not having a good day today I'm afriad and she stopped home to look after me. I told her to go she can't afford to miss too much college it will harm the grades, but she ignores me'. In the kitchen door was a stunned looking girl, Teresa was clearly shocked to see me, but it was definitely Teresa and not Terry, though I recognised the tight jeans; the flowery top, heels and long hair made sure he looked like a girl.
'You weren't at college, thought something might be wrong' I managed to stammer out.
'Come in, sit down' said Mrs Jones
Teresa just stood there looking horrified now.
'Come in dear' his mum invited.
'Mum was not too good this morning so I thought I was more use here than at college, did anyone notice?'
'I don't think so, maybe I had better be going if you are cooking.' I got up to leave and walked to the door.
'See your friend to the door dear' Mrs Jones said
We walked to the door then I turned to look at my stricken friend 'don't tell anyone'
'Well no'
'I dress like this to please mum'
I said something inane like 'fine'
'Please.... our secret' she implored
But my mind had realised I could have Teresa back 'Our secret............just you me and your mum..... our secret, but would you dress like this to please me?'
She was looking at the floor, 'Brian please I am not a real girl, this is all pretend, you need a proper girlfriend'
'No I don't, not when I can have you, and don't tell me what I need, my girlfriend is you and that is all either of us need to know'
'Brian, please it was only a bit of fun I meant nothing by what I did'
'I think you did, you did not have to kiss me, you did not need to play such a good girlfriend, you certainly did not need to wank me'
Tears were appearing in her eyes.
I put a hand on her shoulder as a comfort, 'Sorry I did not mean to upset you, I just want Teresa back in my life'
She opened the front door 'Please go, I will see you at college tomorrow'
I went to give her a kiss but she pulled away, so I left with all sorts of thigs running through my mind and imagination. Condensed down to, Teresa is still about, how can I get her to go out with me?
The next day at college I made sure I found Terry, he was in his jeans and pink shirt, plus there was a faint smell of flowers about him, perfume?
'Your mother better today?' I wanted to bulldoze in but decided to try a friendlier approach.
'Yes thanks, I did not want you to find me like that, it pleases mum to have me dress up for some reason'
'I did not mean to embarrass you, I genuinely was just concerned that you were off again'
'thanks'
'Can't deny I liked what I found though'
'I knew you would, that was why I did not want you to find out'
'But now I have, when can I see Teresa again?'
'Please it is just to please mum'
'What about pleasing me?'
'Please don't pressure me, I had hoped the contest weekend would be the end' his strength was leaving him I could tell.
'But it wasn't, and Teresa is still looking good, so why not embrace it'
'And make your dreams come true'
'Well that as well'
'And if I say no' I could almost see his resolve crumbling before me, so I pressed on hoping to get what I wanted.
'If you say no, I will just keep on calling round at your house whenever I don't see you at college, because I am guessing you will be home being Teresa'
'And if I come to college?'
'Well you will feel guilty leaving your mum' I knew that was harsh but I might only get this one chance 'and you will see me and know that I know your secret and want to keep on my good side'
'Please don't do this' he was beginning to tear up.
I continued 'and keeping on my good side means being my girlfriend'.There I had said it, if he would not be my girlfriend then I had implied enough to make him know his secret was not safe.
There was no reply, I never thought myself a hard man, but Terry was crushed, I felt I had destroyed the lad I knew but I did not want Terry I wanted Teresa. 'see you tomorrow?'
I swear he swallowed a sob, 'I don't have a choice do I?'
'Not really I suppose, how about I call you Terri, spelt with an i instead of a y'
'Whatever'
'Bye Terri'
He made every effort to see me every day and be nice to me after that, but the friendship had changed, no longer mates, rather I was in charge and he would do my bidding. I know this had made me into a bit of a bully. At first I enjoying the hold I had over my friend, when I saw him the next day he did not smell of anything besides clean, so I commented how nice he had smelt the day before, he blushed and I asked if he would wear it for me the next day. I was not sure he would, but the next lunch I spent with him he was smelling sweet. When I asked what it was he told me it was the rose scented soaps and talc he was using up because it had reacted with his mothers skin. I told him that when it runs out he should let me buy him some more rather than going back to his old brand. Rather meekly he agreed and gave me the name of it and asked for some body wash. The following Monday I gave him a bag with the bottle in it. He took it and said thank you, but to me it had more significance, he was doing what I wanted, and I was providing for him and his feminity.
I had a plan to not rush him as that might get a bad reaction, hecould walk away and call my bluff, so I left it at the soap for a week or two, but always complimenting him on how he looked especially if it was vaguely feminine. Then he missed a day, so I found time to call at his house on my way home. The door opened with Terri hiding behind it hoping no one outside would see him.
'Everything ok?' I said as I walked in.
'Mum is not good at all'
'Sorry to hear that'
Then from the living room 'Who is it dear?'
'Only Brian'
'Come in Brian, you well?'
'yes thanks, Teresa was not at college today, I was worried'
'That's sweet of you, but I am afriad it is me that is not good, a ball and chain to my child I am'
Terri stepped to her side 'I don't mind at all, you know that'
I asked if there was anything I could do to help and promised to call whenever I could.
Terri showed me to the door, 'That top suits you' it was a fitted blouse that pulled across the breasts, and to me looked dead sexy. 'Do I get a kiss of my girl?' Terri made no attempt to kiss me so I put a hand under her chin and lifted it up until I could kiss those pink lips that tasted of lipstick. 'See you tomorrow?'
'If mum is better'
I kissed her again and left, I had got a kiss off her when I had thought my chances of even seeing her again had died a few weeks before, I was elated. Now invigorated with that sexual contact I knew I would want more. Even if the relationship was very one sided.
That weekend I bought a gift for my girl. The ear piercings had healed up well but he only had plain studs to wear so I bought him some more studs with a red stone in them. I gave them to him on the Monday.
'Should I be grateful?' he said before even opening the box.
'A thank you would be nice'
'Thank you' said without emotion.
'I thought they would make a nice change to those plain ones you always wear'
'I can hardly wear mother's to college can I'
I gave him a checky grin 'Why not..........only teasing. But these are nice and descrete'
'But a girl's'
'Well that as well, which we both know is why I got them for you'
'And you want me to wear them'
'Off course, be nice with your red roll neck jumper'
He let out a big sigh and asked me how Maria was now she had left home. He was changing the subject but I had made my point so went with it.
Tuesday under a hoodie I could see the red top and the red studs, I pulled the hood back and took a look, as a tease I said 'Maybe I should have got a larger stud'
Immediately he replied 'No these are fine, just lovely'
'So you wont mind wearing them all the time'
He nearly said something but backed down. The next day I was pleased to see the studs were still in their place, making his ears pretty.
My next move was to visit Terri at home of a weekend. I could not think of an excuse, but then I figured who needs an excuse to see their girlfriend, so I just turned up on Saturday about seven. Terri looked shocked when she opened the door, I was quickly invited in and went through the usual polite how are yous with Mrs Jones. I was sitting watching some TV with her when she said 'Those studs you bought were nice, never has them out of her ears now she likes them that much' Terri was sat opposite and just mouthed like a fish.
'Just a gift so she doesn't feel neglected'
'Very thoughtful of you. Now if you don't mind I am tired so I shall get myself off to bed'
It was only eight but accepted that she was ill and needed rest, Terri went with her to help with whatever she needed, so I amused myself channel hoping until I found a fashion show which I thought might be a good tease for when Terri returned. I also moved myself to the couch.
Terri came back about fifteen minutes later, I took in the picture of her in a straight denim skirt, white shiny blouse and the party heels. She was still my best ever girlfriend, I patted the seat beside me to invite her to sit by me. Then with my arm around her shoulders we watched the fashion show, followed by a drama. I thought it made a for a nice night in with my girlfriend, and whether she was cuddling up to me to get on my good side or because she wanted too I did not fathom, but I for one was content with the situation.
I visited every Saturday evening for the next three weeks, the same pattern followed, polite chat, Mrs Jones says she is tired, I get to cuddle Terri. By the third week we had moved on from a good bye kiss at the door to kissing in the living room, I was feeling Terri was getting happier at the prospect of being my girl, what happened next took me by surprise. As usual I called round on the Saturday, but this time when Mrs Jones sent Terri to make her a hot drink she conspiratorially leaned towards me.
'Brian, you seem to be having a softening effect on Teresa' I looked at her questioningly, 'the studs, the shampoo and wash, coming round to see us, I might be sick but I still see and hear what is going on'
'Oh' I said a little embarrased.
'I want to ask you a favour, sometimes I am finding the toilet seat up. Now that dress she wore to the contest was so low cut at the back she could not have been wearing knickers, am I right?' she did not wait for an answer 'now the floppy bit inbetween her legs must have been tucked away somewhere,. Now what I am asking you is, can you persuade her to do it all the time, it is not nice thinkig of her standing up to relieve herself like a boy'
'Well I am not sure what I can do, maybe have a word'
'If you would' as she finished Terri walked in with a tea for Mrs Jones, one of the beers I had brought and a lemonade for herself. The subject was dropped and we discussed some item on the TV.
Later on that evening I was cuddling Terri as usual waiting for a moment to 'have a word'. In the end I just said 'Your mum doesn't like you standing up to pee'
This got a swift reaction, 'you have been talking with mummy about me'
Damage limitation 'No not like you are thinking, she likes the softer you, is grateful for all you do for her, really likes having her daughter around but.......you are leaving the toilet seat up'
Things were calming down 'That's easy, I shall put it down in future if it means that much to her.'
This could be awkward I thought 'Well yes if only it were that simple, you see that would mean you still stood to pee'
'Fine I shall not splash it in the water if that is the problem'
'And what if you forget, no, maybe if you taped it up like for the contest, then you would always sit and you would never forget. Problem solved'
'You are serious aren't you'
Just for fun I added 'and it gives you a nice flat crotch as well'
'If I say no'
'Please let's not go down that one, just do it to please your mum'
She turned away from me, 'You want another beer?'
'Thanks' that was the end of the discussion I had done my best.
Monday I was not sure what to expect, Terri had been quite cold after the talk of toilet etiquete. So imagine how I felt when I saw Terri walking towards me, tight jeans displaying everything that was happening beneath and there was no sign of male type front bump, just a flat V creasing into the tops of his legs.
'Have you told your mum'
'No I just walked about in panties so she could see I had complied to your wishes'
'She does love you'
'I know, but she does not make it easy for me'
'Maybe not but I apprecaite your efforts as well'
Later that week I bought him another gift from the boutique where we got the jeans. I found the same assistant, he was disappionted I was on my own, but when I said I wanted something for my friend he knew who I meant. With his help I bought a pair of white jeans just as tight as the others and promised to come back soon. On the Saturday I took them with me, Mrs Jones was more thrilled by the gift than Terri, but who cared, with two pairs of tight jeans he could display his flat front all the time.
The end of year exams were upon us and I was doing quite well, but I could tell Terri was not able to put in the work, I tried to reassure with cliches like, they seem worse than they are. It never crossed my mind I might be the cause of his poor results, I assumed it to be the fact he was caring for his mother and not anything resulting from him doing the womanless contest.
Things progressed on the Saturday night front quite well though, I was no longer having to prompt behaviour in Terri, she would just sit with me, even in her mother's presence, give me kisses without being asked for them and make me feel like the man in the relationship. All of this was nice but I still wanted more. The next stage came when I passed my driving test and got to borrow my mother's car, this meant I could visit Terri more often, and after a few attempts got her to leave the house in a skirt. The first time I took Terri out we compromised, jeans, hoodie jacket, flat shoes, but this was on the condition that one item was exchanged for something more overtly female the next week. So we got a flowery top, then low heeled shoes, then she borrowed a pair of her mother's baggy linen trousers, before finally stepping out in a skirt. At last I had Terri back to where we had been before the contest, I had my pretty girlfriend linking my arm as we went into a bar to get cokes, making me proud.
The next event was unaviodable really, it was bound to happen, the neighbours found out. One happened to call unexpected and without knocking let herself in shouting 'only me' and before Terri could hide upstairs she had been spotted. At first the woman apparently did not recognise who the girl was, but then when she did Mrs Jones told her some story about how Terri is transgendered and is living as a girl part time to find out if the female life is the one for him/her. And the neighbour bought it, apparently saying 'as if you havn't enough to cope with'. But the secret was out and I had no power over Terri to call the bluff, for some reason it did not change our relationship. It even lowered her resistance to being seen by the neighbours, with an attitude of what the heck, let them have an eyeful. Within weeks I was walking out their front door with a girl displaying her womanly chest, and long legs.
It had taken a few months but we were getting somewhere that I wanted to be, even if Terri was not completely in favour of all the changes.
That summer was great, the neighbours finding out Terri was 'transgendered', the freedom to take her out, long warm evenings and the oppurtunity to buy her new clothes made it in part special. What made it great was my family. First Maria cornered me into admitting that Terri was out once more after I had been seen with a girl by some of her friends who had remembered us at the pub all those months ago. Next was that I did not go on the family holiday but was left at home with Maria, who was more relaxed about my comings and goings than my parents. This freedom allowed me to manipulate some interesting events in Terri's life.
First was turning up early when Mrs Jones invited me for tea, then while Terri was cooking and her mum was listening to the radio, I went upstairs to use the toilet with the main purpose of getting a look at Terri's room, somewhere I had not been since the contest and I suspected to be very different. I was right, the place was more like Maria's bedroom with make up and clothes everywhere and interestingly I could not see anything of Terry's, all the boy college stuff was out of sight. It pleased me to see such a room and went back to my hosts satisfied Terri was living full time as a girl. That same day I drank too many beers before I realised I should not be driving, I could catch buses and walk as I used to do, giving me another excuse to call when I picked the car up sober. Or on Mrs Jones insistence I stop the night, and as I would be home alone why not. So I stopped the night, nothing happened, as I slept on the couch downstairs, but I did get the wonderful sight of Terri in the kitchen wearing a long satin nightie as she made her mother's breakfast. The most telling part was that the tits were still in place and the hair firmly fixed, even at night Terri was a girl. When she came back down and asked me what I wanted, I replied 'You'
'Don't be checky' she said as she walked towards me with a teapot.
I stroked the satin covered arse. 'I would love to have you right now' then things happened unexpectedly, she lent towards me and kissed my lips, next she sat on my lap an arm round my neck. 'Like this?'
There must have been something about nightwear because she was more commited to the kissing than I could remember. After what seemed like an age we broke, 'Hows about we go back to mine when your mum is sorted.' To my surprise I got an enthusiastic 'yes'. Which an hour later was converted into having a very pretty Terri sat beside me as we pulled into the drive. Maria seemed to be out as well so we had the house to ourselves.
'You want me, so here I am'
Now I had her, I was unsure what to do, I started with kissing, then fumbling inside her clothes. In the end she undid her blouse and lowered her skirt, she now stood in just bra, knickers and heels, what a sight. 'Could I make love to you?'
'Do you know how?'
'We could find out' and I took her hand and led her to my room.
I had read about sex and listened to lads bravado, but when it comes down to it, getting a stiff penis into a tight hole is not easy, but there was some jelly in the bathroom and with patience I found myself inside Terri's arse and exploding before much else happened. Goodness knows what had inspired her, but as I lay there recovering she cleaned my prick then gave me a blow job. Wow, what a turn around.
'Did my man like that?'
'How can I say no. What brought that on?'
'I am not sure, but seeing you in your boxers this morning, I just thought it would make you happy'
'Well that was right, you have made me happy'
'I also got to be your first, which must mean something'
'Yes that I love you'
'Don't get carried away just because you have had sex with me'
'Not carried away, ever since the contest I have loved you'
'Why didn't you say that instead of the bullying'
'Couldn't be sure you would accept me'
Our peace was broken by the front door opening and Maria coming home.
'My clothes are downstairs'
'OMG, stop here'
I left my love on my bed and dressed quickly before going to the stairs.
'Hi brother, is it safe to come up?' she was carrying the evidence on her finger tips. I ran downstairs took them off her and returned to my room. 'must be good to be at this early in the day' I heard her say as I shut my door.
I was flustered and threw the clothes on the bed, but she was the one teasing me now. 'What's the rush, do you not want me anymore?' and gave a hurt expression.
'Come on get dressed and I shall run you home'
She did get dressed but waiting in the kitchen was Maria, we did not strictly have to go that way, but Terri made a point of going in to say hello. Maria looked unfazed by seeing Terri again and in the knowledge that we must have up to something. At the same time Terri was casually sitting down for a chat with her, I think to make me squirm, and she succeeded.
Terri did not leave till late afternoon, by which time her and Maria had discussed everything about the reinvention of Terri and even where things might go from there. For the first time I felt that Terri might have the upper hand in the relationship and with Maria in on it my life could be difficult.
Maria did indeed enjoy teasing me about the relationship, but not because it was Terri who we both knew was not a fully developed female, but because I had a girlfriend and had been so secretive about it. Pretty much normal behaviour for syblings I reckon. Terri however was now able to manipulate me, like the day she came round, satisfied my carnal lustings, then easily got me to take her shopping for a new sun dress, not that I minded, she looked lovely in the white cotton dress which exposed about as much skin as was decent for a public place.
By the time my parents had returned from their holiday I think we had had sex five times, plus several blow jobs. Looking back we were not very good but at the time we were enjoying ourselves, I would do some research on the internet with the hope of putting what I had learnt into practice later on. On that fifth session Terri was on her back with her legs up high giving me a clear access to her hole, I was able to control myself better by then and pumped away for what seemed like an age, then to my delight she tensed, arched her back and came, her little restricted dick dribbling cum over my shaft below it. I had made her come like a woman, I was so pleased with myself and from the expression on her face I could tell she was sated as well. The equilibrium swung back towards me, sex was not all about my pleasure after that, she too was taking as well.
There were not many oppurtunities left during the summer holidays after my parents came home, a couple of daytime encounters but my summer job got in the way as much as the house having family members in it and I knew once we were back at college things would change, and they did. We had one last night out before college, Terri was wearing the softest dress you ever saw, it was long but ever so sexy, the 4" heels and bare shoulders made sure of that, and besides some panties the dress offered no barrier as it lifted up so easily allowing me access to her hole.
Unfortunately by the next Monday Terri was obscured by the return of Terry so he could attend classes without much hassle. Gone was the long hair, gone too were the tits, the heels and make up were missing as well. I know I could not push her to dress in a skirt to attend classes and had to accept that while there I would have to make do with my girlfriend looking rather masculine in jeans and shirts. Even if those jeans required the wearing of knickers to aviod bulky underwear lines, and the shirts had a definite feminine edge to them. He would also wear the red studs all the time, and when I bought some larger pink ones he resisted because of the impact it might have among college friends, but he gave in and wore them.
Mrs Jones was aware that I was wanting Terri to become as much a woman as I think she wanted her to be, the toilet seat incident and the transgender story for me bore out this understanding I had of her, but I was not quite so fully aware of what she was doing to her child. Frial and sick she might have been, but febble minded she was not. It was her who made space for us to spend time together early on, it was her who would encourage me to take her out, it was her who had kept her dressing after the initial contest had opened up Terry to looking so good. But what I discovered that autumn took me aback. Mrs Jones was going to need to spend a few days in hospital, there was nothing unusual in this, what was different was that before she went in we had one of our quiet words, where we would tell each other what we hoped Terri might do next in her move toward womanhood. This time she quite frankly told me that if I was going to be calling round while she was away and, as she put it 'having fun together' then I could make sure Terri took her medication. She went on to explain how at least once a day she made a drink for Terri, and dissolved the tablet in the hot coffee. I asked why not let her take it as a pill, she said it was better Terri did not know she was taking it for her own good, if she knew it might disturb her. Which I took to mean the pills were some sort of nerve calming pescription.
A week later I was enjoying the freedom of Terri's house with just the two of there, and made the effort to get to the kitchen after we had had sex and before I went home, so I could make a coffee which included the pill. Mrs Jones was having series of treatments that meant she was in hospital for a couple of days for several weeks, so I did my best to make sure Terri got her pills as well as getting my end away. It was not until about the fourth week I noted the name on the pill container and looked it up on the internet. Crafty Mrs Jones was giving her child female hormones, possibly ones perscribed for her I imagined, but as I read about the pills I recognised things in Terri that until then had not seemed odd, Terry's vioce had never broken, I was shaving every day, he had no shadow of a beard on his chin, other things less objective like he could cry at the slight things on ocassion, and his personality seemed much softer somehow, all of which I put down to the hormones. Armed with this information I made sure Terri got her daily dosage and when I had a chat with Mrs Jones about them I was able to say with confidence from my research that Terri's body could stand a higher dose, she asked me how I knew and if I was sure, but reassured she told me she had plenty of spare and she would ask the doctor if she could have more supposedly for herself. By November and the last of her treatments Terri was taking three times as much hormone, her moods were less predictable and at times weepy, but her mum said she had been like that as a teenager, there was no need to cut back on the pills. It was when I asked what she would like for Christmas I found out other things had been affected by the hormones, she asked for some new jeans because the old ones were getting tight around the hips, and when I took a descrete but careful look her arse was indeed more rounded. Buying new jeans took him into wearing woman's cut trousersbecause the men's were to loose at the waist and legs if they fitted the hips, I finally bought a pair of hipster jeans which could almost be male if you did not look closely. Something that I noticed was the chest, at college some days my friend would wear a fitted t-shirt under an open shirt and his shape was changing very slowly. At first I asked if he was working out a little, but when he asked why, I pointed to his developing pectorals and touched one, which made him flinch, 'tender'I asked 'very' he replied. Mrs Jones was delighted when I told her about these observations and I am sure increased the dosage yet more.
By Cristmas I had come clean with my parents, at first they were skeptical about such a relationship, they had seen Teresa early on, and was unsure if I was being sensible getting so involved with someone who clearly has mental issues as well as a sick mother to care for. I hopefully reassured them that I was handling the situation well and that Terri was even better now than at the contest. This did mean I could invite Terri to visit over the christmas break, in fact after mum had meet Terri she invited her and her mother over for a meal on boxing day which made Mrs Jones day I think.
As Terri got better known, so her freedom to be feminine grew, but for college she maintained a boyish look, on reflection it is hard to think why, most of those who had known Terry as a kid now knew and believed the story put out by his mother about him being transgendered, and when it came down to it he was suffering in the same way that many carer children do, they fail acedemically because they spend too much time caring and not enough studying. Thankfully that was the college take on the situation which had no real grip on what Mrs Jones and myself were doing to our girl in the making.
By easter if Terri came to college wearing something tight the large nipples of christmas had grown into small mounds, and much to our delight were great fun to play with when having a good time pushing my dick into her hole, or even just cuddling on the settee.
By summer I knew I had done well enough on my course to get an apprenticeship and start earning proper money. For Terri it was completely different, she failed all but one exam, her mother was getting worse and for her the changing body shape had got too distinctive especially around the chest, so much so that she had bought bras to support the growing breasts which for her meant she could not possibly go back for another year at college and hopefully do better in a years time. I personally loved the new shape and even encouraged her to stop wearing the false ones, knowing that a disappionting reduction in visible size would be more than made up for in the reality of natural fleshy tits. Without much effort Terri never went back to college after the results, she just stayed at home and looked after her mother.
Ther was nothing much to report for a while after that, her chest developed to a size that nearly filled her old bras, her arse got to look real sexy as it wiggled now it had more to it and trousers were constantly being outgrown so skirts were the practical answer. The relationship just seemed to settle down to one of an established couple, I had plenty of money, bought my own car, bought Terri gifts and enjoyed myself. But by the middle of the next year it was clear Mrs Jones was never going to get better and she lost her fight to live. It was a sad day when I escorted Terri to the funeral, my dad had been very good and arranged everything, but I remember a very hard discussion between Terri and my mum, amongst all the many big things that need planning at a funeral, Terri was unsure what to wear, a dark suit or a black dress, really to go as the boy he was born as or the girl he had become. Relatives would be there he hardly knew so why add to their grief. Mum resolved the problem and took her to a mirror and asked what Terri saw, a woman obviously, so how could a woman go dressed as a man and not look odd. Let those others who have not been around to help while Mrs Jones was sick think what ever they want to, their opinion is of as much value as their help during the past few years. Nil. Terri bought a nice black dress that afternoon, and though some did mutter about who the was girl leading the mourners, no one challenged that weeping girl as she expressed her grief before everyone.
