I am a virgin as I've never had intercourse with a man or woman. I have started to masterbate with brush handles,etc. I was curious that if I had sex with a guy if it would hurt the same or not? I can go pretty far in sorry I know that's a TMI but I was just curious. I'm thinking about losing my virginity but am experimenrenting first before I do anything. It doesn't hurt at all to masturbate with anything it did a little at first but not anymore.