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1.
The act of holding a female above your head in Stanley Cup fashion after engaging in intercourse with her. After NHL players win the Stanley Cup, each player holds and kisses The Cup in a specific, triumphant manor. This may be achieved by inserting your left middle and ring finger into the female's mouth, inserting your right middle and ring finger into her vagina, hoisting her above your head, lowering her to your mouth and kissing her stomach.

Origin: University of Delaware, 2011
"Bro, I just Stanley Cupped that tiny bitch."

"Bro, I just Stanley Cupped that huge bitch."

"I felt like a winner after Stanley Cupping that bitch."
by technoruss June 12, 2012