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Even William Shatner Couldn’t Beat This Deal

HARDCORE

The trope of driving off to seedy pay-by-the-hour motel to have exciting, dirty sex has been around forever. But, when we have the money at least, we find that dirtying up a nice hotel room can be even more satisfying.

After all, having dirty sex in a dirty motel just adds to the scenery. It's kind of expected. But when these two walk into a nice hotel with sophisticated black and white framed photographs and plush, high thread count bedding to have dirty, nasty gay sex, it feels even more naughty.

Hotel Sex

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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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