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chilly pimp 

A fake gangster; someone who thinks he's a part of the gang but really is just ridiculed and berated by all.
Yo you met that guy Ford yet? He's a real chilly pimp. He ain't shit.

Chilly Perkins 

Unbearably cold, usually induced by a sudden change in temperature i.e jumping into a freakin' plunge pool in the arctic.
Bear Grylls: THIS is going to be chilly perkins *dives into epically cold waters*

Eskimo boy#1: Man, it's chilly Perkins out here!
Eskimo boy#2: Knows it bro! I think my nipples just fell off!
Chilly Perkins by Hurley665 July 20, 2009

small chilly pepper 

It basically refers to a small penis in Korea. When Jimin was talking about his parent's dream, his parents had mentioned seeing a small chilly pepper hanging from a tree.
Jungkook: " Hey guys I saw Jimin's penis when we had to take a shower, he has a small chilly pepper. "
Jimin: * bursts out laughing *

Chilly Palmer 

When a man is having intercourse with a girl, he pulls out and blows his load into a handful of crushed ice and slaps a woman on the back.
My girlfriend called out her ex's name, so I grabbed a handful of ice and gave that bitch a Chilly Palmer
Chilly Palmer by Pussyhands Icechest December 31, 2008

Chilly Palmer 

Placing your hand in an ice chest for 5 minutes before masturbating. You may also use a fridge, freezer, or Canada.
"Man, I felt the need to punish myself so I finished my day with a Chilly Palmer."
Chilly Palmer by Revolution1117 October 23, 2007

Carving the chilly pumpkin 

When you simply take an ice rod and insert it analy into the girl. After the butthole is numb you cut the edges of the butthole so it is bleeding. When you insert your penis into the butthole you will come out with ketchup on a hotdog, the blood makes the feeling more slick.
Bro I carved that girls Alaskan pumpkin the other day!

I was carving the Chilly pumpkin on this girl last night.