This is a sex game who ever orgasims first loses and the winner screams checkmate.
Mikayla- I'm cumming Tom- CHECKMATE!
by DA WOLF 6 February 04, 2016
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When you do a super cool skateboarding trick you've been trying for so long
"checkmate! That was swag, did i really just did that??"

Try saying it while you flip your hair.
by Mollyollyoldlady July 10, 2021
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To force a man to achieve an erection, whether through immense attractiveness or unwanted physical contact.
"I took one look at Kellie and, well, it was Boner Checkmate."
by Jkeith May 14, 2014
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