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A "Nantucket Sleighride" was the result of harpooning a whale. The ship subsequently was dragged behind the whale by a line running from the harpoon to the ship. The Nantucket Sleighride would continue until the whale died, the line broke, or the ship sank.
After harpooning the whale, the good ship "Alabaster" was taken on a Nantucket Sleighride for nearly an hour.
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Originally named for the act of harpooning a whale and being pulled by the harpoon line until the whale dies, the line breaks, or the boat sinks, the Nantucket Sleighride is a sexual experience where you have your pecker stuck in a woman bigger than you and she drags you around the room trying to break free.
I was plowing this huge woman and my cock became stuck in her ass, so she gave me a Nantucket Sleighride trying to get it out..
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WHALING.... DUDE a "Natucket Sleighride" is a WHALING term....
Dear God....
Example.... isnt it pretty self explainatory?
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–verb
The act of stabbing your obese partner while having intercourse and then riding her until she goes down.
Jordan: Hey man, did you take down that whale??
Clifford: Yeah, I totally Nantucket Sleighride(rode) that bitch!
Jordan: No way! How long did it take her to go down?
Clifford: ...about 45 minutes.
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Sexual act, where female, atop the male in a traditional "69" position, snorts a line of cocaine off of his appendage while enjoying his oral dexterity. Hence we have the "snow" and the "ride."
Due to his enormous prowess, ability to keep his unit perfectly still and his Columbian connections, Frank was able to give Lisa quite a few Nantucket Sleighrides back in the 80's.
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The act of snorting a line of the substance of your choice, out of the valley of your spouse/lover/random hobo's butt crack and taint.
Sexual Slang akin to the Dirty Sanchez, Donkey Punch, and Brunswick.
Man, you got some sort of brown schutz hanging from your nostril.
Oh, Thanks. I just did a Nantucket Sleighride with your aunt in the wine cellar, guess the snow was starting to melt...
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The act of knocking a woman out during intercourse with a sharp blow to the head, positioning her belly-down at the top of a staircase, and then while sitting atop her back, riding her limp body down the stairs. This act is performed much in the same way a sled is ridden down a snow-covered hill. Steering is accomplished by bringing the arms up behind the back; pulling on the left arm turns the sleigh left, and vice-versa for pulling on the right. This act is almost guaranteed to be good fun for at least one person.
"Why is Mary's entire face in a cast?"
"Ohh, Ted gave her the old nantucket sleighride."
"....oh, what fun."
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