An Abi Story

This story is free to distribute so long as this introduction is kept in full. The aim of the my stories is to show a positive or more caring side to transgenderism. I myself believe that there are too many stories out there that involve violence, harm or forced cross dressing as a punishment which I do not like for the message that it gives to those unsure about there sexuality and may be given to believe that such a lifestyle only gives them the right to be punished and feel guilty for simply being themselves. And so you will not find violence or punishment in these stories, but that is not to say that they are not intended to be sexy!!

All your comments or ideas are well received... aby@cutey.com

 

Night Out                    by: Abi Over

 

I was just sitting there in the cafe during school lunch break, Joe had said he would meet me at about one o'clock, but there was still no sign of him. So I sat there leafing through some work that I was meant to have done weeks ago for that afternoon's class, same as always there then! If Joe didn't turn up in the next five minutes I would set off for school without him. Those five minutes came and went and still there was no sign and he didn't seem to have his mobile turned on, damn fool. After one last look around the small bar I grabbed my bag and headed towards the exit. It was on the way there that my path was blocked, a middle-aged man in a suit, probably aged around his late-30's stepped out in front of me. It was the same man that I was sure had been watching me whilst I eat my lunch, but I had put that down to simple paranoia. Though once the guy realised he had blocked my way he was all apologetic and held the door open for me. Giving him a quick thanks and turning towards school the incident didn't really enter my mind again, I was too worried about this afternoon's work and wondering where Joe had got to.

The walk from the local cafe, one of the many that people from school spent there lunch breaks, only normally took a few minutes though having just left the 'door man' suddenly appeared at my side and smiling said

'Hi, I'm George'

'Ermm...Billy'

I replied not being sure why he was talking to me.

'I've been watching you in that cafe and was just wondering if I could ask you something'

The guy seemed normal enough, not some kind of psycho.

'Ok, what?'

'Well I know you've never met me before, but I'd like to ask you to accompany me to a ball on Saturday night'

'Pardon, did I hear that right??'

'Yep, a ball, as my companion'

Out of all the things that I thought he might ask, this was defiantly not high on the list!! a ball with a bloke I'd never seen before, and of course there was one other 'little' point:

'Don't you normally take women to a ball?' I inquired

'Well that was what I wanted to ask you about, I mean what would you say to a thousand pounds to come with me as my partner?'

'But I'm a boy, why don't you get a girl or even a proper woman?'

'Ok three thousand!'

I was trying to get this straight in my head, a stranger was wanting to pay me £3000 to become a woman and go with him to a dinner party on Saturday night, I must be missing something here surely!

'Three thousand?' I echoed

'Alright make it five thousand, what do you say?'

'Are you serious, this isn't some wined-up, did Joe put you up to this?'

'No I'm deadly serious, I want you to accompany me to the local dignitaries ball this Saturday'

I still couldn't work out why he would want me, a 14 year old boy to become his partner. Deciding it was probably some get-up or the guy was a complete weirdo I responded:

'Let me think about it, ok?'

'Sure, here have my card, call me when you decide what to do'

And with that he walked away back towards the cafe. It had to be said that that was one of the strangest encounters I had ever had, but the idea did make me curious. Me as some done-up lady in a beautiful dress, I mean ok I didn't really have a very masculine body but I had assumed I would 'fill-out' later. Why did this guy, this George, want me?? With these differing thought going through my head I continued back to school and that un-done work.

Later after school. The whole George episode now seemed distinctly weird, but had occupied my attention all afternoon meaning I didn't get much work done! It was whilst I was getting changed out of my school stuff that I noticed myself in the mirror of my bedroom. I defiantly had a small, in fact quite feminine body, without much hair or muscle but some build up on my chest. With curiosity I pushed my chest together and up, it did make a quite convincing cleavage, albeit with a very small breast-age. Maybe George had 'chosen' me because I had this feminine look to me, though had it not been for his inquiry I probably wouldn't have given it a second thought.

Having put on some old clothes I got on this my jobs around the house, tidying up and thing before my mum got back from work. All this time I kept thinking what it would be like to dress-up in a night dress and stuff, with the figure of £5000 of course also weighing on my mind. Once mum got home and we had dinner I went to my room, with the idea of doing some homework, though naturally George's request dominated my thought. After a few hours of thinking about it I decided to give him a call, yes it was to turn him down, of course it was to turn him down, I mean I'm a boy for heaven's sake! Picking up the phone by my bed I dialled the number and waited for an answer. Quite quickly George answered, and I told him who I was.

'Oh hi again, have you thought I about my offer?'

