it hurt more than i could've imagined. however, every guy that had ever fingered me prior to me having sex each had commented on how abnormally tight i was compared to other girls, and regular-sized tampons were always uncomfortable. there was no blood! but i am an extremely active person, and throughout high school i played volleyball, soccer, and swim year round, so that may have been the reason why. yes, he knew it was my first time. he was 4 years older, so obviously he was not a virgin. he had lost it at 17. he was really sweet about it though! we dated for 4 1/2 months before having sex. "making love" as he calls it haha. he freaked out about making positively sure that i was ready. he didn't want to hurt me and hated it that i was in so much pain, so i guess that was cute, in an odd sort of way! i left for europe the day after we first did it, so the second time was 3 weeks later, and it hurt just like the first time! but about the 4th or 5th time it stopped hurting and started feeling amazingggg. oh and by the wayyy, i must be the luckiest girl alive, because through all the pain i still managed to orgasm twice my FIRST time. go me :D