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I had thought about doing this sort of thing before, but never had the opportunity or the nerve to do it. Yes this was my chance to dress as a woman, without being a weirdo or pervert.

I had been in one of the pubs I like to call at on a Saturday night because it has good music and once a month it does a theme night, music and style of a decade. I had been to a few dressed as a punk and one as a teddy boy, but this time I had been talked into something I was possibly drunk enough to have said yes too with a little to much ease.

But then it was then Sunday morning and the paper was by my clothes, there were 53 signatures, mostly people I knew, all agreeing to buy me at least one drink if I did it, plus John the landlord had offered me free drinks for the evening if I turned up properly ‘done up’ as he put it, there was also the prize for best outfit to be considered as well, which if my alcohol filled memory had remembered correctly would be mine if I went for the whole woman role and not just a pantomime dame look.

It was not until later after my Sunday run to keep fit that I reflected on what the costs and consequences might be. I had to find an 80s outfit, Dallas sprung to mind, I had to get clothes, hair, make up, and lots of things I had not thought of probably. But on the plus side I did have two weeks before the event and there was always the bottling out option.

Nothing happened until Wednesday, I called for a drink on my way home from the gym and meet Hazel, a lovely bubbly person who was good fun to be around.

‘Hi Karl, so are you going to do it?’

I played dumb ‘Do what Hazel’

‘Come to John’s 80s night, John reckons you wont’

That challenge changed my response from, I don’t know it is a lot of effort, to we’ll see.

‘I was hoping no one remembered, but if John thinks I wont then as sure as anything I am going to give a good try’ hopefully that has not sounded too keen either, did not want her thinking I was one of those oddities you get on Jerry Springer. ‘But I think I will need some help, can I get you a drink?’

I listened as she went through a list of things I would need to get or have done to me if I was going to do this properly and not just throw a dress over my vest and boxers. I would need an outfit, shoulder pads, loose blouse in silk would be good, pastel colour if possible, a ra ra skirt, tights, heels, chunky jewellery, wig with lots of hair to style, and a make up kit, and that does not include a coat or handbag and accessories. Living alone this was a revelation to me, I had my bloke stuff and my gym stuff along with things to keep me clean and smelling good, but this list seemed daunting, and I told her so. She reassured me there was a vintage clothes shop off Oldham St and that if I needed help I could just ask her. We finished our drinks and I thanked her for the offer of help but was thinking that maybe bottling was a better choice.

Thursdays I always call on my mother for tea, we chat, catch up on what is happening, usually it is her friends and their age related ailments, or sometimes the TV news prompts a discussion, or I might have some news of work or going away for a weekend. In a moment of carelessness I mentioned that I had been challenged to dress as a women for a 80s night, without a pause she expressed her acceptance of me doing it, immediately asking how I planned on looking and how I was going to sort everything out. This took me aback some what, but tried to cover all that Hazel had mentioned finishing with a question about why she has no problem with her son dressing as a woman. Her reply was simple, I had lived alone for years, never had a serious relationship with a woman, had wrapped myself up in work and fitness, she had been expecting me to come out and tell her I was gay for some time, dressing as a woman for a fancy dress night in pub is no big deal by comparison. With that logic I had to agree but assured her I did not have a relationship with another man, and that I had not had one with a woman for along time, because that was the way I liked it in my full life. I steered us back to dressing, she told me she would ask her friends for anything they had got stored in their wardrobes, and that I should get some heels and try walking in them beforehand, also I should try having a dry run to see how it feels and make sure I have everything, besides which I might need the confidence a pre run might give me, a man going out dressed up to the nines might be a big challenge. I promised to heed her advice and get heels and some basic clothes to try on in the house, which satisfied her.

That was Thursday, next evening I called at a shoe shop on my way home and bought some plain heels, now I had an idea of what mum had meant about dressing up being a challenge. I was terrified, what might the other customers be thinking, and paying at the check out was so embarrassing, I was blushing all the time. But I could not wait to get them home and try them on properly, I had a pair of pop socks as suggested and the shoes were not slack on me. I found balance a bit off, but soon I had the rhythm of the walk pretty good I hoped. Then mum rang, asked me if I had got some shoes, I told her I was wearing them, good, she said. Her friend Alice apparently has loads of clothes, never throws anything out, if I picked her up in the morning we could drive over to her house and I could pick something. This was all a bit sudden but she had me unawares and I never said no to her unless I had a good reason to, and this time I did not.

