Green’s Dictionary of Slang

1. a weakling, an ineffectual person; thus woman-jessie, a weak man who physically abuses women.

1929		Eve. Teleg. (Dundee) 20 Sept. 5/4: ‘Jessies’ who wear pullovers with lounge suits deserve more than discomfort.
1934		Z.N. Hurston Jonah’s Gourd Vine (1995) 51: He don’t fight no men-folks. He’s uh woman-jessie. Beat up women and run from mens.
1938		M.K. Rawlings Yearling 274: I had me a good go-round with them jessies.
1943		R.L. Bellem ‘Dead Man’s Shakedown’ in Dan Turner Detective Mar. 🌐 (of a woman) I barked an order over my shoulder to the scared jessie in the ticket-selling booth.
1952		‘Josephine Tey’ Singing Sands 31: It’s an awful jessie-like thing to present a bookey [i.e. bouquet]’.
1997		(con. 1950s) J. Byrne Slab Boys [film script] 123: You can talk! I’m no surprised the big jessie in the kilt gave ye the heave.
2004		C. Brookmyre Be My Enemy 164: It was always freezing and he was an unrepentant Big Jessie.

2. (US) a young woman.

1942		R.L. Bellem ‘Daughter of Murder’ Dan Turner – Hollywood Detective Dec. 🌐 Presently a brunette jessie opened up [...] She was a nifty number, rather young.
1943		R.L. Bellem ‘Feature Snatch!’ Dan Turner - Hollywood Detective Feb. 🌐 I reached for a spare necktie on my dresser, knotted the jessie’s arms behind her.

3. a male homosexual.

1988		J. McDonald Dict. of Obscenity etc.
1994		I. Welsh ‘A Smart Cunt’ Acid House 242: Young queens, ten a penny, the fuckin wee jessies.
1998		I. Welsh Filth 263: There’s a bloody jessie-boy in the hat for the inspector’s post.
2008		Financial Times 25 Aug. 2/6: I wore a kilt every day when I went to school. [...] It was a pain because you used to be called a Jessie.
2014		T. Black Artefacts of the Dead [ebook] His father had feared his boy would be brought up soft [...] ‘You’ll have that boy a jessie’ .

4. in attrib. use sense of sense 4.

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.

5. (S.Afr. gay) a Jewish homosexual man.

2003

K. Cage Gayle.