I have a semi-serious concern - semi not because I just think it's unimportant, but because there's still plenty of time on the clock and even then other ways to please someone. But first, I have to do a quick history catchup: I'm 19, my girlfriend is 20. I became friends with her four years ago, began dating her a year after that, and she had to move a year after that (two years ago). She'd been holding back from college, hoping we could go together - and we both got into University of Texas in Austin, lucky us, so we will be together, and I imagine things will get intimate. The problem? We kept dating long-distance (anyone else with experience on this knows how much this sucks), and we've shared some personal information, particularly our lower body "sizes." I'm 7-7.5"/5", and she claimed she can only fit two fingers inside of her. Not she masturbates with two - she can only fit two in. Furthermore she's rather small - a few inches over 5 foot. Oh yes, and we're both virgins - we'd been saving it for each other. As such, I don't have any real experience. As for actual penetration, I've lurked around - lot of foreplay, lube, etc. My problem is this, though: I've read that the first time tends to hurt for a lot of women, and that's just regularly - but not always. I want to make sure that it doesn't hurt for her - at least, not the first time. She's admitted to fantasies about rough sex, but I want to be sure she can always remember the first time as something romantic and magical and all that jazz. I'm willing to do just about anything - just foreplay and tongueplay for a few weeks, steady stretching with gradually larger toys, whatever - as long as she isn't hurt in the process or hurt when I actually give her that special night.