cheeks, n.¹ — Green’s Dictionary of Slang

cheeks n.¹

[there is a single citation in 1660, the term is then lost (at least from print) until Jon Bee in 1823 and only resurfaces again in James Joyce’s Ulysses (1922); however, the phrase blind cheeks under blind adj.¹ offers citations meaning buttocks for the whole of the 17C, 18C and 19C; also note 18C citations at ask cheeks near Cunnyborough ]

the posterior, the buttocks.

1607		implied in blind cheeks under blind adj.¹
1660		Wandring Whore II 13: A third laughing at the large pair of cheeks and haunches she hath got.
1823		‘Jon Bee’ Dict. of the Turf, the Ring, the Chase, etc.
c.1867		Rosa Fielding 109: [S]he was not a little startled by feeling [...] a hot kiss pressed upon one of the cheeks of her bum [Simes:DLSS].
1879		Pearl Oct. 128: [H]olding the cheeks of his bottom I moved him backward and forward, and made him fuck me in my mouth.
1881		Sins of Cities of the Plains 40: [H]e at once presented his prick to Boulton[’s] fundament, as he held the two cheeks of his pretty arse open with his hands [Simes:DLSS].
1890		Laura Middleton 39: .I made the cheeks of my bottom close round the head of the intruder so as to produce a most delicious compression on it [Simes:DLSS].
c.1900		‘Ramrod’ My Lustful Advent 41: [I]t was not till he actually put his tool between the cheeks that I realised his hideous design. I was going to be buggered! [Simes:DLSS].
1922		Joyce Ulysses 91: Shift stuck between the cheeks behind.
1938		J. O’Hara Hope of Heaven 63: ‘I think I’ll go right out and paddle those little round cheeks of yours, Miss Bronson’.
1962		(con. WWII) J.O. Killens And Then We Heard The Thunder (1964) 201: All right soldier, bend over and spread your cheeks. [Ibid.] 356: She wet a cheek of his bashful backside and let him have the needle tenderly.
1967		F. Salas Tattoo the Wicked Cross (1981) 15: Bend over and spread your cheeks.
1975		J. Wambaugh Choirboys (1976) 63: Bend over and spread your cheeks.
1988		H. Max Gay (S)language.
1989–2003		R.O. Scott Gay Sl. Dict. 🌐.
1993		S. King Dolores Claiborne 9: No high-steppin kitty like Vera Kiss-My-Back-Cheeks Donovan.
1998		J. O’Connor Salesman 276: Together again, Homer. Like the cheeks of me arse.
1999		L. Gould Shagadelically Speaking 60: heinie, butt; bum; [...] seat; cheeks.
2010		N. Drinnan Rare Bird of Truth 374: He looked at the gentle peach of Gulliver’s cheeks, the irresistible, sloppy jauntiness of his outfit [Simes:DLSS].

In phrases

ask cheeks near Cunnyborough

a woman-only phr., equivalent to ask my...! excl.

1785, 1788, 1796		Grose Classical Dict. of the Vulgar Tongue n.p.: Cheeks, ask cheeks near cunnyborough, the repartee of a St. Giles’s fair one, who bids you ask her backside, anglice her a—se.
c.1786		Grose Classical Dict. of the Vulgar Tongue ms. additions n.p.: [added to 1785 def.] A like pun is current in France. Any one asking the Road & Distance to Macon a City near Lyons would be answered by a French Lady of easy virtue Mettez votre nez dans mon cul & vous serrez dans les Faubourgs .
1811		Lex. Balatronicum.

beat cheeks (v.) [var. on beat ass v.]

(US) to leave (at speed).

1990

S. Morgan Homeboy 115: C.C. asked what she was going to do. ‘Beat cheeks down the blacktop.’.

powder someone’s cheeks (v.)

(US gay) to have anal intercourse.

1972		B. Rodgers Queens’ Vernacular.
1989–2003		R.O. Scott Gay Sl. Dict. 🌐 anal intercourse: [...] Syn: powder someone’s cheeks.

cheeks n.1

In phrases

cheeks n.¹