A Journey
By Joannebarbarella
I smile at my customer as I place his drink on the table. His gaze is firmly fixed on my breasts almost spilling out of my low-cut top as I bend forwards. and I doubt if he even sees me smile. I always like it when they do that. That's why I always wear one of my maximiser bras when I'm working.
“Will there be anything else, Sir?” I ask breathily. I now know a prospect when I see one. This one’s good for at least a blow-job if not a full fuck.That’s how I make my real money and it all helps me to meet my goals. Besides which I do enjoy it now that I have accepted who and what I am. I'm a sexy sissy who is on her way to becoming as much of a woman as possible.
********************
When I applied for the job I really didn’t know what I was doing or what I was letting myself in for. Looking back, maybe I should have asked myself exactly what the advert meant, but in these days of political correctness it didn’t make any alarm bells ring.
“Waitperson wanted. Uniform and accommodation provided. Enquire within.”
So there I was, sixteen years old, just left school and looking for a job…any job, in these awful economic times. I had six O-Levels but that didn’t seem to impress any prospective employers. They all wanted experienced employees….but how could you get experience if they wouldn’t give you a job?
The premises behind the ad didn’t look very prepossessing from the street, just a small shop front with curtained windows and a sign saying “Crossover Café & Bar”. I opened the door and entered into a much bigger place than I had expected. The immediate entrance was more like a corridor and twenty feet from the door was one of those lectern-like desks where a receptionist sat. Behind that the room opened out into a much larger space with tables and booths, a bar on one side, a stage big enough for a small band and a dance-floor.
The walls were clad in a red velvety material and hung with portraits of famous models and movie-stars, all female and in the sexiest poses. Marilyn was there, and Sophia and Diana (Dors that is) and Brigitte and Jane and Gina and lots of others from that fifties-sixties era. I fell in love with the place straight away. I had always had great admiration for those beautiful ladies who put the “G” in glamour.
I was gawping at all that feminine pulchritude when an authoritative voice interrupted my teenage lust.
“Can I help you, dear?”
I spun around to find a tall, fortyish woman in a tight black dress that showed prominent breasts standing behind me. From the voice I hadn’t been sure whether I was being addressed by a man or a woman….the voice was sort of indeterminate.
“Ah…sorry….I’m inquiring about the job advertised outside.”
She looked me up and down.
“It might not be quite what you expected. How old are you?”
“Eighteen,” I lied.
She walked around me, sizing me up.
“All right. I’ll give it to you straight. What I really want is a cocktail waitress, but the law says I have to offer equal opportunity work, so I will have to employ a male if I can. So unless you’re willing to wear a dress to work there’s no job for you here. You should also know that this is a gay and transvestite bar, so if you worked here you would almost certainly be propositioned by some of the customers and I would expect you to be nice to them and that might mean providing sexual favours.”
I think she expected me to turn tail and run and I almost did. I suppose under normal circumstances I might have, but these weren’t normal circumstances. I had been looking for a job for two months, pounding the pavements and the laptop keyboard and getting more and more desperate. Apart from anything else I wanted…no…needed…to leave home. My relations with my father were dangerously close to breaking point and my mother was driving me up the wall with her constant nagging at me to get a job.
“What kind of dress would I have to wear?” I was that desperate. I had never even thought about dressing as a girl but it couldn’t be that bad, could it? After all, half the population did it.
She laughed out loud, a bellow that sounded more like a man than a woman.
“It wouldn’t only be a dress. You’d have to be a total girl from top to toe. Hair, face, dress, stockings, heels; a cocktail waitress in a French maid’s uniform…..and I’ll have to give you a trial run before giving you the job. Are you up for that?”
“That’s OK. You can give me a trial. If you give me the job, what’s the wage and what’s the accommodation?”
“We will pay you two hundred and fifty pounds a week. That’s for a six-day week, nine hours a day….or night, to be exact. We open at seven p.m. and close at four a.m. or when the last customers leave and you’ll do prep and clean-up every day. All the tips you get are yours. Most of our girls make as much in tips as they do in wages. The accommodation is the flat upstairs; bedroom, bathroom, living and kitchen. You pay the utilities.”
She laughed again, not as raucously this time.
“If you live up there you can’t be late for work.”
“Can I see it, please?”
“Yes. I’ve got the keys here. Come on up.”
I followed her up a flight of stairs at the back of the club and she unlocked a door on a landing at the top. You certainly couldn’t get any closer to the club. We walked inside and it was better than I expected, clean and airy, basic furniture but enough for me. The bedroom had a double bed, side tables and a large wardrobe and a dressing table with lots of drawers and big three-panel full-length mirrors. I didn’t appreciate then just how essential that would be.
There was a dining table with four chairs in the living room and a settee, two arm-chairs and a coffee table, plus a kind of side-board with a TV and record player. The kitchen had a fridge and stove plus assorted gadgets, crockery and utensils, and the bathroom had a shower and bath as well as a loo.
The rooms all looked as if they had all the things that they ought to have. I could live here easily….anything to get out of home….but this would be paradise. Two hundred and fifty a week for those hours was starvation wages but the flat made up for it in my mind….and any wage was better than no wage at all.
“It’ll be your responsibility to keep everything clean and tidy, and I will check up on you.”
