Sex Column: The Sex Improvement Project

Dear Tippy,

My boyfriend is uncircumcised and therefore super sensitive. It’s hard for me to relax and let go of worries/insecurities because I am constantly on the alert for a request to change speed or switch positions in order to prolong sex. There is no happy time medium: We either go for a measly 30 seconds or an awkwardly prolonged 45 minutes (typically without orgasm for either party in the latter situation). We’ve been dating for over a year, and the problem is getting worse. I used to enjoy sex, but it’s starting to feel like a chore. Advice is appreciated—thanks!


Mrs. Penis Problems

Dear Mrs. Penis Problems,

It seems that you’re in quite a sticky situation (sorry for the bad pun). The good news here is that the extra sensitivity of an uncircumcised penis can ultimately lead to your boyfriend’s having more intense orgasms and to better sex for both of you. However, it will require some extra work for you and your boyfriend to cum to this happy place (sorry for bad pun number two).

Regardless of however you and your boyfriend eventually solve this problem, a necessary first step is to have an open, honest conversation about both of your wants and needs. He’s probably aware that the sex is less than ideal, and if things haven’t solved themselves by this point in your relationship, then, as Salt-N-Pepa say, some “Let’s Talk About Sex” is in order.

It’s hard to give specific advice without knowing all the details of your sex life, but from what you’ve written, I might hazard a guess that at least his orgasming quickly isn’t necessarily related to his uncircumcision (I’ve unfortunately been with all too many circumcised men who finish quicker than Usain Bolt can run 100 meters). If he’s willing to put in the effort, he can learn how to last longer. One way he can do this is by focusing on something besides orgasming while you’re having sex. Another way to learn is through masturbation: If he practices lasting a little longer every time he masturbates, eventually this will pay off in the bedroom. He also can try pausing during sex, right when he gets close to orgasm, which will allow him to contain his excitement a little longer.

And now, on to the more “touchy” subject of his sensitive penis. Start off by discussing positions that each of you like best, and, hopefully, coming to some kind of compromise in positions to try. In my experience with uncircumcised men, some good go-to positions have been spooning, missionary, and woman-on-her-stomach-with-guy-lying-on-top-going-from-behind. All of these positions allow your boyfriend to have a little more control of the speed and angle of his penis, so he can avoid painful positions.

And don’t forget about good ol’ cunnilingus. It may take a while for your boyfriend to be able to last longer, but that doesn’t mean your orgasms should go by the wayside in the process. If he gives you oral sex until you orgasm or until you get close and then does his 30-second routine, this leaves both of you the merrier. During sex, he could try pulling out when he feels close to orgasm and then going down on you to catch you up to speed before he goes in again.

As corny as this sounds, the key to solving the complications of your sex life is open communication. Make sure you let go of all your insecurities and doubts because it’s pretty hard to have a good orgasm if you’re too busy worrying about what you think you’re doing wrong. More likely than not your boyfriend is experiencing his own insecurities, complicating your sex even further. You two should talk, dispel all insecurities, and keep practicing so that, pretty soon, penis problems will be gone!

Happily Horny,

Tippy Maple

Winners of last week’s contest for kinkiest/strangest bedroom experiences:

1. Pleasuring a partner using feet

2. Masturbation races

3. Nutella blow jobs

Next week’s question: What advice do you wish you had given your ex that would have improved sex? Submit your answers and all other questions you have anonymously at

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