Terri was now lost with no one to care for, and no college or work to go too she sat in the house alone and tried to consider her future. I was round there a lot though not for any pleasure of my own, rather being a good friend and looking out for her. Sometimes I would find her sobbing at the loss of her mother, on one ocassion I found her naked staring at herself and questioning what had become of the boy she once was. time to act I thought, the grief I can cope with, the doubts about being anything but a girl, my girl, I could not consider. I treated her to a new dress for the summer, I made her go to a salon and have a proper make over, the works I insisted. Maria went with her and I was amazed at the difference. I was used to the wig, but that had gone, her own hair was now long enough to be styled into a spiky cut with long side burns and back with the ears showing, and all coloured chestnut. Her eyes had lash extensions, her brows tinted, her lips plumped, and after many attempts to get her to grow her nails which kept breaking, she now had long nails with the french tips. I was poorer but so pleased she had gone, it really made a difference to her personally. And for the first time since her loss we had sex, I even had the nail marks to prove it, though I was not complaining.
My father offered to help sort out her finances when it was clear she had no income besides the dole now the carer allowances and pensions had gone. She did inherit the house and if she went to college could get extra support while studying, but it was still not much so I offered to help by moving in and sharing the costs. This was viewed differently by everyone. My dad thought I was a fool, my mum thought me generous, my sister thought I was after sex, I think maybe all three had some truth. Terri did not really get a say in it, I still saw her as my girl and I was the boss. So I just moved in. This gave her someone to look after and a purpose to doing things about the house which helped with the grief. I also got to see her fulltime which was a delight as I have always loved her in sexy bedclothes of which I made sure she had plenty.
A few things had to change though, she was unhappy sleeping in her mothers double bed and her single was too small. So we redecorated and bought a new bed, but in the choosing of colours she would be undecided between pinks and flowers against darker greys and geometric designs, I could see the two sides of her pulling at her chioces. My solution was to get her navel pierced and then get a ring made with 'Brian's girl' written on it which I then made a big thing of fitting before making her close her eyes and carefully fastening shut so at all times she would have a permanent reminder of who she was. We had the pink walls with drapes over the bed, it looked very different and totally hers.
Without Mrs Jones pills I eventually ran out of hormones and came clean with her about what her mother had done which explained why she had a beautiful figure. She actually guessed once the nipples had become sensitive but had never been able to tell her mum to stop any of the things she had done to her, so it was now easy to take her to the doctor and get referred to a specialist who put her on a proper regime of hormones and blockers and when he realised how long Terri had been living as a woman asked if she meant to stay that way and possibly have surgery. Now that I thought was possibly my ultimate goal, my girl as all woman besides the ovaries. It had to be her who said yes to the doctor but I would be pushing from the background like mad.
Womanless Wedding Story
We bumbled along like a couple for ages, I got fully trained and started earning decent wages, Terri did college courses until she was happy to look for work, taking a job in a care home for the elderly. The doctor had insisted on counselling which she did with a commitment I had not seen before, and did worry it might undo all the feminising we had done up till then, but she never expressed a need to be a boy again. She never got the surgery done though, we stayed as a couple when many friends were getting married, which irked me as I could not, so I hatched a plan.
With my families help we planned a holiday in the states, but I had done my research and the hotel we were stopping at would be hosting a womanless wedding. Terri knew nothing of this until we got there and saw the posters and preparations for this event. I 'innocently' suggested we could enter because technically Terri still had male on her passport. The town was doing the weddings as fund raisers and two other parties were due to get married on the day. Maria persuaded Terri that it would be great to go shopping for a dress and get all dressed up, Terri was convinced and all I had to do was set up the wedding as I wanted it while they went out and bought or hired everything they needed.
I did not see Terri for two days, she slept with Maria and seemed to be having a great time if their reports were true when I caught up with them for lunch each day. The big day arrived, Terri and Maria did not watch the first two ceremonies, but they were truly all men and looked like it. Then it was our turn, I stood before the rows of people I had no idea were going to be still there, waiting for Terri to appear. She was beautiful in a long white gown, viel hiding her face, with Maria in a long cream bridesmaid dress beside her. Everyone cheered as she came in though I doubt any really thought she was a man underneath the dress, she was just too good. We did the vows, the rings, the first kiss, the signing of a register and then later the first waltz as man and wife along with two other couples. The wedding was maybe not quite a traditional white church wedding, but she had my ring and I had a certificate which had been signed by a legally authourised person. She might not fully know it but we were married. That night I called her Mrs Smith as I helped her out of her dress, and explianed that in taking my name she also accepts my authority, as in the honour and obey of the vows. She stepped out of the dress and looked fantastic in her white underwear and said 'I gave up challenging you years ago, was it in entering the contest, or the red studs, or maybe the toilet seat charade, I am what you made me, to be Mrs Terri Smith is just a confirmation of that. What else can you do to me?'
I picked her up and carried her to the bed, I lay down beside her, 'you make me sound like a bully, surely I was just coaxing you in the direction'
'Maybe not a bully, but you knew how to make me do things I did not necessarily want to'
'And are you unhappy with the prospect of being my wife'
'No, it kind of just follows on, besides who else would have me'
'Even if you don't love me I do love you and have done since before you won that contest. There is however one thing I would like you to do when we get home'
'As well as cook and clean for you'
'Those as well, I want you go to the doctor and arrange to have this' I touched the hormone shrivelled penis 'sorted out. Doing it because you love me, would be great, but if you can't do that, do it because you are Mrs T Smith now and will obey my wishes'
'And if I don't want to?
'I don't think the lovely Mrs Smith thinks it might be an option'
'Just seeing if there was an option...........Now then does my randy husband wish to wait until I have a front hole or is he happy to use the one a little further back for now'
I could not believe it six months later I picked her up from a clinic and helped her to carefully sit in the front of the car, I knew I would not be going near her for many weeks, but the satisfaction of knowing that beneath those bandages was a hole and not a dick was consolation enough.
I had converted my mate Terry into my wife Terri and I for one loved her even if she never told me she loved me I knew she needed me and would do anything for me, that and looking beautiful and sexy was enough for me.
The end
As promised, Naci Rema's rewriting of the story with her take on events if they happened in the US, and with her own twist on things.
Dare I ask which version you prefer, no rude or over critical comments please, both versions were written for fun, not for a Booker prize. Enjoy!! :)
Terry’s Story
My name is Brian Smith, and I have know Terry Jones since we were kids. We played on the same street, went to the same school and got involved in the same things when we were little. As we grew up, I got bigger and stronger and was good at sports, while Terry just seemed to stay short and skinny and avoided athletics. In fact, he was always the smallest boy in our class, and even by the time we reached high school he could best be described as a runt. As such, the bullies would have picked on him mercilessly, but he managed to keep them laughing by using his high pitched voice to imitate our female teachers. And, off course, he had me as a friend who would stick up for him if necessary.
The other difference between us was our home life. My parents might have started in the same area as Terry's family, but my dad worked hard at building a profitable business and we moved into better places several times, until we had a big house in the nicest part of town. It was a mansion compared to Terry's tiny home, but at least he did have his own room because he was an only child.
The reason for my friend’s relative poverty was because his father had run out on the family shortly after Terry was born, leaving his mother to raise and support him on her own. Even though she had a decent job, money was always tight. This was made even worse in recent years because she had developed a chronic illness which caused her to miss work a lot. Terry was a good son and did his best to take care of her, which with school and homework didn’t leave him much time for a social life. This was just as well, because a small, shy, skinny boy attracted little interest from the girls.
A very significant event occurred during our junior year in high school. At the time I had just turned seventeen, but Terry was still fifteen due to his having skipped a year of school early on. While waiting in line with him at the school cafeteria, I noticed a sign on the bulletin board about a 'Womanless Beauty Contest'. Neither of us had heard of such a thing, so we read the small print and learned it was a fundraising idea the school board had come up with to help make up for the recent loss of state funding for music and arts programs. Boy students would dress up and perform like women do in normal beauty pageants, to the amusement of their family and friends who would buy tickets to attend. The main thing that caught my eye was the winner would get $500!
We were eating our cold pizza and cokes without saying much until I blurted out, “Terry, you should enter the contest! With your longish hair, baby face and small size you could easily look like a girl. And more importantly, you could really use the prize money since you’re always saying how broke you are.”
He just said, “No way!” and gave me an ‘are you nuts?’ look, but I ploughed on with ideas. I could get some clothes off my sister, who was about his size. His mother, although frail, never looked anything but well dressed with perfect makeup, so she would surely be able to help in making him look attractive. And, for once, his small, almost feminine features and lack of muscles would come in handy!
I kept on pressuring him, though I wasn’t quite sure why. In the end I made him promise to tell his mother about the contest and see what she thought of it. Terry was never a strong willed guy, and I just overpowered him with my more forceful personality.
The next time we saw each other, I immediately asked my buddy if he had told his mother about the contest. He reluctantly admitted that he had, and then, red-faced, he went on to say she not only thought his entering it was a great idea, she insisted he sign up right away! I could tell this was not what he had wanted to hear, but Terry was always an obedient son, and so before the day was over we went to the school office and filled out an entry form for him. Since it was all my idea, I even paid the fee!
And so, little Terry was going to be in a beauty pageant, and for some strange reason I was as excited about that as my friend was upset about it. The date was four weeks away, just before the Easter break, so we had time to prepare and plan for his performance.
My first job was to ask my sister Mary if I could have some cast off clothing of hers. When she asked what for, I explained that it was for my friend Terry, who was going to be in a beauty pageant. She looked at me with a funny smirk on her face, but agreed to give me some of her old things. I left her room with several bags of clothes and shoes, and an offer to help in getting my pal to look like a girl if it was needed.
Next, I went over to Terry's house and found him cleaning the kitchen while his mother was resting in a chair watching TV. As always Mrs. Jones greeted me with a smile, but she never got up, just tucked her medicine bottles out of sight. A minute later, Terry came out to say hello. He was wearing one of his mother’s aprons and looked surprisingly feminine already. I showed him the bags of clothes my sister had given him, and while Mrs. Jones seemed pleased, I saw in my friend’s face a sad, almost resigned look.
I was invited to stay a while and visit, but after a polite chat I got up and left. Terry’s mother said they would sort through the bags later on and see what there was that he might be able to use for the contest.
I would have loved to have been a fly on the wall as my friend tried on the sexy clothes and high heel shoes my sister always wore, but I had to make do with an update when we met at school two days later. In a hushed whisper he let me know that his mother had insisted he try on everything Mary had offered him, and he now had more girl clothes than boy stuff hanging in his closet! For some reason that I couldn’t quite understand, hearing this excited me.
Terry then produced a list of things his mother said he would need if he wanted to be the prettiest boy in the contest. First, high heeled shoes…neither my sisters nor his mother’s were the right size or style; and also makeup…his mother had some, but not the right sort apparently. I learned she did however have a wig Terry could use. Even though his hair was a little long for a boy, it still wasn’t the proper length for a beauty pageant, and fortunately her wig was.
I also learned Mrs. Jones had some silicone breastforms she wanted her son to use! Terry’s face turned red as he explained that they were apparently very realistic, since his mother had assured him they would jiggle and bounce just like real ones when he walked! Cancer immediately jumped to mind as the reason Mrs. Jones had them in the first place, but I didn’t wish to pry in case I was right.
By this time I was really getting carried away with the whole thing, and I immediately offered to buy my friend the needed high heeled shoes and ask Mary for makeup and wig styling advice. It looked like this was going to hurt my pocket as much as it would hurt Terry's male ego, but strangely, I didn’t care.
That Saturday found me at Terry's again. This time things were very different - his mother answered the door with a big smile on her face! She gave me a peck on the cheek and ushered me into the living room. As I sat down, I was wondering what to expect next. I quickly found out when Mrs. Jones called to the kitchen, “Come on in, Teresa. It is only your friend, Brian. Come and show him how good you look!”
The first thing I had not expected was that Terrance, as his mother always called him, would now be called ‘Teresa’. The next was the person who stood at the doorway, head bowed, looking very nervous.
“Come on now, Teresa, let our guest see you.” When Terry slowly walked over and stood in front of me, I was speechless! He was wearing a blue long-sleeve top, a knee-length skirt, beige pantyhose, and black ballet-type flats. That was only the start. The chest on 'her' looked just right (later I was told it was a C-cup), and “Teresa’s” hair was now shoulder-length, thanks to his mother’s wig. Also, when ‘she’ looked up, I could see some make up had been applied, which had made a big difference to the formerly boyish face, and ‘her’ fingertips now sported long pink artificial nails!
“You won’t tell anyone at school you saw me like this, will you?” he asked nervously.
I agreed not to, but from that moment on I knew Terry, or rather, Teresa would be a hit at the contest. But more than that, I found seeing him dressed like a girl to be unnervingly appealing. While I’d never had a girlfriend before, and I had often looked at girls and rated them on their attractiveness, and ‘Teresa’ was off the charts! I wanted to tell Terry how beautiful he looked, but it seemed wrong for me to say to my boyhood friend something that would only be appropriate to tell a girl. His mother had no such hang ups and went on and on about her lovely ‘daughter’! Finally, an embarrassed Terry had heard enough, and he went off to get us all a drink, much like he would have done before, but dressed as a girl he just seemed to be acting more in the feminine role.
While we enjoyed our iced tea, we talked about what ‘Teresa’ would require for her further development. And once again, I offered to pay for anything extra that was needed. Mrs. Jones patted my hand and thanked me for my support. Then, she made plans for me to take Terry shopping the next day for women’s shoes, and if Mary did not have any spare makeup, we would buy some of that, too. I was wondering how two boys might get away with shopping for such girly stuff, but that was just something we’d have to figure out if this idea was going to succeed.
After a while we left Mrs. Jones on her own and went upstairs to Terry's room. It was certainly different than I had remembered, with my sister’s clothes hanging in his closet, her shoes on the floor and in front of a mirror were the few makeup bottles he had used.
I started off with, “Wow, I thought you would just have to wear a dress on the day of the pageant, not all this!”
Terry looked down at the floor. “Pretending to be a girl is not that easy. At first, I wanted to do as you said, but Mom decided I need to get used to the ways of femininity if I want to win the contest. The only good thing about all this is that my mother has been the happiest I’ve seen her in a long time. She’s really enjoying having a ‘daughter’ around for a change.”
“What do you mean by getting ‘used to the ways of femininity’?”
Terry hesitated before finally blurting out, “Mom thinks I need to live as a girl as much as possible during the next few weeks! She wants me to sort of immerse myself in the role, so that when I walk out on stage I’ll think of myself as Teresa and not Terrance!”
“Are you kidding me?” I asked in amazement.
“Unfortunately, no. Mom says from the moment I get home from school until I leave to go back the next morning I have to dress and act like a girl. She’s begun to scold me if I show any boyish traits, and insists I spend most of my free time practicing styling my wig and putting on makeup!”
I tried to stop myself, but then it was my turn to blurt out, “If I was to say you look pretty already, would you be mad?”
“I…I guess not, but don’t you think this whole thing is kind of strange?”
Quickly I replied, “No, it’s just all in fun, right?” I wasn’t going to admit to my earlier thoughts that I was actually feeling attracted to him. I was sure he’d quit the contest immediately if I did, something I was suddenly anxious not to happen.
Terry changed the subject to school, and asked which girls I found attractive. I admitted it was the ones who had long, slim legs and big chests. “A typical guy answer,” he replied with a smile, which looking the way he did didn’t sound strange at all. I asked what he looked for in a potential mate, and he said he thought friendship and a common bond were more important than appearances.
To this I immediately replied, “Well, I also think those things are important in a relationship. For example, with us we have the friendship, a common past, and now a common purpose, you winning the contest.”
“And you’re not just saying that because I have nice legs and a good pair up here too?” he asked with a grin as he glanced down at unfamiliar mounds on his chest. I knew Terry was just teasing me, which was good since it meant he was becoming more relaxed with his new feminine appearance.
“The nice tits do help, but I'll pass judgment on the legs until I see you in a mini-skirt!” For that comment I got hit on the arm. Only, it was not a hard punch a guy would have given me, but more of a girlish, playful slap. I was pleased that even alone with me Terry was staying in the role of a girl.
I looked in my friend’s eyes, which seemed softer and more alluring from the makeup. “So, do I call you Terry or Teresa now?”
“Mom says it should be Teresa when I’m all dressed up like this,” he replied bashfully.
“I think your mother is right, Teresa. And, if you practice hard I’m sure you will make an excellent ‘womanless' beauty pageant contestant!”
Nothing much else happened that evening, but I did arrange to meet Terry at the local mall on Sunday to buy him some high heeled shoes. Once again, I was feeling excited, picturing how much sexier ‘Teresa’ would look mincing about in towering stilettos!
I met up with my friend at the mall as planned. I smiled when I saw that he looked very nervous and was wearing a baseball cap and sunglasses to try and hide his identity. Despite that, with his longish hair and pretty face he still appeared very girlish, which pleased me greatly.
When I asked how he was doing, Terry turned bright red when he said, “Mother thinks I need some new girl’s underwear as well, if you can afford it…” I didn’t answer immediately, my mind trying to picture my boyhood friend all dressed up in sexy lingerie like I had seen in Victoria’s Secret! So, he continued, “Just panties really, and maybe a bra. I hope you don't mind, but Mom’s social security check hasn’t come yet this week and we’re kind of short.”
“I don’t mind paying for your girly underwear,” I insisted, “but how can you be sure of the fit without trying them on?”
“Mom said buying the feminine undies will be no problem. She wrote down my sizes and told me to just say they are for a girlfriend.”
And so, we went into a women’s clothing store, blushing a lot as we walked along the racks of soft pretty underwear. I smiled when I noticed Terry nervously fingering a lacy black bra. I’m sure he was agonizing over the fact that his mother had insisted that he wear such garments on a daily basis until the womanless pageant.
“Can’t we just buy some plain white cotton bras and panties?” he asked hopefully.
“Of course not!” I replied with big grin. “You want to be thinking like a sexy girl for the contest, right? That means you should be wearing the hottest underwear we can find, to put you in the right frame of mind.”
With that I headed over to the bra and panty sets and picked out the most sexy ones they had in my friend’s size. Terry made one last protest that the garments were far too sensual and erotic for a boy to be wearing, but I just grinned and took the lingerie to the checkout counter.
I walked up to the cashier and muttered something about them being for my girlfriend. The older woman glanced over at my feminine-looking companion and said with a smirk, “I hope she appreciates how embarrassed you are getting these things for her!” I turned bright red when I realized the cashier knew they were for Terry, and I paid without saying anything else.
Fortunately, my friend hadn’t heard her snide comment, since he was desperately trying to figure out how he could try on women’s shoes without being labeled a queer. Suddenly, he had an idea. We would avoid regular shoe stores and just shop in one with rack upon rack of stock. There, he could try women’s shoes on without any salesman’s help.
And so, we walked around the mall until we found that kind of shoe store. The plan was simple. First, we would wait until the aisle containing his size was clear. Then, while I looked out for anyone coming, Terry would slip his shoes off, revealing feet encased in girls tights, and try on some appropriate high heeled shoes.
Having seen many beauty contests on TV, I had a good idea of what to look for. And, in the third shop, I found them — pointy-toed, black stiletto, 4 inch pumps! Terry immediately protested, saying he could never walk in shoes with heels that high, but I was insistent and he finally gave in and tried them on. At first Terry complained that the pumps were too tight, and I explained that my sister said the same thing about her shoes but wore them anyway, because they made her feet look smaller and more feminine. Hearing that, he reluctantly forced his feet into the pumps and stood up. I had to catch him when he did, because he almost fell over from being unsteady in the unfamiliar skyscraper heels! Gradually, he regained his balance and managed a few tentative steps, teetering precariously the whole time. I wanted him to practice some more, but Terry heard a salesgirl approaching and quickly slipped the shoes off and back into their box. I blushed again as I went to pay for them. No comment this time from me or the assistant, just a ‘no’ when she asked if I wanted any stockings to go with them.
I had reached my limit on embarrassment, and we still hadn’t addressed the makeup problem. Luckily, Mary had said she would go out and buy what she called a “starter kit for the beauty queen!”, so we called it a day and went back to Terry’s home to show his mother his new lingerie and high heels.
On Monday I brought him the make up Mary had purchased. My boyhood friend was all set up now for his big day as a woman in a beauty contest! I wondered if that thought made him shiver as much as it did me.
A week of school past and there wasn’t much talk of ‘Teresa’ until Friday, when Terry asked me to come by his home the next day. I asked him what for, but he refused to say anything more.
On Saturday I was greeted at the door by Mrs. Jones, who gave me the now customary peck on the cheek. Once again, Terry was in the kitchen, and I could see from the back that he was wearing a velvet dress, dark stockings and the new high heeled shoes. I was going to say something corny like, 'You look good enough to eat!', but stopped myself when he turned around. I couldn’t help but stare at his soft wine-colored lips, big defined eyes and the inviting mounds on his chest!
Mrs. Jones then spoke for me. “Teresa does look beautiful, doesn't she?” I was at a loss for words. “I tell her that all the time, but she doesn’t seem to believe me. You tell her, Brian. I am sure she will trust you.”
“Well, er, yes, he…I mean…she looks…well....er... very pretty!”
Terry looked down at his feminine-looking hands tipped with long wine-painted nails, and said in a soft, higher pitched voice, “It's alright, Brian. I know I look like a girl…I just don't want to believe it.”
“Well, you had better believe it!” I almost shouted, “because you look fantastic!”
Terry blushed prettily and then went over to the table and laid out the food for our meal. It was obvious he and been practicing walking in the tall spike heels, because he handled them as well as any real woman would. I was mesmerized as the stiletto pumps caused his shapely behind to wiggle enticingly in the confines of the tight dress he wore.
After a meal in which I couldn’t take my eyes off my gorgeous friend, Mrs. Jones went out with some neighbors, leaving us in the house alone.
“Do you realize how terrific you look?” I blurted out, still not understanding the strange emotions my crossdressed buddy aroused in me.
“Please don't tease me,” he said with downcast eyes. “I feel awkward enough as it is.”
“No, I mean it. You do look very good…even hot!”
“No, I don’t! I can’t!” Terry insisted, his eyes misting up at the idea that he could actually look desirable to other males. Finally, he calmed down and said, “Anyway, Mother wants me to go out in public as Teresa to get used to being seen as a girl before the contest. She says this will boost my confidence.”
“Mother? Since when did you start call your mom that?”
“Since she told me to. She says it sounds nicer in this girly voice she also insists I use. So listen, I’d like someone to come with me when I go out. Will you do that for me?”
What else could I say? “Of course I will. Just tell me when you want to go out, and where you want to go.”
And so, later that evening after it turned dark, we prepared to venture outside. Terry borrowed a woman’s coat from his mother to wear. It was way too short for him, but I didn’t mind since it gave me a better view of his long, slim legs perched on the skyscraper heels! I began to walk to the front door, but Terry insisted we slip out the back door after I had made sure no one was watching. The outing consisted of a bus ride into town, a short walk around with Terry’s spike heels echoing off the deserted streets, a coke at a Burger King and then back on the bus. We were home by nine. Mrs. Jones was thrilled to hear about her “daughter’s” first time out in the world, and thanked me for being such a good friend.
As I left, she thanked me again, and I said anytime Teresa needed someone to take her out, I would be only too glad to volunteer. Mrs. Jones replied, “That would be wonderful!” and gave me a big hug. I doubted if Terry was quite so enthusiastic about the idea, because when I asked him if ‘Teresa’ was free Sunday evening for another trip outside, he just quietly said, “I’ll see you tomorrow.”
I arrived as requested the next evening, and took Terry for a walk around a nearby park. This time he wore a hooded coat his mother had found, which would help to hide him from possible meetings with people he knew. It was a cold night, so we found shelter and huddled together for warmth.
“Mother really likes me like this, you know,” Terry finally spoke.
“I guessed as much.”
“I have to wear dressy women’s clothes whenever I am at home now.”
“ I thought so. You’ve become very good at walking in those heels.”
“I know. It took a while, but I don’t feel in pain or out of control anymore when walking in these tall stiletto pumps. In fact, it’s when I wear my normal flat boy’s shoes to school that my legs ache. I think it has something to do to my tendons becoming adjusted to the heels, since I wear them so much now. Even worse, Mother said she would like to take me out to get several more pairs of high heeled shoes in other colors, to better match some of the dresses and skirt outfits your sister gave me!”
“That’s too bad,” I replied, secretly delighted that I would soon be seeing my friend wearing some new sexy footwear.
“Brian, do you mind me doing this? I mean, do you think it’s weird that your best friend is living as a woman most of the time?”
