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History of the Boob [from the OED, OED 2 on CDrom, v. 1.14]

Booby (______), n.1 Also 8 boobee, 9 boobie.
[probably ad. Sp. bobo, used both in the sense of ‘fool’ and ‘booby’ (the bird), of doubtful origin. (The Ger. bube, MHG. buobe, is used frequently in the sense of ‘fool, lubber’; but connexion with it is hardly possible: its LG. form is boeve, boef.)]
1. a. ‘A dull, heavy, stupid fellow: a lubber’ (J.); a clown, a nincompoop. Also, spec. a cry-baby (dial. or children’s colloq.).
1599­-1603 Patient Grissil 48 [Welshman loq.] Then, mage a pooby fool of Sir Owen. God’s plude, shall!
1616 Fletcher Cust. Country i. ii, Cry, you great booby.
1687 T. Brown Saints in Upr. Wks. 1730 I. 74 Such a booby as thou art, pretend to dispute the precedence?
1711 Steele Spect. No. 113 _3, I bowed like a great surprised Booby.
1776 Johnson in Boswell (1831) III. 352 We work with our heads, and make the boobies of Birmingham work for us with their hands.
1824 W. Irving T. Trav. I. 260, I was so awkward a booby that I dared scarcely speak to her.
1891 R. P. Chope Dial. Hartland, Dev. 29 Booby, a big child given to crying.
1945 E. Waugh Brideshead Revisited i. viii. 189 ‘Poor simple monk,’ I thought, ‘poor booby.’
1959 I. & P. Opie Lore & Lang. Schoolchildren x. 186 Gloucestershire children comment: you babby, big baby,..booby, [etc.].
b. spec. The last boy in a school class, the dunce.
1825 Ld. Cockburn Mem. i. 4, I never got a single prize, and once sat boobie at the annual public examination.
1849 C. Brontë Shirley III. iv. 75 He was the booby of..grammar school.
c. attrib.
1728 Young Love Fame ii. (1757) 95 The booby father craves a booby son.
1748 Richardson Clarissa xxxi. I. 205 Never was there booby squire that more wanted it [improvement].
1818 Scott Hrt. Midl. iv, There is not a boy on the booby form but should have been scourged for such a solecism in grammar.
d. to beat the booby: see beat v.1 41.
e. Shortened f. booby-hutch: a lock-up or cell. slang.
1938 F. D. Sharpe Sharpe of Flying Squad 329 Booby or Booby Hutch, the cell.
2. A name for different species of gannet, esp. Sula fusca.
1634 Sir T. Herbert Trav. 10 One of the Saylers espying a Bird fitly called a Booby, hee mounted to the top-mast and tooke her. The quality of which Bird is to sit still, not valuing danger.
1707 Sloane Jamaica I. 31 Boobies..so called of Seamen because they do not stir from you, but suffer themselves to be catch’d by the hand.
1819 Byron Juan ii. lxxxii, At length they caught two boobies, and a noddy.
1860 Gosse Rom. Nat. Hist. 83 The booby and the noddy sit on the bare rock in startling tameness.
3. Comb., as
booby-hack U.S. = booby-hut;
booby hatch,
(a) (Naut.), a smaller kind of companion which lifts off in one piece, in use for merchantmen’s half-decks;
(b) a lock-up or gaol (U.S. slang);
(c) a home for the insane (U.S. slang);
booby-hut, a hooded sleigh used in New England;
booby-hutch, a small clumsy cart or carriage used in some parts of England; see also quot. 1881; also, a lock-up or cell; a police station;
booby-prize, a prize awarded in ridicule or fun to the player with the lowest score;
booby-trap, a kind of practical joke in vogue among schoolboys and others (see quots.); also Mil. colloq., a harmless-looking object concealing an explosive charge, designed to go off if the object is disturbed; hence as v. trans., to set with a booby-trap; so booby-trapped ppl. adj.
1888 Boston Daily Globe (Farmer), They collided with Crowley’s *booby hack, knocking the horse down and demolishing the front of the vehicle.
1840 R. Dana Bef. Mast xxxiv. 130 The sky-light and *booby-hatch [are] put on.
1859 G. W. Matsell Vocabulum 13/2 Booby-hatch, station-house.
1883 Chamb. Jrnl. 141 The after or booby-hatch was covered with a network of lashings.
1897 Ade Pink Marsh 3 They’d have him in the booby-hatch in about two hours.
1923 Time 10 Mar. 15/3 Liane,..whose specialty is driving lover after lover to ruin, death, or the booby-hatch.
1931 G. Irwin Amer. Tramp & Underworld Slang 33 Booby Hatch, a police station or village gaol.
1936 Wodehouse Laughing Gas xi. 111 What, tell people you’re me and I’m you. Sure we could, if you don’t mind being put in the booby-hatch.
1720 Weekly Jrnl. 4 June 1623/2 Not a Raw bon’d Jade, or a *Booby-Hutch in City and Suburbs but will be hacked out to City Apprentices.
