Women Like That
| Women Like That The Transformation of Dorothy Tipton |
by Francesca Susanna
There was a young woman named Dorothy who, in the 1930s, wanted to make her living playing saxophone or piano in swing bands, making records, and generally “living the life of a jazz-man.” She was living in a boarding house in Oklahoma City with her mother and getting a few gigs with bands that played popular dance music in clubs. Her band-mates considered her the best musician of them all. Dorothy Tipton was passionate about jazz – it was her calling, and nothing else except music would be her life’s work. But she was a girl.
She had gone to Oklahoma City in 1933 at the age of 18, optimistic and encouraged. It was the Depression and Oklahoma was a dry state, but in boom-town, oil-rich Oklahoma City people were dancing. There was a lot of competition among musicians, and many bars and clubs simply would not hire a woman no matter how talented. When the jobs dried up she went to Muskogee to crash on the floor of her aunt’s one-room apartment with two teenage cousins and a baby.
She heard of a band in need of a sax player, but she knew they would not hire a woman. With some help from her cousins Eilene and Madeline, she bound her breasts with a piece of worn-out sheet. Dressed sharply in white pants and a dark jacket she became “Billy” Tipton and got the job.
Back in Oklahoma City she began to cross-dress for auditions and work. Billy / Dorothy became involved with an older woman named Non Earl (because her estranged husband was Earl), and they stayed together in a boarding house. Dorothy was 19, and Non Earl in her early thirties.
The transition from Dorothy to Billy – from cross-dresser to ‘typical’ heterosexual man – was not completed the day her cousins pinned the sheet around her chest. Norma Teagarden recalled that “she never pretended to be a man, you know. She just always wore men’s clothes... Playing the front line, she wanted to be in uniform the same as the rest of the musicians.”
For several years Billy cross-dressed for work, but in daily life she was considered simply a gay woman who wore men’s clothes and lived with her girlfriend. Billy apparently thought of herself that way based on a photograph from 1938 of her with her mother and her younger brother William. The picture shows Billy in men’s clothes but making no effort to disguise breasts or waistline. The audiences may have been fooled, but her friends and band mates didn’t need to be. The fact that she and Non Earl were “show people” was enough to explain the unusual set up.
Once Dorothy began to adopt the Billy persona, life in general became much easier. As a woman, she would have had to fight a society unwilling to allow her to direct her own destiny, but as a man, it was expected. A couple of years later, during a spell of little work, Billy retired ‘Dorothy’ forever. He and his ‘wife’ Non Earl moved from Oklahoma City to Joplin, Missouri, and after that Billy went from cross-dressing to passing.
Billy worked on perfecting his persona in earnest. His image was one of a gentleman, a heterosexual male, with everything that that implied in 1940’s America. He and Non Earl settled into typical domesticity, and he created stories about an unhealed rib to explain why he wasn’t in the war and why he wore tight chest bindings. Soon Non Earl, a good dozen years older than her ‘husband,’ grew bored trying to play the role of a typical American housewife. She left.
After Non Earl, Billy cultivated a definite taste in women; young, beautiful, glamorous – the sort of women straight men drooled over. He got them too. In 1943, Billy “married” June, who was 17 when they first met; Billy was 28. They lived together and traveled to Billy’s various gigs together for two or three years before they split up. June began to tell tales on Billy, that he was a hermaphrodite with a very small penis. At that time, hermaphrodite was often used as a euphemism for lesbian, but it’s impossible to guess if she meant that she knew he was a woman or if he explained away his vagina by claiming to be a hermaphrodite.
When June left, Billy had already met Betty, who was 18 and very beautiful. She later described him as “neat, clean, and he didn’t use foul language with me... cute as a bug! Such a nice smile!” They “married” later in 1946. She did not suspect he was woman until his death, although they were sexually active together.
That marriage broke up in 1954, and almost immediately there was another woman in his life, Maryann, a classy call girl. She was a little older, thirty-three, but beautiful and glamorous. She did not guess that he was a woman during their marriage, although they had sex and she was already experienced. When she was interviewed for a book about Billy, she said, “Honey, I can hardly wait to read your book. I thought it was a penis.” Billy had unbreachable habits to avoid discovery. He locked the bathroom door when he bathed and dressed, he made love in the dark, and he was always the dominant partner. “You didn’t touch Billy,” Maryann explained.
Billy had formed his own group, the Billy Tipton Trio, and as they traveled around and became more well known, keeping his secret became more and more dire. Every now and again someone from his past would turn up, or someone more sophisticated than his usual cronies would recognize him as a passing woman.
In 1958, Billy and Maryann arrived in Spokane, Washington, where they settled down in the suburbs. His trio had a contract to play as the house band in a nightclub there and Billy also worked for an old friend, Dave Sobol, as a booking agent. In 1960 after seven years together, Maryann discovered that Billy had become involved with another woman, Kitty Kelly. Billed as “The Irish Venus,” Kelly was a stripper at the club. She was twenty-seven, and Billy was forty-five, although claiming to be a bit younger.
Billy and Kitty began to live together in 1961 in a loving but sex-free marriage. They adopted three boys, Kitty joined the PTA and the family took fishing trips in Billy’s free time. When the marriage broke up after 16 years, Billy started seeing Maryann again. They talked about living together, but Maryann could see that the chances of it working were slim.
Maryann did, however, confront him about her 1960 discovery of a birth certificate for a Dorothy Tipton. Later, after the breakup with Kitty, she asked Billy if he was a woman, if he was Dorothy. He said nothing, she recalled, just gave her a “terrible look.”
Billy died of an ulcer in 1989 and it was the coroner’s report that brought out Billy’s secret: “The deceased had the body of a normal woman past menopause.”
Further Reading:
Suits Me, the Double Life of Billy Tipton, by Diane Wood Middlebrook, Houghton Mifflin, 1998.
Billy Tipton Biographer Diane Wood Middlebrook Talks about Cross-Dressing Jerry Jazz Musician, www.jerryjazzmusician.com.
Francesca Susannah is a writer interested in lesbians through history. She lives in Burlington.