So, for 18 months or so I was seeing this girl, and she was on birth control so we never bothered with condoms. She was also quite tight (which made sex pretty uncomfortable for her) and didn't produce much lubricant herself (often had to use the bottled stuff). During vigorous sex (the only kind she liked) I could rarely last more than a minute.
We broke up a few months ago and I've just recently started seeing someone else. She has a much better attitude and is more fun to fool around with, but she gets very wet, isn't so ridiculously tight, and we've been using condoms. So now I've got the total opposite problem where I'm struggling to achieve orgasm and even struggling to stay hard. We tried without the condom and it was a little bit better but still a chore. At least I have my "magic fingers" to compensate (she goes crazy for them, which is a nice ego boost) but it's still troubling/frustrating/a bit embarrassing.
Has anyone else gone through this? Did things get better when you "acclimatised" to her, or did you need help? I think the first thing I'm going to do is cut out masturbation entirely. Hopefully going a week without release will make things a bit more sensitive.
Masturbation makes you a lot less sensitive to intercourse and oral sex. If you stop, it should be fine.