“Thank you. If you give me the job I’ll be happy to live here. When do you want to give me your test?”
“Why don’t we do it tomorrow? I’d better warn you that it’ll probably take several hours seeing as where we’re starting from.” She looked me up and down again and shook her head.
“If you’re not suitable, too bad. I won’t pay you for the time spent in trialling you but if you do suit then you can start the day after, or maybe even tomorrow night if you want. After all, you’ll be dressed and ready to go. If you’re still up for it be here at two o’clock tomorrow.”
I said I could do that….without thinking. I was that desperate. Looking back I can’t imagine why I was so blasé about dressing as a girl and working in a gay bar….but it seemed like a good idea at the time.
Just young and foolish I guess….a typical teenager, except that I had never thought much about sex. I suppose I was just a late starter.
And so I duly turned up the next day at two and the owner, who told me to call her Miss Trudy, took me up to the little flat and told me to strip off. That made me feel a bit shy but she told me that I didn’t have anything that she hadn’t seen many times before and did I want the job or not?
So I stripped and stood in front of her with my hands covering my groin while she walked around me inspecting me.
“Hmm, could be worse,” she said, “not much body hair, slim and a bit coltish.”
She handed me a tube of toothpaste-like stuff.
“Slather this on your legs and under your arms. Leave it on for five minutes and then wash it off under the shower. When you shower wash your hair with the shampoo and use the conditioner afterwards. Make sure to use that nice soap so that you smell pretty. There are towels and a dressing gown in the bathroom. Give me a call when you’re finished and don’t take all day. Fifteen minutes, OK?”
She left me to it. I followed her instructions, hanging my shirt and trousers while I waited for the smelly toothpaste-stuff to do its job. The shower was nice and the soap smelled like flowers. I washed my hair with the shampoo and conditioner and ran a comb through it to get rid of any tangles. My hair was actually quite long, partly because I had not had it cut for several months and partly just to annoy my father.
I put on the dressing gown and called down to Miss Trudy. She came up quite quickly and she was carrying a hanger with a dress on it and an array of underwear, stockings and shoes.
She looked at me.
“This might actually work,” she said. “OK, dressing gown off and put these on.”
She handed me a pair of lacy panties, which I gratefully put on, covering my nakedness. Then she gave me a pair of fishnet tights, which she had to show me how to get into, as I had never worn anything like them before. Once you knew how it was easy and I liked the feel of them against my legs, almost like wearing nothing but a whisper.
A bra came next. Of course, I knew what it was but again had no idea how to put it on. She showed me how and then slipped in a pair of false breasts and adjusted them into position. They felt a bit strange but I thought I could get used to them if that was what the job required.
Then she took the dress from the hanger and had me step into it before zipping it up at the back. It seemed to fit me quite well and I liked the feel of the petticoats as they swished around my stockinged legs. This wasn’t too bad, I thought.
She turned her attention to my hair and worked on it with a dryer and a brush.
“I’ll finish that later. First we’ll see what you look like with make-up. Sit down and stay still.”
She began to work on my face with creams and powders and I could only guess what she was doing. She spent a lot of time round my eyes and finally applied lipstick. She gave me a bottle of stuff to remove it with before I went to bed. Then she went back to my hair and combed and brushed and sprayed until she was satisfied.
“Shoes. Ever worn high heels?”
“No,” I said, as she slipped a pair of four-inch black patent pumps onto my feet (I didn’t know the description that first time).
“Well, if you’re going to work for me you’d better get used to them. They’re an essential part of the uniform. Anyway, let’s have a look at you.”
I stood, tottering in those heels, and saw myself in the three-panel mirrors.
High heels, long shapely stockinged legs, short flared black petticoated skirt seguing into a top of the same colour edged with white lace at the neck and sleeves….and my face and hair! Wow! I was a different person and I liked what I saw.
I liked it all. I knew at that moment that I not only wanted the job but I was going to love it. This was a kind of freedom from my dull, miserable existence before. I really needed her approval. Please let her say I could have the job.
“I think you might do. You’re quite pretty and our customers will like you. Do you want to start tonight, seeing as we’ve got you ready?”
I just nodded. I was still breathless, admiring myself. She said I was pretty! I thought so too.
“All right, a few formalities. Do you have National Insurance?”
I shook my head. “I’ve never had a job before.”
“We can fix that. Name?”
“Les Paul.”…………….I know, I know (snigger)
“Les, from now on you are Lesley here….with an EY not an IE, but we’ll keep your proper name for the NI card. I’ll get you a name badge for the customers. Now, you will be paid from 7 p.m. Do you have any money?”
“Just a couple of shillings.”
“I’ll give you fifty pounds against your salary and take it out of your first pay cheque , OK? If you get any tips that’ll help too. Here are the keys to your flat. Don’t lose them.. I will supply two spare sets of uniforms and underwear. You are responsible for organising your own laundry. We’ll show you the ropes tonight and I’ll give you make-up and lessons for one week. After that you’re on your own; you do it yourself. If you haven’t settled down in two weeks we part company.
“A couple of other things you should know. I’ve told you this is a gay and transvestite bar. You are one of the transvestites and so am I. I am not a real girl but this is how I want to be. Many of our patrons want to have some kind of sex with girls like us. You don’t have to accept if you don’t want to but if you decline do it nicely and politely. If you accept you do it on your own time and whatever you make is yours and there is no comeback to the bar.”
