Green’s Dictionary of Slang

brown eye n.

1. (also little brown eyeball) the anus.

[US] ‘Ball of the Freaks’ in D. Wepman et al. Life (1976) 111: The action was a flash, her cunt opened like a gash, / And her brown-eye lost all its feeling.
[US]F. Hilaire Thanatos 245: They crammed a finger in everybody’s ass—now that’s a no-no, so they just look. But they can’t see nothing except a brown eye.
[US]R.A. Wilson Playboy’s Book of Forbidden Words 161: Little Brown Eyeball. The anus.
[Aus]R. Aven-Bray Ridgey-Didge Oz Jack Lang 19: Brown Eye Anus.
[US](con. 1970s) G. Pelecanos King Suckerman (1998) 87: There wasn’t no pussy in the world tighter than the brown eye on a young boy.
‘UK Snowy’ ‘Christmas Blackmail’ at www.asstr.org 🌐 I persuaded her to take it up the arse [...] A virgin twelve year old brown eye to explore and then plunder is an incredible experience and she took to it superbly.

2. anal intercourse.

[US]E. Folb Runnin’ Down Some Lines 159: Too many woman walkin’ aroun’ to be usin’ brown eye.
[US](con. 1940s) C. Bram Hold Tight (1990) 73: That big old stevedore [...] settles for nothing less than the deep, brown eye.
[US]N. McCall Makes Me Wanna Holler (1995) 195: Hey, baby, when you gonna gimme that brown-eye?
[US]Mad mag. Sept. 19: How about a shot of Captain Browneye?
[US]T. Pluck Bad Boy Boogie [ebook] ‘So you’re a warrior, not some punk who can’t admit he loves the brown-eye?’.
[US]J. Ellroy Widespread Panic 185: ‘He’s got Jimmy Dean for the brown eye and Natalie Wood on the distaff side. Natalie’s sixteen’.

In phrases

do a brown eye (v.) (also brown-eye, chuck a brown eye)

(Aus./N.Z.) to drop one’s trousers and underwear and reveal one’s naked buttocks (and anus) to anyone who is watching, a mainly juv. prank.

Tharunka (Kensington, NSW) 31 Mar. 3/1: The last time I saw a guy chuck a brown eye was during a law Revue rehearsal about thee years ago. I laughed myself stupid.
[Aus]C. Bowles G’DAY 109: He finally gets up on the bridal table, drops his daks, and chucks a browneye.
[NZ]B. Payne Staunch 90: I turned round, dropped my trousers and [...] bent over and gave her the ‘brown-eye’.
[Aus]Sydney Morn. Herald Review 15 Oct. 137/6: There aren’t too many magic moments on TV [...] unless you count Bart Simpson chucking a browneye at the whole of Australia.
[Aus](con. 1964-65) B. Thorpe Sex and Thugs and Rock ’n’ Roll 71: ‘I brown-eyed a bunch of schoolgirls from the bus’.
[NZ]A. Duff Jake’s Long Shadow 61: Everyone was [...] teasing the birthday boy, Errol, to make a speech, or pull his trousers [...] do a brown eye.
[Aus]Aus. Lang. at Aussie-Info.com 🌐 brown-eye – to show one’s bottom, mooning.
[NZ]McGill Reed Dict. of N.Z. Sl. 35: brown-eye, to An unattractively active verb meaning to expose the anus. ANZ.
do the brown eye express (v.)

(US) to sodomize.

[US]J. Lansdale Bad Chili 197: This boy, Custer, he come down here and got in with boys like to do the brown-eye express.
get some brown eye (v.)

(US) to sodomize.

[US]E. Folb Urban Black Argot 139: Get Some Eye / Brown Eye to have anal intercourse, particularly with another male.
[US]E. Folb Runnin’ Down Some Lines 240: get some brown/tight eye Engage in anal intercourse with another male.