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Jack Bailey

Derek Allen Shares Stepson Jack Bailey with Boss Isaac Parker on Family Dick
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Derek Allen’s Promotion Bid Leads to Sex with Boss Isaac Parker, Pool Boy Taylor Reign and Stepson Jack Bailey on Family Dick
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Derek Allen Has Poolside Sex with Horny Stepson Jack Bailey for Family Dick
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Jack Bailey Dumps Some DNA in Hot Daddy Romeo Davis for Twink Loads
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Troye Dean and Jack Bailey Catch Lance Charger Jerking Off on Scout Boys
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Here’s a Double Dose of Twinks Topping Daddies To Bring You Into Your Weekend
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Jack Bailey Sucks Max Lorde’s Cum-Filled Ass Clean for Brother Crush
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Cybersocket Awards Spotlight: Twink of the Year
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Cybersocket Awards Nominee Jack Bailey Twinks It Up With Hot Daddies In Two Scenes
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Dr. Johnny Ford Fixes a Patient Jack Bailey’s Dick on Doctor Tapes
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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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