You're not a silly teenager fool.

I was 18 the first time I had sex, and I had been with the guy for about six months. I did regret it after - we wound up breaking up very shortly after that.

But now that I'm 22, I don't really regret it as much as I did then. And hindsight being what it is, I really don't think I should have waited. At the time, it was the right thing to do. And I learned things from it. And all we can do is make the best decisions based on the information we have. And now, four years later, I'm back together with the dude.

I think my recommendation would be to talk to him openly about how conflicted you feel. I wasn't really open with my guy at first, and that did make the experience more unsettling for me. But maybe if he knows how you're feeling, he can help you with that, or won't, and it'll make your decision more clear. Especially since you guys are good friends.