Green’s Dictionary of Slang

1. male masturbation.

1890–1904		Farmer & Henley Sl. and Its Analogues.
1986		B. Hudson First Aus. Dict. Vulgarities and Obscenities n.p.: Fucking the fist. Masturbation.

2. (gay) the insertion of the hand (and sometimes forearm) into the anus of one’s partner for purposes of sexual stimulation [popular in the 1970s but latterly in decline through fears of injury and hence the possibility of spreading AIDS; also found in heterosexual and lesbian sex, where the orifice is the vagina].

1977		B. Judell ‘Sexual Anarchy’ in Blue Boy (Miami) Aug./Sept. in Jay & Young (1979) 135: The fuck bar seems to be reaching its high noon of popularity and notoriety [...] What goes on in such a place? [...] one can witness and experience cocksucking, regular and fist fucking, water sports, gang bangs, sadomasochism, beer slurping, gum chewing, masturbation, group sex.
1978		R. Price Ladies’ Man (1985) 224: A red handkerchief hung from his pocket [...] That guy’s into getting fist-fucked. Red is fist-fucking.
1986		B. Hudson First Aus. Dict. Vulgarities and Obscenities n.p.: Fucking the fist. Masturbation. Not to be confused with fist fucking, a form of anal intercourse.
1989		Kirk & Madsen After The Ball 305: The really jaded run rapidly through the milder versions [...] and graduate to whips, executioner’s masks, and fist-fucking.
1992		K. Lette Llama Parlour 43: We’ll graduate to jokes about paraplegics, pederasts and fist fuckin’.
2001		Dean & Lane Homosexuality and Psychoanalysis 378: The gay New York club The Mineshaft [was] legendary for its sexual extremism: I had never seen anything like it: fist fucking.
2009		R. Milward Ten Storey Love Song 49: The [book] with the fist-fucking and flowers.