I dutifully turned up at her house the next morning, and drove her to Alice’s, one surprising change to this pick up was that I was greeted with a kiss, something us northerners, this one in particular doesn’t do. Well Alice is a woman who takes the art of dressing to the extreme, she looked as if she was ready for a night out at eleven in the morning, her hair was styled, her clothes pristine and glamorous, and did not look bad for a 50+ maybe 60 year old woman. First we had a cup of tea while we discussed my needs, then we all went to a room I expected to be a bedroom but it was bedless, only wardrobes and chest of drawers, her sleeping must be done elsewhere as this room was purely for dressing in, something I had never imagined before. She opened a few doors and reached out a few items and the reality of what I might do hit me again. Was I thinking of wearing something like these in public? a nervousness gripped me, but mum must have sensed it and distracted me with plenty of ‘What do you think of this’ and ‘How big are you’ comments. Alice had stories it seemed for every item she showed us, different boyfriends or places were recalled with the clothes, and she had a lot. We had already looked at lots and there was a growing pile on a chair, it was Alice I think who suggested I try on one or two to see what colours suit me and how they hang on me. I was mortified, they wanted me to dress in front of them, mum picked up a few and bustled me into a bedroom this time, lots of lace and embroidered bedspreads as expected, but mum telling me to take off my clothes was not.

I did strip and she passed me items one at a time, a blouse, then a skirt, followed by a dress. Alice came in without knocking, I know it was her house but this was hard enough without a stranger walking in whilst I am part naked. Turns out we are very similar build, I am just a few inches taller, so her knee length is above the knee on me, but to me most things fitted, but after a bit of pulling at the shoulders or fluffing out a skirt it would be declared not quite right, that was until a pink outfit appeared, the skirt was full and stood away from my legs, the top in the same colour was a luxurious silk, sleeveless and full at the front as it crossed over about where my bust would be if I had one, there was a neat short jacket with square shoulders and lovely satin lining, I knew this would be the one, it fitted well and screamed female, this was made of fabrics men did not wear around here and the style was definitely feminine. Mum did suggest I get something to give me something up top, then on cue Alice turned up with a bra, pink satin, and a pair of big pants, she called them a girdle and told me she wore them when she put on a little weight and wanted to flatten her front out, not suggesting I was fat but she did observe that I had not got a flat front and bit of flattening would not go amiss.

It was mid afternoon by the time we had put the clothes into my car and thanked Alice for her help. I was about ready to drop mum off and go home, but she had different ideas, I would need other things besides a blouse and skirt, shoes to match for a start she insisted, and tights etc. So I took her to the shopping precinct where she was sure we would find what we needed. First she tried the charity shops, we did not find any shoes but she did buy a skirt and blouse at one, then she picked up some big bangles at another, and then she said it was a lucky find, a long blonde wig, the next one shocked me, a nightie, I said nothing but once outside she just stated that it get me into the right frame of mind for pretending to be a woman. I thought we were about done when she went to a cosmetic rack in a shop and had me try creams on my hand, then lipstick calmly telling me I have to get tones that suit my complexion. When I asked what else, she ambiguously just replied that we had done enough for one day. This was a relief to me as I needed a rest before I went out that evening.

I did get out and meet friends later, but not before I had put everything up in my bedroom away from prying eyes, and after I had had another more private feel of the outfit I had to wear, the silk was fabulous, and though I did not intend wearing it the nightie was really soft and sensuous, I could understand why women like wearing them and men like their women to wear them. So nice to touch.

As expected I bumped into several friends who wanted to know if I was going to do it next weekend, I replied every time, wait and see, I had not realized how many people knew about this challenge, but 53 had signed to buy me drinks so that was enough to be going on with. Then I meet up with Hazel, she told me she had borrowed some false tits and wanted to know if I needed anything else, I tried to be casual but I was not convincing as I thanked her for the tits, which let the cat out of the bag.

I did as mum suggested and practiced in the heels, even wearing the charity shop skirt in the evening whilst at home. A good blush was brought on by going to the shop where I bought the heels the week before, I found a pair of pink ever so strappy sandals in my size, and did not know where to look when I recognized the check out girl as the same as last time, I left wondering what must she make of me a man buying shoes, I pushed it out of my mind, I wanted to get home and try them on properly to be sure they fitted well, and they did. Only balance was an issue again, I had not noticed but they were higher and the heel a lot narrower almost to a point. So once again I practiced around the house in my new footwear.