“You may want to work here just as a job. That’s your choice and is not a problem to me as long as you stay in character as a girl during working hours. Do you have anything you want to ask me right now?”
I was still so blown away with how I looked that all the other stuff went over my head, so I just shook my head.
Now it was six o’clock so we had a spare hour before opening time and so Miss Trudy started showing me where everything was. We had a barman to pour the drinks so I only had to ferry them to the customers at their tables, take their orders, deliver the bills when needed and transfer them to the cashier (who was Trudy)and take back their change…..simple really.
Trudy gave me a couple of circuits of practice in carrying trays with full glasses, which was a little more difficult than you would have thought, dodging tables and chairs pulled back into your way. I also had to get used to the heels while I was doing this. The dress was no problem. I already felt totally at home in it. It was just clothing after all.
At 6.30 the regular cocktail waitress came in. Her name was Rose and she had been working in the bar for two years. Trudy introduced us and told Rose to look out for me until I got used to everything. Rose seemed friendly and said the extra help would be welcome. However, when Trudy went about organising the general business of the bar Rose took me to one side.
“Don’t you go stealing my regulars, little girl.”
“I’m sorry, I don’t know what you mean. I haven’t even started yet.”
“Let me put you straight then. There are gentlemen who come here and I service them. You don’t go anywhere near them before you check with me, OK?”
“Y-Yeah, sure. I only want a job. I’m not out to sabotage whatever you’ve got going. I just want to earn a living wage.”
“Yeah. Well, you’ll soon find out that you need a little bit extra to make a living wage. Just don’t tread on my toes, OK? Do as I tell you and we’ll get on all right.”
I didn’t want to upset anyone and was more than happy to toe the line for the people who already worked there.
We opened at seven and there were soon a few customers to serve. I was a little surprised that most of the men looked entirely normal, although I wasn’t sure what I expected gay men to look like. There were a few women too, some of them quite beautiful but a couple were obviously men in dresses. Rose told me they were all actually men. This was one of the few places in town where they could feel comfortable and safe.
I was kept busy taking orders and serving drinks. I got a few inappropriate touches but nothing I couldn’t handle and all of a sudden it was 4 a.m. and closing time. I had a few tips which I shared with Rose and the barman and ended up making an extra two pounds for the night, which I thought was great. Talk about naïve.
When I finished the shift I got out of those shoes as fast as I could and stripped down to naked and removed my make-up as I had been shown and fell into my new bed exhausted.
I went home the next day and collected my pitiful case full of clothing, my laptop and bathroom stuff. I had nothing else to take with me. It was a Sunday so Mum and Dad were at the pub. I left a note to tell them that I had finally got a job and I was moving out and that I would let them know where I was but not to worry.
My little flat seemed very welcoming and it took me no time at all to settle in. There were already three dresses and a selection of underclothes in the wardrobe and drawers in the bedroom plus a pair of shoes under the bed. My feet had been killing me by the time we finished the night before but somehow I didn’t care. I liked them. Wearing high heels had seemed right. I felt that this was my future looking at me.
I unpacked what little I had and set about making the flat friendly for me. That didn’t take long. I had just finished when Miss Trudy showed up, knocking at the door.
“Well, Lesley, how was your first night? Do you think you’ll survive? Can you live with being dressed as a girl night after night?”
“Miss Trudy, my first night was fine. I didn’t mind it at all, and quite honestly I didn’t even notice being dressed as a girl except that the shoes were killing me by the end of the shift and some of the customers seemed to like touching my bum.”
She laughed.
“Lesley dear, that goes with the territory and you won’t even notice the heels in a couple of weeks. In time you may even come to love them. But, otherwise, you were comfortable?”
“Yes Miss Trudy. I can do this.”
“All right. We don’t open Sundays so you actually have tonight off, but I’d like to give you a make-up lesson if you don’t mind.”
I didn’t mind, since I had nothing else to do and I wanted to make a success of my new job.
The first two weeks passed very quickly. I became reasonably proficient at doing my own make-up and no longer needed Miss Trudy’s help to appear good enough for my work shifts and performing my duties as a waitress was a breeze. I was quite comfortable wearing my maid’s uniform and everyone seemed to accept me as Lesley even though they must have known that I was a boy. I fitted right in. I loved my little flat and Miss Trudy seemed to be happy with me. I received my first pay cheque and with tips I had an extra twenty-five pounds. I thought I was in heaven.
Both Rose and Miss Trudy gradually opened up to me and became more friendly as time passed. Rose had been dressing and living as a girl for years and didn’t consider herself a boy at all. She happily serviced the customers in whatever way they wanted as long as they paid her. She was saving up for sexual reassignment surgery and reckoned she would have enough money for the operation in another couple of years.
Miss Trudy was a little more complicated. She considered herself to be a gay male, but loved dressing and living as a woman and would not even consider dressing as a man. She regarded men as the opposite sex and was attracted exclusively to them. She flirted outrageously with her male customers and had many serial affairs with those of them that identified as male. She had absolutely no desires against those of her customers that identified as female but treated them as welcome sisters. She seemed to have adopted me as a kind of surrogate daughter and made it her mission to make me as female as possible. She was always giving me little tips on how to behave like a girl should. She said it was to help me do my job as best as I could and I really tried to do what she said.
