Green’s Dictionary of Slang

1. (US black) a derog. description of a fellow black whose opinions, attitudes and goals are taken from white society; thus Oreolized.

1969		in Current Sl. IV:3–4 (1970) 21: Oreo, n. A black who thinks like a white or tries to join white society. (Blacks on the outside but whites on the inside).
1972		R. Kahn Boys of Summer 401: ‘They’re too young to remember what I did, or they don’t care. I began to talk and some shouted “Oreo.” You know. The cookie that’s black outside and white underneath’.
1977		A. Brooke Last Toke 75: Ain’t seen you as riled as that since that jive inmate to the Tombs called y’all a Oreo cookie.
1978		A. Maupin Tales of the City (1984) 243: The sophisticated Miss D’orothea Wilson was the product of a lower-class interracial marriage. [...] She was, in short, an Oreo.
1989		(con. 1968) W.E. Merritt Where the Rivers Ran Backward 22: They go calling me Oreo and cutting my black ass to see how white I am inside.
1989		P. Benchley Lush 113: ‘You say it’s because we’re . . . we’re—’ ‘An Oreo cookie. You are a white, a card-carrying member of the master race and I am of the Negro persuasion.’.
1994		N. McCall Makes Me Wanna Holler (1995) 335: They would identify me [...] as an Uncle Tom, an Oreo, the white man’s puppet.
2003		G. Tate Midnight Lightning 24: Selling hip Black rock to whites and the ’hood without making Blackfolk stare down their noses at they asses like they were alienated Oreos.
2017		D. Winslow The Force [ebook][T]he ‘community’ [...] see him either as a potential ally who should help them out, or as a traitor. An Uncle Tom, an Oreo .

2. in fig, non-racial use.

1985

O. Hawkins Chili 56: I saw her [...] as a kind of sexual oreo, female outside and inside and male on the inner side.

3. (orig. US gay, also Oreo sex) sex between two black men and a white man; sex between two black men and a white woman.

1999		Gaymart.com Queer Sl. in the Gay 90s 🌐 Oreo Sex – Sex between two black men and a white man.
1999		Roger’s Profanisaurus 3 in Viz 98 Oct. 21: oreo n. An inverse chocolate sandwich (qv).
2000		Ebonics Primer at www.dolemite.com 🌐 oreo Definition: [...] 2. when a white bitch is be gang banged by two black pimps.
2006		G. Malkani Londonstani (2007) 23: Din’t matter what you called them. Coconuts, Bounty bars, Oreo biscuits or any other food that was white on the inside.