She was born Dorthy Tipton and had trouble breaking into the world of jazz as a woman, so she impersonated a man.
From Cecil Adams:
You think I could forget the story of Billy Tipton? Yes, she 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. In fact Billy was positively handsome; women thought he was a doll. A talented pianist, horn player, and tenor, he quickly found a gig with a band.
At first Billy was strictly a cross-dresser, making no great effort to conceal her femaleness during her off hours. She lived with a woman with the unusual name of Non Earl Harrell, in what other musicians assumed was a lesbian relationship. Initially they were based in Oklahoma City, but by 1940 they had moved to Joplin, Missouri, then an entertainment center. There Billy began to masquerade as a male full-time, a pose he would adopt for the rest of his life.
Billy and Non Earl broke up in 1942. After a liaison of some years with a singer named June, Billy took up with Betty Cox, a pretty 19-year-old with a striking figure. The two stayed together for seven years, during which they had what Betty recalled as a passionate heterosexual relationship, including intercourse. She even thought she'd had a miscarriage once. How could you share a bed with someone for seven years and not realize he was a she? Breathtaking naivete had to be part of it, plus the fact that, as an accomplished entertainer who was 13 years Betty's senior, Billy called the shots. They made love only in the dark. Billy never removed his underwear and wore a jockstrap that Betty later speculated was fitted with a "prosthesis." He wore massive chest bindings at all times, supposedly for an old injury. He would not let himself be touched below the waist nor disturbed in the bathroom. Betty may also have been a bit distracted. Acquaintances said she went out with other men while she was with Billy, and while she appears to have been genuinely fond of him, in some ways this may have been a marriage of convenience for both.
Rest of the story here:
http://www.straightdope.com/columns/read/1060/whats-the-story-on-the-female-jazz-musician-who-lived-as-a-man
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