Transgender fiction

10+ classic transgender novels

Lettie Zeste


How did we arrive at the current twenty first century transgender narrative? I had srs 40 years ago when nothing was settled. Below are some of the novels that informed our thinking at the time. Many were available only in French, or had to be specifically requested (embarrassingly)  at a library desk. Some were only available in obscure bookstores shelved next to Sufi texts.  This list is in no particular order and focuses on MtF issues with a few exceptions.

I hope that my comments do not seem flippant. Though some of this fiction is hard to take seriously, all of these works raise important gender perspectives not currently part of the narrative of transgenderism.

So here are some gender novels predating the term transgender.

“And I know it sounds crazy but I came here believing — no not really believing — but hoping maybe, maybe somehow crazily hoping! — that some producer would see me, think I was Real — discover me!– make me a Big Star!”

Rechy, 1963


‘We come from a strange tribe, you and I.’

Ernest Hemingway to his transgender MTF child ‘Gloria’ (1950’s)

‘She came upon us without warning. Having drunk her tea, Divine, with indifference (so it appeared, seeing her), wriggling in a spray of flowers and strewing swishes and spangles with an invisible furbelow, made off, lifted by a column of smoke, to her garret, on the door of which is nailed a huge discolored muslin rose.’

Genet, 1943


  • Our Lady of the Flowers. Genet. 1943. Genet renders the sordid into lyric prose. Divine,a prostitute,  is perhaps the first recognizable uncompromising MtF in the canon of Western literature.  Genet was the first to use female pronouns for a natal male who seemed female to him.                            Sometimes the enormity of our choices gets lost in our age of established ‘gender clinics’. Here, gender is sui generis, not purchased or affirmed. Divine is male and female, not alternately expressed, but swirled together. Genet wrote this in prison. A different era, but less than a hundred years ago. [Read the opening section where Divine appears magically on the streets of Paris, with no past, no referents at all.]


  • City of Night. John Rechy. 1963. Rechy’s gay classic has sections describing ‘queens’ that are delightful because these girls come off as very unique and individual women. Rechy has an obvious sympathy and sees more diversity in this community than many more-modern writers. These are real people, at the very bottom of a society that damns them; people of character, who refuse to desist. [Look at the Miss Destiny and Mardi Gras sections.] Also, provides hints at the roles of childhood sexual abuse on gender identity and sexuality.


  • The Angel and The Perverts. Lucy Delarue-Mardrus. 1930. It is Paris of the 1920s with secret social sets of gay men and lesbians. An intersex woman/man swings between being a lesbian and a gay man. This book may be more relevant to today’s FtM scene than to much of the prior century. Thought provoking and not easy to dismiss. Our identities do involve choice.


  • Spendora. Edward Swift. 1978. A classic of passing. Captures the sense of being behind a pane of glass that many boys experience the first time they successfully pass as a girl.     Presents a dreamlike vision of trans-ness that involves hiding a deeper self. The sense of a gulf between apparent self and inner self expressed poignantly.


  • Mlle. De Maupin. Theophile Gautier. A French classic in which a woman wanders between genders, revealing herself as a lesbian in the end. The main issue is that she wants to infiltrate the world of men to understand them (and perhaps pick up some bedroom technique.)      Gender here seems immutable, with the sexes rigorously separated, mostly by social convention. It is in this novel that the concept of a ‘third sex’ is introduced. One is not born into Gautier’s third sex… one bravely creates it. Many societies have culturally preordained third sexes. But the West has resisted. Even today in America, trans issues are mostly seen as male or female. Not ‘other’ or ‘both’. Gautier sees his character as ‘really’ as a blend of genders, who occasionally pretends to be a boy or a girl out of expediency. Genet sees only two possible genders and his character fluctuates rapidly between them, sometimes within one paragraph.


