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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."

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

Cuckhold 

A man that watches his wife perform unfaithful activities.
Malachi is one good cuckhold.
Cuckhold by fwvon October 15, 2019

swedish cupholder 

I swedish cupholdered a chick last night she still smells

Cuckholding 

The moron decided he wanted some cuckholding experience, but the Cuckolding Princess laughed at him when he got the word wrong.
Cuckholding by Cuckolding Princess November 2, 2011