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Let Us Sex-plain: I couldn’t feel him inside of me

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!

I’m a 28-year-old female who recently had sex for the first time. The big night was fueled by a lot of alcohol, and it was a one-night stand. It was fun, but I’m scared by one thing: I couldn’t feel his penis at all when he penetrated me. The morning after, we had sex a few more times, but still nothing. He was normal-sized in my opinion (though I’ve never seen another penis). I have used a dildo, so I know what penetration feels like. Can my vagina get drunk?
—Chelsea, Midtown

I like to imagine you and your vagina out on the town, just a couple of single gals throwing back some tequila. Both men and women’s sex bits can be desensitized by alcohol, but not feeling anything at all is a different matter. I’d point you toward porn to do some penis-size comparisons, but many of those supersized examples are the exception rather than the rule. He could have a very small dick! It happens. I’d advise you to get out there and have more sex. Hopefully you’ll feel a lot more full the next time around. If not, consult your gynecologist.

My girlfriend and I have been doing the long-distance thing for 10 months. I love her, but she’s very distant lately. She seems not to care when I’m visiting next and never says “I love you” first, and during our last weeklong visit, we only had sex twice. When I try to talk to her, she gets frustrated and says everything is fine. What’s going on?
—Tim, Upper West Side

I have some tough news for you, Tim: You’re headed to Dumpsville. Your girlfriend may be going through something that has nothing to do with you, or she may be getting ready to end things. But if she won’t talk to you about what’s going on, there’s nothing you can do about that. You should feel loved and wanted in this relationship, and if you feel you’ve already done what you can to mend things, it may be best for you to get out. At this rate, she may beat you to it.

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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.

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By: Jillian Anthony

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