text: i reacently started having sex i know it's supposed to hurt the first 2 0r 3 times? is it still supposed to be hurting after  8 or more times i don't have any std's or anything and im not dry so what could be the problem please help anyone else have or had this problem????????????? it can hurt the first couple of times if your partner has a good size ****. but it will stop hurting after you get use to it. but you should relax and take your time, don't rush in this sex thing. but if you do start to have it on the regular bases then you will become more use to it and then you can in joy it without it hurting you. hope this helps.