Green’s Dictionary of Slang

1. to have sexual intercourse; to have anal intercourse.

c.1930		(con. late 19C) N. Kimball Amer. Madam (1981) 206: I’m a married man. I don’t stupp no shickas.
1958		(con. 1950) E. Frankel Band of Brothers 122: Smuck, puhtz, momser, shtup . . . I keep learnin’, Mel, I’ll be talkin’ Jewish right good.
1965		L. Bruce How to Talk Dirty 79: I had schtupped plenty of women, but I had never slept with one.
1974		J. Lahr Hot to Trot 183: He wanted to get you hot. He’d shtup a snake.
1978		R. Price Ladies’ Man (1985) 141: So when you’re schtupping with the old lady she’ll come like summer rain.
1987		R. Campbell Alice in La-La Land (1999) 119: So, all right, maybe you get a little tired of shtupping the same old cold cuts and poking the same old eclairs.
1997–2001		Online Sl. Dict. 🌐 schtupp v 1. to engage in coitus. (‘I wanted to schtupp her in the worst way.’).
1999		Guardian Saturday Rev. 5 June 9: An incongruous echo of Portnoy – ‘Me! ... shtupping their best girl!’ – has a similarly lazy air.
2001		(con. 1964–8) J. Ellroy Cold Six Thousand 241: ‘Suppose I want dark stuff?’ ‘You call Al at the chambermaids’ union. It’s good trim, if you don’t mind schtupping in a mop closet.’ [Ibid.] 522: Come on. I heard he was shtupping Ava Gardner.
2006		P. Carey Theft 95: I was shtupping her stupid.
2006		D. Winslow Winter of Frankie Machine (2007) 19: Why should i go to church [...] and listen to some priest who schtupps little boys lecture me on morality?
2021		J. Ellroy Widespread Panic 10: I shtupped Jack’s wife.

2. to destroy, to humiliate, to defeat [fig. use of sense 1].

1990

(con. early 1950s) J. Ellroy L.A. Confidential 450: No man on earth is capable of shtupping me like that.