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
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
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
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
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
Freezing excrement in order to have inter couse with it
Man Jeramy gave me a chilly willy now I have poop in my vagina
by Masterdebator May 30, 2015
An electronic and dance mashup artist from Portland, Oregon. Beloved by many, he has yet to gain exposure, but his music is beyond comparison.
Last summer I was feeling good so I got silly with Chilly Willy over the three day weekend.
by chilywillyfan September 02, 2011

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