Mum sounded pleased with my purchase and asked if I had been wearing them, yes, and the skirt/blouse, yes I had tried them on. She suggested I get online and find some websites about make up and grooming, then on Thursday we could have a run through, oh great I thought this was going to be another awkward time to be endured, I had to ask myself why I was putting myself through this, the challenge? the prize of money? drinks? or a smug satisfaction at seeing everyone’s face who thought I would bottle out?

So Thursday I have everything female with me when I call round for tea at mother’s, she does the kiss thing again, then gets me to show her all the things I have with me, she is particularly taken with the heels, very nice she said, and of the false breasts, interesting. She asked me to go and change while she made the tea.

I had tried the bra before and fastened it, then spun it round, next the pants, and my little used friend disappeared, next tights, again pleased I had played with them before so I had worked out the way to get them on, then Alice’s outfit, with a chest to fill ‘up top’ I looked far better, last the shoes, again I was glad mum had suggested trying them on and getting used to them before. I did not look in a mirror, just went into the kitchen to see what she thought, I got a very enthusiastic reception. Was told I looked great, very 80s, and once I had make up and wig sorted I would be perfect. She did suggest I go and change to eat as I would not want to stain Alice’s nice clothes.

Over the meal she came up with a few extra things I ought to consider, my legs looked good but hairs were showing through my tights, 80s was a time for long nails, maybe she could get me some false ones, and ear rings were big then, how about I get mine pierced. She made it all sound quite reasonable, but at the back of my mind was a concern that I might be too good and appear to like this dressing up a little too much. I listened to her advice and promised to remove my hair the day after, and maybe get sleepers in my ears on Saturday.

After tidying up, she showed me how to apply the make up I had, the foundation, blusher, eye shadow, mascara and lipstick, I had tried at home twice, but having a real guiding hand helped with things such as which way to stroke a brush or how to blend shades of eye shadow. Then she produced the wig, she had cleaned it and conditioned it so it was transformed into a very nice head of hair, then she explained how 80s was not flat and straight like the girls currently do, it was big, blow drying to give volume and spray to keep those big flowing fringes in place. She showed me with a water spray and hair drier how to get the volume, then hair spray to keep it there. She did say there were newer products like gel that she would find out about, but for now I had an idea how I could look, so I took a look in her mirror, I was astounded, it was still me, I had the same features, but the shoes and bust changed my posture and body look, the hair and make up hid my man head well. I was trying to work out how this happened when mum interrupted my thoughts by suggesting in put on the pink outfit to see it complete. And even she let out a wow as I stood jacket in hand and put a bangle on a wrist. Then she did it again, she hugged me and gave me a kiss. Now sons should not get this reaction off their parents after many years of no physical contact, but it was nice to feel her embrace, maybe I should get used to it, she clearly likes it.

We spent the remaining time teaching me how to walk, sit, stand, climb stairs, go to the toilet, touch up make up, check hair, talk and hundreds of other things I had never considered but she felt I should be taking into this costume night. And strangely I was enjoying the experience, the skirt was lovely, silk on my body felt great, the shoes were a challenge but interesting and the hair was so totally OTT and long enough to tickle my neck and shoulders, I was blown away with the sensations.

In time I had to appear happy to return to a more normal Karl and go home for what I hoped would be a good night’s sleep.

Friday was a distracted day for me, I had trouble concentrating on work my mind drifting back to the outfit, its sensations and the upcoming Saturday evening. But I got through it, went to the gym as usual, but once home changed into my blouse, skirt and shoes hoping to recapture the previous evening, but it was only a shadow of my evening with mum.

To calm myself I went for a bike ride early on Saturday as I was awake early, but mother was not taking the day easy either. When I got back a voice mail explained she had been shopping and was on her way over before lunch. I showered and got ready for her arrival. When she turned up I had rid my body of hair and was in my underwear and cheap outfit. Again a hug and she looked me up and down and smiled, ‘Bit early, expected you changing later, have you anything in mind for this afternoon?’ she had me there I had not thought this through.

