Date: Wed, 19 Apr 2000 23:06:16 -0400 (EDT)
From: Aby Over <aby@cutey.com>
Subject: New TG Story -  Abi-Night_Out

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 crossdressing 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

Story Four
Abi - Night Out

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 15 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 my hair or muscle but some build up on my chest.  With curiosity I pushed
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 the 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 few months ago'
'Oh I'm sorry'
'It's alright, 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 15 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 surfisticated'
'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 on of the back roads behind
one 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 nock 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 George my benifactor in this transition 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 oldish 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 15 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 15 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!'


The End
Hope you enjoyed my little piece :)
Abi xxxx

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