Green’s Dictionary of Slang

1. (US gay) a sexual partner who performs badly or whose anus is not as tight as it once was.

1972

B. Rodgers Queens’ Vernacular 99: one whose anus is no longer tight. Syn: hobo-sexual (camp). [Ibid.] 107: hobo-sexual sex partner whose performance was inadequate.

2. a person who enjoys regular casual sex; thus hobosex, sex with a number of strangers in a short period of time.

2000		R.J. Arobateau [title] Hobo Sex.
2002		D. Archer Parking Magic 🌐 Listen up. Every hobosexual in town cannot be William Burroughs or the whole outsider concept is down the sewer, okay.