by MayDayMeh June 16, 2018

J.T. and Kelton shared a bed last night in Abilene. They did the Chicago Cheek Spread because the bed was too small.
by turkeymuffins3 March 28, 2011

typical pampered spoiled mid-western boy with mommy issues. Would rather be alcoholic, pill popper than admit his homosexuality. Marries older, foreign woman to keep his cover with parents
by Mark does John M July 14, 2008

When you take a girl out for mexican food, then assfuck her afterwards. It makes your hot dog feel like its in Chicago, the windy city.
Awesome Person:Why does your room smell like a chicago style hotdog?
Awesomer Person:Because your girlfriend just left.
Awesomer Person:Because your girlfriend just left.
by successfulheterosexual June 15, 2010

When a man has sex with a virgin, and continues to hump her while her vaginal blood is spilling all over his genital.
by Crastof Nikolayov January 19, 2008

a private high school in Chicago, it is so freaking awesome! It is the best school i have ever being ! _Vinny L
Tony: Have you heard about Chicago hope academy?
Kenny: H*ll Yeah It's the best high school in Chicago!
Kenny: H*ll Yeah It's the best high school in Chicago!
by Vinnnny L November 1, 2017

by Milwaukeeboi148 December 18, 2018