  • Myra Breckinridge. 1968.  Gore Vidal. A dated and cruel transsexual novel, yes. But still relevant in its observations of the construction of gender. Gore Vidal ignores gender identity completely, but he reminds us that lots of other things make up gender besides identity. He sees gender roles as constructed, but constructed by the cacophony of adult society, not the serenity of the nursery. At times Myra seems to enjoy hating men more than she enjoys being a girl.    Vidal is exploiting gender, but has something to say about it too. Here, and in ‘The City and the Pillar’, he is outraged (Outraged!) that straight men won’t date him just because he is a man (but would if he changed sex). Cultural values matter in gender; he has that right.


  • Miss High Heels. (late 1800’s) No transsexual in the history of gender reassignment therapy has claimed, to their psychiatrist, that they wanted to change their sex from reading this book. Some have lied. Rumored to have been written in the 19th century by the renowned psychiatrist Krafft-Ebing (Psychopathia sexualis), the story is a straightforward sex fantasy of a young boy forced to become a young lady by cruel aunts. Gender identity is just a masochistic fetish here, but fetishes (which are just personal autistic compulsions) can be potent movers.    It can be a bit distressing to read fiction apparently written by victims of child gender abuse, that idolizes the abuser.  Men who like being men do not read books about cruel aunts who force a young boy to play baseball and learn auto mechanics. By the way, besides this novel, Krafft-Ebing is known for founding the field of sexology and ‘proving’ that masturbation inevitably leads to ‘moral insanity’ requiring life-long institutionalization. Just a little warning… about sexologists.


  • Sarah. J.T. LeRoy. This entry covers a glamourized version of child trans sex work. It feels as if it were set in the 1950’s. Emotionally, it is nothing but lies layered on lies. But then you have to ask yourself, who would write romantically about child trans sex work? I do not care who wrote this book. At the bottom layer, there is a person with a story to tell us, a fable. Like Miss High Heels, gender is a fetish here; but now the enforcers of gender are ‘men and sex’, not ‘women and love’. Childhood trauma, distorted and re-enacted as adult pleasure can have a profound effect on gender choices. Both ‘Miss High Heels’ and ‘Sarah’ portray transgenderism as a form of pleasurable masochism.


  • The Garden of Eden, Ernest Hemingway. Though this is not strictly a trans book, the master of macho prose (who, curiously was raised as a girl)  here reveals his secret love of gender reversal (not published in his lifetime). Hemingway says things about gender and bi-gendering not, to my knowledge, ever said anywhere else in the literature. Consider the sensuous hair-cutting scene where the protagonist’s wife has her stylist, stage by stage cut her hair from feminine woman, to boyish girl, to foppish boy to as masculine a boy as her husband is. With a few snips she becomes a man (at some level).Garden of EdenIncidentally, or not, Hemingway’s son, a lifelong crossdresser, had sex change surgery at age 63. Hemingway wrote to his child: ‘We are a strange tribe, you and I.’ Hemingway and Genet are both superb writers capable of describing mixed genders, though they filter those genders though different sexualities.


  • Last Exit to Brooklyn. Hubert Selby, Jr. 1957. In the 1950’s and 1960’s the prevailing medical narrative for transsexuals avoided the idea that trans-people needed relationships. This book, written in a time before surgery and hormones were generally available, looked at the lives of gender-nonconforming queens who could not change their bodies or their hearts.     The novel is bleak, beyond bleak, but in the world of Hubert Selby Jr. a more or less normal man could be attracted to, and fall in love with, a feminine gender-nonconforming boy. Public gender non-conformity was possible, though at a great price. [Look at, ‘the queen is dead’ and ‘Strike’.]


  • The Extra Man. Jonathan Ames’ fiction annoys me no end. He likes to be a bad boy. But this is one of the most honest descriptions of a ‘Trans-fan’ that I have found. It’s not pretty, but this is the material that many a trans girl must work with in an attempt to form a relationship. Not all transamorous guys of this type are as creepy as Ames, but most also have less self-insight. Ames shows the trans-fan as just as conflicted and blurred as a trans woman, but closer to maleness. Perhaps we need each other. Do these men belong to the LGBT community? Read and decide.


