Green’s Dictionary of Slang

1. used of one who takes a long time to do something, e.g. pay a bill or debt.

c.1698		B.E. Dict. Canting Crew n.p.: Long-winded Pay-master, one that very slowly, heavily, or late Paies.
1725		New Canting Dict. [as cit. c.1698].
c.1786		Grose Classical Dict. of the Vulgar Tongue ms. additions n.p.: Long-Winded. A Long Winded [text deleted] One who preaches long tedious Sermons.
1832		Egan Bk of Sports 98: The cash was forthcoming for his work [...] although a few of his customers, to use his own words, were rather ‘long-winded,’ and he considered it ungenteel to ask a gentleman for money.
1908		Sun. Times (Perth) 3 May 1/1: A promient Labour M.L.A. is a trifle long-winded in his drapery debts.

2. used of a man (or woman) who takes a long time to reach orgasm.

1941		G. Legman ‘Lang. of Homosexuality’ Appendix VII in Henry Sex Variants.
1949		in Lost Limericks 15: So, come all you fellows / And listen to me: / Never place your erection / In a long-winded she.
1960		in E. Cray Erotic Muse (1992) 292: So come all you young lovers, and listen to me, / Don’t waste your erection on a long-winded she. / For your root will just wither and your passion will die.
1968		N. Heard Howard Street 45: The damned niggers wanted to [...] stay on all night. They were too long-winded.
1972		B. Rodgers Queens’ Vernacular 128: long-winded (’40s) taking a long time till ejaculation.
1983		N. Heard House of Slammers 46: You’re certainly long-winded tonight, Serge-honey.
1992		(con. 1920s) F.M. Davis Livin’ the Blues 73: You long-winded spades’ll wear a woman out.