I know EXACTLY how your girlfriend feels. I was a virgin the first time I had sex with my boyfriend, and luckily, he was experienced, so it wasn't too painful. But even after the first time, it actually hurt MORE. We tried having me on top, but because he's very well-endowed (10-11 inches), that hurt a lot, too. Personally, I'd suggest going down on her for a while, since you both enjoy it, and fingering her too to loosen her up a little more. Try doggystyle, too - when my boyfriend and I tried that, I found that my muscles were a lot more relaxed. Also, make sure that you're only putting in a little at a time so she can get used to it gradually. And I'll give you the same advice I was giving - make sure she's totally comfortable, because if she's not at ease, her muscles will tense up and it'll be a lot more painful. Hope that helps. -=0)