Island Sex Stories

Island Sex Stories
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Zachary Zane
Zachary Zane is a Brooklyn-based writer, speaker, and activist whose work focuses on lifestyle, sexuality, culture, and entertainment.

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"It wasn't like the 'hot' guys were only hooking up with other 'hot' guys. It was a weirdly welcoming orgy."
Last year, I was tasked with writing a list of the best sex resorts for Men's Health . I've been on more than a few such vacations myself , and included some of my faves on the list. But there was one I added, Island House , that I hadn't been to, although I felt like I had, given how much my friends had gushed about the Key West destination over the years. The place describes itself as a sex-positive, clothing-optional resort for men; my friends have described it as "much chiller than any Atlantis cruise."
After the Men's Health story ran, Island House invited me to come down for a few days to get the full experience. At first, I was excited to go. Food, drinks, naked men, Florida sunshine: it sounded like a queer man’s paradise. (This was right before the Omicron explosion, FYI.)
But after I agreed to attend, I got a little anxious: namely, over what the crowd would be like. The crowds are why I steer clear of going out in Hell’s Kitchen and West Hollywood, the gay clubbing capitals of New York City and Los Angeles, respectively. The venues tend to consist of identical-looking Ken Dolls—the kind of guys who put "no fats" and "masc only" in their Scruff bios.
Ironically, if anyone could have an easier time going out in these places, it would be me. I fit that idealized gay mold to a tee. Yet, despite my appearance, I still feel wildly insecure in these spaces; when I approach someone I find cute, they'll often look me up and down, their demeanor giving off a “Why did you bother coming up to me?” vibe. (Sir, you and your mean-girl clique could have saved money by drinking vodka sodas at home if all you wanted to do was talk to each other! But I digress.)
I bring this all up because I worried that Island House—and all of Key West, for that matter—would be like Hell’s Kitchen. I didn’t want to travel down to Florida to get rejected with my dick hanging out, which feels especially personal.
From Island House’s website, I couldn’t get a sense of the vibe. As I got ready, I mentally and physically braced myself for a Hell's Kitchen experience; I even squeezed in an extra trip to the gym beforehand, as if that would do anything!
Jeffrey, Island House's General Manager, picked up me and my boyfriend, Jonzu, at the airport, and drove us 15 minutes to the resort, which was tucked away in an otherwise residential area. From the outside, there was no indication that dozens of beefy dudes were letting their testicles hang low by the pool within.
The guy working the front desk, Gordon, was a former drag queen with strong Harvey Fierstein vibes. Within seconds of meeting him, I was nearly on the floor laughing. Needless to say, I've never had such a pleasant experience with any doorman in Hell's Kitchen.
After a quick tour of the property, Jonzu and I changed into our swimming briefs and headed to the pool. There were some guys there: most wearing Speedos, but a few lounging and swimming in their birthday suit.
At the pool, I was still too nervous to talk to anyone, but after a few drinks, we sauntered to the hot tub, dropped our Speedos, and plunged in. Hot tubs, I’ve realized, are a great place to socialize because you're all sitting there facing each another—you basically have to talk. At the pool, where you need to swim over to chat to someone, it’s much more of an approach.
I said hello, and I was not met with judgmental glances or curt dismissals—just equally enthusiastic hellos and getting-to-know-you questions. More men kept joining, and before we knew it, the tub was filled with 15 stranger talking to each other. Everyone was friendly—and while that should be the norm among gay and bi men, it hasn't been the case for me in Manhattan. It was a novel experience.
"There aren’t many spaces for queer men to just connect, without the pressure to hook up ASAP."
The hot tub hang wasn't sexual—at least, not at first. It was just some naked guys hanging out and getting to know each other. I feel like many gay spaces are super-charged sexually—and don’t get me wrong, I enjoy that, too—but there aren’t many spaces for queer men to just connect , without the pressure to hook up ASAP.
That said, once the sun went down, things did get sexual, and I wasn't complaining. One guy who was quite endowed got hard, and lord knows the gays can be size queens, so another guy started going down on him. Before you knew it, everyone was sucking and making out with everyone. It wasn't like the "hot" guys were only hooking up with other "hot" guys. It was a weirdly welcoming orgy.
