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Random
When an individual takes a bite of a popcicle, freeze pop, fudge pop, etc. And performs fellatio to another individual.
Did you see that? Steph just took a bite of that freeze pop and gave that dope ass dude a Chilly Willy with that dong in her mouth!
When her hands are extremely cold and she gives you a hand job.
"How was your date with stacy last night? "
good, girl gave me a chilly willy.
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When you fill a condom up with ice-cream, not to be confused with a dirty-penguin, which is when the ice cream is consumed after use.
Oh my god my boyfriend game me a chilly-willy and i thought he was giving me signs!
When you put air duster upside down and blow it on your cock.
last night i did the chilly willy.
When you have sex in snow you pull out and scoop some up with your penis on the way back into a woman's vagina
Last night I had sex outside in the snow and gave my girlfriend a chilly willy
The single greatest feeling of pure adrenaline, induced through the snorting of vodka up one's nostrils. May get you intoxicated quicker and with greater effect.
Friend: Bro have you ever done a chilly willy?
You: No, what's that?
Friend: *proceeds to snort vodka and go batshit crazy*