Heather Corinna replies:
Me and my girlfriend were both virgins and just had a go at intercourse for the first time. Unfortunately, her vagina is really tight and is pulling the foreskin on my penis back causing pain for me and also for her. I've fingered her a few times to help loosen it up, and wore a condom to help with the lubrication, but it's just really painful. Is there something wrong with my penis, or just too much wanking?
None of this has anything to do with how much you masturbate. Nor is this likely about something that's wrong with your penis.
I am, however, seeing a few issues here that are either misinformed or not as they should be which are the likely culprits.
For starters, understand that the vagina really can't be permanently tight, loose or loosened. When a woman is not sexually aroused, the vagina -- a tubular muscle -- is a closed tube, whose walls lay flat against each other, and whose opening is relatively small. But when a woman becomes sexually aroused, both her vaginal opening and her vagina both self-lubricate and loosen. When she is no longer aroused, they both go back to that collapsed state. Even the vaginas of most women who give birth -- and an infant is far larger than fingers or penis -- will in fairly short order move back to being nearly the same as they were before birth and pregnancy.
So, you can't ultimately "loosen" your girlfriend's vagina by inserting fingers in there, save in any one instance of doing so before intercourse IF that is something she finds very sexually gratifying and exciting and IF she is becoming more and more aroused when you're doing that. And if all you're doing is sticking fingers in, chances are good that that isn't very gratifying for her all by itself. For a majority of women, while manual sex that's about fingers being inside the vagina may ALSO feel good, without paying attention to her whole body, and to the area of her genitals that has the most sensation (the vagina doesn't have very much), her clitoris, it's not going to feel very nice all by itself. same goes for intercourse all by itself: that doesn't often feel so hot to most women, either, so do be sure you're both engaging in a variety of sexual activities, some of them before intercourse, every time.
Too, you say you're using condoms to help with lubrication, but condoms actually increase the need for EXTRA lubrication. So, when using condoms -- as you should, and it's fantastic that you are -- you need to also get some extra latex-safe lubricant to use WITH those condoms. You'll want to put a couple drops in the tip before you put it on, then after it's on, rub the condom, her vulva, or both with more of the lube. If things get drier down there during sex, you just add a couple drops more as need be.
Bear in mind that some big things that inhibit arousal -- that keep it from happening or increasing, especially with women, but with men, as well -- are nervousness, fear, any feelings of performance pressure or anxiety, worry about not doing things right, and by all means, pain or anticipation of pain. That's one reason why it can be pretty common for intercourse to be painful for women the first few times, beyond any physical issues, because they are so fearful, so nervous, and so concerned they WILL feel pain. And when a woman is very nervous or fearful, the vagina and opening can actually sort of clamp down reflexively. So, if she's not really ready, not really able to relax, and not really feeling okay about sex, that's not only one reason this can be happening, it's also a reason to take a few steps back and hold off on this until she isn't feeling that way. It might be worth having a talk together to make sure you really are both on the same page in terms of your readiness, just in case.
I'm going to load you up with a handful of articles that should round all of this out for you so that you can see more of the big picture, and have a better idea of what the most likely problems here were. They should help make things go a lot better for you both, not just the next time you attempt intercourse, but in terms of your understanding of each other's bodies and your sexual relationship in general.