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Let Us Sex-plain: I can’t stop thinking about the best I ever had

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

By Jillian Anthony

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 in a happy relationship for a year, but I find myself thinking—and fantasizing—about a guy I slept with a few times before I met my boyfriend. I have a good sex life now, but this other guy was the best I’ve ever had. Should I read into the fact that he still enters my mind?
—Josie R., Park Slope
You never forget your first time—or the first time someone makes you come in an earth-shattering way you never thought possible. Given the fact almost all romantic relationships come to an end, most people don’t end up with the person who made them scream so loud their neighbors started an eviction petition. But that doesn’t mean we don’t think about this sex god fondly—sometimes in the shower or with a vibrator in hand. You can bet your boyfriend has a fully loaded memory bank of his past trysts as well. As long as you’re into the person who’s actually, you know, in you, it’s perfectly fine to use your imagination now and then.

My boyfriend and I are the same age—early thirties—but I always want more
sex than he does. Should I be worried?
—Linda, Upper West Side
Unlike the women on TV who tell their husbands, “Not tonight, honey,” many of us want to take a trip to bone town just as often as men do, if not more. If your boyfriend’s sex drive has been this way for some time (after the initial passion simmered down), he may just have a lower libido than you do. That’s not necessarily a reflection on you or your relationship, but it’s unlikely to change and could become a larger problem down the line if you’re unsatisfied. See if you can find a sensitive way to begin a conversation about your sex life with him—less “Why don’t you want me?” and more, “I feel like we’re on different schedules when it comes to sex. Can we talk about that?” Of course, there are pills for these kinds of things—but don’t bring that up when first broaching the subject.

From a simultaneous stimulation standpoint, is clitoral, vaginal and anal stimulation at the same time desirable for a woman? Or is that triple action too much?
—Vincent, Upper East Side
No two ladies are built the same. Our bodies are mysterious wonderlands just waiting to be unlocked, and that’s part of the fun! Most women only come through clitoral stimulation, so that’s a safe bet. But that’s not to say some women don’t enjoy a little Twister action now and then (left hand on yellow, right hand on blue, tongue on red—you get the picture). If you’re up to the task of hitting all three at once, we welcome your determination. Just check in with your partner along the way.

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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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