Let Us Sex-plain: Did I lose my virginity?

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!

If his penis was in my vagina, but no one came, is that considered a loss of one’s virginity?
—Susie, Manhattan

Susie, do you want it to be? I find the definition of loss of virginity as first insertion to be incredibly limiting and not sex-positive. That definition focuses solely on men’s pleasure (two-thirds of women don’t come from insertion alone) and doesn’t necessarily include people who may have sex in different ways, such as lesbians or those with certain disabilities. I heard something from Girls & Sex author Peggy Orenstein on a Fresh Air podcast (look it up, now!) that I’ll never forget: What if we defined loss of virginity as one’s first orgasm? That would help bridge all sorts of gaps in sex education and equality in the bedroom. Imagine a world where sex ed taught kids openly about sexuality, safety and mutual pleasure, rather than “Here’s how ejaculation works, and you better not get pregnant!” For now, Susie, you and only you get to decide when you’re not a virgin anymore.

What sex toys do you recommend for a heterosexual couple just starting to incorporate them into their sex life?
—Gloria, Upper West Side

I’m psyched for you, Gloria! Let’s start off slowly. You can always try a small (three inches or so), ribbed vibrator or bullet meant to enhance clitoral (or anal) stimulation; either of you can control it and try out different positions (it can take some of the pressure off the man to help you come). For him, try a cock ring (there are vibrating ones, too!)—it can help him last longer and come harder. There are also plenty of sex toys that have parts meant to stimulate a man and a woman simultaneously; there are models that go inside of you alongside his shaft or ones that have parts to cup his testicles and tickle your clitoris. Still too advanced? Tie each other up with neckties or use a feather or some other soft, clean household object to tease and please.

I keep getting asked to be in threesomes, which can be fun, but I’m worried I’m wasting my time. Should I cut off my fun and just go on dates with people who might actually want to date me or enjoy the couples who keep propositioning me?
—Louie, Bushwick

Talk about champagne problems! If you’re feeling guilty about all the carefree sex you’re having, fuck all that. Be safe and live it up (while you still can, because a relationship will almost certainly come your way eventually). But if you’re interested in a relationship, guess what: You can both go for romps with courageous couples and date people you could potentially be with more seriously. It’s like the twofer passes at Disneyland; you can visit both amusement parks as much as you’d like!

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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.

By: Jillian Anthony

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