Waiting to Pay a Debt

I was at college, almost broke, bored and no friends. My degree course was in probability and chance, and I had some theories that went against accepted knowledge. My big mistake was to put them into practice at a casino.

At first, I only gambled the smallest stakes, my funds were so limited. But I won frequently. My confidence grew and I took more risks. Then I lost of course. My funds for the term were gone, my credit maxed out and my overdraft had hit its limit. But I couldn't resist.

A man approached me while I was watching the roulette wheel, mesmerised by the flashing reds and blacks.

"You're not playing?"

"I've run out of money."

He offered to extend a line of credit to me, saying it was a quite common service for their regular clients. It was reckless, I knew it was a mistake, but I took the offer. I started to win again. John, the man who arranged the credit seemed happy for me. I started to take bigger risks and, naturally, I lost again. John offered more credit. I won, I lost, and I ended up in a spiral of mounting debt.

One evening he told me that my line of credit was maxed out and that we would have to find a way for me to pay off my debts.

He took me to see his boss, a woman in her fifties. She was tough, told me I could work the bar until I had squared my debts. That was fine by me, and I started working three nights a week. I wasn't making much impression on what I owed, so I increased to five and then six nights a week. I was rarely finished until three or four in the morning and started to neglect my course work.

I'd had to wear the standard uniform for the casino, black trousers, and a white shirt. After a few more weeks, the head barman, Terry, pointed out to me that the girls always got better tips.

"It's just one of those things. Why don't you go for a more androgynous look, the punters might take you for a girl and tip better."

It seemed a bit strange, but I needed to earn more. I'd got quite friendly with Penny, one of the waitresses, and she offered to do my hair for me if I turned up a bit early the next evening. Nothing outrageous she said, just a bit more feminine.

She made my hair look amazing by giving it a sort of windswept look. Lots of hairspray kept it in shape. But she also persuaded me to put on some eyeliner, just to emphasise my dark eyes. She said they were beautiful.

Each evening she would do my hair before our shift, pushing the makeup a bit further each night, until I looked more girl than boy, facially anyway.

My tips improved the more feminine I appeared.

One evening Penny suggested I wear a padded bra under my shirt. Some of the girls wore slacks when behind the bar, so it was another step towards androgyny. I was enjoying the game, and even the extra attention I was getting from the customers. I had even flirted with some of the better-looking guys, and a few of the female customers who showed interest. That improved my tips enormously.

A week or so later, Penny suggested I turn up earlier in the afternoon, when the casino was quiet. She said she had an idea that would improve my tips even more. I tried to pretend to myself that not of this was serious, just a game I was playing.

That day my life took a turn that would never be reversed. When I arrived in the changing rooms, Penny told me to strip naked. I was a bit shy, but she made me do it. She tutted, got some cream from her bag, and told me to go and sort out my body hair. I followed the instructions on the label and thirty minutes later I was as smooth as a baby, all over my body.

I hesitated at her next instruction, but she reminded me how much I owed the casino and how tough the boss could be.

Ten minutes later I was in my familiar crisp cotton shirt, with a padded bra under it. But now I was also in a short, black, flared skirt. It left most of my legs on show. I wasn't toying with an androgynous look any longer. I was taking a much bigger leap into the unknown.

Penny got me practising to walk in stilettos and I quite quickly got the hang of it. Even in four-inch heels I still wouldn't be as tall as many of our male customers.

When my shift began, I was so nervous that I didn't really want to come out from behind the bar. Terry told me I looked great and was very supportive. At one point, when there was a lull in customers, he stood close behind me. His hands rested gently on my hips, and he whispered in my ear.

"Pretty much every guy here would fuck you if he had the chance. You don't have to worry about how you look."

In confirmation, I felt him press against me. There was no doubt his words were genuine, and I was flattered, but a bit scared by my own reaction. Without thinking I pushed back against him. His hands took a firmer hold on my hips.

A customer came to the bar at that moment and as Terry served him, I said I was just going to pop to the restroom. Penny followed me.

"You okay baby?"

"Yes, just a bit... well... confused I guess."

She put an arm round me and told me that I' was bound to feel like that in the early stages.

"After all, you've only been here three months."

I hadn't really thought about how long I'd been working there, but Penny was right. My first visit to the casino had been in winter. It was now spring.

"These things take time, it's not an overnight process."

"What do you mean?"

"You must have noticed that you don't need so much padding that bra now?

Now Penny mentioned it, of course I'd noticed, but I hadn't really thought why. The hair on body was no longer growing back and there were also a few other subtle changes to my figure that I had tried to ignore.

"Have I been drugged?"

"That's a strong word. I think it would be more fitting to describe it as a journey."

I saw it all in that one moment. The reason I no longer got erections, and that my balls and penis had even shrunk. Even in the response I had to men flirting with me, the way I reacted to Terry's advances. I wasn't the same person I used to be. I was now more girl than boy. All of this should have scared me, but in fact it pleased me. The mist of confusion cleared a little, and I realised I wanted to be this way.

