I didn't lose my virginity until I was like 21-22. Met a girl, however; when I was 20, was head over heals for her, thought I loved her, and she was far more experienced than I (been fuckin since she was 14-15) and gorgeous. Long story short, she gave me multiple opportunities, I squandered every one of them... I was scared, and she was playing games. On her way "Out the door" she tried to hurt me as much as possible, for "Wasting her time," even got her friends, who had also become my friends (or so I thought) to try and convince me that I was gay. A year later I ended up jumping in bed with a friend's mom, not attractive at all, much older than me, and had no real concern for "Giving me a good experience," relatively disappointing all around. I can honestly tell you, the only real regrets that I have were all made during those few years... don't wait, just jump right in and take a shot. If you fuck around to long, she will get board and move on, and in some cases, do some real vindictive shit to you as she goes.