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Originally the term for harpooning a whale in a rickety boat usually meant to hold no more than 16 people, and letting the whale swim itself tired before killing the whale

Popularised by whale killing off nantucket island

Mainly found in old whaling books, and Moby Dick
by Flambeau February 28, 2005
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2
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.
by Museum Man June 19, 2005
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3
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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4
a sex act in which the female is halfway on the floor with her ass and legs on the bed,(as if sleding face first,belly down.When it comes time for the male to spooge,he pulles it out and lets it snow.
Hey conor last night your mom and I took a nantucket sleigh ride!
by Matt April 21, 2003
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5
WHALING.... DUDE a "Natucket Sleighride" is a WHALING term....

Dear God....
Example.... isnt it pretty self explainatory?
by Nantucket is for lovers.... February 25, 2005
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6
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.
by Dongdangling Facepumper May 21, 2008
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7
you bang a fat girl while she's in bondage. Then you let her go after a week and ride her ass as she crawl the refrigerator for food.
Person 1: Where you the last week?
Person 2: I took a real huge porker on a nantucket sleigh-ride last night.
Person 1: Was it the best time of your life?
Person 2: Absolutely.
by All the Difference May 22, 2010
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