I made her a sandwich while she showed me what she had bought, a chunky necklace, some big rings, a pack of glue on finger nails, nail polish to match the lipstick, and some enormous ear rings. I picked them up and looked at them interested how they worked. ‘They clip on but the others are for pierced ears which I think always look better, here try the clip ons’ a pain got my lobes as they clamped on and pulled down, I wondered about taking the plunge and doing something quite reckless.

‘So pierced are better?’ I knew that many men and women had studs in their ears, so it could not be that hard to do.

‘Well it takes time to heal the holes, but if you have sleepers, they are the small rings, you could hang some of the pierced ones off them. Interested?’

On a whim ‘Why not?’ soon I was changed, well at least my outer clothes and falsies missing, I was on a trip to the shops and soon to discover that the pain of something clamped to my ears was not in the same league as having a needle pushed through them. I should have used my head earlier and it would have been obvious, but one done I had to have the other done for the sake of symmetry.

Once home and the pain subsiding, my mother got out another gift a bottle of pina colada, very 80s she informed me and let me taste it, it was rather sweet with a rum kick but all the same it was easy drinking. And as we sat and chatted, the bottle got emptier, I guess I had three glasses but the effect was most relaxing, so when mother suggested it was time to get ready I easily went to my bedroom and removed my shirt and trousers wrapped a robe around me and sat before a mirror to do my face, mum I could hear bustling downstairs and then came up to see how I was getting on, she helped with the eyes, I was only asking for a little help blending the colours but she plucked what seemed like half my eye brows out as well. She said she was neatening up their shape, I doubted her somehow but the mirror did not reflect my fears. Then she brought out the wig, this time she had a spray instead of water, and once blow dried was not quite so firm as the hair lacquer, but she assured me would hold the style just as effectively. I was now looking the part besides the clothes. Next we went and sat in the lounge while she glued then painted my nails, she was onto a second coat when the doorbell rang. Hazel had come round to see if I needed any help, she was loving the scene that welcomed her of me sat having my nails done already, hair and face already looking the part, she too kissed me, I was thinking I must be missing out before. I offered a drink but she went and made a cup of tea and conferred with mum over what I had been up to.

We all ordered a delivered pizza and sat around watching me struggle with long nails and hair going in my mouth. Soon enough it was seven o’clock and time for the final stages, Hazel had a costume in her car and took the bathroom to change in, while mum helped me with my outfit, hung some ear rings off the sleepers, gave me the bangles and necklace, applied my lipstick and coated them with a gloss she explained would stop it wearing off, finally a dab of scent on wrists and neck. I was ready, the pink was quite a statement, as were the shoes, hair and face, but inwardly I loved this moment, I just felt special and attractive in a way I had never done before.

Hazel came out of her changing room ‘My look at you’ a definite look of wonder on her face, ‘Brilliant Mrs. Rose you have a beautiful daughter’ I could feel my cheeks blushing.

‘And let’s get a look at you’ mother added, Hazel was in what is best described as power dressing, sharp tailored suit with feminine blouse and a neat piled up hair do. ‘Very nice, I had something similar when I worked you know’ there was a pause ‘Now then Karl......Karla I suppose for this evening’ she laughed and hugged us both. I was rather overwhelmed by the situation, so Hazel took over. She offered to drive us to the pub, inviting mum along, and when she said she was too old for all that noise and dancing she offered her a lift home which she accepted.

I had thought stepping out my own door would be nerve wracking, but as three women walked out to Hazel’s car I concentrated on my walk, then getting into the car, and we were off, all distracting me from the possible gorping faces.

The night was great fun, music from Frankie goes to Hollywood, Culture Club as well as some Stranglers and other punk bands. My outfit did cause quite a stir, many not believing it was me at first until Hazel insisted she had seen me dressing. I had won my prize of not buying a drink that evening off John, and I had several names to claim a drink off over the coming months plus the money for the best outfit, I was on a high and danced with anyone, mostly women round the handbags, but at times with men who I suspect did it for a laugh, but Steve did dance a few more than others, and when it came to a Wham smooch he was close so I took his hand and lead him to the dance floor, which got us a round of applause.

