My biggest cuckold fantasy is to find out my wife is cheating on me with black men behind my back and to be able to observe without her knowing as I watch her do things with them and orgasm more than she ever does with me.
Similar thought here, mine has been with another guy years ago (white)
Care to chat sometime
 
We go out for the evening, my wife and I, to a bar. She sees a handsome black guy and makes eyes at him. He approaches her and they hit it off, I am there just watching. He invites us (her really) over to the table with his buddies and it becomes clear that they want to fuck each other. She is getting a bit tipsy and loose and is also flirting with another of this guys friends. There is serious flirting, petting, then making out all in this public place, this married white woman and a couple black guys, all in front of her husband. People notice. I am pretty humiliated but completely hard in my pants, making a wet mess in my underwear. She takes the first guy to the bathroom, while his other buddies chide me in a semi friendly way. When the two of them come back she says it's time to go. The guy she went to the bathroom with is whispering in the other guys ear and when we leave, it is the four of us. She tells me to drive home as she follows with the two of them in their car. She takes them to our bedroom but allows me to watch as she gets fucked, sucked, and bred in our bed by two hung black guys. How is that for a cuckold fantasy?
That was pretty damn good!!
 
My wife tries cuckolding because of my sexual failure. The black man and her have good sex, she is really satisfied for the first time in years, the best sex of her life. They meet more often. my submissive tendencies are incorporated. That means I have to wear women's underwear, I'm humiliated because of my penis, I can't satisfy her sexually. They meet often and at some point they have sex without a condom. I no longer have sex with my wife, I'm only allowed to masturbate. She gets pregnant even though she uses contraception. She wants to carry the baby to term and start a parallel relationship with me and the black man. We move in together. Gradually, my wife also becomes more submissive, he becomes more dominant. While I look after their baby, he goes out with my wife and offers her to his friends for sex. My wife is filmed having sex and I am allowed to masturbate to these videos in front of both of them. I'm trained as a sissy and given hormones, they both want to feminize me...
 
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