Green’s Dictionary of Slang

1. (orig. US) weak or effeminate.

1882		Ft. Wayne Daily Gazette (IN) 2 Nov. 4/5: It makes me sick to see a man with a bracelet on his wrist. Only once have I been made to endure the nauseous sight. [...] The offender was a pretty, sissy young fellow [...] He had no idea of being ashamed of the femininity which he was displaying, but repeatedly rested his head on his hand in a way to exhibit the bracelet.
1890		Sporting Times 12 Apr. 2/1: The entertainment was of so calm and sissyish a nature.
1891		Harper’s Mag. Aug. 485/2: [He] sat near me, deep in conversation with a young gentleman with sissy whiskers [DA].
1893		N.Y. Mercury May in Ware (1909) 224/2: Sissy men in Society. – Powdered, painted and laced. They swarm at afternoon teas. Of late, says a London writer, a certain type of man has become protuberant – a languid, weak-kneed, vain, and lazy specimen of humanity who has literally no redeeming points that can be discovered, and who yet gives himself all the airs of one to whom the universe ought to do unquestioning homage.
1905		J.C. Lincoln Partners of the Tide 78: To be seen with girls was not so ‘sissified’ in his mind as it used to be.
1916		R. Service ‘The Revelation’ Rhymes of a Red Cross Man 128: But when we go back to our Sissy jobs,—oh, what are we going to do?
1923		H.C. Witwer Fighting Blood 238: He’s going to try and make Rags Dempster’s father pay back the ten thousand his sissy son got away from me.
1924		C.J. Dennis ‘Narcissus’ in Rose of Spadgers 158: I s’pose ’e got the cissy part becoz / ’Is ways was womanish.
1928		C. McKay Home to Harlem 117: A hefty-looking one like him, always acting so nice and proper. I almost thought he was getting sissy. But he’s a ma-an all right. [Ibid.] 249: Real men don’t sit in a saloon here as they do at home. I suppose it would be sissified.
1938		W. Winchell On Broadway 21 Mar. [synd. col.] It [i.e. a drink] sounds sissyish as anything, but they say it’s a he-man’s drink in summer.
1938		ad. in Double-Action Gang June 🌐 Sissy Stuff? You Think Western Love Story Is Sissy Stuff? Don’t Be Silly.
1941		B. Schulberg What Makes Sammy Run? (1992) 117: Like they say in sissy schools. No fair! For Chri’ssake, grow up.
1941		A. Gurney Bluey & Curley 8 May [synd. cartoon strip] Tossin’ pennies is a flamin’ cissie game.
1942		C.R. Bond 25 Jan. in A Flying Tiger’s Diary (1984) 81: My first impression is that they are sissified dainties.
1945		Look (ad. for Ex-Lax) 18 Sept. 77: Sulking is often a child’s way of avoiding something unpleasant – like the ‘sissy’ laxative some parents give their children.
1946		(con. 1910s) J. Thompson Heed the Thunder (1994) 65: What you afraid of a hiding for, you sissy bastard?
1947		Illus. 15 Mar. 19: What had gone on so far was just cissy stuff.
a.1948		(con. early 1930s) C. McKay Harlem Glory (1990) 63: I was becoming like a cheap sissified sweetback.
1948		C. Day Lewis Otterbury Incident 40: They’re windy! [...] Yellow Ted and his sissy-gang.
1949		L. Glassop Lucky Palmer 152: I haven’t got any [i.e. evening clothes]. Never could get around to buying any. Always seemed kind of cissy to me.
1950		Time 24 Apr. 44/1: James J. (‘Big Jim’) Jeffries [...] observed that the fight game has become so sissified that ‘I’d rather see a wrestling match’ [DA].
1957		G. Kersh Fowlers End (2001) 169: I think pink is a sissy colour.
1958		(con. 1940s) B. Behan Borstal Boy 361: Shackleton smiled and [...] said it was a cissy position.
1958		Willans & Searle Complete Molesworth (1985) 36: Poetry is sissy stuff that rhymes.
1960		(con. c.1928) D. Holman-Hunt My Grandmothers and I (1987) 158: I never liked those cissy ringlets.
1960		Mad mag. June 38: So he could look like a man, not a sissy star, walking around with a tie and a nice clean suit.
1962		Mad mag. Sept. 9: Everybody in this town is a yellow, chicken-livered, sissified fink!
1962		K. Waterhouse There is a Happy Land (1964) 19: I didn’t read the Rainbow any more, too blinking cissy.
1965		K. Marlowe Mr Madam (1967) 31: I just knew that whenever anyone said anything about a sissy or being sissified they meant me!
1969		P. Theroux Murder in Mount Holly (1999) 36: It wouldn’t be a sissy novel either. It would be a big lusty novel.
1974		C. Loken Come Monday Morning 18: Actin’ like a big sissy sucktittie ever’time she drives in the yard!
1977		E. Bunker Animal Factory 53: Someone had told him that some would think a part was sissified.
1977		Rolling Stone 22 Sept. 52: People would laugh at his sideburns and his pink coat and call him sissy.
1981		J. Wambaugh Glitter Dome (1982) 215: It made them nervous to see all the sissy punches and flabby slaps.
1989		Beano Comic Library No. 176 21: I say, Walter, old softy, isn’t it a bit cissy to have a baby-sitter at your age?
1993		K. Lette Foetal Attraction (1994) 164: A general anaesthetic was considered too sissy.
1999		Indep. Education 8 July 2: My research has shown that ‘sissy’ boys are highly likely to be bullied in the school playgrounds.
2000		Indep. Rev. 14 Aug. 7: Peace? How sissyish!
2004		J. Ellroy ‘Jungletown Jihad’ in Destination: Morgue! (2004) 365: No rapid right of writs and redress here [...] no sissy civil rights.
2012		D. O’Donnell Locked Ward (2013) 5: I had offered to tie it back in a ponytail — still something of a sissy novelty in those days. That was jessie enough.
2015		L. Berney Long & Faraway Gone [ebook] He wasn’t some small sissy guy either.

2. homosexual; pertaining to the world of male homosexuality; thus sissification n., the act of making something homosexual.

1928		E. O’Neill letter 15 Sept. in Bogard & Bryer Sel. Letters (1988) 317: Your article on the sissification of the stage handed me a large and satisfactory chuckle.
c.1930		(ref. to 1898) N. Kimball Amer. Madam (1981) 261: Old Sugar Mary said I lost trade by not going in for the sissy byplay.
1948		Kerouac letter 3 Oct. in Charters I (1995) 167: This suggests queerness ... it is too ‘sissy’.
1964		A. Baraka Slave in Three Negro Plays (1969) Act I: When we used to chase that kind of frail sissy-punk down Raymond Boulevard.
1969		‘Iceberg Slim’ Pimp 108: I had been satisfied with the shallow rundown from that ‘sissy’ bar keep.
1981		J. Wambaugh Glitter Dome (1982) 165: They have me in the sissy tank with all the other gay people.

3. easy, simple.

1946

G. Gibson Enemy Coast Ahead (1955) 103: We are all going to Lorient to-night [...] to lay mines off the U-boat basin; it ought to be pretty cissy because they have only got a couple of guns there.