“Not in the least. I enjoy you more as a pretty girl than I ever did when you were a sorry runt of a guy!”
“Stop teasing!”
“Okay, but you really do make one pretty girl.”
“Please don’t say that…this is all so confusing!” Terry then turned to me, buried his head in my chest and began crying. I put an arm around his shoulder, and for the first time in our lives I hugged him! It felt so much like having a girlfriend beside me that I just naturally reacted as if Terry was one. In time he calmed down, and then wiped his eyes carefully like a girl would so as not to smudge his makeup.
“We better get you home,” I said, and took my friend’s hand in mine and walked with him just like he was my girlfriend. Now I was the one feeling confused!
The next day Terry and I met for lunch at school. I noticed his face had changed. For one, his eyebrows looked thinner than normal and more high arched, as if they had been plucked drastically. He reluctantly admitted his mother had done this to him against his wishes. She said it was needed for the beauty pageant, and it was better to do it now so any redness would have time to resolve.
I could also see a silver stud in each ear, which Terry said was more of his mother’s handiwork. She had done it with an ice cube to numb the sewing needle which pierced his lobes. Ouch! I thought.
We found a quiet corner, and I started to tell my friend how confused I was by how far Mrs. Jones was taking all this, but was quickly cut off with the reply, “You’re confused? How the hell do you think I feel?”
I tried to imagine how much Terry’s life had changed since I convinced him to sign up for the womanless pageant, but it seemed Incomprehensible to me. Then, he added, “And your asking to take me out certainly doesn’t help things!”
I told him honestly that I was best friends with Terry, but when I was around Teresa I somehow felt like I should ask her out. In reply, he insisted that I resist this urge and never suggest to his mother that we go out in public together again. He explained that she was already hinting that the two of us should go out on a real date together, which would be venturing further into a female lifestyle than Terry was ready for!
Then, he floored me by asking if Mary had a prom gown or some other fancy long dress that he could use for the contest. I said I would find out, but I doubted that my sister would lend something that expensive for a boy to wear.
To my surprise Mary did have a suitable dress for the evening gown portion of the beauty contest, a blue satin gown she had worn to her senior prom. She said Terry could borrow it as long as he came over and tried it on at our place first to make sure it would fit.
When I gave Terry the 'good news' about the ball gown, he thanked me and asked if he could stay at my house for the weekend when he tried it on. He explained that he was well known around his neighborhood, and he was worried someone might recognize him out in girl’s clothes. On the other hand, no one knew him in my area of town, so he could come and go as Teresa without question. I asked about his mother's care, and he said she would be alright for one night, since Mrs. Phillips next door would look in on her.
So, we made arrangements for “Teresa” to stop at my house the next weekend. My parents knew about the contest but were still a little skeptical about having Terry hanging around dressed like a girl. That was until they met Teresa and realized how good she looked! My mother took to the feminine version of my friend right away, and even offered him hair and makeup tips. My father was certain at first that I was trying to smuggle a real girl into my bedroom, and it was only when Terry spoke in his deepest masculine voice that dad recognized my boyhood buddy and gave him the okay to stay.
Among the other things we had to do that weekend was buy Teresa some shoes to go with the evening gown. This time Mary came with us to help Terry pick out some strappy sandals to match the prom dress. There was no buying in private this time. At Mary’s insistence, he had to shop at regular women’s shoe stores and try them on right out in public! Fortunately, with Terry dressed and made up like a woman, there was little chance anyone would suspect it was really a 15-year-old boy trying on high heels!
I could see though that my friend was terribly embarrassed when Mary insisted he try on and walk around in pair after pair of spike-heeled sandals and pumps. However, to my surprise, by the third store Terry seemed much more comfortable parading around in sexy evening shoes in front of other female shoppers. Still, when Mary finally decided on a pair to buy, I saw my pal heave a sigh of relief as he shifted gingerly from one aching foot to another.
When I noticed later that the new sandals had heels even higher than on his other shoes, Terry explained sheepishly that Mary had assured him they were the best match for his gown, even though she admitted they would be a little more uncomfortable to walk in. Hearing him say this pleased me greatly, since it was another indication that my friend was thinking more like a female, who would accept some discomfort for the sake of fashion!
While we were out shopping, we also picked up some cosmetics to go with the outfit, and a small clutch bag for Teresa's incidentals. I was a little surprised to see how much like a girl Terry acted in Mary's company, but when I asked him about this he said the feminine clothes he wore influenced how he behaved. For example, high heels made him walk differently, as did the unfamiliar weight of the artificial breasts on his chest. Also, having long hair, bangle bracelets and artificial fingernails affected how he moved his head and hands, and the short, tight skirt forced him to be extra careful about how he did many things, like sitting and picking things up off the floor.
I could only smile proudly as Terry linked my arm and thanked me for buying him the new evening shoes and bag. I had spent a small fortune on a feminine wardrobe for my boyhood friend, but I didn’t mind. For some strange reason, seeing the results gave me a warm feeling inside, which seemed to grow even more pleasurable the more he became Teresa. I still couldn’t understand why, but I had become determined to turn Terry into the most beautiful and sexy girl that I could!
That evening, Mary took Terry into her room to have him try on the complete outfit. After what seemed like hours, they finally reappeared. I was shocked to see that my best friend was unrecognizable! Mary's blue prom gown fit him perfectly. The bust was full, the long skirt and hourglass shape of the dress said sexy, and when he turned around, the lacing up the back revealed a hint of ass cleavage that looked terrifically hot! I couldn’t believe how well he moved in the skyscraper heels, and the redone makeup, long earrings and alluring perfume all added to his amazingly feminine appearance.
I just stared, open-mouthed, as my sister directed Terry to stand in front of me in a model’s pose, one leg forward, the other bent, and with a hand on his hip. Suddenly, I realized I was no longer confused about my feelings…I was in love! The only confusing part was that “Teresa” was not a real woman, but at that moment it didn’t matter. I just drank in what I saw and decided to worry about the details later.
As for Terry, I could see that he was also filled with mixed emotions. On the one hand, he seemed pleased with all the compliments that showered down on him. But, on the other hand, they were about how beautiful and feminine he looked, which must have upset his male ego greatly!
After a short while of Mary and my mother fussing around Terry to make sure the fit of the gown was perfect, he was ushered out of the room and back to the spare bedroom he would be sleeping in that night. There he changed into an off-the-shoulder dress and matching platform heels that Mary had lent him. The shoes were a little small on his feet, but they had an open toe and sling back, so he managed to squeeze into them.
Terry came back looking so sexy that I could feel myself stiffening in my pants! I assumed this was going to cause trouble later, but at the moment I was in heaven! After some more talk about what an attractive and real looking girl he made, which caused him to blush sweetly, Mary invited the two of us to go out with her and some of her friends to a nearby sports bar to watch a game and have some beer and popcorn. Even though we were both underage, she was certain that everyone would assume because we were with her regular friends that we older, and everything would be fine.
Terry seemed to accept this latest trip out in public as good practice for the contest, and Mary clearly enjoyed his company and made him feel at ease. That is, until she introduced him to her friends as my girlfriend! She later explained to the embarrassed boy how it was easier to do that than tell the full story. This left me an open door to behave like an attentive boyfriend to the hot girl I was with, since I did have to maintain the cover story for onlookers.
At first, when I sat close, put an arm over his shoulder, and took hold of his hand, Terry seemed shocked and put off by my advances. But, as the evening progressed and he had a few unfamiliar alcoholic drinks, he seemed to loosen up, and soon he was laughing and having a good time along with everyone else. In fact, my boyhood pal didn’t act the least upset when I went even further, like fingering his bra strap and putting a hand on his exposed thigh. Emboldened by this, I took a chance when Mary was in the restroom to sneak a quick kiss on his cheek! There was no instant passion in “Teresa’s” response, but I was not rejected or screamed at either. I was beginning to consider the possibility that maybe Terry liked being my girlfriend as much as I liked thinking of him as such!
We got home quite late and just said our good nights to Mary, who remained chatting with her boyfriend at the door. I took Terry to the spare bedroom and asked if there was anything he needed. Then, before I could stop myself, I kissed my friend again! It lasted only seconds, but it was full and firm and right on the lips! When I pulled away I said, “I’m sorry, Terry, but you look so darn good, and with us having played a couple all evening, I guess I was still in the role and did what felt right!”
Terry didn’t speak for a minute, fiddling nervously with a bracelet he was wearing. Then, with downcast eyes, he said that it was all really his fault, and apologized for leading me on! I immediately took him in my arms and gave him a hug. Then, I kissed him again, teasing his nice-tasting lips apart for a little tongue action in the process. This time I did not apologize when we stopped. Instead, I told him he could lead me on anytime he wanted to!
When Terry gave me a pretty smile in reply, I leaned forward to kiss him again. However, he put a hand up to stop me, saying he was dead tired and needed to get some sleep. In reality, he was wide awake, but knew he needed time to sort out all the conflicting emotions he was feeling.
That Sunday I took my “girlfriend” for a walk in the woods, suggesting along the way that maybe when the beauty pageant was over, “Teresa” would still like to appear occasionally for future dates. Terry immediately made it clear that the whole female impersonation thing was to win a contest, and when it was over Teresa would be gone for good. I defended my suggestion, pointing out that his mother liked having a daughter, I liked my hot new girlfriend, and even he seemed to enjoy being a she.
Terry hesitated with his reply. I could tell he was having trouble deciding how much to reveal to me. Finally, with tears in his eyes, he poured out his feelings, saying the whole situation was making him an emotional wreck! Here he was, a normal boy, but everyone seemed to prefer him as a girl. What’s more, his mother and best friend not only seemed to like Teresa more than Terry, they both wanted him to remain that way!
I immediately considered consoling my distraught pal with a hug, but I didn’t for fear it might make matters worse. Instead, I just patted Terry on the back and reassured him that I liked him either as a boy or girl. Then, I added that for now he should just give in and be my girlfriend Teresa for the sake of the contest, and we could talk about the future when it was over. After that, I took his hand and led the confused boy back to my empty house.
There, we had a bite to eat along with some wine my parents had left out. Then, with both of us feeling very mellow, I invited Terry to sit beside me on the sofa to watch some TV. He did so, tucking one high heeled foot under him like a girl would as he sat down.
“You know, if you let me, I would love to go out with you on a real date,” I ventured.
“I know,” came the soft reply.
“So, when can I take you out?”
“Please don't rush me! I’m just getting used to what it’s like being a girl, and next week I have the contest, unless you’ve forgotten.”
“I understand…I need to back off for now. But, that’s not a ‘get lost forever', is it?”
Again, Terry hesitated, before replying honestly, “No, not a get lost forever. But for now, please just shut up and watch TV!” I complied, but before the evening was over, I again had my arm around Terry’s shoulder and my hand on his stockinged thigh. He didn’t object to this, but I knew better than to try anything more then. Still, I was now filled with hope that our relationship would eventually more to another level. Strangely, I had completely forgotten that my girlfriend’s masculine body would severely limit how far we could go sexually.
By the time my mother had packed Teresa and her belongings into the car for the trip back to her home, I was sure I was going to be seeing much more of this girl. After they left, my father had a quiet word with me, pointing out that despite how pretty Teresa looked, she was still a boy, and one they all knew well. Yes, he admitted, Terry did look convincing as a girl, but he still had all the normal boy parts between his legs!
I replied that I knew all that, but when I was around Teresa her real sex never entered my mind. Dad understood my feelings well, having himself felt a stirring in his loins whenever Terry wiggled by in a sexy tight dress and skyscraper heels! He kept that to himself, however, and just answered that he wanted to make it clear to me that what I was doing might be thought of as gay. I nodded, and then asked if he had a problem with that. He thought again of the beautiful vision that was Teresa, and finally said he just wanted to make sure I didn’t get into something I couldn’t handle, and left it at that.
Now that my father had backhandedly given me his approval by not forbidding it, I was even more determined to make Terry my girlfriend! Despite that, it felt a little odd when I met him at school the next day. He still had his own, overly-long hair, pierced ears, and thin, high-arched eyebrows, and he even walked a little differently now, thanks to the many hours spent mincing in towering stilettos. However, I had no desire to kiss and touch him like I had over the weekend, which I think we were both grateful for. In fact we hardly spoke of ‘Teresa’ other than to discuss his preparations for the contest. In that regard, most of the organizing was out of my hands. Mrs. Jones, my mother and Mary had been in touch with each other, and come Saturday, Terry's life would not be his own!
First off, he would be prepared by his mother. I was told he would have to undergo complete body hair removal, prosthetic breasts would be glued on since the prom gown was too revealing for a bra, and his wig would be firmly attached to his own hair. Then, in the afternoon, my mother would pick Terry up and bring him to our place, where Mary would make him up, style his wig and get him dressed for the evening’s performance. All I could do was get in the way, so I made sure I was nearby to enjoy watching his transformation, but not underfoot.
The contestants were asked to be at the high school gymnasium, which was all decked out for the contest, by seven PM. To my surprise, Terry was not completely ready at six, as he sat without his wig on getting final touches to his makeup while wearing a dressing gown and matching high heeled slippers borrowed from my mother. Still, I couldn’t believe how beautiful he looked already, and I was anxious to once again see him in the sexy prom dress he would be wearing for the pageant.
At six-thirty I went with my father to pick up Mrs. Jones and take her to the school. I was surprised to see how fantastic she looked, dressed in a beautiful satin gown she had last worn as a young woman. It must have taken a huge effort on her part to look so good, considering her ill health, but there was no way she wanted to miss seeing her new daughter in a beauty pageant, nor be outdone by her son in looking glamorous!
Meanwhile, Mary and my mother took Terry and the prom gown to the girl’s dressing room at the gym, in order to make any final adjustment required. I imagine that sometime in the past few weeks a conversation must have occurred about how they would approach this contest. Would Terry be an outlandish drag queen, an obvious boy with a poorly fitting dress draped over him, or instead try to appear as a real female. I wasn’t sure who had made the final decision, but I would guess it was his mother since Terry didn’t appear the least bit happy about having to dress and act like an actual woman.
As we stood around, we could see all sorts of ways in which the contest had been interpreted. There were some shocking sights, like hairy-chested guys with ill-fitting dresses and bright red clown lipstick, but most of the boys had the nerve to hide their masculinity beneath a feminine disguise. And although I was naturally biased, I was certain my “Teresa” was the best looking of all!
The pageant started with the twelve contestants walking one by one up to the stage. The next to the last one out was Terry, who I was pleased to see not only handled the six inch platform heels he had on without stumbling, they also added a nice feminine wiggle to his walk! However, ‘Teresa’ didn’t smile at all and appeared very nervous despite getting the most enthusiastic response from the audience. I was concerned that this attitude might cost him points with the judges, but fortunately when one of the boys in the audience called out, “I’m in love!” , Terry laughed along with everyone else. After that he seemed more relaxed and even smiled a little, which made me feel better.
The first activity was an interview with the host, who asked each boy his reason for entering and why he wanted to win. Most made up stories they thought the judges wanted to hear, like doing it to stretch the bounds of sexual equality, or to be a good role model for gender-challenged youth. Terry just told the truth - that his mother was unwell and the money would be a nice financial boost for them. Then, he added that I had been his sponsor, and he thanked me publicly for all my support. It’s a good thing the audience was in darkness, or everyone would have seen me blushing beet red at this!
Next was the catwalk parade, where each boy had to walk up and down a runway and end with a model’s pose right in front of the judges. Of course, Terry won that. With all the practice he had walking in stilt-heels, he was a natural strutting back and forth on the runway, his cute rear end swaying enticingly with each mincing step!
Last, the panel of judges gave each contestant a random question, such as the one Terry was asked: “Do you prefer clothes from upscale women’s fashion stores, or do you prefer buying from trendy boutiques?” His answer was, “Neither… I’d rather have borrowed clothes, because they don’t cost my poor mother anything.”
After seeing some tears in a few judges eyes when they heard this, I felt even more certain of the contest’s final outcome. However, first there was a discussion over who the finalists would be. While this went on, a DJ appeared and some music started playing. The contestants were brought down to the main floor and encouraged to talk and dance with some young men who were recruited from the audience. I have to say that Terry mingled very well. All that taking him out in public as “Teresa” was definitely paying off. However, I did notice that when one eager guy took his arm and led him to the area cordoned off to be a ‘dance floor’, Terry did have a, “What have I gotten myself into?” look in his eyes! Fortunately, Mary had the foresight to show him how to dance like a girl as part of his training, and I thought he looked quite comfortable dancing backwards and in high heels!
Half an hour later the contestants were called back on stage, and the host announced the five finalists. Then, in dramatic fashion, one by one were eliminated, each given a small consolation prize before they left. Finally, it came down to just two ‘girls’, one of which was Terry! I watched with amusement as he and the other boy held hands just like real beauty pageant finalists might as they awaited the announcement of the winner.
Finally, after a tense pause, the host declared that TERRY JONES had won first prize! He added that this included $500, plus a beauty makeover at a salon in town and a gift voucher from a local fashion boutique! Terry’s smile lit up the room when the money was mentioned, but his expression quickly turned to one of puzzlement when the other two gifts were described. Then, he smiled again when he decided that his mother could put them to good use.
Next, a sash that said “Most Beautiful” was draped across his chest, a rhinestone crown was placed on his head and he was given a bouquet of roses. Suitably decked out, he was then asked to make the traditional “winner’s walk” back and forth in front of a cheering audience. I swear I saw tears in his eyes when he did so…I just didn’t know if they were tears of joy or of embarrassment at being declared the school’s most beautiful boy!
The evening continued, with the DJ playing his tunes well into the night. Terry was asked to dance by several more young men who wanted to have a spin around the floor with the beauty pageant winner. He reluctantly complied, but I could see that he was a little uncomfortable with the way some of them pressed their bodies against his and even gave his plump behind a squeeze or two!
I was upset at having my girlfriend courted by so many other guys, and when one fellow became especially frisky with his hands, I quickly cut in. I could see the relief in Terry’s eyes when I did so. He was apparently bewildered by all the unwanted male attention.
As we danced, I became aroused by the lovely creature I held in my arms. Without thinking, I placed a hand on the small of Terry’s back and let a finger caress his butt cleavage! Happily, while this had upset him when others tried it, I got the impression he was enjoying my attention! Mrs. Jones missed all of this. She had stayed to see her son win the beauty contest, but afterwards asked my father to run her home early since she was feeling very tired.
Terry and I danced until the lights were turned on and everyone was told to leave. After that, we all returned to my house for the night. As we sat up reminiscing over how well the contest had gone for ‘Teresa’, I felt myself once more wanting to make “her” a more permanent part of my life!
After a while the women went to remove their makeup to get ready for bed. Terry obviously had to go with them, since he was still dressed and made up like a girl. While the ladies were gone, I sat downstairs with my dad. Out of the blue he told me how feminine and sexy he thought Teresa was, and that he was not shocked that I found such a girl attractive, even if she had a little something extra in her panties!
While I was trying to get over the surprise of this comment, I was dealt an even bigger shock when the others came back downstairs for a nightcap. I had seen mother and Mary do this in the past, but to see Terry come in with hair still up in a feminine style and wearing a satin nightgown and matching high heeled mules was stunning!
When he sat down right next to me, I began to get physically aroused! Fortunately, we talked for just a short while about the evening’s events before Mary, mother and dad left, reminding me to turn off the lights when I went up to bed. After the footsteps had died on the stairs and doors had closed, I turned to face “Teresa”.
“I still can't believe how beautiful and realistic you look! Just for one more night, will you be my girlfriend?” I begged.
I could see Terry hesitate. The contest was over, and what I was asking was a little strange, to say the least. But, I guess he felt obligated after all I had done for him, and so he shyly nodded ‘yes’. And then, my girl moved even closer to me!
“Everyone loves you as Teresa, you know,” I said as I put my arm around my best friend’s small, thin shoulders. Then, I took that beautiful head in my hands and brought it up towards my mine and kissed those luscious lips once more! This time I felt Terry kissing back, and when my tongue went searching into his mouth, it felt no resistance. Before long I was massaging what I knew to be fake but very realistic feeling breasts. From there I worked my way up Terry’s slim legs and underneath his nightgown. The smooth skin was luxurious to the touch and the satin fabric felt very erotic, but when I realized there were no panties and no manhood to be found between his legs, I immediately stopped and asked him what the heck was going on!
An embarrassed Terry lifted the hem of his nightie and reveal a triangle of hair and no penis! Somehow Mary had fastened it back between his legs using surgical tape. When I pointed out that with this arrangement he’d have to sit like a girl to pee, he asked wasn’t that how I’d prefer it - with only one us having a penis? Then, already knowing the answer, he smiled and put a hand on my crotch. Now, until then, no other person had touched my cock, and I immediately began enjoying the unfamiliar sensations. After a few careful strokes by ‘Theresa’, I groaned and erupted into my pants!
“Is that what you wanted?” my ‘girlfriend’ asked coquettishly.
“That was more than I expected, thank you,” I gratefully replied.
“You had a big part in my winning today, Brian, so think of it as payment for all your support.”
“Well, that was some reward!”
“Glad you liked it,” my beauty replied as he got up and walked up to his bedroom, wiggling his satin-covered behind the whole way. I eventually calmed down after that wonderful experience and went to bed myself.
When I woke up the next morning, I had the unexpected surprise of seeing that “Teresa” was still with us! I had not realized it, but Terry had come the day before in drag, and had forgotten to bring any male stuff to wear after the contest. So, unless someone went to get his boy’s clothes from his home, he would have to look like a girl for as long as he stayed with us. And, I for one was certainly not going to rush out to do that!
So, I enjoyed having my beautiful girlfriend with me for breakfast and a little beyond. Finally though, Terry was anxious to get home and see his mother, so I reluctantly drove him back to his house. I stayed for a little while to make sure Mrs. Jones was ok after her tiring day, and also to relive the high points of the womanless beauty pageant with her. All too soon, though, I had to leave my beautiful Teresa and go home to catch up on schoolwork, which I found terribly anticlimactic.
I think it was mid-week before I saw Terry again. I accused him of avoiding me, but he said his mother had not been doing well, so he had skipped some classes in order to care for her. He told me how she had been thrilled to be given the salon voucher, but had refused to accept the cash he had won. However, I was sure Terry would find ways to spend it on her anyway. As for the boutique clothing voucher, he wanted me to give to Mary. While I told him this was a nice gesture, I refused, saying she could afford anything she needed with her high-paying job and would surely not accept it either. He didn’t know what to do after that, so I made arrangements to meet him at the boutique so we would see if there was anything uni-sex he could wear.
When we arrived there the next day, a very effeminate man offered to help us. Now remember, Terry still had the plucked eye brows, his nails were still manicured with traces of polish, and he had not completely lost that swishy walk he developed while wearing heels all those weeks. The assistant must have picked up on this and immediately showed him some extremely girlish things, like a salmon-colored shirt, tight fashion jeans and black slip-on shoes with a low heel, effusing over his pretty customer as he tried each item on.
I could see that my ‘girlfriend’ was going to turn down all the man’s suggestions as being too feminine, so I quickly jumped in and insisted they looked fine on him. So, Terry finally agreed to buy the salmon top, the black pumps, and the eye-wateringly tight jeans with no rear pockets, which looked so slim on him it was like he had leggings on!
After we had made these choices, the salesclerk asked if Terry would like to wear his new things home. When he hesitated, I insisted that he do as the man asked. So, within minutes I was walking out of the shop with a person who I could tell onlookers thought was somewhere between a girl and a boy, but not sure which!
One person who definitely liked the clothes we picked out was Terry’s mother. Unfortunately, Mrs. Jones said the wrong thing when she called Terry’s new outfit 'pretty'. She was clearly in a good mood due to her salon visit earlier that day, and looked so much better for the pampering she must have received. Still, the damage had been done, and I knew Terry would always have a bad feeling whenever he wore his new things.
For the next few weeks my life went back to the old routines - school, working, family, all the normal teenager things. I tried to see Terry as much as possible, but he usually had an excuse as to why he wasn’t available. Still, we would get together occasionally, at which times I would always hint about how much I was missing my girlfriend. He always quietly told me that Teresa was gone for good, and I should find myself a real girl.
However, it was Teresa who I wanted, even though I knew that was wrong. I was never sexually attracted to Terry, the boy. In my mind to have kissed him would’ve been gay. However, kissing Teresa was perfectly acceptable, and unfortunately Terry still reminded me a lot of her, especially when he wore his new outfit. I know it sounds confusing, but that was how my mind was working then.
