I agree, I LOVE anal, but only when I'm turned on. Did you "prep" her before trying to penetrate with your penis? When my b/f and I do it, we usually have regular sex for a little bit, or oral, while he also fingers me "down there" to get me ready for the actual sex. We have tried it without doing that, but then it hurts me. Also, make sure you use LOTS of lube at first. I don't really need him to slather it on any more, but it really helped alot when I was just getting used to it to use alot of it. Also, I think her mental state has alot to do with it too, when we first started with it, I would be nervous about it and I think that in turn made me tense up and made it hurt. Make sure she really does want it before you try. Also, I'm not saying for her to get drunk, by any means, but I found that just a drink or two would loosen my inhibitions a bit and made me more relaxed. Good luck...I never thought I would like it as much as I do now!