Green’s Dictionary of Slang

1. (US) the anus.

1973		in TULIPQ (coll. B.K. Dumas).
1986		J. Ellroy Silent Terror 67: [A]ll the ‘boodie bandits’ looking to travel up the ‘Hershey Highway’.
1988		H. Max Gay (S)language.
1990		S. Morgan Homeboy 179: There’s been so much stick pussy shoved up that Hershey road they could rent it out for a convention center.
1998		H. Robins Predators 196: Then she taught me how to drive the Hershey highway and she masturbated her own clitoris until we both collapsed together in a wave of orgasms.
2000		T. Udo Vatican Bloodbath 81: Matta fucken Hari? Real name Hershey P. Highway.
2003		www.thepantsman.com 🌐 How does one avoid such a disappointing end to a ride up the Hershey highway?
2006		A.H. Zane Shame on It All 216: I wouldn’t mind finding out how a thick, juicy dang-a-lang would feel up the old Hershey Highway.
2009		N. Flexner Disassembled Man [ebook] Were you sticking your pin-dick into the Hershey highway? You fucking faggot.
2014		asstr.org 🌐 I kept on plowing in and out of Mommy’s ass while Mommy kept pounding Natalie’s ‘hershey highway’.

2. attrib. use of sense 1.

1997

J. Lansdale Bad Chili 197: Custer decided to phone his parents about the fact that he’s a Hershey highway kinda guy.

1. (US) diarrhoea.

1981		S. King Cujo 222: By tomorrow morning I’ll probably have the Hershey-squirts.
1986		C.R. Johnson Sorcerer’s Apprentice 71: Another attack of Hershey squirts, probably from the meat pie.
1990		S. Morgan Homeboy 135: [...] running to the bathroom every fifteen minutes with the Hershey squirts.
2007		F. Michaels Free Fall 319: Once those Krystals navigated their way through her sister’s gut, she’d have the Hershey squirts for days.

2. (US campus, also Hershey stains) faecal stains on one’s underwear due to liquid emitted when breaking wind or through a badly cleaned anus.

1973		in TULIPQ (coll. B.K. Dumas).
1982		S. King Different Seasons (1995) 398: You won’t mind if we examine the seat of your Jockeys for Hershey-squirts, willya?
1985		J. Wambaugh Secrets of Harry Bright (1986) 54: We gotta give him back at least nine grand. Damn, I got Hershey squirts in my shorts!
1990		(con. c.1970) G. Hasford Phantom Blooper 60: You cannot tell a beautiful woman that the reason you can’t sleep is because you sometimes still get the Hershey squirts.
2001		J. Lansdale Captains Outrageous 278: ‘Dirty underwear, dear,’ Jim Bob said. ‘Ones with the Hershey stains in the seat.’.

(US) to perform (homosexual) anal intercourse.

1989–2003		R.O. Scott Gay Sl. Dict. 🌐 anal intercourse: [...] Syn: hershey highway.
1997–2002		Alt. Eng. Dict. 🌐 hershey highway (noun) lower intestinal tract surrounding the anus [...] ‘Hey Bobby.....you want to ride down my hershey highway?’.
2001		OnLine Dict. of Playground Sl. 🌐 Hershey Highway n. Anal sex. Current usage in USA, where ‘taking the Hershey Highway’ carries the same meaning as ‘fudge packing.’.