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Rosemaster, Cucumber Quest (2011-)
[This post contains spoilers for: Cucumber Quest]
A well-documented problem with certain representations of trans people in media is the tendency to pathologise their actions and imply that their transness is at the root of their problems and wrongdoings. Their transness is written as something that is inherently entwined with their ‘evilness,’ or is otherwise intended to incite disgust in the reader. The trans person is often cast as a singular anomaly within cisgendered society, a site of constant correction and revision whereby the story of the trans character is resolved through their sanitisation or ‘passing.’ To me, trans villains represent an extremified version of this narrative. They represent the total failure of society to sanitise the trans body. The trans villain is militant and aggressive resistance against cisnormativity. In this light, and in an age where non-normative bodies are regularly in danger of being criminalised, devalued and even killed, I think there’s plenty of ground to write trans villains with storylines that are pro-trans. The problem is that due to a lack of sensitivity towards trans issues, representations of trans villains (and trans characters generally) can often come across as supporting cisnormativity, even when the authors didn’t necessarily intend to be transphobic or reinforce negative stereotypes.
However, this doesn’t mean that writers shouldn’t write trans villains. What it means is that writers need to ask themselves if their villain’s transness is doing something other than simply and uncritically alienating the character from the reader. Does the villain negotiate their transness and disclose it to other characters on their own terms? How do other characters react to the character’s transness and what sort of message does this convey to the reader? What problems and challenges has the villain dealt with as a result of being transgender? Most importantly, is the villain’s story relatable to trans readers? Trans narratives and trans people’s experiences have a lot to offer fiction, and writers shouldn’t be afraid to explore this area, and this extends to the concept of the villain.
Let’s take a look at Rosemaster, a brilliantly complex villain from the web comic Cucumber Quest (2011-) by Gigi D.G.. Rosemaster is the central villain of Chapter 3, and large parts of the chapter are dedicated to her character development. She is one of the Disaster Masters, a group of villains created by the Nightmare Knight. The Legendary Hero must defeat each Master to retrieve signatures from princesses which, once collected, will allow them to face the Nightmare Knight in battle. The storyline is somewhat of a deconstructionist take on fairytale and video game tropes, subverting them in refreshingly progressive and novel ways.
page 524
The first and only clear allusion to Rosemaster’s transness is a page early on in the chapter where Nautilus, one of the protagonists, is talking to Rosemaster about a legendary Master named Thornmaster. Rosemaster explains that she is actually the Master in that legend. Nautilus realises that Thornmaster was Rosemaster’s old name, apologising for inadvertently misgendering her.
page 540
Note how the disclosure of Rosemaster’s transness isn’t portrayed as a shocking deception. It is handled candidly without fanfare and Rosemaster is allowed to articulate her own expressions. She isn’t outed by another character, and Nautilus doesn’t react negatively to the revelation. We also learn that Rosemaster was a villain before she came out, suggesting that her villainy may exist independently of her being trans. All this helps towards humanising Rosemaster and developing her character positively, and these kind of considerations when introducing a character’s transness are imperative for setting the tone of the character’s receival with the reader.
Rosemaster has mind control powers that she can use on characters that share a name with a flowering plant (a considerable portion of the cast falls under this category). A fan of Cucumber Quest expressed concern that as trans people often rely on regulating their own names for their safety, having Rosemaster manipulate others through their names implies that trans people are deceiving others when they regulate their own names out of necessity. Trans people who choose to go by a name that isn’t their birth name go through unnecessary humiliation when they are legislatively required to use their old name, and many trans people do not feel safe to use their preferred name at home, at the workplace, or anywhere else.
Highlighting the negative connotations of Rosemaster’s manipulative powers is a valid contribution to discussion surrounding her. But given the general sensitivity Didi D.G. has shown elsewhere towards Rosemaster inside the story and outside, I do doubt that she intended this reading. Rosemaster’s ability could just as easily be read as a pro-trans gesture of flipping the tables on cis people and showing them what it is like to be held hostage by their names. We also discover that her minions work for her not because of being brainwashed but because they like her kind nature and have formed a genuinely intimate bond with her. She does not depend on mind control for other characters to respect her as an openly trans woman. When it comes to her identity, there is certainly no deception whatsoever.
page 667 (excerpt)
The final part that I would like to talk about is the several stages of physical and emotional transformations that Rosemaster goes through towards the end of the chapter. After receiving a flower that has the ability to multiply one’s magical powers, Rosemaster transforms into Super Rosemaster. In this form she faces the story’s heroes in battle.
page 620
Transformation naturally evokes strong bonds with transition, a concept deeply entwined with trans life. Whether physically or emotionally, transition forms a profound personal narrative through which trans people come to terms with their own bodies. As J. Skyler notes in an article about Mystique from X-Men, the fantastical allure of shape-shifting can provide a sort of escapism for trans people.
At the very end of the final battle, we see a flashback where Rosemaster has a conversation with another Disaster Master. Chronologically, this seems to happen immediately after she uses the flower to transform. She appears in her ‘true’ form, a beautiful persona that is perhaps her ideal image. This is quite crucial, as it shows that her Super Rosemaster form is just a front put on by her for the heroes so that they feel like they are fighting an evil force.
page 650
It’s in this true form that she comes to accept the situation she and the other Masters are in, and expresses faith in the Nightmare Knight even though his convoluted plans appear to betray the Masters. It’s also hinted that this may be because the Nightmare Knight accepted her transness, and maybe even gave her the power to transition initially. It’s through her transness that she comes to understand the way out of the agonising cycle of defeat the Masters have suffered for thousands of years.
page 652 (excerpt)
In summation, Rosemaster is a great example of how a trans character can be written intelligently and positively, even when they play the role of a villain. Her arc is concerned with themes of identity, transformation and self-discovery/acceptance. We also see her facilitate self-discovery in other characters in the chapter, such as Sir Carrot (wow!). Despite what we assume villains to be, she has a loving side and is deeply concerned with the feelings of those whom she holds close. Her transness is never used as an excuse for evil. On the contrary, her experience of being trans amplifies her empathy and moral judgment. Rather than her transness reducing her to a one-dimensional punching bag for transphobia, it complexifies her story and makes for an enthralling read.
Hopefully this post will have shed some light on analysing Rosemaster, and how to write interesting and dynamic trans villains. Of course, this is just one example of what I think is a well-written trans villain, and I certainly haven’t exhausted every avenue of how one can be written. If you have any other trans or gender non-conforming villains that you think deserve recognition (or criticism), please send me a message. Thanks for reading!
image by tumblr user lohrs.
all other embedded images by Gigi D.G. and taken from http://cucumber.gigidigi.com/.

Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
Free to watch • No registration required • HD streaming

Anya is live and ready to show you everything. Watch her strip, dance, and perform exclusive shows just for you. Interact in real-time and make your fantasies come true.
Free to watch • No registration required • HD streaming
Brian Waugh - Last Castle