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.

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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.