Re: poping the cherry
It really depends on the girl. Some only have a small hole in their hymen when they first have sex, so more of it tears (thus, it hurts more). But some already tear almost completely from other activity (such as masturbating by inserting objects into the vagina) so not much else is damaged when they first have sex (i.e. won't hurt as much). If you masturbate regularly, and if you're used to inserting things into your vagina, it shouldn't hurt very much at all, if not only giving you mild discomfort.