Green’s Dictionary of Slang

1. a woman; usu. a feminist or an intellectual.

1804		Sporting Mag. May XXIV 166/1: And young shemale; in a bed-room locked her / Alone mit me. / I that have got a vife.
1826		letter in Duberman ‘Writhing Bedfellows’ in Journal Homosexuality (1980/81) VI Fall/Winter 88: You are [...] braying, like an ass, at every she-male you can discover.
1837		York Herald (Yorks.) 4 Nov. 4/1: [from Claremeont (NH) Eagle] ‘Corzitz a shemale’ [...] ‘Why, Corzitz got Miss Soury on the norf, Louisia Ann on the souf, Mrs Sippy [etc.].
1843		Gleaner (Manchester, NH) 1 Apr. n.p.: That damsel [...] I mean the she-male that stops at No. 50 Broadway.
1849		London Dly News 5 Nov. 2/5: A most awkwardly dressed she-male was observed straddling through Wootonbridge [...] the supposed damsel turned out to be one of the Parkhurst Prison youths, who had fitted himself out with the stolen petticoats.
1856		in Botkin Treasury Amer. Folklore (1944) I 8: Davy Crockett’s hand would be sure to shake if his iron was pointed within a hundred mile of a *shemale.
1866		T.J. Dimsdale Vigilantes of Montana 69: Blue Stockings, Bloomers, and strong-minded she-males.
1886		S.W. Mitchell Roland Blake 261: Ther’s a heap of nat’ral histry in women. Chiefly ther’s two kinds [...] Ther’s females and shemales.
1896		‘’Arry on Blues and Bluestockings’ in Punch 21 Mar. 135/2: If shemales git sprinting away on their own, we mayn’t be in the ’unt.
1896		Riverina Recorder (Moulamein, NSW) 17 June 2/4: [A] lady and gentleman had a fight [...] the she-male came off best with the aid of a hammer.
1902		Bulletin (Sydney) 30 Oct. 12/3: The primitive nature of the crematorium made the spectacle a most revolting one, on which, nevertheless, about a score of Australian shemales feasted their eyes for a couple of hours – though even the Hindus themselves cleared out during the process.
1906		S. Ford Shorty McCabe 199: Not that I’m followin’ the she-male protectin’ business regular.
1909		H. Lawson ‘The Song of What Do You Think’ in Roderick (1967–9) II 282: The hemale and shemale, sash-wearing old female and daring young new-girly story.
1911		Vancouver Dly World (BC) 30 Nov. 10/3: The she-male of the species is less rabid than the he.
1915		Morn. Call (Allentown, PA) 16 June n.p.: Every she-mail or maybe he-male waring linen hare ribbons will have to pae von zent [sic].
1926		Wood & Goddard Dict. Amer. Sl. 20: girlie. A shemale; a girl.
1929		E. Caldwell Bastard (1963) 40: Why ain’t you asking questions about getting out of here instead of fooling with the shemale?
1936		L.A. Times 20 May 24/7: Modern woman is becoming what might be called the she-male of the species. She hasn’t ‘usurped’ the prerogatives of man, but wisely helped herelf to those he wasn’t using.
1943		R.L. Bellem ‘Dead Man’s Shakedown’ in Dan Turner Detective Mar. 🌐 Thirty-seven silly shemales got trampled in the crush at his funeral; and even now, veiled wrens put posies on his grave almost daily.
1967		J. Wynnum I’m a Jack, All Right 11: ‘Male or female — do you recollect?’ asked Ginger. ‘A shemale,’ Tosh told him.
1980		Barltrop & Wolveridge Muvver Tongue 67: Adult examples are ‘she-male’ for female.

2. a female transvestite.

1842

Whip (N.Y.) 30 July 2/4: That infamous strumpet Hal Grandy [...] thinks nothing of Promenading Broadway in open day in men’s apparel. [...] We would give the world to meet her in the street in any other appearance than that of a she-male.

3. a male homosexual or transvestite.

1979		Maledicta III:2 217: Outraged machismo flings pansy, nancy, boy-lover, maneater, she-male, fairy, faggot and fruit (UK fruiter), even seedless fruit.
1987		personal ad, adult bookstore Murray & Murrell Lang. Sadomasochism (1989) 121: SWM wants to meet future live-in slave , male, bi, TV, she males only.
1990		S. Morgan Homeboy 14: Like most shemales on the Strip Oblivia’s forte was B-drinking.
2001		J. Stahl Plainclothes Naked (2002) 43: The doctor believed he was being popped for shopping photos of she-males to fetishists on the Net.
2013		J. Stahl Bad Sex on Speed 30: A plus-size ironic she-male busy not eating her Belgian waffles [...] Plus-size Trannypants cannot stop talking.

4. (US gay) a lesbian.

1972		B. Rodgers Queens’ Vernacular 70: any gay woman [...] she-male (hetero sl).
2008		Asbury Park Press (NJ) 17 Oct. 61/10: [advert] Adorable She-Male Babe.

5. (US) a male-to-female transgender person having male genitalia.

1987		personal ad, restroom Murray & Murrell Lang. Sadomasochism (1989) 121: I want your meat and your boobs, she-males.
2021		H. Joyce Trans 55: This is a relatively common male sexual taste (as evident from the number of ‘shemales’ on Pornhub).