Whenever my fiancee sends me nudes of herself, I "accidentally" send them to a friend that is hanging out with this prick I absolutely hate. Once I "catch" my mistake, I brag that she's still a virgin and I'll be fucking her senselessly after our wedding. I hope he decides to try and seduce my fiancee and succeeds. My fiancee knows how much I like being sexually humiliated, so I think there's a chance.

My darkest fantasy is for him to take my fiancee's virginity. The fact that my fiancee would let someone she knows I hate have something so special, and that I will never have it would be the most humiliating thing I could ever endure. I hope his dick is much bigger than mine, that her virgin c**t squeezes his dick tighter than any pussy he's ever fucked before, and enjoys being the first person to cum in her. I hope he makes her cum nonstop and ruins her for me, so that she prefers him to me.