I was a freshman in HS he was a senior, we were both on chess team, one day he invited me to his house after school to go to play chess. I hate wearing shoes and had removed them when I got in his car. We went up to his room, set up the board, started playing then he asked me to remove my shirt which I did without thinking. He stripped, one thing lead to another, I was on my back with legs on his shoulders, getting fucked. It hurt like crazy at first but I bore the pain then it started feeling great, he dumped his load in me, I jacked and came all over my chest which he scoped up with his fingers sticking them in my mouth which I sucked clean. He took me home, he fucked me several times a week until school ended. He went off to college and I never heard from him afterwards.