In the Land of Horny Gay Men, I Went on a Hero's Journey to Cum

I had an fivesome in the hot tub, fucked a muscle power bottom on the outdoor balcony, and got blown in the video room. God, I love Island House.

I was devastated I missed the hot tub orgy at Island House. Well, the evening hot tub orgy. I had more than my fair share of thicc, juicy ass at the afternoon hot tub orgy I had orchestrated. 

But alas, I was tired. I had too much fun during the day and could barely keep my eyes open, so when all the boys started kissing in the tub, I—in a very uncharacteristic move—actually excused myself. Unheard of. Unthinkable. The antithesis of being Boyslut. Hence my devastation. 

Well, I wasn’t going to miss evening shenanigans at Island House this time around, so after getting my dicked sucked in the Jacuzzi at Bourbon Street Pub, I headed back to the resort with some new friends, fellow horny travelers, where I proceeded to get my dick sucked at the outdoor Jacuzzi at Island House. (Really, Key West is all about getting your cock deepthroated in various bodies of hot chlorinated water throughout town.)

(Courtesy of Island House)

The five of us started in the outdoor Jacuzzi. One thing I love about spaces like Island House is I don’t need to be the firestarter who gets the orgy started. When five gay and bisexual men are naked in a Jacuzzi, dicks get hard. And when a man sits naked on the step of the Jacuzzi with his feet in the water and his erect dick on full display, we’re like moths to the flame. We just have to start sucking that dick. Or at least, I do. 

So in a way, perhaps, I was the firestarter again because I was the first one sucking an 8-inch uncut cock. I started slowly, licking his head and shaft before I even sucked. When I put his entire dick in his mouth, he arched up, getting that last half-inch down my throat. I gagged, and he said, “Yeah, take it.” 

I am a problematic bitch because I love that shit. I love when a guy holds my head down while getting blown. I know many folks do not. And for years, I hated it, but something changed. Maybe porn conditioned me? Maybe I started loving cock more? Whatever the reason, I love it now. (Still, if you’re getting head, don’t be an asshole and do it without testing the waters first and getting some form of consent. Unless it’s with me, as I am giving you consent now.)

The hung man stood up on a step, now entirely out of the water, excluding his feet. I went over to start sucking, exposing my hard dick. Quickly, a third man began blowing me. It was a chain of dick-sucking. A symphony of gagging. The harder he pushed me into his dick, the harder I pushed the third guy into mine. 

Two other friends were making out and watching the show; then, one requested we go to the indoor Jacuzzi. I wasn’t sure why. The weather was warm, and I liked being in public in case any men walked by and wanted to join. But he was insistent, so we wrapped our towels around ourselves and headed to the indoor Jacuzzi. 

On the way, I got a little distracted. I ran into a man I had been flirting with at the pool earlier that day. A man who made me audibly whisper, “Jesus fuck balls,” when he sat down on the lounge chair next to me. His soft blue eyes matched the water in the pool, contrasting his otherwise sharp face. His symmetric nose made a perfect 90-degree angle. His cheekbones could cut glass. His jawline was pronounced, even through his light blonde stubble. And I couldn’t help but look anywhere besides his face because he was shaved bald. Without hair on his head, I fixated on his facial beauty even more. 

Well, almost. I may or may not have stared a little at his body, which was nearly identical to Mark Wahlberg in his Calvin Klein ad. So you know, that didn’t hurt.

When he sat next to me at the pool, he started needlepointing. Needlepointing. So needlepointing is now officially a hot guy thing. It also made it very easy for me to strike up a conversation with him because I could ask about it. When he spoke in a deep and steady voice, it was like I was hit with a bottle of Rush. My asshole bloomed. I could have taken a fist right then and there. No lube needed.  

Well, like Pavlov’s slutty-ass dogs, my asshole opened up at the mere sight of this man, walking along the balcony of Island House alone at 1:30 in the morning. 

“What are you up to?” I asked, already knowing the answer. 

“Looking for trouble,” he said. 

“Well, I’m trouble,” I replied. There was a brief pause before I continued, “Do you want to—”

“Oh, yeah, absolutely,” he interrupted. “Do you have lube?” 

