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Chad
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Chad
Ask Chad Love and Dating: Office Sex, Slutty Besties, & Lace Underwear!
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February 20, 2024
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Single on Valentine’s Day? I Got You!
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February 9, 2024
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January 31, 2024
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January 19, 2024
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Ask Chad: OnlyFans Fatigue, Neighbor Hookups, FWB…Oh Myyyy!
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Ask Chad: Hookup Lube, Viagra Sex, and Ex Husbands…Oh Myyy!
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January 7, 2024
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Ask Chad: Holiday HookUps, Homewreckers, & Roommate Sex…Oh Myyyy!
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December 24, 2023
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Ask Chad: Friend with Benefits, Threesomes, & Blue Balls
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December 17, 2023
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Ask Chad: Shady In-Laws, Bad Gifts, Peeping Pussy, and Holiday Sex!
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December 10, 2023
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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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