As my alcohol intake was taking its effect and as my inhibitions lowered so did my memory. I woke in the morning with a great headache and to my surprise a warm body beside me in bed. As I came round other strange sensations came into my consciousness, there was hair in my face, I had a bust that I never usually had, my fingers were feeling weird as the nails caught on the duvet and poked my face as I pulled the hair from my mouth. As I stirred the body next to me moved as well and I got to see the face, OMG it was Steve, how did he get there. Then a new part of my body came into focus, my arse felt like I had passed the most enormous stole but with no recollection of a toilet visit and Steve sleeping next to me I feared that somehow I had had sex with my friend.

I got up from my bed and sneaked out to have a shower. I slowly came round with my image returning to a normal Karl shape. I was drinking strong coffee when Steve came into the room looking as though he felt like me, rough.

‘Was a great night’ it was a statement not a question.

‘Was it? Why are you here?’ I really did want to know.

He then explained why he had ended up sitting opposite me drinking coffee that morning. I remembered the pub, the drinks, the effect of the outfit’s success, the dancing and all the other fun parts to the night, he covered these pretty much as I recalled them, I did look the part, I was clearly enjoying myself, quite a few thought I was enjoying myself too much and fitting into the role of the outfit far too easily. What I did not know was how I got home. As things wound down Steve offered me a lift home, I accepted and apparently left holding onto Steve’s arm, drunk, I asked, enough to need help, he replied, but it gave an image that Karl would never have, he would have struggled rather than get close to anyone. Anyway Steve tells me that he drove me home, and I invited him in for a coffee, which he accepted clearly. What happened next was a surprise for Steve, and myself. Now I was listening. I made the coffee, then sat right close to him and started asking if I made a good looking woman, did he find me attractive, and I told him how much I had enjoyed the experience of the clothes and pretending to be a woman. I was running my fingers up and down his leg and what Steve described as being a positive flirt. I have never done anything like this before and was having trouble believing I could behave like this. So the drinks emptied and I continued with my flirting and kissed him, he obviously did not reject me and as Steve tells it the kissing got more passionate with me asking him to treat me like a woman, then I slid a hand inside his shirt, followed after a while by moving that hand to below the belt, Steve was telling me how keen I was and how my enthusiasm encouraged him to respond in like manner. Then I apparently stood up, took his hand and lead him to my bed where I asked him to take me like a woman, my sore arse is testament to the fact that something had been there, there was also some vague memory of an emotional moment, he confirmed this because I was telling him to screw me until I panted and ultimately screamed. He later told me it had been one of his all time fucks as it was unexpected and I was so keen for him to have me. The rest I know, we slept together and now we were drinking another coffee.

I had the evidence that Steve was telling the truth, but my mind was asking how did it happen, it was years since I had slept with a woman and I am not gay, so how? I asked Steve if he was gay as he must have not been repelled by me, a man in a dress, he described himself as bi sexual, so yes I was attractive and he knew what to do to make the sex work, his main concern was that we were mates and was not sure how I might be when I sobered up, but I was so insistent that I wanted to be the woman, he gave in a fulfilled my wishes.

Well what a revelation, I made Steve some breakfast and said our good byes, he did not touch me at all, I was distant in thought he told me later and felt it best to leave me be. Some parts of my transformation lingered, the sleepers in my ears, the false nails were still stuck on and my lips seemed redder than usual, but that could have been due to the rubbing I had done trying to remove the redness of the lipstick. There was no morning run, there was no afternoon drink at a pub, I stayed in and mulled over all that I remembered as well as what Steve told me. Hazel did call round later after she texted me to ask how I was, I knew I needed some help transforming back so asked her round.

We got the nails off, and she inspected me for make up after I had used a proper cleaner, we sorted the outfit for taking to a dry cleaner and tidied the wig, then washed the rest of the clothes. She also wanted to question me about how my night had been, I tried to be honest, explaining how much fun pretending to be a woman had been, and how nice the silk and satin fabrics are. She also gave me her version of how I looked the night before, according to her I was far too convincing, not 100% but very good, the walk and posture was particularly good, I clearly liked the attention I was getting, and was a different person. Far more outgoing, able to dance, chat and touch with ease. Then she mentioned Steve, she knew he was bi and thought I must as well because I was flirting with him, asking him to dance, giving him the look, well it is what she said though I don’t know what the look is, and when we left together with me linked to his arm several openly asked what we would get up to, and she was now there asking if we did get up to anything. I had a good answer without lying I said I did not remember getting home I was too drunk. She gave me a look that told me she did not know whether to believe me or not. But she did give me a hug as she left telling me she was pleased I had enjoyed my time in heels and a skirt, I hugged her back and thanked her for her help. Sunday over, work on Monday and get myself back to the routine I knew and was comfortable with. Well that was the hope.