“I don’t.”

“That’s okay. We can grab some from my room. We have to be quiet, though. My husband is asleep.” (For the record, he and his husband were in an open relationship…allegedly.) 

We popped by his room and grabbed a bottle before deciding where to go. We could have quickly gone back to my room. But where’s the fun in that? We instead headed to the part of the balcony that overlooks the pool, dropped our towels, and began aggressively making out. Something about holding a guy’s shaved head while kissing him turns me on. But our makeout session didn’t last long because the moment I got hard, which was pretty damn quick, he dropped to his knees and started sucking me on the lawn chair. 

The angle was picturesque. He looked me in the eyes as he took me in his mouth. His big, muscular ass bounced behind him as he sucked. When he, on his own accord, would take me all the way down his throat, he’d gag, and I see his ass shake.

“I need you to sit on this dick,” I said. 

“Yes, please,” he replied with a grin. We started in reverse cowgirl. Like a gymnast, he held himself up with his arms and shoulders as he slowly lowered his ass onto my cock, inch by inch. All of me didn’t fit at first, but after a big breath, he lowered himself fully onto me. I then grabbed him by his hips and kept him there. I didn’t want him moving just yet. I wanted to feel every part of his insides. 

“Fuckkkk,” we both said in unison. I released my grip and let him ride my cock and set the pace. Each time, he’d pull out completely, so I could see myself entering fully with every bounce. I laid back and enjoyed the show for a few moments, but then I couldn’t help myself. I grabbed his hips and started pelvic thrusting hard and fast. My glute bridges at the gym paid off, and each thrust made a satisfying wallop sound. 

“Urgggggg,” he moaned. 

“Get up,” I told him. “And get on the floor.” He got on the cold deck. Usually, I’m one for comfort when I have sex, but I didn’t mind the hard edges of the floor. I turned his head to the side and kissed him as I pounded from behind. His asshole was smooth, open, and mine. 

After a hot thirty minutes, the two of us ran out of breath. We cuddled on the chairs before my friend joined us. 

“You didn’t tell me how good Zach could fuck,” the power bottom told my friend. 

I saw the cogs in my friend’s brain. He was determining whether or not to make a cunty joke but eventually landed on nodding. He left shortly after. 

“Want to fuck me?” I asked once my friend had left. 

“I actually have to be up in four hours to go snorkeling,” he replied. “Tomorrow night?” 

“I’d love that,” I said. We gave each other one final kiss before he headed back to his room. 

(Courtesy of Island House)

Now I still hadn’t cum, and I wanted to. So I headed to Island House’s video room, which is exactly as it sounds: a dark room with various pornos playing on the walls. Now I love a good video room. You know when you’re watching porn and wish you could watch multiple videos at once, but instead, you’re switching back between tabs? Well, in this video room, you don’t have to. There are different types of porn everywhere. Different men of different races, body types, and ages engaging in various sexual acts. All you have to do is turn your head, and you’re in a new scene. 

I entered, but alas, no one was there. It was pretty late at this point. So I hopped on the ~apps~ and started stroking, looking at all the porn around me. I started chatting with men nearby, and one guy said he could be there in two minutes to suck me off. Two minutes later, a 6’2, 250-pound father with a dad bod came in, dropped to his knees, and started sucking. 

He handed me his poppers, and I took a whiff, letting my head fall back. He sucked hard and deep, perhaps a little too hard. I need a light touch with intermittent pressure to cum, but I felt like explaining this would be too challenging. 

Instead, I told him to stick a finger in my ass. He did. “Another,” I said. And he did. “Apply pressure up,” and he did. I felt the pressure build and knew I was close, but I didn’t know where to look when I came. There was so much stimulation with him and all the porn around me. I ended up closing my eyes as I shot in his mouth, listening to his moans and the grunts of all the porn stars. It felt like each and everyone one of them was blowing me. 

Before I could thank him, he thanked me for the load, got up, and left the video room. I sat there for a few minutes, bathing in post-orgasmic bliss. Sure, I may have missed the evening hot tub orgy the night before, but I made up for tonight. That’s the best part of Island House. It doesn’t matter if you miss one sexual adventure; you can always make more.  

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