I'm seventeen years old, and recently started dating this guy named Mike. He's twenty, and he's done loads of stuff. Has had plenty of sex, knows his way around a womans body, if you know what I mean. I've been thinking about having sex with him, but thing is, I'm a virgin. I'm a little scared of how painful it will be.
We've actually tried-once on St. Patrick's Day, and once again last night. St. Patty's day, though, I was a little drunk and so was he. When we tried, he had a condom on (he always practices safe sex), and we tried almost for two hours to get it in. It went in a little, but it hurt so much, that we had to stop.
I recently told my friends about this, and one of them recommended not doing it on the bed. She said missionary style makes first times worse.
So my question is, is there any way to do this in a position with the least pain possible? Also, is there anyway to relax myself without the need of alcohol or drugs? Because I've been thinking about getting drunk and trying it...