So, I'm a little on the big side but not enormous (7 long x 6.5 girth). My girlfriend wants to have sex, but the issue lies in the fact that it doesn't exactly... fit right. I don't think the issue is entirely me because I'm not ludicrously huge, but also that she's really tight as I'm the first guy she's ever been with. We've tried a few times now, but it just doesn't really fit well. We spend a lot of time beforehand trying to warm her up because she's scared of the pain and I'm scared of hurting her. The issue arises that somewhere between her being scared of it hurting, me being scared of hurting her, and spending so much time idly warming her up, I lose my hard-on a bit. By the time the condom's on and we're good to go, I've gone down to like 70% hard and have to try to do the whole "pinch the base, act like it's a cockring" kinda thing. I think most of my problem is nerves, and the nerves come from not wanting to hurt her. We've gotten far enough that I've popped her cherry, but she hurt like hell the next day and neither of us finished after that. So basically, my question is: Any tips on how to make it less painful for the woman or make it fit more comfortably?