Q: A two-part question:
Part 1: I’ve been dating my boyfriend for about a year, and I think we’ve both been pretty good, giving and game. That said, I’m still figuring out what works for my body — meaning, I’ve never had an orgasm. Maybe this is TMI, but his style is pretty fast and … poundy. Which is great sometimes, but I’d like some variation and subtlety, too. We’ve talked about it, and he’s making an effort, though I worry he’s not enjoying himself as much, won’t orgasm from trying it “my way,” or won’t be able to last as long as it takes me. He reassures me that he always enjoys himself, but it’s a difficult thing for me to disregard. Any tips?
Part 2: I had the thought that maybe his masturbation style has something to do with it. I don’t know how or how often he takes matters into his own hands, but if he’s not changing it up solo, maybe he’s used to a particular stimulation that would be necessary during sex, too. Do you think there’s anything to that? I don’t think it’s fair to ask him to stop masturbating, but I’m curious if there’s a correlation. Any tips for starting that conversation? I don’t want to sound accusatory.
A: Part 1: If you’re not orgasming during sex, then who cares if he doesn’t orgasm once in a while? Certainly not me, and both of you are gonna have to stop worrying about that in order to address something more important: your enjoyment, which will lead to your orgasm. I’m glad you’re already talking to your boyfriend about trying other things in bed; just starting that conversation is the second-hardest part. What’s the hardest part? Trying to stop worrying about whether or not he’s enjoying himself.
Even if he doesn’t orgasm every time, I promise you that he’s still having a good time. If he’s as “GGG” as you say he is — has Dan Savage trademarked that yet? — then he’s totally cool with doing things your way. He even said he’s all about switching things up for the sake of your enjoyment, right? Take his word for it! He wants you to enjoy yourself just as much as he does. The more you worry about his orgasm, the more preoccupied he’ll be that you’re not having one, the more expectations will be put on both of you, the more anxiety both of you will have about sex, and eventually it’s just too much pressure and you sit on the couch and watch “Game of Thrones” instead. You don’t want that.
Also, orgasming is not the end game. Sex is pleasurable no matter what as long as both you and your partner are into it. Do you know what you’re into, by the way? You should be taking matters into your own hands, sans boyfriend, when you have time. Find your own erogenous zones so you can show your man when he joins you. I’m pretty sure you’re 100 percent more likely to have your first orgasm while massaging your own clit than while having your vagina pounded like a piston.
Oh, and there’s no such thing as TMI. Not here in the Trust Tree, anyway.
Part 2: You’re probably onto something. How about asking him if you can sit in on the next session? Lie next to him, kiss him and give him the occasional hand. You’ll learn a lot about what he likes, and you’ll probably find it incredibly arousing as well. Mutual masturbation is a pretty awesome way for couples to discover (and rediscover) ways to get each other off. You might just find your big O that way, when you’re free to explore what feels good for you, knowing he is already having a good time.