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Jack Bailey

Max Lorde Helps Stepbro Jack Bailey Prepare for Prom Night on Brother Crush
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Marcus Rivers and Jack Bailey Make Out Until Legrand Wolf Joins on Scout Boys
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Marcus Rivers and Jack Bailey Rightly Earn Merit Badges For Fucking From Legrand Wolf Over at Scout Boys
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Uncle Jax Thirio Teaches Jack Bailey and Max Lorde How to Bathe Efficiently
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Boys at Camp Scouts Jack Bailey and Grey Gold Increase Their Skills
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Jack Bailey and Max Lorde Crave Uncle Jax Thirio’s Family Dick
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Jack Bailey and Grey Gold “Whip ‘Em Out” For Scoutmaster Greg McKeon in Boys At Camp
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Daddy Romeo Davis Loves Twink Loads from His Boy Jack Bailey
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Start Your Week With a Double Dose of Twink Dick in Daddy Ass
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Jack Bailey Administers an Unorthodox Peer Anointment on Missionary Boys
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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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