Green’s Dictionary of Slang

Tootsie Roll n.

[brandname of a small chocolate cake + ref. to jelly roll n.]

1. (US) the penis.

[US](con. 1920s) ‘Harry Grey’ Hoods (1953) 230: ‘Give him your tootsie roll,’ she laughed. [...] ‘Not me, baby, I ain’t the type. I’ll persuade him with a different tool.’.

2. in drug uses.

(a) a marijuana cigarette [play on SE roll].

[US]B. Rodgers Queens’ Vernacular 199: tootsie roll [...] 2. brown-papered joint, ie marijuana ciggie.

(b) Mexican heroin [the consistency and colour of Mexican heroin and chocolate (stuff) under chocolate adj.].

[US]Bentley & Corbett Prison Sl. 71: Tootsie Roll also Tar Mexican heroin.
[US]ONDCP Street Terms 21: Tootsie roll — Heroin.

(c) methadone [the image is of ‘fake’ heroin of no more worth to an addict than a Tootsie Roll].

Emmett & Nice Understanding Drugs 160: Methadone – doll, dolly, red rock, tootsie roll.

(d) opium.

[US]Microgram Bulletin XXXVI:11 249: The DEA North Central Laboratory (Chicago, Illinois) recently received 38 rectangular packages consisting of clear packaging tape over a brown leafy substance over flat rolled pieces of plastic containing a black tacky substance, suspected opium [...] The packets (which are locally known as ‘Tootsie Rolls’) varied in size from 1 x 1 x 1 inch to 1 x 1 x 16 inches, and were originally seized [...] from a casket arriving at the Los Angeles International Airport on a flight from Thailand.

3. (US black) an attractive woman.

[US]I. Freeman Out of the Burning (1961) 142: ‘You boys know where we can get some nice chocolate tootsie rolls?’ [...] ‘Sure. I show you. Tetra Club, best house in Brooklyn.’.
[US]R. Klein Jailhouse Jargon and Street Sl. [unpub. ms.].
[US]‘Master Pimp’ Pimp’s Rap 167: This fine jet black honey with a tootsie roll booty.

4. (US black teen) a dance in which the knees are moved inwards and outwards, supposedly showing off one’s buttocks [? toches n. (1) + SE roll].

Wu-Tang Clan ‘Method Man’ 🎵 on Enter the Wu-Tang (36 Chambers) [album] Now how many licks does it take / For me to hit the Tootsie Roll center of a break.
Foesum ‘Listen To The Sound’ 🎵 on Perfection [album] I love to see them skirts do the tootsie roll / with a hell of a body, no shame in the game.