Green’s Dictionary of Slang

1. a lesbian.

1773		Adulteress in E. Donoghue Passions between Women (1993) 5: Women with Women act the Manly part. And kiss and press each other to the heart. / Unnat’ral Crimes like these my Satire vex; I know a thousand Tommies ’mongst the Sex.
1781		A Sapphic Epistle in Norton (2006) 400: Miss Sappho [...] was the first Tommy the world has upon record.
1813		Holloway (printer) Vere Street Coterie 11: Many of these wretches are married; and frequently, when they are together, make their wives, who they call Tommies, topics of ridicule.

2. a male homosexual.

1999

(ref. to early 19C) G. Seal Lingo 114: The gay culture, long a clandestine network, by necessity developed a sophisticated little lingo for communication. [...] By the early 19th century the term tommy was being used.

3. (US) a prostitute, or promiscuous young woman.

1842		Nichols Wkly Arena (NY) 4 June) n.p.: The two following [songs] struck us as being particularly rich, rare, and racy: — the ‘Lovesick Tommy’ and the ‘Benighted Wren’.
1887		Lantern (N.O.) 21 May 3: Dey had tings all dere own way wid de Tommies.
1903		H. Hapgood Autobiog. of a Thief 126: In the afternoon I’d take in some variety show; or buy the ‘Tommy’ a present.
1913		B.T. Harvey ‘Word-List From The Northwest’ in DN IV:i 28: tommy, n. A girl. Also called [...] chippy.
1914		Jackson & Hellyer Vocab. Criminal Sl. 84: tommy [...] A prostitute.
1927		Lucille Bogan ‘Jim Tampa Blues’ 🎵 Hey, Jim Tampa, you treat your woman so mean / You treat your tommies like a woman you ain’t never seen.
1935		W. Smith Bessie Cotter 49: She’s on the square, anyway. That’s more’n you can say for some o’ these tommies.
1940		W.R. Burnett High Sierra in Four Novels (1984) 348: Get yourself a hot young tommy you can keep moving with.
1965		B. Jackson Get Your Ass in the Water (1974) 131: Now you might think me fickle, but it isn’t a dream, / when it comes to peachy looks this Tommy was a queen.