A Shemale Vacation Ch. 02

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.

"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.

"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.

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.

Saskia was only too happy to hear this. She told the guy to bring in no more clients until she let him know otherwise. Then, she grabbed me by the hand and pulled me away from my friends, taking me back upstairs to the room that had first opened my eyes to the joyous potential of sex and sexuality beyond my simple teenage fantasies. My mind was in a complete whirl, I could hardly think straight and was perfectly happy to entrust my tender body to this whore I had just met.

She commanded me to strip and I did, casting my jeans and shirt aside. Then she took me through into an adjoining room, which turned out to be the bathroom. She shoved me into the shower until I washed all the sweat and cum from my body and then commanded me to shave my body hair. I was eighteen and yet I was still just covered with little more than downy fluff. Nevertheless, I set about removing it until my body was soft and silky smooth. Already I felt more like a woman and it felt good.

Saskia had a wardrobe full of hot, slutty, revealing clothes for her work as a hooker and, from these, she drew some things that she thought would fit me. First the panties, a red lace thong that encased my already semi-erect cock, giving me a sexy feel of lace against my new shaved skin. She helped me slip my arms into a matching bra to make my body look much more like a woman's. The bra was padded to give at least the slight illusion of chesty curves.

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 naïve young male virgin, I saw a cheap but sexy hooker who was about to give some young man the time of his life.

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."

"It looks like it will be worth it," said the man, he was middle aged, probably about as old as my dad, but in good shape and quite attractive in an unremarkable way, with short greying hair and glasses, "She is a very pretty girl. I will be happy to make her a woman."

"This is Frank," Saskia said to me, "He has a wife but he likes his girls with something extra so he comes here too. He is a very good lover and will be good for you. I'll leave you two together."

I became even more nervous when Saskia left the room and it was just me and this Frank guy I had only just met. My nerves didn't really improve when he started to strip from his clothes and pile them neatly on the other side of the room. I had never really thought sexually about another man before today but my lust for cock was getting the better of me. I had to admit my gay side was really starting to come out and I was happy to notice that this guy had a pretty good body and, more importantly, a nice long cock. It wasn't quite as long, and certainly not as thick, as Saskia's, but it was still a fair bit larger than mine and a pretty tasty looking piece of meat. Frank saw me looking hungrily at it.

"Well, Tamsyn, you want to be a good girl and suck my cock?" he asked, "You'd like that, wouldn't you?"

"Oh yes," I gasped, getting down on my knees with my legs still covered by fishnets and PVC boots, my own cock beginning to tug against my little lace panties and tight, short skirt.

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.

"OK Tamsyn, you've got me nice and hard and wet," Frank grinned, "Now I want to take that sweet virgin arse of yours."

I lay back on the bed, still dressed in my full skimpy whore's outfit. I noticed now something that I hadn't before, the ceiling above the bed was a mirror so I could look down upon myself as I lay there. Just looking at my hot reflection made me even hornier. The slutty hooker in the mirror inspired lust in me, but the real strength of my arousal came from the thought that the slutty hooker I was looking down on actually was me.

My platinum blonde hair had been a bit dishevelled by my experience going down on my client's cock. Equally my bright, thick lipstick was smudged and my PVC mini-skirt was riding up my thighs to reveal the tops of my fishnet stockings. I could easily have admired those thighs and my sexy, feminine legs dressed in kinky thigh high boots all day if I had the chance. However, my attention was drawn back to the fact that I was not the only person in the room.

Frank was completely naked and had his hard dick in his hand as he stood over me. I knew what he was wanting to do with it and I knew that I wanted it too. I was nervous, of course, very nervous at the thought of my puckered little virgin arse being torn asunder by his throbbing thickness, yet these nerves were totally overcome by my desire to be filled up by that hard masculinity. I hadn't thought of myself as gay before, but there was no use denying how much I wanted to submit to this man's cock, to feel it buried deep inside me.

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.

"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.

I let out my breath in a long slow sigh as Frank slid further and further inside me. He was pushing in slowly, allowing me to adjust myself to the new and incredible feeling of being impaled on that thick rod. Soon enough, I was completely filled up, my tiny, tight little arse was stretched out completely by the thick stick that was taking my cherry. All I could do was lie there, legs spread and in the air, looking up at my reflection, watching my girlish arse being penetrated.

"Mmm, you're tight, Tamsyn," Frank moaned, "It's a while since I've had a pretty virgin like you. How does it feel with my cock deep in your virgin arse?"

"Sooo gooood," I sighed, as he slid that throbbing meat back out of me, "It feels great to have your manhood up inside me. I want to be fucked, fucked like a girl. Fuck me, Frank. Make me a virgin no more."

This time, he pushed up into me a little firmer and more forcefully. Gradually and gently he began to build up more speed and momentum as he buried his meat in my raised arse and slid it back out again. Meanwhile, I too began to get into the rhythm of my first real fucking. My legs in their fishnets and thigh high boots were still over his shoulders, but I could move my hips, around which my tiny skirt was wrapped, in time with his thrusts and so make sure he was driving even deeper into me.

"Oh. Ohhhh. OOOOHH," I moaned as he rocked my body against the bed, "Oh yeah, that's it. That feels good. Fuck me, baby, just like that."

I could feel my whole body alive and quivering with pleasure, my head spinning in ecstasy as I watched my writhing form in the mirror above, my painted red lips open and moaning. I could see my jacket open and my bra showing, my skirt around my waist and my legs in those kinky boots up in the air. My main attention, however, was on the thick, hard member sliding in and out of my puckered little hole. The feel of this hardness opening me up was making my own little cock as stiff as ever and shaking it around with every push he gave into me. I knew from my light-headed feeling that another orgasm could soon be upon me.

I let out another giggling sigh as I felt Frank's hand reach over me and grab my rock hard cock and begin stroking me off. Now, every time he slid his dick into my waiting hole, he stroked his fist along my own shaft, stimulating me both deep inside and out.

"Oh Tamsyn," he groaned, "I can feel how good my fucking is making your pretty virgin body. I can feel your hardness and it really turns me on. I'm gonna make you cum, Tamsyn, just as I cum in your virgin arse. I'm going to cum soon, Tamsyn, so get ready for it."

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.