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sissyrachel
03-19-2009, 05:57 PM
My latest story, A Shemale Vacation...

Chapter One

I was eighteen, naïve and horny. After graduating from school a group of us decided to head to Europe for a last trip before having to enter our real adult lives. It was a chance to get completely drunk and have lots of wild sex. At least, that was the idea in our simple teenage minds. As for me, wild sex was something I wasn’t exactly familiar with. I was still a virgin and I was pretty determined that that was about to change on this trip. Fortunately, for me, the first stop on our journey was Amsterdam, a place where any kind of sexual pleasure was available for whoever had the money to pay for it.
There were four of us together on the trip. Josh was the de facto leader. He was the one that had suggested and organised the trip. He was a bit pushy in terms of making all the decisions for us and wanting things to always go his way but, given the rest of us were quite laid back about what we did provided there was a promise of drink and sex, then we were mostly ok with that. He was about six foot two, thin with short dark hair and thick rimmed glasses.
Olly was the most laddish of the group. He was always the one pushing for people to misbehave and play pranks. He was also the biggest drinker and partier out of all of us and always had an eye out for good looking women who tended to brush him off. However, he had got a fair bit of action just by his confidence and persistence. He wasn’t great looking, being somewhat stocky with slightly ginger hair and a just developing goatee beard.
Harry, however, was always popular with women due to his handsome masculine looks and sculpted body. He was a decent guy but sometimes found the attention from women frustrating, especially as he had a long term girlfriend, Ellie. He was determined to stay with her despite the two of them going off to different universities that September. He had agreed to come on the trip to spend time with us and to get all the drunk partying out of the way so he could lead a more settled life on getting back home.
And then there was me, Tom, the quiet one. I was kind of the geek of the group and was always sort of grateful that these guys wanted to have me around even though it meant I was most often the target of Olly’s pranks. Otherwise, I tended to keep myself to myself, I was kind of insecure and nervous a lot. Although I wasn’t bad looking, I was quite short and not very muscular so I often found myself overlooked in favour of more manly guys like Harry. I was usually quite happy to follow the lead of the others even though I tended to worry rather more about consequences and getting into trouble. I kind of hoped that this trip would bring out more of a care free side to my personality. That and I hoped to get laid, of course.
Well, we had been in Amsterdam for three days and had been having a pretty great time. Naturally, we had gravitated towards the “Coffee Shops” and the relaxing pleasures of smoking what back home would be illicit substances had made us quite lethargic to anything else the city had to offer. Still, the parks and canals of Amsterdam made it a very nice setting for such chilling out. The one thing, however, that none of us were getting was any pussy.
One night we had been out clubbing and had stayed up all night getting so drunk that we staggered around the streets for what seemed like hours looking for our hostel, during which time we were fortunate none of us ended up falling into a canal, especially as Olly repeatedly gestured to shove one of us in. In the end, he came closest to falling, however, when he threw up violently into the water and ended up being chased by an irate Dutchman coming out of his canal boat cursing tourists. The evening had been a riotous success apart from the fact that none of us had made any headway with the local girls.
Of course, in a city like this, there remained one more option if we wanted to be sure of getting laid. The following day, when we had got over our hangovers, Josh suggested that we make a trip down to the city’s notorious red light district. Harry looked uncomfortable at the idea and made some protest but he was drowned out by Olly who was very vocally in favour of paying a visit to some of the world’s most famous whores. They all turned to me to give the deciding vote. I had to confess that the thought of visiting my first hooker filled me with quite a lot of nerves but equally I felt that this was something that it would be best to do and get over with. I had come here to lose my virginity and would feel a lot happier when it was done with, so I agreed and pretty soon, we found ourselves heading across the town with Josh and his trusty map leading the way to the sex district.
Unfortunately for us, four somewhat naïve eighteen year old tourists, Amsterdam’s red light district was a bit much to take in. Everywhere there were bright neon lights. Windows and doorways all advertised all different kinds of shows and experiences. Our eyes lingered over the sight of many girls all dressed in very sexy and revealing lingerie sat provocatively in the windows, inviting us in. Meanwhile, on the street, hustlers and salesmen tried to attract our attention and draw us towards their particular show or brothel. Four young men were obviously a prime target for these guys and many of them approached us and gave us a lengthy sales pitch.
The combined effect of all this actually became something of a sensory overload. We had come here all brash, manly and confident, determined to pay for a hot Dutch hooker and have our way with her, but now we were confused and perhaps a little scared by this world where sex was offered up so obviously. In fact, our confidence was so lost that we were considering backing out all together and just going back to the hostel.
We had just left the main canal of the red light district and were passing some of the smaller surrounding streets, which still had their own women in windows advertising their desirable bodies, when we were approached by another guy. Unlike those earlier, he seemed a bit less in our face, he attempted to win us round with a softer approach, which actually seemed to work.
“I can see that this is probably you guys’ first time here in our red light district, yes?” he said in thickly accented English, “I understand it can be a little, er, overwhelming for the first time. I think maybe you have too much choice to choose from.” We had to agree that he was completely right on this count, we were overwhelmed and bewildered. “Well, how about I make it easy for you. I have the perfect girl for the likes of you. You come with me and we will make things nice and simple.”
We were all still a little unsure and nervous but our determination of earlier had returned. I think each of us were worried that if we did not accept this offer now then maybe we would end up completely chickening out. I couldn’t allow that to happen, not when I had got so close to becoming a man. So, we all found ourselves following this man around the corner to where he led us into a dark little building.
