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Jack Bailey
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Jack Bailey
Max Lorde Helps Stepbro Jack Bailey Prepare for Prom Night on Brother Crush
HARDCORE
April 4, 2022
DARKLADY
Marcus Rivers and Jack Bailey Make Out Until Legrand Wolf Joins on Scout Boys
HARDCORE
March 22, 2022
DARKLADY
Marcus Rivers and Jack Bailey Rightly Earn Merit Badges For Fucking From Legrand Wolf Over at Scout Boys
BAREBACK
March 21, 2022
HANK ORSO
Uncle Jax Thirio Teaches Jack Bailey and Max Lorde How to Bathe Efficiently
HARDCORE
February 22, 2022
DARKLADY
Boys at Camp Scouts Jack Bailey and Grey Gold Increase Their Skills
HARDCORE
February 21, 2022
DARKLADY
Jack Bailey and Max Lorde Crave Uncle Jax Thirio’s Family Dick
HARDCORE
February 15, 2022
DARKLADY
Jack Bailey and Grey Gold “Whip ‘Em Out” For Scoutmaster Greg McKeon in Boys At Camp
BAREBACK
February 14, 2022
HANK ORSO
Daddy Romeo Davis Loves Twink Loads from His Boy Jack Bailey
HARDCORE
February 3, 2022
DARKLADY
Start Your Week With a Double Dose of Twink Dick in Daddy Ass
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January 17, 2022
HANK ORSO
Jack Bailey Administers an Unorthodox Peer Anointment on Missionary Boys
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January 17, 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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