TRANS BOOK MONTH: Trans Stories and the Woman Disguised as a Man Trope, by EE Ottoman

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As part of Trans Book Month on Just Love, in which we are highlighting trans literature, we have invited several authors to share some of their thoughts with us. Please welcome EE Ottoman here today…

Trans Stories and the Woman Disguised as a Man Trope

I have a love hate relationship with the cross-dressing trope that pops up in a lot of romantic storytelling. Specifically the narrative of the woman who disguises herself as a man to go on adventures or otherwise enjoys some aspect of male privilege, and along the way falls in love. It’s a trope found in everything from historical romance novels, historical fiction, classic movies, television shows, romantic comedies, and fantasy novels.

Off the top of my head I can think of the Disney movie Mulan, the South Korean drama Coffee Prince, American comedy She’s the Man, fantasy series Song of the Lioness by Tamora Pierce, and Shakespeare’s Twelfth Night all of which rely on this trope.

This trope is actually everywhere and any of us can probably come up with hundreds more examples.

This trope can be used to highlight the restrictions placed on women, especially historically, or it can be used to help a woman come to terms with her gender identity.  It can allow the main character to form a close friendship or sense of comradery with a man that then often blossoms into romance; it can allow her to travel safely or flee violence. Or it can be used for comic relief (the punchline being: people assigned female at birth can’t REAL pass as men) or to make a point about how different men and women really are, thus enforcing the gender binary.

It’s an interesting trope in that I’ve seen it used to assure the audience that, yes, heterosexual, cisgender identity is the only real way to be normal, AND also used to make feminist statements about the gender binary as a tool of misogyny in oppressing of women (although usually not at the same time).

Growing up, I loved this trope. I had a fondness for people with made up identities and personas, who lived for extended periods of time pretending to be something they weren’t. The woman who disguises herself as a man was my absolute favorite.

As an adult I do still like this trope, but it comes with mixed feelings. As a trans man I cringe when the trope is used as a “women and men are soooo different!” *gag* I hate it when we’re invited to laugh at how badly the woman ‘passes’ as a man, when she doesn’t know how to walk right or how to talk “like a man.”  Passing is such a source of both anxiety and pride for a lot of people, and it hurts to see it reduced to a punchline for a cisgender audience.

Even when the trope isn’t used as transphobic comedy it can still feel a little troubling to me. My life has only gotten harder and more complicated since coming out as trans. So stories of cisgender women disguising themselves as men in order to make their lives easier has a weird, bitter taste to me. On the one hand, I do understand that, especially historically, being able to pass as a male did bring privileges; yet at the same time it can feel a little like cisgender slumming. The woman reaping the benefits of passing as male, yet always knowing she has the option of going back to living as a cis woman when passing as a cisgender man becomes less convenient.

Indeed, often when this trope appears in romance novels, it acts as a way of letting the heroine have her cake and eat it too. Dressing as a man allows her travel or serve in the military, or have wild nights at the gambling halls and all male clubs, until she meets the duke of her dreams. Then she can put back on a dress and enjoy having a legally-recognized and socially-condoned relationship… not to mention the power and privilege of becoming a duchess.

While any trans man falling for the duke in that particular scenario would have an infinitely harder time of it.

Writing this as a cisgender woman-focused trope, to me, isn’t innately wrong or transphobic. In fact I think it can be quite interesting; but I do think there is an element of cisgender privilege that is almost never addressed. As well as a lot of trans and queer possibilities that all too often get glossed over.

Because I do really think the trope lends itself to trans stories if in a more subverted form.

What if the woman disguises herself as a man only to realize he was a man all along? What if falling for another man allows him and his love interest to realize they were both queer all along?

I’ve played on this trope multiple times in several of my own books.

song of the spring moon waning e e ottomanIn Song of the Spring Moon Waning the main character, Wen Yu, is raised as a boy by his family in order to ensure he gets an education only to embrace his male identity and realize he is truly a man.

In The Doctor’s Discretion (see blurb below), coming out this fall, one of the main characters, Augustus Hill, is an ex-naval officer. It’s a direct reference to the narrative of ‘women disguised as men in order to serve in the military’. Only in Augustus’ case he is trans, and serving in the Navy helps enforce his understanding of his own masculinity.

a matter of disagreement ee ottomanAnd I definitely had the regency romance trope of ‘woman disguises herself as a man and falls for the dashing duke’ in mind when I wrote A Matter of Disagreementwhere the dashing duke (or in this case, Marquis) turns out to be trans.

