Green’s Dictionary of Slang

of a man, to have sexual intercourse with.

1949		N. Algren Man with the Golden Arm 217: He was out stiffin’ some piece of trade.
1974		G.F. Newman You Flash Bastard 126: Terry Sneed had never been in love [...] he got erections and wanted to stiff women, that was all.
1988		(con. 1940s) C. Bram Hold Tight (1990) 156: You think I might stiff you? Again?
2003		A. Swofford Jarhead 69: I’m sure the hotel clerk likes telling his friends that the new girl he’s stiffing is a dumb jarhead’s girlfriend.