  • Orlando. Virginia Woolf’s delightful hypomanic classic is much favored by Gender Studies classes since it pretends to challenge gender, while actually doing no such thing. Perhaps the most central theme is the way in which sexuality can remain the same as gender identity fluctuates. Orlando maintains, his/her role, changing gender identity as necessary over the ages while his/her behavior changes not a whit. The question here is what matters? Gender role or gender identity? This whimsical approach is more successful for time travelers than those with one life to live. Most trans people don’t have the option to be as passive about gender as Orlando. But the story is fun for those who are ‘gender fluid’.


  • Almost. Lettie Zeste. Out of hubris, I will include my own book. Almost is a transsexual romantic-comic coming of age novel based loosely on Jane Eyre and set in the transitional 1970’s, between the early days of transsexuality and the current wave of transgenderism.     Betty Jo is just a person trying to find a way to live and love. In the beginning, gender consumes her. In the end she doesn’t even care about gender. She just wants love and a happy ending. Charlotte Bronte and Jessie Fauset  scandalized by refusing to end their novels in tragedy. They are my mentors.  Like Genet, Hemingway or Gautier, happiness is a comingled gender.


  • Eva Luna. Isabel Allende includes a transsexual in her magic realism novel who captures the glamourous queen style of gender women. She is set, not so much in relationship to society, as in relationship to a perspective on life. Allende’s sense (in this particular novel) of life being a collection of exotic events, of life being life as imagined by a storyteller, disconnects gender from the ordinary. Life is not dull and constrained by biology, religion, society, inevitability. Life and gender exist in a rainforest of mystery. The ending of the story, including gender, can be changed at the whim of the storyteller. It is through telling stories to others and listening carefully to their stories, that we heal each other and let these stories provide meaning to trauma and chaos. Allende’s world is not easy to find, but attracts many creative gender people.


  • Southern Discomfort. Rita Mae Brown gives us the transwoman as sex worker, but in this case, a small town sex worker, living an ordinary life. Sex work has been the default occupation for trans women since the beginning of time, in nearly every culture. In many ways, this is one of the simplest and truest portraits of a transgender woman in literature. And it is not tragic. However, it maintains the trope that trans women are ciphers that, even more so than ordinary women, are not understandable and have only the vaguest of internal lives. Trans women ask for this role by hiding and passing; by being all surface. But that doesn’t mean that novelists are obliged to hide their characters, even if the characters want to hide.


  • Trouble on Triton. Samuel Delany. Though I am avoiding science fiction here, I will include this thinly disguised description of NYC collapsing into anarchy in the 1970’s. Delany’s character Bron, is free to do anything on Triton, aka Harlem, 1974 (or the internet of today). He is unsettled as a man, and later unsettled as a woman. Freedom does not assure finding a comfortable way to live.  Delany’s characters are free from cultural influence, but must still live in a world where other people exist. Despite the sci-fi setting this is a realistic portrayal of gender/sexuality confusion… perhaps not resolvable.


  • Killer in Drag. (n.d., 1950’s) Ed Wood Jr. in this and similar books manages to upend and delight in bending gender roles. It is interesting to speculate where transgenderism would be today if Ed Wood, instead of Virginia Prince (who invented the useful, but bland and mysterious term ‘transgender’) had won the hearts of American CD’s. Wood gives not the slightest apology for treating gender as fetish (a personal autistic obsession, not necessarily sexual), and fetish as just one more of the delights of life. Wood centers responsibility for role and identity on the internal desire of an individual.     Society and other people can be ignored (though social norms lurk dangerously in the background). In this world a pansexual transgender woman might enjoy sleeping with a man and then, well, umm, killing him for the mob.  Despite its 1950’s noir tone, ‘Killer in Drag’ is probably the earliest antecedent of popular modern transgender fiction of the ‘boy becomes girl and goes out into the world’ type. Wood, Delany, Allende and Vidal describe gender variation in spaces that do not overlap each other at all. These authors haven’t the slightest interest in the dominant medical narratives about transgender/transsexual/homosexual individuals, but nonetheless speak to many people in the gender community. In some ways Wood is closest to Genet in resisting the influence of social norms. The individual acts.