Anyway, after four weeks I noticed that his nails were still a little long and very neatly filed, his face and arms were still hairless, and I could swear his eyebrows were not growing back, as if they’d been regularly plucked! The problem was, I could think of no reason for him to be doing these things, and he refused to answer any questions I asked about it.
I finally learned the truth by accident. On Thursdays, Terry and I had lunch at the same time, and so we usually ate together in the school cafeteria. One Thursday, however, he was missing, and I wanted to know if he and his mother were alright. Since he was one of the few kids I knew who didn’t own a cell phone, after school I stopped at his house on my way home to see if everything was okay. That was when it all fell into place.
I was greeted at the door by Mrs. Jones. She was not looking at all well, but had enough strength to welcome me in. Then, I was surprised to hear her call out, “Teresa, Brian is here to see you.” Turning to me, Mrs. Jones added, “She is in the kitchen making some lunch for us. I am not having a good day today, I'm afraid, and Teresa stayed home to look after me. I told her she can't afford to miss too much school since it will hurt her grades, but she ignores me.”
I got up and walked to the kitchen, where I was shocked to find a stunning looking young woman standing there. She just wore a simple tee shirt over a matching skirt, with a pretty apron tied around her waist. The high heels, makeup and long, femininely-styled hair she wore added a sexy quality to her outfit. Despite being almost unrecognizable, I knew this beautiful teenage girl must be Terry!
“You…you weren't at school, and I…I thought something might be wrong,” I managed to stammer.
“Come, sit down and join us,” said Mrs. Jones to her feminized son.
Terry just stood there, however, looking horrified now. Finally, he blurted out, “Mother was not feeling well this morning, so I thought I would be of more use here than at school.” He failed to mentioned why he was dressed as Teresa, something I was dying to know.
“Would you like to join us?” his mother asked me politely.
“I don't think so. I had better be going if you are about to eat,” I said as I got up to leave.
“Be a good hostess and see your friend out, Teresa dear,” Mrs. Jones said with a smile.
We walked to the door, with Terry’s high heels clicking a staccato beat on the hardwood floor. There, I turned to look at my stricken friend and he begged, “Please don't tell anyone about this!”
“Of course not, but, why…?” I asked as I waved my hand over his feminine form.
“I dress like this to please mother,” he explained. “She really seems to do better when I dress and act like I’m her daughter, Theresa.”
Confused, I said something inane like, “that’s nice of you”, in reply.
“Please...keep this our secret!” Terry implored. As bad as his life at school had been since being officially declared the ‘prettiest boy’, he knew it would become a living hell if everyone learned he was still dressing as a girl at home.
Suddenly, I realized I could have my Teresa back! “OK. It will be our secret.....just you, me and your mother. But, you have to agree to act like you’re my girlfriend whenever you’re dressed up as Teresa!”
For a few seconds, Terry just stood looking at the floor. “Brian, please, you know I’m not really a girl. This is all pretend. You need a real girlfriend…”
“No, I don't! Not when I can have the one I really want, which is YOU! You will be my girlfriend, Terry, and with the way you look, no one will ever be the wiser!” I realized I had my friend over a barrel. He loved his mother and wanted to make her remaining time on earth as happy as possible, but I knew he was afraid of what pretending to be my girlfriend would surely lead to.
“Brian, please, what I did for you last time was just done out of gratitude. I meant nothing by it other then that.”
“But, I think you did! You didn’t have to kiss me, you didn’t need to act like such a good girlfriend, and you certainly didn’t need to give me a hand-job!”
Tears started appearing in Terry’s eyes. I put a hand on his shoulder to console him. “Sorry, I didn’t mean to upset you. I just want Teresa back in my life.”
He opened the front door and said, “Please go, Brian. I’ll see you at school tomorrow.”
I bent to give him a kiss, but he pulled away. So, I left with all sorts of things running through my mind. It all boiled down to, “Teresa is back!”, and, “How can I get her to accept me as her boyfriend?”
The next day at school I made sure I met up with Terry. He was in his tight jeans, salmon-colored shirt and black slip-ons with the little heel, plus there was a faint smell of flowers about him which I deduced was from some perfume. He eyed my warily, apparently concerned I might want to talk about the way he was dressed the previous afternoon.
“Your mother better today?” I wanted to come right out and demand that he go on a date with me as Teresa, but I decided to try a friendlier approach.
“Yes, thanks for asking.” Then, he added in a whisper, “I didn’t want you to find me like that yesterday, but for some reason it makes my mother feel better seeing me dressed up as a girl, and I do it all the time now when we’re both at home.”
“I didn’t mean to embarrass you. I came by because you were off from school again and I was concerned about you.”
“Thanks,” Terry replied, giving me a warm smile of gratitude.
“I can't deny I liked what I found though.”
“I knew you would. That’s why I didn’t want you to find out about my dressing up.”
“But now that I have, when can I see Teresa again?”
“Please, Brian, I only dress as a girl to make mother happy.”
“What about making me happy?”
“Please don't pressure me,” Terry begged, with desperation in his voice. “I had hoped the contest would be the last time I’d have to pretend to be a girl…” I could tell his strength was leaving him, so I decided to press on.
“But, it wasn't, and now Teresa is back, making her mother happy. So, why not just go with it and embrace your feminine side for a while?”
“And make your dreams come true also?” Terry said with a grim smile.
“Well, that too,” I admitted, red-faced.
“And if I…say no?” he asked hesitantly. I could almost see my friend’s resolve crumbling before me.
“If you say no, I will just keep coming to your house whenever I don't see you at school, because I’m sure to find you there being Teresa.”
“What if I refuse to see you?”
“I don’t think that will happen, since I know your secret and I’m certain you’ll want to stay on my good side to make sure it remains one!” I knew I was being harsh, but I realized I might only have this one chance at getting my girlfriend back, and I wanted to make the most of it.
“Please, don't do this,” he begged, as he started to tear up again.
I felt sorry for him, but I decided to go for the kill anyway. “And, keeping on my good side means becoming my steady girlfriend, and all that implies!” There, I said it. If Terry would not act as my loving girlfriend, he knew the whole school would quickly find out about his secret crossdressing.
I never thought of myself as a bad person, but I could see in his eyes that I had destroyed the boy I had grown up with. I knew this, but I didn’t care. I wanted Teresa, and so Terry would have to go.
“So, I’ll be seeing ‘Teresa’ soon?”
I swear Terry swallowed a sob. “I don't have a choice, do I?”
“Not really. See you later, Terri!” He looked startled, as if he could hear I was pronouncing his name with an “i”. And, from the look of defeat in his eyes, I knew I had my girlfriend back!
Terry made no effort to avoid me at school after that, and he acted in public as if everything was the same. But, we both knew our friendship had changed. We were no longer equal male buddies. Instead, in our relationship I was now in charge, and he would have to do my bidding. I know this made me something of a bully, but despite that I enjoyed the hold I now had over my friend.
For example, when I saw Terry the next day, he did not smell of anything besides clean. So, I subtly commented on how nice he had smelled the day before, and he blushed and promised to wear the scent for me next time. I wasn’t positive he would, but sure enough the next lunch I spent with him he smelled of the perfume again. When I asked what it was, he told me it was a small sample his mother had gotten as part of her beauty makeover. In her weakened state, the scent was a little too strong for her, so she had asked “Teresa” to wear it instead. I told him that when it ran out, he should let me buy him some more, rather than going back to his old male cologne. Rather meekly he agreed, and told me its name. The following Monday I gave him a bag with a bottle of “Desire” in it. He took it and said thank you with a shy smile, but to me what happened had much more significance. Terry was now wearing a woman’s perfume just to please me. Besides that, he had accepted my feminine gift just like a girl would from her boyfriend!
I had a plan not to rush Terry into things, since he could always call my bluff and walk away. So, for a while, I left this stage of his feminization at just the perfume. But, I also made sure to compliment him on his appearance if he wore anything vaguely feminine to school.
Then, when he finally missed a day, I made sure to call at his house on my way home. The door opened with “Teresa” hiding behind it, hoping no one outside would see him.
“Everything ok?” I asked as I walked in, staring appreciatively at my lovely girlfriend.
“Mother is not good at all,” he said, with obvious concern in his voice.
“I’m sorry to hear that.”
Then from the living room I heard a weak voice ask, “Who is it, Teresa?”
“Only Brian.”
“Come in Brian. How are you, dear?” she asked politely.
“Oh, I’m fine, thanks. It’s just that Teresa was not at school today, and I was worried.”
“That's sweet of you, but I am afraid it is me who is not doing well. I’m such a burden on my lovely daughter…”
Terry stepped to her side. “I don't mind at all, mother, you know that.”
I asked if there was anything I could do to help, and promised to call whenever I could. When Terry showed me to the door I couldn’t resist saying, “That top looks terrific on you!” It was the blue tight-fitting shirt he had on when I first saw him as ‘Teresa’.
“Do you have to say things like that?” he asked. “It’s very embarrassing.”
“I can’t help it. I always like seeing it on you because it really shows off your breasts and looks dead sexy!” That compliment just brought a disgusted look to Terry’s face. Still, I decided to take a chance and asked, “Do I get a goodbye kiss from my girl?”
When Terry made no attempt to kiss me, I put a hand under his chin and lifted it up until I could kiss those pink lips that tasted of strawberries. “See you tomorrow at school?”
“If mother is better.”
I kissed him once more, even more forcefully, and then left. I was elated! I was back to kissing my girlfriend, after thinking my chances of even seeing her again had died a few weeks earlier. Now, invigorated by that mild sexual contact, I knew I would want more. Even if the relationship was very one-sided.
That weekend I bought a another gift for Terry. The ear piercings had healed up well, but he only had plain studs to wear. So, I bought him some more earrings, this time with a ruby stone in them! I gave them to him on the Monday.
“Should I be grateful?” he said as he opened the box.
“A ‘thank you’ would be nice.”
“Thank you,” he said without emotion as he stared at the feminine earrings.
“I thought they would make a nice change to those plain ones you always have on.”
“I can hardly wear my mother's long dangling earrings to school, can I?” he answered sarcastically.
I gave him a grin. “Why not...I’m sure they would look lovely on you! Anyway, these are nice and discrete.”
“But, obviously a girl's earrings.”
“Yes, that as well, which we both know is why I got them for you.”
“And you want me to wear them to class?”
“Of course. They would go well with the red t-shirt your mother likes you to wear.”
Terry let out a big sigh and asked me how Mary was now that she had left home. He was trying to change the subject, but I didn’t object since I knew I had won another battle in my efforts to feminize him.
When I met up with Terry the next day, I could see under his hoodie the red top and his new red stud earrings. I pulled the hood back to get a better look, and as a tease I said, “Maybe I should have gotten a larger stud…”
He replied immediately, “No! These are fine just as they are, thanks.”
“So, you won’t mind wearing them all the time for me?”
He nearly said something in defiance, but backed down and just mumbled, “I guess.” The next day I was pleased to see the studs were still in their place, making his small ears look even prettier.
My next move was to visit Terry at home on a weekend. At first, I couldn’t think of an excuse to stop by, but then I thought, ‘Who needs an excuse to see their girlfriend?’ So, I just turned up on Saturday around 7 PM. Terry looked shocked when he opened the door. As I had hoped, he was completely dressed and made up as Teresa!
I was quickly ushered in and went through the usual polite “how are you’s” with Mrs. Jones. She invited me to join them in watching some TV, and insisted I sit with her ‘daughter’ on the sofa. As Terry slid over to make room for me, I took in the full picture of my boyhood friend. He was wearing a tight-fitting pink silk dress, pink lace-top stockings and his black stiletto heels. I noted with excitement that I could see a little of his white lace bra peeking out!
As we watched a movie that could be best described as a ‘chick-flick’, his mother said, “Those pretty earrings you bought for Teresa are so nice. She never has them out of her ears now, she likes them that much!” I could tell that Terry was about to give a rebuttal, so I interrupted him.
“I just wanted to give your daughter a gift, so she doesn't feel neglected by her boyfriend!”
“How very thoughtful of you, Brian!”
When the movie was over, Mrs. Jones got up and said, “If you young people don't mind, I’m feeling tired, so I think I’ll head off to bed.”
It was only eight o’clock, but I just assumed that her illness made her tire out more quickly. That is, until she leaned over to give me a goodnight kiss on the cheek and whispered, “Have fun, you lovebirds!”
As Terry went with his mother to help with whatever she needed, I considered what I had just learned. Not only did Mrs. Jones know that her son and I were intimate, she actually seemed to want to encourage it! I wasn’t sure why this was, but I guessed it had something to do with her wanting Terry to not only accept being her daughter, but to enjoy himself as Teresa also.
While I waited, I amused myself channel-hoping until I found a fashion show which I thought might be a good tease for when Terry returned. When he finally showed up fifteen minutes later, he started to sit in one of the chairs, but I quickly patted the space next to me on the sofa to remind him that this was where my ‘girlfriend’ belonged. Then, with my arm around his shoulders and my hand resting on his nylon-covered thigh, we watched the fashion show.
Terry seemed a little stiff at first, especially when I made comments on how I though each dress might look on him. But as the evening went on, he seemed to loosen up and even snuggle a little closer to me. I thought this made a for a nice first night in with my new girlfriend, so I didn’t try to take things any further for fear of scaring him off. Whether Terry was cuddling up to me to get on my good side, or because he really wanted to, I wasn’t sure. But I was content with the progress I was making, especially after the goodnight kiss I gave, which ‘Teresa’ seemed to reciprocate!
I visited every Saturday evening for the next three weeks, and the same pattern followed: polite chat, Mrs. Jones going to bed early, and cuddling with my girlfriend. By the third week we had moved on from a goodbye kiss at the door to kissing in the living room! I got the happy feeling that Terry was gradually growing more accepting of his new role as my girlfriend. What happened next took me by surprise, but actually helped further my grand scheme.
As usual I came to visit on Saturday, but this time when Mrs. Jones sent Terry to make her a hot drink, she conspiratorially leaned towards me.
“Brian, you seem to be having a nice softening effect on Teresa.” I looked at her questioningly. “You know, the earrings, the perfume, and especially what you two do when I go to bed!”
“Oh?” I said, trying to appear confused.
“Don’t act so innocent,” she said with a knowing smile. “I might be sick, but I still see and hear what is going on!” Then, she put her frail hand on my arm and continued.
“I want to ask you a favor. Sometimes I still find the toilet seat up after Teresa has done her business. I remembered that dress she wore to the contest was so low cut at the back that she could not have been wearing panties, am I right?” She didn’t wait for an answer. “So, the floppy bit between her legs must have been tucked away somehow. Now, what I am asking you is, can you persuade her to do that all the time? It is not nice thinking of her standing up to relieve herself like a boy, but if she has her thingy safely tucked away, then she’d have to sit like a normal female to relieve herself.”
“Well, I guess I could have a word with her about it,” I said nonchalantly, while inside I was jumping for joy at being given the lead-in to the next step in Terry’s feminization!
Just as Mrs. Jones finished, her ‘daughter’ walked in with a tea for her, a beer for me and a lemonade for herself. No mention was made of the previous subject, and we discussed some item on the TV instead.
Later that evening, I was cuddling with Terry as usual, waiting for just the right time to bring up what his mother had asked. Finally, he excused himself to use the bathroom, and I blurted out, “Your mom doesn't like you standing up to pee!” This got a swift reaction.
“You’ve been talking with mother about me?”
“No, it’s not what you think. When you were out of the room, she told me that she really likes having a daughter around, but when you leave the seat up it ruins the illusion. Couldn’t you just fix yourself up like you did for the pageant?”
Terry calmed down a bit and explained, “It takes a lot of effort to get myself all taped up…and it’s very uncomfortable to undo it later.”
“Well then, why not do it once and keep it that way all the time? Then, you would always have to sit when using the bathroom, and you’d never have to worry about forgetting and upsetting your mother. Problem solved!”
“You are serious about this, aren't you?” Terry asked with surprise.
“Of course! Plus, it’ll give you a nice flat crotch for your tight outfits as well.”
“And if I say no?”
“Let's not go down that road again. Look, why not do it just to please your mother?”
Terry turned away from me, deep in thought. I knew he realized that if he did what I asked, he would essentially be giving himself a sex-change, only seeing his manhood for occasional needed bathing. Finally, he just shrugged his shoulders and replied, “Would you like another beer?”
“Yes, thanks.” That was the end of the discussion. Time would tell if I had won another round in the battle to change my boyhood buddy into my dream girlfriend.
Come Monday, I was not sure what to expect, since Terry had been quite cold after the talk of toilet ettiquete. So imagine how I felt when I saw him walking towards me, with his tight jeans showing no sign of male organs, just a flat V creasing into the tops of his legs!
“Have you told your mother what you’re doing?” I asked, barely able to restrain my glee.
“No, I just walked around in front of her a few times wearing snug-fitting panties, so she could see I had complied with your wishes.”
“You know this must please her a lot, since she loves seeing you as her daughter.”
“I know, and I love my mother and want her final days to be as happy as possible. But, she’s certainly not making this easy for me…”
“Maybe not, but I appreciate your efforts as well,” I said, giving his hand a quick squeeze. To my great surprise, Terry smiled and squeezed back!
Later that week, I bought him another gift from the boutique where we got the jeans. I found the same assistant, and though he was disappointed I was on my own, when I said I wanted something for my friend he knew exactly who I meant. With his help I bought Terry another pair of women’s pants, this time in white, which were just as tight as the others. On Saturday I took them with me and presented them to my girlfriend. Mrs. Jones was more thrilled by the gift than Terry, but I didn’t care. With two pairs of tight pants he would be displaying his flat front all the time at school now, so I could enjoy my girlfriend’s feminine appearance even there!
The final exams of the year were upon us, and I ended up doing quite well. Unfortunately, Terry didn’t, I guessed because he wasn’t able to put in the needed work. It never crossed my mind that I might be partly to blame for his poor results! I assumed it was due to the fact that he was spending so much time caring for his mother, and not anything resulting from him not being able to concentrate due to worrying about having to appear at school looking more feminine with each passing day.
At least things progressed quite well on the Saturday night front. I no longer had to prompt special behavior in Terry. He automatically snuggled close to me, even in his mother's presence, gave me kisses without being asked, and in general acted like the female in our relationship. All of this was nice, but I still wanted more.
The next stage came when I got my own car. This meant I could take Terry out on real dates. Naturally, I wanted him to come with me dressed in a sexy top, short skirt and high heels, but he wasn’t ready for that yet. So, the first time I took him out in my new car, we compromised. He wore his tight jeans, a hoodie jacket, and his shoes with the little heels, but this was on the condition that one item would be exchanged for something more overtly feminine the next time. So, after just a few weeks it reached the point where I was taking Terry out with him completely dressed as a sexy young woman! At last I had my boyhood buddy back to where he’d been at the time of the beauty pageant. I was proud to once again be able to take my pretty girlfriend Teresa out to eat or see a show.
The next big change in Terry’s life was bound to happen sooner or later. His neighbors finally found out that the teenage boy was essentially living as a young woman when not at school! One happened to call unexpectedly, and without knocking let herself in shouting, “It’s only me.” Before Terry could hide upstairs he was spotted. At first, the woman did not recognize who the new pretty girl was. But then, when she finally realized it was Terry in drag, Mrs. Jones told her some story about how her son thought he might be transgendered, and he was living as a girl part time to find out if the female life was truly right for him.
Apparently the woman bought this, saying, “As if you haven't enough to cope with already…” But, the damage had been done, and the nosey neighbor quickly told everyone she knew about it. I suddenly had no power over Terry, since his dressing as a girl soon became common knowledge. Surprisingly, it did not change our relationship. If anything, it even lowered his resistance to being seen out in public as Teresa, since he now had the attitude, “What the heck, let them have an eyeful!”
From that point on, I was able to take Terry out his front door, with him proudly displaying his beautifully made up face, womanly chest, and nylon-covered legs ending in sexy skyscraper heels! It had taken a few months, but we were finally getting close to where I wanted to be, despite my ‘girlfriend’ not being in favor of most of the changes along the way.
That summer things were great for me, since I now had the freedom to go out in public with my new ‘girlfriend’ to enjoy the long romantic evenings together, and also the opportunity to take Terry out shopping for sexy new clothes to wear for me! What made it even more perfect was what happened with my family.
First, Mary cornered me into admitting that I was going out with ‘Teresa’ again, after I had been seen by some of her friends with an attractive girl who met her description. Then, I was allowed to skip the annual family vacation and remain home with my sister, who was much more relaxed about my dating a boy than my parents would have been. This freedom allowed me to manipulate some interesting events in Terry's life.
The first thing I did was turn up early the next time Mrs. Jones invited me to join her and her daughter for dinner. Then, while Terry was cooking and his mother was watching TV, I went upstairs, supposedly to use the toilet, but with the real purpose of getting a look at my boyhood friend's room. I had not seen it since the contest, and I suspected it looked very different now.
Once inside I found I was right…the place appeared more like my sister’s bedroom than a teenage boy’s, with makeup and lingerie everywhere! Interestingly, I couldn’t find anything of Terry's…all his male stuff must have been stored away. It pleased me to see his room looking so feminine, and I went back downstairs satisfied that Terry was indeed living full time as a girl.
That evening I drank too many beers on purpose, hoping my hosts would realized I shouldn’t drive home in my condition. Fortunately, Mrs. Jones did insist I spend the night, and with no parents to convince, I quickly accepted.
I slept on the living room sofa, which allowed me to wake up the next morning to the wonderful sight of Terry, dressed in a sexy red and white polka-dot top with a matching ribbon tied in his hair, a tight black skirt and tall, stiletto-heeled pumps, bringing our breakfast to the kitchen table! I imagined that he was my wife and did this for me every day before I went off to work, which pleased me greatly. The most exciting part though was seeing that his fake tits were still in place and his hair was fixed up in the same feminine style from the night before, which meant that Terry looked like a girl even while sleeping!
When he called from the kitchen and asked me what I wanted with my meal, I replied, “You!”
“Don't say that, mother might hear you!” Terry whispered as he walked up to me with sexy sway to his hips caused by his tight skirt and the towering heels on his feet.
I reached under the skirt and stroked his satin covered bottom as I said, “Your mother is still taking her bath, and I would love to have you right now!” Then, several things happened unexpectedly. First, Terry sat on my lap and put an arm round my neck.
“Like this?” he asked with a coy smile as he brought his face up to mine and gave me a kiss!
There must have been something about the sexy outfit he was wearing, because Terry seemed more passionate with his kissing than I could remember. After what seemed like an age, we broke for air.
“How about we go back to my place after your mother has been fed so we can have more privacy?” I asked, hoping to take full advantage of Terry’s unusually amorous state. To my surprise I got an enthusiastic 'yes'! An hour later, a very pretty and sexily dressed Teresa sat beside me as we drove to my house. As I had expected, Mary was at work, so we had the place to ourselves.
“You want me, so here I am,” Terry said submissively as he sat on the sofa.
Now that I had the ‘girl’ of my dreams ready and willing to have sex, I was unsure what to do. I started with kissing, then fumbling inside his clothes. In the end Terry undid his blouse, removed his bra and lowered his skirt. He now stood in front of me in just panties and heels. What a sight!
“Could I make love to you?” I asked tentatively.
“I…I guess. But, how could we do it?” Terry asked with confusion. “I mean, you know what I really have underneath my panties…”
“I’ve been reading on the internet about a way we can have sex by using your ‘backdoor vagina’,” I said hesitantly. Terry was puzzled at first by what I was suggesting, but when I showed him a picture I had downloaded from a website that featured transsexuals having sex with men, his eyes opened as wide as saucers!
I decided to act quickly, before my lovely girlfriend could change her mind. So, I immediately rolled Terry over on his stomach and pulled his panties off. When it comes down to it, getting a stiff penis into a tight hole is not easy, but there was some KY jelly in the bathroom, and with patience I eventually found myself deep inside his bottom!
Terry groaned with discomfort and gritted his teeth as I penetrated him, but that gradually subsided. Then, as I began a slow and steady in and out action, I noticed the groaning turned into a moaning, not of pain but of pleasure! In no time he was pushing his behind against my groin with each thrust I made, and soon we were both writhing in passion. Suddenly, I tensed up and then exploded with a mind-shattering orgasm, filling my girlfriend’s bottom with my seed!
Goodness knows what inspired him, but as I lay there recovering Terry licked my penis clean! As he did so, my erection started to return. My girl saw this and responded by giving me an amazing blow job! Wow, what a turn around! Terry had gone from being a teenage boy who resisted my every effort to feminize him, and had become the sex-crazed girl of my dreams!
