Green’s Dictionary of Slang

(orig. US) duplicitous, esp. in a sexual context.

1925		Rosa Henderson ‘It Takes a Two-Time Papa’ 🎵 It was just the other day, / I heard a red-hot mama say: / It takes a two-time papa / To make a one-time mama mad.
1928		Bessie Smith ‘Devil’s Gonna Git You’ 🎵 I don’t want no two-time stuff / From my regular man.
1936		Casey Bill Weldon [song title] Two-Timin’ Woman.
1939		P. Cheyney Don’t Get Me Wrong (1956) 112: I am just about sick of these cheap, chisellin’, two-timin’ rotten rats of lawyers.
1941		‘Digg Mee’ ‘Observation Post’ in N.Y. Age 15 Mar. 9/6: That’s a shame, to think you can beat the ‘two-time’ game.
1948		(con. 1944) N. Mailer Naked and Dead 120: I should have known better, marrying a two-timing bitch like that.
1952		B. Appel Plunder (2005) 270: A straight GI girl and no fancy two-timing mestiza like Serafina.
1965		C. Himes Cotton Comes to Harlem (1967) 185: I just want to get something out of that two-timing mother-raper.
1987		‘Joe Bob Briggs’ Joe Bob Goes to the Drive-In 44: The only things I could make out were [...] ‘two-timing s.o.b.’ (referring to her twisted imagination’s guess about what Cherry Dilday and I were planning to do that night).
1999		Observer Mag. 15 Aug. 19: Stella works for her lawyer boyfriend, a two-timing bastard.
2001		N. Barlay Hooky Gear 239: If it aint Arno workin me an it aint Uncle workin a 2-timin bitch.