Green’s Dictionary of Slang

pleasure n.

an orgasm; sexual intercourse.

[1498		J. Alcock In die Innocencium n.p.: [L]echery is pleasure].
1560		Becon Inuectiue Agaynst Whoredome cited in Williams Dict. Sexual Lang. I 1055: He denounces ‘those maids ... Al gyuen ... to fylthy pleasaunce’.
1698		‘The Enjoyment’ in Poetical Remaines of Rochester, Etherege, and Others 97: Tho’ fallen from the top of Pleasure Hill, / With Longing Eyes we look up thither still.
1848		Paul Pry 27 Nov. n.p.: From this human scum[i.e. pimps] do many of these children of pleasure (?) suffer blows, indignity, and abuse of the grossest kind.
1888–94		‘Walter’ My Secret Life (1966) IV 774: Then I frigged [...] and after immense trouble got a pleasure.
1934		‘J.M. Hall’ Anecdota Americana II 28: Just about that time I had my pleasure an’ fell off the roof.

SE in slang uses

In compounds

pleasure boat (n.) (also pleasure conduit, ...girth, ...pit, ...place)

the vagina.

1596		Davies of Hereford ‘In Katam’ in Epigrams viii: Content thee Kate, although thy pleasure wasteth, Thy pleasure’s place like a buff jerkin lasteth [F&H].
1662		G. Torriano [trans.] The second alphabet consisting of proverbial phrases 227: Salir il Monte di Venere [...] to get up Venus Mount, viz. to use Carnal Copulation, to get upon a Womans Pleasure Place, or Mount Faulcon.
1730		J. Miller Humours of Oxford I i: gain.: What, bound for the Port of Wedlock, Sir? ape.: No, no, no, no, Sir, I only use her as a Pleasure-Boat [...] purely as a passo Tempo.
1748–49		Cleland Memoirs of a Woman of Pleasure (1985) 77: He lets the fury loose [...] and driving with refresh’d rage, breaks in, and plugs up the whole passage of that soft-pleasure-conduit. [Ibid.] 83: I [...] tightened the pleasure-girth around my restless inmate, by a secret spring of suction and compression.
1888–94		‘Walter’ My Secret Life (1966) II 401: Yet as my belly touched hers, and my prick rubbed against her pleasure-pit it became useless.
1890–1904		Farmer & Henley Sl. and Its Analogues.

pleasure-lady (n.) (also pleasurable lady)

a prostitute (cf. lady of pleasure under lady n.).

1654		Citie Matrons 8: You Pleasure-Ladies, that live by sporting.
1675		Æsopicks 82: Then said the Crow, Why how now sawcie Jack! / Thinkst thou a Strumpet sits upon thy Back? / Were I a Pleasure-Lady, here I’d sleep.
1821		‘A Real Paddy’ Real Life in Ireland 91: All the pleasurable ladies from the Liberty, rode criss cross upon their neddies.
1890–1904		Farmer & Henley Sl. and Its Analogues.

pleasure-pivot (n.)

the penis.

1748–49

Cleland Memoirs of a Woman of Pleasure (1985) 123: So that stuck upon the pleasure-pivot, and clinging round his neck [...] he carried me once around the couch.