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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
MUSCLE DADDIES
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
HARDCORE
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
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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
DARKLADY
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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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