“I have just the girl for you,” he said, again, “Saskia is the one to set you right.”
He told us a price that seemed pretty cheap compared to some that we had been asked for earlier that afternoon. Still, when Saskia emerged from the room above, she did not prove a disappointment. She was a very tall, toned woman with dark black skin. She had beautiful long legs with powerful thighs, barely covered by a very short PVC mini-skirt. Her large round breasts were held in by a leopard print halter top. Her hair was a mass of dark curls. All in all, she had the look of a hot warrior woman. Not only could I tell that all of us were turned on to look at her and to think of fucking her, but we were all also just a little scared. She came down the stairs and walked over to us, looking us up and down as if she was the one that was selecting and paying for us. She stopped at Harry and grinned at him.
“You first,” she said, commandingly, “Come on up.”
“Er…No. No thanks,” Harry said blushingly, “I’ve got a girlfriend you see. Back home, waiting for me. I can’t cheat on her. I’m just here with these other guys.”
“Really?” Saskia replied rubbing her hands over the crotch of his jeans where we could all see he was developing a bit of a boner, “That’s not what I can tell from this. You want to fuck, boy? Your girly will never know. These boys won’t tell her.”
We agreed that we would keep our silence, nobody back home need ever know what we got up to on this trip. That seemed enough to convince Harry who found himself being led up the stairs by the busty black whore almost before he quite knew what was happening. Although Harry was quite the manly man amongst our former school friends, he looked like a little boy alongside this experienced sexy woman.
About half an hour later, Harry came back down the stairs, looking somewhat guilty and shamefaced, no doubt wondering what this meant for his relationship with Ellie. He came back to where we were sitting waiting our turn and told Josh to follow on up while he sat down with us. Olly was full of questions about the whole thing but Harry was being kind of evasive with his answers and, after a while, we just sat in silence until Josh returned to send Olly up.
Finally, after my three friends had each had their turn, then it was my go. They all sat, happily satisfied to have got their end away at last, just what we wanted from this trip, while I, the virgin, climbed the stairs, stairs which I would climb back down a changed man. I had butterflies in my stomach and was quivering a little with nerves at the thought of finally getting to do what I had been dreaming about.
I opened the door to the room at the top of the stairs and there was Saskia waiting for me, her dark body stretched out on the red velvet sheets of a double bed. Even though she had just fucked three of my friends, she still looked pretty inviting with a big white smile on her full lips as I entered the room.
“Ah, so you are the last one then,” she said, “Come on over and we’ll have some fun.”
She had taken off the skimpy mini skirt and top she was wearing earlier and was now just dressed in a kimono type robe with was open at her chest to reveal all of her pert tits and large nipples but tied at the waist to cover her pussy, that pussy that had just been screwed by my best friends and that was about to be my first. My cock quivered with excitement at the thought.
She untied the string holding her robe on and slid it from her shoulders. Now she was completely naked. It was the first time I had seen a naked woman in the flesh and this close up and I felt both nervous and very excited as I ran my eyes over the curves of that bare black flesh, those beautiful mounds of flesh on her chest, that narrow waist and fine round arse. Those powerful thighs and, between them, a strong, protruding piece of hard flesh. Her cock.
I gasped and staggered back with surprise. This black Dutch beauty had eight inches of firm man meat hanging between her legs. Despite the sexy lips and wide hips, despite the round breasts and curvy arse, Saskia wasn’t a woman at all. She was a shemale whore - a man who’d been transformed into having the appearance of a sexy woman whilst retaining that one obvious piece of manhood.
I’d read about girls, or rather guys, like this and I had been disturbed and disgusted by the thought. Still, now I was in the room with a naked one, the situation was a bit different. I couldn’t take my eyes of her naked body, I just found myself staring. More than anything, I found myself staring at that throbbing purple meat that swung back and forth between her thighs. I felt myself fascinated, hypnotised by the sight of it. I could hardly look away as she reached her feminine hands to hold it and begin to stroke the thick shaft as she licked her lips and spoke.
“So, little boy, don’t you want to have your fun with me?” she said in a deep, sensual voice, “Your friends had lots of fun!”
“Really?” I replied in surprise, imagining each of my friends now waiting for me downstairs having discovered Saskia’s big, hard secret and still wanting to appease their teenage lust, “Even Harry?”
“Oh yes,” Saskia moaned, rolling back her eyes as if with a hot memory, “He was especially keen!”
I guess I could kind of understand my friends. They had been so eager and horny when they got up here. Their cocks, like mine (and like hers!), were probably pretty hard already, and then they were confronted by this tall, busty beauty completely naked and provocatively waving that strange, disturbing yet alluring hardness in their direction. How could they resist?
I could feel the pure lust that tended to run through my frail eighteen year old body taking over as I stared at this strong Amazon beauty. I walked over to her and dropped to my knees, almost as if adopting a posture of worship. Close up, that monster between her legs was even more impressive. I had always been slightly embarrassed at my own four inches but I had even more reason to be when confronted with a woman who possessed twice that length.
Up close as Saskia stroked her length, I could see each throbbing vein of her dark meat, I could see the purple head protruding from the end of her foreskin, glistening with pre-cum, just like my own cock, which was straining against my pants without even being touched. I reached out my hand and wrapped it around the base of her shaft. Her cock was so thick that my little hand could barely reach all around it.
