God I was fucked up. It was like a million degrees, my head was pounding, and I had a raging hard on that felt like if it was not attended to soon it would pop. I cant remember exactly how much I had to drink, but I now regret it.
"Matt... you got any Advil over there?" I yelled out to my bud.
It hadn't taken much convincing to get him to come down here with me. Four days on the sunny island of Key West, a hotel room with a pool view, and bus loads of hot chicks getting their last fling in before they had to head back to school. Honestly, who could resist an offer like that.
"Matt?" I asked, struggling to flip over on my bed without aggravating my head ache. I stared at his empty bed.
'Apparently Matt was more conservative with his alcohol consumption then I was... he must be out partying still... somewhere,' I thought.
I rolled into a sitting position and held my head in my hands.
'Fuck! Looks like I've gotta get it.' I looked through my fingers at the bulge in my boxers. "I gotta take care of my head first." I said out loud to my aching cock.
I stumbled to my feet and slowly made my way into the kitchen, using the wall as support. I peered into the dark cabinet, blindly reached my hand in and grabbed the first bottle I found. Luckily it was exactly what I was looking for. I downed two pills dry and shuffled back out into the main portion of the room in search of my smokes. I found them resting on top of the TV with my wallet and keys. Reaching into my pocket for matches, I pulled out only an un-opened condom.
"Let's just hope I didn't get lucky, because I don't remember a damn thing" I grumbled
Hoping the fresh air would clear some of the shit out of my head I stepped out onto the balcony and slumped into a chair.
'Man...' I thought 'what a night!'
I vaguely remembered groping a set of tits at the bar earlier. I smiled and pressed my hand against my cheek, it still stung from a slap I received at some point this evening. I Checked my watch. 3:15am. At least the meds were starting to clear up my vision a little... with luck I might get back to sleep before dawn. I lit up my cigarette and closed my eyes. Seconds later I heard a splash. With ripples visable in the shadowy pool and two piles of clothing sitting on the concrete I strained to see what kind of hot couple this was. Skinny dipping at three in the morning. God that seems like something I would do.
I waited for one of the shadowy figures to enter the oval of light cast off by the tiki torches that bordered the pool. My hand slid off my thigh and onto to my cock in anticipation of the hot scene that was about to unfold. I watched as the guy eased into the light and leaned against the tiled coping of the deck.
"No way", I told myself " this cannot be the same shy and soft spoken dude I brought along as a traveling companion that is about to get busy in a pool. As I looked closer, I became certain it was indeed Matt.
'Good for him,' I thought 'He needs to get laid sometime, he is constantly so god damned serious it will be good for him to have a one night stand while he is down here'.
At least one of us would be getting some action, I haven't banged since the end of the summer semester. I gripped my cock tighter as I saw the slender chick he was about to go down on slowly enter the light.
'Turn around damn it' I thought. All I could see was her back and the top third of one fine looking ass. She stepped further into the light and pressed her chest up against Matt, still standing against the railing.
"What the..." I began as she began kissing Matt. "Holy flying fuck... that is a fucking guy he's kissing!"
It suddenly became all too clear to me that what I thought was just a butch looking chick, was more like a feminine looking guy. I blinked my eyes two or three times to make sure it wasn't the alcohol doing its thing. Yup. That is definitely a guy. My suspicions were confirmed once and for all as he turned slightly exposing a flaccid dick before turning back towards Matt and continuing their passionate kiss.
I couldn't figure out which was more bizarre... the fact that my best bud of eleven years was gay and I hadn't the slightest clue; or the fact that I was still jerking off as he was being deep throated by some island native. I seriously must have taken something other then Advil tonight, because after all of this my cock was as hard as ever. I gripped it tightly and moved my hand up and down rapidly along my pulsing shaft.
'This is so fucking weird' I thought.
I spit in my hand to stop some of the friction I was experiencing, and continued to watch the two queers in the pool. Matt was pressed up against the side of the pool, his muscular arms the only things I could see other then the back of the island guy he picked up. Man, I helped get those arms looking like that so he could impress the ladies... he must have had slightly different intentions. I stroked my cock faster and faster as I watched the intensity of the steamy encounter a couple of floors below me pick up pace.
Matt reached around and grabbed this strangers increasingly sexy looking ass. What was I thinking. The strange guy wrapped one arm around the back of Matt's neck, and I watched as the other dropped down below the surface of the water and began caressing his dick. I knew that dick well. When we were kids we used to go swimming naked in the creek behind my house. He got his first hard on when we were swimming in that creek together
'... oh' I thought 'Well this kind of explains the reasoning behind that'.
Still, somewhere deep inside of me I felt envy. I wanted to be that guy. I wanted to stick my tongue deep in Matt's mouth; wanted to taste his breath. I wanted to lay my hands on his muscular butt and give it a good squeeze. I wanted to reach my hand below the water and give his rockin' package a good fondling.
'Man, there is something seriously wrong here' I tried to convince myself as my hand continued jerking off. I am not gay. I don't even think I am bi. I mean seriously, look at the number of chicks popped by my sex craving penis. At school, I get more fucking action then anyone I know. There remains the fact however that I am so god damn turned on by seeing my best friend go at it with a dude that I can barely breath.
Suddenly, Matt throws his head back and lets out a deep groan. The local guy drops underwater clearly with the intention of preventing his bang buddy's jizz from being wasted. My balls start tingling, and I stroke faster. The guy comes up, takes a breath, and goes back down. I inhale deeply and start shooting hot jets of cum all over my boxers. God that feels so fucking good.
"Grunnnnnnnn!" I moan.
As I lean forward and open my eyes back up I realise that I am now royally screwed. I look out into the pool area, and Matt is staring directly into my eyes.
To be continued.