Green’s Dictionary of Slang

occupy v.

of a man, to have sexual intercourse; thus occupier n., the man himself .

1542		Udall (trans.) Erasmus’ Apophthegms (1564) Bk II 361: One [...] adulterer that occupied the wife of Marcus Crassus.
c.1591		‘Second Libel of Oxford’ in May & Bryson Verse Libel 377: Was she well occupide? how think you, / To leave in banks hir buttocks’ print?
1594		Gesta Grayorum in J. Nichols Progresses and Processions of Queen Elizabeth (1823) III 332: Heer’s waters to quench maidens fyres, / Here’s spiritts for old occupiers.
1598		Florio Worlde of Wordes n.p.: Fottuto, iaped, occupied [...] Fottisterij, baudie or vauting houses. Also occupyers or baudie fellowes.
1607		E. Sharpham Cupid’s Whirligig IV v: If your Husband alien (or put away your affection) let it be then lawfull for your foresaid husband, againe to receiue, and then to haue, hold, manure and occupie in statu quo prius.
c.1622		ballad in Wardroper (1969) 136: City wives, they say, / Do occupy by charter.
1656		R. Fletcher (trans.) Martiall his Epigrams XI No. 98 110: I can swive four times a night: But thee Once in four years I cannot occupie.
1662		Pepys Diary 7 May n.p.: In the late business of Chimney Money, when all occupiers were to pay, it was questioned whether women were under that name to pay; and somebody rose and said that they were not occupiers, but occupied.
1680		School of Venus (2004) 34: Occupying, is to stick a Prick into a Cunt, and Riggle your Arse will you Spend, and truly that word expresses it better than any other.
1683		Last Will and Testament of the Charter of London in Somers Tracts 8 393 : All the mannor of Moorfields, with all the wenches and bawdy houses thereunto belonging, with Mrs Cresswels for his immediate inheritance, to enjoy and occupy all from the bawd to the whore downward.
1719		in D’Urfey Pills to Purge Melancholy V 139: For Peggy is a bonny Lass, and grinds well her Mill, / For she will be Occupied when others they lay still.
1731		Beau’s Misc. 90: What’s that in which good Huswives take delight? / Which, tho’ it has no Legs, will stand up-right? [...] But by good Huswives rub’d before ’tis us’d, / That it may fitter for their Purpose-be, / When they the same to occupy are free.
c.1770		Joaks upon Joaks 10: Meeting in a field a poor beggar woman [...] His lordship had a great mind to occupy her.
c.1786		Grose Classical Dict. of the Vulgar Tongue ms. additions n.p.: Occupy, to Occupy a Woman, to have Carnal knowledge of her.
1788, 1796		Grose Classical Dict. of the Vulgar Tongue (2nd, 3rd edn).
1790		‘Bumper Allnight. Esquire’ Honest Fellow 44: I have a tenement to let, / [...] /I call it Sportsman’s Hall, sir / [...] /For what’s the use of such a thing, / If it’s not occupied, sir?
1811		Lex. Balatronicum.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.
1896		Farmer Vocabula Amatoria (1966) 117: Exercer. To copulate; ‘to occupy’.

In derivatives

occupying (n.)

an act of sexual intercourse.

1544		J. Bale Lord Cobham in Christmas Sel. Wks (1840) 12: Unspeakable filthiness of all fleshly occupying was then called priests’ chastity.
1598		Florio Worlde of Wordes n.p.: Fottitura, a iaping, a swiuing, a fucking, a sarding, an occupying.
1654		Proceedings before his Highness Councel concerning the Petitioners of the Isle of Ely against George Clapthorne Esqyure 27 Oct. 5: The said Anne Martin called him Puppily-foole, and said, the old Justice Clapthorne had offered her eighteen shillings for an occupying.

In compounds

occupying house (n.) [house n.¹ (1)]

a brothel.

1598

Florio Worlde of Wordes n.p.: Chiausterio, an occupying house, a bawdy house.