Green’s Dictionary of Slang

a trick whereby one pulls an unsuspecting victim’s underpants up between their buttocks; also used as v.

1977		J. Langone Life at the Bottom 31: ‘What’s a wedgie?’ ‘Well, sir, that’s when they grab you right there by the ass of your trousers and give ’er a good tug.’.
1987		G.A. Fine With the Boys 170: The simple trick of tugging on someone’s underwear, called a snuggy in Minnesota and wedgie in New England.
1988		Wash. DC WTTGTV [Gary Shandling’s Christmas Programme] 18 Dec. [TV programme] I think I’ve just given myself a wedgy.
1989		Michael Moffatt Coming of Age in New Jersey 86: Last year’s juniors had wedgied last year’s freshmen.
1992		S. King Gerald’s Game (1993) 8: The bullies were still giving Gerald wedgies in study-hall.
1996		Irish Times 5 May n.p.: The Wexford People said that two Wexford ‘bullies’ were sent home from the Gaeltacht for inflicting ‘wedgies’ [BS].
1997		Roger’s Profanisaurus in Viz 87 Dec. n.p.: wedge v. To pull another’s underpants up the crack of their arse. n. A wedgie.
2001		OnLine Dict. of Playground Sl. 🌐 wedgie n. Humiliation where the underpants are pulled sharply upwards from behind, causing them to wedge themselves tightly up the victim’s arse. Variations: Pure wedgie: The victim is only wearing underpants when the attack occurs, thus inflicting a much greater amount of embarrassment than normal. Super wedgie: Pure wedgie but with the assailant then grabbing the crotch of the victim’s underpants (from behind as it is exposed) and continuing to pull, resulting in the victim’s genitals being revealed. (This is particularly embarrassing if the victim is not quite flaccid.) Wedgie war: All-against-all with lots of ganging up, normally in a swimming pool [...] Wedgie-proof: The victim’s underpants are so stretchy that the wedgie doesn’t hurt, or they are wearing Speedos, which tend to just stretch instead of heading painfully for the buttcrack.
2005		Mad mag. July 53: She was having fun until he gave her a wedgie.
2015		S. King Finders Keepers (2016) 78: Step out boys [...] Arm’s length fom the upstanding American in front of you. No wedgies and no reach-arounds. Don’t fuck with us, and we will return the favor.