"You are so cute. You should hear what some of the clients say. And the boss is very pleased with your progress."

"Anyway, enough for the moment. We have jobs to do."

She winked at me and giggled. Took my hand and led me back out to the gaming rooms. I whispered urgently to her.

"Does everyone know?"

"Not everyone, silly."

I took a tray of drinks from Terry and walked over to the main roulette table. Customers were always polite, if not, John would have a word with them. So long as I was okay with whatever was going on, John would keep a discrete distance.

One of regular guests, a tall good-looking man, always in a suit, beckoned me over. He always drank whiskey, neat. I had one on my tray.

"Bring me luck," he said.

Whenever he asked like that, I would linger beside him. Tonight, I felt different. The skirt I was wearing obviously contributed to my sense of self. His name was Gerry and I had seen him when I was a gambler too. He was controlled, lost as we all did, but he never seemed to care. He placed a bet. I watched as the wheel spun.

His hand brushed the back of my thigh and took my breath away. He was sat on a high stool. I was stood by his side. As the ball rattled into its destination, Gerry's hand caressed my leg. A pleasant tingling shiver ran through my body.

I stayed beside him most of that evening. Wanting him to touch me and make me feel pretty. Penny covered a lot of the work I should have been doing. It was in the early hours of the morning that Gerry asked me what I did after work.

"Sleep," I said, giggling.

"Can I take you out one evening you're not working?"

The invitation came as a complete surprise. I wanted to say yes, even though I knew what that would imply.

"You can think about it if you want. I have rather sprung it on you. Give it a couple of days, I'll ask you again."

I wanted to say yes, but there was the question of whether he knew exactly who I was, under the skirt so to speak. I grabbed Penny as soon as I could and told her what Gerry had said. She assured me that he knew exactly what the situation was and that I should say yes before he changed his mind.

"He is gorgeous. If you don't want him, I'll have him."

I took another complimentary drink over to Gerry.

"Back so soon?"

"Is that invitation still open?"

"Of course."

"Friday?"

He asked where he could pick me up and I didn't want to direct him to my shared student house.

"Here? Maybe we could have a drink first?"

At least that way I'd have Penny and John around in case everything got a bit weird.

When I told Penny said was almost more excited than me and promised to help me get ready.

"What do you have to wear?" she asked.

It was then I realised that the only feminine clothes I had were for work. I didn't have anything back at my place.

"We're near enough the same size," she said. "I am going to bring in some outfits for you to try. We've got, what, three days. No problem."

Those three days went faster than any three days in my entire life. Penny brought in dresses, skirts, and shoes, luckily, we even took the same size in shoes.

She chose a black dress and four-inch heeled strappy sandals. For the first time in my life, I felt the wonder of hold-up stockings. My 'equipment' was so tiny that it tucked neatly into silk panties. There was no longer any fear of it getting hard and showing. My breasts, I definitely had breasts by then, were still quite small, a-cup at best. A lightly padded bra gave me a better shape and Penny had experimented with make-up and taught me how to adjust it.

Over those three intervening days she had also given me instructions and lent me a vibrator with lube. It had been a learning experience, a pleasurable one, but also slightly scary that I was prepared to go that far. By Friday night I was as ready as I was ever going to be.

Gerry turned up on time, he didn't keep me waiting, and we sat at the bar and chatted while we had a drink. It was like I had turned full circle and was now a customer of the casino, albeit a very looking customer.

He had greeted me with a kiss on the cheek, one of his hands resting gently on my hip. I was obviously turning into a slut, because I wanted more, I wanted him to kiss me properly.

He asked me what I fancied doing. I almost said, him. In the end we just had a couple of more drinks at the bar, and he asked if I wanted to go back to his place to relax. I couldn't resist.

In the taxi, Gerry leaned in, and I had my first kiss with a man. It was amazing. I loved that he took the lead. All I had to do was respond. I discovered that responding was in my nature.

Hi hand cupped my face as we kissed. He was clean shaven, but there was a coarseness to his skin that felt right, made him in control. My body ached to be against his, but we were in a taxi, not the most private place in the world.

As soon as we were through the front door of his place, Gerry pushed me against the wall and kissed me again. His body pressed against mine and I could feel how much he wanted me. I wanted him too. His thigh slid between my legs and my arms were round his neck. I was grinding myself against his body.

I some ways I wish we had made it to the bedroom, but when his hands cupped my ass and lifted me off the floor, I instinctively wrapped my legs around his body. It was urgent, exciting, slightly painful, and wonderful.

We spent the night in his bed, made love more slowly and more sensuously in the morning. I have given up on y degree. I live permanently with Gerry and still work at the casino a few nights a week.

Gerry says he likes seeing other men come on to me, even touch me. I like it too, but I am a one-guy gal, and Gerry is plenty enough man for me.