Let Us Sex-plain: Should I feel guilty about having phone sex with a married guy?

Your personal wingwoman, Jillian Anthony, answers all your questions about dating and doing it in New York

Illustration: Alex Citrin

I get it—being single in the city can be tough, and the ways New Yorkers are having sex these days can be surprising. But whatever your dating conundrum might be, I'm here to help. Consider me (Jillian Anthony, Time Out New York's Senior Things to Do editor) your personal wingwoman, guiding you through dating and doing it in New York in our weekly "Let Us Sex-plain" column. Check out my answers to all your questions online and in the magazine every Wednesday, and submit your own coitus queries below!

I have several warts (non-STD related) on my marble sack. Should I mention or explain this to new partners or just wait and see how it goes?
—Mike, Hicksville, L.I.

Your body has some imperfections? Cool, all of ours do too. Those warts (I’m trusting you’ve been checked out by a doctor) may be in a less-than-auspicious location, but try to embrace them, and go into sexual situations with confidence. I remember a time when I had some friendly relations with a man who had a pretty large, mole-like spot on the top of his penis. Did it freak me out a little bit? Yes. Did I say anything? No. Did I still have sex with him? You bet. So, if a partner asks about your lil’ friends, be honest. If you spot someone giving them a look, maybe explain the situation just to put them at ease. Otherwise, keep calm and carry on.

I somehow ended up in a hot-and-heavy phone sex thing with a married guy. We’ve never met and don’t plan to—and I don’t feel guilty about it. Should I?
—Amanda, Gramercy

I want to make it clear that I don’t condone cheating (though I do think our society’s emphasis on monogamy is disingenuous and limiting, but that’s a conversation for another day). And different people have different opinions on whether phone sex is “real” cheating or not (I think it is). But between you and your own personal Anthony Weiner, only one of you is married. He’s the one saying things like, “And now I’m bending you over the filing cabinet,” and violating his vows, not you. In a perfect world, no one would hook up with taken or married people, but I’m also sick of seeing women labeled as “the other woman” and “home-wrecker” when they’re not the ones who looked a human they’re supposed to love in the eyes and pledged fidelity. Ultimately, the married dude should be feeling guilty, and this is his cross to bear.

I’m a 29-year-old lesbian who’s never been in a relationship. I’ve only hooked up with one person, but I never let her put anything in my vagina. It feels like I am still a virgin. Am I?
—Rachel, Brooklyn

Virginity as a milestone is hugely overrated and taught to young men and women in really fucked up terms. How about, instead of measuring virginity by the first time something is inserted inside of us, we measure it by the first time we have an orgasm with a partner? That would be a much more sex- and female-positive way to approach sexual experience. In any case, if you still feel like you’re a virgin, be one! If your definition of sex doesn’t involve vaginal insertion, that’s cool! You can decide what course your sexual journey and identity takes—and it doesn’t matter what anyone else thinks.

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Let us sex-plain

Your personal wingwoman, Jillian Anthony, answers all your questions about dating and doing it in New York

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By: Jillian Anthony

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