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To cheeri someone's o is to please their vagina or anus. Cheeri my o is an instruction to do this by means of manual stimulation.
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See: Douche, whipped,bitch, pussy, fucktard, pizzaface, anal dwelling whore, gross, chubby, man tits, squishy, ugly, virgin, uber virgin..
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Winning at multiple tasks, schemes, games, etc. at once,
Matt won the bet he placed on the game, won the money prize in poker while wat..