'Well I've been giving it some thought and five thousand pounds.'

Before I could finish what I was saying he had interrupted me:

'Ok ten grand'

He really did seem desperate to pay me money to do what he was asking.

'Ten thousand' With that I made a snap decision, the thought of ten grand and what I could do with it

'Alright I'll do it'

'Oh marvellous, great, I was hoping you would say yes, now why don't you come round here on Saturday and we can work things out, sound ok?'

'Yeah fine' I replied starting to wonder what I had got myself into.

With it being Thursday, that meant that I had two days before I went to George's house. From the address on the business card I was over the other side of town, the well-to-do area. All Friday I still wondered what I was I had said I would do, if I took a minute to stand back and think about it I was being ten thousand pounds, ten thousand that was enough to get me a decent car or put me through university admittedly I was only 14 and such things where not really important at the moment, but that amount still scared me a bit.

By Saturday morning my mind was set, I would go to this house and see what George was really on about, he would probably admit it was all a joke and I'd feel stupid for falling for it but what the hell. Not wanting my mum to know where I was going, how was I supposed to explain I was going to see a strange man about me dressing up as a lady and going to a dinner-ball?? I ordered a taxi from the centre of town. All the way on the drive there I was starting to worry, what if the guy was really a psycho and he lived in some mad house!! Ok clam down, I told myself, the address was at least in a decent part of town, not some out of the way place. As the cab driver pulled up out side the house I realised I had been even more wrong when I said it was well-to-do, the place was a small mansion. With a long drive and posh car parked outside I could see why George was willing to just up the offer in a second, ten thousand was small change to him from the look of the house!

Apprehension still dogged me was I made my way up the drive to the imposing front door. With the ring I almost expected a butler to answer it, but George himself came to the door and warmly welcomed me in.

'Oh I'm so glad you came, would you like a drink of some thing?'

'Err sure whatever you've got' Knowing he'd probably have every drink ever invented.

'G'n'T ok?'

I really did have the nerve to say I had not drunk much alcohol before, so accepted his offer and followed him into the dinning room area.

'Ice and lemon?'

'Sure' not really being what it was I was saying sure to!

'Could I just ask you something first though?'

'Anything'

'Why do you want me to become your guest to this ball tonight? I mean looking round I'm wondering why you don't ask some high-class lady or something?'

'Well Billy, I'll tell you the truth, you see my wife and daughter were both killed in a car accident a last year ago'

'Oh I'm sorry'

'Thanks I’m alright now , but it's just that when I saw you in the cafe on Thursday I realised how like my daughter you looked, in your build and face, and I instantly thought what it would be like for you to wear one of my Debi's lovely gowns, and what with the ball tonight I decided to ask for an additional favour as well'

'So you want me to dress-up like your daughter?'

'Well I thought her clothes and things would fit you so well'

It seemed then that George was offering me money and supplying all the 'equipment' as well. My curiosity was really working now and after drinking my gin and tonic we headed up stairs to Debi's old room.

George's daughter had obviously been well catered for, with a posh bedroom and upon opening the wardrobes it was clear she had really been one for fashion as well.

'Now I know there is a lot of stuff here, but as its for a dinner-ball I think you need to choose something elegant, if you know what I mean'

'There's so many pieces here!'

'That was my Debi, always buying clothes!'

The searching through the seemingly never ending wardrobe eventually produced what I looked the most glorious dress in there, I suddenly stopped myself though and thought what I was doing! I had decided upon a dress as I thought it was pretty and kind of sexy at the same time, what was happening I was a 14 year old boy! Some I put down to the unaccustomed drink, my head defiantly wasn't straight at the moment, but I still had a real urge to try the dress on, to see what I would look like wearing it. I turned to George to present my discovery, it was a dark green silk work, with a long flowing skirt and string straps around the shoulders. The one part that I was not sure about was the quite low cut front, which was meant to show a bit of cleavage, but I remembered back to Thursday night and what I had managed to create then.

'Nice choice Billy, do I really have to call you Billy, its not a very feminine name'

'Ok how about Abi?'

'Well for this evening what about Abigail, sounds more sophisticated'

'Alright' Again I could believe I was agreeing to this!

'Now before you try that gorgeous dress on Abi, I think we need to go for a little journey'

Getting into George's plush car we drove back towards town, I wasn't sure where we were going as he wouldn't say. We eventually arrived in one of the back roads behind the high street. George lead me to a doorway, one that I had never really noticed before, inside I was amazed by the place that the unimpressive entrance hid. The sign on the wall informed me it was a beauty clinic, though I had never heard of anyone going here before. George introduced to a slightly older woman, calling me Abi all the while. He told her what it was I wanted, and promptly I was taken into a small cubical.