“Did my man like that?” he asked as he sensuously licked some of my cum off his fingers.
“How can I say no?” I replied in amazement. Then I added, “What brought that on?”.
“I’m not sure,” he admitted sheepishly, “but seeing you in your boxers this morning, looking so manly, just seemed to turn me on. I suddenly felt like I had to do something to make you happy.”
“Well, you certainly have succeeded there!” I said with a grin.
“I also got to be your first, which must mean something,” Terry said wistfully.
“Yes, it does…that I love you!” I said sincerely.
“Now, don't get carried away just because you’ve had sex with me,” my girlfriend admonished.
“But, I’m not being carried away, Teresa. Ever since the contest, I’ve been in love with you!”
Terry’s expression turned serious as he thought about what I said. Finally, he asked, “Why didn't you say that in the first place, instead of forcing me to become your girlfriend?”
“I couldn't be sure you would accept me,” I explained, feeling more guilty than ever about my actions.
Before Terry could reply, our peace was broken by the front door opening. It was Mary coming home for lunch! I immediately grabbed my girl’s arm and dragged her up to my room and locked the door. Finally, we could relax. That is, until she suddenly realized, “My clothes are still downstairs!”
“OMG, stay here!” I left my love on my bed and dressed quickly before going to the stairs.
“Hi brother, is it safe to come up?” Mary asked with a knowing smile. I could see she was carrying the evidence in her hands! I ran downstairs, took Teresa’s clothes from her, and returned to my room. “You two must really be in love to be at it this early in the day!” I heard her tease as I shut my door.
I was flustered and threw the clothes on the bed, but Terry was the one teasing me now. 'What's the rush… don’t you want me anymore?” he said and gave me a fake hurt expression.
“Hurry and get dressed, and then I’ll run you home!” I demanded.
Terry did get dressed, but waiting in the kitchen for us was Mary. We didn’t have to go out that way, but ‘Teresa’ made a point of going in to say hello. Mary seemed unfazed at seeing my boyhood friend looking like a beautiful young woman who had just been well and truly fucked, which was actually the case! At the same time, Terry appeared totally relaxed as he sat down and casually had a chat with her, I think to make me squirm. And he succeeded!
We didn’t leave till late afternoon, by which time Terry and Mary had discussed everything about the re-invention of Teresa, and even where things might go from there. For the first time I felt that my new girlfriend might have gotten the upper hand in our relationship, and with Mary now in on it, my life could be become extremely difficult.
After that, my sister did indeed enjoy teasing me about my sexy new girlfriend, but not so much because it was actually Terry, who we both knew was not a real female, but more at the idea that I had a girlfriend, period, and had been so secretive about it. Pretty much normal behavior for siblings I suppose.
Terry, however, began taking advantage of the fact that he had the power to manipulate me now. Like the day he came over and made me promise to take him shopping for a new sundress and matching heels before he would satisfy my carnal lust! Not that I minded; he looked lovely in the cotton print dress with a yellow ribbon sash he picked out, which I encouraged him to wear off the shoulder to reveal as much skin as possible! And the new tall, wedge sandals I also paid for revealed his pretty painted toenails, as well as adding an extra wiggle to his already sexy walk!
By the time my parents had returned from their holiday, I think Terry and I had had anal sex five times, and I had gotten several blow jobs from him too! Looking back, we were not very good with our sexual positioning at first, but I did some research on the internet, and by our third session Terry was properly on his back with his high heel tipped legs high in the air. This gave me better access to his rear opening, and in this position I was able to control myself better so I could pump away for what seemed like hours! I also loved the way his glue-on breasts looked so enticing this way, as they sat up firmly on his formerly flat boy’s chest. Then, just as I was about to climax, Terry tensed, arched his back, and came right along with me! I was totally pleased with myself that I had made my boyhood friend come like a woman. And from the expression on his face, I could tell he was happy too. The pendulum had swung back towards me after that, as sex was not just about my pleasure anymore. From then on, I always did my best to make sure that Terry was taken care of as well…that is, if he was a good girl!
After my parents returned, there were not many opportunities left during the summer holidays for Terry and I to have sex at my home. We had a couple of daytime encounters, but my summer job got in the way as much as my family members did.
We did have one last night alone before classes resumed. Fortunately, my parents had plans for the evening, and Mary agreed to hang out with some friends, “so you two horny teens can get your rocks off in private!” Since Terry couldn’t dress up as a girl for school, I decided I would have him be a “schoolgirl” for me at home! I borrowed a costume my sister had worn to a Halloween party, and had him wear his wig in pigtails and not too much makeup, to look more virginal. It was a typical schoolgirl outfit, with a plaid skirt and matching tie, along with a white blouse and knee socks. It wasn’t tight fitting, but ever so sexy…the almost 5” heels on his feet made sure of that! The best part was that aside from some panties, the outfit offered no barrier for sex, as the short skirt flipped up easily, allowing me complete access to my beautiful girlfriend’s ‘vagina’! And, with the house free, I planned to take advantage of the dress’s easy access several times that night!
With that in mind, I had Terry start me out with a blow-job. I did this since I knew it would make it easier to keep from cumming too fast later when we got down to the main event…anal sex! And so, I sat back and enjoyed his lips, tongue and hands caress my manhood. It didn’t take long before I let out with a groan and filled “Teresa’s” mouth with a copious amount of my seed!
While I recovered from the mind-shattering orgasm, I couldn’t help but think how much Terry had changed in just a short time. Once, he was my boyhood pal, but now not only was he my girlfriend, but my lover as well! Just thinking of this helped me to quickly become horny again.
I rolled Terry over and flipped up his short skirt and pulled aside his thong panties, allowing me easy access to my lover’s bottom. Then, I grabbed his ponytail and rammed myself deep inside his ‘boy pussy’! Even though we had had sex this way several times before, I could tell Terry still felt some initial discomfort by the pained expression on his face. However, as always, that quickly went away, and was eventually replaced by a look of sheer bliss! In no time, both of us reached an earth-shaking orgasm, followed by a cuddle in each other’s arms.
We lay that way for a while, until our teenage urges returned and we went at it again. We must have had sex three or four times before it got too close to when my parents were expected home and we had to stop. Still, it was truly a night to remember.
Sadly, on Monday Teresa had to disappear so Terry could attend classes without too much of a hassle. And so, gone was the long hair and the breasts; the heels and makeup were missing as well. I knew I couldn’t push him to dress as Teresa to attend classes, so I had to accept that while in school I would have to put up with my girlfriend looking slightly masculine in jeans and shirts. Even if those jeans required the wearing of panties to avoid bulky underwear lines, and the shirts had a definite feminine edge to them! Terry continued wearing the red jeweled earrings all the time, and when I bought some larger pink ones, he resisted only slightly and then gave in and wore them too.
Mrs. Jones was aware that I wanted her son to become as much of a woman as possible, and I felt sure she wanted the same thing. The toilet seat incident and the transgender story she told her neighbor bore this out. However, even I wasn’t totally aware of all she was doing to change her child. Frail and sick Mrs. Jones might have been, but feeble-minded she was not. It was she who made space for us to spend time together early on. It was also she who first encouraged me to take her ‘daughter’ out on dates. And mainly, it was she who had kept Terry dressing as a girl after the pageant was over. But, what I discovered that autumn completely shocked me.
One time when I was visiting my girlfriend, I learned that Mrs Jones would be needing to spend a few days in the hospital. Before she went in, she took me aside and asked if when I came around to ‘have some fun’ with her daughter, could I make sure Teresa took her medication? She went on to explain how once a day since Terry entered the womanless pageant she made a drink for him, usually tea or cocoa, and dissolved a tablet in the hot liquid. When I asked why not just give it as a pill, Mrs. Jones said it was better if Teresa didn’t know what she was taking, since if she did it might disturb her. I took this to mean the medicine was some sort of nerve-calming prescription, and I quickly agreed to see that she got it whenever her mother was away.
A week later, I was enjoying the freedom of Terry's house with Mrs. Jones gone. After we had our usual round of sex and my girl was in the bathroom cleaning up, I went into the kitchen and made her some hot cocoa which included the pill. Mrs Jones was having a series of treatments, which meant she would be in the hospital for a couple of days over several weeks. I did my best during those times to make sure Terry got his medicine.
It wasn’t until about the third time I was preparing the pill-laced drink that curiosity got the better of me, and I made note of the medicine’s name and looked it up on the internet. To my great shock I found out that Mrs Jones was giving Terry female hormones! I assumed they were originally perscribed for her, but she had decided they would be better used to make her son more feminine.
When I read up on the effects of the pills, I recognised things in Terry that at the time had seemed odd, but now made perfect sense. For example, his voice had never broken, and while I had to shave every day, he still had no sign of a beard on his face. Also, his body seemed soft and without any definition, while mine had become much harder and more muscled.
There were also other, less objective things about Terry that I noticed, like his personality seeming much less aggressive than before, the fact that he could now cry at the drop of a hat, and especially his being turned on by my masculine appearance! All of these changes I now attributed to the female hormones he was unknowingly taking.
And so, to my great delight, Mrs. Jones had begun the next big step in Terry’s feminization, one I hadn’t dared to initiate on my own. Armed with this information, I made it my point to see that Teresa got her daily hormone pill without fail. When I told Mrs Jones the next time we were alone that I knew what she was giving her son, she was at first concerned that I might object to this. I quickly assured her that I was in complete agreement with what she was doing. Further, I had done some research on transgendered boys who were taking hormones, and had concluded that Terry’s body could stand an even higher doseage, which would cause it show feminine improvements much faster!
Mrs. Jones was thrilled to hear this, and she decided that since she had plenty of pills to spare, we would increase the number her daughter was given to three a day! And so, Terry began taking triple the amount of female hormones as before, and the results were noticable in just a few months!
I knew this because when I asked him what he would like for Christmas, Terry mentioned some new jeans, because for some reason, the old ones were getting loose in the waist but tighter around the hips and buttocks. Sure enough, when I took a descrete but careful look at my girlfriend’s behind, it was indeed more full, rounded and womanly in appearance!
Even more exciting to me was something that I noticed about Terry’s chest one day at school when he wore a tight t-shirt. It was obvious from the way the front was pushed out by two small mounds that his shape was changing there too! At first I teased him by asking if he’d been working out. When he asked why, I pointed to his developing pectorals and touched one, which made him flinch.
“Tender?” I asked innocently.
“Very!” was the reply. The next time we were alone in his bedroom, I asked Terry to remove his bra and falsies so I could get a better look at this latest change. Sure enough, his normally flat boy’s chest now featured the small mounds of a young girl just beginning to develop breasts! Mrs. Jones was delighted when I told her about these observations, and I suspect she increased the hormone dosage even further after that, since Terry reported his chest seemed much more swollen and tender in the coming weeks!
By Christmas, I had come clean with my parents about my love for Teresa. At first they were extremely skeptical about such a relationship. They had seen my girlfriend growing up as a boy named Terry, and they felt there was no future with a person, no matter how pretty, who demonstrated such obvious sexual confusion. I quickly reassured them that the former boy was handling his change of gender well, and that he looked even more realistic and natural now than at the contest. Finally, it was decided that I could invite Teresa to visit over the Christmas break.
As it turned out, my parents were as taken with the beautiful and feminine creature I had created as I was. In fact, after my mother got to know Teresa better, she invited her and her mother over to join us for dinner on New Year’s Day, which made Mrs. Jones as happy as I’d seen her in the last few months.
As Terry got better known around town as a transgendered boy, his freedom to be publicly feminine grew. However, for school he had to maintain a somewhat boyish appearance, and I counted the days until we graduated and Teresa could be a full-time female.
The hormones continued to do their work, and by Easter the small mounds of Christmas had grown into actual breasts, preventing Terry from wearing any tight-fitting top to school for fear of becoming even more of an object of ridicule. Naturally, he worried about the changes to his body, and even asked his mother to take him to see a doctor. But Mrs. Jones explained honestly that they didn’t have the money to do so, and then she pointed out that she’d seen some boys develop small breasts right before they were about to begin puberty. Hearing that, Terry felt relieved. He had wondered when his body would start becoming more masculine and hairy like the other guys his age, and now he had hope that the time would be soon. Little did he know that the changes he was hoping for would never happen!
In the meantime, I tried to make Terry more accepting of his new feminine attributes. Whenever we made love, I always took care to gently fondle his breasts and squeeze his swollen nipples, showing him how pleasurable they could be. When he got used to that, I moved on to licking and sucking on them, which soon had my girlfriend begging for more!
Using this tactic, Terry began to expect and enjoy my playing with his breasts as a part of any sexual encounter we had. He especially grew to love my hands on his growing mammary glands whenever we had anal sex, and he would cry out for me to squeeze and pinch them as I pounded his behind with my engorged organ!
By the end of the school year, I knew I had done well enough in my courses to graduate and get a good job. For Terry, it was completely different. He failed all but one course, home economics, but there was no way he could redo his senior year now that his body had changed to the point where he needed to wear a bra at all times to support his growing breasts! So, he never went back to school after that, and just stayed at home and looked after his mother instead.
Over the course of the summer, to my great delight, Terry’s chest developed to the point that he completely filled his old bras. Also, his expanding bottom looked even more sexy as it jiggled in over-tight jeans and skirts. During this time our relationship seemed to settle down to one of an established couple. With my good-paying job and still living at home, I had plenty of money, so I regularly gave Terry expensive gifts, either to wear for me or in some other fashion make himself look even more feminine and sexy.
While I was generally enjoying myself, things weren’t going as well for Mrs. Jones. And then, early in the fall, she lost her fight to live. It was a sad day when I escorted her beloved ‘daughter’ to the funeral. My dad had been very good and arranged everything, but I remember a hard discussion between Terry and my mother about whether he should go to the funeral as the boy he was born or the girl he had become. He wanted to do the former, since relatives would be there who would be confused by his new feminine appearance.
My mother resolved the problem by taking Terry to a full length mirror and asking him what he saw. He had to admit it was a woman. “So how could a woman go dressed as a boy and not look odd?” she asked. “Let those others who never bothered to visit while your mother was sick think whatever they want to. Their opinion isn’t worth as much as their help during the past few years would’ve been.”
And so, Terry went to the funeral as Teresa. My mother took him out the day before and bought him a nice black dress to wear. It was tasteful, but low cut enough to show off his now impressive cleavage. While some at the funeral were confused about who was leading the mourners, no one guessed that the weeping person was anything but an attractive young woman.
After his mother was laid to rest, Terry felt lost with no one to care for and no school or work to go to. He sat at home and tried to consider his future. I was over there a lot, though not for any pleasure of my own. Rather, I was just looking out for someone I loved dearly.
Often, I would find Terry sobbing over the loss of his mother. And, on one occasion I found him standing naked in front of a mirror, staring at himself and questioning what had become of the boy he once was. I knew then it was time to act. Terry’s grief would surely lessen over time, but his doubts about being anything but a girl, my girl, I could not allow to grow!
And so, insisting that he shouldn’t mope around any longer, I took Terry to a salon and arranged for him have a complete make-over. I told the beautician to give my girlfriend ‘the works’! I was told to come back in four hours, which I thought was a little long, but I agreed. When I returned and Terry was finally finished with his make-over, I was amazed at the difference!
I was used to the wig he always wore, but that was gone. Terry’s own hair had apparently grown rapidly from the female hormones, and had been fashioned into a totally feminine style. His eyes had lash extensions, making them extra long and silky, his brows altered permanently into pencil-thin high arches through electrolysis, his lips plumped with collagen, and after many failed attempts to get him to grow more feminine-looking nails, he now sported long acrylic nails painted bright red!
I was a lot poorer, but extremely pleased that I had talked Terry into doing this. It really made a big difference in his personally. And when we got home afterwards, for the first time since his loss we had sex! I even had the nail marks on my back to prove it, though I wasn’t complaining.
My father offered to help sort out Terry’s finances, and it quickly became clear that he had no income at all now that the medical assistance and pensions were gone. He did inherit the house, and if he went back to finish school he could get extra support while studying, but it would not be much. So, I offered to help by moving in with him and sharing the costs. This was viewed differently by everyone. My dad thought I was a fool, my mother thought me generous, and my sister thought I was after sex! I think maybe all three were right.
Terry did not really get a say in the matter. I still saw him as my girl, and so I was the boss. So, I just moved in. He didn’t complain, though, about my unilateral decision, because besides helping him financially, it also gave him someone to look after and a purpose to doing things about the house, which helped heal the grief over losing his mother. For my part, I was thrilled that I now got to see “Teresa” every evening, which was a delight since I have always loved Terry in sexy nightgowns, of which I made sure he had plenty!
A few things had to change though. Terry was uncomfortable sleeping in his mothers double bed, and his single was too small for the two of us. So we redecorated his room and bought a new bedroom set. But in the choosing of colors, I could tell he was undecided between pinks and flowers versus darker greys and more masculine designs. I was disappointed to see that despite my imposed femininity all these many months, Terry still had a part of himself which yearned to return to manhood.
My solution was to take him out and get his navel pierced and fitted with a medalion that had 'Brian's Girl' written on it! I made sure the belly ring was impossible to remove without a special key which only I had, so Terry would have a permanent reminder of who he now was. After that, we returned to the decorators, and a week later Terry had pink walls, lacy curtains and a canopy bed! The former boy’s bedroom looked very feminine now, and totally Teresa’s. When we christened the bed that night, I loved seeing Terry wearing the new navel jewelry, telling all the world that he was my girlfriend!
Without any new pills from Mrs. Jones, I eventually ran out of hormones. I decided to take a bold step and come clean with Terry about what his mother had done. I defended her by saying that she started giving him her female hormone medicine because she wanted her daughter to have a beautiful figure to go along with her lovely face.
Terry was shocked and angry at first over what his mother had done to him. Then, he calmed down and actually felt relieved that he now understood why his body had become so feminine looking. He had thought he might have testicular cancer, which was blocking his male hormones and causing the changes, so at least he didn’t have to worry about that any more.
Then, he put his head on my shoulder and began to sob, crying out that he forgave his mother since what she had done just made it easier for her to enjoy the daughter she always wanted for her final few months of life. In his weakened emotional state, it was easy to convince Terry to see a transgender specialist named Dr. Mills, who after hearing how long the teenage boy had been living as a woman, promptly put him on a proper regime of female hormones and testosterone blockers to insure he continued his feminine development.
During our visit with the specialist, the subject of eventual sex reassignment surgery came up, but Terry wouldn’t hear of it. I spoke to the doctor in private and explained that ‘Teresa’ was still recovering from the loss of her mother, but I assured the surgeon that she had expressed many times before Mrs. Jones’ passing that her ultimate goal was to become a woman so she could marry me. The specialist understood and said that the surgery could be scheduled at some future date whenever Teresa was ready.
As we left Dr. Mill’s office, I was dancing on air! My ultimate goal of turning my boyhood friend into a complete woman was within my grasp. Now, I just had to find some way of convincing Terry to agree to having his sex permanently changed!
Things went along well after that. I got a nice promotion and increase in salary at my job, and Terry went back to school and finally graduated. When he was ready to look for work, he thought about doing it as a male, since his ID’s all showed him to be one. However, I found a job for him that didn’t require an ID and would pay him ‘under the table’, so there was no need to report wages to social security. It was in an assisted living home for the elderly, something Terry knew how to do quite well. So, to their and my delight, the residents of Golden Acres soon had a pretty new assistant named Teresa to help them!
There was one potential problem on the horizon. The transgender doctor had insisted on Terry having counseling to ensure that becoming a female was what he truly wanted. Naturally, I worried that it might undo all the mental and emotional feminizing I had done to him up till then. And so, before and after each counseling session, I made sure we had sex, taking particular care to see that Terry had a mind-blowing orgasm each time! It must have worked, because the doctor told me that ‘Teresa’ never expressed the need to be a boy again.
Despite this, the subject of sex change surgery was still forbidden at home. As time past, Terry and I stayed as boyfriend and girlfriend, while I had to watch as most of my friends got married. This irked me, because as two males we could not be joined in wedded bliss. So, I hatched another plan.
First, I convinced my family to go with us on a joint ski vacation. I had done my research and the hotel we were staying at would be hosting a ‘womanless’ wedding! Terry knew nothing of this until we got there and saw the posters and preparations for this event. I 'innocently' suggested we could volunteer to participate, because technically he was still a male. Terry was reluctant, remembering what happened the last time he entered a ‘womanless’ event!
Mary did her best to convince him that it would be fun to go shopping for a wedding gown together if he was chosen to be the bride, but he still hesitated. In the end, what made Terry agreed to sign up was my pointing out that we probably wouldn’t be selected anyway, since we were not local people. Little did he know that I had arranged with the sponsors beforehand that I would provide our wedding clothes for free if we were chosen to be the bride and groom!
And so, we signed up for the event. It was amusing to see Terry try and dress up like a boy, binding his breasts, covering his long hair with a cap and wearing loose fitting unisex clothes to hide his narrow waist and wide hips, all to no avail. He still looked every bit as feminine as any real girl would have. His male gender would surely have been questioned if it weren’t for the fact that I had showed the sponsors his birth certificate beforehand when I was arranging things.
I didn’t see much of Terry for the two days before the womanless wedding. He and Mary spent most of the time shopping for his wedding gown, matching heels and associated lingerie. Also, the night before the ceremony my sister insisted that Teresa stay in her room, since it wasn’t right for an unmarried couple to sleep together before their wedding!
Finally, the big day arrived. A local church had offered the use of an empty chapel for the event, since it was to raise money for charity. While we waited for the bride, my parents and I looked over the other participants in my ‘wedding’. I noted with amusement that they were obviously all men, even the bridesmaids! Meanwhile, Mary was helping ‘Teresa’ to get ready, and I was certain when she was done no one would mistake my bride for a man!
Sure enough, when Terry appeared, he looked gorgeous, dressed in a long white ruffled gown and a thin veil which did little to hide the beauty of his face. Everyone cheered when he made the traditional walk down the aisle, and I’m sure more than a few doubted it was really a boy underneath the dress, especially when they noticed the ample cleavage he displayed!
In the following hour my bride and I did the vows, the exchange of rings, the first kiss, the signing of a register, and then later the first waltz as man and wife. When we went back to our room afterwards, Terry had on my wedding ring and was carrying a certificate which said we were legally married. Unbeknownst to him, the person officiating at the wedding was an ordained minister, and the certificate was authentic! Terry didn’t realize it at the time, but when he said, “I do,” he was really becoming my wife!
I called him “Mrs. Smith” as I helped my boy-bride out of his wedding gown, causing him to blush sweetly. While doing so I explained that in taking my name he now had to completely accept my authority, due to the honor and obey part of the vows. Looking fantastic in his sexy white wedding trousseau, Terry glanced over his shoulder with amusement at this comment. Then, he replied, “That might be true, Brian, if the wedding wasn’t all just a sham.”
“To the contrary, my dear, the wedding was real and you are actually my wife now!” I then explained about the minister and license being authentic.
“But, how can that be? I’m still really a male and my name isn’t Teresa as it says on the marriage certificate,” Terry pointed out.
“You didn’t realize it at the time, but among all the papers you had to sign so the doctor could put you on hormones was one to legally change your name to Teresa, and another to make your sex officially female on your new birth certificate. In the eyes of the world, you are now officially a woman and my wife!”
Hearing that, Terry suddenly felt faint, and he had to sit down on a chair for support. As the reality of the situation sank in, he groaned, “This can’t be happening. I mean, I’ve still got boy bits hanging between my legs!”
“That’s another thing I wanted to talk to you about,” I admitted sheepishly. “The real reason I chose this town for our wedding was that it is the home of a world renown sex change surgeon. In fact, I made an appointment for you to see him on Monday!”
Terry’s eyes went wide with shock at hearing this. Then, his shoulders slumped, and with a tone of deep resignation in his voice, he said, “I should have fought you years ago, whether it was in entering the womanless beauty pageant, wearing the red stud earrings, or even the toilet seat charade. But, I didn’t, and now I am what you made me to be - Mrs. Teresa Smith! I guess I might as well see this through to the ultimate end that you seem to want so much…”
I picked Terry up and carried him to the bed. As I lay down beside him, I said from the bottom of my heart, “I have loved you ever since I saw you dressed and made up as Teresa for the first contest…maybe even subconsciously before then, I don’t know. However, what I do know is that I will be for you the best husband any wife could have, and I will do everything I can to make your life as a woman as happy and fulfilling as possible!” Then, I kissed Terry, long and hard, and by the time the kiss had ended, it was Teresa who was kissing back!
