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

 

Male-Waitress                        by: Abi Over

 

'Simon could I just ask you a favour?'

That was the question that started it all. I had been working at the restaurant for a few months now as a your usual waiter, taking orders, serving drinks and that kind of thing. But when the boss, Anne, asked me to do her a favour it was one of the last things I imagined....

The idea of dressing in the 'wrong' kind of clothes was an area that I had never really given much thought until recently, with the other typical thoughts and experiences that a young teenager goes trough at my age. I had never been the most masculine of boys, but had always seen myself as a pretty normal kid, though that would change!! The job at the restaurant down the road from me paid well, about £5.00 an hour, so well above the rate that my friends would get, who hardly made minimum wage. Admittedly it cost me my weekend nights, but at that age (going on 15) there was not much to do round where I lived. For all the money that I was making there were a few things that I seemed to do without, most notably a haircut!, as my blonde-brown hair was down past my shoulders by this time, and I would have to tie it back for work and school. At the restaurant there were a few of us on the waiting staff, with at least two working each night. Anne had always insisted on there being an even number of girls as boys at all times. It was that wish that would cause her to ask me question. Usually when I worked on a Saturday night there would be me or Jim as well as Julie or Rachel on table waiting, but the night before this particular Saturday Anne told me that she was unable to get Julie or Rachel to work (apparently Julie was going on holiday and Rachel was off sick in bed). Not wishing to be short of numbers Anne asked me to work as well as Jim, which I naturally thought meant the two of us as waiters. However she had a surprise in store:

'Well Simon you know that I have always had a balance of waiters and waitress every night'

'Yeah I've noticed that, but I you said that Julie and Rachel couldn't work'

'That's why I wondered if you could fill in for them, for you to be a waitress for the night'

'Sorry what did you say, you want me to be a waitress??'

'I know it's a strange favour, but I've tried everyone I can think of and there's only you and Jim who can work tomorrow.'

'But why me?'

'You've seen Jim, he's not exactly waitress material is he'

She had a point there, Jim was nearly 6ft tall, as opposed to my 5ft 2.

'Also you have nice long hair and the right build for it, please I'll be so grateful, how about triple wage, say £15 an hour'

Anne said as she smiled longingly at me. Now this isn't the kind of thing that you get asked to do everyday is it! The idea of making about a hundred pounds in one night defiantly appealed, but idea of dressing up in girls clothes and serving people I was not sure about, I was especially wary when I considered the kind of things that a waitress had to wear, usually a short skirt and light blouse (I have to admit to having spent numerous hours at work 'admiring' the look of either Julie or Rachel!).

'I will help you with getting ready tomorrow, we'll make a great waitress out of you I'm sure!'

Anne attempted to encourage me. In my head the dilemma was ticking very fast, and there was a definite curiosity factor there, a desire to find out what it was like to be a girl, especially in such a feminine role. After a bit of thinking I decided:

'Ok I'll do it, but you'll have to help me out'

'Sure, now just for starters I don't think you can really have a waitress called Simon can you, what do you want instead?'

'How about Abi'

It was a name that I had always liked, and Anne seemed to like it also, and so Abi the waitress was born!

I agreed to go round to Anne's house a few hours before I was due to start work to get ready. On the walk home the implications of my decision began to sink in, what would others say what the main problem on my mind. Upon reaching my house I told my mum that I had to work the next day, but happened to miss out that I was working as a waitress! With the different thoughts and conflicting ideas in my head I went to bed that night, part of me not being able to wait until tomorrow.

After a usual Saturday morning, homework, helping round the house etc, it came time for me to leave for Anne's. My mum was a bit curious why I had to start work so early, but I simply told her that there were a few things to get ready for the restaurant, which was almost the truth! On the way over to Anne's home the conflicting thoughts were still racing through my head: What was I doing, I was a boy and boys don't dress like waitresses, but again the curiosity and desire got the better of me and I continued on my way towards being Abi for the night.

'Ah you're here, good then lets get on with it shall we Abi'

Anne smiled to me.

'I've been getting the clothes and things together, I even when all the way to Manchester this morning for one special piece!'

That 'special' piece turned out to be a pair of silicon breast forms, to help add to the effect. Anne seemed to have defiantly put a lot of effort into this plan. I followed her to her bedroom where she had laid out the typical 'uniform' of a high class waitress: short black skirt, white almost see-through blouse, black tights and formal shoes. But the things that caught me eyes the most were the pieces of quite sexy underwear that Anne had got for me to wear!

