Green’s Dictionary of Slang

(a) a prostitute [‘like that animal she covers her back with her tail’ (Grose, 1788)].

1602		Dekker Satiromastix IV ii: A Gentleman, or an honest Cittizen, shall not sit in your pennie-bench Theaters, with his Squirrell, by his side cracking nuttes.
1617		Davies of Hereford Wits Bedlam 187: Of Flauias paynting; and playing the Squirell [...] she goes (like a Countess) in her Vaile; So, (Squirrell-like) she’s couer’d with her Taile.
1635		H. Glapthorne Hollander I i: The three Squirrels in the towne.
1675		Head Nugae Venales 85: She [a whore] was like a Squirel [...] for she covers her whole Body with her Tail.
1693		Congreve Old Bachelor V iv: bell.: You have an opportunity now, madam, to revenge yourself upon Heartwell for affronting your squirrel. belin.: O, the filthy rude beast!
a.1704		N. Ward ‘The Infallible Predictor’ in Writings (1704) 352: Many Inns of Court Squirrels will be seen walking, who cover their Backs with their Tails, and have no other Business there than to crack a penniworth of Nuts.
1788, 1796		Grose Classical Dict. of the Vulgar Tongue (2nd, 3rd edn) n.p.: Squirrel. A prostitute: because she, like the animal, covers her back with her tail.
1790		Banquet of Wit 22: A gentleman speaking of Nancy Parsons, the famous courtezan, who always had an abundance of fine cloaths, said she was like a squirrel, ‘for she covered her back with her tail’.
1811		Lex. Balatronicum [as cit. 1788].
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.

(b) the vagina [the pubic ‘fur’; coined independently of sense 1a].

1701		N. Ward ‘A Walk to Islington’ in Writings (1704) 76: Another Chaste Damsel turn’d into a Lawrel, / To hinder Apollo from handling her Squirrel.
1787		R. Tyler Contrast II 2: I know how to play hunt the squirrel, but I can’t play anything with the girls; I am as good as married.
1989		H. Rawson Dict. of Invective (1991) 372: squirrel. A woman or her genitals.

(c) a woman, usu. as a sex object [coined independently of sense 1a].

1915		implied in squirrel food
1942		in Randolph & Legman Ozark Folksongs and Folklore (1992) II 769: Chase that rabbit, chase that squirrel, / Pay that fiddler and diddle that girl.
1975		G. Underwood ‘Razorback Sl.’ in AS L:1/2 67: squirrel n [...] 2: Girl (male use).
1989		H. Rawson Dict. of Invective (1991) 372: squirrel. A woman or her genitals.
2003		‘The Cooter Monologues’ at www.pinkhairedgirl.com 20 Jan. 🌐 Squirrel. There’s this scene in Bring It On where a rival football player says, ‘While you’re out here losing, your male cheerleaders are out there stealing all your squirrel.’.

(d) (US campus) the female pubic hair [coined independently of sense 1a].

1975

G. Underwood ‘Razorback Sl.’ in AS L:1/2 67: squirrel n 1: Vulva, female pubic hair (male use).

(a) (US) an eccentric person.

1911		T.A. Dorgan in Zwilling TAD Lex. (1993) 107: Half the world are squirrels and the other half are nuts.
1943		H.A. Smith Life in a Putty Knife Factory (1948) 46: I’ve seen some squirrels in my life, but you got ’em all beat.
1959		E. De Roo Go, Man, Go! 49: He kept thinking of the wild ride and called himself a god-damned yo-yo, a squirrel, a nut, a shot-rodder.
1961		(con. 1945) G. Forbes Goodbye to Some (1963) 71: He’s a real squirrel.
1977		C. McFadden Serial 84: Safe from his total squirrel of secretary.
1989		H. Rawson Dict. of Invective (1991) 372: A squirrel may be an odd person of either sex.

(b) a psychoanalyst.

1932

L.W. Merryweather ‘Argot of an Orphans’ Home’ in AS VII:6 403: squirrel, n. A psychologist or psychiatrist.

(c) (US) a stupid, shortsighted person.

1947

(con. 1944) J.H. Burns Gallery (1948) 73: He couldn’t bear to hear them jabbering at him, opaque to another reality more bitter than their own. They were enmeshed in their own tyranny of fact, insensitive to the dreadfulness of their own natures and to the position in which they happened to be – squirrels of fate in a slimy North African town, having the time of their lives.

(d) mental illness.

1944

J. Archibald ‘Skip Tracer Bullets’ in Popular Detective June 🌐 We’ll lock him up an’ let a dome expert examine him for squirrels, sister.

(e) (US campus) one who is slow on the uptake.

1970

Current Sl. IV:2.

(f) a mentally ill person, a psychopath.

1972		J. Wambaugh Blue Knight 285: That cat’s a squirrel [...] A lucky looney.
1981		J. Wambaugh Glitter Dome (1982) 152: All theirs because the squirrel is suddenly transformed into a dope dealer by an ‘anonymous informant’.
1991		D. Simon Homicide (1993) 584: Squirrel No. 1 [...] brain-dead and guilty.
2000		P. Cornwell Last Precinct 251: Some squirrel playing a sick joke.

(g) (US prison) a mentally ill prisoner.

2000

Texas Lawyer [journal] Gloss. of Texas Prison Sl. 8 Feb.: Squirrel — A mentally ill inmate.