It felt warm and alive, like nothing I had ever touched and held. It was soft and sensitive to my touch but at the same time growing so very hard. She held her hand over mine and guided me to run mine along the length of her thick, veiny shaft so I was beginning to jerk her off. Certainly, I never felt my first time with a woman would be anything like this, but then Saskia wasn’t exactly the woman I had expected. Still, I was burning with desire and my lust was only increased by holding her arousal in my trembling hand. As I began to stroke her big black member, I leaned my head in closer. I wanted more than just to touch it, I wanted a taste. I leaned in even further and brushed my lips across her swollen end, kissing the quivering tip and smearing the glistening pre-cum juices onto my mouth.
“Ohhh,” Saskia sighed heavily, “So, you want to be my little cocksucker boy? Very good. You like the taste of black cock?”
“Mmm, yesss,” I sighed, helpless to resist the intoxicating hardness of her cock and the femininity of her hot body.
I slid my tongue from between my lips and began to lick all around her foreskin, playing around the edge of her meat and then flicking my tongue across that sensitive tip. All the while, I was using my hand to stroke the rest of the length of her shaft. It was pretty obvious to me that I was doing a fairly good job of licking my first dick as it had grown to being rock hard as I had begun to lick it.
Now I moved my way down the thick brown lollipop, I began to drool over the warm hardness, letting my tongue linger on the whole length of the shaft. I kissed and licked every part of that huge manly part while my hand moved from her monster cock to cup her round balls.
“Oh baby, you’re a natural cock licker,” Saskia moaned, “You’re making me so much hotter than any of your friends!”
This encouragement really spurred me on. I loved the notion that my friends had been every bit as turned on as me by this Dutch shemale hottie but had been far less able than me, the innocent virgin, to please her throbbing member. By now, the purple head was leaking pre-cum and looking really good enough to eat.
I knew then that I had to have that dick right inside my virgin mouth, I had to let myself submit to that incredible black snake and the gorgeous big breasted whore behind it. I took the dark beast in my hand and opened my mouth wide. In a moment, I had slid the head in beyond my lips. Now that throbbing muscle was right inside the wetness of my mouth and I was beginning to swallow it.
I was pretty inexperienced at anything like this, but I was also eager and full of lust and desire and that made me as keen as possible to take Saskia’s black meat in my mouth. I probably managed to swallow about half of it before my mouth felt completely filled up by erect, quivering cock. I let it slide back through my wet, drooling lips, making the dark flesh slick and wet. I held just the tip between my lips and flicked my tongue right over the top of it, before swallowing once more as much as I could.
“That’s it, cocksucker, swallow my black meat,” Saskia moaned, “Suck me like you’re the whore!”
I began to build up a rhythm, swallowing the thick hardness and then letting it slide back out again. Saskia, by now, was beginning to get really into it even though I was her fourth fuck of the night. She was bucking her hips in time with my swallowing so she pushed her cock further and further towards the back of my throat. Pretty soon it was her who was in control so it was no longer a case of me going down on her giant hardness but more a case of her fucking my little white mouth with her big black dick.
I was in absolute heaven. All that time of dreaming of my first pussy and I’d never realised how great it would be instead to get a thick hard cock. The feel of that warm, quivering muscle running across my lips and tongue, penetrating my throat, made me feel so alive. It was an incredible kind of contact, merging my body with that of my curvy, hung whore. Right then I could not imagine a better feeling than being on my knees with this black cock sliding down my throat.
My hands had been playing with her balls, now I began to run them over the round curve of her thighs, hips and that chocolate brown arse. Cupping her cheeks, I pulled her closer to me, yearning to bury my face right in her crotch. As her beautiful dick fucked my mouth at an ever faster pace, her breathing becoming heavier and more erratic, I slid my fingers along her arse crack, even going so far as to penetrate her with one finger.
Now, I had never fingered a woman’s arse before so I guess I didn’t know what it was supposed to feel like, but this was not quite what I expected. There was a glossy, sticky substance on my fingers. I pulled my fingers away and turned to look at them. They were sticky with translucent white juices. It was cum.
“Hmmm,” laughed Saskia, “Your friends’ cum. They weren’t hungry cocksuckers like you. They weren’t so interested in my big dick. They just wanted to fuck.”
My head span. How had I not just thought of that? Maybe it was because I was a virgin, I didn’t know any better. I had just assumed that the thing for me to do was get down and worship that hard meat, to lick it, stroke it and suck it. It just seemed so natural. I had just kind of assumed my friends had done so too. Maybe I was just too hypnotised by the allure of that thick black manhood attached to the body of a hot woman. Either way, I found myself embarrassingly positioned in a way my friends would never have got.
Whatever happened now, however, I was far too far gone to turn back. I had had my first taste of shemale cock and it was so incredible I could not just stop now. However, I found myself equally fascinated by my sticky fingers. Something I knew was very wrong was forming itself as a strong urge inside me. Momentarily, I let Saskia’s cock slide from my mouth and began to lick my fingers instead, to lick them clean of the cum my best friends had dumped in this hot shemale whore’s arse.
“Ooh, you are the kinky one,” Saskia moaned as if that thought turned her on as much as it did me, “You want to taste your boys’ cum? There’s plenty more back there.”
So, I found myself no longer licking her cock but now burying my tongue in her brown arse. I could see streaks of sticky liquid running through her crack and over her thighs and I began to lick it all up, to insert my tongue right inside her anus and bring out huge amounts of warm and salty sex juice. It was three people’s cum, three people I knew very well, but never thought I’d know like this. It was pretty kinky but then, I was starting to realise, that’s just the kind of thing that turns me on. It wasn’t just that I liked the warm, salty taste, I liked the feeling of that sticky sex goo all over my tongue and of the thought of drinking down my friends’ orgasms.
