I lost my virginity a few months ago to my boyfriend, and everything was going fine until it wasn't. We're still in high school, so any sexing that happens is very rare, an awkward situation with the parents (who are somewhat okay with it but aren't thrilled), and kind of unpleasant. To begin with, it hurts for me. We've had sex five times and it's gotten a little better since the first time but it still hurts an insane amount when he's entering me. We use condoms but have no way of getting lube, and try to wait until I'm ready but because we want to do it before the parents get home I'm usually not relaxed and wet enough when we start. Sex also just doesn't feel good for me. It's kind of nice for maybe five minutes (after the initial pain of penetration is gone) and then it just starts feeling numb and I've never been anywhere near an orgasm. It ends up feeling bad for me because it hurts like hell, doesn't feel good at all, and it's impossible for me to relax because I'm worrying about my parents getting home. I also feel like my boyfriend and I share unequal parts of the responsibility/results of sex, because it hurts and doesn't feel good for me, when I was on the Pill I had to ask my mom for refills and deal with how awful being on the Pill was, and deal with my parents knowing that we had just been having sex when they would get home (which is awkward and unpleasant, not to mention me feeling bad about losing my virginity at 16) and for him it was a lot better (because his parents don't know that we have sex and because he does get off from it). I know I'm still young and that this isn't the end of my sexual experience, but I'm starting to feel really opposed to sex because of how bad my few experiences have been and I don't know what to do to not have such negative feelings about something I really want to enjoy doing. Does anybody have any suggestions about this?
Also, my boyfriend has been unable to give me an orgasm since January. We're tried intercourse, manual stimulation (both clitoral and penetrative), and oral sex, and nothing works. I've told him specifically where and how to touch me, but usually it doesn't feel good at all or if it does, the feeling quickly goes away. I am able to come when I'm by myself (and have masturbated successfully in front of him), but I don't like masturbating and am becoming frustrated and a little embarrassed by this issue. We've had no trouble with this in the past. Again, does anybody have any suggestions about this?