Later that night, Jonzu and I ran into a few guys from the hot tub at Bourbon Street Pub, one of three main gay bars in Key West. We waved and went to sit at our own table, when one of them said, “What are you doing? Come join us!”
Pleasantly surprised, we obliged. Eventually, another gaggle of gays sat down next to us, and announced that we all needed to head to a bar called Saloon for the “competitions.” As one guy explained, Saloon invited men up on stage to compete in various categories, including best chest, best dick, "gayest-looking," and sexiest couple.
Saloon was a clothing-optional bar, which I hadn't realized. In fact, one of the evening's hosts was nude, and he proudly proclaimed he had a whopping 32 piercings on his dick. (I was so enamored that at one point in the evening, I sucked it.)
Then the competitions began. (I won best chest!) Once the final category—best dick—produced a winner, the sex commenced. In all my years living in New York, I’ve never been to a public bar where you could have sex anywhere you want. There’s usually a back room in gay bars if you’re looking to get down. Not at Saloon. I did it the back room, which was set up like a prison cell; a stranger went down on me in one of the glory holes; I boned one guy outside while five guys watched; and then I had sex right next to the bar.
“Is it always like this?” I asked the bartender. “Is everyone always this... down? ”
“Every weekend,” he replied without missing a beat. “It’s why people come to Key West: the friendliness and freedom.”
The next day, my boyfriend and I took a catamaran around the keys and went kayaking and snorkeling. That evening, we had a hot foursome in our room. Nothing too crazy.
The final day was Sunday, when Island House had its big daytime party from noon to five. By now, my confidence was at an all-time high. The last three days had instilled a courage in me that I'd never had meeting groups of gay men before. So, I spoke to everyone. Some guys were initially taken aback by my aggressive friendliness—they, too, weren’t used to attractive queer men being nice. I'd see their look of surprise when I'd swim over and say, "Hey! I'm Zach great to meet you." While they'd reply with their names, I could sense their trepidation. They weren't sure why I was talking to them, but once they realized my warmth was genuine—I was simply looking to make friends—they opened up (figuratively and, in some instances, literally).
I ended up meeting an attractive Italian couple by the pool, and started blowing one of them under the water. We ended up heading back to the room with my boyfriend. Along the way, we saw a straggler, and asked if he wanted to join; he said yes, and the five of us went to town having sex in every which way. By the time we all finished, my legs were trembling. Still, I managed to return to the pool to finish schmoozing. By 9 p.m., Jonzu and I were exhausted as the last few days caught up with us. I honestly didn't think I had ever socialized that hard in my life.
The following day, while hugging my new besties goodbye, one man I had gotten to know well asked if he could share something with me. When I nodded, he said, “I thought you’d be too much of a pretty boy from New York City to get down, but I was wrong. You definitely like to hang.” Clearly, I wasn’t the only one who’d struggled with NYC pretty boys before.
It’s wild to think that in three and a half short days, I felt like I had made lifelong friends. I felt like I had a community—a gay male community that I haven’t been able to find in New York despite living here for four years. Many of them wished me Happy New Year a few days ago, and there's one couple Jonzu and I are planning to visit in Atlanta.
Island House and, frankly, all of Key West is the best of what gay culture has to offer. It’s what gay culture could be if we opened up more and judged each other less. I would love the vibes could spread to cities like NYC and LA, but I'm not sure it'll happen, since Key West is a gay vacation town; people go with the mindset of having fun and meeting new people. They don't worry what others will think of them, because they'll (likely) never see them again.
Still, I'm going to do my best to bring my Key West mindset the next time I get dragged to Hell's Kitchen. Who knows? Maybe the boys will pick up on my non-judgmental vibes and match them.

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One couple allegedly left their wedding ring behind after having sex in the bathroom at Balthazar.
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Were you having sex this weekend in the bathroom at Balthazar and left your wedding ring behind? No worries! The staff has it.
