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A typical initiation in interior Alaska for new military members joining their a work team. The initiate is bought a shot of 100 proof rumpleminze along with a bottle cap full of the same accompanied with a straw. They then snort the bottle cap of rumplemimze and take the shot.
Welcome to hell literally froze over just like this Chilly Willy.
When a partner does not know what a blow job is, so they literally blow on your penis, hence making your penis "chilly"
"man Mildred had no clue how to give head, so she gave me a chilly willy"
a penis that has been deep-fried, covered in peri peri then frozen
you've got a chilly willy
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.