Green’s Dictionary of Slang

1. to have sexual intercourse with, to work as a prostitute.

1778		in Weis & Pottle Boswell in Extremes (1971) 248: When we talk of pleasure, we mean sensual pleasure. When a man says he had pleasure with a woman, he does not mean conversation, but that he tailed her [OED].
1835		‘My Shickster Molly’ in Knowing Chaunter 43: I care not for pals tho’ they call me C. P., / ’Cause my shickster Molly goes tailing for me.
1870		in G. Legman Limerick (1953) 92: A convict once, out in Australia, / Said unto his turnkey, ‘I’ll tail yer.’ / But he said, ‘You be buggered, / You filthy old sluggard, / You’re forgetting as I am your gaoler.’.
1888–94		‘Walter’ My Secret Life (1966) II 317: Molly was astonished. She had never been tailed in that attitude before, I am sure.

2. to follow, to keep under (police) surveillance.

1847		[A. Harris] (con. 1820s) Settlers & Convicts 258: Thus it becomes neccessary to keep a man after them [i.e. cattle on the move] all day in the bush, till they settle, which is called ‘tailing them’.
1900–10		Stephens & O’Brien Materials for a Dict. of Aus. Sl. [unpub. ms.] 153: TAIL [...] to follow or spy upon, to keep under surveillance.
1911		L. Stone Jonah 132: Wot makes yer tail up after me?
1916		J. Lait ‘If a Party Meet a Party’ in Beef, Iron and Wine (1917) 97: He waits around till I get off and tails me on that car, and takes a seat acrost from me and gives me the all-over like he was gonna buy me or something.
1926		J. Black You Can’t Win (2000) 227: You ‘tail’ him to a genteel-looking place with a ‘private board’ sign in a downstairs window.
1930		Eve. Herald (Dublin) 9 Dec. 4/6: ‘Taill’ [sic] means that a crook is being watched by detectives.
1938		R. Chandler ‘Red Wind’ in Red Wind (1946) 29: I tailed him home from headquarters.
1946		Mezzrow & Wolfe Really the Blues 90: Zigzagging all around town to make sure we weren’t being tailed.
1955		B. Schulberg On the Waterfront (1964) 24: He spotted Sonny tailing him.
1968		N. Heard Howard Street 233: We’ve been tailin’ you ever since you left the hospital.
1979		G. Swarthout Skeletons 42: I was followed by a patrol car. I think they use ‘tailed’ in crappy crime novels.
1989		Pileggi & Scorsese Goodfellas [film script] 103: I’m sure we’re being tailed.
1997		C. Hiaasen Lucky You 137: He insisted he would have noticed somebody tailing them from the restaurant.
2006		C. Hiaasen Nature Girl 27: You want me to keep tailing your husband?
2010		L. Redhead Thrill City [ebook] ‘Maybe he was following me, saw you, and became fixated?’ [...] ‘That’s not a reason to have my family tailed’.
2013		T. Robinson Hard Bounce [ebook] ‘Figured we could tail Sid’.
2023		(con. 1962) J. Ellroy Enchanters 37: I tailed her [...] I came up behind.

3. to sodomise.

1870

Cythera’s Hymnal 78: A convict once, out in Australia, / Said unto his turnkey, ’I’ll tail yer’.

4. (Aus. gambling) in two-up, to throw a pair of tails.

1930		L. Lower Here’s Luck 44: ‘Two bob you tail ’em,’ said the milkman, casting a florin on the ground.
1966		J. Holledge Great Aust. Gamble 101: They [i.e. two pennies] hit the ground, and from every throat (if they are the same) comes the cry: ‘He’s headed ’em,’ or ‘He’s tailed ’em’.

5. to make the object of a criminal plan.

1934

J. Archibald ‘Time Will Tell’ in Phantom Detective Sept. 🌐 This ain’t a bank ya’ve got tailed, is it, Bat?