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.
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