'I'm Susan, now George said you wanted the full works to day, is that right love?'

'Erm yeah I think so'

'Right well lets see what we can do shall we'

She smiled and asked me to take off my clothes. All the time Susan was very kind and helped as I shaved what little hair I had on my body and applied some light make-up to help show my girlish face. The most attention was on the hair on the top of my head. Although not short my boy's hair was not long either, but defiantly would not look right on a young woman.

'I think we will have to put in some extensions, what do you think Abi?'

'Ok, if that'll work'

Again I had just agreed to something without really being sure what I was letting myself in for, but by this time the whole experience was something of an adventure, and you don't get to go on many of those by the time you are a teenager! We decided on short, black hair. After a while of Susan working on my head and waiting for it to finish, I returned to the waiting area where George has been sitting.

'Wow what can I say Abi!'

I now had smooth, black hair down to just above my shoulders, with parts hanging down in front of my face, covering my right eye in a very sultry, sexy manner.

‘What you think then George?'

Asked Susan as she returned after clearing up.

'You really will be a knock out tonight Abi!!'

Although part of me was saying I should not be hearing compliments off this older man, let alone accepting them, I really was feeling great with all the encouragement that George gave.

'Thanks' was all I could manage as he walked over to Susan, all the time keeping his eye on me. I headed to the door feeling defiantly different from when I had woken up that morning, whilst my benefactor paid for the treatment and accepted some other packages. On way back to the car I looked around to see if anyone would notice me, this boy with a good-looking girl's head on his shoulders, thankfully there was no one about. All the way back to George's house he kept looking over to me, admiring the work that his money had paid for.

As the ball started at 8pm we only had about an hour to get everything ready. I returned to Debi's room, and again could not believe the image that was looking back at me in the mirror, I mean if I saw this girl or even a lady like this for myself I would be so turned on. Though there were of course some things missing from Abi, most notably a chest! It was at this point that George produced the contents of the packages Susan had given him. The main lot was a kit to create a realistic cleavage, from the chest I already had. By different methods of tape and breast forms there was eventually created a pushed up effect with my natural chest forming a convincing cleavage and a with a good bra on you could not tell the difference! It was not the largest chest in the in the world, but for girl of my height it was ideal! The other 'present' that Susan had given us was a get-up to deal with my 'man-hood' shall we say. By pulling my in fact quite unimpressive part behind me and keeping it there, and with a nice pair of lacy panties I gained a decent female frontage as well. At this point George left to finish getting ready for my big night out. With my newly shaved skin the silk of the green dress felt divine against my body as I dropped it down. A pair of black high heels and a evening coat completed ‘Abi’.

Soon George was back wearing his smart tuxedo, and the look on his face when he saw the finished product!!

'God you look so gorgeous Abi!'

'Why thank you, you look quite good your self'

It was good that my voice had not yet broken, as the female image was perfect. After a quite kiss on the cheek George linked arms with me and we set off to my very first ball.

All the time he was a perfect gentleman, holding doors open for me and helping me in and out of the car, which was difficult given the length of the dress. Pulling up to the large country hotel I could see that there were other equally attractively dressed ladies at the dinner-ball. I naturally felt a bit apprehensive as we walked arm in arm through the great entrance hall, what if my true identity was to be discovered! At least the announcer was convinced as he informed the gathering of 'Mr George Merton and Miss Abigail Winton'. I defiantly felt like a fish out of the pond was we mingled with the other worthy guests, each of them complimenting me on my dress and appearance. Only a few gave me a slightly strange look, but George assured me that they were surprised to see an old-ish man like himself with such a young and pretty date! At many moments of the evening I was sure that there were other men around the huge hall looking at me, many of whom had attractive women with them. As we socialised, me pretending all the time to be a wealthy young woman, I continued to drink many untried drinks. As the night went on I'm not sure when it was that I finally admitted to myself how great I was feeling, being this young popular socialite, not an average 14 year old schoolboy, but the time came as I was dancing with George that I realised that I had start to look back and admire the younger men around the hall who watched me. I was no longer looking at the attractive women in her elegant night-dress, it was the tuxedoed guests that caught my attention. Various dances, mostly slow ones, and I felt at home in George's arms. I began to really get into the role of his young date and pushed myself against him, feeling the warmth if his mature chest on my own.

'Are you enjoying yourself Abi?'

