Where does red wings come from?
Like a lot of sex slang, red wings might sound like some kid made it up and slapped it on Urban Dictionary. But, the term is actually found in Hunter S. Thompson's 1966 Hells Angels: The Strange and Terrible Saga of the Outlaw Motorcycle Gangs. In the nonfiction novel, Thompson documents red wings as one of various "wings" the notorious bikers could earn—and boast like a sexual status symbol.
Red, here, refers to menstrual blood and wings is a reference to earning one's wings, wing-shaped badges US Air Force cadets have been getting when they graduate since the 1940s. Together, red wings jokingly implies a person has performed some brave act of sexual intimacy.
Since Thompson, red wings has spread in popular slang—with people apparently later explaining that smudges of blood left on the side of the mouth after the act look like red bird wings, hence red wings.
Increasingly in the 2000s, a person is also said to earn their red wings after having vaginal sex with a woman on her period.
Who uses red wings?
Sorry Detroit Red Wings fans. Your team name, based on a historic nickname, has nothing to do with the sexual slang but you still may be the butt of some jokes thanks to it.
Anyone one on their period? I'm trynna earn my red wings TONIGHT!
@Tellezeus, January, 2017
It turns out that people are having oral sex with a woman while they’re on their periods, and the people that do it treat it as a rite of passage towards earning their red wings.
Christine Rivas, Rebel Circus, January, 2017
Picture the scene: you are in the bathroom excitedly preparing to dance in the dark with someone. You freshen up, slip off your panties…and promptly discover a big red stain. Oh no. The night could go two ways from there: you can grab a Kotex and tell your date plans are off, or, you can sexily saunter out and announce to your partner that they will be earning their red wings tonight!
Miss Annabelle, Annabelle's (blog) November, 2017