In an XXX-rated lost-and-found post that reads like an erotic novel, eccentric restaurateur Keith McNally posted his manager’s account of a recent evening at the eternally hip Soho spot, which included things like the number of covers, walk-ins and cancellations, plus a saucy aside.
“We had one alleged report of a couple having sex in one of the men’s stall downstairs,” reads the manager’s notes. “But when I asked floor manager Greg to rush down and check what’s going on, the couple were nowhere to be found so they remained a mystery.”
But the steamy tale turned into even more of a tantalizing whodunit — as it appears that the woman’s ring fell off while contorting around the tiny stall.
“Oddly enough, Greg found a small wedding ring on the floor of the bathroom stall. He put it [in] Lost & Found,” reads the post.
McNally tells us the couple has not yet returned to claim the ring.
We are choosing to believe the randy pair are married to each other, not other people.
McNally has become known for posting all sorts of controversial things on Instagram, and frequently calls out his A-list customers.
He publicly shamed real estate developer Michael Shvo after the millionaire allegedly waltzed past the hostess at Balthazar to head right to the best booth . McNally threatened to ban him and said, “This obnoxious, entitled behavior is the Height of Arrogance.” (Shvo’s wife claimed the story was more complicated, arguing that they behaved appropriately.)
He also banned Graydon Carter after the former Vanity Fair editor allegedly failed to show up for a reservation for 12 at McNally’s Morandi, calling him a “fancy F–ker” and saying that he “will never be allowed to make a reservation at one of my restaurants again. Never.”
“We will be making a donation today to the restaurant’s tip pool to cover what the staff would have made,” Carter told Page Six at the time.
Instead of backing down, months later, when asked by Town & Country what he wanted for the holidays, McNally grossly responded , “Graydon Carter’s head on a platter.”

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love help Love Island producers help you write recoupling speeches, says Shaughna Phillips
ISLE SAY! Love Island’s Antigoni Buxton looks incredible in barely-there bikini top
love help Love Island producers help you write recoupling speeches, says Shaughna Phillips
ISLE SAY! Love Island’s Antigoni Buxton looks incredible in barely-there bikini top
GLAM SQUAD Love Island stars' cosmetic surgery secrets including Andrew's unusual chest op
CHEEKY! Love Island’s Laura Whitmore lets slip couple’s secret sex act under the covers
LOVE Island star Arabella Chi showed off her incredible figure in a crochet bikini.
The reality star - who appeared on the ITV2 dating show in 2019 - stripped off to a nude two-piece for a series of stunning snaps.
Arabella , 31, smouldered at the camera as she enjoyed a sunkissed break in Ibiza, Spain.
The stunner showed off her toned abs and thighs, before bending over and flashing her bum.
She styled her hair in a bun and completed her holiday look with flawless makeup.
Arabella's fans were left hot under the collar, with one writing: "Absolutely stunning."
Arabella has never been shy when it comes to sharing sexy bikini snaps.
Last week, she posed for a series of raunchy new snaps on a trip to the South of France.
The former villa star looked like she was at risk of flashing her fans as she yanked up her sheer bottoms in the sunshine.
She captioned her pictures simply: "Good morning 💕."
Many of her followers were bowled over by the snaps, with one writing: "Sweet Jesus! 🙌."
Another wrote: "Can’t even deal with this 😍" while a third joked: "Careful. You'll give yourself a wedgie."
Arabella has been watching this year's series of Love Island , recently weighing on her favourites and not-so-favourites.
The star told Closer she believes Davide Sanclimenti to be a "villa chiller" and wrote: "He's good looking. But we need some more banter from him."
After exiting the villa on her series of Love Island, Arabella enjoyed a high profile romance with former show star Wes Nelson .
However, they split in 2020 after nine months of dating - with their age gap said to have been a factor.
X Factor in 'shock return to Channel 5' as Simon Cowell 'signs big money deal'
Love Island producers help you write recoupling speeches, says Shaughna Phillips
Hollyoaks' Sarah Jayne Dunn looks incredible in a black bikini
Love Island stars' cosmetic surgery secrets including Andrew's unusual chest op
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