I Had Glorious Sex, F*cking Three Guys and a Woman During the Underwear Party on Fire Island

I shamelessly ogled all the exposed asses, walking around with a python in my pants.

The paperback for Boyslut: A Memoir and Manifesto is out now. Order it here!

---

Original illustration by Eduardo

---

There are few gay parties more iconic than the Friday evening underwear party at the Ice Palace in Cherry Grove. Gays from the Pines, dressed in sunglasses and kimonos, tanks and jean cut-offs, flowery button-downs and Speedos, take the ferry over—only to strip down to their jock straps. Some don a leather harness; others wear a durable fannypack or over-the-shoulder waistpack. In it, there’s cash, lube, poppers, bags of white powders, their ID, and chapstick. (Nary a condom in sight.) 

I was staying at the Grove Hotel, and from my window, I could see the underwear party directly across from me. Men with the juiciest asses on the deck smoking cigarettes and waiting in the bathroom line to do a bump with their girlies in the handicap stall. 

I drank a White Claw in my room as I sat and watched the gays filter through. I was like an old man in the southwest, sitting in a rocking chair on my porch with a shotgun on my lap. Only I wouldn’t fire at any approachers. All half-naked men would have been welcome, assuming they quickly lay on my bed, face down, ass up. 

After my third White Claw, the Ice Palace was poppin’, and I was tipsy enough to confidently venture off alone. 

Entering the Ice Palace through the back door (foreshadowing), I was overwhelmed by the male beauty. It’s one of those times I love being bisexual. Gay guys are just so much fucking hotter than straight men. And how lucky was I to be surrounded by a couple hundred absolutely stunning queer men? How is this a norm in the culture? 

Quickly, a Daddy pointed and asked if I was the man in that hotel room. After confirming it was me, he said, “I don’t mean to sound creepy. We just saw you, thought you were handsome, and hoped you were coming down.”

We made out briefly. His husband, directly beside us, didn’t seem enthused, so I politely excused myself. 

Inside, I ran into a friend bartending, who was kind enough to pour me gratis vodka on the rocks. I thanked him and gave him a big tip (also foreshadowing).

I wasn’t living for the music. Even with my earplugs in, it was too loud for me. (I’m hypersensitive to sounds and bright lights. Drugs help dull sensory input, but I’ve been trying to cut back.) 

I took a deep breath and grounded myself by staring shamelessly at every single juicy ass. Focusing on their curves and jiggles not only regulated my nervous system but gave me a fat boner. I walked through the dance floor, only to find a fellow giant my height towering over the pocket gays. When our eyes locked, it was game over. We walked straight over to each other, the twunks parting for us like the Red Sea. 

“Hey,” I said, grabbing his ass and pressing our junks together. 

“Hey,” he replied, grabbing my ass. 

“I’m Zach.”

“Kyle.” I slipped my finger into his wet hole, pre-lubed, potentially pre-fucked. I put one hand on his cheek and kissed him. He had shockingly large DSLs for a white dude, and they looked natural. When he slipped his tongue into my mouth, I fingered his hole harder. His ass clenched around my index finger, and I imagined just how good his booty would feel squeezing my cock.

I grabbed his hand and led him to the end of the open floor, the part sanctioned off by step-and-repeats for fucking and sucking.

A bear was kneeling, surrounded by other thick, hairy men. His mouth was open wide as a cock hit the back of his throat. The other men were stroking their penis or squishing it up against his cheeks, hoping he would take more than one at a time. 

In a corner, I saw a hairless twink, a chicken, getting spit-roasted by two jocks, each wearing backward hats and high socks. 

Kyle and I stood in the center of the room. I dropped my black mesh briefs to my knees and placed my throbbing dick between his cheeks. He grabbed my cock with a handful of lube, stroked me once, and slid me in. 

Having sex with a man my height, we can fuck vertically, standing without any support. I grabbed him by his throat as I thrusted into his ass, his cheeks slapping the base of my cock. With my free hand, I felt under his jock and grabbed his semi. I jerked him until he was erect, moaning, and dripping with pre-cum. I tasted his pre-cum, salty and a little sweet. The man had been eating his fruit.

Pulling his cheeks to the size, I watched as my dick disappeared inside of him. Every time I pulled out, a little bit of his skin stretched, acting as a partial sheath over my cock.

“Squeeze that hole,” I whispered into his ear before biting his lobe. He clenched, and my cock flexed deep inside him. 

“Fuck yes,” I said. Sweat now dripping from my brow down my temples. 

Men started to hover around us. Once they swarmed, stroking their cocks beside us, grabbing my ass, and trying to get my hand to stroke them, Kyle and I both agreed we were done.

It’s not that I don’t like being touched by strangers, but it was a little distracting, and I was already overstimulated. Still, I very much wanted to cum. 

I checked my phone to see a text from Gabriel, the tanned, muscle bottom I sat next to on the shuttle from the LIRR to the ferry. We only said a few words on the shuttle.

“Do you mind if I sit here?” I asked, purposefully sitting beside him because I found him the most attractive.

“Go for it,” he replied, putting in headphones. All right, well, I suppose he isn’t into me, I thought.  

Later the day, when I found him on Grindr and asked if he was the man I sat beside on the shuttle, he replied yes. Simultaneously, we both messaged: “I thought you were really attractive but was a little too nervous to say anything.”

I laughed. It’s funny how often introversion and shyness are equated with being cold, disinterested, and bitchy. Usually, I’m pretty decent at distinguishing between the two, but sometimes, I misread. We swapped numbers then and said we’d meet at the underwear party. 

“Just got here!” he texted 15 minutes earlier. I was now on a mission to find Gabriel, a power-bottom jock, all meat and smooth skin. Surely, he’d be able to make me cum.

Outside, next to the bathroom line, I saw him, his blond tips poking out from underneath his visor. His shades were bright yellow, reflecting a cock he was not so subtly checking out. His knee-high blue socks matched his blue jock. His ass was overflowing. That poor jockstrap was relentlessly working overtime, without any healthcare benefits, to keep his booty from busting out. So big and juicy, and his chest, titties. No, tittays. The perfect combination of muscle with a little bit of fat to make him extra meaty. I sauntered over, the tip of my third leg popping out past the elastic band of my undies. 

“Gabriel!” I said, kissing him. 

“Zach!” He responded. I love how, just hours ago, we were complete strangers, too nervous to talk, and now, you’d have thought we’d been best friends for years. 

“You look fucking incredible,” I said, looking him up and down. “I don’t know how much longer I can wait to fuck you.”

“Where are you staying?”

“Literally right there.” I pointed at my room, which still had the curtains open.

He turned to his friends. “Hey, I’ll be back in 30 minutes.” His friends evaluated me, deemed me worthy, and gave Gabriel a nod. 

His hand was down my jock, squeezing my cock as we walked back to the room. My hand was groping his ass. It all felt familiar, not his body, but the vibes. The comfort of a stranger turned friend—the anticipation of our first time together, which is all too often the best. 

While talking on the way back, we learned that we had played in a gay water polo league in 2019. In an international tournament in Toronto, my team played his, so this wasn’t the first time we had met. 

Back in the room, I threw Gabriel down on the bed and spread his legs. I crawled up his body until our faces were mere inches from each other. Then I let my weight fall, crushing his muscular frame, and my tongue, like the blades of a helicopter, swirled rapidly in his mouth.