The woman who disguises herself as a man as a trope is complicated and multi layered. It can be used in transphobic and homophobic ways, but it can also be used as a woman-centered power fantasy. It can erase trans identity, or it can be a tool through which a character comes to embrace themselves as trans.

Like the best, most powerful tropes, it just comes down to how authors choose to write it.

I know for me, it’s a trope I will come back to over and over again.


EE Ottoman grew up surrounded by the farmlands and forests of upstate New York. They started writing as soon as they learned how and have yet to stop. Ottoman attended Earlham College and graduated with a degree in history, before going on to receive a graduate degree in history as well. These days they divide their time between history, writing and book preservation.

Ottoman is also a disabled, queer, trans man whose pronouns are: they/them/their or he/him/his. Mostly though they are a person who is passionate about history, stories and the spaces between the two.

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Coming September 29, 2017

The Doctor’s Discretion, by EE Ottoman

the doctor's discretion ee ottomanNew York City, 1831.

Passion, medicine and a plan to break the law …

When Doctor William Blackwood, a proper gentleman who prefers books to actual patients, meets retired Navy surgeon Doctor Augustus Hill, they find in each other not just companionship but the chance of pleasure–and perhaps even more. The desire between them is undeniable but their budding relationship is disrupted by the arrival of a mysterious patient at New York Hospital.

Mr. Moss has been accused of being born a woman but living his life as a man, an act that will see him committed to an asylum for the rest of his life. William and Augustus are determined to mount a rescue even if it means kidnapping him instead.

Their desperate plan sets William and Augustus against the hospital authorities, and the law. Soon they find themselves embroiled in New York’s seedy underworld, mixed up with prostitutes, spies, and more than a lifetime’s worth of secrets. When nothing is as it seems can they find something real in each other?


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4 thoughts on “TRANS BOOK MONTH: Trans Stories and the Woman Disguised as a Man Trope, by EE Ottoman

  1. Tapas released a book with this trope earlier this year. The girl MC (cis), in order to help her family (similar to Mulan’s decision), disguises herself as a boy to enroll in an all boy’s school. She says she’s not comfortable with the idea of presenting in a way she doesn’t identify, but she’ll do it to help out her family. This is the information we get in the first chapter (nothing more, nothing less) and I was shocked and confused to see so many transmale readers immediately calling it transphobic. In my mind, transpeople aren’t crossdressers so I didn’t understand why they’d see a cisgirl crossdressing and relate it to trans identity. This article has been enlightening. Thank you.
    I still think, though, that the readers judged too soon. It may have grown to have problematic aspects like you mentioned above. But I don’t think the first chapter alone, or the theme itself automatically made it transphobic. Wanting or not wanting to present in a feminine or masculine way is something both binary trans and binary cis people face. Society and, when it’s present, gender dysphoria make the trans struggle of that more complicated and intense. To some readers, I suppose, a cisgirl expressing her reluctance to present as a boy undermines the trans struggle? I might agree if trans anything was even mentioned in the story. But it wasn’t, so what they did is kind of like me, as someone who suffers from severe mental illness, going up to a neurotypical person and saying “How dare you say you’re depressed because your dog died. That’s undermining my struggle.” As long as they aren’t stepping into my space and talking over me or creating campaigns over it (as if they’ve been shamed for centuries), I think them mentioning their own issues is fine.


    • Thank you for commenting Lena. I’m glad you found this post interesting and useful. From your description, I don’t think I’m familiar with the book you are referring to or the specific comments of the trans men who were upset by it/felt like it marginalized their experience. So I can’t really comment on the book or situation.

      I will reemphasize that to me this trope where a cis woman cross-dresses as a man is not inherently transphobic or problematic. I do think that there can be troubling aspects to it as a trope in fiction especially when it plays out in certain ways within certain kinds of fiction like romance novels.

      I think there can also be a little bit of frustration too for me and other trans men and trans masculine people that it is sooo common in fiction and other media and yet actual trans characters aren’t.

      Liked by 1 person

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