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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 22, 2011
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Smile

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To arose a woman without talking to her. Silent seduction.
"Yo ma nigg, you wanna hit up the mall tonight?"
"Hell yeah, bro, let's go smile!"
by Jimmy Tapper January 6, 2009
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When one or more people instant message someone, and bombard them with a frenzy of smiley faces.
Happydudezzz (1:54:29 PM): hello
so yea im ryan (1:54:18 PM): hey
Happydudezzz (1:54:36 PM): (large sum of smileys)
so yea im ryan (1:54:27 PM): wtf
Happydudezzz (1:54:43 PM): (more smileys)
Happydudezzz (1:54:47 PM): (even more smileys)
Happydudezzz (1:54:50 PM): (yes...more smileys)
so yea im ryan (1:54:38 PM): what the fuck is all this emotions
Happydudezzz (1:54:59 PM): (a flurry of smileys)
so yea im ryan (1:54:49 PM): ahhhhh.

Aim attack (smiley attack)
by monroe perry December 5, 2007
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The Smiler

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A Rollercoaster at alton towers in which you loose your legs
im going to loose my legs on the smiler today
ok have a good one mate
by Timmy Tuncan December 2, 2020
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A simple game played by a group of guys on a friday night. Get one female and put her under a table. Guys sit around the table. The girl then starts to give random blowjobs. the first person to smile has to pay for the beer and the girl.
Guys lets go play smilies tonight
by Degrace June 19, 2009
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silly or ridiculous smile with teeth sticking out.
children were making funny noises with goofy smiles on their faces.
by logophile.yza October 8, 2015
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An insincere, sad attempt at smiling
An incredulous expression is less wistful than a wasted wistful wishful smile reposite.
by Hercolena Oliver May 29, 2010
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