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 3, 2011
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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 14, 2011
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A rare mishap which occurs during an after dinner wank.

When wanking you notice a rather significant sensation. It may be intensely painful or pleasantly warm, hot even.

You worry for a moment and even panic as it feels as though your sausage is being cooked. You look at your hands which appear clean. After a moment it clicks. You put two and two together.

Your meal was rather spicy, containing large amounts of high potency chilli sauce. Some must have gotten on your hands.
Dave: Steve, come down and check this out!
Steve: I can't right now, I'll come down in a few.
Dave: You're going to miss it! The cat's stuck in the toilet!
Steve: I can't, I've got a severe case of chilli willy.

Steve: *limps down the corridor*
Dave: What's happened? Did you get hit in the balls?
Steve: No, I've got chilli willy you silly willy.
by DeluxeFartJuiceLevelNine January 28, 2023
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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
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To stick your hand in a bowl of ice then masturbate.
When it's too hot out, phut often gives himself a chilly willy.
by Dan Steinke January 23, 2005
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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 27, 2015
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