Dear Em & Lo, My Boyfriend Can't Give Me an Orgasm

Dear Em & Lo,

I have the opposite problem of last week’s advice seeker: My boyfriend is more than willing to go down on me, but I have a very hard time having an orgasm from it. I know it frustrates him that I don’t orgasm every time (or even most times). I have orgasmed from manual stimulation once or twice and a couple of times from oral sex. We are comfortable enough with each other that sometimes when he’s failed to bring me to orgasm, I’ve masturbated in front of him until I had an orgasm (which he enjoys). I know it’s easier for me to do it than it is for him because I’ve had a little more practice, but how can I help him? We are relatively comfortable talking about sexual issues, but we are usually both so frustrated by the end of the experience that we just want to go to sleep. He tries so hard that it makes me feel bad when it doesn’t happen. What should I do?

— Oh Oh Oh…No

Dear OOON,

It is sooooooo frustrating when you’re with a guy that you care for and are attracted to and want nothing more than to have an orgasm with, but it just never seems to happen. Unfortunately, many women find the ways they’re “supposed” to have an orgasm with a partner (during intercourse, or at least oral sex) don’t work for them. They internalize this cultural expectation which puts undue pressure on themselves, making it even harder to relax in the moment. And for most people, pressure is not an aphrodisiac. So they — and often their partners — try and try and try but to no avail and end up feeling like failures. Again, Frustrating with a capital F!

First, you’ve got to stop setting yourselves up for disappointment. Try to just enjoy sex without it being so goal-oriented. Sex doesn’t always have to end in orgasm for it to count; yes, orgasms are great, but making sure you’re both having a good time and experiencing pleasure is what really matters, orgasm or not.

Next, you’ve got to teach him exactly how you masturbate. Try to have him mimic the sensations and techniques to a tee. Be explicit about what goes where, pressure, pace, etc. Forget the idea that this somehow won’t constitute “real sex,” that’s it’s subpar because it involves his fingers rather than his penis or his mouth. Handwork is sex. Reject the notion that good sex should just come naturally, that it can’t be taught. Every woman’s body works differently, and some need more specific and precise stimulation than others — and that stimulation may not be intuitive for a guy to figure out on his own.

There are plenty more steps you can take to improve your chances of climaxing with him — you can read them here:

After employing all these techniques, let’s assume he’ll eventually master your particular masturbatory technique. Hooray! After a while, you’ll probably want to find a new way to climax with him. Great, go for it! Just remember to keep your expectations low. Don’t start this new quest to the exclusion of everything else. And consider the possibility that you may just have one way to climax with a guy and that’s okay. After all, when it comes to orgasms, the destination is more important than the route you use to get there.

Give us an O!
Em & Lo