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Cuckholding 

The act of getting pleasure by watching your significant other engaging in sexual behavior with a third party person
Ryan Carruthers sure does enjoy the act of cuckholding
Cuckholding by Bergeron37 November 26, 2021

Chicago Cupholder

When you shit in someone's hand while they're asleep and tickle their face with a feather.
"Hey, were you at that party last night?"
"Yeah man, it was nuts. I heard some guy passed out and someone gave him a Chicago Cupholder."

Cuckoldery

The official word for the practice of "Cuckold" "Cucked" and "Cuckery". Cuckoldery has been practiced to bring more "Spice" in a relationship. Men allow other men to have sexual activity with their spouses. In echange they receive pleasure. Another case in when a man practices cuckoldery is when he is diagnoses with erectile dysfunction, these men recieve pleasure and joy from their spouse engaging in sexual activity with another man.
"Me and my wife want to spice up our relationship. I think we might practice cuckoldery."
Cuckoldery by MathewsDmitriDaSilva February 7, 2017

Cuckoldrix

A strong and sexually powerful married woman who exherts her dominance over her husband by openly cheating on him with other, usually more well-endowed alpha males.
Jill became a cuckoldrix when she realized she no longer had to settle for sex only with her pathetic excuse of a husband.
Cuckoldrix by sk666 February 25, 2011

cuckoldress 

A woman who cuckolds her husband. The husband, or boyfriend, is a cuckold.
He married a cuckoldress who slept with all of his friends.

cuckhold 

Not simply a man who's wife/girlfriend cheats on him, but rather a man who actually gets aroused by knowing or seeing her in sexual situations with other men, such as flirting, kissing, fondling, or sex. In particular, situations where he is NOT participating but instead marginalized, just observing, or even completely ignored.
You should have seen Frank smiling as his wife was flirting with other men at the club, even allowing them to grope her; I swear it was giving that crazy cuckhold a hard-on.
cuckhold by D13732 September 26, 2008