Some weeks later Miss Trudy came to me and we had a chat about my personal position. By now I was totally comfortable working as a female. She suggested that I might be more comfortable dressing as a girl full-time. It would make it easier for me changing for work and passing during the day when I needed to go out. I really had to give this some consideration but in the end I thought that was a good idea because, in truth, I was finding it a chore switching backwards and forwards between male and female and I was actually beginning to feel more comfortable being a girl. Somehow it seemed more natural. So she took me shopping and we chose a number of outfits for me. She also introduced me to a salon so that I could get my hair done and a bit of facial pampering. After that I had no trouble going out during the days as a girl and doing my grocery shopping or just walking around browsing the clothes shops and enjoying myself. Nobody ever picked me as a boy and I really liked my new clothes and particularly my underwear, so smooth and silky. Having my hair done and wearing make-up soon became second nature. Wearing high heels no longer bothered me. In fact I now felt uncomfortable in flat shoes and really liked the way the heels made my legs look longer and more shapely. I liked feeling elegant and spent more of my increasing tips on pretty dresses and skirts.
After about ten weeks in the job I had almost forgotten what it was like to dress as a boy. I was a girl 24/7 and that was now my new normal. A day came when I threw away the last of my boy things. I knew I would never wear them again because I was now just so comfortable with my new clothes and they somehow seemed to be much more "me". In fact, boy's clothing now revolted me. Miss Trudy definitely approved. She always called me Lesley and encouraged me to become more girly, although in truth I was finding that I didn't need much encouragement. Maybe that was so that I would be better at my job but I felt that she just liked me better as a girl. Rose had become much more friendly and often introduced me to some of the customers who she said would be nice to me. So far I had resisted advances from these men, but one night I think someone spiked my tea (I didn’t drink on duty) and I felt a little woozy and spaced out by the end of the night, so that when this guy wanted me to suck his dick it didn’t seem at all strange and I did it without protest.
I later remembered licking and sucking and swallowing and enjoying the feel of his penis in my mouth, particularly when I swirled my tongue arond its head, just like eating an ice-cream cone. And how nice the shaft felt in my hands with my fingers wrapped around it and knew I could do it again whenever I was asked. The twenty-five pounds I got for doing it also made it all worthwhile. After that I didn’t need any more encouragement to repeat the experience and it became a regular part of my work and life. I figured it couldn’t do me any harm and it made me quite a lot of money. Extra money was always welcome and I found that I really liked shopping for new clothes and especially shoes, all high-heeled naturally. Miss Trudy suggested, about that time, that maybe I should take female hormones to increase my attractiveness to the customers. She told me that many of them liked breasts on their “girls” and that hormones gave us a more feminine figure, which in turn increased our financial value to them. It sounded like a great idea and I agreed readily. After she suggested it I realised that I had come to want to have my own breasts to fill my bras and make me feel more feminine. Besides, I would be able to wear lower neckline dresses and show off my new assets. My uniforms almost demanded that I allowed my breasts to spill over the top and be on presentation to our customers and my skirts were so short that they barely covered my bum.
She took me to see a doctor, who gave me a couple of injections and a course of pills. At first the only difference that I noticed was that I got mood swings from feeling lovely to feeling sad but after a few months that went away and my breasts began to grow and my bum became bigger. A year totally turned my body shape into a girl’s. I would stand in front of my triple-panel mirrors in the morning and admire my new curves and feel my smooth hairless skin. My penis also shrank and wouldn’t stand up but I didn’t care because I really felt like a girl now and I liked it. I had never used it for sex anyway
Sometime during this period one of my customers wanted to fuck me after I had sucked him off. I didn’t think this would be much of a stretch so I lubricated my backside with KY Jelly and let him have his way. It hurt at first but then I began to enjoy the feeling and ended up screaming in ecstasy when he came inside me. The hundred pounds he paid me afterwards didn’t hurt either. The first of many. I suppose that made me a whore but actually I liked it so much I would have done it for free. As far as I was concerned I was a girl now. Except for that one little piece of flesh I looked like a girl, I dressed like a girl, I acted like a girl and I'm sure I thought like a girl. I had found my true self and I was happy being me.
Miss Trudy sort of confessed that she took me on hoping that things would progress along the lines that they have, that she saw a slightly girly boy who could make a target for her clientele with a little bit of nudging and I fulfilled her wildest dreams.
So here I am, a little over two years after I took a job from sheer necessity. I am now a sexy sissy whore. Sucking cock and anal sex are second nature to me now. There is nothing like a big stiff penis in my mouth with its foreskin pulled back to expose the purple mushroom at its end and I delight in using my internal muscles to help massage a man into cumming inside me. Do I care? Yes, I do. I actually love the girl that I have become. The sex is great and the attention that I get turns me on no end. This is much better than being a nerdy boy tramping the streets looking for a job.
I have had my breasts enhanced so now I have a more than respectable pair of 38Cs which I cherish and can look down on my cleavage. That never fails to give me a thrill. I have had some cosmetic changes to my face including collagen injections to my lips which I think make me look really sexy. I’m very pretty. I know because I get told often enough and can confirm by just looking in the mirror. Yes, I admit to being a little vain. There is no way anyone will ever take me for a boy again, not that there was much chance of that before I embarked on this journey. When I have made enough money I will complete the process and have that little package changed to something much more compatible with the girl that I have become..
