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Ask Chad: Holiday HookUps, Homewreckers, & Roommate Sex…Oh Myyyy!
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F*cking With AJ Sloan: Why Gays Desire Daddies
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Grindr 2023 Unwrapped: Gay Hookup Culture in Review!
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Ask Chad: Friend with Benefits, Threesomes, & Blue Balls
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Ask Chad: Shady In-Laws, Bad Gifts, Peeping Pussy, and Holiday Sex!
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Ask Chad: Throuples, Uncut Dicks, & Freeloaders…Oh My!
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Sorry for Asking NEW Episode: Working Out the Kinks, Season 2 Finale
Sorry for Asking NEW Episode: Working Out the Kinks, Season 2 Finale
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Ask Chad: Holiday Sex, Cum Loads, and Go-Go Boys
Ask Chad: Holiday Sex, Cum Loads, and Go-Go Boys
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Sorry for Asking NEW Episode: Loads on the Roads, featuring Max Adonis
Sorry for Asking NEW Episode: Loads on the Roads, featuring Max Adonis
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Ask Chad: Daddies, Couch Surfers, and Coworker Crushes…Oh My!
Ask Chad: Daddies, Couch Surfers, and Coworker Crushes…Oh My!
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Ask Chad Love & Dating: OnlyFans Boyfriends, Phone Creepers, and Monogamy
Ask Chad Love & Dating: OnlyFans Boyfriends, Phone Creepers, and Monogamy
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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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