Monday was not quite the relaxed atmosphere I hoped for, I wanted to keep the sleepers in my ears, it had been painful enough for me to think that I should have something for that pain, but as several colleagues came and complimented me on them, saying how they suited me, or how brave I was, one did make derogatory comments though which was not nice, but most were nice or neutral about them, but I could happily have done without the fuss, I just wanted to work undistracted, and that was not happening.

I trained, I worked, I tried to get over the events of the weekend, but they had been significant and deep, and questions about my sexuality and whether I was a pervert or not kept coming into my head.

I went for a quick drink on Wednesday, only to find friends who had not been there on Saturday telling me that they heard I stole the show I was so good, and if I did it again they would come along. This did nothing for my inner man who was getting quite a battering. Then on Thursday I went to mum’s as usual for my tea, I took all of Alice’s clothes and prepared myself for a different evening. First off she hugged me and I hugged her, which was nice. Then she recounted a tale she had heard from one of her friends whose daughter was at the 80s night, she had helped me dress so knew how I looked, now she knew how I behaved as well. She happily told me it was all complimentary, I must have gone down well and enjoyed myself. We chatted off the subject for a while but came back with questions about why I had the sleepers in, and would I do it again. I hoped she understood my reasons for keeping the ear rings, as to dressing again, I told her I had no reason too, but she pushed on with questions about whether I would like to if there was a reason, or maybe if there was not and it was just for fun. She had a most peculiar smile on her face when she was on the dressing topic, but most unsettling was the parting words. As we hugged she held me and told me she would always love me whatever I did, when I asked what she meant, she told me I knew what she meant.

Well it was all a bit too much for my manly ego, which gave in and accepted that it might be nice to consider the idea of dressing every once in a while if the opportunity arose, in the meantime though, I would sleep in the nightie. Then I found myself walking rather slowly past the cosmetic stand in the supermarket, and left with my usual groceries plus a clear nail polish and a pack of knickers. There was a certain thrill of buying them for my own pleasure and a good feeling of relief once I had left the store hoping I had not given myself away to anyone. These were just bought for the buzz and I did not use them really once I had them, I was not ready to go out as a man with knickers under my trousers or with varnish on my nails, but I had them in my small collection and that mattered to me.

I had my usual social life ticking along and mention of my outing diminished, as well as the people offering to buy me those drinks they had signed up for if I completed the dare. Then Steve rang me and suggested we go into town for a change, so we arranged for the next weekend and a new world was shown to me.

We arrived on Canal St which I knew to be the gay place to go if you liked that sort of thing. We drifted around the bars chatting and people watching. It was fun being surrounded by this circus of non conformity, same sex people embracing openly, women on hen nights feeling safe to be stupid, and every now and then a man dressed as a woman, Steve assured me there were some great ones you would never guess were men, some fantastic drag queens and some dreadful sights who had no idea how to dress but clearly enjoyed being out dressed as a woman. He also explained how the cross dressers were not all gay, many were straight, and some only fancied other dressers. All very confusing and hard to take in on my first real exposure to the full glare of different sexualities.

I was completely aware that Steve had brought me to this place so I could see what other people got up to and without saying it was opening me up to the possibilities of dressing again, and it was working, I could imagine myself coming to this place and having a good time. There were a few things which concerned me, one was what would I wear, I mean what style should I go for, would I look good in one of those sexy minis or should I be a little more normal woman type of look, and the last time I had lots of help, could I do it on my own. A deeper worry was the relationship with Steve, I had woken up with him and maybe he even fancied me without dressing, how would I feel if he took my hand as we walked down this street. I had to sort these out in my head first before going any further.

Steve knew a few people there and as we moved around was very easy with men who greeted him a bit more physically than I would expect in my usual pubs, he would then introduce me and after a while I got used to being greeted this way, maybe not as easily as Steve but certainly more contact than the handshake normally allowed between men.

Then I meet Shaun, he was as camp as a row of tents, his clothes and mannerisms screamed gay stereotype, he spoke like a gay should, and touched as a girl might, he was completely OTT. He came over to Steve and called him darling, then asked about me and took my hand in his limp fingers, at some time he found out that I was Steve’s friend who had gone down a storm at the 80s night, expressing his disappointment at not being there as he likes nothing better than getting all dolled up for a good night out. He left us after a while with an offer to get together one night for a proper girls night out, just the two of us, as he put it.

