1 definition by JFins

A: Noun: An act of sexual intercourse wherein the couple is engaged in "doggy style" and the receiving partner is unaware that the active partner has placed a pumpkin, or Jack O Lantern upon his head. When the receiving partner turns to look, she is greatly startled and oftentimes thoroughly scared by the sight.

B: Verb: The act of placing a Pumpkin or Jack O Lantern upon ones head during sex with the intention of "Fucking With" one's partner.

Note: First Invented at Drew University. Most Appropriate around or on the time of Halloween.
"Dude! Last night i was banging this chick, and i Sleepy Hollowed Her! It totally freaked her out, though. She hasn't answered any of my calls."

"Hey Bro! We should totally grab some of those Jack O Lanterns in front of Hoyt and Sleepy Hollow some chicks tonight!"
by JFins October 18, 2009

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