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100 miles of bad road 

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When a man or woman's face is extremely ugly!!!
person1)Man, she looks good!
person2)Her face looks like 100 miles of bad road!
100 miles of bad road by horsefly October 10, 2005
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Related Words
miles of smiles • Miles off it • 100 miles of bad road • Fifteen Miles of Bad Road • 30 miles off London • looking like five miles of bad road • mines of moria • mile of cock • Mile of Dick • mesmerizing moles of majesty

looking like five miles of bad road 

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Southern expression meaning someone or something looks severely disheveled, exhausted or sloppy, like an old road in desperate need of repaving.
She woke up the morning after the party looking like five miles of bad road
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Fifteen Miles of Bad Road

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When someone, as they age, goes from looking hot to looking like fifteen miles of bad road
Have you seen Lia? She was hot in high school! She looks like fifteen miles of bad road now.
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Mile of Dick 

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1 mile = 5,280 feet = 63,360 inches
The national average penis size in the US is 5.5 inches.
63,360/5.5 inches = 11,520

There is approximately 11,520 dicks in a mile.
Yo Mama is such a hoe that she has a Mile of Dick twice a week!

Tim: Man! Sally has hooked up with everyone at work, except me. Glad I'm not part of her Mile of Dick.

Tom: Speak for yourself!
Mile of Dick by NobeeCares January 9, 2023
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I would drag my dick through a mile of broken glass just to hear her fart through a walkie talkie 

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A phrase used to explain of the lengths one would go through for a female.
I would drag my dick through a mile of broken glass just to hear her fart through a walkie talkie
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I will eat a mile of her shit to see where it came from. 

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A term used to describe an incredibly beautiful woman with a perfectly shaped butt.
Dude, she's so fine I will eat a mile of her shit to see where it came from.
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