The Hook Up: Orgasm difficulties and shifting identities


I’ve recently started having regular casual sex with someone but have an extremely hard time reaching orgasm, which is not for her lack of trying and generally doing a good job. She gets me to the edge frequently but isn’t quite able to push me over it. I’ve only had sex with one person before this and had the same problem then. Although my partner is understanding, I find it really frustrating and embarrassing. Usually after a long bout of trying, I just ask if it’s OK for me to do it and let her finish me off (which she’s been very good about but I still feel rude given all her efforts).

This leads me to the second part of the problem: I have no problem hitting the “O” when masturbating. It’s something I’ve been doing regularly for a few years and can come quite easily and quickly. I’m worried I’ve actually conditioned myself to come in a very specific way and having someone else touch me feels so different that my body doesn’t know how to react. Do you think this is the case, and if there’s any way to change it? I don’t think it’s the lack of a clear mind and although I can come using a vibrator, I don’t want to become reliant on it. I tell her what I like and she acts accordingly, but it still feels different than what my body is used to. Help?—Frustrated

Anna says: I don’t know if this will ease your mind any, but what you’re experiencing is incredibly common. Oodles of women can’t come at all, let alone with a partner or while masturbating. Feel better? Now that that’s settled, let’s go watch Doctor Who.

Just kidding. I can talk about your vagina all day. The most likely (and likely most frustrating) answer is you just need to give it time. And give yourself a break. The anxiety and embarrassing feelings are only going to make it harder for you to orgasm. Be confident in the knowledge that sometimes it takes a while for our bodies to get used to new people, new hands, new toys, and new conditions. And seriously, that is totally normal and fine. I also admire your perseverance and willingness to adapt. You know what works for you and you communicated that even though it was hard. If I was your therapist, I would give you a big gold star because I actually wish therapists were validating in a fourth grade teacher kind of way.

So. Yes. Other reasons your head may be working against your body might have to do with aforementioned guilt or anxiety, which is terrible because, like, don’t we have enough to worry about? But while getting it on, there comes a point where we start to wonder, “Am I taking too long? Is she bored? Does she hate my belly button goatee tuft?” And thus starts the downward cycle of negativity. I know it’s hard, but try not to get down on yourself in the moment. Focusing on the “O” may actually make it more difficult to attain. Sometimes what works for me is to think of myself as a dude. Dudes don’t “feel bad” for taking a long time. If anything, they are praised for their stamina and ability to last. When I reframe my own thinking, sometimes it gets me out of the self-loathing funk. Plus, genderf*ckery is hot to me, so that works out too.

It’s possible that your masturbation habits have conditioned you somewhat. But you’re already working on that with your partner by incorporating her into your solo-stimulation habits. Two gold stars! You can try to vary your routine, either alone or with her, if you’re worried about becoming a one-trick pony. A vibrator won’t desensitize you, however. Not for more than a few minutes, anyway. Also, many people incorporate vibrators into their sex lives regularly. So if you prefer to get off using one, then by all means, go to town. Don’t let other people’s expectations or the Sex Police try and stop you. It’s your party and you can get as buzzed as you want, if you’ll allow me to mix a metaphor.

Really though. I think you’ll be aces in just a few weeks of consistent sex with this person. It’s probably a mental block. Keep doing what you’re doing, don’t be afraid to try new things, and enjoy whatever it is that gets you off. “If you can’t beat ‘em, beat it,” as the old saying goes.