How to Do It is Slate’s sex advice column. Have a question? Send it to Stoya and Rich here. It’s anonymous!
Dear How to Do It,
I’m a cis woman and am dating a really wonderful cis man. We started off casual and are now very serious, which is great! We love each other, understand each other, you know the drill. The catch?
He can rarely come during penetrative sex. We both really like sex, and really like it with each other, but…this just doesn’t happen for him. This didn’t happen early in our sexual relationship and has never happened to me before. He can finish during basically everything else (oral, hand stuff, etc.). He says I’m not doing anything wrong, and I know penetrative sex isn’t the end-all-be-all, but the person I love not being able to come inside of me is really upsetting! Do you have one simple trick I can pull out to suddenly fix this? Or is there some way we can sit down and figure this out instead of dissolving into a pile of mutual frustration?
—Sometimes I Just Want Some Boring Missionary
You can try delving into sexual details that really push his buttons. You can also try to consider what’s going on during the times he is able to come during penetration and lean into those specifics. Or zero in on what makes him orgasm during oral stimulation and handjobs and replicate those sensations during penetration.
You can also frame the experience of your partner coming inside of you as a joyous and rare occasion. Think of it as an unpredictable blue supermoon. Good luck.
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I’m in my late 30s. I’m still close with my childhood best friend I met when I was 10. We live in different states. Leading up to her divorce last year, we talked on the phone several days each week for about an hour each time. I was basically her sounding board and cheerleader. I thought her crisis would end after she and her kids settled into a post-divorce home and life. It didn’t. She still called regularly in distress, often over whatever guy she was dating, even if she’d only known him for a few weeks.