tagTranssexuals & CrossdressersA Shemale Vacation Ch. 01

A Shemale Vacation Ch. 01

bybritneyfan©

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.

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