Chilly Willy

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! October 16, 2008

chilly willy

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

Chilly Willy

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 4, 2011

chilly willy

a sexual activity in which the male freezes his penis with ice and then has sex with his partner

"Dude she said she likes it cold so I gave her a chilly willy!"

by mezmerak November 13, 2011

chili willy

Inserting a cold penis into a womans vagina.

Yeah, i woke up and put my dick in the freezer for half an hour and then gave that bitch the chili willy!

by shomasa November 22, 2011

Chilly willy

When your dick is as hard as a rock

I have a VERY chilly willy

by Big boy Big lad February 23, 2020

chilly willy

Take a man's penis and dip it into a Milkshake or a glass of ice water before giving him head!!!
(Keep in mind the Milkshake is more fun and adds flavor as well)

hmmm Baby it's hot let me cool you and me off by giving you a "chilly Willy"

by Paula aka Mouse September 15, 2005