Yet perhaps Dolores was not infinitely malleable, infinitely subject to Vollmann’s will, after all: “She expected to look beautiful, posed with what she fondly supposed to be a come-hither look,” Vollmann says, but, when he looked back at the pictures, “I felt embarrassed on her behalf”: despite the breasts, the glasses, the makeup, Dolores still has the round, not especially athletic face and body of a “wall-eyed, jowly man of late middle age.” Vollmann sees his body in her, but not his own psyche: he gives her, always, the grammatical third person. “How many times has Dolores imagined herself to be pretty, only to inspect her portrait with her spectacles on?” “I would have liked to photograph her nude,” he adds, but “Dolores nude would have been nobody other than myself.” Poor Dolores cannot, after all, meet her creator’s standards of beauty, cannot become somebody whom William T. Vollmann finds erotically attractive. That mismatch means that, to Vollmann and to others, “pictures of her tend to look ‘sad,’ ” even though “she may well be more gleeful than I.” It is a sadness not entirely alien to me or to some other transgender people, who are—like everybody else—limited in how we can change our bodies, how much we can do to make the outside match the inside, even if the limits are more permissive (and our friends more accepting) than we once assumed.

Vollmann’s prolific career (at least twenty books, some enormous, in twenty-five years, including that National Book Award winner) and his logorrhea-ish prose style speak of a man determined, as he says, to resist the reality principle in favor of “self-assertion and aggrandizement.” “No one is utterly free from vanity or anxiety, but in my own various projects I resist defining myself on the basis of others’ judgments.” Trans people of all sorts, including my sort, resist Freud’s reality principle, too: we want to be, or try to be, or feel that we already are what our birth families or society claimed that we were not. And so it is no surprise that Vollmann, having circled the globe and delved into slums and war zones, should return, in his challenge to norms and social limits, to the limits around his own male body. Whether or not it turns him on, whether or not it makes him feel more like, or better than, himself, becoming Dolores in words and images gives Vollmann one more way to say that his own world is what he can make it.

Vollmann’s cross-dressing—unlike, say, the comedian and actor Eddie Izzard’s cross-dressing, or mine—is not an expression of deep identity (it is not something he has always done, nor something he always wanted to do) but something he seems to have done on a dare; having explored the mountains of Afghanistan, the red-light districts of Phnom Penh, and the polluted croplands of Calexico, Vollmann finds a new adventure in dresses and wigs. He cannot, he writes, “know what it is like to be a woman,” but he can “perform femininity for myself.” And why not? Like me, he won’t be fired, or even stigmatized, let alone physically harmed, for cross-dressing (though every year—as he must know—many people still are); like me, Vollmann works in a field where you can embarrass yourself without much professional penalty, as long as your audience still likes the language you use. There is nothing morally wrong—though nothing morally praiseworthy—in drag per se; when a man so invested in straight male desire as Vollmann tries it on, and describes how he feels with prolix honesty, the results may be creepy or charming, or both.

What’s sad here is how much he seems to have done it alone, without even trying to figure out how other cross-dressers or trans people, or their communities or their literary precursors, might help: sometimes he talks without listening. When Vollmann is not explaining the processes by which he made Dolores into visual art, or explaining how “The Book of Dolores” interacts with the Mexican novel, he is explaining, or mansplaining, life in general: “People often get crushed to pieces between the grindstones of conflicting realities, as did the Poles during the Nazi-Soviet Pact.” Vollman has a thing for autodidacts and big thinkers: his prose here refers to Herbert Marcuse and to Gandhi, to Thoreau, to Dostoyevsky, to photographers from Man Ray to Steven Livick, but not (unless I missed it) to anybody before him who has spent any time thinking about what it means to reject the gender in which you grew up.

Vollmann writes about his imaginary Mexico, at least in “The Book of Dolores,” without any sense that Mexican people will read it. And he writes about his own cross-dressing, his own re-incarnation, as Dolores without conveying much sense that other writers and artists interested in femininity, in drag, or in unstable genders (Simone de Beauvoir, Imogen Binnie, Kate Bornstein, J. Jack Halberstam, Eddie Izzard, Cindy Sherman, Virginia Woolf) have been there before. There’s nothing like, for example, Bornstein’s observation that “a newly transgendered person … moves just a bit slower than most people,” since “he or she is unlearning old ways of moving,” nothing like Bornstein’s jokes, or Izzard’s jokes (you can find them on YouTube), or Bornstein’s or Halberstam’s reflections on what we can learn by failing to pass. “The Book of Dolores” reflects—as Vollmann usually reflects—honesty and energy, but it also suggests a failure of research, even a failure of imagination, along with a coy defensiveness about remaining a straight man on the inside. Dolores has a “lesbian lover Isabel. What they do together I can’t imagine.” Really? (Why not ask a lesbian?)

Vollmann sounds far more confident, and says far more, about the photographic process than about the kinds of work—with cosmetics and clothing—that go into performing femininity, even when the performance is (like my own) inexpert, occasional, amateur. A sentence that sprawls over most of two pages explains how Vollmann, in propria persona, can “stride grandly into the light, insert the holder in my 11 x 14” camera, “pull out the dark slide, remove the lens cap, start my kitchen timer, direct obedient Dolores to run and instantaneously composed herself upon that chair over there on which I previously focused, encourage her to remain still,” and finally develop her photograph. “What an education in life gum printing is!” he exclaims, and he takes pains to educate us: “Quidnacrone gold and amethyst both achieve a remarkable tonal range in one printing; however, in four-color printing the former renders yellows as brown and the latter will degrade the separation between red and blue.”

What if Vollmann had devoted equal energy to learning, to practicing, to saying how he had learned either the study of sex and gender by the people (some of them fine writers) who have studied it before, or the practical arts of makeup and costume—the kind of thing that men can learn a bit about by asking skillful women or by watching trans how-to videos on YouTube? What if he had treated the arts of femininity with the same attention he gives to the arts of photography? Maybe he did, but his prose does not reflect it: instead, he comes off, by the end, as an anxious mansplainer, uneasy about the feminine subject he chose. Cross-dressers, trans girls, and trans women, like and unlike me, may or may not pass, may or may not think that we can pass, but we can be sensitive—perhaps too much so—to claims that we look or sound too much like men. Vollmann as a writer has no such fear.

Stephen (sometimes Stephanie) Burt is a professor of English at Harvard and the author of several books, among them “Belmont,” a book of poems (Graywolf, 2013). “The Cambridge History of American Poetry,” co-edited with Alfred Bendixen, will be published in 2014.

Photographs from “The Book of Dolores” by William T. Vollmann, published by powerHouse Books.