Green’s Dictionary of Slang

cornhole n.

1. (orig. US) the anus, the rectum.

[Wkly Wisconsin (Milwaukee, WI) 25 May 2/3: ‘Corn Hole Johnny’ hails from Texas and his special fort is three-card monte.
[US]H.N. Cary Sl. of Venery.
[US]W. Burroughs Naked Lunch (1968) 258: They was ripe for the plucking forgot way back yonder in the corn hole.
[US]E. Thompson Garden of Sand (1981) 165: THE WHOLE FUCKING WORLD IS ONE BIG CORNHOLE !
[US]Frank Zappa ‘Broken Hearts are for Assholes’ 🎵 Cornhole.
[US]C. Goffard Snitch Jacket 24: A hobo after Gus Miller’s tender cornhole itself.

2. attrib. use of sense 1.

[US]E. Sanders [title] Bugger! An Anthology of Anal Erotic, Pound Cake Cornhole, Arse-Freak and Dreck Poems.
[US]T. Willocks Green River Rising 207: ‘He’s gone to kill himself some faggots,’ [...] ‘Those cornhole fuckers are dead.’.

3. (orig. US) anal intercourse; thus cornhole cowboy, cornhole artist, one who enjoys anal intercourse.

[US]T. Southern Blue Movie (1974) 115: ‘How’s about a quick cornhole?!?’ And he rushed against Sid’s great bottom with outthrust pelvis.
[US]E. Torres Q&A 88: Guy used to be the super in Roger’s building. Cornhole artist.
[UK]J. Morton Lowspeak.
[US]G. Indiana Rent Boy 86: The whole trip with Father Cornhole and my lawsuit.

4. a rustic, a peasant.

[US]W.T. Vollmann You Bright and Risen Angels (1988) 329: The country pumpkin-headed cornholes get some cheap sophistication.