I lost my virginity at 14 to my first boyfriend, a week or two after we had technically split up, owing partly to both of our parents bitching about the age difference (he was a month away from turning 18.) We had fooled around a little while we were dating, but I didn't actually get the courage to give him a blowjob until the night we split up and decided just to be friends with benefits. The relationship itself was pretty casual to begin with, no serious feelings, just mutual attraction. I went to hang out with him one day over the Thanksgiving break, we started fooling around, and we ended up having sex. Anal sex, actually. He was a bit nervous about breaking-my-hymen-taki ng-my-virginity (although it was probably broken years before) or possibly getting me pregnant, due to the age difference, and loved anal anyway. I had no objections to anal, and did it gladly. It actually felt pretty good. Then we went bowling with friends, haha. The really funny part is it was the first time I went bowling, too. We hooked up off and on for a few months, but we didn't have vaginal sex for the first few times. When we did, it didn't hurt but it didn't feel great either, and the only regret I have about that 'first time' is not getting on top when he suggested it, haha. I wasn't sure what I should do if I did, so we stuck to positions where he was in control.
The biggest reason for me not regretting losing my virginity so young by having non-romantic anal sex with a guy I had no real feelings for is this - a few months later I wound up in a sexual relationship with a good male friend (also almost 18) and his girlfriend, who I had known in jr high but hadn't seen in a couple years, which was amazing and taught me so much about what I enjoy sexually. This probably wouldn't have happened if I were a virgin, it started off as another friends with benefits situation, he liked me and his girlfriend (they were semi-long distance at the time) did too, so she approved of him being with me even when she wasn't there. He didn't want to take my virginity in a situation like that. The two of them are still together, and we are still really good friends. Hell, they drove 9+ hours on a whim so he could hang out with me one night when my ex was working overnight and he knew I would be alone and bored all night. Never got a better surprise than him calling me after I got off work asking which apartment was mine, because he was outside and it was cold.