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
Nantucket Sleigh Ride
by Flambeau February 28, 2005
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
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."
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
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
–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.
by SailorMan March 05, 2010
Amateurs. A Nantucket Sleigh Ride is when you lay your special lady face down naked. You take her by her hair and slip the heels of your fit into her arm pits You then drop down on her going deuce hole. You then hang on and enjoy the ride. Properly performed it will bring back childhood memories of taking your flexible flyer down a hill of fresh powder.
by Emo2 February 15, 2011

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