The cum tasted so good that now I yearned to taste the same from the black love pump I had been sucking on, the one my friends had so foolishly ignored. I wanted to taste it fresh on my lips and I wanted to feel the full force of it as it jetted out of her quivering manhood. I guess that I didn’t have too long to wait.
“Oh, Saskia, your cock is so hot, so sexy, it feels so good on my lips,” I worshipped at her feet as I stroked the shaft once more and licked it like a lollipop, “I want to taste it. I want to taste your cum, shooting out of you and into me.”
“Get ready for it,” she moaned, “I’m gonna cum right into your crosskicking throat. You can drink me down just like you did with your friends’ juices.”
I opened my mouth and took the head back inside, swirling my tongue right around it. Saskia was now moaning faster and heavier. Her hand was grasping her shaft and furiously stroking it in a feverish manner suggesting she was very close to being sent over the edge. Meanwhile, my own cock was harder than it had ever been. I hadn’t touched it all evening and yet it was about to shoot a massive load right inside my pants. All I needed to reach my climax was for Saskia to reach hers right in my mouth.
Sure enough, a loud scream from my hot Dutch whore signalled the start of an incredible orgasm that had been building up through her three earlier fucks with my three friends. I felt a jet of spunk hit the back of my throat and instinctively swallowed, it tasted even better straight from the warm, living source. More cum continued to shoot from her hard member until my mouth was full of the sticky stuff. Only then did she finish and let her limp black cock slide sticky from shiny lips. Even flaccid it was still a very impressive sight to see, so much more so than my own, which had managed to cream inside my own pants with me hardly noticing, so intent was I on swallowing the black shemale’s spunk.
And then it was time for me to rejoin my friends. My first experience with a hooker, hell my first sexual experience with any woman, certainly hadn’t turned out the way I had expected. I had learnt things about myself that I had never really expected and had had more fun than I could ever have hoped for. Yet, for all my best efforts, I remained a virgin, albeit one who was an enthusiastic cocksucker. Nevertheless, the trip was still young and I was confident I’d have time to break that duck at some point.
I tried to make sure no signs of cum were obvious on my mouth and lips or staining my trousers, as I came down the stairs back to my friends. I know that we had all just enjoyed the pleasure of a shemale hooker but still they had fucked her like a woman, I’d rather they didn’t know that I had behaved like a cocksucking sissy.
Josh, Harry and Olly were all looking both shameful and pleased with themselves, an expression I felt reflected on my face when I rejoined them. Whatever differences she might have had from the expected women, Saskia was well worth what we had agreed to pay for her and we were all pretty happy with the afternoon’s fun.
The man who had shown us in then returned and asked for the sum of money that we had already agreed on. Whenever we went out places, any large sum of money was usually kept by Josh. He was a bit of a control freak and the rest of us were happy not to take that responsibility. So, we all turned to Josh when the money was asked for. Suddenly, things did not look so good, Josh was frantically searching all his pockets and bags and coming up empty handed.
“It’s not good guys,” he said, “I think we’ve been robbed. There’s nothing here!”
“You mean, you take advantage of my Saskia and then you can’t afford to pay!” said the man, angrily, “We have ways of making you pay!”

To be continued…

sissyrachel
03-19-2009, 05:58 PM
Chapter Two

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.
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…

rocklob
03-19-2009, 11:50 PM
sissyrachel,
Another incredibly hot story! You are fast becoming my favorite writer. Like the bachelor party stories I almost came in my pants with this one.
Keep up the good work!

sissyrachel
03-20-2009, 01:42 AM
sissyrachel,
Another incredibly hot story! You are fast becoming my favorite writer. Like the bachelor party stories I almost came in my pants with this one.
Keep up the good work!

Thanks a lot! There will definitely be more of the bride story in future but I'm a bit stuck with it.

In the meantime, here's the next chapter of this one.

Chapter Three

At the French border, it was discovered that we had no passports. We were taken from the train and into a room for questioning. All four of us, Josh, Olly, Harry and myself, were terrified. Sure, we’d been in a sticky situation before on this trip, sticky particularly for me rather than the others, when we’d found we had no money in the Amsterdam brothel, but this was worse. This time we were in trouble with the authorities. I thought that we wouldn’t be able to cheat or bribe or persuade our way out this time.
The room we were in was bare except for a table and chairs, there were no windows and the door was locked. We were trapped in here with no escape. Sitting across the table from us were three French border control officials with angry, frowning faces. They were big, tough guys and none of them looked like they were about to be sympathetic to our story.
“So, you try to sneak into our country,” said the man in the middle, the biggest, most broad shouldered of the three and, presumably, the man in charge.
“No, no, we just lost our passports,” Josh said, “We were robbed. They took all our money, cards, passports. Everything.”
“So, then, how did you pay to get here if all your money was taken?” said the man on the left, a guy with a heavy frown and thick dark hair, eyebrows and a beard.
This was exactly the question I didn’t want asked. I didn’t want to admit what I had had to do to get the money for the rest of our trip. That pile of banknotes in Josh’s bag was a permanent reminder that I had prostituted my body, dressed as a slut and got fucked time and again to get us on our way. Sure, I had loved the feel of dressing as a sexy woman and feeling that hard manhood thrusting inside me, but I was embarrassed as well. I didn’t want the world to know, especially not these hard, serious guards.
