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Illustration: Assa Ariyoshi

Let Us Sex-plain: I’m feeling shy about sex in my first lesbian relationship

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

Written by
Jillian Anthony
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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 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!

Like many women, I am most likely to get off sexually when rubbing and grinding on a guy while sitting on top of him. When we grind or rub to stimulate the clit, does that feel good for men as well?

—H, Soho

If you’re rubbing up on a dude’s dick in any way that’s not painful (and even then), he’s probably into it. A little rough friction can be a good feeling, with or without clothes on, though it would probably be a lot less likely for a guy to actually come this way. But, hey, enjoy yourself! Just beware of chafing.

How do I sexually escalate with a woman? I haven’t dated in five years and am a “nice guy.” How do I show signs to a woman that I want to make out with her, etc.?

—Kenny, Chelsea

In my experience the majority of “nice guys” that describe themselves as such are anything but. Still, I’m going to give you the benefit of the doubt ! Confidence is key, and the old adage “fake it till you make it” could serve you well. Work out or do something that makes your body feel good, wear a powerful outfit, and remind yourself that you are sexy! If you’re really struggling to make a move, using your imagination to emulate the characteristics of a suave man you really admire could give you an extra boost. (Idris Elba, anyone?) This may sound silly, but as someone who has stomped through a party with exaggerated shoulder movements à la Lady Gaga before, it can work! As far as actually making a move, it’s all about your body language. After a nice date, take her for a nightcap at an intimate bar. Sit close to her. Place a hand on her thigh or hold her hand. Lean closer as you speak to her and hold eye contact. And, if she’s reciprocating your advances, kiss her! If things are going well, ask her to come back to your place. If she’s into it, it’s that easy! You can also just say, “I’d love to take you home with me.” Being forward can be really hot. Just read the room.

My girlfriend and I have been dating for a while, but I only dated guys before her. She understands that I have no knowledge about lesbian sex, so we’re taking it slow. We started off good, but lately I’ve been feeling so shy when we have sex. She thinks it’s her, but it’s not. What could be wrong with me? How can I loosen myself up with her again?

—Danna, Brooklyn

Nothing’s wrong with you! You’re trying a form of sex for the first time, and that can be understandably intimidating. She sounds like a caring and patient partner, so why don’t you relax and let her take the lead? Your girlfriend is aware of your history and doesn’t expect you to be an expert on pleasing women right this second. Perhaps it would help if you shared your fears with her so she can reassure you that she’s happy to take things slow (and guide you!) until you’re more comfortable.

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