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’m a 24-year-old virgin, but I’m starting to date more now. When things get hot and heavy, do I tell the guy? I don’t want to give a guy performance anxiety, but I don’t know if not telling him is deceitful or might set myself up for a painful experience.
—Cait S., Park Slope
If you prefer that the person you’re with knows it’s your first time, then you should tell him. Sure, it could frighten some partners, but that’s a risk you have to take if you want to be fully in control of your first time—and you’ve waited this long, so you might as well be! If you just want to get the damn thing over with at this point and don’t want to tell the guy, I don’t think that’s deceitful. Lots of sex happens without either partner disclosing their past experience first. But first-time experiences vary wildly from woman to woman, and there can be lots of pain and bleeding or none at all, so there’s no way to tell quite what yours will be like. Just try to make it as positive for yourself as possible. Plenty of folks had their first time while drunk in a car, so you likely have a big head start comparatively.
How many orgasms can a woman have during sex? I’ve had more than eight with a friend with benefits, but everyone says this is impossible. Who’s right?
—Pia L., Chelsea
Only you know how many orgasms you’ve had in one sexy-time session, so it clearly is possible. (My record is about three times what yours is. Yes. Seriously. Stop bugging your eyes out like that.) I don’t know if there’s a maximum number that’s possible, but we should all shoot to break the Guinness World Record for that one.
My girlfriend and I recently had a spontaneous voyeuristic experience with another couple, but we lost contact with them. We had fun and would try that again but aren’t ready for a swingers club. How do we dip our toes in the water?
—Mike L., Park Slope
There’s an app for that! Download 3nder, which helps singles or couples find extracurricular partners. Specify that you’re looking for a voyeuristic situation rather than direct participation (if that’s true). Then, once you and someone you’re interested in both swipe yes and you’re all on the same page, you can set up a rendezvous—it’s an easy way to explore opening up your relationship. You don’t have to use real names or pictures of your faces on 3nder, and though you do log in through Facebook (so the app knows you’re real), you can use incognito mode. Alternatively, you can create a Tinder account together that explains what you’re looking for, or try Whiplr for exploring kinks. Or turn off your phone altogether and flirt with the next couple you’re digging at the bar.