A Shemale Vacation Ch. 02

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.

Having used me to get himself off, to live out his kinky fantasies of screwing a virgin tranny, Frank became quite bashful. He deposited a very generous amount of money on the table beside my bed, more than we had agreed upon, and left me to it, with his spunk still leaking from my newly penetrated arse. I didn't mind this quick exit at all, I wasn't wanting an emotional connection from this guy, or any guy, I just wanted my arse opened up.

As soon as I had got myself cleaned up after Frank, Saskia returned with another client. I had washed the cum from my body and taken off my jacket and mini-skirt so now I was just dressed in the crimson thong and bra, fishnet stockings and shiny PVC boots, with my makeup thick and slutty and a platinum blonde wig. I could tell I looked good like this from the look of the guy as he came into the room.

"Tamsyn, this is Dennis, he's looking for a good time," Saskia said, leaving me with him.

Dennis was much younger than my previous client, maybe in his early twenties, not much older than me, but he looked much more experienced. He seemed confident, like this certainly wasn't his first time in a place and a situation like this one. He was quite strongly built with dark messy hair, a bit of a beard and some piercing. Unlike Frank who had been quite gentle with me in consideration that I was a young girl having her first time, Dennis was pretty forward.

"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.

"Oh yeah, you like it like that don't you baby," he moaned, "You like to be fucked, whore."

"Oh yes," I gasped, "Harder! Faster!"

And he did just as I requested, taking me from behind, slamming his cock into my arse as hard as he could, withdrawing it and then thrusting back in just as hard, hitting me at that sensitive spot right inside me that was sending my body wild. My whole body was rocking with the force of his thrusts. Before very long, I could feel his hard thrusts getting more wild and erratic, his breathing heavier and, in a few moments, his warm seed spurted from his cock to fill me up once more.

"You are one hot, tight arsed tranny," he said, as he got dressed again, "That's one of the best fucks I've had in a long while."

He left another pile of banknotes on the table and then walked out. Before too long another guy came up the stairs and ploughed my newly experienced feminine body with his long hard member. This was repeated through the afternoon until I was absolutely exhausted. That morning I had been a complete virgin, now dolled up in bra, panties, boots and stockings, I was a fucktoy for multiple guys, a cheap hooker who loved to get fucked.

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.

He stripped naked and sat himself astride my chest so his thick, uncut cock was pointed right in my face. I only had to reach out my tongue to flick across his exposed round head, which I did happily, very quickly making it grow significantly harder. By now I had given a few blowjobs and was becoming more and more skilled at it. The attentions of my tongue as they licked and enveloped the pimp's strong hardness certainly suggested I was getting it right.

"Oh good, Tamsyn," he sighed, "I can see why you have been so popular with our clients, why you have made so many tips. You are pretty virgin, but you have natural talents."

Now, he shifted his position so that instead of sitting astride me, feeding me his cock, he turned the other way. He lay down over my body in a 69 position so that as my head was between his thighs swallowing his meat, his own head was down between my legs. As I opened my mouth to take him inside, appreciating the throbbing warmth on my tongue, passing over my lips, I began to feel the warm wetness of a tongue on my own hard member and I knew that the pimp was going down on my dick even as I sucked his.

He had obviously done this before, because his lips and tongue seemed to know exactly what was needed to get me off. Everything he did seemed to touch me in a sensitive way that triggered another wave of pleasure running through me. Maybe it was just all the sex I had had that afternoon, but for whatever reason it didn't take long of this expert attention to bring me to another climax.

I moaned a high pitched sound of ecstasy as my mouth slobbered over the hard meat that filled it. My hips bucked, my body shook and my warm white cum shot out right into this hot, hard pimp's waiting mouth. He didn't stop blowing me even as I came, sucking the cum right out of me and swallowing it down unhesitatingly. It felt pretty great and only made me suck and lick his dick even more eagerly.

Sure enough, as my limp member slid from my pimp's mouth, his own cock began to twitch and spew forth its monster load, filling my throat and leaking from my mouth. I swallowed it down, it tasted really great, a taste that would always remind me of this evening, when my cherry was taken and I became a whore.

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.

Settled on board the train, all of our thoughts as we headed to the border where on what we could do with the rest of the trip, not on what had come before. Josh, the organiser of everything, was searching through his bag when suddenly he came out with another little announcement.

"Er...guys," he said, "I think that when we were robbed, they didn't just take our money. They've got our passports as well."

"But, we're coming up on the border," Olly said, "We need those to get into France."

"What are we going to do at passport control instead?" I found myself asking.

I may have been imagining it, but I distinctly got the feeling that all three eyes were turned expectantly on me.

To be continued...