I think the whole, "losing your virginity hurts like " is a bit silly. Perhaps it would if say your boyfriend has a rather large penis. And don't get me wrong, I'm sure there are plenty of women out there who might just have tight vaginas, or lose it at a young age, or whatever which may enhance the pain. But I personally think that alot of women get anxious, worried, even afraid of sex because they are in that mind-frame - but its not necessarily the case. Mind over matter, I say.
Anyway, I had to try a couple of times with my boyfriend to get it in properly, simply because it was a foreign... visitor? lol. I had a tiny bit of entrance pain, but then after that it was fine. No blood either. I think the thing about women bleeding on their first time is a bit silly too. Most women's hymens are broken during exercise or by inserting a tampon, generally not long after they've gone through puberty. Anyway, the sex was good because we both took it slow and he was really lovely about everything and made sure I was comfortable. Try not to pull any pained faces if it does hurt at all, lol, might scare him off. Just take it slow and make sure he's patient.
Good luck.