Top Definition
The sex act where two or more individuals take a piece of fruit (preferably a cucumber) and stick it up their partner's anal area multiple times. "Chesire Cat Smilers" are of those who perform this act. It is common knowledge that chesire cat smilers also eat the fruit afterwards no matter how dirty or grotesque it has become during their sexual routine.
Person A opening person B's legs while laying on the floor and jabbing the cucumber into their anal area while they perform the Chesire Cat Smile.

A: Fancy doing a Chesire Cat Smile with me honey?
B: Sure why not!? It's been long since we became Chesire Cat Smilers for the night. Go on, in you get cuccy (slang for cucumber).
by Look_whos_boss March 07, 2011

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