While having anal sex the girl starts to take a shit on the males dick but he keeps hitting her from the back.
dude I was having anal sex with my girl last night and she started shiting, but i didnt stop and had my first chilly hole.
by drumerboy888 June 10, 2011

The process of slicing multiple hot chilli peppers before getting a girl over, then chilli fingering her till her pussy burns hot like Mount Vesuvius back on August 24th 79 AD.
"Dude Becky cheated on me so i got her over and totally chilli fingered her all night"
"I was chilli fingering Amanda's butthole last night and she pulled the classic reversal and sprayed last nights fajitas all over me'
"I was chilli fingering Amanda's butthole last night and she pulled the classic reversal and sprayed last nights fajitas all over me'
by thechillifingerer November 23, 2018

when your in the pond at 4am and breaking thru the ice setting up decoys and start to sweat then go sit and wait and cool off thats Chilly bone ! Chillybone A.k.a. Robdog420
by Smokedog420 February 15, 2009

by Duke Mahogany November 14, 2007

by Nasty bugger July 10, 2010

When a guy puts his penis in ice water for 15 minutes or until his penis is very cold and shriveled up, and then he has sex with a girl doggy-style.
My junk was so cold but I knew I had to get a chilly dog, and although my dick was small and discolored, I fought through the pain to do it anyway.
by j morow January 18, 2009

When a male and female are having sex and the female is on her period which makes it look like the male has a chilli dog for a dick.
by JRR [Slick] December 16, 2008
