Green’s Dictionary of Slang

1. of a man, to have sexual intercourse.

1684		‘Poor Tom the Taylor’ in Ebsworth Roxburghe Ballads (1891) VII:2 473: You see poor Tommy of your trade, by [Rak]ing was abused.
1723		C. Walker Authentick Memoirs of Sally Salisbury 139: I took more Pleasure to be in the Appartment of a Female of the Game [...] I became so harden’d, as not to be asham’d, when I went upon the Rake, to leave Word, or a Note in my Door, to let any Body know at what Bawd’s, or Whore’s Lodgings I might be found.
c.1770		‘A New Song’ in Holloway & Black I (1975) 201: They call me the raking Jewel.
1786		Burns The Jolly Beggars in Works (1842) 12/2: A sailor rak’d her fore and aft, Behint the chicken cavie.

2. (also come upon the rake) to live in a rakish manner.

1700		Farquhar Constant Couple V iii: Now, madam, I’m a wit: I can rake now.
1714		A. Smith Lives of Most Noted Highway-men, etc. I 89: Jack Withers [...] having been all Night a raking in the Country.
1730		J. Miller Humours of Oxford II i: How many great Matches have I refus’d on your Account? – there was Mr. Rakewell of Queens [...] Mr. Soakpot of Maudlin.
1741		Secret Hist. of Betty Ireland (9 edn) 10: The raking Lords observing this, pursued their Resolution [to unmask every woman at the playhouse] no further.
1743		Proceedings Old Bailey 23 Feb. 100/2: Said I, How came she to get your Money? said he, I left it with her because I thought to be out all Night upon the Rake.
1748–49		Cleland Memoirs of a Woman of Pleasure (1985) 35: Having drunk too freely before he came upon the rake with some of his young companions.
1782		‘Poor Soldier’ in Ebsworth Roxburghe Ballads (1893) VII:1 92: So leave off your raking, and marry a wife.
1790		‘The Rambling Boy’ Rambling Boy 3: I am a raking Rambling Boy.
1800		Sporting Mag. Nov. XVII 90/2: Raking, which ruins most constitutions, / was far from spoiling his.
1822		‘Life in London’ in C. Hindley James Catnach (1878) 133: He’ll marry — and rake no more.
1832		Satirist (London) 21 Oct. 341/1: And Ned, our pet / [...] / Must leave off all his raking now.
1846		‘George Eliot’ in Cross Life I 147: We have been to town but once, and are saving all our strength to ‘rake’ with you .
1886		M.E. Braddon Mohawks II 211: ‘What have you been doing with yourself, Jack?’ ‘Raking, Herrick, raking! A long night at Vauxhall with Lady Polwhele and her crew, a debauche of champagne and minced chicken.’.
1893		Aberdeen Eve. Express 21 Mar 3/2: One day, taking an early stroll in mufti, he saw three or four pirates raking about.

3. in weak use of sense 2, to play in the streets as a child.

1961

(con. WW2) R. Poole London E1 (2012) 98: ’E stopped rakin’ round the streets with the other kids.