My Glorious Return to Island House Began With a Very Good Boy

"He was a pitbull of a man. Muscle and meat. Beefy and thick. Just how I like ‘em."

Illustration by ri.place

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I’ve never been one to return to a travel destination. Since there’s so much of the world I haven’t seen, repeatedly flying to Paris—even though I loved my time there—feels foolish. And yet, just last month, I found myself on a plane to Key West, returning to Island House for the third time.

A magnetic pull keeps me coming back to Island House, dubbed the “best gay resort in the world.” There’s an energy at Island House that reverberates throughout my body the moment I step into the lobby. It’s difficult to explain, but I’d say it’s the combination of friendliness and sexual energy.

The men are hot, horny, naked, affable, down to play, but also down to just chat nude in the hot tub while their penises float. It’s a choose-your-own-adventure without the pretenses and judgment that, in my experience, often accompany larger gay venues.

Then, of course, the physical space is a beautiful oasis. Tall trees surround the pool so that no prying eyes can see inside. The rooms have been remodeled to feature modern amenities, including dimmable lights, new memory foam beds, and TVs that sync for playing music. Every bathroom has a bidet, and the staff restocks the mouthwash. (I appreciate that they know their audience.) The indoor sauna had been retiled, now black and shiny.

Image courtesy of Island House

And the food. You guys, I know it’s absurd to talk about the food at a gay nude resort—it shouldn’t really be that big of a factor, but it’s delicious. Tuna tartare, shrimp quesadillas, and chicken and waffles. I’m embarrassed to say how much I loved the food there. Sometimes, while I was getting blown, all I could think was: God, I’d kill for a slice of Island House’s key lime pie.

And the staff is the friendliest group of (attractive) men you’ll meet on the island. They knew how to handle my drunk ass, as, yes, I took full advantage of the daily open bar that happens during happy hour.

Within minutes of stepping foot at Island House, I was in vacation mode, the fastest I had ever switched gears. (It usually takes me a couple of days to go from “New York, walk fast, don’t make eye contact, work mode” to vacation mode.)

After getting settled in my room, I began to walk around the resort in the buff, my dick swinging side to side as I said “Hello” to everyone who stepped within a five-foot radius of me. “Hi!” every man replied with a big smile.

I was ready for a shvitz. (Here's a fun fact about me: I’m always ready for a shvitz. If you live in NY and have a jacuzzi, hit me up. I will let you do filthy things to my body for unlimited access.)

Image courtesy of Island House

The Wednesday afternoon pool party was in full swing, so most guys were by the pool. Still, a few guys were getting their hot soak on in the indoor sauna—men of all ages, ranging from 23 to 65, and from all over the United States—Atlanta, Florida, Chicago, and New York.

It’s easy to strike up a conversation in a place like Island House. Introduce yourself, ask where they’re from, if they’ve been to Island House before, and if so, what keeps them coming back.

If there’s a lull in the conversation, but you two sustain eye contact, you can cautiously veer sexual. Put your hand on their thigh. If they don’t move it, slowly raise it until you reach their dick. Give it a grab, start stroking, and lean into a kiss.

That’s precisely what happened with Luca, an Italian lawyer who now lived in the States and was staying in Key West for the winter. The seamless transition from casual talk to our hands on each other’s cocks, our lips locked—there was such a beautiful simplicity. What if every social interaction were this effortless?

After making out for a few minutes, I sat up on the perimeter of the jacuzzi, my legs still in the water but my hard cock out on full display. He waded in between my hairy thighs and started to suck. He swirled his tongue around the base of my dick, then slowly lifted his head, stopping at the sensitive point of circumcision, where the shaft meets the head. He started to suck my head gently, and my dick pulsed in his mouth. When he bent over fully and arched his back—his ass rising out of the water like a submarine surfacing—I counted my lucky stars. The man was either blessed genetically, religiously squatted, or, most likely, both.

I placed one hand on the back of his head and gently pushed down while using my other hand to reach over his long, muscular back to give him a light smack on his ass. I slid my fingers inside his smooth hole. He shuddered as I wiggled past my first knuckle—his asshole softer than 1000-thread-count Egyptian cotton.

A couple entered during our scene and marveled along with the other viewers, now totaling six naked men, most erect. I wanted to put on a show for them—a non-verbal declaration that the Boyslut had arrived. No dick would be left undrained. No asshole left unfilled. Any and all sex you want to have, come find me—my room number is 209. No man will be turned away.

But when I suggested we put on a show that would rival Cirque du Soleil’s Zumanity, Luca blushed.

“For the first time, I prefer alone,” he said.

“Of course,” I replied, masking my disappointment. But my letdown was short-lived as when Luca stood up from the jacuzzi, I could now see all of him—and he was a pitbull of a man. Muscle and meat. Beefy and thick. Just how I like ‘em.

Luca led me to the more private, single shower that reminded me of a 1930s hotel, golden arches—very art deco. The shower has two silver safety rails across one another. When Luca bent over, I grabbed them and thought to myself, Damn, this place thought of everything. They know we’re going to fuck in this shower, and so they added guard rails to make sure we don’t slip and die. How thoughtful!

What’s more, holding onto the rails meant I could plow harder, faster, and deeper than I could by just holding onto his hips.

And so I began to put on a show. Not for others but for myself. I lubed up Luca’s glossy hole and generously slathered my cock. I held onto the rails, leaned back, squeezed my glutes, and thrusted.

“Holy shit!” he said.

“Good boy,” I said. With just those two words, he became puddy in my hand.

“Am I a good boy?” His voice was desperate for my approval.

“Such a good boy,” I replied, and though I could not see his face, I swore I could have heard him grin. I slapped his ass and kept pounding, watching his glorious behind ripple with each thrust. His asshole felt like a black hole, sucking me in—and I wanted nothing more than to be consumed. I would have burrowed my entire body up inside his hole if I could have.

“You want harder?” I asked.

“Yes, please,” he begged. I’m not sure why I asked that question because I was already going as hard as possible, but that meant it was time to give one hundred and ten percent. To push past what I thought possible. To push my body to the limits. The extreme.

I clenched my abs and went even harder. “Good boy,” my voice crescendoed. I gave his ass another slap, claiming him as my own, as my bottom.

While I wanted to last forever, my body needed a break, and I had to believe he did, too. So I pulled out. He rose and turned to kiss me, stroking my cock vigorously, desperately, like he needed my milk to survive.

“I want Daddy’s cum,” he said.

“Okay, baby,” I said. “Slower and focus on the head.” He was indeed a good boy, listening to directions. My legs started shaking, and I grabbed the handrail for support.

“It’s coming, baby,” I said as my asshole puckered. He sped up his stroke ever so slightly, and my thick, gooey load shot out of me. My cum was fleeing from my testicles, like prisoners breaking free during a jailbreak. I roared, unashamed, unbothered by who might hear. That’s one of the joys of Island House. You can be loud when you fuck in public, not like with typical outdoor cruising. So I reveled in my shout, in being free to express, and it made my orgasm that much stronger. I felt pleasure from the tip of my dick, down to my big toe, and up to the curls on my head. I felt like I was going super-saiyan.

When I finished, and the final drop oozed from my still-hard dick, I saw Luca’s face. Overjoyed would be an understatement. He was both proud and sated; I could see it in his glistening eyes.

We said our goodbyes, both acknowledging that this wouldn’t be a one-time thing. The sex was too good. I went to grab my phone and saw it was only 4:30 pm. I had been at Island House for a total of thirty minutes and already had came, saw, and conquered, though not in that order.

I had officially arrived. Now I was ready for what—who—would cum next.