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