My boyfriend has a lot of trouble achieving an orgasm, especially with a condom. He's very good at getting me off, and he usually does so multiple times, but sometimes he can go for hours and not get anywhere himself. Then we just stop because he's tired. He's been able to do it twice, both times without a condom. I'm on birth control pills, so I'm not overly worried, but I like condoms and find some of them quite sexy. We're both 23 and he was a virgin until me. Do you have some advice to help him? He's very sweet, and I would like him to feel as good as he makes me feel.

Since he was a virgin, then the likelihood if him having an STD is pretty slight (though not impossible if he ever had oral or anal sex before) so it seems the two of you don’t need condoms. Therefore why don’t you stop using them and see what happens. He was probably nervous the first time you had sex together, and that prevented him from having an orgasm, and since then he’s been worried about it, which is having the same effect. As long as he can have an orgasm when masturbating, it means this is not a big problem. He just has to learn to relax and push those worries out of his mind. If not using a condom isn’t enough, then have him concentrate on an erotic fantasy while having intercourse. That should help him keep negative thoughts from stopping him from having an orgasm.