'I've been looking into this shall we say cross dressing idea and come up with some helpful tactics'

By this she meant to hide my manhood from the world in effect.

'Right lets start, you'd better take off those boy's clothes Abi'

I had never been fully naked in front a woman before except my mum when I was little, especially not a woman of Anne's 'quality', but I was going to do this then I suppose that being naked was going to be one the least challenging aspects, so I began to take off the jeans and t-shirt that I had come in.

'Ok for a teenage girl, you do appear to have a bit to much hair and boyish features'

And with that I followed Anne to the bathroom.

By this time the desire to try out being Abi was firmly in control as I let

Anne shave what body hair there was on my legs and chest. Also she washed my long hair well, it was amazing the effect the conditioner and other products had on my usually quite matted hair. A quick bit of care and my skin appeared to be softer, more feminine.

'Just a bit of perfume I think, some thing fresh and womanly'

After all of this pampering in the bathroom I returned to the bedroom feeling like a 'new woman'!!

'Right time to try something I read about'

Anne looked down to my relatively small maleness, but it was still out of place for Abi. She took it in her soft hands and with a bit of effort tied it down between my legs, it was not exactly a comfortable position but did give the flat front of a teenage girl.

'That's the bottom sorted, now for the top'

She smiled and reached for the breast forms, they were not the largest size that I had ever seen but pretty generous for a 15 year old girl!!

'I know we could use an adhesive to fix these in place'

'But that would be permanent wouldn't it, I have to go home tomorrow!'

I expressed, that was actually the first time that a sense of reality came to my mind, that I had to live with the changes that she was carrying out, but the hair would grow back I supposed. So we decided to simply hold my new breasts in place with a the bra. The bra itself was quite lacy, with some sexy patterns on them, but hopefully full enough with hide the fact that my breasts weren't real!! Strapping me in Anne stood back to admire my new chest:

'Well Abi I think you will defiantly be catching a few eyes with those to night!!

That was the kind of line that made me worry, did I really want to be catching people's eyes, but also I seemed to excited by that idea, that I might be able attract people's attention with my appearance. Anne handed me the matching briefs which were also quite lacy but with a white impression of innocence to them. Next came the make-up and hair styling, which left me with a ponytail and bangs down the front. Anne still hadn't let me look into the mirror yet so when I did get a look at the new Abi it was amazing, the transformation from average, plain looking boy to teenage girly stunner was unbelievable. The clothes of a waitress came finally. The black tights made my legs seem somehow longer, more shapely, especially with the short black skirt which only reached to my mid-thigh. Add the white blouse and formal shoes and the waitress was ready.

'What do you think then Abi?'

'Well I'd catch my own eye if I saw myself!!'

'Thankfully your voice has still not fully broken, but a bit of training and I reckon that Abi with be ready for service'

For the rest of the afternoon Anne showed me how to work as a waitress, and walk like a real girl.

It at last got to 6pm and we headed over to the restaurant. So far I had only shown myself to Anne, but that bound to change over the evening.

'Are you ready Abi?'

Anne asked before we got out of the car

'I think so, lets go'

My nerves at what the other staff would say was building in my stomach as we walked to the door, would they laugh at this attempt by a poor boy to pretend to be a girl, would they see my real identity straight away. As it turned out Anne had told most of the staff what was going on, and thankfully they all acted warmly towards Abi. I was simply told the same as usual in the waiting service. The difference came when Jim arrived, being the only other person there aged under 20. Although Jim was no male-model he had not exactly been hit with an ugly stick either, but it was not a matter that I gave much thought to before. For some reason as Abi I noticed many of Jim's attractive male features, his square jaw, his manly build, it was clear why Anne had chosen me over him to act as the waitress that night.

'So you're Abi then, well hi I'm Jim'

He started with, as if he had never met me before

'Come on Jim you know its me, don't you?'

