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Illustration: Alex Citrin

Let Us Sex-plain: I’m not sure if I’ve ever had an orgasm

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

By Jillian Anthony
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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’ve been dating my boyfriend for three years and I love him, but he’s never gone down on me. I’ve mentioned wanting it, and he says he’s just not into that. What do I do?
—Julie G., Ridgewood, Queens
In the words of goddess Amy Poehler, “If you don’t eat pussy, keep walking.” Human women are one of the only animals on earth who have an organ that is devoted purely to sexual pleasure! Whether you believe in Jesus, Krishna or Pizza Rat, you have to know that’s a gift from a higher power. Three years, Julie?!? Don’t waste any more of you and your clitoris’s precious time on this planet with someone who’s too selfish to go down on you—especially if he expects blow jobs. Sex isn’t tit for tat, but it’s certainly about mutual giving and respect. The man you’re with should revere your vagina in every way possible.

Is anal really that common these days? My boyfriend makes it sound like it’s been done on the reg in his dating life. While I find it enjoyable sometimes, it’s not as good—or fun—as conventional sex. Is something wrong with me?
—Nance B., East Village
Yes, anal sex is rather common, but no, nothing is wrong with you! A recent study from the National Center for Biotechnology Information showed that of more than 10,000 heterosexual women studied, 36.3 percent had tried anal sex but only 13.2 percent reported doing it in the last year. In other words, anal is on the menu for many women, but it’s not their go-to order. If you prefer the oysters to the pupu platter, that’s entirely your choice; you should only engage in sexual activities you’re comfortable with, whether your boyfriend’s done it with every girl he’s dated or not. And according to those stats, he probably hasn’t.

I’m not sure if I’ve ever orgasmed. Everyone says if you have to question it, you haven’t. So how do you know when you’ve experienced the big O?
—Emily H., Bed-Stuy
Dearest Emily, since I can’t know exactly how your lady parts are feeling, I can only speak from my own experience. When having sex, have you: felt in your clitoris a building crescendo, then epic release, much like the title song of Jaws, but instead of a shark attack, you were in the throes of a sexual frenzy? Made that face in bed that Doctor Grant does when he sees Jurassic Park’s dinosaurs for the first time? Had an Exorcist-like moment when you felt so insanely turned on, it was almost as if you were floating above the bed, your head spinning of its own accord? If the answer to all of these is no, it’s possible you haven’t experienced an orgasm yet. But you can and will! Be vocal with your partner about exactly what feels good for you until you experience a cinematic simile of your own.

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let us sex-plain
Photograph: Shutterstock

Let us sex-plain

Sex and dating

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

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