This was way too long pre-editing. Let me try again.
Basically, I have been seeing a girl for almost 4 years, and we started being intimate after the first year. We were both virgins when we started dating, and even though we thought we'd hold off on sex, after a couple years of thoroughly enjoying "everything but," we decided to have sex. It was far more difficult than either of us had anticipated. I always found that using 2 fingers prior to that time caused her pain, and I just assumed this was because she was a virgin. However, after trying to have sex numerous times, I'm not sure what the problem is. I've never been able to fully penetrate her, and it took me months of repeated tries before I could even get in more than a couple inches. It seemed every new millimeter I entered her caused her excruciating pain, and I cannot be aroused when she's in such pain, so naturally, I go limp. We hardly even try sex anymore because it ruins the intimacy to have these repeated failed attempts. When we do try, I am now able to enter 3/4ths of the way, but that is the deepest I can go, and she's still in immense pain, so obviously I never get close to orgasm before going limp. I'm quite adept at giving her orgasms through other means, and I have tried penetrating right before an orgasm, and right after so there's more than adequate lubrication, (i also use store lube in addition.) We've tried numerous positions, from ones giving me all the control of entering, to ones giving her all the control, and ones that combine, but every time, if I even get to the point where i'm maybe 5 or so inches in, and can adequately thrust, the action dies down when I see she is not only Not enjoying it, but pretty much looks like she's hating it. It's gotten so bad that even though (Admirably) she still suggests we keep trying, despite how aroused I am prior, sometimes at the mere mention of sex, I get so uncomfortable at the idea of a repeat performance (which is not only embarrassing for me, but means that I will not get to have an orgasm at all that night) I go limp before even putting it in. I'm developing a phobia of her vagina. Has anybody had similar experiences? Is there anything else I can do? I try to make her as comfortable as possible, and be as romantic as possible, but nothing has worked in the past and it's extremely frustrating! Thanks in advance.