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Jack Bailey
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Jack Bailey
TikTok Hosts Some Titillating Porn Performers. Here’s 10 You Should Follow!
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September 17, 2024
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Twink Trade Has Daddies Switching From Daddy Ass to Twink Ass
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May 11, 2023
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At Disruptive Films, Refined Twunk Jack Bailey Learns Lessons from Blue-Collar Stud Clif Jensen
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April 18, 2023
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Jock Breeders Brings the Muscle Daddy On a Twink’s Ass with Jack Bailey and Killian Knox
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March 30, 2023
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Jock Breeders: Muscle Daddy Jax Thirio Takes Jack Bailey’s Twink Ass
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December 22, 2022
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Jack Bailey Faps Before Sex with Colton McKeon and Greg McKeon on Boys at Camp
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September 5, 2022
DARKLADY
Jack Bailey is Super Thorough Oiling Up Taylor Reign for Brother Crush
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August 24, 2022
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Derek Allen Shoots for a Promotion from Isaac Parker with Jack Bailey’s Help on Family Dick
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August 4, 2022
DARKLADY
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August 1, 2022
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Taylor Reign Goads Jack Bailey into Outdoor Activity on Brother Crush
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July 22, 2022
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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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