Top Definition
To injest alcohol through the nose via snorting, in order to get the alochol into your system quicker. Often done out of the concave bottom of a shot glass.
That chilly willy was fun huh? wait...get up, why are you passed out?
by Jeremy November 03, 2003

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When one's sex partner sucks on an ice cube, drastically lowering the temperature of their mouth and tongue, prior to giving you oral sex.
LaFawnduh gave me a chilly willy in the bathroom on the bus to Detroit. That's when I knew I was gonna marry her.
by dcf68 June 23, 2006

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The most iconic building on the Chicago skyline, the Chilly Willy stands at a towering 108 stories.
Was formerly known as the Sears Tower, but became dubbed the Chilly Willy after Sears sold the tower to the Willis Group, a British insurance brokerage, much to the dismay of the new owners.
Friend 1: Hey Dawg, want to go down to the Sears Tower Skydeck tonight?
Friend 2: Didn't you hear? Sears sold the tower, it's officially the Chilly Willy now.
Guy 1: Hey, how long is the line to the skydeck?
Willis Group Employee: Excuse me, I believe you meant to ask how long the line is to the WILLIS tower.
Guy 1: Hah, Chilly Willy
Willis Group Employee: Please don't call it that
by countDantes February 04, 2015

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When a man sits on the toilet and the tip of his penis rubs against the cold inside of bowl, or possibly even the water. This could also be known as a Tip Dip.
"Time to drop some plop" *sits down* "Oh no! I got a chilly willy! I hate that!"
by Oh Yeah! Teh Cap'n! August 24, 2008

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when icecubes are put in the mouth before performing a blowjob
Carly gave Noah a chilly willy
by richhomiejoel March 16, 2016

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The act of dipping one's penis into a bucket of ice water and without warning, jamming it into a female partner's gash.
So I was banging this chick down by the lake right, and the ice was frozen. So I dipped my stick in the frozen lake water, and gave her a chilly willy.
by pdb5 January 27, 2011

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When a partner does not know what a blow job is, so they literally blow on your penis, hence making your penis "chilly"
"man Mildred had no clue how to give head, so she gave me a chilly willy"
by Analtickler September 05, 2016

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