  • Drag Queen. Robert Rodi. I don’t really believe that this fluffy farce has anything to say about gender at all. But that is the point. Twins separated at birth, one a respectable straight-acting gay man the other… (well it is obvious). Almost all of the fiction on this list, depressing or upbeat, shares an underlying assumption that ‘gender is serious business’ and society will move to enforce gender conformity. Here, those rules and that enforcement is satirized. What a relief.


  • Nightwood. Djuna Barnes. (1937) This novel captures the chaos of gender unmoored to any firm ground. The cross-dressing doctor is a phantasmagorical creature, memorable and haunting. Many people trying to live a life unbound by any defined gender will recognize themselves or the people around them in this challenging and fluid work. The space that Barnes describes is hard to occupy for long. Absolute emotional freedom is painful. Society is not kind to these people either. Lovely prose, but preverbal gender conflict may respond better to antipsychotic medication than to estrogens


  • The Left Hand of Darkness. Ursula LeGuin. Several readers have suggested that I include this title, and I agree. Though I have avoided science fiction, in favor of lived experience, this novel had an outsized influence in the past and still speaks to those who alternate sexes/genders today. Also this list lacks talented female authors like LeGuin. Unfortunately, LeGuin has acknowledged that the protagonist of this novel about a species that cyclically changes sex is written mostly in the male voice. That is, male entitlement is not really lost in the female state. Of course, that is also true for many of the other works on this list. For a darker, more troubling cycle of sex change in the real or dissociated world look to Emma Tennant’s ‘The Bad Sister’.


Other Books of interest

  • The Scarlet Letter. Nathaniel Hawthorne. This still the best vision of ‘proud shame’ ever written, in my mind. Hester Prynne is every person hypocritically stigmatized by the tyranny of the majority. She shows a path towards dignity and self-worth in the face of public discrimination. A must-read before transition! The Reverend Dimmesdale represents all the men who love trans women, but won’t bring them home to their family, all the CDs and feminine men who lurk and fail to publically support transgender rights. They are not evil, but Hester is braver.


  • Keeping up appearances. Rose Macaulay. I have to include this book which is about a woman creating a new (better!) female identity for herself. The reason that I am putting it here is for balance. Macaulay shows us an unexplored dimension in gender-change fiction. Like several of the novels above, there is a new, constructed identity and self. There is plenty of passing as a different person. But both people are female. Macaulay shows us the hazards of trying to be someone other than yourself, independent of gender issues that might be involved. No surgery can change your personality. It is easiest to just be yourself.


  • The cards of identity. Nigel Dennis. (1955) A prescient, flippant, sardonic look at how external authority can define identity, including gender identity. A novel for anyone who thinks that they are ‘really’ a woman, because their passport says they are, or their therapist has ‘affirmed’ that they are. Alternately disturbing and funny.


  • Plum Bun. Jessie Fauset (1928). Novels about ‘Passing’ are surprisingly absent in Western literature, though this issue is important to trans people. The best ones come from the Harlem renaissance when a drop of African blood stigmatized (has this changed?). The subject of passing is controversial, but clearly relevant. This is the best novel to my mind, though Nella Larson’s ‘Passing’ provides a counterbalance, for those who disapprove of passing. Goffman describes passing as hiding stigma, which for trans women means obscuring a significant part of themselves. Long before ‘Bathroom laws’ trans women were swept off the street for ‘female impersonation’ by police. That is, trans women that the police could detect were swept off the street. For most of the  novels on this list there is little attempt to pass (exceptions, ‘Almost’, ‘Southern Discomfort’, ‘Splendora’ and ‘Killer in Drag’). The issue is not simple. Fauset lays out the complex emotional aspects of passing clearly. This is a lovely book for those who not only feel feminine, but would like to actually live ‘as a woman’, not ‘as a trans woman’.