Dorothy Lucille Tipton or Billy Tipton

Billy Tipton lived as a man from age 21 till the day she died at age 74. Yes, her three sons (all adopted) never suspected a thing. But that's not the bizarre part. She lived with five women in succession, all of them attractive, a couple of them knockouts. She had intercourse with at least two of them and, who knows, maybe all five. But of the three we know about in detail, none tumbled to the fact that her husband was a woman (one figured it out later). At first you might think: man, I thought my spouse was oblivious. But the more charitable view is that they were taken in by one of the great performances of all time.

We know as much as we know about Billy thanks to a newly published biography by Diane Wood Middlebrook, Suits Me: The Double Life of Billy Tipton. Middlebrook reports that Dorothy Lucille Tipton decided to become Billy Tipton in 1935, ostensibly because it was the only way an aspiring jazz musician could get work in an almost exclusively male business. The transformation wasn't all that tough. Billy's face was boyish, and her figure was more Coke can than Coke bottle. (She had sizable breasts but no waist.) A sheet wrapped around her chest, men's clothes, and a bit of padding in the crotch, and she easily passed.

Suits Me
The Double Life of Billy Tipton