it is almost always going to hurt a girl/woman the first time she has sex. the most shes probably used to is a tampon, so go nice and slow. if you have doubts that she wouldnt like that, then ask her how you want her to do it. chris is right, she may still be a virgin and when you get ahold of her she wont bleed. i'd had sex with 4 different guys before my hymen broke, which happened to be when my boyfriend (who i had been having sex with) was fingering me. and there was a puddle of blood. but it all depends on the girl and her body. just remember, be nice. you dont want to scare her into never having sex again fora long time, and you want to treat her right...if you tell her to just lay there and dont move or talk ill go to whereever you live and cut your penis off. that still bothers me that one dick said that to the girl, no wonder she doesnt know what to do (oops) -Steph (i guess thats what i get for using my boyfriends computer.)