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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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“Mmmm, whose sexy panties are those, Mistress Soleli?” I said, as I took my lips from around her cock, “Have you had another hottie in here with my dad?”

“Sort of,” she giggled, “Those pretty panties are your daddy’s! He’s such a dirty sissy, he likes nothing more than to get dolled up in girly lingerie while he sucks cock just like a real slut.”

I couldn’t help myself. I got up from the bed and walked over to pick up the pretty satin lingerie and examine it. Mistress Soleli laughed again.

“Wow, you’ve just gotta be just like your sissy daddy, don’t you baby?” she said, “Well, why don’t you put them on?”

I quickly stripped from my boyish clothes and dumped them in the corner. I lifted the pink satin panties and noticed they were stiff and sticky with a white substance. I sniffed at them.

“Ha,” laughed Mistress Soleli, “Your daddy was a little too eager, the sissy creamed inside his own panties!”

Far from putting me off, I found the smell of my dad’s cum in his sexy panties to be intoxicating, imagining him dolled up and feminine, his cock stretching the panties as he soaked them with his cum, was an incredible turn on. I stepped into the panties and slid them up my legs, the satin feeling soft and sensual on my arse. My cock strained further to give them an entirely unfeminine outline.

“Ooo, you are a kinky one, baby, loving wearing his daddy’s soiled and stained panties!”

With Mistress Soleli’s help, I slipped into the matching pink satin bra and filled the cup with tissue paper to give me some decent size breasts. I clipped the garter belt around my waist and then sat on the bed and rolled the sheer stockings slowly up my legs, fortunately I was mostly hairless so they made my legs look just like sexy girl’s legs, they felt so good against my skin that I almost followed my dad’s example and filled his panties with a cum load of my own. My girly look was completed as Mistress Soleli applied some make-up and whorish bright red lipstick.

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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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He placed his hand on my thighs and pulled my legs open, pushing my shiny skirt up around my waist to show the large bulge my cock had made in my girly red lace thong. I admired the expression of sensitive pleasure on my made up face as I watched myself in the mirror, watched as Frank ran his hands over my bare thighs and up inside my panties. These he pushed aside so my little cock sprang free, it was every bit as hard as his by this point.

While his right hand continued to stroke his shaft as he stood over me, his left began to explore up inside my thighs. He ran his hand over my throbbing cock and balls and beneath them. I felt my unexplored arse about to receive its first touch as Frank’s finger slid up between my pert cheeks. I let out a sigh as his finger went right up inside me. Instinctively, my arse clenched down on it so it fit tightly in me and I had a momentary panic about how I’d be able to fit the whole thickness of his member inside me when even a finger felt so tight. However, my head was swimming with the thought and feel of being penetrated, even by just a finger, and it felt so good as he moved it around inside me, exploring me, opening me up, getting me ready, that I soon relaxed and began to long for more.

Before too long, it was two fingers and then three. I felt my legs spreading wider and my arse opening up to receive him. He was going deeper and deeper until he was buried right up to his knuckles and was stimulating me right inside. Finally, he felt he had loosened me up enough and withdrew his fingers. As soon as they had left me, I felt an urge to be filled again and, fortunately, I wouldn’t have to wait too long.

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For the second time that afternoon, I stuck out my hand and took a warm, semi-hard dick in it. Having enjoyed the first one so much, it now felt there was very little holding me back, even though this was no longer a busty slut sticking the cock in my face, it was a nicely built man. I didn’t feel any urge to stop as I began to stroke his shaft and flick my tongue over his circumcised head.

“Mmm, Tamsyn, that feels good,” Frank sighed, “You are a natural whore.”

His dick was now almost totally hard in my hand as I licked my tongue all over the length of the shaft until it began to glisten with a mix of my saliva and his pre-cum. I loved the sight of my lips working that cock, his hard manly member and my lips painted and girlish, it was all a new experience for me. I decided to take his dick right inside my mouth and opened my lips to slide it in. I managed to take in a good amount and began to bob my head back and forth, going right down on him.

I was really getting into the role of the hot whore, sucking this guy’s cock with reckless abandon, every fibre of my body devoted to his throbbing meat and my mouth around it. It felt heavenly feeling that warm, live flesh sliding in and out of my mouth. My own cock was rock hard and making something of a tent in my tight PVC skirt. I could taste the deliciously salty pre-cum and it reminded me of how I had tasted my friends’ cum on the arse of a shemale whore and how I had loved it. I began to suck and taste ever more eagerly, willing this guy to fill my throat with his hot seed. However, I felt him pull away and was filled with disappointment.

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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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Natassia came over and stood between where I opened my stockinged legs. She pulled them up so my ankles were on her shoulders and my panty clad arse stuck up a little. She languidly and sexily licked one of her long, elegant fingers and, pulling aside my pink satin panties, began to work it around my arse, loosening me up for her monster member. Soon I was riding my arse back against three fingers and loving the feel of being filled up by them.

Now was the time, Natassia withdrew her fingers and pushed the head of her cock, still slick with my saliva against my tight anus. I tried to relax as she slowly pushed her meat inside me but the pain was still quite something, however I let her continue to impale me as it also felt so good to have my little sissy body stuck on the end of her huge cock. She pulled out and then pushed back in deeper. Again, and deeper once more. Before I knew it, her thighs were pressed against mine and her balls slapping my arse. She had buried her whole eight inches inside me and my whole body was on fire with arousal, totally stimulated in joyfully deep places.

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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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“Are you ready for me, Tamsyn?” Frank grinned, “Because I’m about to make you a woman. There’ll be no going back after this.”

“I’m ready, baby,” I sighed in a high pitched moan, “Fuck me. Stick that hot hard dick in my virgin arse!”

And so he did. He ran his hands down my legs, over the fishnets and PVC boots, until he was holding me by my ankles. Then, he pulled my legs up so my spiked heels were resting over his shoulders as he leant over the edge of the bed. My legs were now spread and my arse raised. It felt wonderfully exposed and just waiting to be taken. I let in a sharp intake of breath and then held, waiting for that wonderful moment when my cherry would be taken.

Frank positioned his dick at the entrance to my hole. I could feel the glistening head of it rubbing against my entrance. And then he pushed his hips forwards and he was inside me. Just the head at first, and that was enough to make me feel impaled. I let out a gasp that was a mix of pleasure and pain and he stopped for a moment. Having allowed me to get used to the feel of it, however, he pushed on passed my sphincter, burying himself in my warm tight young body.

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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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