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It's like how a cat tip toes around sneakily.
Describes an action.

Represented by 😏 emoji.
Mom said no to cookies. But me and my sister cadily swiped some while she was sleeping.

Me and Tanvir France were texting and he dropped innuendos, cadily steering the conversation towards sexy stuff. He's so smoooooth. 😏😏
Cadily by Peppa🐽 June 28, 2021
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Jump in the Cadillac

Tommyinnits worst nightmare

This is house

Donation: jump in the Cadillac
Tommy: jump out the Cadillac and jump off a bridge

Cadillac Draw 

The maximum canteen draw allowed per month in prison.
Ex. 1

Prosecutor: What was the amount of money that was sent by a money order here?

Enriquez: $60, about the maximum canteen draw allowed per month, what we call a Cadillac draw.

Rene 'Boxer' Enriquez, USA v. Jaimez, September 12, 2018.

Ex. 2

Lil Smiley: Odelay vato! Just paid a visit to the canteen! I got six soups, five candy bars, four bags of chips, three mints, two packs of gum, and a partridge in a pear tree!

Spider: Damn fool! You pulled a Cadillac Draw! I'll trade you a couple fuck books and a fifi for the candy bars!
Cadillac Draw by FAIMnatic October 23, 2020

Jump in the Cadillac

Tommyinnits famous thing
Fan: "jump in the Cadillac"
Tommy: "die"

jump in the cadillac

Dono/Donation: “Jump in the cadillac girl put some miles on it

Tommy: AHAHHAHSHSHDJFISN FUCK YOU FUCK YOU FUCK YOU FUCK YOU

After the dono disappears: OK ANYWAYS

Cadillac Pussy 

This is a very luxurious vagina that a lot of people wish they could own, but only very few people can actually afford. It (the vagina) not only looks fantastic, but also feels exceptional on the inside.
I know that woman has a "Cadillac Pussy" but I just can't afford it.
Cadillac Pussy by Hank Jr. June 12, 2013

the cadillac

A large luxurious handicap stall in a public restroom.
The whole bathroom was empty so I got to use the cadillac.
the cadillac by SirScarface69 August 11, 2010