Talking to Strangers: Brooklyn, NY

Nerve asks deeply personal questions to people we just met.

By Sarah Rammos

Jay, 36

Does your job ever get you laid?
No, me as a person gets me laid. I think I'm a decent looking guy, I'm successful, I can be very charming when I want to be. Or I can be an asshole. I think sometimes women like guys who are kind of assholes. I think women are drawn to a challenge, and assholes are absolutely a challenge. I mean, don't you want to go home with me?

Where's the craziest place you've ever had sex?
I don't know how many times I've had sex with random women in bathrooms at bars and clubs. This one time I was really fucked up, doing some blow or whatever, and I saw these two really hot chicks standing at the bar. So I just walked over to one and said, "You should come with me to the bathroom. It'll be worth your while." And it worked. I had no idea if it would or not. I was fucked up. Just asked her to follow me. I turned around and had no idea if she was going to actually follow me or not, but when I looked she did and that was it. Never saw her again, obviously.

Have you ever been offended in the bedroom?
A girl tried to put her finger in my butt. It just doesn't work for me. Whether she'd asked first or not, it's just... no. Not my thing. I don't think I've ever done anything that put a girl off like that either. I don't really try to push my limits. I mean, if a girl is going to come home with you and have sex with you, don't try to overstep the boundaries.

Do you have a favorite position?
Good question. Either doggy style or cowboy style. It just looks gorgeous with her ass to the back like that.

What's the biggest age difference you've crossed in bed?
I slept with someone who was almost eighteen years older than me when I was really young. It was interesting. I was a little intimidated. I was young, I was a teenager. I was eighteen, and she was thirty-six. I was working in a hospital in the kitchen. She was a divorcee. I absolutely learned some things from her. I learned to slow down. You know, when you're seventeen or eighteen years old and having sex with a woman, you just tend to get so excited and really into it, and you just act crazy. You just go too fast. Older women just want you to relax and wind down. And I know that now. I'm an older guy. I've been around. I've learned.

NEXT: "Back in Iowa I had really long hair, so that got girls to notice me right off the bat..."

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