This is the story of one of my hottest hookups in Key West, and takes place in February 2006. I was 24, stood 6'1", had brown hair, blue eyes, and weighed around 190 pounds with an average build. My dick is 7.5" cut and pretty thick.
I had been in town only a day and was already itching for cock, so I logged into Manhunt.net to prowl around. I started talking to a couple, Doug (38) and Keith (40), that were staying at the Equator Hotel for their anniversary. We exchanged pics, discussed interests, and decided to meet at Mallory Square at sunset to see if we all clicked.
When we met we eyed each other up and down and I liked what I saw. Doug was about 5'10", brown eyes, brown hair, had what would be called a Dad Bod now and a thick 6" cut cock. Keith was 6'0", blue eyes, sandy blond hair, gym teacher build/vibe, and had an 8.5" uncut cock. We quickly agreed that we should go to their hotel. When we got there I learned it was a Male Only/Clothing Optional hotel. We stopped at their room, stripped down to nothing, and went to the courtyard. It was around 7pm and it was quiet so we had the space to ourselves, aside from the stud bartender on duty. There was a hot tub built for 12 people, a full sized pool and a sun deck with chairs for tanning, and the tiki bar being manned by a hot wolf wearing a black muscle shirt, camo pants and black boots. After getting our drinks we decided to start in the hot tub to relax, make conversation, and break the ice. Maybe 10 minutes went by of us groping each other while I got felt up, poked, and prodded, when three other guests joined us. Another couple, John (26, about 5'8"ish, black hair, brown eyes, short trimmed but a fine carpet of black fur over his swimmers build, average 6"+ cut cock) and Paul (late 40s, 6'1", bit of a beer belly, but it worked for him, and a beer can thick, 8" cut cock) from Texas and a built English guy named Alan (35, 6'2", dark complexion, thick rugby build, light dusting of hair on his chest and belly, and a massive uncut cock, at least 9+").
When they joined us, Keith moved so he was sitting with his right leg under my left leg and his hand was stroking from my knee up the inside of my leg, to my balls, dipped under them to probe my hole and then moved back down to the knee in a good rhythm. The other couple split up so John was on my other side (and he immediately slid his leg under mine and started mirroring the hand movements of Keith, but alternating so that I always had a finger pressing into my hole) and Paul coupled up with Doug. Alan sat behind me on the edge of the tub so his legs were on either side of me, and was rubbing my back, shoulders, down my chest and groping my cock, but after a few minutes he abruptly got up and disappeared. As we were talking and stroking (I now had a hard dick in each hand), John pushed himself up so he was sitting lawn chair style parallel with the water, dick pointed straight up, Keith pushed my head until John's cock head brushed my lips, and I slid my mouth down over it until my nose was pressed flat against his pubes. By this time the other two were going at it hardcore (Doug was bent out of the hot tub getting railed by Paul's thick cock from behind) which I had a perfect view of from my cock sucking angle. While I was sucking John, Keith was holding me up to the water level by my ass, going down on me, fingering my hole. Around this time Alan came back with a case of champagne to celebrate Doug and Keith's anniversary. We started with plastic cups for the cheers, but it quickly evolved (or devolved) into someone taking turns standing on the edge of the hot tub pouring champagne from the bottle into the open mouth of a random person, and then eventually just pouring it over someone as 2-3 others were licking it off them.
After a while of this debauchery (and the appearance of more guests joining in) I had to get out to go take a piss, so I went up to the tiki bar and asked the bartender where the bathroom was, he asked if I had to piss, I said yes, and he said he'd show me the way. He walked out from behind the bar, I started following him, then realized he had stripped his camo pants and boots off and only had his black muscle shirt on (mid 30s, around 6', buzzed black hair, dark eyes, sexy 5 o'clock shadow, Mediterranean, with a thick built body). He led me over to the sun deck, sat in a chaise lounge and yanked his shirt off and spreads his arms. I had never pissed on anyone before, having only seen it in porn before. I must have hesitated too long because he just looked at me, winked, and said "what are you waiting for?" Which prompted me to start pissing on him and the whole time he was telling me where to aim, or that I was missing a spot and the whole time his cock (8+", average thickness) is just growing and growing and growing until I finished, and then he proceeds to piss all over himself. When he finished he stood under the open air shower, rinsed, and then had me suck his cock for a bit. When he had to go back to the bar, I walked back over to the hot tub where everyone was taking turns sucking, rimming, and fucking everyone else and I was taking turns sucking on each "bottom's" cock.