“We were able to borrow some money,” I said, quickly, not giving the others a chance to answer.
We sat in that room answering questions for about an hour, getting no nearer to any conclusion. Finally, they decided to search us, going through our bags, seeing if we had anything to smuggle into the country. They found nothing until they got to Josh’s extra bag. The one that he had brought from Amsterdam, from the brothel, the one filled with all the money I had made as a whore.
Before opening the bag, Josh began to talk to the guards in French. None of the rest of us understood French but Josh seemed to be doing a decent job. He sounded very persuasive and the guards seemed quite receptive to what he was saying. I imagined that he was probably offering to bribe them with the money that was in the bag he was holding out to them, only he also seemed to be pointing at me. Whatever he was offering, they appeared to agree to it. He turned back to talk to us.
“Guys, I think I’ve got them to come to an agreement here,” he said, “I think I’ve got a way out of this. I told them about the money in this bag and how we got it and offered them a deal.”
“You offered to bribe them?” I said, excited.
“In a way,” he agreed, “Look, I told them what you did to make the money, told them about Tamsyn’s skills and success and they asked for a demonstration. If you let them have a free go then they’ll let us go free.”
“Again?” I said, “Come on guys, is there nothing any of you can do to help this time?”
“No,” Josh replied, “It’s got to be Tamsyn. Saskia and Edgar told me what a good whore you made. You’re the only one that can get us out of this.”
“We’ll be really in your debt if you do this, man,” Harry persuaded, “What other choice do we have?”
“Besides,” smirked Olly with a nasty edge, “Didn’t you like it? We could all hear your screams of delight from downstairs!”
“OK, fine,” I agreed, resigned to the fact that once more I had no choice but to turn whore to help my friends and me out. And Olly was right, I had enjoyed it last time, “But I’m just Tom. I can’t be Tamsyn without clothes.”
“Don’t worry about that,” Josh said, “I thought these might come in handy,” he opened the money bag, it was full of feminine clothing, “Saskia said that you’d probably want some of this at some point so I decided to take it with us.”
To be honest, I felt a little annoyed and betrayed at this going on behind my back, at the sense that my friends thought that this would not be the end of my time as Tamsyn. After all, I had only done it the first time for them. However, I had already admitted that I had enjoyed the experience, and the sight of all those sexy clothes brought a lot of those feelings back. I would be lying if I said I was totally reluctant to agree to dressing and acting like Tamsyn the whore again.
So, it was with mixed feelings that I went through the clothing in the bag to find an outfit that I liked, while Josh turned to the guards interrogating us and told them that I had agreed to their request. I found something that I liked in a little red dress a black satin panties.
I couldn’t leave the room to change so I just had to take the bag into the corner and strip naked, leaving my male clothes in a pile. I felt embarrassed and self conscious showing my thin naked body and small cock before my friends and the three tough guards. Even more embarrassing was watching them watch as I slid the sexy satin panties up my legs and noticing their reaction as they saw the feel of the smooth material made my cock quiver with excitement.
Fortunately, my body tends to be pretty hairless and had remained smooth since I shaved it prior to my first experience as a cross dressed hooker. Still, I decided to make my legs even smoother and sexier with some black sheer stockings. As I rolled them up my legs I was conscious of the leers of the guards and the inquisitive glances of my friends but I was also starting to enjoy the feel of turning back into Tamsyn.
The dress was a halter neck and I decided to do without a bra. I slipped it over my head and attached the strap behind my neck. It clung tightly to my chest and waist but the skirt fluttered lightly and sensually around my thighs. It was very short and just brushed the lacy tops of my stockings. Unlike the brothel, which had been full of mirrors, here I just had to guess how I looked, but the appreciative noises made by the French interrogators made me start to feel pretty good.
Rummaging further in the bag, I found my wig, the same platinum blonde bob as before, and some makeup. Without experience and without a mirror I couldn’t do much with that, but at least made sure to paint my lips a lurid shade of scarlet so they would look especially sexily feminine as they went down on a hard cock.
“You make a very good girl, Tamsyn,” said the lead guard, “Now you will let us fuck you before we let you go.”
As he said this, he was unzipping his trousers, closely followed in this act by his two partners. They were still sitting in their chairs but had moved back so they were facing towards where I was changing in the corner rather than the table. I walked over to the three of them, trying to avoid the amazed gaze of my friends who had never seen anything like this from me. Although they had been aware of what I had done in the Amsterdam brothel, that was different from actually seeing me do the same before their eyes.
The three French guards had now pulled out their cocks, each had their hand wrapped around their meat, jerking it off as their eyes devoured me hungrily. I gave the same sort of lustful looks to the three cocks pointed in my direction. As I would have predicted from three such masculine looking men, their dicks were equally impressive and large, much more so than mine. In particular, the huge guy in the middle had a thick manhood that looked like it could almost match that of Saskia, the busty black tranny whore whose cock had been the first I sucked.
Just as with that beautiful black meat, I was drawn in towards these three throbbing French cocks. I desired them with every fibre of my body and I knew that without any further encouragement or incentive, I would still be getting down on my knees like I was now. I would still be leaning in and licking my lips. I would still be reaching out my hand to feel that alive warm hardness become stiffer and more excited at my dainty touch.
I took the two cocks either side of me in my hands, the hairy bearded guy and the younger blond who seemed a little nervous. Meanwhile, in the middle and right in front of my eyes, the thickest and longest, the dick belonging to the lead guard, dangled enticingly before my mouth, with the guard stroking it and waving it at me as if daring me to taste it. As I stroked my hands rhythmically along the trembling shafts of his two companions, I leant in even further and let my tongue play around the thick, bulging head of his manhood.
