My cuckold confession is that I crave humiliation. None of my past girlfriends ever knew but I pursued them because they were known as sluts that you could easily hookup with. That was exactly why I wanted to date them, because I knew they’d be most likely to hookup with others behind my back or cheat. They’d also be most likely to have sucked and fucked guys with much bigger dicks than my 5in hard on.
So while I dated them I got them to admit guy’s dick sizes and tell me about past sexual experiences. I even got a few of them to cheat on me after I setup the whole situation beforehand.