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Illustration: Alex Citrin

Let Us Sex-plain: My boyfriend is an awful kisser

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 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 met a guy (I’m a guy also) whom I clicked with on more than a sexual level. He lives in San Francisco but was in New York visiting a friend. We hooked up, and I ended up staying in his apartment for the next four nights; it honestly felt like a relationship. I’m going back to my home country of New Zealand in March, but I am planning on visiting him before I go. Should I put myself through that or just hold on to the good memories?
Jono, Chelsea

Go. Enjoy every second you have with this man. Record the texture of his skin in the membranes of your fingertips; memorize the hues of his eyes; tell him things you’ve never told a soul; linger in bed for countless, immobile hours. These kinds of connections are rare and life-affirming. Sure, you may mourn these moments once they’re gone (and you should go into this well aware that they will be), but don’t you dare miss your chance to experience them today.

My boyfriend and I don’t know how to kiss. When “passionately kissing” we just suck each other’s lips, and our tongues never touch. How do we learn how to kiss?
Lisa, Bronx

1. Start with a closed mouth, and go slowly. No, even slower. 2. Open your mouth a bit, and kiss a few more times. Keep that tongue at bay. 3. Touch your tongue to his, lightly, and keep the kiss-to-tongue ratio about three-to-one. 4. Don’t even think about sucking or biting (save that for when you’re a bit more experienced). 5. Remember to breathe through your nose. 6. Enjoy the push and pull of finding a comfortable rhythm. 7. Have him read these same directions (hopefully he has a sense of humor). Kissing should feel more like a gentle exploration and less like two vacuums battling to the death. Practice makes perfect!

I’ve only had sex a few times. I’ve found that I have trouble staying hard, but even more confusing is the fact that nothing turns me on more than pleasing my partner with just my hand. Is it possible that my hands are more sensitive than my penis?
Corey, Bed-Stuy

No, you don’t have some sort of hand-dick inception thing going on. You’ve just found exactly what gets you going! And it’s something that gets your partner off at the same time—lucky you. Maybe you love seeing or hearing her being turned on by what you’re doing, and that’s totally normal. So touch her all you want, and remember that sex is about much more than genital penetration and orgasm. Enjoy the experience—the beginning, the middle, and possibly the lack of a dynamite ending. You’ll continue to find new things that turn you on as you have more sex, so let go of any self-pressure you’re harboring, and know that your erection issues could just be newbie jitters.

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Read previous weeks’ sex columns

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