Green’s Dictionary of Slang

a very small or a child’s penis; thus excl. my winkie!

1962		International Journal Psychoanalysis XXXV 303/2: The patient was afraid of his big hands and big penis and wilted under mockery and castration threats against his own little ‘winkie’.
1980		N. Bogner 7th Avenue 345: Nice big thick Ubangi lips on your skinny little winkie.
1986		Sun. Times 5 Oct. 47: Spitting Image was back on Sunday on ITV with a winkie-wiggling contest.
1996		(con. 1970) G. Moxley Danti-Dan in McGuinness Dazzling Dark (1996) II vi: She made me [...] made me take out my winkie.
1996		(con. 1964-65) B. Thorpe Sex and Thugs and Rock ’n’ Roll 85: She giggled, looking at my naked winkie.
1999		J. Poller Reach 50: In the third photo the baby is revealed as a boy [...] his tiny wizened winkie is clearly visible.
2014		E. Pruitt ‘Houston’ in ThugLit Mar. [ebook] She must've feared another advance by my wilted winkie.
2015		L. McInerney Glorious Heresies 103: Popping cherries all around her, [...] with her sworn guarantee she wouldn’t laugh at the size of their winkies.
2022		R. Holt on Twitter 16 Mar. 🌐 There’s this man whose continually DMs me to tell me I’m not funny and then sends me a pic of his bum or his tiny winky.