lollipop n.1
1. in senses of ‘sweetness’.
(a) a woman, esp. an attractive one.
![[US]](/static/img/flags/us.png "United States") | Miss Gilbert’s Career (1870) 153: ‘Who is that fat old lollypop in the door yonder?’ ‘That is Mrs. Ruggles, your landlady.’. | |
![[Aus]](/static/img/flags/aus.png "Australia") | Sport (Adelaide) 14 Mar. 5/4: The betting is 10 to 1 on that Clarrie H: and Shen have got a bigger interest in a certain lollie pop than Tom F . | |
| Broadway Melody 59: Do you see what I see, Stewie? If that isn’t a lollypop —. | |
| (con. 1930s) Night People 42: Pops was guarding his eighteen-year-old lollipop. | |
| Secrets of Harry Bright (1986) 62: He saw the petite young lollipop stroll in and sit at the bar. |
(b) one’s special favourite, the prize article in a collection.
| Fact’ry ’Ands 160: They’s scroungers what think they’s just the lolly in a red tie [...] but they ain’t respectible. | |
![[UK]](/static/img/flags/uk.png "United Kingdom") | DSUE (8th edn) 694/1: lollipop [...] Anything specially good. |
(c) (Aus.) anything easy [play on sweet adj.1 (2)].
| Digger Dialects 32: lolly — (1) Something easy. |
(d) (orig. US) one’s sweetheart, usu. used as a term of affection.
| in Zwilling TAD Lex. (1993) 115: Say Harry I just called up the old lady and told her I wouldn’t be home until quite late and she was nice as pie. Just said allright my lollypop and hung up. | |
| Decadence in Decadence and Other Plays (1985) 16: What’s a-matter little lollipop. |
(e) (US) an effeminate man or a homosexual.
| New York Day by Day 24 July [synd. col.] It is the haunt of those strange lisping lollipops – the psycopathic [sic] hybrids that migrate to Broadway. | |
| ‘The Big Knockover’ Story Omnibus (1966) 306: These bimbos were a couple of lollipops for fair. There wouldn’t have been an ounce of fight in a ton of them. | |
| Blind Man with a Pistol (1971) 22: ‘Ooooo!’ a falsetto voice cried delightedly. ‘A lollipop!’. |
2. in sense of that which is sucked or a play on sucker n.1 (3a)
(a) the penis.
| New Cockalorum Songster in Spedding & Watt (eds) Bawdy Songbooks (2011) II 17: [song title] Miss in Her Teens & the Lolly-Pop Man. | |
| Sam Sly 6 Jan. 2/1: It is not true that Mrs. C— p—s, of Old G—l-lane, is remarkably fond of the lollypop man. | |
| [ | | Nocturnal Meeting 45: Sucking my soft prick like a lollipop]. |
| Bagnio Misc. 43: We presently sucked to our heart’s content three very pleasant lollypops, with two sugar balls attached to each. | |
| ‘You’ve Got to Give Me Some’ 🎵 Sweetest candy in a candy shop / Is just your sweet sweet lollipop / You gotta give me some / Please give me some / I love all day suckers / You gotta give me some’. | |
| ‘Take It Easy, Greasy’ 🎵 Sweetest candy in the candy shop, / It’s just your sweet, sweet lollipop! | |
| ‘Jeanie in “Two Pussies”’ [comic strip] in Tijuana Bibles (1997) 143: Suck hard. Pretend it’s Streaky’s lolly pop. | |
 | ‘Bite It’ 🎵 Suck it! (lollipop), suck it, suck the hell out of it (ah, lollipop) suck it, suck it now. | |
| Faggots 320: Hot dog, joy stick, kidney wiper, knitting needle, lance!, lollipop. | |
| Gay (S)language. | |
| Pimp’s Rap 154: She held it [i.e. the penis] in her delicate hands like a huge lollipop [...] as it throbbed backwards and forwards. |
(b) (orig. Aus., later US black) a gullible person who has been ‘sucked’, i.e. taken advantage of; also attrib.
| Sun. Times (Perth) 26 May 4/8: Do this and you’ll scatter more pleasure than playing the lollypop jay. | |
| Digger Dialects 32: lolly [...] (2) A person easy to trick or overcome. | |
| Maltese Falcon (1965) 420: Jesus God! Is this the first thing you guys ever stole? You’re a fine lot of lollipops! | |
| Jailhouse Jargon and Street Sl. [unpub. ms.]. |
(c) (also pop) the penis or vagina in the context of oral sex.
| joke cited in Rationale of the Dirty Joke (1972) I 102: ‘Oh look,’ he says, ‘you have hair on your lollypop.’ ‘Yes, and I’m not even twelve yet.’. | |
| 5000 Adult Sex Words and Phrases. | |
| Flesh and Blood (1978) 33: Who cared if I let someone suck my pop? | |
| Maledicta VI:1+2 (Summer/Winter) 131: Vagina […] lollipop. | |
| Dict. of Invective (1991) 255: ‘I love lollipops’ (female to male [chat-up line]). | |
| Lucky You 266: Not till we play some lollipop, her and me. |
(d) an older man who is happy to indulge a younger woman, whether or not he receives any favours in return.
| [ | | ‘Humbug Club Song’ in Hilaria 46: Then wicked wit W— and old lolly-pop Q— ]. |
| DSUE (8th edn) 694/1: lollipop [...] A ‘sugar-daddy’: (shopgirls’ and typists’). |
(e) the female breast.
| Airtight Willie and Me 15: Put this whole grand in your bosom right next to your boss lollipops. |
In compounds
(US) fellatio.
| Toots and Casper Go to a ‘Circus’ 7: [comic] ‘My God, Casper! She’s going down on him!’ ‘Stand still, Allie-Wallie, I’ll give you a lollypop ride’. |
(US gay) a lavatory, esp. one where one can get quick, anonymous sex.
| Gay (S)language. | |
| Queer Sl. in the Gay 90s 🌐 Lollipop Stop – A highway rest stop used by gay men for cruising. |
(Aus.) short tight male bathing trunks.
| Age (Melbourne) 15 Dec. (Today Suppl.) 4/1: Also, '50s-style swimming trunks are making a bit of a fashion comeback; you know, the thigh-clinging ones that look a bit like cropped bicycle shorts with a waistband. But washboard stomachs only need apply. But really, my advice is keep that lolly bag hidden away. | |
| Sun-Herald (Sydney) 24 Nov. (Sunday Metro Suppl.) n.p.: Speaking of skimpy, get a load of Lawrence Mooney’s Speedos. No really, go on, take a good look. He wants you to. Are the contents of his ‘lolly bag’, as he calls it, merely ‘two Tic Tacs and a jelly bean’? | |
| ‘Aus. Sl.’ paper presented to Leicester U. Slang Workshop, Sept. 2012 n.p.: The speedo variety [of trunks] developed an extraordinary number of risqué or simply curious synonyms: [...] lolly bags (cf. the sense ‘scrotum’ ). |