“Come on, whore, suck my cock,” he said, his big manly face leaning intimidatingly over me.
I licked right up the length of that huge, veiny shaft, now certainly approaching Saskia’s eight inches as it solidified to its true length, covering it with my saliva, making it slick and wet. All this time I was continuing to stroke his friends’ cocks and now I turned my attention left to lick around the younger guy’s dick for a few seconds causing him to sigh with pleasure. His cock was not as large as his superior but it was pretty impressive, uncut with a huge mushroom head that I slid between my lips and played my tongue over, leaving a smudge of my red lipstick around it.
I switched right and took the hairy guy’s thick dick in my mouth next. I licked along the shaft as I stroked it, opening my lips to let the head play between them. As I did this, the man grabbed the back of my head and pushed his cock right in causing me to gag momentarily. For a few seconds he pounded his cock in and out of my mouth, fucking my face, before I could come up for air.
Putting my hand back to work on that dick, I turned my face back to the big guy. Kissing and licking his cock ended up with further smudges of my lipstick all over the dark, hard muscle. I opened my lips and began to take the shaft into my mouth, feeling it working its way down my throat before I let it slide right back across my pouting, red, cocksucking lips.
“Ohh, that’s a good little whore,” the big guy moaned as I went down on his erect manhood, “Suck me good, my little slut.”
I had gone from virgin to cocksucking slut very quickly the other day and gained as much blowjob experience in one afternoon as some girls do in years. However, I had never yet taken more than one cock at once and, frankly, the experience was something else. With the first guys I had loved being the one to get them off, the focus of their desire and lust, but then there was just the two of us. Now, I was the centre of attention for all three of these hung, manly men, all their cocks were hard for me, pointed right at me, getting rubbed and sucked by me. It was quite incredible.
In a moment, I was reminded of the fact that my audience didn’t just consist of these three men, either. I heard a groan coming from the other side of the room and remembered that my three friends were also here, sitting across the room from us, just watching the show. I wondered what they thought of it, whether they were enjoying seeing their friend in stockings, panties and a tight, short dress, sucking three big cocks. I wondered whether they were curious or disturbed, whether they were aroused or turned off.
“Oh God, they weren’t wrong, Tom really is a bit of a slut,” I heard Olly say, “Look how he gobbles that cock. He loves it.”
“I think we should really call Tamsyn a she, not he,” Harry said, “She looks just like a girl.”
“Especially with that dick in her mouth!” Josh joked.
Aware of this further audience, I tried even harder to make my cocksucking not only pleasurable for the guy whose cock was sliding between my painted lips, but also for those watching. I wanted to give head like a porn star. I would suck on the big guy’s dick for a while, letting it fill my throat right up, as I stroked off his friends. Then, I would switch to another cock and swirl that around my mouth for a while before moving onto the third.
I continued in this way for a while, getting all three men off with my hands and mouth until their cocks were nearly fit to burst. My own arousal was growing as well, the soft feel of my black satin panties doing nothing to quell the hardness of my dick, such a contrast with the feminine fabric that it rubbed against. I didn’t have to worry myself about my panties much longer, however, as I would soon be losing them.
The blond guy turned his head to his superior as I licked the thick manhood of the hairy guy. An exchange of words passed between them in French, before the big guy, the superior, pushed me off his companion’s member. He grinned down at me, kneeling on the floor in my hooker wig, smudged lipstick and revealing red dress.
“I think, now, my friend will want to fuck you, little whore,” he said.
He stood me up and took me over to the interrogation table in the middle of the room and bent me over it so my head was over one end of the table and my arse sticking up from the other. My legs in their sheer stockings were spread wide and two of the guys flipped up my short skirt around my waist. I could feel the younger man standing behind me, rubbing his hardness along my arse crack, rubbing against the satin of my panties, causing my body to throb with anticipation.
The big guy tore my little satin panties right off and exposed my arse to his companions. At this point I realised that, for the first time, I could see my three friends seated on the other three seats against the opposite wall. My head as it was pushed down against the table was just in a position to line up with their crotches as they sat staring in astoundment at me, just waiting for the moment when they saw their friend’s little white arse penetrated by the large dick of a French border control guard.
I couldn’t tell what their emotional reaction to the scene was but I knew that each of the three was staring intently at me, they couldn’t take their eyes off the dress that hung around my waist, my stocking wearing thighs and my bare arse as the young French guard spread my arse cheeks open and slid his huge mushroom head in between them, pushing it up into my arsehole, making me let out a sigh of pleasure at this eagerly awaited penetration.
I thought I could see signs of uncomfortable, embarrassing erections growing in my three friends’ pants, that telltale bulge that all were trying to hide. However, I didn’t have enough time to know for sure before my view was once again blocked by the sight of two large, heavyset men waving their own, more obviously bulging, cocks in my face. Once more, I stuck out my tongue to lick the two erections as the third, that belonging to their blond companion, slid up into my arse.
The guy behind me plunged his cock right up inside me, until he was rubbing against my arse and the tops of my thighs, his legs pressed against mine, our flesh rubbing together through the thin material of my stockings. Meanwhile, I took the other two dicks back in my hands and pulled them together and into me, so their tips, glistening with pre-cum, were touching each other. I wrapped my mouth around both heads and licked my tongue between the two of them, trying to hold both cocks in my moist wet mouth at once, all while the rod behind me completely impaled the lower half of my body.
