Okay, I'm going to break my promise to myself and say it.
I wish I could remember my first time, and what hurts me most about it is that I had ample opportunities thrown at me rather forcefully in high school, but I had promised myself that I wouldn't have sex until I could take care of the child that might, despite any precautions taken, result. I knew I didn't want to be placed in the position of using abortion as birth control (that was how I felt about the subject, when I was a teen), and so I passed on quite a few hot, bohemian, guys, including a pair of Swiss twins who had simultaneous crushes on me. So I ended up losing it to the first guy enterprising enough to help me fold my laundry and talk about Sir Gawain and the Green Knight, and when I coughed because the lint in the air made my throat dry and made it itch, he took a styrofoam cup from the stack that was always there in the dorm laundry room, filled it from the faucet that was there for hand-wash-only items, and gave it to me. I didn't watch him fill it. I had my back turned to the dryer. I was folding a shirt, a sweatshirt from my brother's alma mater that I had bought because I was proud of him. I turned around and took the water. I drank the whole thing in one gulp and he got me some more. That went down in two or three swallows. The rest of the night is like a movie on celluloid, the kind you use a projector for. Only most of it is melted and spliced together. And it's freezing in the theater. It's the first time in my life I ever "lost time," in the way that alleged UFO abductees mean that term. I have an uncannily accurate memory of my life, especially short term, most especially of emotionally-charged situations. But this was unnaturally broken. If you've ever gotten sedation for major dental work or been on codeine for pain, it was that sort of haze combined with confusion and the sense that nothing was real, not even me. And then at the depths of it, I have large gaps of hours where there's nothing. It just got dark all of a sudden, and I couldn't move, and I felt my brain willing my hands to move, and I thought they actually were moving, but my vision told me that this wasn't true. A few years afterwards I was watching The Serpent and the Rainbow, and the Zombification scenes gave me panic attacks, because that was pretty much exactly what it felt like. Except I wasn't afraid. Nothing was real or clear or precise or concrete or frightening or soothing. There was no pain, and no pleasure. I could feel the I was being touched, and that's about where I am stopping describing because I can't bring myself to write the rest yet.
About the high school boys, though: I also didn't quite believe that any of them actually thought I was pretty or that they respected me. I was just "different," and a virgin (later I found out that I lost my genital-penetrative virginity at least 3-5 years before a majority of the girls in my class. The other kinds I lost a while before to other opportunists who decided I was oblivious and wouldn't tell.), so they wanted me.
So it was painful, I guess. But not the way you want to know about.