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).