my first time, I was with a good friend of mine. We had dated a few years before, but that didn't work. We became great friends later, and partied/drank alot together. I kissed her one of those times, and it was pretty nice, but we didn't want to date each other. The next party (always at my house), we talked about having an 'arrangement' - we'd just have sex whenever we wanted, while we were single. So that's what we did. Both of our first times, we were drunk at a party and had confused sex. Kinda sucked. but we tried if a bunch more times and got better
THen emotions kicked in, and a few months later she had her friend call me and say that she was pregnant. I didn't find out that she wasn't until a week later, by which point I had thoroughly freaked out. I didn't talk to her for about 6 months, then we made up and are great friends to this day!
still don't regret it.