Beautiful and complicated. Strong willed and incredibly loving once they let you in. Sharp tongued and witty.
Damn that person is quick they got the Chesire skills.
by straight up Jack July 21, 2010
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 7, 2011
v: Smoke or otherwise ingest drugs until you are so stoned that your only noticeable features are a shit eating grin and a pair of bloodshot eyes.
she just finished vaping an entire pen. Chesired to the max.
by Krinkles the Klown November 30, 2020
chesire: meaning a world to tease someone in a playful way
also a word used by bayonetta
hello there chesire
by Ceraza February 19, 2019
An animator on YouTube with ≈100 subscribers that has a terrible upload schedule.
"Hey when will Chesire post again?"
"No damn clue."
by Spaget09OnYT October 1, 2022