Green’s Dictionary of Slang

deep adv.

1. of a wager, (losing) substantially.

[UK]‘A Flat Enlightened’ Life in the West II 31: ‘I am only out a eouple of hundred. Lord K— lost deep’.

2. (US black, also deep-down) a general intensifier.

[UK]A. Salkey Come Home, Malcolm Heartland 88: I was deep, real deep into Malcolm. Brother Malcolm was all, man.
[US]S. King It (1987) 41: Whoever writes these little homilies has got a case of the deep-down crazies.
[US](con. 1960s) G. Washington Blood Brothers 82: The next patient looked like he had a bad case of leprosy or elephantitis. Whatever it was, he had a bad case of the deep uglies.
[US]G. Pelecanos Right As Rain 198: A young man [...] made a comment directed at Juana, saying how he’d like to ‘kick that shit deep’.
[US]R. Price Lush Life 27: Tristan could almost count the times he’d been this deep away from home .

3. (orig. US black gang) well-supplied with members, thus phr. roll deep, roll thick, to have a large number of individuals in one’s gang or (in other contexts) group; also used adj.

[US]NWA ‘Gangsta Gangsta’ 🎵 We decide to roll and we deep.
[US]L. Bing Do or Die (1992) 36: Crips, man — deep!
[US](con. 1975) K. Scott Monster (1994) 10: ‘There they go!’ Lep said, spotting the gathering of about fifteen people. ‘Damn, they deep too.’.
[US]Dr Dre ‘Some L.A. Shit’ 🎵 We roll deep, smoke on weed drink and back heat / Requirements for survival each day -- in L.A.!
[US]B. Coleman Check the Technique 271: ‘They [i.e. the Mobb Deep rappers] used to roll pretty deep out there with all their boys, probably ten guys most of the time’.
[US]W.J. Cobb To the Break of Dawn 60: [T]he ranks were deep. Listen, Guru, and the crew he ran with [...] rolled thick, like a host of ghetto potentates with diplomatic immunity.
[US]‘Dutch’ ? (Pronounced Que) [ebook] They knew his crew was too deep to trying anything.
[US]M. Lacher On the Bro’d 207: [T]hings were different this time ’cause we didn’t have our deep crew.
Stormzy ‘Shut Up’ 🎵 They roll deep, I roll squaddy / Got about 25 goons in my posse.

4. (US black gang) in number.

[US]K. Scott Monster (1994) 253: We’d pile into my car four deep.
[US]UGK ‘One Day’ 🎵 I remember bein eight deep off in Chucky crib.
[US]G. Pelecanos Way Home (2009) 222: A car, three deep, rolled up on him in while he was walking to his aunt’s house.

In phrases

deep-dick (v.) (also deep end, deep-fuck)

(US gay) to have rough, vigorous anal intercourse; thus deep-dicking.

[US]W. Leyland (ed.) Studflesh 67: I knew that if I didn’t get off this taste-treat soon, I’d lose the possible pleasure of this Italian stud deep-dicking my ass [Simes:DLSS].
[US]Telephone Tales (N.J.) Sept. 87: Ace and Dave increased the tempo of their deep-dicking, knowing they were hitting my trigger and [...] driving me over the edge [Simes:DLSS].
[US]‘T. Caffrey’ Hitting Home 133: Alan continued to suck Bill’s cock as John deep-ended him, moaning loudly whenever John slammed in particularly hard [Simes:DLSS].
J. Preston Flesh & Word 89: The muscles in his body tossed like ocean waves in a storm as he deep-dicked me in a tight rhythm [Simes:DLSS].
Sydney Star Obs. 2 Oct. 34/6: [personal advert] Attractive submissive, passive guy..seeks older men to deep fuck my mouth and/or arsehole [Simes:DLSS].
deep-dish (adj.)

(US) of friends, extremely intimate, committed; of sexual action, intense.

[US]‘R. Cummings’ Cockfighters 15: We’d been deep-dish buddies for five years now [Simes:DLSS].
[US]‘S. West’ Cumin’ Thing 28: [H]e began deep-dish pumping [Simes:DLSS].
deep-eight (v.) [either rhy. sl. or the supposed length of a long penis]

(US gay) to fellate.

[US]Inches (San Francisco) Sept. 92/2: [no text] [Simes:DLSS].
deep-tongue (n.)

(US) to deep-kiss.

[US]Size Tales (N.J.) Aug. 29/2: Kevin [...] ..began again to deep-tongue me [Simes:DLSS].