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New York We Love You, But You’re Not Getting Us Off

PORNSTARS

One more reason why New York City ain't what it used to be: not only are there no more leather bars, but there are also fewer and fewer places to have hot anonymous sex. If we didn't get to break out our leather armbands and watch Chi Chi LaRue and assorted porn boys roll into town for events like Folsom Street East this weekend, we might as well be living in, like, Cleveland or something! (Though something tells us they have more leather bars and anonymous sex than we do anyway.) (villagevoice.com; FSE photos by istolethetv @ flickr.com)

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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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