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Island House Key West
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Island House Key West
Christmas Came Early for the Bears: WOOF Week!
BEARS
December 23, 2024
ALEXANDER
Get to Know The Island House Key West Pool Boy Zack
CYBERSOCKET EVENTS
April 5, 2023
AJ SLOAN
Cybersocket on the Scene: Dicks, Butts & Drinks in Key West with the Don Juan of Porn, Cesar Xes!
BIG DICKS
September 15, 2022
ALEXANDER
Cesar XES Shares His Top 5 Reasons to Go to a Naked Pool Party
BAREBACK
August 19, 2022
JOSHUA ANDREW
Cesar XES Headlines Island House Key West’s Naked Pool Party This August
BAREBACK
July 28, 2022
JOSHUA ANDREW
Rhyheim Shabazz, Luke Truong, Cade Maddox & More Win Big at the 2022 Cybersocket Awards! See the Complete List of Winners
AMATEUR
May 25, 2022
JOSHUA ANDREW
Cybersocket Awards Return with Sizzle, Celebrities, and Industry Winners
NEWS & PRESS
May 25, 2022
DARKLADY
I Can’t Bear the Wait… “Key West Bear Week” Finally Returns November 2022!
BEARS
April 28, 2022
TOMMY
Top 5 Clothing Optional Pick-Up Lines x Island House Key West
CIRCLE JERKS
March 31, 2022
ALEXANDER
Five Great Gay Clothing-Optional Resorts (Reading This Article Is Not Optional)
CRUISING
March 14, 2022
TOMMY
1
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Milo Miles Joins the Staghomme Cabal at Carnal+
January 17, 2025
BAREBACK
For the Love of the Harness: Kink & Fashion
April 1, 2025
BDSM
Final Destination Men and Their Nude Scenes
May 30, 2025
BUBBLE BUTTS
Hot Male Gemini Celebrities Showing It All Off! Part 2
June 16, 2025
CELEBS
Beware “Banksying” In the World of Gay Dating
July 28, 2025
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Hey Chad,
I am typically a top and have limited experiences bottoming, and the reason is because it hurts too much. Every time I go through the same thing, clean out, hype myself up, poppers, lube, and try taking it slow. But the outcome is always the same, it hurts and I can’t enjoy myself and then stop him after a few minutes because it is too unbearable. How do I bottom without it feeling like I’m passing a watermelon?
Thanks,
- Novice Bottom
Chad,
There’s nothing that ticks me off more than a flake, and lately, I keep getting ghosted on the apps. I get tons of messages when I first log on but by the time I am ready, or the later it gets, the more likely they are to flake on me and then I end up finishing myself and going to sleep. How do I get a hookup to come through?
SOS,
- Night Owl
Dear Chad,
I am a little annoyed to have to even ask this but what is the policy on paying for dates? I recently went out with a guy for the second time now and I had to pay for everything BlOTH TIMES. He didn’t even reach for his wallet when the waiter brought the bill, or when we went to the movies! I feel like that’s so rude, like it should be his turn the second time right? Or do I have to say something about splitting the bill from the beginning?
Thanks,
- NotUrSugarDaddy
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