Green’s Dictionary of Slang

1. (also five-time, three-time) to deceive sexually.

1918		Hall & Niles One Man’s War (1929) 314: I told Luf about how little Yvonne had two-timed me.
1923		Alberta Hunter ‘Aggravatin’ Papa’ 🎵 Aggravating Papa, don’t try to two-time me!
1925		G.S. Schuyler Yellow Peril in Hatch & Hamalian Lost Plays of Harlem Renaissance (1996) 59: Ah, hah! So! Five timing me, eh?
1948		T. Thursday ‘Movie Stuff’ in Detective Story Apr. 🌐 A man’s a sucker to kill for a woman who two-times him.
1958		W. Motley Let No Man Write My Epitaph (1960) 305: ‘She’s been two-timing you,’ he said. ‘Me too.’.
1960		E. De Roo Big Rumble 102: ’Cause you been two-timin’. Big Tony wants to make sure you behave yourself from here on in.
1974		(con. 1960s) R. Price Wanderers 86: I had a girl-friend who was two-timin’ me. I dropped her like a hot potato.
1978		Jilted John ‘Jilted John’ 🎵 I don’t want to two-time you / So it’s the end for you and me.
1985		J. Wambaugh Secrets of Harry Bright (1986) 245: He mighta been real heartsick about his boyfriend two-timing him.
1998		G. Burn Happy Like Murderers 50: She confided her worries about two-timing Tony.
2000		Guardian Weekend 4 Mar. 69: She three-timed him with his mates Chazza and Jezza.
2005		B. Hare Urban Grimshaw 258: Urban had been two-timing Molly for quite a while with Teezer.
2014		J. Conley ‘Visitor at Copenhagen Street’ in ThugLit Jan. [ebook] I was obsessed over one thing: was Colin two-timing me.

2. (orig. US) to cheat, esp. to double-cross.

1926		Van Vechten Nigger Heaven 156: I don’t let anybody two-time me!
1937		P. Cheyney Dames Don’t Care (1960) 63: I am goin’ around [...] bustin’ guys wide open until somebody stops two-timin’ me an’ comes across with a spot of real honest-to-god truth.
1942		W. Pegler George Spelvin Chats 67: Have you been two-timing me, out holding down a job on me while I’m away?
1950		Goldin et al. DAUL 230/2: Two-time. Double-cross.

3. of a man, to start living with an absent man’s partner.

1931

Barbecue Bob’ ‘Ease it to Me Blues’ 🎵 When I find that aggravating papa that tried to two-time me / I know I spend a great long spell in the penitentiary.