An Urban Chestnut is what you leave on a hookers blouse (or any city dweller) when she blows you off in a St. Louis alley. Also, a St. Louis craft brewery which you may have visited before buying the BJ and depositing the Urban Chestnut.
Man, I had a couple of beers last night and totally gave my girlfriend and Urban Chestnut behind the Pita Pit.
by Xavier Brownwind July 13, 2013
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The "top-off" or "refresher" to a glass of wine. When the white or red liquid falls too far below the 6oz standard, remember to continue indulging with a chestnut topper.
Bill: "Your glass is looking low there, Tom..."
Tom: "Bill, I need a chestnut topper, fill 'er up"
by catdog29 July 2, 2012
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An idea or subject, usually flawed, which perpetually resurfaces in conversation despite having been discussed to death long ago.
A: If evolution is real then how come we never see monkeys turn into humans, huh?
B: Oh god, not that old chestnut...
by FeO2 August 16, 2011
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When one jizzes into a sock, then shoves it in another's throat.

Often used as torture, or really, really kinky sex.
"Mr. Bond, if you don't talk, I'm going to have to give you a Chestnut souffle."

"Dude, that chick that I slept with last night was so weird. She asked me to give her a Chestnut souffle."
by Mister Rection September 25, 2009
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A holiday sex move, when dirty hot sex has been going on for a long period of time, raising the body temperature of the man in turn raising his semen temperature. He nuts on the womans chest, thus a roasting chestnut.
Tim: Hey Dale what are you doing christmas day?

Dale: Visiting my in-laws at 5 which will lead to a roasting chestnut with my wife in her parents bed.

Tim: :/
by brandon2k9 December 3, 2009
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Where you nut, or produce sperm on a girls or a guys (if you go that way) chest and it is special because of the variety of colors/smells.
I gave that hoe a chestnut special last night.

She enjoyed my chestnut special.
by The Chestnut Guy July 27, 2009
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A upscale neighborhood in Philadelphia. Really an extention of the Main Line, but everyone there thinks they are better, because unlike the Main Line, Chestnut Hill has a large liberal population. It is an area filled with money, but subtly. There are a lot of hidden, huge, well manicured homes. All the kids go to CHA, Springside, Germantown Friends School and a few other well know private school in the area. Look out for the police who are constantly trying to break up parties with out doing anything to the kids and their fancy cars. Preppy is in style. If you have a car and are a teenager, the Wawa parkinglot is the place to be seen pre party on friday and saturday night, especially since the main road, Germantown Ave. is dead by 10.
person: oh you're from Philadelphia?
chestnut hill person: sort of, if you call Chestnut Hill the city.
by anonymous March 8, 2005
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