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Illustration: Alex Citrin

Let us sex-plain: My hook up wants to make a sex video

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

Written 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!

This guy I’ve been hooking up with thinks it would be hot to film ourselves having sex and put it online with our faces covered. I’m intrigued but worried about trusting this person—I don’t know him that well—with video footage of me. What do I do?
Devorah G., Brooklyn Heights

If I could insert a GIF on this page, you’d see Judge Judy rolling her eyes and sinking into a deep, frustrated facepalm. Do not trust this guy, do not let him videotape any part of your body, do not pass go. I assume you’re not a Kim Kardashian–like socialite on the rise; if a video of your identifiable naked body (and God forbid your face) surfaces on the Web, I don’t see any positives for you. Women are regularly harassed and fired from their jobs because their scumbag exes post videos of them online (I’ll spare you the rant about how much less often men face those consequences). If taping yourself is something you must try, you hold the camera at all times, enjoy the video with your partner, then delete it immediately. Remember: Relationships end, but the Internet is forever.

What makes a vagina good—or even great?!?
Aurora, Bed-Stuy

Every vagina has the incredible capacity not only to bring pleasure but to create and birth mankind itself. If you have one, it’s fucking perfect.

I don’t want to be in a relationship right now, but I’m not interested in casual hookups for fear of STDs. What’s a sex-starved girl to do?
Natali, Upper West Side

If STDs are your main concern, take precautions. Wrap it up, use spermicide, grab a dental dam—whatever you need to lower your risk and make sex less stressful. Always be open with your partner about when each of you were last tested, but keep in mind that people lie. You could also pursue a situation I like to call the Unicorn Affair: Meet someone who you both enjoy hanging out with and sleeping with but who’s on the same page as far as keeping things chill. Make sure to be up-front about not wanting a relationship. (Don’t wait to throw that out there moments before penetration, or worse, moments after.) Oh, and a third option: Head to your nearest sex shop, grab a knowledgeable store associate, and find the sex toy of your dreams. Whether you choose something that shakes, rotates or freakin’ glows in the dark, you’ll be just fine.

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Read previous weeks' sex columns

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