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Gender Reversal as Empowerment

Esther Newton notes that for women gender reversal and the subsequent "gain" of masculinity have historically empowered lesbian, feminist women. Many women were inspired by famous mannish lesbians, including Gertrude Stein and Vita Sackville-West. But no one was more emblematic of the mannish lesbian than the cross-dressing protagonist of Radclyffe Hall's The Well of Loneliness (1928), Stephen Gordon.

Gordon's "cross-dressing" is not just vestimentary; it starts with her "narrow-hipped and wide shouldered" body, the source of her own "mannish" pride. Her body, however, is also the source of her alienation: "That night she stared at herself in the glass; and even as she did so, she hated her body with its muscular shoulders, its small compact breasts, and its slender flanks of an athlete. All her life she must drag this body of hers like a monstrous fetter imposed on her spirit."

For Gordon, cross-dressing is not a masquerade; it is as congenital as "inversion" itself. Hall's argument for religious and social toleration and an end to rests on her presentation of homosexuality (and cross-dressing) as a congenital condition. But, as the novel's apt title indicates, her work is ultimately not a narrative of triumph.

Virginia Woolf's 1928 novel Orlando also has didactic aspirations although these aspirations are diluted by its satire. Subtitled "a biography," Orlando follows the life of its hero/heroine, from when he is sixteen in 1586 to her "thirty-sixth" year some three hundred forty-two years later in 1928.

Unlike Sarah and Stephen, Orlando actually changes sex, but also unlike them, Orlando starts off as a boy. Woolf's satiric "transsexual" fantasy, however, is by no means Myra Breckinridge; Orlando's change is not a "cure" for anything and happens effortlessly: "He stretched himself. He rose. . . . he was a woman."

The effortlessness of his/her transformation is central to Woolf's agenda in Orlando: "Different though the sexes are, they intermix. In every human being a vacillation from one sex to the other takes place, and often it is only the clothes that keep the male or female likeness, while underneath the sex is the very opposite of what it is above."

Her intention here is further illuminated by her notes in A Writer's Diary that suggest "Vita [Sackville-West] should be Orlando, a young nobleman." Yet just because Orlando is based on a bisexual, cross-dressing woman whose life helped define the mythic mannish lesbian does not mean that Orlando lives a fulfilling life. Once a "woman," Orlando loses all control of her wealth and autonomy as a "man."

What are we to make of such a loss of power? Does Orlando sigh that ultimately men have social power and that nobody should ever want to be a woman because of women's social powerlessness? Or, since the novel is inspired by Sackville-West, are we to interpret Orlando the man as a cross-dressed Vita Sackville-West?

Does the novel then prove that the cross-dressed lesbian should never divulge her real sex? Woolf never allows us close enough to the novel to decipher the answers. Despite Orlando's playfulness, Woolf's novel is finally not too far from Hall's The Well of Loneliness.

Josephine Tey's mystery novel To Love and Be Wise (1951) also showcases a lesbian cross-dresser. Leslie Searle uses her cross-dressed identity as a famous American male photographer to revenge her cousin's death, who committed suicide while married to Walter Whitmore. Searle "kills" her male identity after a public fight with Whitmore to make it seem that Whitmore killed him.

What is provocative about To Love and Be Wise is that despite Searle's criminal intent, her cross-dressing is never condemned. As with Gordon in The Well of Loneliness, cross-dressing is the logical conclusion for Searle's body. When Searle's plans are discovered by Inspector Grant, not only does he not press charges, but he becomes enamored of her, impressed by her cleverness.

He compares her to a man in Gloucestershire who had worked for twenty years hauling coal, but, it was discovered after his death, was actually a woman. Grant resolves that "some are genuinely happier in men's things; but a great many do it from love of adventure, and a few from economic necessity."

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