A gentleman's Duel is when two men sit on their knees, usually on a bed, and proceed to masturbate until they ejaculate. The first person to land a load on the other man wins.

The term's first noted and recorded usage was in the Seananner's video,"WEIRD GAMING CONVERSATION"
"Last night me and Kyle did A Gentleman's Duel."

"Oh, did you win?"

"I always win A Gentleman's Duel."
by Analcream July 11, 2017
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Two men race to ejaculate into a woman's holes being either the vagina, asshole, or mouth. The last man to ejaculate in the interaction is generally obligated to give fellatio to the winner.
Hey, did you win the gentleman's duel last night?

Nah man, I lost, but thankfully Tom's dick didn't taste too bad!
by Musicman182 October 30, 2023
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