I'm a 27-year-old straight female in a truly wonderful relationship. We've been together for just over a year and living together for four months. Things between us could not be better. We have sex 2-4 times a week and usually it's incredible for both us. We're not afraid to try new things with each other (toys, mild restraints, etc.) and are genuinely very attracted to each other. The obvious BUT here is an issue that has been happening since we first started dating, and that my boyfriend says has been happening to him his entire sexual life. About once or twice a month, he can't finish. He can always get hard, always stays hard, but will eventually just throw in the towel and tell me it's not going to happen. If we try to push it and keep going, it gets increasingly sensitive and painful for him.

We are already careful about not drinking before sex and have only ever been able to have sex once in a day and I am 100% confident he's not cheating. But I had a bit of an epiphany the other day, and realized that while he's certainly no prude when it comes to DOING a wide variety of sex acts and has no problems with affection, even publicly (to an appropriate degree), he gets as uncomfortable as a teenage boy when it comes to TALKING about it. Like physically uncomfortable, giddy, silly, absolutely hates to say or hear anything overtly sexual (other than, "hey, let's have sex now"). Even if its to tell me what he likes in bed, even though I have never once been judgmental about or turned off by something he wants to try. I'm thinking that maybe this is somehow connected to the occasional non-finishers—despite being reasonably GGG in the moment, he's uptight about talking about sex.

He says he's willing to take baby steps with me to get more comfortable with it because I think it will help. Mostly starting with brief, lighthearted conversations about things he likes, directed and led by me (he finds it "weird" and "strange" that I've had conversations like this with past partners). But I don't want to push him into doing something that makes him uncomfortable if it has nothing to do with the problem I actually care about.

Do you think his sexual uptightness occasionally causes him to not be able to finish, despite being able to stay hard? If not, what else could it be? He says it's common, but I've never had it happen this frequently in past relationships. It's definitely happening more often than I'd like it to. Thoughts?

Wanting A Finish

My response after the jump...

If your boyfriend could fake orgasms and get away with it—if he could do what many orgasmic-but-not-every-time women with insecure boyfriends do—he'd be faking orgasms to get you off his back. But guys can't fake orgasms as easily* so there's no escape for him.

Look, WAF, difficulties talking about sex are common and your efforts to draw your boyfriend out of his shell are praiseworthy. But you're doing it for the wrong reason. Getting him comfortable talking about sex is not going to result in him climaxing each and every time you have sex. Because your boyfriend's shyness isn't the problem, WAF, and his inability to climax every time isn't the problem.

You are.

This is the way his dick works, this is the way his dick has always worked, and you need to accept that this is the way his dick works. Stop pathologizing his dick. Some guys, like some women, can reach a state of overstimulation that leaves them incapable of climaxing. It doesn't mean the sex was a waste of time, it doesn't mean they didn't enjoy it, and it certainly doesn't mean they're drunk or beating off too much or cheating or somehow having their orgasms chased off by uptightness. All it means, in your boyfriend's case, is that once or twice a month he can't finish. Period.

His dick can't be fixed because there's nothing wrong with it. Accept his dick, enjoy the sex, continue to help him get more comfortable talking about sex, but stop regarding his inability to come each and every time as a Problem That Must Be Solved. You should regard it as a perk: you're one of the very few straight ladies out there whose male partner doesn't regard his orgasm as the only reason to have sex.

* But some guys do, ladies, some guys do.