When I look back it seems that I sort of drifted into becoming a girl. It was accidental, not something premeditated. Taking this job changed my life and I have accepted the changes that it forced on me, with maybe a little help, but I have never regretted it. It was inevitable in a way….predestined.
Thank you for the opportunity Miss Trudy.
Just Call Her Lesley
By Joannebarbarella
I had a feeling when she walked into my little establishment. Of course she wasn’t a she then, or should I say, she wasn’t dressed like one, but sometimes you can look under the skin and see the person inside. The first giveaway was the enthralled enchantment with the photos of the actresses on my walls. A boy would have been drooling, but she was standing there with her jaw on the ground.
So here was this sixteen-year-old boy looking for a job and there was that air of desperation about him that told me he had been looking fruitlessly for some time. Of course he lied and told me he was eighteen but I’m not dumb. As long as that was what went on his employment record I was in the clear.
Now, in my book, it’s important to be honest, so I told him straight away that if he wanted the job he would have to wear a dress and that this was a gay and transvestite bar. If he wasn’t serious he would have turned and run right there and then. Most teenage boys are hopelessly afraid of having their sexual identity questioned, but he stood his ground, which meant to me that he was either gay or transgendered in some way.
I told him that what I really wanted was a cocktail waitress but that I was obliged by equal opportunity regulations to advertise positions on a non-gender basis, so if he wanted the job I would have to give him a trial run in full uniform. My waitresses were French Maids from head to toe, but he was absolutely clueless and I don’t think he had any idea what it meant. However, I hadn’t had any other replies to my adverts so I felt obliged to give him a go. Besides, like I said, I had a feeling about this one.
I showed him the flat that would be his if he got the job and that was the second giveaway. If I offered him the job he was mine. He was almost drooling at the prospect of living there. The young think they’re so smart but they are always an open book.
What’s that saying? “Age and treachery always beat youth and enthusiasm.”
So we organized for him to turn up at two the next afternoon, when I would transform him into a cocktail waitress and perhaps start him/her working that evening. I thought there was a slim chance that he wouldn’t come but I was 90% certain that he would. I doubted that he knew it himself but he was already hooked.
Yes, he came at two for the trial run. He didn’t realize that he was almost chomping at the bit. I had him strip and set him up for depilation (very little), a flowery shower and shampoo and conditioner. He had nice blonde hair down to his shoulders, which already gave him a girly look. I would be able to work wonders with that.
I gave him his instructions and left him to prepare himself, giving him a fifteen minute timeline before summoning me to dress him. I was going to enjoy that.
It’s time you knew a bit about me, besides the fact that I am the owner of
The Crossover Café and Bar
which is the only place in town that caters to the gay and transvestite/ transsexual communities.
My name is Trudy and I have known since I was a child that I was gay, or, as we used to say then “queer”. I can remember looking at men when I was about eleven and thinking how attractive some of them were. At that age I didn’t quite understand it but within a few years I was definitely crushing on some of them.
Naturally my name wasn’t Trudy then but my boy name no longer matters. I have been Trudy since I was about fourteen and I am now forty-two so two thirds of my life has been spent in the persona that I think I was born to be. Although I never had any sexual interest in girls I was always envious of the vast choices that they had in clothing and their ability to enhance their appearance through cosmetics, hairstyles, et al. I decided that I wanted to use their techniques to increase my own attractiveness to men so I became like them in appearance and manner, and while I have never had any desire to change my sex I have also never had any desire to present myself as anything other than a woman.
I ran away from a hostile home when I was fourteen. I had experimented intermittently with dressing as a girl before then but hadn’t had the nerve or the opportunity to go full-time. I admit that I stole a fair bit of my father’s secret stash, which I didn’t think he knew I knew about. He hid it from my mother so that he could go drinking and gambling. A selection of mum’s cosmetics also went with me.
I already had a boyfriend a few years older than me who had his own flat. I had timed my decampment to coincide with a week when he was away on business, so I used the key he had given me to let myself in.
As I had a place to hide in for a while the next thing I did was go shopping. Marks and Spencer’s provided a reasonably anonymous place to shop for female clothes and I was fully kitted out the same day. I washed and styled my hair that night. I had already grown it long enough to carry a feminine do.
That was it. From then on I was Trudy and never wore male clothing again. As a girl I looked several years older. To cut a long story short I used some of my remaining money to rent a small flat and got myself a job as a shop assistant.
I sussed out a couple of the gay bars in the town and began to hang out in them hoping to pick up men. I got lucky. A couple of weeks later a middle-aged man propositioned me. He was a divorcee who had hidden his homosexuality from his wife for years before getting accidentally outed, whereupon she had started divorce proceedings and they had separated.
He seemed like a very nice man and was well-preserved with a trim body, a handsome face and silver hair. Normally I would have been looking for somebody younger but he impressed me with his good manners and charm. I was surprised that he was interested in someone as young as me, but we hit it off immediately and after a few dinner dates and the inevitable conclusions to those evenings he asked me if I would move in with him. I was looking for safety and security so I eventually agreed. At my age I was very vulnerable and prohibited by law from any sexual relationship with an adult. Being caught would probably have resulted in a charge of statutory rape for the adult and a remand home for me, so discretion was the watchword.
