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After this, she produced a pair of fishnet stockings that I rolled up my smooth shaved legs until they stayed up at my thighs. Over the stockings were the boots. They were really hot, thigh high PVC with four inch heels, they almost covered all of my stockings with just a couple of inches of fishnet sticking out the top. Simply wearing them over my feet and legs made me feel like a sexy hooker and the kind of girl men would want and would pay for. Walking in them was a little trickier but I managed it in the end.

I was supposed to be a slutty whore so the rest of my clothing didn’t really amount to much. A black PVC mini-skirt barely covered my panty wearing arse and certainly didn’t even come low enough to cover the bare flesh of my thighs above my stocking tops. I wore nothing to cover my red lace bra except for a small leather jacket which didn’t do up over my otherwise bare chest and midriff.

Finally, Saskia sat me in front of a mirror to do my makeup. Again, it was unsubtle and provocative, thick deep red lipstick and long false eyelashes. Examining myself in the mirror as she did this, I could distinctly see my masculine self slipping away and a whole new person emerging, a sexy little slut. With the final addition of a platinum blonde wig, my look was complete. There was no doubting that the woman in the mirror was a whore. I no longer saw a na?ve young male virgin, I saw a cheap but sexy hooker who was about to give some young man the time of his life.

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“Bend over, Tamsyn,” he commanded, “I want to fuck your fine young arse.”

I did as he said, turned my back to him and bent at the waist so my arse was sticking up towards him. As I turned my head to look over my shoulder, I saw him drop his pants and pull out his dick, which was already semi hard. As he walked over to me, he began to jerk it off getting it ready to fuck me. It was slightly longer and thicker than my first but not quite like the majestic meat that Saskia had first fed me.

He didn’t bother to strip any of his other clothes, he was obviously horny and just wanted me as quick as possible, with no kind of foreplay. The thought was something of a turn on for me too, especially as the afternoon’s pleasures had already got me in a pretty sexy mood. I was simply longing to have my newly fucked arse filled again and it seemed like he wanted just the same thing.

He stood right behind me and spread my legs so the pointed heels of my thigh high boots were wide apart from each other and my arse seemed more exposed. He pulled my thong aside and positioned the swollen head of his cock at my waiting entrance. Grabbing my hips, he thrust up inside me in one smooth, hard motion that sent ripples of surprise, pain and delight right through my body. I could tell that this wasn’t going to be the gentle experience of my first time, this was raw and hard and that was just how I wanted it right then.

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We sat there staring despondently at the ground. We had searched through all our bags and pockets and had nothing like the money we needed to pay for the hot sex sessions we had each enjoyed with the hot, hung Dutch whore. The guy, the pimp, who had previously been all smiles and friendly encouragement, very quickly changed in demeanour when he discovered we had not the money to pay. He became quite threatening and aggressive and we four became increasingly fearful of what might happen to us.

Just at that moment, Saskia, the statuesque black shemale whore who had given us all a new experience that afternoon, came to our rescue. Or rather, she came to the rescue of the other three guys with her suggestion. My life, by contrast, was about to become a whole lot more complicated.

Hearing the commotion caused by her pimp, Saskia came back down the stairs dressed once more in her short robe. Knowing what I now knew, I could even see the delicious head of her thick black meat just poking out below the hem of the short silk robe. Seeing that tiny glimpse brought back memories of all I had just done, the way I had taken my first cock in my mouth and loved it, loved it so much that I had creamed in my own pants. The thought filled me with a mix of pleasure and shame. I had been so turned on by the experience, even the memory of it was like nothing I had ever felt before, but I was really afraid that my friends would find out about my eager cocksucking. Well, there was nothing I could really do about that fear, it was about to become a reality.

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Satisfied with her handiwork, Saskia left me alone in the bedroom and went back downstairs. I could hear the muffled sounds of her conversation with the others. I could just about make out her saying what sounded like “she’s ready, she’s hot, she’ll make a fortune”. I knew that she was about to bring up my first client and I was flooded with a combined feeling of fear and anticipation. My body was tense but alive with feeling. I was terrified of what was about to happen and yet willing it to go ahead. I loved the feel of these slutty female clothes. I loved the look of my sexy female self. I wanted to play the part of a sexy whore, even though I was a complete virgin and incredibly nervous at the same time.

I heard footsteps on the stairs again and Saskia came back into the room only now she was no longer alone. My heart skipped a beat in fearful anticipation as she brought her companion into the room, the first person to see me as a girl. Fortunately, as far as I could tell, his reaction was pretty positive as he scanned my slender sexy body in my tiny skirt and thigh high boots.

“This is the new girl,” Saskia said to him, “Tamsyn is a virgin,” she explained, attaching a new feminine name to my enticing new look, “So you’ll be the one to take her cherry. That’ll be a big extra cost for you.”

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When we had both finished cumming, I was finally able to clean up and return to my masculine clothes. Edgar, the pimp, let me keep all of the money but for his cut, he said that I had done so well and made him so much money that afternoon that I didn’t need to pay anything for the time me and my friends had spent with Saskia. He also said that there would always be a job here if I ever wanted it and let me go on my way.

I rejoined Josh, Olly and Harry. All of them both embarrassed and grateful about what I had done to let us go on our way. Although Olly made a few jabs about me being queer or a whore, for the most part they all stayed quiet about what had happened and tried to act around me as if nothing had changed between us.

After all that had gone on, I was kind of pleased to be leaving Amsterdam behind the next day. It felt that we could leave behind all that we had done there and move on with our trip and our lives without thinking about what we had done in that tranny brothel. Our next stop was Paris and we were all very much looking forward to spending our time amongst that beautiful city, and the beautiful French girls.

