Naked Boys, Nic Sahara, and Roaming Cocks at Island House Key West

Naked Boys, Nic Sahara, and Roaming Cocks at Island House Key West

For over four decades, the gay community has claimed Key West, Florida as its own and life has never been sunnier, naughtier, or more fun. Part of that island’s history is the both famous and infamous Island House Key West, the longest gay-owned and operated men’s resort in the entire world. Complete with a 24-hour restaurant, a bar that only closes for three hours in the dead of morning, an on-site gym, play areas, comfortable and plush rooms, model quality staff (hi Levi and Michael!), free channels of streaming porn, and a pool that is both relaxing and frisky—depending on your speed. Their Naked Pool Parties on Wednesdays and Saturdays are the talk of the town, complete with hot naked pool boys, free shots, extended happy hour, and great music…did we mention HOT naked pool boys?

This last week, Cybersocket was on the scene for our first visit to Key West with multiple Grabby and GayVN adult star Nic Sahara. Island House Key West has been a long-time supporter of Cybersocket and, under our new image, we thought it was a perfect time to stop by. We were treated to a week-long stay in their luxurious two-bedroom, fully loaded condo and direct access to um, ALL, the described amenities. Some things we can’t divulge, you’ll have to experience it yourself…just pack plenty of lube and suntan lotion.

The resort was packed, but not uncomfortable. And though there were a number of muscled, hung guys on the scene, it was also extremely diverse with older and younger generations and all different body types enjoying the resort. Couples and singles were looking to play—visitors and Island residents alike—but for those who just wanted some downtime, the lounges were also home for guys reading a book or taking a nap. It was an adult Disneyland with a little, or big, something for everyone.

After an early flight from Los Angeles, we arrived at the too-cute-for-words airport in Key West stepping off the plane into the warm, tropical weather…we couldn’t resist a quick pic. Not five minutes off the plane, we encountered our first cock.  They run the Island and roam free…and yes, pun intended.

We were picked up in style by Island House’s Resort Manager, handsome James Braun. He and his husband, Island House’s General Manager and marketing king, Jeffrey Smead, make up the dynamic duo that has kept Island House thriving through the pandemic and setting the bar high for any other resorts around the globe. They actually met over a decade ago when James came to stay at Island House, the sight of Jeffrey in his shorts with a clipboard in hand was too much to resist. The ride to the resort was full of palm trees, water views, people on scooters and bikes, and yes, more cocks. James gave us the rundown on the history of the Island that includes high-profile celebs like Tennessee Williams, Ernest Hemingway, President Truman, and even The Beatles.

We got a tour of the expansive property, all adorned with disco balls and holiday finery, with some of the guests already, um, very happy to see us. We dropped off the bags, changed into tanks and shorts, and hit the Island House Café…happy hour had begun. Not only is their menu eclectic, but the food is also top-notch. Residents get free drinks during happy hour that come with a warning…they are strong!  Well, yes they were, and quite delicious. The devastatingly attractive bar staff kept our attention well into the night and the growing crowd made for boisterous hours of chat, everyone was in a great mood.

Not worried about jet lag, we had to hit the scene. We headed to the “Pink Triangle,” the gay area of the quaint city with popular joints like Bourbon St. Pub, Aqua Nightclub, 801 Bourbon, Sidebar, and Saloon One. There was a lot to take in as each venue had its own intoxicating atmosphere, hot guys, and strong drinks. Drag shows are very popular in town and have a different energy than other major cities. Every gay bar we went to also had a large group of straight patrons that were enjoying the sights as much as we were. For those wishing for a more intimate gay bar experience, some of the bars had a back area that was for men only, clothing-optional, and with play areas to get more…acquainted. By the end of the evening, we had accumulated a group of new friends—residents and fellow visitors alike. We ended up back at Island House, falling in love with their evening bartender who works from 11 pm to 7 am. We drank up until the last call at 4 am. Let’s just say the evening ended there, but it did not.  Wink, wink. An evening piece of chocolate cake from the bakery section wasn’t the only thing taken to bed.

Awakened by the sounds of the Island cocks at the crack of dawn, we hit our first Island House Café breakfast. Cuban sandwiches, build your own omelets, chocolate and banana croissants, and more were paired with some of the best morning coffee you could ask for. While some guests slept in, others were already for more fun or an early swim. We were ready for day drinking and headed back to the Pink Triangle. We met more of the locals and the daytime bartenders, including a sassy actor/bartender who kept us on our toes. As luck would have it, Dominic Ford, owner of JustFor.Fans, decided to drive down from Fort Lauderdale to hang out with us for a couple of days. We definitely made a presence in the city and the resort, and even ran into a Stephen Sondheim look-alike who did NOT enjoy our musical theatre jokes. Even with the allure of the architecture and energy in the downtown area, we headed back to Island House in time for happy hour…the resort truly has everything you need without having to leave.

After some pool time and rest (kind of), it was time for Wednesday night’s Hump Day Naked Boy Pool Party. The party is already a weekly highlight for the Island, and the resort opens to the public with drink specials and free shots. Adding our friend Nic Sahara to the proceedings just increased the energy. Not only was Nic on the scene, but Island House’s regular pool party boys joined in the fun…first in colorful speedos, then in nothing but a smile and swinging member. The music was pumping, the conversations were thriving, and the drinks kept coming. It was a really, really fun time. Owner Bobi Lore stopped by to meet us and enjoy the evening as well. Not only was the pool party a success in terms of fellowship and freedom of sexuality, it actually turned into a great networking opportunity for businessmen across the nation. Business cards, phone numbers, and Grindr profiles were equally shared. The fun continued well into the night for whatever fun you were looking for.

Before we knew it, it was time to have our final breakfast, amazing coffee, last dip in the pool, and head home. The flight home was very, very long, considering the fun we were leaving behind.  It is easy to see why Island House Key West is as popular as it is; the quality of the venue was beyond amazing, the staff as handsome as they are friendly, the managers accommodating to a fault, the crowd diverse & playful, the weather delicious, and that playroom…well…that’s another five stars. There's something to be said for having such a fun safe space on the Island that even the service industry staff from all the other bars and resorts come to play. We will be back soon!

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Also check out Island House Key West's Top 5 Travel Tips for Staying at A Clothing Optional Resort