(Literary Masterpieces, Critical Compilation)

At the age of fifty-two, after cross-dressing in secret for forty-one years, respected professor of history and economics Donald N. McCloskey decided to cross the gender line for good. Risking an extremely successful career as a distinguished academician, a prominent position in his community, and the love of his wife and family, McCloskey came to the realization that “I can be a woman. . . . I am a woman.” From this point on, through numerous expensive and invasive medical procedures, rejection by his wife and family, and more than one attempt to have him institutionalized, McCloskey never wavered in her determination to transform herself from Donald to Deirdre. This memoir chronicles this often harrowing, but also exhilarating “crossing,” which took place from 1994 to 1997.

Although McCloskey’s decision to change genders appeared to emerge full-blown from nowhere to all but her wife, in reality she had been wrestling with issues of gender most of her life. She describes her privileged childhood as the son of a Harvard professor and opera singer as normal and happy, although she was a bookish child, and a stutterer. However, what no one suspected was that the young McCloskey loved to dress in his mother’s clothes. As a teen, he went so far as to break into neighbor’s homes to try on the crinoline petticoats of their teenaged daughters. She recalls that as a boy, her two most fervent wishes were to lose her stutter and to be a girl.

However, McCloskey successfully buried this childhood wish to be a girl and became instead a very typical adolescent male. Having grown to be a big-boned, strapping 6-footer, he was elected cocaptain of the football team at boarding school, and on one level was quite content being a young man. On a deeper level, however, the wish never left him; he continued to cross-dress when he could and was fascinated by stories of cross-dressers and transsexuals. He considered himself a heterosexual cross-dresser, a not uncommon phenomenon, and married in 1965. He confessed his cross-dressing to his wife three months into the marriage and continued to cross- dress an average of ten times a month for the next thirty years. His wife, although unaware of the frequency of the activity, tolerated the cross-dressing as a barely acceptable aberration.

Two events coincided to cause a rapid acceleration in McCloskey’s cross-dressing: Both of his children left home, and he discovered the Internet. He spent hundreds of dollars in phone bills chatting on cross-dressing bulletin boards, learning about local organizations and places to shop. Even as he denied it to himself, his interest in cross-dressing took a more serious turn as he began shaving his legs, painting his toenails, dieting, and finally, going to meetings of other cross-dressers. His busy schedule of academic conferences and seminars allowed him to meet cross-dressers all over the country, and dress as a woman in public far away from his family and friends. He began to research electrolysis, female hormones, and surgery, and finally, one August day in 1995 on the toll road between Aurora, Illinois, and Iowa City, Iowa, he realized that he no longer was simply a man who enjoyed dressing as a woman; he wanted to be a woman. Indeed, he felt his real identity was that of a woman, and he needed to change the world’s perception to match his reality.

Once McCloskey’s intention to become Deirdre was announced to his family and to the world, his crossing began in earnest. He started taking female hormones, began serious electrolysis, and made plans to have facial surgery to make his face more feminine. While his colleagues and peers in the academic world were for the most part sympathetic and supportive, his family, with the exception of his mother, was not. His wife filed for divorce, and his children refused to see him. His sister tried, on more than one occasion, to have him committed, claiming that he was in a manic state. In November of 1995 his sister and a former colleague used civil commitment procedures to...

(The entire section is 1646 words.)