'You mean you're also Simon, but in front of me is an attractive waitress called Abi'

With that came a boast, a compliment can so help a girl's confidence! As so we began to get on with work, doing my usual jobs. Once the customers began to arrive I started to wonder, how many of them could tell that I was not a real girl, I was the same person who had served them before, only as Simon not Abi. But the one difference that I became aware of was the treatment that they afforded me, especially the male diners. Not longer was there the simple ordering of food and acknowledgement of service that Simon received. Now Abi was gaining attention, people would thank her and look into her eyes (with some private thoughts on their minds??) Being conscious of the clothes I was wearing it quickly became clear that men enjoyed the time I was around them, with my bra easily visible and my short skirt not hiding much around my waist. At one point I had to bend over to pick up a fork that a customer had 'accidentally' dropped, and with a sudden streak of manipulation I showed my admiring public what they wanted to see, letting my skirt ride up my legs and a quick fast of white as well as allowing my blouse to open to those in front of me. This little presentation which only lasted a split second seemed to catch the eyes of many of the men in the restaurant, the majority of whom had female partners with them!! With that I began to realise the power that I could have over these people, by the end of the night I was looking into the eyes of many eaters and hinting at some more, some they obviously wanted but could never have, especially if they knew my real identity!

But as well as the customers that night I also noticed the attention of one other person, Jim. At any moment that he could he would be looking at me. I wondered if it was simply a curiosity that I was the guy he had know for ages, or if he was looking at Abi as a girl, as he would look and admire any other attractive female. As the night began to draw to a close and things started to quieten down Jim came over to me:

'Hi Abi, I know probably want to get home but I was thinking we could go for a walk or something after we finish'

It was immediately clear what he meant, again there were conflicting messages in my head, on one side it was telling me that I was really a boy and that this night had been strange enough as it was, but on the other there was a real sense of excitement, of longing to see where it would lead. Naturally the latter won out and I agreed to let Jim walk me back to my house, with that he began to turn away but as he did brushed his hand over my backside and smiled. I smiled back and to myself also.

For the rest of the night I was in rapid anticipation, with a desire to see what might happen on a simple walk home. Anne must have seen our exchange, as she came to me later and handed me her keys, whispering in my ear:

'Here Abi, I'll be staying at John's tonight, there's drink in the kitchen and protection in the bedside table!'

It became immediately clear what Anne had in mind, what she thought I wanted, and it was in fact the best thing she could have told me. With that I almost ran to Jim who was getting his coat.

'Are you ready to go Abi?'

'Defiantly'

As he opened the door for me he asked 'So where is that you live?'

Abi then took control over me, saying that I lived with Anne and that she was out for the night. Jim seemed a bit taken a back by the implication that I was hinting at but instead of reacting badly he smiled and put his arm around my shoulder, letting me feel his warm body. We chatted on the way to my new house, almost running at some points with a desperation to reach the possibility of fulfilling ourselves!

'Here at last'

I smiled as I unlocked the door and let Jim into the empty house. I took his slightly hesitant hand and lead him towards Anne's bedroom. Kicking the old clothes of my previous life a side whilst I put my arms around Jim's neck and kissed him passionately full on the lips. With a desperate movement his hands ran up my legs and under the short black skirt that barely covered my pert backside then unclipping it, at the same time I undid his tie and slide off his shirt revelling a great body. We eventually broke off and stared into each other eyes before Jim lifted me off my feet and carried me to the large double bed, I unbuttoned my blouse as Jim removed his trousers. The feel of the silk bed sheets on my bare back and legs was completed as he pulled down my lace knickers to reveal my semi-womanhood.

'Have a look in the draw' I whispered as I rolled on to my front, showing my virgin hole to Jim.

'Here we go Abi!'

And he drove his self into me, with spasms of pain and pleasure I moaned encouragements as Jim pushed harder and harder. The tape holding my own sexuality in place could no longer manage and I burse out and exploded with desire.

'Oh god yes'

I screamed as Jim finally filled my new pleasure hole.

'Abi that was great'

With that we turned to face each other again and smiled for what seemed like hours. All of a sudden Jim kissed me quickly and started to grab his stuff

'I've got to get home, I will see you again won't I Abi?'

'Sure lover!'

Jim eventually got dressed after much distraction and left for home. I looked around what had become Abi's new home and smiled to myself. With thoughts of Jim on my mind, and not much thought about tomorrow I fell asleep on Anne's huge bed.

I was woken by the sound of the door bell ringing, grabbing a purple silk dressing gown from the wardrobe I ran down to let Anne into her own house. The look on my face must have told Anne exactly what had happened the night before without even opening my mouth.

'So Abi, I've just heard that Julie and Rachel can't make tonight's shift, and might not be able to be back for quite a while, what do you say, shall we erase Simon from the staff list??'...........

 

The End

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

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Written by Abi Over, March 2000

 

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