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4.
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
 
1.
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
 
2.
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
 
3.
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
 
5.
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
 
6.
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
 
7.
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 August 21, 2005