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Digging Deeper with Dillon Diaz
Category
Digging Deeper with Dillon Diaz
Digging Deeper with Dillon Diaz: My HimEros Men’s Retreat Experience
DIGGING DEEPER WITH DILLON DIAZ
October 20, 2023
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Digging Deeper with Dillon Diaz: Diary of a Melanated Porn Star
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Digging Deeper with Dillon Diaz: Where Did All The Guys Go?
DIGGING DEEPER WITH DILLON DIAZ
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Digging Deeper with Dillon Diaz: A Step-by-Step Guide to Filming Gay Porn
DIGGING DEEPER WITH DILLON DIAZ
September 8, 2023
DILLON DIAZ
Digging Deeper with Dillon Diaz: My Sexuality
DIGGING DEEPER WITH DILLON DIAZ
August 10, 2023
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Digging Deeper with Dillon Diaz: Chatting with Baxxx
DIGGING DEEPER WITH DILLON DIAZ
July 28, 2023
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Digging Deeper with Dillon Diaz: The Milk Man
DIGGING DEEPER WITH DILLON DIAZ
July 6, 2023
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Digging Deeper with Dillon Diaz: Wall of Fame for the Sex Game
DIGGING DEEPER WITH DILLON DIAZ
June 15, 2023
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Digging Deeper with Dillon Diaz: Body-oddy-oddy Dysmorphia
DIGGING DEEPER WITH DILLON DIAZ
May 26, 2023
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Digging Deeper with Dillon Diaz: Tying the Naughty with Jake Waters
DIGGING DEEPER WITH DILLON DIAZ
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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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