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

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.’