As the night went on whenever someone needed to take a piss I was hoisted up out of the hot tub and brought over to the sundeck where guys took turns pissing on me and then rinsed me under the shower (happened at least a few times, each guy, through the course of the night). One of the times I was getting "showered" I felt more than a finger going in my ass, and I started to turn to see the bartender winking at me while telling me to relax and it'd be a lot easier on me. He squeezed the head into my somewhat loosened hole, and then steadily filled my ass inch by inch without rushing, but only slowed down when I felt his nutsac smack against my ass. He stayed rooted for a few moments and was kissing my neck and licking my ear while someone pushed a bottle of poppers up under my nose. After I took two big hits, everything got warm, light-headed, and I felt my hole relax. The moment my hole relaxed he pulled out until only the head was left in and then slammed the length of his cock back into me, deeper than before. That's when he started fucking me hard and deep as he held me in place against the wall under the shower head, every few minutes getting fresh blasts of poppers shoved under my nose. I was in a heady stupor of pleasure, all I was aware of was his cock pumping in and out of me, and the hands that were molesting, groping, and using me. He bred my ass after a while more of fucking, with many of the party goers watching or helping hold me up against the wall. When he slid his deflating cock out of my well used hole, it was quickly replaced by someone else's mouth and tongue to catch the cum as it dribbled out. I was led over to a chair that had been moved closer to the hot tub, and draped over it face down. While I recovered I was given more poppers and became vaguely aware of random tongues and fingers entering my exposed hole. At one point I felt someone's body pressing down on me as their cock slid inside me and started working my hole with short, quick thrusts. They didn't last very long, and when they bred me, they climbed off and left before I saw who it was.
The last time I was getting pissed on a new face (Joe, late 20s early 30s, 6', black hair, dark eyes, deeply tanned all over, patches of fur on his chest and pits with a college frat boy body, and a 6" uncut dick that drooled continually) walked out into the courtyard and stood there stroking his bulge through his speedo while watching three or four guys drench me at once. He quickly stripped, joined in and emptied his piss on me. When Joe finished he took me by the hand and led me into the pool where Alan and Keith were sitting on the edge, making out and groping each other. Joe and I started making out, hands roaming, his stroking my dick and mine fingering his ass deeply, until I felt something pushing against my hand. I looked over Joe's shoulder and saw Keith smile at me as I felt his cock slide into Joe's hole with only a little resistance and deep groans emanated from both of them. I only realized Alan was no longer on the pool side when I felt his strong hands gripping my ass cheeks underwater and his tongue jabbing into my tender hole. When he came up for air, he picked me up by my hips and bent me over the side of the pool, spreading my cheeks wide, stretching and soaking my hole with his tongue and spit. I had no track of time any more, but at some point he lifted me up and hugged me in a bear hug like he was going to crack my back, his leaking cock head poking into my hole. He took his time and would slide me down and flex his hips up a bit and then relax and withdraw, and then repeat only deeper until he was rooted in me to the base of his cock. Once he was sure I was as used to it as I was going to get he started pounding up into me, I was seeing stars and possibly speaking tongues, and loving every thrust, and pulse of his cock and muscles in tandem. At some point I noticed we were moving around the pool as he continued his assault on my ass, saw that Keith had Joe bent over the side of the pool, and was just sliding his cock out of him, followed by a thick trickle of Keith's cum. Alan walked me up to Joe's ass while he was still slowly pumping into me, all the while stroking my cock and scooping up globs of cum from Joe's ass and rubbing it onto my dick. Then Alan walked us forward, while Keith helped line up my cock with Joe's hole, and Alan started fucking me into Joe from behind while he sucked some other guy's cock that had walked up to him. Keith was teasing my nipples and taking turns making out with me and Alan, so it didn't take long before I lost my load in Joe's ass, which caused my ass to spasm and triggered Alan's flood of cum deep inside me. Alan leaned forward, pinning me against Joe, while Alan kept flexing his half hard cock deep inside me. We caught our breaths a bit like that before untangling, and helping each other out of the pool into a group of chairs.
Close to sunrise the group(s) were finally winding down and pairing off or sleeping naked in the chairs and I went back to Doug and Keith's room with Alan, Joe, and a few other guys. In the shower I got bred by Alan again and then by Keith, while the others all took turns flip fucking and napping until breakfast was served in the courtyard.