As we moved on Steve suggested I take up Shaun’s offer, I clumsily tried to explain I was not like Shaun, he was camp, I was not, he was gay, I was not, he liked being a girl, I liked being me. I then went to order drinks and got a mineral water with lime for myself, Steve quietly pointed at the drink, ‘That says it all’ I insisted it was healthy and I was not getting drunk that night, he just smiled ‘If you insist’. By the end of the evening and on our way home, Steve told me how much he had enjoyed the night, and thought I had too, when I did not answer positively he ran through the things I had been doing, like getting friendly with men, watching the trannies too much, hanging onto Shaun’s every word, and looking at men with what he called a longing look. Damn he had read me, I did like the closeness gay men had, I was thinking if I could come out dressed, Shaun and his offer had been great, and the men, yes I was looking and thinking and wondering what makes one attractive and another not. I lied and said ‘Maybe’ Steve then suggested he gives me Shaun’s number and that sometime soon we come down again, but that time with me as Karla and I can find out just how easily I would fit in with all these interesting people. I dropped him at his house, he asked me in for coffee. I declined. I had enough to confuse me without Steve pushing for a repeat of my last late coffee night with him.

That night my nightie had renewed significance, it made me feel very sensual and feminine, I hugged a pillow and imagined hugging Steve, 'and tomorrow I would call Shaun' was my last thought as I drifted off.

After my run in the morning I showered and then on a whim dressed in the blouse and skirt, then did some housework that I was always putting off. Then as I sat down later I found the number and rang Shaun for a nerve jinglingly awkward call. He was lovely and told me he would love to help me, if only to see what Steve had been raving about, I explained I did not have the outfit anymore, but he just told me to find something else that I liked and that we would have a ball next week. His idea of having a ball I suspected being somewhat different to my concept of a ball, but he said it in his way that he was just trying to tell me it would be fun.

I now had to seriously look for an outfit on my own, no help from mother, Alice or maybe Hazel, I would have to do this alone. I had some pink heels and a plainer black pair, besides that nothing to go out in unless you consider the cheap blouse and skirt that I had on.

I decided on a late night shopping Wednesday after work, and then if I failed I still had Friday and maybe Saturday. I had myself all psyched up and work was hard on Wednesday, but I found myself in the Trafford centre looking at shop windows, my mobile ringing made me jump as if someone was spying on my thoughts, and maybe he had, ‘What you doing?’ Steve was asking,

‘Shopping’

‘Thought so, just bumped into Shaun. Do you need any help?’ well that was that particular cat out of the bag,

‘Why are you offering?’

‘If you want?’ I paused weighing up whether to say yes,

‘I’m in the Trafford centre’

‘Be there in 20 minutes. See you at the food court’

And that was it he was on his way, I drank a coffee while I waited, several couples were shopping, but not too many male couples would shop for a dress, a sinking feeling of how embarrassing this could be flowed over me, I hoped he would not come, so I willed the clock to make him late then I could walk away and go home, but on 22 minutes as I was getting up to leave he appeared by my side.

‘Any idea what you are looking for?’

‘None really, just looking in windows for ideas’ fortunately he did not hug me or worse air kiss, but he did put an arm on my shoulder in a matey sort of way, which my nerves just about coped with. We walked along the shops commenting on what we saw, Steve liked the shorter styles, I preferred something with a bit more fabric to flow around the legs, but we both felt pink had looked good on me, and I had some heels so that made a start. Steve was more confident than me, he could walk along a rack, pick out an item hold it up, appraise it and put it back without a concern, whereas I felt everyone staring at me and about to shout ‘What is that man doing?’ I found a nice plaid, pleated skirt with lines of pink in the grey, Steve found a pink silk blouse which was full of ruffles on cuffs, neck and the button line. I paid for them and realized that this new hobby could be expensive. But before I left I needed lingerie, a girdle and bra like I had been lent, I tried to do this alone as I wanted a new nightie as well, I failed and Steve asked some personal questions about the nightie, I told him he should try wearing one they are very comfortable, this seemed to stop him, clearly he saw himself as macho man and he did not do soft and silk fabrics, but it was fine for me who maybe fitter and stronger than him to wear such flimsy items. I knew I would wear it that night and enjoy it, no matter what he thought. Though it did cross my mind later he would like the thought of being in bed with me and the nightie, but that was not one of my priorities right then.