'Defiantly'

I replied and reached up at that moment and kissed George straight in the lips. Not to my surprise he responded passionately, moving his hands up and down my bare back as we kissed and danced.

'Look Abi, I know we said ten thousand for tonight, but what would you say to some more for some extra favours??' The tone of his voice belaying exactly what he meant. Whether it was the drink, or the atmosphere or even the dress and hair, but I replied enthusiastically:

'I was hoping you would say that!'

After some more dancing and socialising we make a quick get-away before the end of the night and headed back to the car park. As soon as we were outside I turned to George and kissed him again on the lips, this time even more deeply as I let him work his hands into my small backside. Eventually breaking off we continued towards his car. Helping me in to the passenger seat I noticed George staring down my dress, and looked back smiling invitingly.

The drive to his home seemed to last for ever, with us both desperate to arrive. As soon as we got to the front door there were hands all over each other again, still part of me was saying that this was a man, an older man at that, probably old enough to be my father, and I was a boy, a 14 year old boy, but I really didn't care now. We almost ran up the stair, longing to express your desires. We at last parted at the top of the stair, where George when to his room, after I had undone his shirt and tie, whilst I went to get out of my long dress. Pushing up my cleavage again I pulled on one of Debi's sexy purple wraps and almost ran to the master bedroom. Opening the door I found George waiting, crossing the floor our lips met again, and I unbuttoned his suit trousers, running my feminine hands into his works. Untying the wrap and revealing my chest George took my girl's breasts into his hands as we headed towards the king-sized bed. Lifting me up in the air he set me down onto the soft sheets, playing with my woman-hood and cute backside.

'Abi are you sure about this'

He asked as I removed his male briefs, releasing his straining piece.

'Of course I am'

I replied as I rolled over onto my front and worked myself into a position ready for him. Removing my small panties and taking my cheeks into his hands and working cream into my 'virgina' George kissed me on the neck and entered me. The sensation was amazing, the feeling of his own inside of me, pleasuring me and his self. We moved in motion together, his male chest rubbing up against my soft feminine back, his hands holding and needing my breasts. My own member was working, with the pure pleasure almost to much to bare, as he released it from it bonds we both exploded in fulfilment. At last we turned to face each other, smiling at what we had done.

'About the money lover' I said

'I will pay, I said I would'

'No I was going to say you can keep it, I think Abi has got reward enough!'

 

 

Epilogue

......I now knew that Billy Newman, typical fourteen year old teenage schoolboy was in for a challenge. Abigail Winton, high-class socialite and her thirty-something lover and benefactor George Merton had had a definite night to remember. As I lay there in the arms of my rich partner the idea of having to return the dull life I had lived for the last 14 years was certainly not attractive, what was I going to do????

The next morning I woke to find that George was not there, pulling on a pair of his daughters silky knickers and a gown I wondered down the grand stairs, the memory of what had happened the day before causing serious confusion to say the least!! With my head still spinning a bit thanks to the drink I walked into the kitchen to find my new lover cooking a whole breakfast:

'Oh you're up gorgeous, I was making you breakfast in bed'

'Sorry'

Putting down his pan George moved over toward me and kissed me straight on the lips,

'Are you alright this morning then....'

'Err yes I think so, did we really do all the things I think we did last night??'

'Well yes, though I'd understand if you're a bit confused at the moment'

I was defiantly confused, but having looked at myself in the reflection from the shinning worktops and the image of an attractive young woman looking back reminded me of the situation I was in, I was now Abigail Winton. Eating breakfast any idea about where to go from here seemed unclear, I couldn't exactly go back to my mum looking like this and tell her where I had been all night, could I??

'Why don't you have a bath, it might make you feel better'

George suggested. Returning to Debi's old room, with its feminine style and sexy outfits the thought of staying here and living as a girl seemed appealing, but no I was a boy even given my present appearance!! Soaking in the warm bath water for what seemed like an age, surrounded by all of the finest belongings I came to the conclusion that maybe I could live both my lives, being a boy during the week and a young woman at the weekend.

And so from there that was what happened. I would tie back my silky black hair and attend school Monday to Friday, and then with the excuse that I had got a job that worked late I would become Abi on Saturday nights. Going to dinners and balls with George, which were followed by the customary loving-making, Abigail Winton grew to be a major member of high-society. I would turn up to events and heads would turn all around the room!!

 

The End

All comments gratefully received...aby@cutey.com

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Written by Abi Over, April 2000

Epilogue added November 2000

 

© 2000
The above work is copyrighted material. Anyone wishing to copy, archive, or re-post this story must contact the author for permission.