Sexplain It: I Can’t Orgasm Without Jerking Off This Really Strange Way

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I’m Zachary Zane, a sex columnist and author of Boyslut: A Memoir and Manifesto. Over the years, I’ve had my fair share of sexual experiences, dating and sleeping with hundreds of people of all genders and orientations. In doing so, I’ve learned a thing or two about navigating issues in the bedroom (and many other places, TBH). I’m here to answer your most pressing sex questions with thorough, actionable advice that isn’t just “communicate with your partner” because you know that already. Ask me anything—literally, anything—and I will gladly Sexplain It.

To submit a question for a future column, fill out this form!


Dear Sexplain It,

I didn’t start masturbating the usual way, but I started doing what the internet calls ‘prone masturbation’ when I was younger. It’s great, and I can pleasure myself just fine, but I don’t think I can jerk myself off the “normal” way now. The problem is that this type of masturbation is harder to do with a partner, and penetrative sex just doesn’t feel as pleasurable. Also, it gives me performance anxiety during casual sex, because I don’t know how strangers will react to something like this. What do I do?

—Lying Low

sexplain it graphic


Dear Lying Low,

First things first, let’s define prone masturbation for readers who aren’t familiar: It’s when you masturbate face down on your chest and stomach. People who masturbate in the prone position often rub their penis against sheets, pillows, or clothing to climax. Or, they may cup their penis and testicles and thrust into their hand.

While there hasn’t been a ton of clinical research on the effects of prone masturbation, what does exist suggests that masturbating in a prone position can lead to sexual dysfunctions, including erectile dysfunction, delayed orgasm, or an inability to reach orgasm altogether. This is likely due to the increased amount of pressure and stimulation you put on your penis when masturbating this way. You don’t get this much pressure when receiving oral, having typical penetrative sex, or masturbating on your back.

The solution isn’t one you’re going to like: You have to stop masturbating like this. But first, I actually think you should stop masturbating altogether for a week or two. Give your body some time to reset.

After a couple of weeks, go ahead and start masturbating on your back while sitting upright on a chair. Will you struggle to stay hard and climax this way? Probably, and you may not be able to orgasm the first few weeks. That’s totally okay! Breathe, be patient, and don’t beat yourself up. (Also, check out these 16 tips to increase pleasure while masturbating.)

You’re going to be tempted to death grip your dick, to squeeze extra hard to mimic the pressure you received in the prone position. Don’t do that! You’re trying to retrain your brain to get to a place where it takes less pressure and stimulation to orgasm. White knuckling defeats the purpose.

With time, practice, and deep breaths, I do believe you’ll eventually reach a place where you can you’re able to maintain an erection and orgasm in “regular” masturbation positions. Only then should you go ahead and start having sex with people again. You’ll still likely have some anxiety—that’s normal. Pretty much every damn person has some anxiety surrounding sex. The ones who don’t have worked hard to overcome their anxiety; it didn’t happen by magic overnight. So you can always share with a new partner, “Just a heads up, sometimes I struggle to stay hard and orgasm. I just want to let you know that has nothing to do with how attractive I find you. I sometimes get a little in my head.”

Most people are open to hearing that and typically respond, “Don’t worry at all. I’m a little nervous, too.” (If they happen to react poorly, well then, that’s not someone you shouldn’t have sex with.)

Lying Low, I know this process may all sound daunting, but the calmer you are and the less pressure you put on yourself (and your dick), the more likely you’ll be able to solve this problem. If three months from now, you still can’t masturbate in a “regular” position, I’d go ahead and see a sex therapist. You’ll likely need to unpack and work through something deeper with a trained professional.

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