I am a 26-year-old gay male and have masturbated ever since I was 12.

I have always masturbated at least 3 to 6 times a day – but when I am with my boyfriend it takes me a long time to reach orgasm, and my penis is not as sensitive as I think it should be. It is very much erect, though. Is it possible I have lost some penis sensitivity? If so, how can I regain it? I have tried not masturbating for 3 weeks and then having sex, but even then I'm still not that sensitive.

Penis sensitivity can vary somewhat from person to person, in both amount and location. On some people the glans (head) is the most sensitive part, for others the skin just behind it, and still for others the skin on the underside of the penis. It's unlikely you reduced your own sensitivity through masturbation, unless you frequently used some kind of violent technique, and as far as I know there's no real way to increase the sensitivity, either.

Actually, a lot of men would be envious of a penis that's less than hair-trigger sensitive. Some people even put mild topical anesthetics on their penis so they can last longer (athough it doesn't feel as good). Also, when two people get together, rarely are they equally sensitive and equally turned on by the same things – that's just stuff you have to learn about the specific person. I don't know if those things make you feel better, but they're worth considering.