He was in fact a lovely man and I became his companion for the next twenty years. I did come to love him because he was so caring and considerate. He was a doctor with a thriving practice and we had many conversations about my sexual preferences and how I wanted to live my life presenting as a woman, but without actually becoming one. This suited him as he was gay but more than happy to present a “straight” persona to the world. Once I turned sixteen we were technically within the law but , of course, the reality was far removed from the theory.
He did persuade me to embark on a regimen of hormones so that I could more convincingly appear as a woman and I happily went along with this while drawing the line on any surgery. I had no problems with having female secondary sexual characteristics like breasts and a bum that enhanced my outward appearance, but I was still a sissy at heart.
He looked after me and I looked after him. I kept his house, cooked and cleaned and satisfied his sexual needs (and mine too) and I was never short of anything. Then one day he just didn’t wake up in the morning. When his Will was read I was surprised to find that, apart from a few bequests to friends and colleagues, he had left everything to me. Although I knew he loved me I had not expected that.
He had also left me a personal letter, first telling me how much he loved me and how I had saved him from despair and loneliness, and then imploring me to use that part of his money that I did not need for my own living expenses and comfort to benefit people like ourselves who lived on the fringe of society.
I wept.
Later I thought long and hard about how I could best fulfil his wishes and came to the conclusion that providing a safe haven for gay people, lesbians, transvestites and transsexuals….somewhere where they could relax and feel safe amongst their own kind, was the best thing I could do. If they made sexual contacts, so be it. Whatever made them happy. There would be no persecution and no judgements as long as nobody got hurt.
So I opened this bar. I set the prices so that it pays its way without making enormous profits. My customers know that I will look out for them and that they won’t get hassled by the authorities. Occasionally I help somebody with financial problems without it becoming a big thing and usually on condition of confidentiality. I confess that I sometimes satisfy my own requirements with a little fling. A girl occasionally feels lonely after all. And then there are those rare times when I can help someone who is a child like I once was.
*********
I went back to this boy who had applied for the job and who by now should have showered and be ready to be transformed. He really was innocent. I gave him a pair of panties to put on and he managed those but he had no idea how to don the fishnets until I did it for him. They were absolutely gorgeous on those long coltish legs but he didn’t know that. I had guessed his dress size and long experience made it right. I told him to suck his stomach in and we got him zipped up. Later I would introduce him to a corset but he was OK for now.
His hair was near to shoulder length and a lovely shade of blonde. He had already brushed most of the tangles out of it and many girls would have been jealous of those tresses. I gave it a preliminary going over with brush and dryer and left it until I had done his make-up. He was a late-starting boy who hadn’t yet had to shave so I had no trouble doing his face. He already had doe-eyes which I enhanced very easily. I knew I would be able to stir his incipient femininity. He would be putty in my hands.
When I had finished with his face I went back to his hair and added body to it by brushing, curling and spraying. He was no longer a boy although he did not realise it yet. As the finishing touch I slid a pair of four-inch heel pumps onto his feet and helped him stand, turning him to see herself in the three panel mirrors.
She was awestruck….gobsmacked….by the beauty who looked back at her. I knew that she was hooked. I hadn’t been completely honest with her. I actually wanted a transvestite/transsexual waitress and she was delivering what I wanted in spades. While she stared transfixed at herself I asked her her name.
“Les,” she answered.
Talk about serendipity. One small leap to Lesley and she was an entirely different person and would be Lesley for ever.
I asked if she had a National Insurance card and she said she didn’t because she had never had a job. Just another small giveaway from a supposed eighteen-year-old. It didn’t matter. I could fix that easily.
I suggested that she start work that night as we had got her ready and she nodded, still in a daze. I had to practically drag her away from the mirrors and down the stairs. Still, she paid attention to what I told her about our operations and demonstrated that she could handle waitressing without problems. She was a natural in those heels.
I introduced her to Rose and the barman and told them to take care of her until she learned the ropes. I expected that Rose would give her a lecture about keeping away from her regulars but that shouldn’t be a real problem. Lesley was still too shell-shocked to even be thinking about men.
That evening, a Saturday, we had quite a good crowd, but Lesley coped very well. I was pleased to see that she treated all our customers with courtesy and respect, including the dozen or so ladies that came in. Most of our regular girls were very passable, if not downright beautiful, but a couple of them were definitely men in dresses and therefore quite vulnerable. She treated them most courteously, which made me very happy. They were some of the ones that I had promised my “husband” I would protect.
I was kept quite busy myself, so when the night ended I wasn’t able to give her any time. I did notice the occasional wince, which I guessed was from the shoes. Heels are lovely to look at but take a bit of getting used to. I saw that she went straight up to her flat and decided to let her sleep. I had no doubt that she was exhausted after her first night.
My own apartment was only a couple of minutes’ walk from the club. I had sold the house after my man died. Even with two of us it had been too big really and I had got a very good price. I waited until “he” had left the next morning, evidently to bring his belongings from home, and went up to the flat. I stowed some extra uniform dresses in the wardrobe and filled the drawers in the dressing table with underwear and an extra pair of breastforms. It was a start on the road to girlhood.