With a groan and moan at my tightness, the hung guy behind me pulled out a little and slid back in, beginning to ride my arse with long, slow rhythmic thrusts, pushing my body forward as my tongue played over his companion’s cocks. Amidst the gasping and groaning of the guy ploughing my tight little arse, I began to hear my own high pitched girlish moans.
“Oh. Ohhhh. Ohh, ahhh,” I sighed, “Oh yes. Oh, fuck me. Fuck my tight arse!”
I heard a stifled gasp and giggle from my surrounding friends and was reminded once more what a strange and new thing this was for them. They were only just getting used to seeing their friend dressed as a girl and taking a cock in his mouth, they had never heard me beg for it like a slut, never really realised quite how much I loved this kind of thing. I gasped and moaned even as my mouth was filled with first one cock then the other of the hard men in front of me.
The young man behind me began to push up deeper and harder inside me, practically lifting my feet from the ground as he thrust into me. His breathing was hot and heavy. I had taken enough men in my arse by now to tell that this all meant that his climax was near and I willed him on, desiring that incredible feeling as a man’s firm member shot its warm seed deep inside me. That was the moment I felt most like a real woman getting a real good fucking.
He gasped and groaned as he thrust harder and heavier, beginning to talk, saying things that sounded dirty and sexual in French before letting out one loud cry as he thrust so hard my feet almost slipped out from under me. His cock exploded and I felt that warmth inside my arse that told me he was filling me with his warm white spunk. I felt it running through my arse and dribbling down my thighs over my stocking tops.
As the young blond guy let his dick slide from my sticky arse, his stocky, hairy partner came around behind him to take his place. He ran his hand over my just fucked arse and gave me a slap on my arse cheek that shook my body and caused me to give out a little girlish yelp. He ran his fingers up my arse crack and inside me, beginning to fuck me a little with his first two fingers until they were coated in his friend’s warm white sperm. This he scooped from inside me and, leaning over me, shoved it in my face.
“Eat this, whore,” he commanded in a thick French accent.
I licked the two fingers just like they were one of the many cocks I had taken in my mouth. The taste and feeling of the slimy ejaculate that coated them just made me more eager. I had to admit that I loved the taste of cum wherever it came from and so had no problem licking completely clean the fingers that had just come from my own arse.
As he fed me his friend’s cum from his fingers, his other hand was positioning his thick manhood at the sticky entrance to my tight arse. With the fingers clean, he brought them back and landed another slap on my arse even as he pushed his cock inside me. Grabbing my hips and pulling me back towards him, he ensured that his cock slid right up into me as quick as possible and got me completely impaled.
Even as my whole body felt filled up by this French guard’s thick manhood, the whole of my vision as my body pressed against the table was on the even bigger dick belonging to the biggest guy in the room. I loved the feel of that massive hardness stretching out my mouth as my lips glided over the veiny surface of it. I longed to eat it further. As the guy behind me slid his cock back out and, simultaneously, pushed me further forward onto the table, I seized the opportunity to take that monster cock back between my lips.
I was now being penetrated by two huge poles from both ends, feeling helplessly suspended between them like there was one massive pole running through my body, holding me like a spit. My body was just being thrown back from one guy to the other, being used completely for their pleasure and giving me so much pleasure from doing it. I could hardly move my body of my own accord but that didn’t much matter given how much it was being shaken about by the two strong, burly men standing over my slender feminine form, draped in a dishevelled red dress.
The big guy behind me was even less gentle than his partner. He was really going for it, completely tearing my arse open and not caring about the consequences. He was ramming inside me with such a force that it wasn’t just my body that was shaking, it was the table beneath me. I was even worried that the legs were going to collapse. My own legs, in their sheer stockings, were starting to feel quite wobbly with all the thrill of being screwed like this.
He began to slap my arse with his hand as his dick went squelching into where his friend’s cum had already been and was still leaking out of me, so that each thrust up inside me made a squelching and slapping noise, all while his balls slapped against mine and shook my little but very very hard cock around. The only other noise that could be heard were the sighs and slurps coming from my mouth filled with another piece of hard meat.
He grabbed my waist and pulled me back onto his cock as his head was thrown back and let out a loud noise almost like a howl and filled my arse with another warm, sticky load. I could feel his cock twitching inside the tight warmth of my insides and it stimulated me even more. I felt the flow of his ecstasy enter me as his hot cum ran down my thighs to combine with his friend’s in staining my stockings.
Seeming exhausted from the vigorous fucking he had given my girly little arse, the man slid out of me and sat down by his similarly spent friend. I had taken two big, hard men in my arse and loved it. And I’d done it all for my friends, so we could carry on with our trip and go to France. Now, however, I had one more to take, and it was the biggest, thickest, hardest of the lot.
The big guy flipped me over so I was lying on my back on the table with my legs dangling from the edge. Now, I could see him when he entered me unlike the others who had taken me from behind while I swallowed other dicks. Instinctively, I spread my stockinged legs as he positioned himself beneath me and wrapped them around his waist, pulling him into me. He lifted my little cock out of the way and positioned his monster to grind inside me.
I could look down at my body with the red dress covering my chest and falling around my waist. My body looking so small and girlish alongside the truly built masculine form of this manly guard. In particular, with them right next to each other, the relative sizes of our cocks was quite obvious. Even though mine was as hard as it ever got, it was still only just over half the size of his thick hugeness. It would almost have been humiliating if the sight wasn’t such a turn on.
