I had a bf once that wasn't that large but was wide you know and I always felt pain everytime. Regarding why she can't reach an orgarms it could be a number of things. Have you asked why that might be? She is the only one who can tell for sure

Well, when you're in a relationship for awhile (atleast for me), it gets harder to become aroused, and you don't get as wet as fast. My husband needs to do more foreplay now (he's very big btw =o). Maybe that's the problem? She's not wet enough at first, so the fact that you're lasting longer isn't good at all if she's in pain.

I've spoken to some other women with the same problem. This might not be the problem, but hey, more foreplay never hurts for us women >=)

Well, I think my boyfriends, well big. And after having sex over a year, I still hurt. I don't know why? Because you'd think i'd be used to it...But I guess i'm just not?