Everything had been brilliant up till this point. I had travelled in style - flying
first class across the Atlantic from Scotland, being collected at the airport by a
limousine and driven to the marina from where I was taken by private boat to the island;
the champagne flowing all the way. But it was only now that the boat was pulling into dock
that the reality of it truly struck home. For there was my next ride, waiting for me on
the jetty, and it was the most magnificent thing I had ever seen!
I had to pinch myself to make sure I wasn’t dreaming. It had felt so surreal since
the moment I found out. But here I was. The place actually existed. What a lucky lad I was
to have won such an amazing prize!
Parked on an otherwise deserted jetty was a classic red ford mustang convertible.
That in itself was pretty impressive, but the car was nothing compared to what was draped
on top of it: dressed in only a pair of cowboy boots was the most incredible looking hunk
of a man. He was at least six feet tall and two hundred pounds in weight, all of it pumped
up muscle – a real horny beefcake and no mistake! And he was waiting for me!
I gawped at his magnificence whilst my cock stiffened in my pants. He was reclining
with his back resting on the car’s windscreen, his muscular arms curled above his head.
Bulging biceps framed his painfully handsome face – strong fleshy features under sandy
blond hair shorn to a military style buzz cut, piercing blue eyes and an inviting smile,
all aimed in my direction. The pose also highlighted his beautiful smooth chest with its
massive meaty pecs and prominent erect nipples which sat above a ripped six pack stomach.
All of this flesh was tanned to a golden brown by the Caribbean sun under which he so
casually lay. His ass, which I’m sure was a sight to behold, was perched upon the
mustang’s bonnet, and his chunky legs with their thunderous big thighs were bent at the
knees and parted really wide, affording me a view of his lovely big cock, which unlike the
man, was standing to attention – a massive erection of throbbing meat that simply HAD to
go up my arse.
“Welcome to Pleasure Island, sir,” said Gary, the cute young Australian deck hand
who had waited on me during the half hour boat trip. I had really taken a liking to the
young lad who carried off his smart uniform of white shirt and knee length shorts to a
treat. He was a bottom like me, so not really my type, which had given me some initial
concern about my prize. But Gary was so friendly, I didn’t over fret, and he was assigned
for a reason – to help me adjust before I arrived - not fuck my hungry ass. Gary assured
me that there were plenty of other men on the island who would be doing lots of that; and
with a bit of luck – this guy on the car would be the first in a long procession of top
class studs who would shag my brains out over the week ahead!
“Bloody hell, Gary; I see what you mean,” I said as I leered at the tantalising
sight in front of us.
“He’s incredible, isn’t he? And he fucks just as good as he looks. God, what a
cock! I can barely control myself when that thing is up my arse. His name is Travis, by
the way, and he’s your chauffeur. Ridiculous, isn’t it! The hotel is only a few hundred
yards away, but most guests like to be collected by car. It’s become something of a
tradition – to be met by a chauffeur and then... Well, there’s no rush to get there – take
as long as you like. Travis will be happy to help you with anything you might need as a
diversion after such a long and tedious journey to get here.”
“Anything?” I asked, still not quite believing that this was happening to me.
“Of course, sir. I told you. Every man who works here is yours to command. Simply
tell him what you want and he will comply as best he can. I hope Travis is to your liking.
We always try to make sure the chauffeur is well matched to each individual guest’s
tastes. First impressions are very important.”
“I’ll say – he looks fantastic. But...”
“I know it can be difficult to take on board. I understand, sir. But there are no
‘buts’, and you mustn’t allow for any to creep in. You have such an amazing opportunity...
so make the most of it. Let your imagination run wild; allow every fantasy you ever had to
become real. Embrace your sexuality and have the confidence to go for it.”
I tore my eyes away from the splendour that was Travis and looked to Gary who stood
beside me on the deck. He really was a remarkably cute lad with his mop of tousled wavy
blond hair. He had a big cheeky grin and a mischievous sparkle to his eyes, and an even
more mischievous sparkle to the end of his tongue which was pierced with a silver stud.
And his friendliness towards me seemed entirely genuine. It was like I had suddenly found
a new best friend.
“I wish I had someone like you to guide me through it all,” I said.
That cheeky grin broke into an incredible smile; Gary looked like a kid on
Christmas morning, seeing his pile of presents under the tree. “I’d hoped you’d say that!”
he gushed. “It can be easily arranged. I usually spend most of my time servicing the guest
tops; but if you want a sort of mate who acts as an adviser; then I’d be happy to take on
the role. I can be available whenever you want.”
“I’d like that,” I replied, relieved at the prospect. “This is unbelievably
exciting; but it’s a little bit daunting... so what would you suggest here?”
Gary let out a laugh and patted my ass, in a friendly rather than sexual way. “I
suggest you get Travis to give you a good fucking over the bonnet of the car – that’s
certainly what I’d have him do. And don’t be intimidated by the big horny beefcake; or by
any of the other tops who are here to serve you... unless of course you want to be
dominated.”
“No, that’s not my thing. Well... not in a weird sort of way... Bloody hell – I
can’t believe that I won.”
“You’re the envy of so many men, including me. God, you’re going to get fucked by
Travis, and by any other stud on the island that takes your fancy.”
Gary’s obvious enthusiasm gave me an idea. I was pretty sure of the answer, but I
still needed to have it confirmed. “What about having you joining in?” I asked. “Would
that be okay? Can I tell him to fuck you as well as me? Can I tell you to bottom for him?
Would you mind if I did? Sorry, so many questions, but I need to get my head around all
this... Of course, if you were to get involved, I’d want him to finish by coming inside
me. No! Maybe not yet; I still need to get my head around the safety aspect as well. All
over me would be better – I like to get sprayed by spunk. But it would be fun to see the
two of you in action before he did it.”
“I think you’re starting to get the idea, sir. You can have anything you like. If
you want a show to watch or take part in, just set the men up and give them a scenario. Be
as detailed or as vague as you like. And this is one which I’ll be very happy to get
involved in, side by side over the bonnet, Travis’s big cock doing us both... very tasty!
Shall we go?”
“I can’t wait!”
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