Chicago Shoe Shine

A sexual act where the person giving oral pleasure to a penis has the male take their penis out of their mouth before they climax and makes them finish onto their feet. You then wait 40-60 minutes for it to dry before getting your partner who has came on your feet to peel it off, eat it, and then lick your feet clean

I gave him a Chicago Shoe Shine! It was incredible

Chicago Shoe Shine by World of Keflings Master May 28, 2026

chicago shoeshine 

When you pay $20 to a homeless person to get you off on the side walk. Then they wax your shoes clean with a mixture of their spit and your spooge

Livingston was lost on Ohio St. so he paid a homeless guy for directions and ended up getting a Chicago shoeshine. It was more than he bargained for.

chicago shoeshine by The Sweens June 19, 2016