Where it happened: home
I was in high school, and part of the chess team. On this day, several of us were at my folks home, where we would practice and have fun. Now, my chess ability is above average at this time, and I felt I could beat anyone on the team. When my folks went out of town for the weekend we held the practice as normal, but with a difference this time…we decided to spice the games up with the losers having to do whatever the winner wanted as a prize, and I do mean anything.
I won the first two series of games (best five of eight) in each set and had the guys do some humiliating stuff, but about this time, one of the girls had lost, and had to strip naked for the rest of the night; now that got things going to a new level. Soon enough, some of the guys and the other girls were getting clothing removed. The third set (best three of five) I lost, to Trevor of all people, and waited to hear my fate. He grinned and looked from me to the couch and back again; then declared to all “your penalty is to let me fuck you here in front of the whole club.”
The silence following was intense for a moment, then what happened next was a mix of me getting stripped by my friends, and Travis shortly laying on top of me on the couch. Soon enough, he stopped squeezing my breasts and got to work with his penis, fucking me for several minutes straight, which I had to endure because it hurt so much and he weighed more than me (not by much, but enough) and was glad it was finally over.
I thought the worst was over for me; until nine months later my little girl “Corra” was born.