It happened with my first real boyfriend. I and he 6. At the time, we loved each other.
We would always mess around in the roof area of my building because we really had no other place to go. We would just sit around for hours tonguing and exploring each other’s bodies. I was the first to give him oral sex.
So it happened one day that we were dry humping, and i was on top of him naked and he had a hard on. I was dripping wet, and it just sort of slid right in. It hurt like a bitch! I did not know he popped my cherry until I sat on his face and there was blood in his mouth when I lifted back up.
It continued to hurt the next few times we tried. (We figured we might as well start screwing even if the first time was an “accident”)
I got bored with it after a few months and yearned for another body. So I cheated on him and dumped him.