I was, to the surprise of just about everyone, a late bloomer and didn't lose my virginity until I was 20--it was, sadly, also the first time I'd really been seriously kissed. I was a nerdy geek in high school; dated a little, but never long and never serious. Then I went to college, and I realized guys were actually interested in getting into my pants! Because my brain tends to sit out most of my conversations with people, I actually managed to gain a reputation as the campus slut before I'd had any form of sexual activity.
So I lost it at a party, in a run-down trailer rented by three male students. I was drunk along with everyone else, but fortunately the guy was one of my best friends. Unfortunately, neither one of us knew the other was a virgin, so we had no clue what were doing--theory without practice. It was our both oral experience, and it was probably a bad performance and experience on both our parts--I don't think he knew what he was supposed to be licking, and I don't think I knew how to cover my teeth very well.
I'd been agressive and on top for the foreplay, but since I had no clue how this worked, and that it was likely to hurt, I asked if he'd mind being on top and he agreed. Well, the alcohol didn't help--I think I was actually HOLDING a bottle of Jack Daniels at the time, which is always a great sign--but neither of us knew exactly how to fit Tab A into an elusive Hole B, and neither of us knew the other didn't know what they were doing anyway. He was having difficulty with the entry, naturally, he just didn't know why. He used his fingers to get started, and so the hymen was officially broken; but he either didn't notice the blood or thought I was having my period. I honestly think he just didn't notice. He said afterward, "Yeah, you were really getting into it when I was using my fingers;" 15 years or so later, we found each other online and I said "I hate to tell you this, but I was actually squirming around and making noise because it hurt like fucking hell." Some form of penetration was eventually achieved, but we didn't finish; first, he had trouble completing entry, basically because neither of us realized raising my knees and bending my legs would greatly facilitate the process. So yeah, as much as I hate to admit it, I was lying on my back like a clueless and drunk limp fish. It was less exciting than most celebrity sex videos--"Um, did anyone check to see if Paris is still breathing?" I didn't realize it, but apparently 6 of the other guys at the party went outside, stacked up a bunch of crap in front of the window and were trying to watch, though apparently they kept falling in a brilliant display of instant karma. My partner saw them, though, because he was facing the window and there were enough crashes and thuds coming from outside the window for him to look. He was nervous to begin with, obviously, but that kind of killed it for him. I didn't care, I was like "fuck it, let them watch," but he couldn't perform with an audience. So I guess I kind of lost it on a technicality, because penetration was achieved. I'd never used a vibe at that point, or even used tampons more than twice, so I had no idea how it was supposed to feel, and I honestly don't know how far he got before he lost it. Fortunately, we both think it's pretty funny to look back on the whole thing. So, in my official "number," I usually count him as 1/2, just because I don't know exactly what happened.
It definitely was a memorable experience, though, even if not in the traditional way.