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Let Us Sex-plain: How can I convince my girlfriend to try anal?

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!

What’s the best way to convince a girl who’s scared to do anal to give it a try?
—Mark, Nolita

First of all, it’s not your job to “convince” anyone to try anal. If your girlfriend is scared, it’s likely because she’s heard it’s painful, and that’s an entirely valid reason to be hesitant. If she’s willing to discuss giving anal a shot, a great place to start is exploring butt play to see if oral or digital stimulation is something she enjoys. Educate yourself on how to make anal sex more comfortable (a lot of lube, with her on top, so she can control penetration). And if you’d like her to give butt sex a go, you’d better be willing to do the same. Offer yourself up for some pegging experimentation—then maybe you can “convince” her from a place of empathy.

Guys I sleep with seem so annoyed when I ask them to wear a condom. The one I’m currently doing it with always tries to put it in without a condom, and it’s infuriating. What can I say to get it through his head?
—Emily, UES

I’ve been in several sexual situations where the responsibility of protecting us both from STDs or accidental pregnancy is completely on me, because my male partner would rather just put it in. (One shining star flat out refused to sleep with me because I asked him to wear one. My vagina and I got the hell out of there and never saw him again.) I’m sick and tired of it, just like you are, Emily. If a woman asks you to wear a condom, you wear one, and don’t continually whine like a toddler about the fact that you have to do it. Sexual safety is not up for debate—nor is consent. Just because the crushing force of the patriarchy makes the consequences of casual sex abundantly worse for women than men doesn’t mean it’s all on us ladies to make adult choices! Emily, dump this guy immediately and send him and his condomless dick on their way.

I’m a virgin, and I’m dating again after the end of a long-term relationship. Any advice for someone trying to date-while-virgin here?
—Nicole, Queens

You’re not the only virgin in New York City—I’m not sure how old you are, but believe it or not, about 20 percent of people graduate college as virgins (I was one of them!), so don’t feel alone or discouraged. If you’re interested in a serious relationship, I’d give you the same advice as anyone else: Date with purpose, make your intentions known, and be patient. It might not be easy to find someone willing to wait in this sexed-up town, but you will eventually meet a partner who wants the same things as you.

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Read previous weeks' sex columns

Let us sex-plain

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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By: Jillian Anthony

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