Saturday evening came around and I nervously parked my car outside Shaun’s apartment block. I had kept myself busy all day doing extra work, going to the gym, anything to stop myself lingering on the suggestion this was a daft idea. Now I was there I had to go through with it. Shaun was as camp as I remembered, air kisses, hugs like we were long lost friends, all while wearing a white silk kimono. I had arrived. Quickly I was at ease, he wanted to see what I had brought to wear uttering words like divine or boring. I had been given my instructions on Thursday about preparations I needed to do like shaving my limbs and moisturizing. He soon had me changed into my lingerie and wrapped in a similar robe to his while we drank herbal tea and did my nails. Then he explained the art of make up while my face was transformed from Karl to Karla, last he brushed out my wig while it was on my head giving me tips on how to do this for myself. The time was slipping by and soon we were both nearly ready just our skirts to put on as it were. He had a gorgeous red sheath dress that fitted him like a second skin, knee length and unfussy but dead sexy. I in my pink blouse and skirt which my mother might have liked but looked dull by his side, ‘We will have to get you some lessons in style before long, you will have to ditch those tights and do stockings for sure, and with your body you should be a sex goddess that every red blooded man out there wets themselves over.’ He paused and took a long look at me, ‘You fancy Steve?’ I was shocked by this sudden change of topic, and unexpectedly felt my face flush a little, ‘That will be a yes then’ he clapped his hands and shouted ‘I knew it’ and went to his wardrobe ‘You can borrow this, make the most of those legs’ I removed my plaid skirt and stepped into Shaun’s, it was like mine in that it was pleated, but the likeness ended there, it was black and to me very short, but with the blouse it worked well. I looked like what my mother would have called a tart, but it felt very feminine and sexy. ‘You are going to give him such a stiffy he won’t be able to pee all night, now what do you think?’ Shaun stepped into his red super high heels and did a twirl for me, ‘Fantastic’ he looked disappointed, ‘Only fantastic, well I suppose that will have to do, but if I don’t get laid by at least one hunk tonight I am blaming you. And if Steve does not go weak at the knees I shall only blame myself. Now come on sister we have some men to hunt’

I had come thinking of trying cross dressing to see if I liked it, now I was being set up for a date with my friend. A cab took us the short distance to Canal St and adventures into a new hobby continued. Sheena, Shaun preferred it when dressed, was even more flamboyantly camp than before, he left no doubt that he was a trannie albeit a very convincing one if he toned down the mannerisms, I followed in his wake enjoying the delights of unsteady walking in heels, the freshness of cool evening air on legs, the brushing of long hair on my face, the bounce of weight suspended in a bra and the soft feel of silk on hairless skin, all of these sensations breezed through me, Sheena was chatting and introducing me to several men, some dressed like we were, others in their dull male trousers. I was being chatted up by a few of the trousers and drink was something I never had to think off, if I went for my purse someone would ask what I fancied.

Sheena found Steve and presented me to him. ‘For you, one sexy goddess, now you two love birds get lost’

I leaned into Sheena for a hug ‘Thanks, not sure what you have got me into, but thanks’

She hugged me back and whispered ‘if I was him I would be dreaming of getting into your knickers, make him wait and make him pay, but don’t forget to tease him, keep him interested’

I blushed ‘I don’t know what you mean’

she laughed and kissed me at the same time as squeezing my arse ‘I bet you don’t. Now get lost I want to find a tent pole to satisfy my hole’

Steve asked what we were laughing about when I returned to his side, I told him it was girls talk and kissed his cheek which was the start of a night I would try to recapture in the following weeks. I was hungry so he took me for a Chinese meal, then we danced and drank until late and then took a taxi to his house where we had the traditional coffee before taking me to his bed and in my expectant and relaxed mood, let him make love to me. This time I remembered it and enjoyed a lovely orgasm which left me knowing that I would need to do this again, and fell asleep in Steve’s arms.

Come the morning there was a text from Sheena

Was it a good night?

Yes

You with Steve?

Yes

See Karla next weekend?

Yes if you don’t mind have a novice with you again?

Off course not sister, you are one of us now, you will never go back.