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The Island House Key West

Island House Key West’s Jeffrey Smead Dishes on Clothing-Optional Pride, Sexual Liberation, & Gilbert Baker’s Sea to Sea Flag
Island House Key West’s Jeffrey Smead Dishes on Clothing-Optional Pride, Sexual Liberation, & Gilbert Baker’s Sea to Sea Flag
PRIDE
AJ Sloan Goes to Island House Key West, Where The Drinks Aren’t the Only Things That Are Stiff
AJ Sloan Goes to Island House Key West, Where The Drinks Aren’t the Only Things That Are Stiff
BIG DICKS
Island House Top 5: AJ Sloan’s 5 Reasons to Drop Trou and Go Au Naturale
Island House Top 5: AJ Sloan’s 5 Reasons to Drop Trou and Go Au Naturale
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Get to Know The Island House Key West Pool Boy Zack
Get to Know The Island House Key West Pool Boy Zack
CYBERSOCKET EVENTS
F*cking with AJ Sloan: Reflecting on Fun Times in Fire Island Pines in Anticipation for The Island House Key West
F*cking with AJ Sloan: Reflecting on Fun Times in Fire Island Pines in Anticipation for The Island House Key West
F*CKING WITH AJ SLOAN
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    Cybersocket Ask Chad
    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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