Shemale Surprise
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A Shemale Vacation free porn video
A Shemale Vacation - Part One
by Richard-to-Rachel
I was eighteen, na?ve 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 na?ve 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...
Yvette
- 29.05.2021
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