Green’s Dictionary of Slang

1. a derog. term for a black person.

1901		W.A. Sun. Times (Perth) 21 July 1/1: The wife of a local nouveaux riches has lately developed a strong weakness for chocolate [...] the colored sweetmeat in this instance is an attractive Cingalese cook.
1913		Sport (Adelaide) 15 Mar. 12/1: They Say [...] That Ranji is not dark enough to be called Nigger and is not white enough to be called Snowflake, so they have christened him Chocolates.
1916		I.A. Williams diary 28 Oct. 🌐 A concert party by the name of ‘Chocolates’ gave us a very fine concert this evening.
1924		Amer. Mercury Feb. 130/1: I wish I was black like you [...] No you don’t. Dey’d call you Crow, den—or Chocolate—or Smoke [DA].
1934		J. Franklyn This Gutter Life 15: His last fight was with ‘Young Chocolate Brown,’ the big nigger from Kansas.
1949		‘Swasarnt Nerf’ et al. Gay Girl’s Guide 5: chocolate: A negro.
1978		Maledicta II:1+2 (Summer/Winter) 154: Chocolate Any black person, but especially a woman or homosexual. Used as often as an endearment as for derogatory purposes, by both blacks and whites.
1983		I.L. Allen Lang. of Ethnic Conflict 46: Color Allusions, Other than ‘Black’ and ‘Negro’: chocolate [chokker and chokko are possible variants].

2. (also chocolate brown) as used by a black person, thus not derog.

1926		Van Vechten Nigger Heaven 13: Blues, smokes, dinges, charcoals, chocolate browns, shines, and jigs.
1978		see sense 1.
2001		(con. 1981) A. Wheatle East of Acre Lane 76: ’Pon de front line is pure undercover beastman, to blowoh. An’ you can’t tell de coconuts from de pure chocolate, man.
2017		Harlem Spartans ‘Grip & Ride’ 🎵 She, brown brown and she cute Darlin' you can be a spartan too / Ay, chocolate throwing up K's / Got, caramels doing it too.

3. the anus, used in the context of defecation and homosexuality.

1972		B. Rodgers Queens’ Vernacular 89: anal intercourse [...] stir somebody’s chocolate (late ’60s).
1993		B. Moore Lex. of Cadet Lang. 285: punch a hole through the chocolate to engage in homosexual or heterosexual anal intercourse.

4. (S.Afr. black) a 20-rand note.

1984

M. Mthethwa in Frontline July 28 n.p.: Their pockets and wallets and purses are thickly lined with stacks of ‘cabbages’ and ‘chocolates’ ten and twenty-rand banknotes.

5. as black-to-black term of address.

2004

N. Kelley ‘The Code’ in Brooklyn Noir 183: See you in a few minutes, chocolate.