This was made official one week later when Terry entered an operating room as a boy, and left as a woman, complete with everything but ovaries! I still could not believe that I had actually made this happen, as I checked Teresa out of the clinic and helped her carefully sit in the front seat of my car. I knew we wouldn’t be able to have sex for several weeks, but the satisfaction of knowing that beneath those bandages was a vagina and not a penis and testicles was consolation enough.
As we drove home, I couldn’t stop smiling. I had converted my boyhood friend, Terry, into my dream girl and wife, Teresa, and our future together looked bright! Suddenly, it occurred to me that we couldn’t have children together. I had always wanted to have a son who I could teach to be a man, and a daughter I could spoil and make into a “daddy’s girl”, so this was a big disappointment.
When I thought about it, though, I realized that I could have the children I desired through adoption, or even by using a surrogate female implanted with my sperm! Having resolved this issue, I relaxed and pictured my new wife breast-feeding our baby. I know when Terry was still a boy, he could never have imagined that one day he would have an infant suckling at his breast, and I worried if he’d be willing to do something so femininely iconic. But then, when I turned and looked at my wife and saw the deep love for me in her eyes, and I knew that it would happen, just like I wanted.
The end
Schools like to think they are preparing their charges for the world outside the classroom and for many years have been making the students get a taste of what they might like to do once they leave the education system.
Joe enjoys the taste and can't stop going back for more
Joe was struggling at school, he was not that academic, he was not much good at sport either, well who wants a spindly short kid on their team, he was good with his hands and got along well with people around him, so life was not too bad. Still he was proving a difficult child to place for work experience. Now he was sixteen and in his last compulsory year of school it was in the timetable that for at least one week every child in that year gained some experience working in a job he or she felt might be something they would like to take as a career. Joe had no ambitions though, he just wanted someone to tell him what to do, it was that simple for him, as long as he could do whatever was asked of him, he was happy.
As always the school was short of places to send their students and rely on the good will of parents and relatives every year to find opportunities for some students. Joe was one such child, and as a consequence of not specifying a career he ended up spending a week at a job his mother had come upon.
Kutz, was not the first thing Joe had on his list of possibles, but Kay was a friend of his mother and did in fact need a bit of help at the time, so it seemed like a good thing when everything was sorted between school and Kay. Joe was to start the week before half term in February. He was not ecstatic but it was better than school.
His first day was spent sweeping up and making drinks for the customers. His easy manner made him a hit with Kay who liked him straight away. Kay also had an odd sense of humour and liked to tease people to see what reaction she got. Joe would be no exception, at the end of Monday she gave him a pink tabard and told him he should wear it the next day to keep himself clean, just like Denise and herself did. Joe asked if she was sure, she said yes, so when he got home he asked his mother if it seemed right for him to wear the tabard. He showed it to her and realising he was being teased, so she decided to play along with it and say that if Kay wants him to wear it then he should.
The next day when he got to work he put the tabard over his clothes and started working. Kay could not help herself and smiled as he wiped down the work stations. Then she thought what else could she get him to do.
It was slack in the middle of the morning, so after they had had a coffee, Kay suggested that it would help Joe to understand what the customer experience is like by letting her or Denise do some of the treatments on him that they did on the customers. When Joe asked what sort of treatments, because he was thinking big hair does, she reassured him by offering to wash and dry his hair. No harm in that he thought, he did it himself at home anyway. So for the next half hour Joe's hair was massaged, shampooed, conditioned and then blow dried. He especially liked the washing and massage, but when she had finished drying his hair he felt rather conspicuous. Gone was his rather ordinary boy look, now he had a straightened fringe gelled across his forehead, the back of his head was a mass of spiky randomness. When he was asked if he liked it, he was diplomatic enough to say it was different and might take some getting used too, but yes he liked it. 'Super' said Kay and told him he should continue with his learning by doing it himself the next morning before he came to work.
This was a little harder to work round, the tabard was just in the shop, the women knew he was a lad and they only had pink tabards, so that was nearly ok. But his hair was for outside and not an easy thing to disguise, then he remembered his hoodie. His mum was a little surprised to see him home Tuesday night sporting a new style but flattered him as much as a teenage boy can be flattered. And when he said he had to do it for work in the morning she offered to help.
So Wednesday morning he was up early to replicate the style Kay had shown him, and with his mum's help did a reasonable job of it. Kay was full of compliments when he arrived for work, a little disappointed with the hoodie, but then quietly had a word with Denise over 'how far will he go?'
Neither was sure just how far they could push him until he said no, so waited till there was a lull and brought up the subject of experiencing what the salon has to offer. Joe did ask what else they could do, he had had a wash a blow the day before. Almost before he had said it he knew there was so much more that they did, Kay and Denise picked up a treatment menu. Colour. Permanent wave. Extensions. Cut. Styling. That was without turning over to the nail and beauty treatments they offered. Joe felt a little uneasy and asked what they had in mind, but had turned it around as Kay offered to do anything he chose. He had seen some women under the big hoods as he gave them coffees, but not knowing what they were for, but thinking it would be interesting to be in one, he asked if they would let him have a go in one. The two women looked at each other and in unison said 'yes'.
Joe was shocked when they did not just wash his hair, but wetted it, then wrapped his hair around curlers until his scalp hurt with the pulling of the hair. Then sprayed with something else and he finally got to sit under the hood. He was given a coffee and a cosmo to read. But after a little while Denise came and took a hand and started to file his nails, then she did the other. Nice and neatly rounded tips he now had, then to his horror she pulled out a bottle of varnish, he was stuck under the hood and could not get out, but soon relaxed when he saw the varnish was clear and not a bright colour like the woman who had been in first thing had chosen. Finally the hood timer clicked off and Joe was lead to the styling chair. A lot more spraying and brushing and drying was to happen before Kay was finished. Now the straight fringe was gone, now his hair flicked up all over his head, the opposite to curling it all under. The beauty of this treatment Kay told him was that it would not take as much to get it looking right in the morning as the products would hold the style overnight. He was not sure if that was a good thing or not. Worse was to come though, for the first time he was called miss by a customer. Then when he got home his mum told him the style was great but maybe a few highlights would make it better, then she saw his finger nails and told him he was supposed to be working not being pampered by Kay and Denise.
Thursday and Joe was not sure what to expect, his hair was still looking Ok even when he got up and a quick brush brought it back to life. But then as he left the house he overheard his mum on the phone saying 'that will be fine with me, just check with him though'. It was almost the first thing Kay said when he walked into the salon 'your mum thinks we should highlight the ends for you' Joe admitted she had said as much the night before but was not so sure about it himself. Kay managed to twist it around and somehow he agreed to letting her do the highlights as her choice this time, then next time he could choose. By dinnertime he had blonde tips on his flicking out bits, and even he agreed it did bring out the style. Kay could then say 'now your turn to pick'. Joe just thought 'what do I pick, none of these things are really for a lad' but then as he looked down the menu he saw the waxing and thought 'girls make such a fuss about it why not try it and find out for myself'. 'Waxing please' said Joe, 'Oh' said Kay 'best come this way right now before you change your mind'
Joe could not believe how painful it was, and off course it had to be quiet just at that moment, so when his arms had been done, Kay said they might as well do the rest of him and give him the full treatment. The moisturiser was a lovely massage to recover with though. His mum was getting to expect something new to have happened to her boy while at work now and asked what he had experienced that day. When he lifted the hood of his head his mum let out a little whoop, 'I knew it would look great', 'Also got myself waxed' 'what......all over?' 'yes, feels a little odd, all my clothes are so rough, my skin is like super sensitive'. While the tea was cooking she took him up to her room and gave him a silk 'shirt' to try on and some soft cotton trousers, luckily they were about the same size so he fitted the new clothes well enough, and enjoyed the softer fabrics on his skin. That night she gave him some satin pyjamas to wear, he was about to say 'mum' in an exasperated teenage manner, but she just cut in with 'I was right about the shirt and pants, just try them' he accepted but did manage a resigned 'but pink!'
For work on the Friday his mum got him to wear a soft cotton top, not unlike his normal t shirt but a lot softer, three quarter sleeves that he did not realise until later as they kept riding up after every time he pulled them down. And under his jeans some tights to lessen the rough texture of the demin. He was in the locker room putting on his tabard with Denise and Kay, when they saw the white top. 'That's nice' 'my mum lent it me, my skin is so sensitive now' 'looks lovely' said Denise 'just perfect' said Kay. The comments made Joe think this was not perhaps the look he would have chosen on Monday just gone, but then when he heard the first customer say to Denise 'could you ask the girl to fetch me a coffee, white no sugar' it took a moment for it to register that she was talking about him, moments later Denise spoke 'Josie, could you get Mrs Whirle a coffee dear'. All he did was mouth 'Josie' back and go to make the coffee as requested.
During the mid morning lull they were having a quiet drink together, 'so the last day of your week with us dear, have you enjoyed it?'
'It has certainly been an experience'
'Well if you want, I would like to take you on part time till you finish school, then as an apprentice after you leave school' offered Kay
'Oh er, thank you'
Kay and Denise went on to explain how they thought he had the right attitude to the salon world, good with customers, able to do the tasks required, and happy to make the most of himself using the beauty treatments, adding in a dismissive way 'even barbers are well groomed'. The clincher though was to get paid for his week and asked if he would work the next week as it was half term.
'Excellent Josie'
'Josie?.....please don't tease me' Joe replied
'but it suits you. especially in that top of your mothers. Come here and look in the mirror...........now tell me what you see, a butch lad, muscles bulging out all over the place, or a slim girl who looks a little like a boy'
'but I am a boy, I still look like me, well almost'
'we have not done that much, new hair and you have some different clothes on, but you are really the same slim person you were before just looking a little softer now'
'softer, more like a girl you mean'
'if you want to say so Josie, we can't disagree'
Just then the door opened 'Ah Kathryn, good morning, come for your wash and style this morning, manicure as well, going somewhere nice tonight.' then turning to Joe 'Josie would you take Kathryn's coat'
And that was it, Joe's name for the rest of the day was Josie, much to the amusement of Kay and Denise, and to the apparent acceptance of all the ladies who came through the door who referred to him as a her. One even commented that Joe was not made up like so many young girls these days, Kay replied that after a week with them Josie was a lot improved on what she was a week ago.
Because Alison and Dorothy asked.
A further dip into Joe's introduction to work.
Message for Stan, Joe only lives in my head, don't worry about him I will keep him safe.
Joe would tell you that something changed in him that day, being taken for a girl was weird at first but not the first time it had happened, it was the first time it happened consistently though, so he just fell into playing the role of Josie. It did not come as a surprise on reflection really when Kay asked if he wanted to try one last treatment as part of the work experience, he looked at Kay's neatly manicured oval nails and asked what it was like to have long nails. 'Don't even think about them now, they make my hands look better than with short nails I think' then turned to look at Joe 'why do you fancy some?'
'was just pondering the idea'
Kay stepped in quickly 'they would look good on you, but they are not just for a day you know I would expect you to keep them on till you go back to school.' Then added 'If I do them I will expect you to work next week for me as Josie'. Joe took a deep breath, this was a rather big step that he was consciously taking,
'yes please, and I thought I had said I would work next week'
'Not as Josie'
'Oh I see' Joe said slowly, but he was admiring Kay's nails and thinking what it would be like to have his own 'as Josie then' Joe confirmed.
Kay told him to ring his mum and tell her he would be late home. He did ring but only told her he was trying out another of the salon's services. She was intrigued but happy to wait and see what he came home with on his last day at the salon.
She was waiting but trying to look busy with the meal. Joe came in with hands in pockets, hood over his head feeling rather conspicuous outside of the salon. Not wishing to appear eager she calmly said 'Your tea is on the table in two minutes' Joe went to his room and removed the hoodie, he stared at his bare hairless lower arms, then at his hands with there now enhanced nails, they were only half as long again as they were before Kay started fixing the acrylics to them, nothing like the really long ones Kay sported, but with the hint of pink on them it would be a mistake to think of them as boys hands, and yes they did make his fingers look longer and more delicate. His mother noticed striaght away, 'let me take a look' she admired 'they do look nice, what sort are they?'
'Acrylics'
'Oh, they take some removing don't they'
'Yes but I can't wash hair with anything that might come unglued, these are bonded to my nail Kay says'
'But you finish today don't you?'
'No, been asked to work next week'
'That's good, well I guess so. Rather makes you feminine looking you know'
'Yes I have noticed, but I was getting called Josie anyway so thought what the heck, and I wanted to find out for myself what long nails are like'
'What do you mean Josie'
'Ever since I had my first hair cut every now and then women called me a girl, and you must remember those times when we have been out and they called me your daughter. Well it got more frequent after I had the highlights, and then I reckon your top did nothing but help that. I have been called Josie all day today.'
'You fine with that?' she was getting concerned that her son though encouraged by her Denise and Kay was becoming the main mover in what had just been fun teasing till then. 'and do you plan on being a girl next week?'
'don't worry mum, it is only for a week, I can't go to school like this can I'
'Just for a week, then?'
Joe then went on to tell of his news that he had been offered a job starting when he finished school and on the Saturdays till then.
'What are you doing tomorrow?'
'I was going to have a lie in, I am knackered'
'Just thought you could spend your wages on new clothes instead of borrowing mine, TK Maxx and Primark will be open and cheap'
After his Sunday lie in he dressed in the blouse and trousers his mum had lent him the day he had been waxed. His mum had grown used to the idea of a girlie son by the morning and happily went with him shopping. Initially nervous, Joe relaxed as they browsed the rails, eventually being brave enough to use the changing rooms. He came away with four tops, three were like t shirts, but with longer sleeves and different styled necks to his usual, one top was a blouse, buttons up the front, small collar and little cap sleeves in a shiny black, no way was that anything but a girls choice his mum said. A pair of tight jeans with a waist band on the hips and some plain white trainers completed his new look.
Once home he changed and gave his mother a bit of a show of what he had bought, ending up wearing the black blouse for the remainder of the day.
'So do you like being a girl?' his mum suddenly asked
'I am not a girl, I just look like one'
'Whatever, do you like it, the extra time needed to get ready, the cleaning of the make up'
'I like taking a bit of care about my appearance if that is what you mean'
'And what else can I expect to see you doing next week at the salon?'
'Not sure what else Kay or Denise would like me to try'
'Oh I can think of lots, just don't let her make you do anything you don't want'
'Been a good experience this, and I know she was teasing me but it is good to know how the customer feels, yes'
'Well if you put it that way, then yes'
Monday when he would in the past have just lounged about all day as it was a holiday, he was up and ready for work, a grey top, new tight jeans and trainers, hair brushed and gelled, eye lashes enhanced and though his mum had not commented some of her lip gloss on as well.
'New clothes?' Kay asked
'Yes can't keep borrowing mum's'
'that is true, and the nails, any trouble?'
'A little awkward at first but no trouble, been fine as long as I remember'
'I think me and Denise will have to think what will be your next experience'
'It's fine, I am just happy like this, no need to put you to any trouble'
'No trouble, and besides we want you to learn what it is like being the female client in a salon, so you can treat our customers better'
Joe was wondering what she meant by all that, but needed to get on with his cleaning jobs while Denise restocked and Kay did some book keeping.
A slow morning and about eleven there is no one in so Kay invited Joe to take a salon chair. It took one pull for Joe to realise what she was doing, plucking his eye brows. 'Just neatening up the lines, and letting you know how it feels, hold still while I get the next one' A few minutes later 'there nothing much different, just neater. Take a look' Joe could not see a big difference but they did look more defined. He thought the plucking would not be noticed but that evening his mum gave him a good look over and commented on how nice his brows were, then asked for her lip gloss back. He picked it out of his hoodie pocket and returned it. 'You can keep it, but next time ask, I spent ages looking for it this morning and ended up buying myself a new one at lunch time' Joe apologised and asked if he could have a play with her cosmetics to see what does what.
That evening the two of them spent their time going through Joe's mother's make up, she would show him a product, he would then try applying it to himself. He was amazed at how much he could change his face with the use of colours, he particularly liked the lipsticks that were near his own colour but added some depth and sheen to his own, his other delight was eye shadow, especially the pale ones giving just a hint of colour next to his long blackened lashes. That was also the day that regular moisturising became part of his daily routine along with cleansing.
Tuesday, and he is wearing a lemon top, and after his time the night before, a pale glossy pink lipstick.
'My word Josie, you are looking more pretty every day now' Denise commented, Joe unused to such comments, blushed.
Kay came in and agreed with Denise, then added 'I think today it would be good if you found out what it is like to have a piercing. Anywhere you fancy?'
Joe a little wrong footed suggested an ear as he had thought of getting one ear stud for a while 'ears have to be in pairs' continued Kay. After a moment, Joe agreed and it was arranged that Joe would take a trip to a nearby shop that did piercing while he was out getting the lunch order.
It all got a little confused as messages got passed from Kay to the shop, and when Joe turned up they were expecting him, well her really. The confusion lay in the way Kay had said pair, so Joe braced himself for the first stud, which he was surprised by how little it hurt, and then not knowing what to expect thought nothing as the girl continued to attend to the same ear, it was as the second hole was made that Joe questioned if they had got it right, he was expecting a pair to be one in each ear not a pair in each ear. The girl got all flustered and asked Joe not to complain, he then explained how Kay had said girls wear there piercing symmetrically, to which the girl offered to match the other ear at no extra cost. Joe was not sure if four studs would look right, so she swapped a stud for a ring sleeper and everything was sorted, at least for the girl. When he got back to the shop, Kay noticed right off and asked why he he got carried away, so he explained it was not meant to be, Kay just said 'oh right' in a knowing tone. It was when he got home that his mum made the biggest fuss, he tried to argue that boys have pierced ears, 'not two in each ear' his mum insisted, Joe just went to his room saying, 'well it is done now, she said don't remove them till they have healed, so that is it, I am stuck with them even if you don't like them'
Thanks for your comments.
Here is Joe gently being teased into a different style of dressing.
Wednesday and his ears are throbbing a bit, but now he has got used to them he is getting to like them and wonders what he will wear when he can change them. At work Kay asked if he liked his ears, he told her he was getting used to them, then she retold a conversation she had had with his mum the night before, where his mum had accused her of influencing him and his style. But as far as Kay could tell, the tabard and first hair styling, maybe the second were her doing as part of a tease, but from then on it had been Joe who she felt was driving the choices, even his mum had suggested the highlights. Kay finished with a question 'do you feel I have pushed you into any of these treatments, and have you felt it wrong of me to do anything to you these last few days?'
'Not sure I liked the tabard at first, but I have seen it as part of the experience, and I am getting to like making myself look better, and it is good to see how life is from the other side, isn't it?'
'So you have no problem looking like a Josie rather than a Joe?'
'Still not sure about the name, but no I don't mind being Josie while I am here at the salon'
'Till Saturday then I look forward to seeing Josie, but maybe we had better cool it a bit with the feminine stuff, for your mum's sake'
'Maybe' was Joe's short reply.
Kay just kept eye contact and smiled at the ambiguos reply.
Things were frosty when Joe got home that evening, ending up with him stating that he liked looking pretty and being taken for a girl. Rather said as a teenage reaction to her ringing Kay than any real desire to dress that way, but as many know, if you tell a teenager no, then that is what they will do. So come Thursday morning while his mum is in the shower he is at her vanity unit giving himself a full face make up, foundation, blusher, stronger eye shades, brighter lipstick. And then before she could say anything he was out of the house and off to work. Kay saw him first 'does your mum approve?'
'She doesn't know'
'I see, well come inside and lets just take a closer look at what you have done' Kay then took five minutes toning down the roughly applied cosmetics explaining what she was doing as she did so. When finished the make up looked far more natural and Joe felt more comfortable. Though what his mum would say when he got home was another problem.
His mum was rather relaxed about the made up face when he got home, and just asked about his day at the salon, not wanting to exacerbate his teenage rebellion. But before they went to bed, Joe was downstairs in his soft pink pyjamas, she suggested that she help him in the morning with make up if he was going to do more than a lip gloss, Joe not sure what to make of this U turn, managed a 'oh right, thanks' in reply. But come the morning felt able to sit beside her while she did her face and accept tips as he did his own. That morning he decided to wear the black blouse because he might never get another chance. Kay just summed it up when he got to work 'very pretty Josie, I tell you Joe is disappearing a little bit every day now, but one day left then it is back to school'
Saturday was a bit of an anti climax due to there being a constant stream of customers and no chance to enjoy the last day being called Josie. If Saturday was dull, Sunday was a real down. First he had to take the highlights out of his hair and try to get it back to a pre work experience look, which ended up looking scruffy, the make up was easy but the nails took an awful lot of filing to reduce the depth of added nail, and then there were the four ear piercing, as he understood it he could not take them out, so they had to stay at least for another three weeks. His hope was they would be seen as being 'cool' and not sissy by his mates.
Over the first week Joe got used to being Joe again, he was proud of his news that he had been offered a job when he left school, but some made the connection between a job in a salon and the studs, luckily Joe was confident enough to brush them off and tease whoever was making the comments.
He was back at work the following Saturday, as Joe really, his hair was wrong so he opted for a plain look which got a disappointed reception from Kay. Joe promised to try a little more in the future. So for the weekends he started to blow dry his hair into a style something like he had had before, and would wear light make up and his female tops to work, this clearly met with Kay's approval who clearly preferred Josie to Joe at work. What was surprising to Joe was his mum was coming back to encouraging him again, at first she had helped him, but then cooled off trying to stop his feminine development, but now with Joe back six days a week she seemed to be looking forward to Saturday and having Josie back. She said he was softer and less bullish, also more helpful around the house the more girlie he was. This change was most clearly noticed when she bought him some pjamas and then pointed out his body hair was returning a few weeks later and bought him some hair remover.
With exams to focus on Joe was stopped from working full time at the easter holidays, but knew that within a few months he would be leaving school behind and starting a job he had enjoyed.
At last the exams were over and Joe started working at the salon permanently. The first thing he did was to make arrangements with Kay so he could fit in better as Josie. This meant a definite change in his appearance she insisted, no switching back and forth between boy and girl. Joe just said he wanted to enjoy the pleasures of the salon once again so he would better understand what the clients were experiencing. It took half a day but by the end Joe would have more trouble being a boy on his way home than cow being taken for a dog. his now blonde hair was a mass of spikes and sculpted fringe, his eyebrows were neat tadpoles, his nails were longer and brighter, and along with his female tops and new 3" hoops and red studs in his ears he looked very much a girl at work. Then to his surprise when he got home his mother had bought him a new white hoodie to replace his grey one and filled his drawers with panties which would not show through his tight jeans. He had expected never to wear his school uniform again, but it was looking more like he would not be wearing any boy clothing at all, after a moments consideration as the penny dropped he smiled and knew he liked the feel of his new clothes more than his boy stuff, so why not forget about the harsh boy things and enjoy his more female things. The decision was made that Tuesday over tea, he asked his mum about the knickers and nightwear, she said it would either get it out of his system or be his way in the future, he said he preferred female clothes and did not see it as something he would give up. So in a sort of ceremony they cleared his drawers of all underwear, school clothes and overtly boy clothing. The end of which left big spaces in his cupboard, prompting the suggestion he goes shopping as he will need several outfits for working in, tops, trousers, shoes and coats, because no girl wears the same thing two days on the run or in the same week if they can help it.
Within a month despite his mother's reservations, Josie had become a permanent presence at both the salon and home. Though Joe still thought himself as a lad that preferred to dress in a rather unusual way for a boy. It was under Kay's now more gentle prompting that Josie became softer a gentler person, and generally a more feminine looking person. The hair had taken on an even more defined cut emphasising the girl in him. His ear rings became more decorative over time, small stones grew into hoops and onto dangling chains.
By the end of the summer holidays and the time came for him to enrol at college as an apprentice hairdresser he was admitting even to himself that work had rather taken over his life, he rarely went out other than to the salon and his whole world seemed consumed with finding out more about how to improve the way people looked, partly from reading, partly by seeing what happened at the salon and partly from trying things out on himself.
For the enrolment day he did not know what to wear, should he be as girlie as possible or back off to more boyish look. In the end he went for jeans, a plain top and no make up. The nails were still kind of longish, his ears still carrying studs and his hair a well cut blonde, but he felt easier signing in as Joe looking vaguely male than vaguely female. He still had to acknowledge his gender when he signed up as a male, so he was happy with style choice.
