Dear Sophie,

I rarely have an orgasm during any sort of sexual activity, not for lack of trying. The few times I have had an orgasm it has been through clitoral stimulation, but often even clitoral stimulation does nothing for me! Help?

Forget about it. Really, forget about it. Until you’ve figured out how to reliably have orgasms, you can’t go into any kind of sexual activity with orgasm as your goal. Instead, replace it with a new goal: feeling good and enjoying yourself. Relax.

Make sure that the person you’re with (this person is now a female so I don’t have to slog through pronoun hell) takes her time. Have her touch your inner thighs and lower stomach first. Hell, start even farther away than that if you want. Have her talk to you about your fantasies. Once you’ve really built up the anticipation, have her try the ol’ clitoral stimulation again. There’s no shame in using lube if you need it. Tense up your vaginal muscles—it increases blood flow to the area. Go slow, and just keep trying until it happens. Good luck.

Dear Sophie,

I have trouble orgasming during sex; sometimes I can’t finish at all. We wind up  doing it until I’m exhausted, or until she’s too sore to continue. I love my girlfriend and think she’s the hottest thing since earth’s molten core. What’s wrong with me?

I’m just gonna go ahead and ask you this question straight up: are you a chronic masturbator? I’m not asking this question merely for my own edification; a lot of guys get so used to orgasming from masturbation that other kinds of stimulation no longer work. If that’s the case, try masturbating less frequently and get used to using a lighter grip. If you’ve been using the “death grip,” it’s going to be hard to come from anything less than that. (Like a vagina.)

If that’s not the problem, there’s also the possibility that it could be psychological. Is your relationship with your girlfriend a new one? Could it be that you’re so attracted to her that it makes you anxious and ends up working against you? Talk to her, and let her help take some of the pressure off of you. Try getting naked and messing around without going for an orgasm. Remember that the two of you have a lot of chemistry and that you care about each other.

If that doesn’t seem right either, it could be that it’s a medical issue (for example, some medications can delay or prevent orgasm), and it might be worth talking to a doctor, just to check. But whatever the problem is, nothing is wrong with you. You’re going to be okay.

Dear Sophie,

I find that I don’t last very long during sex. I have tried different things to distract myself or make it easier to go for longer, but so far nothing has worked. I make sure to take care of my partner, but I think she would like more. Suggestions?

My friend, it’s difficult for me to give you new ideas when all you’ve told me is that you’ve “tried different things,” but I live to serve. Take that as you will.

Here’s a simple initial technique: when you find yourself right on the brink of orgasm, stop moving. Tell her not to move. STOP. Wait a minute and don’t move until the feeling subsides. (Don’t, by any means, start again right away, otherwise you’ll come anyway and it won’t be satisfying at all.) Once you get good at that, you can start trying to keep your orgasm at bay. That is, when you start to feel that one is on its way, slow down and move at a pace that’s pleasurable but won’t bring you over the finish line. This pace might not always be the same, so you’ll have to play it by ear.

Also, you should try to find a position that feels good but makes it difficult for you to orgasm. That means you’ll have to experiment to see what works for you personally, but I’d suggest something where you’re standing up, since a lot of guys have trouble coming that way. She can be lying face-up on the bed with you holding her legs, or bent forward over something. If those don’t work, find something that does!

Got a problem of your own? Tell me about it at my Formspring.

Sophie Kaner can be reached a [email protected].