Green’s Dictionary of Slang

Cupid n.

1. a nickname for an ugly blind man [Cupid, as the god of love, is trad. blind].

[UK]Grose Classical Dict. of the Vulgar Tongue n.p.: Cupid, blind Cupid, a jeering name for an ugly blind man: Cupid, the god of love, being frequently painted blind.

2. a pimp who lives with his prostitute [ironic use; the relationship is so rarely affectionate].

[UK]Farmer & Henley Sl. and Its Analogues.

Proper name in slang uses

In compounds

Cupid’s alley (n.)

the vagina.

[UK]Farmer & Henley Sl. and Its Analogues.
[UK]Farmer Vocabula Amatoria (1966) 251: Terrier, m. The female pudendum; ‘Cupid’s alley’.
[US]Maledicta IV:2 (Winter) 185: Common examples [of sexual ‘addresses’] include Cockshire, Cock Inn, Cupid’s Alley, Hairyfordshire, Crown and Feathers, Shooter’s Hill, Mount Pleasant, Love Lane, etc.
Cupid’s battering ram (n.)

the penis.

[UK]Peeping Tom (London) 12 48/3: [advert] the wanton warbler — Cupid’s Battering Ram.
[UK] ‘Sub-Umbra, or Sport among the She-Noodles’ in Pearl 6 Dec. 2: The red head of ‘Cupid’s Battering Ram’ was now brought to the charge.
[Scot]J.C. Reddie Amatory Experiences of a Surgeon 21: The continued resurrections of Cupid’s battering ram, which she [...] assured me was a perfect phoenix of its kind.
Cupid’s cloister (n.) (also Cupid’s feast, ...furrow, ...grotto, warehouse of Cupid)

the vagina.

[UK]Character of a Town-Miss in C. Hindley Old Bk Collector’s Misc. 7: Her upper Parts are the shop of Cupid, and those below, his Warehouse.
[UK] ‘The Resolution’ in Playford Pills to Purge Melancholy II 119: But he that with unspotted Breast, / Bears Love as pure as Snow, / Shall be my Guest at Cupid’s Feast, / And let all others go.
[[UK]Harris’s List of Covent-Garden Ladies 59: A pair of dark blue eyes [...] invite the blind coral headed boy into her cloister of teeming joys].
[UK]Harris’s List of Covent-Garden Ladies 93: The pleasing Mount of Venus [...] which twining round the ruby portals of Cupid’s grotto forms a delightful bed for the root of the tree of life.
[UK]C. Deveureux Venus in India I 97: Finding her waistband loosened, it had explored the sweet pastures of her silvery belly, and crossing the rough surface grass of the mount of Venus. As my fingers pressed in Cupid’s furrow, the lovely little clitoris, ever on the watch, had sprung up to salute it with a moist and eager kiss.
[UK]Farmer Vocabula Amatoria (1966) 67: Cloître, m. The female pudendum; ‘the cloister’. [Ibid.] 79: Corridor d’amour, m. The female pudendum; ‘Cupid’s cloister’.
[US]Maledicta IV:2 (Winter) 182: Occasionally, the colloquialism acknowledges the functions of the part, as is seen with Cupid’s furrow.
Cupid’s coal-hole (n.)

the vagina.

[UK]Harris’s List of Covent-Garden Ladies 66: Her lovely half globes of nature [...] elevate themselves in a very pleasing manner, and tell the gazer in very plain terms the state of Cupid’s cole hole, whose embers are now sufficiently warmed to admit the red-headed torch.
[UK]Bacchanalian Mag. 26: Original and selected Toasts and sentiments [...] Cupid’s Coal-Hole.
Cupid’s kettledrums (n.) (also kettledrums, love’s kettledrums)

the female breasts.

[Scot] ‘Miss Peggy Alexander’ in Ranger’s Impartial List of the Ladies of Pleasure in Edinburgh n.p.: And when she’s in action, she heaves her little Cupid’s kettle-drums with great agility.
[UK]Grose Classical Dict. of the Vulgar Tongue ms. additions n.p.: Kettle Drums, or Loves Kettle Drums, a Womans Breasts.
[UK]Grose Classical Dict. of the Vulgar Tongue (2nd, 3rd edn) n.p.: Kettledrums. Cupid’s kettle drums; a woman’s breasts, called by sailors chest and bedding.
[UK]‘Toy’ in Hilaria 96: A pair of bubbies bolted out, / God Cupid’s kettledrums, sir.
[UK]Lex. Balatronicum [as cit. 1788].
[UK]Egan Grose’s Classical Dict. of the Vulgar Tongue [as cit. 1788].
Cupid’s measles (n.)

(US) secondary syphilis.

[US]B. Schulberg Harder They Fall (1971) 32: A full set of spirochaete pallida, known to the world as syphilis and to the trade as Cupid’s measles.
[UK](con. 1940s) G. Morrill Dark Sea Running 186: I started getting pains in my groin. ‘Cupid’s measles,’ said the Steward.
British Journal Sexual Medicine 24:4: (July–Aug.) ‘Lock hospitals’ were imported to India from England, where they had begun in the 18th century. [...] The inmates were female prostitutes suffering from ‘Cupid’s measles’.
[US]Allan & Burridge Forbidden Words 71: Cupid’s measles is slang for treponemal disease or syphilis.
Cupid’s nest (n.)

the female genitals.

[UK]‘The Charming Fair’ in Out-and-Outer in Spedding & Watt (eds) Bawdy Songbooks (2011) IV 147: The gentle zephyrs throug the tress / Had blow her coats above her knees; / When sly young Hodge, quite full of zest, / Behind a tree spied Cupid’s nest.
Cupid’s pesthouse (n.)

a brothel.

[UK]Life and Death of Damaris Page 1: [She] was most notably famous for keeping a house of, what shall I call it, for it had divers names, some called it the Seamans whirlpool, others Venus Bower, Cupids Pest-house, the Chyrurgions friend, the Hectors Office, a Vaulting-School, the amorous Chace, a Brothel, a Stew, the huck-strings Accademy, the hole in the Wall, &c.
Cupid’s pit (n.)

the vagina.

[UK]‘She’s Just the Girl’ in Flash Olio in Spedding & Watt (eds) Bawdy Songbooks (2011) III 191: I burning and raging wi’ passion / You’ve shoved I in Coopid’s pit up t[o] the eyes.
Cupid’s spear (n.)

the penis.

Letters from Laura & Eveline 6: Arthur who I [...] guessed would be formidably armed with a Cupid’s spear with the very ominous bunch in his trousers.
Cupid’s tennis-balls (n.)

the female breasts.

[UK]Belle’s Stratagem 67: Letitia: Oh!— Doricourt: Why do you sigh? — Why do you so heave those tennis-balls of Cupid?

In phrases

take a turn in Cupid’s alley (v.) (also take a turn in Cupid’s corner and hair court)

to have sexual intercourse.

[UK]Farmer & Henley Sl. and Its Analogues.