My father plays in an amateur band and invited me and my girlfriend to a festival. We were to sleep in a large tent with all his band members. After they'd had their concert, the drinking got out of hand for all parties. My girlfriend and I made a dumb bet with our father. If he won, he would get to sleep with her. If we won, we stood to win a rather large sum of money. We thought it was all in good fun and honestly, the money was tempting.
And then we ended up losing that bet. My father wouldn't let us off the hook. He insisted we go back to the tent so he could collect his prize, that is to say, my girlfriend. There were several problems with this. We'd never done it before and my girlfriend was a virgin. He told us he would take her virginity and this would help bring us closer in our relationship. I didn't feel like watching, but neither could I just abandon her. At this point we really regretted it all.
So, he got her lower parts undressed and got on top of her on a sleeping mat. While I held her hand, he put his penis inside of her. It really hurt her and he looked like he was about to get a heart attack, moaning and breathing heavily. Adjusting took both parties quite some time. My girlfriend not hurting so much and constantly going "Ow" and "Oww." And my father not having some sort of medical event.