Green’s Dictionary of Slang

1. to imprison [caboose n. (1c)].

1880

in M. Lewis Mining Frontier (1967) 132: I can caboose the whole durn lot under Order No. 6.

2. to sodomize [caboose n. (2a)].

2001

J. Stahl Plainclothes Naked (2002) 90: I got caboosed by some black Twink with a button nose.