The reaction when he got home was unexpected, his mum asked if this more camp look was how he was going to be. He explained how it had been for college not work that he had changed his style, this made him feel she was wanting him to revert back to being a dull looking boy and only fired his enthusiasm to be more contrary to her wishes. The next day he went to work, fully made up, hair revitalised, biggest ear rings, and his prettiest blouse.
Kay and Denise asked if it was something they had said but Joe just pointed out he enjoyed feeling feminine so what was the problem. No problem they assured him and set him to his usual tasks. Come the break time Kay asked if he wanted to be a girl, he said not, he was a boy who just happened to enjoy looking feminine. So Kay asked 'how feminine?'
Joe asked 'what do you mean?'
'Well would you wear a dress or high heels, how about going out with a boy, all can be very feminine things'
'I just like being me' was all he could think to answer.
'Well just let me know if you want to develop that femininity some more, I am sure you would look great all dolled up.'
When he got home his mum noticed his pretty blouse and made the mistake of challenging his chioce. His reaction was to make up some argument about he felt restricted by societies constriants on how people dress and he was thinking of looking for something prettier at the weekend. 'But you are prettier than any boy I know already, what could make you prettier?'
Without thinking Joe just said 'A dress'
'A dress?'
'Yes I want to find out what it is like to wear something other than trousers' as he said it he was thinking that this maybe a hole to deep to get out of easily.
'A dress is very much a girl thing, would rather stop you being somewhere in between boy and girl that you are at the moment'
'Maybe, but I like being feminine and a dress seems like a next step'
'And what if I said no?'
'Then I would just have to find out on my own' Joe could not believe he had just dug his hole deeper, but then felt there was time to back down.
'I am not keen'
'I know but you can't stop me, it was you who had me have highlights, it was you who taught me the basics of make up, bought me the clothes and satin night wear what is wrong with a dress?' That was enough he thought, point made.
His mum thought for a moment and decided to take this head on, 'Right if you are so set on wearing a dress then you must do it properly. A dress looks best with heels, the higher the better, dresses are for a female figure so you need a smaller waist and a bigger chest, and maybe not essential but I think worth doing, your make up has to be full on, not the muted colours you currently use.' There was a pause 'You want to wear a dress Joe? then you bury the boy completely. Right Josie!'
Joe was backed into a corner he had just thought a dress would be an interesting bit of fun, but how could he back down, 'Fine. As long as you stop calling me Joe' This was said with maybe too much fight, but he was feeling pressured.
Both not wishing to back down 'Ok Josie I expect you by Sunday dinner to be looking like a complete girl, anything less and you go back to being a boy and we get your boy stuff out of the loft'
This was turning into a real fight that niether wanted to lose, but almost as soon as Joe had left the room both realised that they pushed it too far, if Joe turned up in a dress then it would rather seal his fate for how he looked in the future, which meant no more Joe. Why is he so set on the idea, was a puzzle niether never understood.
After all the new experiences, fights with his mother and his internal discussions, which way will Joe go when the pressure builds.
This is as far as I will take Joe in his life, unless I can be persauded (not bullied off course) otherwise, or someone else can see his potential :)
Joe was quiet at work the next day, when Kay asked him what was up she listened to his tale. Then told him he should not be upsetting his mother, but if he was sure he wanted to try a dress then she would help him in any way she could. Her first offer of help was to let him read through some fashion magazines suggesting he pick out a style he liked. Over lunch he looked and looked but was unable to settle on any one style so Kay suggested he think what he wants from the dress and asked him to pick a few words to describe what he likes about his favourite clothes then.
'Soft, smooth, nice colours.'
'Ok, so how about patterns?'
'Yes I suppose flower patterns would be more feminine'
'What about length, short, knee or long, what fits your idea of feminine?'
'Short is what girls wear, knee is more mature, more what a woman would wear. I suppose long is elegant'
'Ok we are getting somewhere. A mid length, soft cotton maybe, print dress. Flared skirt works best with soft fabrics.'
'I guess that sounds about right'
'good it is late night shopping in town tonight so get yourself down there and have a look round'
He got home about eight and with some delight told his mum he had been out looking at dresses that evening, she asked if he had chosen anything but said nothing seemed right. When she suggested he was taking this very seriously he replied that she was making it a serious issue. To which she backed down but not before reminding him he had till Sunday to make his mind up. It might have felt like a truce but it was just a tactical reorganising of strategy really.
Sunday came and he had spent his wages on his first dress, a pink and cream print with flowers running up the skirt and bodice, the fabric was a truly soft cotton which had been rouched around the bust and fell in flowing pleats down past his knees, a round neck and little puffed sleeves completed the dress. He had also bought himself some more tights and a pair of cream court shoes. He felt he had gone far enough, the dress felt lovely as it wafted around his body, he had the heels as she had wanted but he was at a loss as to how to alter his shape. So he dressed and did his make up, put in the long pink chandeliers and hung the pendant around his neck to remind his mother that she had given him them.
'hi mum, what do you think?'
She looked him up and down realising this could be a big moment in their lives. 'Very pretty, where did you get it?'
'Debenhams'
'Always nice stuff there, how does it feel?'
'Very nice, ever so gentle on the skin'
'Would you wear it again?'
'I think so it is very nice on, and if you don't mind'
'Well I think we have a problem if you want to look like a girl' she looked him in the eye 'you have failed in at least two ways today, one you are flat chested and though I can't see it I guess your waist is no smaller. I think I could add that the shoes are a bit plain for that dress, higher and dressier would look good'
'sorry I was trying my best' then he inexplicably said 'do you like the dress?'
'I do, but before I let you have some dinner you must fulfill my instructions' he began to look distressed as he had no idea how to do what she wanted. 'Come this way' she lead him to her bedroom 'Take the dress off' Then after a little rummaging in her drawers passed him a white satin padded bra 'Here slip this on' After a little fumbling he had the bra around his chest 'Now to give you a waist, lift your arms' She wrapped a corselette around him and pulled the laces tight 'Pull your stomach in and breathe out' and the laces went a bit tighter.
'Mum is this necessary?'
'If you want to feel feminine, you have to look feminine. Now slip these shoes on' she pointed at a pair of brown mules with just a strap across the toes and a narrow 3" heel. Her last action was to spray scent on her son. 'Ok put your dress back on and lets see how things have improved'
He had difficulty standing in the new shoes and had to take them off as he lower the dress over his head, but then once it was positioned correctly he stepped back into the shoes and carefully went to look in a mirror.
'Better?' his mother asked
'I see what you mean'
'Right, this is how it will be, if you want to be feminine I will expect you to wear a bra all the time, the corset until you have lost some wieght and heels, maybe not high like those but at least not flats or trainers.' She was hoping that making such tough rules would make him think again about being so girlie.
'But mum what about college'
'That is your problem Josie unless you want to be called Joe all the time'
His mum was pushing him and she hoped pushing him into backing down and being more of a son even if it was a very feminine son, but Joe was wanting to prove himself and reckoned a baggy top would hide his mother's new additions, the shoes he could swap once outside with a pair in his bag. Besides that set too, the rest of Sunday went well, Josie being reminded to tuck the skirt underneath when sitting, a few tips on walking in heels and small portions to start the diet.
The following Monday to prove a point to himself and his mum, he went to the shops at lunch time and bought himself several bras and when he saw some low wedge heeled black ankle boots he bought those also. So come Tuesday morning he went out of the house wearing an unfilled bra the corset and his new boots. His mum said nothing as she was not sure if this was a victory or not. The reaction of Kay at work was very different, she noticed the bra pushing the top out first and then the boots.
'Oh very nice I must say, but why?'
'Mum says if I want to feel feminine, then I have to look female, hence the boots and bra'
'Oh that is interesting, so was the dress nice?'
'Very'
'I see. Anything else your mum wants you to do?'
'Wear a corset'
'Thought you were but did not like to say, why?'
'Because I need a waist to be the right shape'
'If only I had a waist, but I think I know what she means. All or nothing is what she is getting at'
'Yes'
'and you can't give up the nice feminine things?' I nodded, 'so it will be full on female from now on'
'Well except for college, I am known as Joe there'
'Bit of a cop out and you will look very camp on you days in class, but it is up to you. Now the bra, what size did you get and have you anything to fill them?'
'32 B I think'
'Well for today get some tissues and pad them out to make them look more realistic, and might I suggest you save up and buy some inserts like the women who have a breast removed use, they would look so much better'
It was not long before Joe had saved up for his inserts and besides college days wore his filled bra all the time. And as the autumn chill grew he bought leggings and long tops, which he assumed rightly were just short dresses. With these new additions and another pair of low heels to work in, plus a new jacket he was unrecognisable as the boy that first started at Kutz the hair and beauty salon.
His mum was working on his diet as a way to make his life harder, but what was more of a challenge was the feelings Joe had for a lad who had come in for a trim. A nephew of Kay's who was a bit older and far more masculine in looks and manner than Joe could ever be, but what got Joe was that besides being good looking, Lee flirted with him. And then a week later with some lame excuse of a message from his mother for Kay, he turned up again and once agian flirted with Joe.
When Joe was alone with Kay next he asked if Lee knew that he was a femmy boy. 'Should think so I have mentioned it to his mum'. This confused Joe because he could not get his head around the thought that a boy would or should be chatting him up, even more worrying was that he enjoyed the attention. Kay broke into his thoughts, 'Nice boy Lee, don't you think?'
'Err well yes' stammered Lee.
'He fancies you, it is written all over him'
'Nooo, cant be I am a lad really'
'And he is gay'
Joe swallowed deeply, 'Oh'
'You should be flattered, nice lad like Lee. Does it make you feel more girlie to think of yourself as being chatted up because of how you look?'
'Not sure just yet, I need some time to think about that one' but Joe was blushing all the time.
'You are really cute when you blush you know' and after a pause 'So should I tell him you will see him after work?'
'What?'
'He asked me to find out if you would meet him after work and maybe go for a pizza or something, so yes or no?' Josie blushed some more and fiddled with his hair 'I shall tell him yes, being with a hunk like Lee will make you feel so feminine'
'But what should I wear, do I need to redo my make up? I will feel so awkward, are you sure?'
'Don't worry, wear what you are in now, he is not taking you anywhere for a date, just spending time to get to know you, but maybe we could give your face a little more sex appeal'
'Sex appeal !!'
'Just make you look a bit more girlie, not full blown night club look but something that says, I want to look nice for you, but not necessarily to have sex'
'Ok but definitely not an I want sex look'
Kay made the call, and at half five Lee was waiting for them to lock up, Joe had used a darker eye shadow and a darker pink on his lips with a wet look gloss which got Kay and Denise's encouragement. His mum was not expecting him home after he had called to say he was meeting up with some friends and would get something to eat. She had asked what friends as he lately hardly went out, from college he lied, admitting that a lad had been flirting with him was not something he felt his mum would like to hear. They walked round the local park that lead them into the town where Lee made for a Pizza Hut. They chatted about his family, his aunt Kay, the salon, Lee's job at a local newspaper. But after the small talk dried up Joe could stand it no longer and asked the only question that was bothering him 'You know I am not a proper girl don't you, I just prefer to dress femmy'
Lee took one of Joe's hands on the table and looked straight at him 'It is what makes you so special, you are real pretty and yet being a boy means I still fancy you, wierd I know. Maybe some sort of half way for me, with you I could hold your hand and not worry about being called queer, you look so great and yet I know that you are not really a girl. For me perfect'
'sorry I am not sure about all this, I just like being feminine never really considered if I like boys more than girls' then Joe thought he might have offended Lee 'but tonight has been lovely, I am enjoying myself. Honest'
Lee did not let go of Joe's hand until they had to leave. And once out of the building took hold of the hand again 'Have you kissed a girl?'
Joe was surprised by the question 'Well er, one or two'
'Have you kissed a lad?'
'No'
'Would you like to find out what it is like?'
'Er' was all Joe managed before Lee had stooped down a little and kissed his lips gently.
Joe did not have to pull away 'So now you have kissed a boy, any objections?'
'Er' he could not think what to answer but then said 'No'
Which meant Lee leant in and let his lips carress Joe's for a little bit longer. Joe opened his mouth slightly to breath which Lee took as a sign of acceptence and kissed a little harder letting his tongue lick Joes lips. Joe was even more confused than ever, this was the best kiss ever but it was not with a girl which is what he had always thought would be his default kisser. After what seemed like an age, but was barely a minute, Joe moved back and broke the moment.
'I take it you have no objections then?'
'I think I should be getting home' was Joe's reply, but instead of walking off, kept hold of Lee's hand as he moved away. Lee followed keeping a firm grip on his 'girlfriends' hand.
That was a rather defining evening in more ways than one. Yes he had kissed a boy and not been repulsed by it, but it was what his mum said when he got home.
'Right then Josie I have been working with you on this feminine boy life style you seem to like, but I think it is time for you to decide if you are a boy or a girl. You look like a girl but I know you are a boy and it is doing my head in.'
Joe had always felt his mum was more black and white than himself but still asked 'Why can't I be a boy that looks pretty, sort of somewhere in between'
'I have tried to put you off by forcing you into more and more aspects of being a girl, but you just go one step further it seems, so I want you to either make a commitment to stop or to consider that you might be transgendered'
'Trans what?'
'It means you are a girl trapped in a boys body, your physical looks do not match your emotional state'
'So you want me to go back to being a scruffy lad or what?'
'Go and see a specialist who knows about these things, maybe you are a girl'
Joe then had a flash back to his kiss with Lee and did not even have to consider the options, he had enjoyed being with Lee and to be with Lee would mean he had to behave like a girlfriend, if he went back as he suspected his mum wanted, to being an ordinary Joe then Lee would not want him. Decision made 'I am a girl, I like looking like this, I feel better when I am not dressing down to look less female for college days. Yes I want to be Josie.' but then added 'Sorry I am not sure that is what you wanted to hear'
His mum was starting to well up, 'No it is fine, you have to be true to yourself' she managed. But Joe felt himself drawn to her and gave her a hug.
'We'll be fine, you'll see, just let me be your daughter and I will try not to dissappiont you'
Joe went to bed in his satin nightie that evening after working through his beauty routine beforehand, but sleep was not easy after the evening he had just had. A kiss, the first that felt like a connection and not something that should be done. Then his declaration that he was a girl inside if not on the outside completely. Questions such as how different is Joe from Josie? Could he become a real girl? What does a real girl feel like? Are breasts important? In the end he fell asleep at what seemed to be just before the alarm went off.
That morning for work he picked out a long floral top, leggings, his higher heels and used scent for work which was a new thing to him.
His mum said 'You look nice this morning'
Then at work. Kay said 'Last night went well then'.
To his mum he said thank you.
To Kay he blushed, she knew where he had been and what might have happened.
Lee was waiting for the salon to lock up at the end of the day. 'You look nice. Would you like to go to the pictures at the weekend or something?'
Kay came out of the door 'Oh hi Lee'
'Hi aunt Kay'
'If he asks you out, make sure he pays, and if it is to see a film pick a chick flick, none of that macho sci fi stuff' Kay said to Josie.
'That would be nice, Saturday, but give me chance to get home a change after work'
'Seven?'
'See you at seven then'
He walked home considering what he had just done, this was a proper date with a boyfriend the whole thing. Sometimes he thought about what he should wear, alternating with times he thought he must be mad to have accepted.
Saturday came and Kay gave him a quick wash and style before he went home. He had already told his mother he was going out and would not be eating, so she was partly ready for going out socially, something he had not done for months. What she was not ready for was the sight of her son coming into the living room wearing his dress, some new sandals with really high narrow heels, a neat jacket and for the first time a handbag. She was just getting used to the sight of her son when the front door bell rang.
'I'll get it' Josie said rather too quickly. 'Oh hi Lee' then turning back into the house 'See you later mum.' And he was gone, the door shut behind him. His mum was up and looking out of the window like a shot. She told herself she should have expected something like this but to see her son walking down the road with Lee was a rather abrupt shock. She had until recently always imagined seeing her son walking down the road as one half of a couple, with Joe walking beside a pretty girl, not Joe being the pretty girl. But then as she watched them walk away she felt an odd sort of pride, Lee was a good looking lad and Josie made a good looking girl beside him. This she knew would take some getting her head around as she went back to watching a Saturday evening game show.
Sunday and Josie was up early and making herself as pretty as possible, Lee was coming round later and they were going for a walk. Leggings, top that doubles as a mini dress and high heels. Josie wanted to look as much a girl as was possible for Lee and his mum noticed.
'This boy, more than just a mate I guess.'
'Oh Lee is just one of Kay's nephews, we enjoy each others company.'
'You seem to enjoy being more feminine for him as well.'
'Do I?' Josie said hoping to sound surprised.
'Yes you do, I would even say you fancied him if you were a girl.'
'Well I'm not, I don't fancy him and we are just friends.' Josie lied.
But the day was to get far worse than a little spat between mother and child. Josie was done up to the nines and walked down the road not considering how others might be reacting, teenagers can be quite unaware at times. But that afternoon while she was tidying the garden on more than one occasion neighbours passed comment over the front fence about a girl they had seen coming out of the house and Joe was wearing some unusual clothes lately. She defended by saying he was training as a hair dresser and it has changed him a little but she had no real answer to the questions about who the girl was that day.
When Josie came home he found his mother sitting quietly in the back room clearly upset. He gave her a hug and asked what was wrong but she told him nothing then went to get the tea ready. It was later that she asked how serious he was about his new feminine look. His reply was pretty much expected, he liked it and to the question of whether he preferred to look like a girl or a boy his immediate answer was a girl. This made her go quiet and Josie knew he was the cause of her distress. Eventually she told him about the comments and his bubble was burst. He never really thought anyone bothered, yes it had been a concern at the beginning but as the changes got more feminine so his ability to hide them got harder and he stopped trying and had felt no one really cared how he looked anyway. This was a big shock. There was not much said after that, Josie went to his room and cleaned himself up then tried to work out who he was, what he was and what he was going to do. The upshot was that he went to work in the morning with no make up on, flat hair, baggy jeans, trainers and a loose sweat top, he even clipped the nails shorter. His mum saw him and cried a little.
'Oh Josie, I am so sorry I should have said nothing.'
'No mum I am fine, maybe best if I just accept that people with my body should dress like this.'
'Still I am sorry.' she repeated as she gave him a hug.
At work Kay was shocked and sent him in the back so they could have chat, she knew something must have happened and initially thought it was Lee, but as she got the tale right she became rather indignant that nosy neighbours should be controlling him to this extent. Surely he should be able to dress how he wants, though in truth she did know there was a lot of people who were rather narrow minded to anything they dont understand, Lee had had to endure some unkind comments so could understand something of Joe's upset.
The dressing like a boy continued for a few days but it was clear that Joe would rather be Josie, comments from customers like 'Where is that nice young girl today' only made things worse. In the end Kay rang his mother and they had a discussion after work, Kay, Denise, Joe and his mum. Joe was the only topic, did he see himself as a boy? what would he do if he could not dress as a girl? how much did he fancy Lee? could he live as a girl all the time? Not that any of the others knew it but Kay had a plan and once they had asked questions and discussed the merits of Joe versus Josie, and was satisfied Joe would be happier dressing like a girl, she made her offer. She lived some distance away and had a large house, Josie could be her lodger but there were conditions so as nosy neighbours were not a problem again. Joe would have to present as female all the time, ideally ultra feminine so as to leave no doubts, she would contact the college and infrom them of the changes and make sure that there would be no problems, if there were then he should enrol at another the next year hopefully his history better hidden.
Joe and his mum went home hardly speaking until the evening meal was on the table.
'So what do you want to do?'
'What do you want me to do?'
'I want you to be happy, if that means you live with Kay and I have a daughter then I will handle it.'
'I am so sorry, this was not meant to be how I wanted to be.'
'But it is, and the choice is yours, not mine. Unfortunately it is what nieghbours say not me, so how do you want the world to see you?'
'Will you be upset if I say Josie.'
'I will cope, you have to leave home sometime.'
We hugged a lot that evening but the world was changing and life would be different from then on.
How far would you go?
Where is your line that you will not cross?
Are there any restriants on you?
At what point do you say stop?
Matt and John were always competitive, they would go to the gym and have to do more distance, time, weight, whatever, than the other, and they would challenge each other over fitness as well as random things, but whatever they did it was never certain who would come out on top. They were also gay and had the stereotypical fit and toned man look, wearing tight vest and trousers to show off their hard won physique, but neither fancied the other as they were both dominants and would not want to be the others bottom, both however did have steady and reliable partners who worshipped them, Jamie and Paul thought they looked great, and though wanting to look toned did not have the frame or body shape to achieve anything masculine, so happily fell into being Matt and John’s submissive partners.
One Saturday night they were out as a four and things were going slowly when a transvestite came into the bar, he was a terrible advert for the cause, matted wig, visible shadow on his face, beer belly and badly put together outfit. They all made fun of the poor unfortunate but it had set a seed in Matt’s mind for a challenge.
Sunday morning found Matt and John running in the park and discussing the previous evenings events. Matt commented on the TV and John agreed he was terrible, then Matt suggested Jamie and Paul would make better cross dressers given half a chance, John agreed but went further suggesting that Paul would be better than Jamie, and so the challenge was set. By their next Sunday run they had to get their partner into something female, without them knowing about the challenge, otherwise it would be too easy.
The week rolled by, and Sunday came on. Matt had managed to get Paul to buy new trainers but not from the men’s section, from the women’s they were light blue with silver detail, very nice said John who had got Jamie into wearing an apron when he was cooking. It was now they realised they needed a referee to decide who had won, as there were no references to judge by. They later rang a friend called Angela a close friend of all four to ask if she would judge who had won.
Over a drink the three of them sat down and discussed what they were doing, Angela reckoned that many men wore ladies trainers especially as they were a slimmer fit, and an apron was just convenient and practical, so judged them equal.
Disappointed they went off sure that by the next weekend they would have got their partners onto something properly feminine.
Once again they needed Angela, John had bought Jamie a short nightie telling him it would turn him on, Matt had persuaded Paul to use lip-gloss. Angela felt lip-gloss though very public, was something many gay men might use, but the nightie was the winner, just a shame it had been a private affair. Matt felt he could top the nightie and said so, saying by next Sunday he would have Paul in something to top the nightie.
The following weekend Matt was confident, he had persuaded Paul to try silk knickers, which Paul apparently loved the feel off. This re ignited the challenge. If Paul would do this then Jamie would surpass it.
By the following Sunday Jamie was wearing knickers and camisole sets as well as his new found nighties, the newest being full length, satin, lace and pink. Paul had been persuaded further and he too was wearing camisoles under his male clothes. Angela judged it a draw, but suggested instead of trying to compare different things she would give them something to achieve, for that week she suggested complete loss of body hair, they agreed.
By the weekend both men had hairless partners, and both said how nice their skin felt to touch and that they would be keeping Jamie and Paul hairless from then on. Next week she said she wanted a night out with them, they had to be wearing the underwear, which both knew was not a problem, but she wanted to see either arms or legs to verify the hairless body challenge, and for that weeks challenge they had to wear a delicate piece of jewellery, not a chunky man’s piece.
They turned up at the appointed bar, Jamie in a t-shirt; Paul in a sleeveless top Matt hoped to show Jamie’s off bare armpits for a bonus. Jamie however won with the jewellery; he had a thin neck chain with a stone hanging from it as well as a delicate chain around his wrist. Paul did have a ring on his thumb and a ruby stud in his one pierced ear, but Angela felt Jamie had it that time.
Their challenge for the next week was to get the boys to have both ears pierced. But this proved quite easy, both relationships easily accommodating this demand.
The following week she wanted them to get Paul and Jamie to have a manicure, not that hard, but to keep a coat of polish on them, she did not say a colour so both ended up with clear polished nails.
For her next idea Angela thought one of them might refuse at a salon, she suggested highlights or a colour change, something she knew some gay boys would do, but at a salon, that she was unsure about.
She had underestimated the willingness of the boys to please their men, Jamie was now a blonde and Paul had silver and gold highlights in his mop of a haircut.
For what she said would be her last idea because no one seemed to be winning, she asked if they could meet up the following weekend when the boys should be wearing something that screamed female and for all to see, nothing like underwear this time. This time she felt sure one of the men might give in, or one of the boys might refuse to wear whatever it was they were being persuaded to wear.