1818 H. More Hist. Mr. Fanton Stories (1830) I. 10 All that multitude of coaches, chariots, chaises, vis-a-vis, booby-hutches, sulkies, etc.
1881 Evans Leicestersh. Gloss. (E.D.S.), Booby-hutch, a hand-barrow; a small deep cart; a sentry-box; any movable ‘coop’ or ‘hutch’ of any kind intended for the use of a single human occupant. The carts drawn by dogs before the passing of Martin’s Act were often so called.
1889 Barrère & Leland Dict. Slang I. 161/1 Booby-hutch (thieves), the police-station.
1938 Booby hutch [see sense 1 e].
1889 Puck (U.S.) 17 July 378/1 Into infinitesimal shreds he tears A beautiful *Booby Prize.
1900 E. T. Fowler Farringdons iii. 55 Your prize would have been no better than a booby-prize.
1929 G. Stowell Hist. Button Hill i. 64 The incorrigible Mr. Denworthy presented as a booby-prize a small sample bottle of Worcester sauce.
1850 F. E. Smedley Frank Fairlegh iii. 28 The construction of what he called a ‘*booby-trap’.
1868 Chamb. Jrnl., A ‘booby-trap’..it consisted..of books, boots, etc., balanced on the top of a door, which was left ajar, so that the first incomer got a solid shower-bath.
1882 Sat. Rev. 4 Nov. 600 Perpetually on the alert for booby-traps.
1917 E. F. Wood Note-Bk. Intelligence Officer xix. 271 ‘Booby’ traps were sprinkled about the country in the form of bombs.
1918 P. Gibbs From Bapaume to Passchendaele 4 The enemy left..‘booby-traps’ to blow a man to bits or blind him for life if he touched a harmless-looking stick or opened the lid of a box.
1943 Illustr. London News 1 May 483 Doors and windows are easily booby-trapped.
1959 ‘M. Derby’ Tigress iii. 130 The ugly foreground, mined and booby-trapped and ambushed.
boob (____), n. slang (orig. U.S.).
[Shortened f. booby n.1]
1. = booby n.1 1 e.
1908 J. M. Sullivan Crim. Slang 4 Boob, the lockup, station house, or city prison.
1911 G. Bronson-Howard Enemy to Society v. 159 Stooling for the coppers and swearing many a right guy into the boob.
1923 E. Wallace Missing Million xiii. 108, I thought you were in ‘boob’.
1941 Coast to Coast 1941 232 Seeing Don get chucked out of the Ballarat and carted off to the boob.
1958 M. Pugh Wilderness of Monkeys xiv. 177 ‘Got six months in jail,’ May added. ‘Half a stretch in the boob,’ Maguire said.
2. = booby n.1 1 a.
1909 Sat. Even. Post 27 Mar. 7/3, I had to tell her the boob had gone for the day.
1915 [see bone-headed a.].
1920 Chambers’s Jrnl. May 282/1 Of course war is wrong–any boob knows that.
1923 W. Deeping Secret Sanctuary xvi. 160 And not a soul to speak to but that boob of a boy once in the day.
1930 G. B. Shaw Apple Cart i. 26 You gave it away, like the boobs you are, to the Pentland Forth Syndicate.
1961 [see boo-boo].
3. A foolish mistake or blunder. Also attrib., foolish, inane.
1934 R. Stout Fer-de-Lance (1935) i. 8 A boob thing to say.
1959 ‘O. Mills’ Stairway to Murder xvi. 167 Boob Number Two... The prison service isn’t quite like the Army, Colonel Clive.
1966 P. Moloney Plea for Mersey 55 Newspapers have I read in every town And many a boob and misprint have I seen.
1969 Daily Tel. (Colour Suppl.) 10 Jan. 7 (U.S.A.) A factory hand released by technology into ever greater leisure may be content to watch the ‘boob toob’ (TV) or go fishing.
4. [prob. shortening of booby n.2] pl. The breasts. slang (orig. U.S.).
1949 H. Miller Sexus (1969) xiii. 305, I felt her sloshy boobs joggling me but I was too intent on pursuing the ramifications of Coleridge’s amazing mind to let her vegetable appendages disturb me.
1955 T. Williams Cat on Hot Tin Roof (1956) i. 7 He always drops his eyes down my body when I’m talkin’ to him, drops his eyes to my boobs an’ licks his old chops!
1968 Daily Mirror 27 Aug. 7/5 If people insist on talking about her boobs, she would rather they called them boobs, which is a way-out word,..rather than breasts.

Booboisie
booboisie (__________). U.S. slang.
[Jocular formation f. boob n. 2 + -oisie, after bourgeoisie.]
‘Boobs’ as a class.
1922 in Mencken Amer. Lang. (ed. 4, 1946) xi. 560.
1927 St. John Ervine in Observer 24 Apr. 15/1, I would not for the world rob the booboisie of their entertainments. Let them have their footling stories..on the screen.
1959 J. Thurber Years with Ross iv. 61 Those well-known..objects of..scorn and ridicule, the booboisie.
1961 20th Cent. Jan. 72 They wanted to be as eccentric as they pleased..and..could not do that among the booboisie of America.

For the more visually inclined, the less literal, this history: boooooby
posted by degustibus at 8:46 AM