I went back down and busied myself with paperwork in the office until I heard him come back. I let him have half an hour to get his things sorted and then went up and knocked on the flat door.
After basic pleasantries I offered to give him a make-up lesson.
“We don’t open on Sunday, but I thought you might like some practice.”
“I’d like that,” he said eagerly, and I could see my girl poking through.
So we spent a couple of hours putting on and taking off war-paint. She was “she” by the end of the session and I left her to practice on her own.
I helped her for the next week with dressing , make-up and hair and by the end of the week she was definitely getting the hang of it all. By the second week she was coming in to work having got herself completely ready, and she was establishing a rapport with most of our regulars although still keeping herself chaste. She definitely got along well with our ladies and made them feel comfortable. This was a sign to me that she was going to end up being one with them in one way or another.
I had more or less given her a two-week probation period but she was doing so well that those weeks passed and I knew we were on a winner. As time passed I noticed that she seemed to be less and less comfortable when she had to go out in the daytime dressed as a boy. I didn’t want to put too much pressure on her, but I stopped her one day as she was going out.
“Lesley, my dear, can I ask you something? Would you feel more comfortable if you could dress as a girl all the time?”
A slightly startled look crossed her face and then she smiled, as if she had never thought about it. It took only a few seconds for her to make up her mind.
“I think I would like that very much. Do you think I could get away with it?”
I knew damn well she could.
“You’ve been getting away with it six nights a week for over a month now,” I pointed out.
“Yes, but everybody here probably knows that I’m really a boy and they accept that it’s my job.”
“Trust me my dear. We’ll get you fitted out and I guarantee you will be totally accepted. I’ll take you shopping tomorrow and we’ll get you some clothes and then I’ll introduce you to my friendly salon where you can get your hair done, and your skin and nails looked after. You’ll be gorgeous when they’ve finished with you.”
Her face lit up. “Thank you so much Miss Trudy.”
So the next day I lent her a skirt, blouse and a cardigan and took her shopping, nothing too fancy in the clothes line. We wanted her to fit in, not stand out, so it was good old Marks and Spencer and a couple of the teenage outlets. We also got her several pairs of shoes, which she absolutely insisted must be high heeled. Later I took her to my salon, which was naturally gay-friendly and told them to give her the works. While she was being pampered I ferried our purchases back to her flat and did some office work until she returned.
She came in with her hair and face looking like a million dollars and walking at least a foot off the ground. We went upstairs, cut off all the labels on the goods we had bought and she tried everything on, including the shoes. I swear she was floating and it gladdened my heart to see her so happy. It also meant that my somewhat nefarious scheme was working. I never saw her in male clothes again and I soon saw the lift in her confidence level when she went out. I don’t think she was ever “clocked”. I deducted the costs of our excursion from her pay over the next few weeks, or at least that’s what I told her. I actually subsidised a fair bit.
I saw her coming downstairs one day a little over a month later carrying a suitcase. It worried me somewhat but I kept calm.
“What are you doing?” I asked.
“Oh, these are my boy clothes. I’m never going to need them again so I thought I’d give them to the Salvation Army.”
“That’s nice. Very thoughtful, dear.” I kept a poker face, but my heart leapt. She had come to terms with herself as a girl.
A couple of weeks later I did something that may have been considered evil, but I rationalised it that it helped her on her way to full girlhood. There came a night when one of my male customers whispered in my ear that he would very much like to get closer to her but she had been refusing his advances. Could I help?
I knew him to be a gentleman and a considerate man, so I told him to leave it to me. Fairly late in the evening I slipped a small dose of Rohypnol into her tea, just enough to loosen her up. Afterwards I whispered in her ear that this particular gentleman would like her to give him a blowjob, being fairly sure that she would not remember me saying that in her slightly dazed condition.
She was obedient to my suggestion and disappeared up to her flat with him in tow. An hour later he came back down and thanked me, saying that she had performed admirably. I never told her what I had done but it seemed that any reservations that she might have had about having sex with men disappeared from that night on.. I didn’t press the point but soon heard on the grapevine that she had no compunction about having anal sex as well. Of course I made sure she got properly paid and arranged for frequent medical check-ups.
Shortly after this I broached the subject of taking female hormones to her on the basis that our male customers liked girls with breasts and curves and that our female habitués felt much more at home relating to girls like themselves who were often undergoing similar courses of treatment. I pointed out that I myself had taken hormones (and still did). Taking them did not necessarily lead to an operation but really made you feel comfortable in your own skin and enhanced your female characteristics.
She agreed immediately. I’m sure she now knew that she was a girl and that there was no going back. I took her to a friendly doctor, who also frequented our establishment. He examined her and declared that there was no reason why she should not take hormones if she so wished . She assured him that she did so wish, with no prompting from me and he gave her the initial injections and prescriptions for the required pills on the spot, with the usual admonitions to come back and see him on a monthly basis.
My little girl went back to work and performed her regular and irregular duties very well. I nursed her through the initial mood swings caused by the hormones without too much drama and then her body began to show its changes. She developed very well and we together had to make the requisite upgrades to her wardrobe, including her uniforms, which needed adjusting to cater to her new bust and hips. She was very enthusiastic about the changes.
