Sex Column: Taking Care of Business

Dear Tippy,

I have rather the opposite problem of Mrs. Penis Problems’s boyfriend. Instead of reaching orgasm too soon, I fail to reach orgasm at all. Seriously. I’ve been sexually active for the past three years and have never had an orgasm while with a partner. I can cum through masturbation, but when I’m with someone else it just doesn’t happen. This isn’t a debilitating problem: I stay hard and have never had trouble bringing my partners to completion (or completions). However, it’s embarrassing for both parties when I have to reassure a hook-up that the reason nothing is happening isn’t her or something she is doing. It is also, as you can imagine, pretty frustrating to end up with a case of blue balls after a whole night of otherwise fantastic sex. Do you have any advice?

Best Regards,

Mr. Cold Showers

Dear Mr. Cold Showers,

Wow this is a hard one! (Obligatory Tippy Maple bad sex pun.) But really, it is. Although I do feel sad for you, let me first reassure you that of all the sex problems you could have, this is one of the better ones. I know you are frustrated, and your hook-ups may be insecure they are doing something wrong, but from a lady’s perspective, I can tell you: It’s a lot more fun to be with a man who knows how to keep his cannonball in the cannon than to be with the all-too-common early cummer.

But now on to some more substantial advice. A good first place to start is to stop masturbating, or at the very least reduce how frequently you masturbate. Too much masturbation (yes, I know, it turns out such a thing is possible!) can make the penis insensitive during sex, which could be contributing to the problem. Additionally, you may have inadvertently taught your body to be able to orgasm only during masturbation. If you hold off for long enough, you should be so horny and ready to lighten your load that sex will be a relief!

Next, make sure you don’t forget about good ol’ foreplay. Just like for female-bodied people who have a hard time reaching orgasm, lots of foreplay is key. If your partner gets good at going downtown, maybe that can become a new way for you to deliver. Another option could be to try to have partners jack you off, even though often this won’t be as satisfying as masturbation. In fairness to us ladies, we don’t have any appendages to practice on, but seeing as handjobs seem to be your go-to, it might be worth a shot in your case. Also, don’t discount finishing yourself off when you feel close to cumming. I’ve had many partners take care of themselves when they were about to finish; going the DIY route isn’t at all unusual or embarrassing and might be a good first step to combining sex with orgasms.

In addition to all this, you might want to try “tight” positions, i.e., positions in which your schlong is especially snug. I’d recommend trying a variation of the missionary where your partner puts her legs on your shoulders and you push them together. Another cozy favorite has the woman lying down with her legs close together and the man on top.

And a last word of advice: Paradoxical as it may seem, don’t focus too much on orgasming. Just have fun without any specific goal in mind. You are probably psyching yourself out by fixating on the elusive orgasm. And when you stop worrying, it’ll cum when you’re least expecting it. (Sorry, I’ve used that pun before, but it’s too true not to use again!)

Wishing you all a great spring break and even greater sex!

Happily Horny,

Tippy Maple

P.S. Questions, concerns, positions to try? Submit your answer anonymously to

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