I could feel my wet lips, the taste of his salty pre-cum still on them, dribbling with lust at the sight of my little arse being opened out by that thick hard dick, the biggest I had ever taken back there. He was unmerciful in pushing up further and further inside me until he was all in and I was feeling rather light headed. It was as if my whole body was filled up by his hard rod and totally devoted to giving it pleasure.
“OK, whore,” he said grinning down at me, “Now you are going to know what it is like to be fucked by a real man. And your friends are going to like to see what a good little whore you have been for them.”
Once more, I was reminded of my extra audience and I tipped my head back to see Josh, Harry and Olly still watching me intently. They seemed fascinated by the show that they had seen, the show that I had put on, revealing my true colours that they had only slightly suspected until now. I had showed myself to be a total slut for cock and they had watched me take it and beg for it, watched me swallow it, get it up my tight hole and drink the cum. At no point of this, it seemed, had their attention turned from the scene. I had worried what they would think of me for doing this, but I could see now that, at least while we remained in the moment, they were obviously appreciating the show.
There could no longer be any doubt about whether that was a bulge of arousal that I could see in their pants. Now, all of them had their trousers dropped and each had pulled out his own cock so that I could see quite how hard they had got by watching their childhood friend dolled up as a slut getting fucked by the French border guards. As the various French cocks had been ploughing into my arse, my three friends had their fists around their own members and were beating their meat to the sight. Maybe I shouldn’t have been thinking this way about my close friends, but I couldn’t help but notice that all three had pretty tasty, long, thick members and I couldn’t help but remember the thrill I had got in my first encounter with Saskia when I had licked her black arse and tasted my friends’ cum that they had deposited there.
Of course, I couldn’t spend too long thinking about this as, pretty quickly, my attention was drawn back to the massive Frenchman who has just embedded his cock in my little arse and was now hammering it in and out of me while I just lay there and watched him do it, watched that huge cock rocking my little body, watched my own little cock desperate to explode, and listened to my own sighs and moans.
“Oh God. Oh yeah. Oh yes, give it to me,” I sighed, “Fuck me, fuck me with your big fat cock. Oh yeah. Ohhhh!”
And suddenly, I found my cock blowing its load without ever being touched. The dicks that had been stuck right up inside me had done enough to stimulate me deep inside so that my cock didn’t need any attention to reach a climax. I felt it running through my body as the big tough guard continued to ram his monster into me. I felt my arse clench tighter on the huge dick, I felt my body shake and the warm cum run through my dick and shoot out across my body, covering and staining my pretty red dress.
“Mmmm, looks like the little slut likes being fucked,” said the big French guard as he continued to use my arse with his huge, thick manhood, “You like it so much, whore, that you’ve made a mess of your slut dress. You’re all covered in cum and your about to get some more.”
He was right, I was soaked in man juices. Every time his cock drove into my arse I could feel it squelching against the deposits of the previous guys, which had also managed to run right down my arse and thighs. My own cock had shot its load and my chest was also covered in the sticky white spunk. I had to admit that I loved the feel of being covered in it, the sense that I had brought all those cocks to this point, that they had used me as their sex toy and then covered me with the signs of their pleasure. However, even more I loved to taste it.
As if he sensed these thoughts in me, the big guy pulled out of my well and truly fucked and torn arse and pushed me back onto the chair by the table. I sat facing my friends as he stood over me furiously jerking his throbbing cock off beside my face. In a minute I heard him groan and saw a jet of hot cum shoot out of his dick across my cheek. The second shot I caught in my mouth and swallowed down easily. He continued to stroke his big beast as he shot loads of creamy juices into my mouth and over my face until his cock, like all his friends’, was finally spent and I was left sitting in the interrogation chair, dressed in just a dishevelled, stained dress and stockings, with cum dripping from my arse and face.
I looked over at my friends. All three of them wore the same expression of happiness and embarrassment that I remember seeing on their faces after their time with Saskia back in Amsterdam. I looked down and saw that all three cocks had spewed forth their own loads of white, sticky cum that now stained their hands and trousers. I had to admit to myself that my friends’ cum soaked cocks still looked pretty tasty but I knew that was one line that maybe I shouldn’t cross. Still, I gave them a knowing smirk at how they had enjoyed the show, and gave them one last moment as I scooped the remaining cum that leaked down my chin and licked it from my fingers.
After all that, our three guards decided that their interrogation had reached its logical conclusion. They decided that we had been most helpful with their enquiries and that we probably weren’t trying to sneak illegally into the country or smuggle anything in and that we were free to continue our journey to Paris where the British embassy would issue us new passports. Although it would cost a decent amount of the money I had earned in Amsterdam.
We finally arrived in Paris late that evening. With our cards and passports gone, we probably couldn’t make our booking at the hotel. Fortunately, Josh revealed that back in Amsterdam Saskia had thought of that possibility too. He said that she had given him the name and address of a friend of hers in Paris and that we would be welcome to stay there for our time in the city.
The area of the city certainly seemed a lot nicer than the one we were planning to stay in. Right in the centre in a traditional 19th century Parisian apartment block, the address we were looking for took as right up to the top floor. We rang the doorbell, completely not sure what to expect and it was answered by a beautiful young French woman who smiled welcomingly at us.
“Hi, you must be Saskia’s friends,” she said, using perfect English but with quite a strong French accent, “I’m Celine. Please come in. I hope we will be able to have lots of fun for the next few days.”

To be continued…

sandiego1
03-22-2009, 08:06 PM
wow!