Green’s Dictionary of Slang

1. to have anal intercourse, to sodomize; thus cornholing n. and adj.

c.1930		(ref. to mid-19C) N. Kimball Amer. Madam (1981) 25: They horse around a lot, with pecker pulling and talk of cornholing and country buggery.
1949		in Randolph & Legman Ozark Folksongs and Folklore (1992) I 503: Colombo had a one-eyed mate, / He loved him like a brother, / And every night in the upper bunk / They’d corn-hole one another.
1959		W. Burroughs Naked Lunch (1968) 220: Are you going to cooperate [...] or does the . . . does the Man cornhole you???
1967		P. Thomas Down These Mean Streets (1970) 161: Jus’ take your pants down an’ we jus’ do a li’l corn-holin’ with you-all.
1969		H. Ellison ‘A Boy and his Dog’ in Beast that Shouted Love (1976) 181: There was a lot of twisty trade came to the Metropole. [...] I’m not specially prejudiced against guys corning one another . . . hell, I can understand it.
1974		(con. 1945) E. Thompson Tattoo (1977) 275: He and his oldest cousin had cornholed each other when they were little.
1982		S. King Running Man in Bachman Books (1995) 557: I believe you referred to Area Governor Johnsbury as ‘a corn-holin’ sonofabitch’.
1989		C. Hiaasen Skin Tight 117: He tried to cornhole me yesterday.
1992		(con. 1910s) F.M. Davis Livin’ the Blues 36: Anal intercourse was ‘cornholing’.
1992		Randolph & Legman Ozark Folksongs and Folklore I 503: corn-hole, or corn-haul, to bugger, of unknown origin.
2000		C. Cook Robbers (2001) 53: I ain’t never been cornholed myself [...] It’s a record I aim to keep.
2006		T. Dorsey Big Bamboo 136: No cornholing, no tittie-fucks, pearl necklaces, muff diving or golden showers.
2013		J. Stahl Bad Sex on Speed 115: Jim Jones [...] was cornholing all the People’s Temple Guys.
2018		‘Aidan Truhen’ Price You Pay 192: [A] picture on all of their phone screensavers of a cartoon horse cornholing their logo.

2. in fig. use, to defeat, to victimize.

1953		‘Ed McBain’ Cop Hater 111: Haviland became a bull, a real bull. He had learned his lesson. He would never be cornholed again.
1974		C. Loken Come Monday Morning 155: If he hadn’t let that slimy bastard cornhole ’im with that policy he’d be clear right now.
2021		J. Ellroy Widespread Panic 3: I entrapped soiled celbrities and putzo politicos and cornholed them in Confidential.