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Cuckholding is when you reach around your sex partner who is on top of you and use their asshole as a grappling or anchor point for your hands. Anything short of using at least three fingers from each hand doesn't qualify as a true cuckhold. This move can be useful when you are revenge fucking some chick and you want to really drive the point home.
Dude, I had to put your sister in a cuckhold last night to keep her skinny ass on top of me while I banged the shit out of her.
by Prof. Kdog March 25, 2008
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A word which describes the true intelligence level of those who use the term cuckold outside of its fetish meaning.
Did ya see that incel calling me a *cuckhold* on facebook, eejit!
by sixfootnothin April 24, 2020
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Mmmm yes Oprah, use me as your personal CUCKHOLD!!!!!!!!!!!!!!!

I'm diggin' a hole with a CUCKHOLD.
by PoOp1211 August 15, 2018
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Often times appears in a toxic relationship in wich the woman takes advantage of the man who fell in love with her by demanding materialistic things. Sometimes this event can lead up to the point where the man has to break contact between him and his friends. (RIP to my homie Pat)
M: Dude i just bought her a new car and she still won't let me hit!
A: Dude! You're being cuckholded!

OR

M: Sorry guys i can't hang tonight. She said im not allowed to.
A: Are you going to have sex?
M: Nah dude don't think so she said i will have to wait. But tomorrow for sure!
A: Dude you're being cuckholded!
by KysBuddy July 01, 2020
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