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I felt my body tense up and thus my arse clench even tighter on my horny first client’s eager dick. That seemed to be enough to do for him and I could feel him filling me up with his warm seed, causing a glow of warmth to expand right through my body. As he leaked his sticky juices inside me, he continued to stroke my own hardness, until I couldn’t take it any longer.

I had had orgasms before, when jerking myself off or in my pants like earlier with Saskia, but this one was different. This time, it felt like my whole body was on fire. There was no part of me that wasn’t taken over by pure pleasure and all this spread right from the cock in my arse to my overactive mind. My cock twitched and shot out a thick load of cum to match that which was inside my arse.

And that was that, I was no longer a virgin. I had had full penetrative sex for the first time, although not quite in the way I had ever expected. Unexpected it may have been, but unpleasant it certainly wasn’t. I had never felt more alive than I had that night dressed as a cheap hooker with a dick buried in my arse. I couldn’t wait for the opportunity to do something like that again and, fortunately for me, I wouldn’t have to wait much at all.

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“I always knew there was something queer about you,” Olly laughed.

“Come on guys, let’s take this seriously for a minute,” Josh butted in, “Now, I don’t know what queer shit Tom’s been up to, but if it’s something that can help us out then maybe we should listen.”

“Fair enough,” Harry agreed, turning to me, “What have you done, man?”

“I sucked her cock,” I admitted, blushing, “I just kind of thought that was what I should do. I thought you had too….”

“Fag,” snorted Olly.

“So, Saskia, you think that Tom can make our money back this way?” Josh asked, “By, er, sucking cock, right?”

“I think that he will make a very good whore, yes,” she replied, “The money will come very easy and then we will let you go ok.”

I guess I didn’t have much choice. We turned to talk it over but I could see in the eyes of the other three that they were all pushing for me to do it. Of course they were, it would get them out of this tight spot, provide them with all the money they needed to get away and they wouldn’t have to do anything themselves, just sit and wait while I humiliated myself. I had already given them enough material to mock me mercilessly for the rest of the trip when I admitted I was a cocksucker.

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“I know just how you can get the money you owe,” she said, walking over to us, “This one should be able to make the money up very easily,” she continued, singling me out and caressing my frightened face.

My only consolation at this moment was the jealous undercurrents in my friends’ surprised looks as they watched this busty beauty caress me, choosing me over them. Maybe they wouldn’t be so jealous when they found out why.

“Yes, this one will do very well,” Saskia smirked, “He is a natural cocksucker and would make a very pretty whore.”

My earlier embarrassment was nothing compared to how I felt right now, outed before all my friends. I felt my cheeks hot as I blushed deeply and tried to turn my eyes from the enquiring faces of my shocked friends, but all that I could turn to was that incredible deep dark cleavage of the beautiful Dutch hooker standing over me. There was nowhere I could turn that wouldn’t remind me of my shame.

“Oh God, Tom, you didn’t…” Harry said, breaking the silence.

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I did feel a little used as they continued to use my tight arse and girlish body for their pleasure before dumping their money slightly shame facedly and leaving, but I had to admit that the feeling of being used for people’s pleasure was a bit of a turn-on. Still, I was pleased when the last one left and I had made a pretty impressive wad of cash.

As I cleaned myself up for the last time, I was about to strip out of my red bra, fishnets and tall boots and my blonde wig, the last remnants of my female whore costume, when I heard footsteps on the stairs. The door opened and in came the guy who had brought me and my friends to this place, the one who was responsible for all these crazy new experiences, Saskia’s pimp Edgar. He looked over me and my pile of money with an approving gaze.

“You have done well, Tamsyn,” he said in his strong Dutch accent, “You would make a very good tranny hooker and I would like very much to keep you here. However, I know that your friends are waiting downstairs for you and this is plenty enough money to pay for you to go, even once I have taken my cut as your pimp.” He went over to the table and skimmed off a substantial amount of the money I had made that afternoon, fortunately the pile was big enough that there was still plenty left for me. “I just have one more demand before you can go,” he said, “I make it a point of honour to personally check the quality of my whores, even a temporary one like you. Lie down on the bed.”

I did as he said, knowing that this was what I needed to do to get back on track with my holiday. Once I had done this, I would go back to being Tom, rejoin the others and we could continue as we had always meant to. Besides, after that afternoon of hot fucking, my cock had returned to being rock hard and crying out for relief for the third time that day.

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However, it wasn’t just the lack of choice, the tight spot we were placed in where I was the only way out. That wasn’t the only reason why I found myself drawn towards agreeing to Saskia’s outrageous suggestion. That afternoon I had been a complete sexual virgin, but now I had tasted my first cock and, I had to admit in my darkest thoughts, I wanted more. The feel and taste of it in my hand and on my lips were so good, I could still feel the thrill throbbing through my body. I guess I didn’t consider myself to be gay, certainly I knew that I had been turned on by Saskia’s sexy feminine body, her big breasts and curves, her full, sexy lips. However, it was the cock that drew me the most. There was a part of me that knew, even then, that even if it wasn’t a woman waving the cock at me that I would long for it.

I definitely didn’t want to reveal these feelings to my friends. Their masculinity already felt perhaps a little threatened after the pleasure they had obviously gained from fucking the hot shemale in the arse. They were just looking for someone to put down, to make themselves feel more straight and manly. I wanted to give them as little opportunity for this as possible after my admitting to sucking shemale cock. However, as they pushed me more into it, it became easier and easier to accept until, finally, it didn’t seem at all strange to be turning to Saskia and telling her I was quite happy to become a whore like her to raise the money.

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