Green’s Dictionary of Slang

to wear spectacles.

c.1786		Grose Classical Dict. of the Vulgar Tongue ms. additions n.p.: Saddle, to Saddle one’s Nose, to Wear Spectacles.
1788, 1796		Grose Classical Dict. of the Vulgar Tongue (2nd, 3rd edn).
1811		Lex. Balatronicum.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.

to host a dinner or supper.

c.1786		Grose Classical Dict. of the Vulgar Tongue ms. additions n.p.: The Spit, to give a Dinner or Supper, to Saddle.
1788, 1796		Grose Classical Dict. of the Vulgar Tongue (2nd, 3rd edn).
1811		Lex. Balatronicum.
1823		Egan Grose’s Classical Dict. of the Vulgar Tongue.

1. to have sexual intercourse.

[1832		Satirist (London) 26 Aug. 278/4: Sir Peter ‘commanded his ass to be saddled, and they saddled him’].
2000		Penguin Bk of All-New Aus. Jokes 204: ‘Jack Nicklaus would never leave a girl after he’s made love to her twice – back into bed!’ So they saddle up for the third time.

2. (US gay) to have anal intercourse.

1971		F. Hilaire Thanatos 284: So guys like me will still be saddling hairless boys.
1989–2003		R.O. Scott Gay Sl. Dict. 🌐 anal intercourse: [...] Syn: saddle it; saddle up.

1. the bar of the Theatre Royal, Melbourne, generally accepted as a place to pick up prostitutes; thus used of other places of assignation, see cite 1889.

1871		Leader (Melbourne) 2 Sept. 18/2: No decent woman dare show her face in the stalls of the Royal after a certain hour, because the, gangway is blocked by a crowd of the demimonde. Nor is that institution, known amongst horsey men as the saddling paddock, the sort of place by which any gentleman would like to lead either his wife or his sister.
1876		Argus (Melbourne) 1 July 4/4: Curiosity will doubtless prompt him to enter, and he will find himself in the far-famed ‘saddling paddock’ of the Royal. It is a small bar, presided over by a man — the proceedings here aro too unpleasant for a barmaid to witness. Here the most notorious women of Melbourne nightly throng, and run in the companions they have caught in the stalls or in the vestibules.
1877		S. James Vagabond Papers (2nd series) 139: I am afraid that, on the whole, Melbourne was not a moral city on Monday Night. Certain supper-rooms, and the saddling paddocks and the vestibules of the theatres were crowded.
1880		Lorgnette (Melbourne) 23 Aug. 2/2: That disgraceful eye-sore to the respectable section of the patrons of the Theatre, namely that portion known as ‘The Saddling Paddock’ has been entirely removed, giving/place to a large and commodious PEOPLE’S BAR.
1889		Dead Bird (Sydney) 30 Nov. 2/1: Machattie Park, at Bathurst, has been called the ‘saddling paddock,’ because all the town toffs meet their gals there.
1937		F. Clune Dig, a Drama of Central Aus. (1943) 47: Here the most notorious women of Melbourne nightly throng, and run in the [...] ‘Saddling Paddock’.

2. any place of assignation.

1909		J. Ware Passing Eng. of the Victorian Era 213/1: Saddling-paddock (Australian), place of amusement or rather place of assignation.
1945		Baker Aus. Lang. 124: Saddling paddock, a popular site for alfresco amours.
1955		N. Pulliam I Travelled a Lonely Land (1957) 238/1: saddling paddock – a place for an illicit love affair.
1958		G. Casey Snowball 29: Couples walking to or from some cool, private place among the trees kept a wary eye open. [...] The ribald, popular name of the enclosure round the Government Dam was ‘the saddling paddock’.