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.