Jamie was bought a lemon angora top with an unusually deep V that on a woman would display some cleavage; he liked the gift and needed no persuading to wear it out that Saturday. Paul was less obvious he had on white cotton trousers that hung from his hips and flared out to unbelievable hem lengths, Angela’s response was to declare it a draw, both men could get their partners to do whatever they wanted and both looked comfortable in their feminine styles. But this last challenge sparked something between the boys, seeing each others new clothes and realising how they had both got piercing together, been and had their hair coloured, worn jewellery, and when they talked found out what the other was wearing underneath, it was obvious they had been used as a challenge, Matt and John both admitted to what they had done, but insisted they had only improved their looks by doing these challenges, there was nothing detrimental, and the boys agreed because they loved the soft underwear and nighties as well as the changes the challenges had made to their appearance.
The following morning while the men were out running, Jamie was round at Paul’s discussing what the other had actually done, Jamie liked the cotton trousers Paul was wearing and offered him the lemon top to see how they combined for a look, and both loved it. Then they got around to the nighties; Paul got his long satin one out and Jamie immediately announced he was getting one also. They knew the challenge had come from the sight of the ugly TV, but now they were cross-dressing themselves they wondered how far they might take it themselves. They choose not to push it too hard because they were gay men and going to feminine might put off their partners, so they would give it a week as things were, basically the underwear and nighties to judge how Matt and John would react to them staying ultra camp. This went so well, neither Matt nor John objected to Jamie and Paul still wearing the knickers and nighties, even making it clear they were staying in one evening to clear their body hair and do their nails created no complaints. This meant that Saturday morning the boys would be out shopping. The men had been able to say the purchases were for a girlfriend as a gift, but two camp men buying first a long satin nightie, then a cream roll neck top from a woman’s boutique was causing them to get embarrassed and have fits of giggles. But by the time they had bought trousers for Jamie they had got used to the awkward feelings and were just going for it. So much so that as they passed a make up counter they bought lip-gloss and mascara knowing that they had seen boys wearing these already so should be fine for them.
That evening they were out as a four as they always seemed to recently, only this time the boys wore their female clothes, jewellery and make up, loving it. Feeling completely at ease with their partners who were the clearly dominant men while they fulfilled their role as the sissy in the relationship. After a few drinks they plucked up courage to ask what Matt and John thought of their look, John just kissed Jamie very powerfully, while Matt asked if the long nightie was still available. A positive result.
On the Sunday, the boys were chatting on the phone seeing how it had gone the previous evening, and when they both realised how well their purchases had been received they were left with the dilemma of what to do next in this cross dressing adventure. They could go straight for skirts but felt their men would baulk at this so wondered what they could do without going full on.
It was now their turn to contact Angela, they knew her part in the challenge and thought she might like to continue it but in a reversed way, what could they get away with before comment was made. She told them not to get their haircut, to let it grow, but to maintain the new colour they had got. Also to file their nails not clip them, and let them grow a little. All a bit long term they felt but definites for the future. For a more immediate challenge Angela suggested wearing some of their new clothes daytime, maybe even try out the make up daytime in the week as well.
The following week found both ringing the other to tell what they had done, Paul did the weekly shop in his trousers, Jamie went to work with mascara on one day, which inspired Paul to try the same. By the weekend they were so excited they wanted to shop for more things. Paul bought himself a matching nightie and wrap saying how this would work magic on Matt. Jamie bought another top, this time a soft cotton kaftan but did think it might be too much.
He need not have worried the top was a hit with Matt, while John suggested Jamie be a little more adventurous in his clothes selection. For their Sunday chat they could only say wow that went well. Jamie was going to try out the nightie and wrap that evening and would let Paul know how it went. But by the Tuesday both had decided to see how mascara would go fulltime, upping it to lip-gloss in the evening by Thursday.
They kept it at this level for about six weeks, the mascara became fulltime, Paul was able to wear his trousers more often, but that was just because he worked in a call centre and Jamie worked in an office that was a bit more conservative, but he did try out his tops on several occasions without comment. They did shop and increase the number of tops, Paul bought a kaftan style top and enjoyed the girlyness of the look as well as the attention Matt gave him.
It took about six weeks for the piercings to heal, by which time the roots were beginning to show in their recoloured hair, so Angela suggested they have a trip to a salon to get their hair sorted, but then as a challenge they should buy some earrings and see how girly they would be prepared to go in with the style.
Their next Saturday was now full, a salon visit then shopping, nothing drastic, just getting the roots done and a bit of a trim to tidy up the ends, but Angela had insisted on nothing too much being cut off, they had to wait till the length was better before cutting was a real choice. Then it was off to find some ear decorations, first they looked at small rings with a stone or a fancier stud, but these they knew many men, not just gay men would wear, after much looking and Jamie getting distracted and buying himself some new underwear, Paul bought a pair of hoops and Jamie chains with fine tips that allowed them to be threaded through his holes. They were not allowed to point out to their men what they had bought; rather they had to wait for them to be noticed. Unsurprisingly both earrings went without comment, meaning, according to Angela, they were not feminine enough and they needed to try again.
For the next weekend Paul had bigger hoops and Jamie a red stone dangling from each lobe. This time the jewellery was noticed and for the first time were referred to as girls, well they were in full feminine outfits of cotton trousers, soft short tops and make up, not to mention the jewellery of earrings, as well as necklace and bracelet they had worn before.
Buoyed with the success of the fun they were having, they wanted to try another challenge, yet at the same time their wardrobes would increase and the small collection of jewellery was bound to increase. Paul started with a chain bracelet, Jamie followed with a necklace and an anklet. It took three weeks before they went out fully glittered up, non to discrete earrings, pendant necklaces, bangle style bracelets, a couple of rings and for Jamie his anklet.
The men’s response was very supportive telling them how nice they looked, encouraging them to dress more femininely all week and not just at the weekend. Angela recognised that the jewellery had not found their limit for femininity, and suggested that they get some shoes from the female stands. The boys had a fright when they saw the choice, nearly everything had heels on them or looked just to butch and practical for what they wanted, Paul found himself some suede sandals with a small wedge heel which were not to dissimilar to his beach flip flops, Jamie did not like things between his toes so settled for a beck shoe, but not a boring blue or white his were lemon which would match the angora top. Angela’s response to Paul was that now he should start doing his toe nails as well with them being on show. Matt and John’s reaction was to just call them girls far more often, but still no one was saying, enough it is time to stop this.
Two weeks later Angela challenged them to try proper heels and coloured lip-gloss, she felt this might just make them look like and feel like girls, maybe crossing a line they did not like. But she was wrong, the shoes were conservative, low block heeled courts and the lips were certainly pinker now, but they did look more feminine.
Having failed with that challenge she told them for their next weekend eye liner was a must and new shoes without block heels, they would be allowed the stunted kitten heels if that is what they liked. Paul did get himself some kitten heels but Jamie bought a pair of boots with a low but narrow heel. They had bought them one evening and then had plenty of fun telling each other how odd it was walking in the new footwear, and that combined with eye liner practise, meant by Saturday they were ready for an upping of their look towards the feminine. Matt’s reaction was to call Paul, Paula which gave everyone a laugh, but it stuck, Paul was from then on called Paula by everyone within the four and over time it spread to the wider circle of friends who had not let it go unnoticed the change in style of the two friends.
Angela had a serious eye contact talk with Paula when this happened, wanting to know if he was happy with the new name, and when he did not look away as he said yes she knew it was for real. So she challenged them to learn how to pluck eyebrows and thin theirs to a shape they liked. First they looked at glossy magazines, then on websites to find out how to restyle their own particular brows, Jamie’s were quite fine already but were thinned non the less, but was not that noticeable, Jamie had darker and bushier brows so when he picked a tadpole shape it was Jamie who asked if it was not to far, Paula said no and asked Jamie to get on with it. To be fair neither had a shockingly dramatic shape, but they were clearly different from before.
It was Paula who now suggested they try eye make up, but Angela had a better idea, first go to a salon, get the roots redone and now their hair was well past their ears and in Jamie’s case well down to his shoulders, it was time to get a cut. She took time to show them hair styles asking what they liked and suggesting what might suit them, this took all Friday evening, but by the time they turned up at the salon they had a photo cut out of a magazine and ready to ask if the stylist could do it on them. Paula’s hair was cut so it was long all the way round, needing to be swept back over his head or tucked behind the ears, Jamie came out with a gently waving perm, giving his hair body and lift, and luckily for him enough length so he could tie it back on Monday when he went to work.
Once again Matt and John loved the changes, Jamie being rename Jem. They were not yet fully aware how feminine they looked, but now Angela said was a good time to find out more about make up and how it changes and improves the facial features. This was the first time she had accompanied them shopping but felt there was so much to take in they would need help. She was thrilled when a sales assistant came to help, Angela explained how her friends had no idea about make up, with some story about being student drop out types who now wanted to look more normal, the sales girl lapped it up and offered to give them a make up demonstration. An hour later they walked out with perfect foundation, defined cheekbones, sultry eyes and kissing lips, as well as bags of cosmetics they would need if they were to try and recreate the look. Once outside Angela pointed out that at no time did the girl take them for men, which made the boys giggle. Being in charge of the situation she claimed that as they were looking like women then they needed a bra. Walking them into a store where they each bought three b cup bras, then she made them go into the ladies and put one on and fill them with tissues. They came out looking far more self conscious than she had ever seen them, maybe this was where they stopped, but later that evening she bumped into them, both dressed in all their most female attire, faces still made up and most noticeably, their chests sporting breasts, bigger than a b cup was meant to be. She was wrong this had not been a stopper just a pause.
It took them several weeks of private practise and consultation with each other and Angela before they went out again with full make up on, but it was worth it as they felt more finished in their look. They also liked the feel of a bra, but for daytime wore AA cup so it would not show at the front if they wore thick loose tops, but would be felt by them as it wrapped their chests snugly.
Angela was running out of ideas, she could get them to try a skirt but still felt this maybe too much, instead she went for more pronounced shoes, gradually upping the heel height, and once they were happy in 3” courts moved towards 4” sandals, and then onto shoes with no ankle straps, just a strap across the toes to keep them on the feet, meanwhile they had taken to wearing their first female shoes in the daytime and for work on occasion.
Next she persuaded them to try a new top style, they had always picked shorter tops that maybe reminded them of a male counterpart, but this time she wanted them to try a longer top, one that would come well below the hips. Paula took to this easily and bought a black and white geometric pattern which stopped below his crutch, actually looking like a mini dress, with a fitted bust and delicate cap sleeves, Jem at first had trouble finding something he liked, and ended up getting a long white jumper that he easily sat on as it was so long. Angela told them they were beautiful and ready for the last challenge. Next Saturday they would going out in a skirt, tights or stockings, (that choice was up to the men), full make up, new top to go with the shirt and her treat a wash and blow styling at the salon.
At first they were not sure if they could wear a skirt, it meant taking away the last vestige of their male look, but there was nothing left in reality, so they took Friday off and shopped together, they now looked so female they were comfortable browsing the rails and looking at the mannequins for ideas. It was late when they got home, both had chosen full layered skirts that fell to mid calf, Jem a brown, Paula a green, they had cotton blouses with ruffles at the cuffs, neck and down the buttons, they also had a pair of stockings and tights each but would need to ask before opening a packet and trying them on.
Saturday they meet at the salon early afternoon, dressed quite reserved for them now, flat shoes, jeans, and a plain shirt with only a touch of make up, but they still looked like Jem and Paula, not Paul and Jamie. The stylist did wonders on their hair; Jem’s was given loads of volume and curl, Paula’s was swept across his face and lacquered in place. As an extra unknown treat the salon also painted their now trim nails a vibrant pink and given a lipstick to match them. They had left Jem’s clothes at Paula’s and went there to change, the men had been told that it was to be a special night, a meal and a good club possibly, but all they knew was that they had been asked stockings or tights, both said stockings as they reverted to male stereotype.
The cab picked up the girls at 7.30, now fully dressed in their skirts, stockings, 4” sandals, C cup bras, long pendant earrings, obvious rings, matching necklaces and bracelets and small bags to keep those essential girly bits in like a lipstick and tampon. The cab driver knew nothing was amiss, Matt and John at first did not recognise their partners, both of their girls being on them before they could say hello. There were lots of compliments on how good they looked, some pleasant touching. Then it was off for a good restaurant then onto a club and some close dancing, followed by a night of showing these boys what a girls place in bed is, but they knew this already, that was part of the reason they had worn skirts that evening.
Matt and John had no objections to their partners behaviour that evening, and over the months that followed even encouraging it with presents that might seem more appropriate for a girlfriend, such gifts as scent and jewellery were common over the year. And things seem to settle down after they had worn their first skirts, they were still camp in the daytime, straight men do not often wear mascara and lip gloss, nor do they wear silk underwear but Jem and Paula did, but it was dismissed because they were gay, so camp was to be expected, the full on female look happened in the evenings and all weekend, with the nights being a proper dressing up time, now skirts were included the whole range of women’s clothes were at their disposal, minis, evening dresses and revealing tops became their Saturday night preferences especially if their men were taking them somewhere special and straight.
This part time female life was suiting Jem and Paula when Angela made a reappearance in their lives, she had been away and not out much when she was around so they had not seen her, and besides the odd phone calls for advice, there had been no contact. Then they bumped into each other one weekend when they were in a club dancing, Jem in a crochet top that gave his white satin bra a very visible outline, Paula opting for a tight top instead but with a flared mini as opposed to Jem’s jeans, both on towering 4” heels and with excellent make up, she had to make sure it was them before approaching them. She was thrilled to see they had kept up with the new style, and asked if they were still enjoying it, they told her all about recent shopping trips, salon adventures and the reactions of Matt and John. But it was later in the week when she accidentally met Jem, who was looking very much like Jamie, he was wearing a nice knitted top, jeans and flat shoes he bought from a ladies selection, his hair tied back and no make up. She took him for a coffee and asked why he seemed to be reverting back to boring camp, what did John think, what underwear did he have on, if she saw Paula now would he too be a boy. In short she thought she had left them moving towards full femininity each trying to go one better than the other, but it seems like they have stopped the competition and were actually going backwards. Jem tried to explain he had a job that he thought would not agree to a way-out change of identity, John loved it when he dressed up at the weekend, but close shaves need a few days to recover and after a weekend he needs to let his skin recover.
Angela had some time to herself and pondered her two projects and how they had turned out deciding that she wanted to find out more about the situation, first she contacted Paula to find out if Jem’s experience was duplicated, the answer was, nearly, Paula still wore light make up as his beard was light, but for work his clothes were camp and shoes flat. Next she rang Matt and then John to ask about their partners and find out if they were happy with weekend girls. Matt corrected her when she called Jem Jamie, but was happy for him to do what he likes as long as he was happy, but yes he did like the girl in both Jem’s look and behaviour. John was a little more disappointed she felt, he would like to see more of Paula in skirts but knew how hard it was for him to do it with work and things, so would settle for what he had. This lead Angela to go out and look for fresh challenges for the boys after getting support from the men she invited Jem and Paula to her flat and showed her some websites she had found, it was a mid week evening and they were pretty much in boy dress, so she mocked them for being so conventional saying they should revert back to their old names, being essentially submissive characters they said they were sorry and what should they do. Jem she said should go for beard removal, Paula should wear his bra fulltime again, when he suggested it would be too obvious she allowed him to use AA cup bras, at least to start with. They both had to resume fulltime clear nail polish, she also planned a salon visit, Jem was still blonde and Paula had let the highlights grow out, their hair was certainly longer but the style nothing different from early on really. She would leave a more dramatic style for later, first she had a few other ideas to get on with.
A week passed and the boys were unsure about how things had changed, Jem had been for his first appointment and had a sore face, Paula had gone to work in a bra but felt self conscious in it, but Jem reassured him that they had felt like that before and now look at them enjoying what first had worried them. Angela wanted to know how things were going and was pleased they had done as she suggested, but she was still trying to find the point at which they say no.
A fortnight later, she tells them she has a treat. They already have discovered silicon inserts but Angela wants them to be fixed more permanently, at least Friday evening to Monday morning. And as she is giving the boys their first lesson on how to fix them she realises they never wear tight fitted skirts because they have not worked out how to hid the bulge except with control pants that they don’t like the look off. So having spent time doing research, she explains how all good trannies hide their bits pushing them back inside and taping the remainder up tight. It takes a while but soon she has two boys who at a glance pass as girls even undressed, but for certain in their satin underwear. That Saturday they had to go and buy something either with bare shoulders, i.e. no bra straps showing, our a skirt that was tight across the hips, in a way displaying the fact they have no bulge. That evening saw them out in tube dresses, one gold the other silver and made up to the nines, their men were very impressed with the new look, even more so when they stripped off at night and retained the shape the dresses had indicated before.
Angela wanted to push them further into being more feminine through the week, which she felt was about the only challenge left. Jem was loosing his beard, and though reluctantly at first now wore a bra full time like Paula. Next she suggested they wore flat sandals full time, which again met resistance but in the end they went to work in sandals that were far too delicate for a man even if the colour was black.
Over the weeks she encouraged them to grow their nails again, nothing long, just neat and rounded, definitely not clipped and short. She had had them on the challenges again for about three months; Jem’s beard hardly showed now and had no excuse for avoiding make up full time though he still would not wear it to work. Paula had been persuaded into wearing light foundation, a lip-gloss and mascara fulltime, and with the other fulltime changes was starting to create gossip at his work, which was starting to worry him a little. Now Angela wanted to see if she could be bold and make a final dramatic change, she checked it out with Matt and John first, and then booked the salon. The boys thought they were just going to have roots and a tidy up. What they got was a complete shock, Jem realised something was up by the amount of hair on the floor, his blond roots had been done but the style was like something Bowie had in the 70s long feathers with a spiky top. Paula faired no better; he was now auburn with lots of tight curls tumbling down to his shoulders. They both loved the new styles and wanted to dress up and go out. They thanked Angela profusely, the look on her face was that of a proud mother, but they all knew that Monday was going to be a hard time. Matt and John loved their boys new look and told them Monday was not a problem, they looked great, and in their dresses dead sexy.
They had a fantastic weekend being totally girlie, but Monday was hard, Jem could not tie his hair back and had to show up with it just a little flatter than when he walked out of the salon, Paula could get a pony tail but the new colour and the curls still showed in the tail. By lunch they had both had trouble, Jem had been into see his manager who told him the hair had brought to head the issue of his appearance and though not inappropriate for a girl it was not good on a man, and though company policy would not stop him, he was asking him to be a little considerate to the company and his colleagues feelings. He was almost in tears when he rang Paula who had not had any company problems but some of his work colleagues were taking the piss with comments about his look. By the end of the day they were glad to get home and escape. It was Matt who had a solution, he loved Paula best at the weekends when he was a full on sexy woman, and his reaction to the comments at work meant that he would probably revert back to a more Paul look, so he called John and Jem inviting them for a meal. This kept Paula occupied preparing the food while Matt made a few calls, by eight he was ready, John and Jem arrived, Jem had been persuaded to be a bit girly and wore a dress, but something rather subdued really. Then as they got past the pleasantries Matt was cornered with questions about what was this all about. He started with a bit of a monologue explaining how Jem and Paula came to be attractive girls, and how he felt responsible for starting this chain of events, and how he loved Paula even more when he was looking female sexy, and knew John felt the same about Jem, which was odd given they were all gay and did not fancy women, but today had caused a problem, and he did not want to go back a couple of years and loose Paula and get Paul back. So he had a suggestion, they pack in at their jobs and work for themselves, doing what? are you mad? they came back with, but he was ready. Everyone knows gays are more careful about being clean than straights, well the urban myth says so, and Jem and Paula are great housekeepers, so he had rung around and there seemed to be a market in the gay community for gay house carers.
They were a bit stunned at Matt’s optimism but he persisted with his idea explaining how it would work and assuring them it would succeed until the boys agreed to give it a try, there was one proviso made by John, there was to be no toning down of the girl in them any more, he wanted his weekend girl to be a week day girl as well, this would not be a problem it seemed.
They advertised in gay papers and amongst friends and soon had enough work to keep them busy, and enough money for clothes, shoes and make up so it was considered a success, being female fulltime was fine. It was some two months later Angela was chatting with them, she was really pleased with how things had worked out for them and how their femininity was blossoming, then she suggested a new challenge, she knew their men liked the fact they were really boys and that they have boy bits, but had they considered breast implants, then they could throw the falsies away, feel with their nipples and enjoy going braless with just a silk camisole on. She could tell from the quick glance between the two that she still had not found something they would not do to be more feminine. Accepting these two boys just revelled in the joy of being able express themselves in a completely feminine way, and with a hug wished them all the best.
My usual Friday routine goes something like, text at lunch ‘you fancy going out tonight?’ my reply ‘OK you choose’ the reply usually says ‘’Mine for 7.30’
Today was no different, Alex and I had known each other since being kids, and had recently renewed a friendship that had not really been a strong one before, we would take the school bus from the same stop and were in the same year so had conversations about school work not done etc but we did not play football together. It was nice to get to know him now though, maybe he had changed, more likely I had though.
I knocked on the door a bit early, no one came so I just let myself in.
‘Hi, only me.’
‘Sorry, fell asleep in the bath.’
Oh I thought to myself, last time Alex had a bath he got really dressed up, I wish he had told me I had only come in my jeans.
‘Make yourself a drink, take a chair, I will not be long.’
An understatement Alex is never ready on time.
I took a seat and looked at his photos on the sideboard, his mum, an old one of his dad, a picture of him at dance school. I know he likes this one, he is only about 11 but his long hair, the leotard and stage makeup he does not look very manly, my dad used to say he was pretty, well he used to say other things about him as well, like boys who do dance were puffs, I told him there were ten girls to one boy, my dad said it does not matter he will not be interested in them and I should keep well clear.
I did wonder at times how tough he must have been to keep up with the dancing when he got so much abuse for it, no one ever beat him up, he was too quick for that but the name calling was enough to make me uncomfortable, but then I too was beginning to feel different when other lads described fancying girls and how they got stiff thinking about them, it never happened to me, but boys well that was what made me different, I could feel my body react at the sight of a good looking man. I tried to crush it and conform but at the same time I understood a little of how Alex felt.
‘Won’t be long, just got to dry my hair.’ Alex shouted downstairs. His hair had always been long for a lad and now he was 23 he had been through several styles, some outrageous even for him, others quite dull, at the moment he was dark blonde with a bit of a wave and a long fringe he constantly is tucking behind his ear. I mused to myself ‘Drying his hair, possibly getting dressed up for certain.’ You see we either go out on a Friday to the pub and play pool or darts if he came down scruffy, jeans and a hoodie. But if he fancied going into town and clubbing it, (even though he had given up on a career in dance he still enjoyed moving to the music) he would wear something that showed off his smashing legs. Last week he had worn a short red skirt and matching see through top, but my favourite is pale blue dress with halter neck and wide skirt, bit like the famous Marilyn Munroe dress but shorter. When he is dressed up it is not like he is a different person but I do at times have trouble recognizing that he is not a man and only has one hole for me to pleasure him with later. He is so good that I still remember the first time I meet him after we left school. I was in town at a gay bar I like with some friends when this girl comes up and says ‘hello Mike.’ I must have looked dumb because he followed this up with ‘its Alex, from school, remember?’ then went on to mention a few things to help my memory. Eventually I managed ‘Oh that Alex, how are you doing, the dancing?’ And within minutes were chatting away like long lost friends, we discussed school teachers, what had happened since, and why we were both in a gay bar. I told him I came out at uni much to my father’s disgust, Alex had done performing arts and kind of drifted into who he now was, a weekend girl, a weekday call centre advisor. I still remember what he was wearing, denim, but not like my jeans, no, his were tight and tucked inside his high heel boots and the denim jacket was not a biker style, his was short and the buttons would never meet across his un-manly chest which was covered with a pink fluffy jumper. Well we exchanged numbers promised to keep in touch and we did.
The hairdryer turned off and I heard the sound of wardrobe doors shutting, I looked towards the door not sure what to expect but after all the preparation I was thinking we would be going out as a couple not as mates.
At last he was stood at the door in denim, ‘Sorry I took so long, got awful sweaty coming home and well I needed a bath and I have such a week, well I fell asleep, didn’t mean to , honest, but my hair got wet and one thing leads to another. Anyway what do you fancy?’
‘Oh the Swan would be good, beat you at pool again.’ He was as male as he could ever be in jeans and a striped shirt. ‘Thought you were getting dressed up?’
‘What! After the day I have had I just want easy and some fun with my friend. Now come on I think I owe you one from last time.’ He winked at me as he took my hand to pull me out of the chair. ‘Got your favourite knickers on just for you, now let’s play with some balls and see if we can aim the cue at the right hole.’