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

Chillbilly

Same as hillbilly, but reserved for people of colder regions.

Sarah "Chillbilly" Palin should really get out, and stay out of politics.

by JuanB July 13, 2009

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

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

chillybilly

An adjective/adverb that means as much as the less familiar 'chillaxy-paxy'. It means very chill. Almost that chill that it has became lame, boring and long.

Guy 1: 'Sup
Guy 2: Nothing much. Just have been chillybilly surfing the Internet for the last couple of hours...
Guy 1: With your chillaxy-paxy computer?
Guy 2: Indeed...

by somethingbrown November 5, 2010

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