The fact is that the first time shouldn't hurt. It'll obviously be a bit bizarre and uncomfortable at first - but most of blood that comes from sex is due to tearing of the vaginal walls, much less the hymen. Vaginal walls are obviously not supposed to be torn, and it's a sign that the woman is nervous and perhaps apprehensive. That can be a result of not enough foreplay to really relax her, going too vigorously and the pervading myth that the first time is supposed to be agonising. Maybe if girls weren't told that it's supposed to hurt the first time, they'd relax a bit more.
Your use of "break in" doesn't do much to dispel that myth, I mean, ****, would being a bit more considerate and in-touch with your emotions hurt? Disgusting.