A year passed and SHE asked ME if she could have her breasts enhanced to a 38C. Given her height I could see no reason why not. Boobs that size would suit her very well without looking grotesque. OK, it meant new uniforms, but that was a small investment against her general contribution to the business. She was a real asset, and her bigger assets would only increase her value. She was now my most popular cocktail waitress and hostess. I could see every day just how much she loved her new boobs because she couldn’t keep her own eyes away from them. Rose was quite jealous but she was not prepared to work as hard as Lesley or invest extra money into her own body. She, naturally, was also on hormones and had her eyes firmly fixed on transitioning as soon as she could afford the operation. I knew she would leave me then.
Lesley had also formed a real bond with one of our regular lady customers, who called herself Sophia. Sophia was a real beauty who had a penchant for the dramatic, exotic and elegant dresses. She came in at weekends because her job did not allow her to dress during the week and she always looked like she had just stepped off a movie set. I think Lesley had a crush on her. That did not bother me at all. My only worry was that she might persuade her to leave me before my plans for Lesley were fulfilled.
My fears were unfounded. As much as Lesley liked Sophia she loved her job with me and its associated perks even more. I did not deliberately pry but the grapevine let me know that she used her now totally natural feminine charms and attributes to encourage our male patrons to utilise her for more than waitressing. She was discreet and polite with the customers but knew exactly how to display herself in the most enticing manner. I was aware that she was saving most of her extra income to finance her eventual transition to full female but I also had additional plans for her.
One thing I had to warn her about was that her value here would decrease once her male genitals were gone. Most of the men here wanted “girls” of their own sex and the women customers did not want competition from the “other” sex. She could of course leave and go to a heterosexual establishment but then she would just be one of the crowd.
She was sensible enough to heed my advice. I had long realised that she was determined to become a complete woman (inasmuch as possible). All signs of maleness had long since vanished. She was 100% Lesley. I had one goal left to achieve.
I had tentatively picked her as my potential partner and eventual successor when I first saw her. Yes, I know that was a great leap of faith and a real long shot, but I had had this intuitive feeling the moment I saw her. Call it an epiphany if you like. Anyway, so far I had steered her along the path that I wanted her to follow and now I had a beautiful young girl who I had, in a way, created, but I still thought she had far more potential.
Look, I loved what I was doing and I was completely comfortable with who I was, but anyone with any sense should have a succession plan. My thought was that she should serve a kind of apprenticeship for a couple of years. She already knew the waitressing part of the business and the unofficial seduction that went with it. Learning the other aspects of running the place, ordering, paperwork, etc, then becoming my full partner I reckoned would take another five years. After that the place would be hers and I would fade into the background.
The most important part, though, would be learning how to manage our community of varied gay men, transvestites, transsexuals and occasional lesbians so that they all co-existed in a peaceful environment. I hoped that she would take on this challenge. I had yet to ask her.
Picking the time to raise the subject was sensitive. I finally decided on a Sunday afternoon and invited her out to a late lunch in a casual restaurant close by.
“Lesley, do you like working for me?”
“Oh, Miss Trudy, you know I do.”
“ Would you like to be more than a cocktail waitress? It’s not a job with a terribly long career path.”
“How do you mean?” She looked worried.
I reached over and grasped her hand in order to comfort her.
“I would like you to learn the business and continue to work for me and with me. How does that sound?”
She was silent for a minute or so.
“What would I have to do? I like what I’m doing now. I wouldn’t want to stop doing that.”
“I’m not saying you won’t be able to continue that. I know you enjoy it and you’re quite the little trollop,” I said with a smile. “That’s good for business, but I want you to broaden your horizons and think about the future. I’m on my own and I want to make sure that I train someone up to take my place. I don’t want the establishment to fold when I eventually give it up and I think you’ve got the ability.”
“You haven’t got anything wrong with you, have you? You’re not ill or anything?”
That’s what I liked about her. Her first thought was concern for me. I smiled at her.
“No. There’s nothing wrong with me. It’s just that I’d like to be able to take a break now and then and know that the café is in good hands. Also, sharing the load will give us both more time to look after our clients. Now, do you want to do it?”
She looked relieved.
“I’m so glad there’s nothing wrong with you. You’ve been so good to me, much better than my mum ever was. Why don’t I give it a try and you can teach me how to handle everything? We’ll see how it goes. But you do know that I like a bit of hanky-panky, don’t you?”
I laughed out loud. I have to be careful with my laugh. When I really let go I sound like a man.
“Of course I know. I watch you flaunt your boobs and lick your lips when you’re giving one of the men a message. You just won’t have as much time from now on, but don’t worry. I’ll give you a decent raise and if you delay your transition I’ll finance it. We’ll work it out so that it fits in with work, OK?”
“With an offer like that, Miss Trudy, how can I refuse?”
**********
So now it’s five years later. Lesley is the manageress of the Crossover Café & Bar. She’s a wonder. The customers love her to bits. Maybe she doesn’t get as much action as she did before, but she’s a bit older now and has got over her earlier randiness a little. It’s wonderful what a few years will do. We organised her transition a year ago and so she’s not quite so desirable to some of our male patrons but a few of the girls seem to like her a lot more now. Win some lose some.
I’m going to offer her a full partnership very soon, a couple of years earlier than I had originally planned, but that’s a good thing. Then I plan on going on one of those gay-friendly cruises.
That's me, Miss Trudy