My Life Was Looking Bleak but Having an Eight-Person Orgy Made It Brighter
The Boyslut wasn’t the only one having orgies at Island House.
Byline: Mickey
It’s not every Friday that you’re fucking eight guys in a hot tub—but I needed this.
The last few months had been rife with life challenges: getting laid off from work, moving apartments, boyfriend troubles…I needed a vacation from the minutiae of day-to-day job hunting and relationship drudgery. I needed somewhere warm as New York descended into the bitter grip of winter. I needed to get pounded. Like, really pounded. Like, line up a bunch of hot men and feel their warm, gooey loads slosh around inside me while my head is pinned down and my ass is pulled up pounded.
And that’s when Zach swooped in for the rescue as some sort of anarchic, Jewish, bisexual, erotic enabler. He invited my partner and me to join him for four days of sexual debauchery at Island House. Having read his first piece about Island House, I jumped at the opportunity to attend. A trip like this was exactly what I needed.
We flew in as a storm bore down on the East Coast, the plane shaking, but eventually landing in glorious sunshine. Luckily, we made it in time for happy hour.
Happy hour at Island House was the key to unlocking all of Key West. It was the branching moment: who you met, vibed with, and wanted to fuck dictated the rest of your vacation. Zach, with a boatload of charisma and his towering body, attracted a lot of attention. Me, facing the bar, with my ass in a Speedo pointed strategically towards the pool, also made new friends.
After happy hour on Friday, we went to Saloon 1, a local Key West bar, for the “competitions,” which was really just a chance to show off your assets to horny strangers.
Saloon 1 turned out to be walkable from Island House and was delightfully divey with painted black surfaces and trashy porn pics on the walls. The contest was a hoot; men were pulled or pushed by their friends to partake in various categories. My partner and I won cutest couple, which I’m sure was helped by us kissing passionately on stage with his hands down my pants. I won best ass, which I’m sure was helped by flaunting my taut asscheeks through a jockstrap to the crowd. It felt good to be wanted. It felt good to be celebrated. And it felt good to be drunk and horny in a gay bar on a warm evening.
So horny, in fact, that the second the competitions were over, I went on the prowl. A tall Latino Daddy from Miami pushed me against the bar and kissed me hard, nipping my lips. I responded with vigorous enthusiasm. He had a great ass—always nice to have something to hold onto as you’re getting plowed—and a thick dick, which I could feel hardening through his booty shorts. I caressed it with my fingers, feeling it grow in my hand, and lolled my tongue over his neck and cheek. I motioned for Miami Daddy to take me to the backroom and pound me out. (It’s a motion where you nod in the direction of the darkroom, bite your lip, and wink.)
The backroom was square, spacious, nicely cool, and already full of men making out in various states of undress. In the pockets of my cut-offs, I had emergency poppers and lube. They got used right away as he flipped me around, spread my legs, and pinned me face-first against the wall.
Miami Daddy was hot, quick, and rough, which I love. My hands and cheek were pressed against the cool cinder blocks as he moaned and thrust, giving me his fat cock. It felt good to be used—my award-winning ass doing what it does best. I rocked back, pulling him deeper into me. He moaned in my ear.
I then watched as my partner kissed his partner and that revved me up. I asked Miami Daddy and his partner if they wanted to join us back in the hot tub. They readily agreed.
We sauntered through the light rain back to Island House, taking off our shirts and rubbing the rain over our sweaty and glistening torsos. I laughed. It was that perfect combination of light drunkenness, deep intimacy with strangers, and the warm tropical balm.
Once back at Island House, we stripped down completely and descended on the indoor hot tub. It’s at the center of a tiled room, sunken into the floor, and has doorways that take you to the steam room, sauna, and upstairs playroom. Centrally located and easy to wipe down, it’s the perfect spot to play when you have a group of hard and horny guys.
And by now, I was extremely hard and horny. There were eight of us in the tub, sprawled and sprawling, hands reaching out to bring everyone closer. My partner and I, Miami Daddy and his boyfriend, a short king Zach had fucked the day before, and three Island House denizens who joined us in the overflowing tub.
The bubbles frothed and foamed, splashing expectant bodies with warm, inviting water. I watched as my partner squeezed the short man next to him, pulling his body in close. One of the Island House visitors with a gloriously bushy brown beard put his arm around me and caressed my nipple gently. I turned to him, waiting for him to kiss me. He obliged happily.
Then, it was almost as if a switch had been flipped. It couldn’t have been more than 30 seconds before the eight of us went from relaxing to fucking. I stood up, and the bearded man followed my lead, spun me around, bent me over, and began eating my ass.
The wiry beard felt heavenly as it scratched against my hole. I took a hit of poppers, gasping as the cooling sensation rippled from my forehead down to my feet. I sighed and bent over further, reached back, and pushed his face further into my ass. His tongue teased my insides. I moaned in pleasure, my toes curling in delight.
I spun my head around, so I could watch my partner fucking our new short friend. He had bent the little man over the side of the hot tub—one hand on his hips and the other grabbing his hair.
Miami Daddy crossed the tub and joined the bearded man in worshiping my ass. They took turns licking and biting my cheeks, moaning and groaning in ecstasy as they opened my hole. I instructed them to fuck me. Miami Daddy then spat in his hands, rubbed his cock, and put it inside me.
The floor tiles scratched my knees, but I didn’t stop. The pain synthesized with the pounding into my ass, creating a body-wide sensation that pushed me beyond my usual limits. I dug my hands into the edge of the hot tub, arching my back, taking the dick deeper, further into me. Finally, I felt it: that rush when you’re open and able—when the self-censoring internal monologue goes silent, and you’re just getting fucked.
I felt the man fucking me pull out, smack my ass, and someone else enter. I didn’t know who. I couldn’t see since he had pushed my face down into the tile. It could have been my bearded friend. It could have been my partner. It could have been anyone. I could feel the grout lines pressing into my facial cheeks as this new top pushed his dick further between my ass cheeks. I ordered him to be rougher, whoever he was. He obeyed, my face sliding up and down the tiles as he pounded my hungry, gaping hole.
He stopped, and I flipped over onto my back, pulling my legs up by my head. My bearded friend grinned and went back down on my ass, eating me hungrily before sticking it in. Miami Daddy’s boyfriend saw what was going on, came over, and shoved his dick down my throat. The warm water dripped off my body as it was pushed back and forth. I gagged on the thick cock in my mouth.
Across the Jacuzzi, I could see more sex. The water sloshed around as two other men rubbed their cocks together, hungrily kissing each other open-mouthed. My partner had the short man on his back, pulling his legs apart and thrusting into him. The little man’s cheeks clenched as my boyfriend pounded away. Then my boyfriend saw me looking at him, pulled out, crossed the hot tub, and ran his hands up and down my legs. Taking over for the two men, my boyfriend grabbed his throbbing dick and began teasing my hole.
He leaned down and kissed me before sliding into my ass. It was wet, open, and ready for him.
“Are you going to cum in my ass, babe?” I whispered.
“Shut up,” he said, thrusting harder, and I knew then that he would. Shortly after, his eyes rolled back in his head while he spasmed, and I felt the warm bursts of his load swirling inside my gaped hole. He collapsed onto my chest, and I felt my own spurts of cum shooting into the recess between our stomachs.
I went back to our room and crashed; I’m pretty sure I was asleep before I hit the mattress. I slept much deeper and later than usual and awoke sated and calm. In the morning, my partner was next to me, cuddling me, similarly calmed. For a moment, we were good again. Incredible how, when your life is falling apart in a million ways, a hot tub orgy can help you find your way back to serenity.