 I had sex for the first time when I was with my ex-boyfriend. I didn't bleed then and right now I'm in a new relationship. I and my current boyfriend had sex a few days back and it hurt more and I bled. As I was already sexually active in my past, how is it possible to even bleed after I have already been sexually active? Yes, women tend to bleed during sex for various reasons. It's not always that when you have sex for the very first time or when you lose your virginity, it's only then that you bleed. You can bleed anytime afterwards, the second time or the third time and also whenever the guy hits you the wrong way inside or his penis is larger and your vagina is unable to accommodate it. You tend to have small micro abrasions or tears which bleed afterwards but if it is happening again and again then it can be an indication of disease. So for that you should go to your doctor, get yourself examined just to find out that everything is okay.