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  • Writer's pictureClairene Tan

The Charlotte Chronicle - My Experience as a Crossdresser [Part 2]

Feature Article

Writer: Charlotte

Part 2 of 2

(This is the second part of The Charlotte Chronicle. Read the first part here!)


Charlotte’s journey has not been all sunshine and rainbows. (Sunshine makes my makeup melt, anyway.) I will highlight three sources of opposition to Charlotte, in order of increasing distress and hurt to me.

The first incident was a one-off confrontation with a cleaner at McDonald’s. I had just gone shopping in girl mode, and was having dinner, when the cleaner came up to me and compared my gender identity to a neutron. (“Proton is male, electron is female, you are neutron.”) He shuffled away and passed by once more complaining under his breath about the government’s tolerance of LGBTQ folk.

It was a bizarre experience that made me feel very unsettled. Why did he have to come up to me like that? Couldn’t he keep his opinion to himself? I declared that I’d never bring Charlotte out again, but thankfully I overcame that hesitation once more.

Around the same time, I started to find out that one of my colleagues, K, was transphobic. Fed on Joe Rogan podcasts and a very specific interpretation of George Orwell’s 1984, he was convinced that “social justice warriors” (SJWs) and anyone fighting for LGBTQ rights were the enemy. I knew at that point that I could not tell my colleagues about Charlotte. It would cause unnecessary debate that I was not ready for. After all, they were paying K lip service too.

And yet, the situation is more complex than merely “my company is transphobic!!”. I reached out to my supervisor for advice when I felt hunted down by my family for crossdressing (more on that later), and he was empathetic to my situation, explaining how he’d also had to deal with conservative parents. He also advised that I stand up for myself against K if I felt very offended. My colleagues also debated the merits of playing as a female character in role-playing games, which was an interesting discussion that thankfully didn’t turn transphobic.

At time of writing, my time with this company is ending soon. I’m glad for my time spent there, but these encounters have taught me that I shouldn’t reveal Charlotte to just everyone.

(I started playing Genshin Impact recently. For obvious reasons, my Traveller character is female.)

Related to revelations, the final, and most devastating experience was when my family found out. I had gone shopping that day and posted my pictures to Instagram. It was at that precise moment that a distant aunt logged back into Instagram and saw my post as the first one on her feed. Rumours spread around the family grapevine and my parents questioned over WhatsApp. They took a different approach from when I was young, however: instead of being mad like they were 13 years ago, they were worried that I would transition, begging for me to stop crossdressing.

Between all the messages they’d send me on WhatsApp, and the panic I felt that they’d spring a surprise visit on me at my Residential College, I felt like I was being hunted. Their efforts were a pathetic way of gaining the moral high ground, while still prioritising their wants above my own. I am lucky that my sister negotiated between them and me to keep the conversation going, because I would have ghosted those WhatsApp conversations.

Thus, after a tearful lunch at Swensen’s, I told my family that I did not want to transition, and that they would never see me crossdress again. I deleted my crossdressing posts from my Instagram account, and started afresh (you’ll get the link if you read to the end!). It almost felt like signing a peace treaty, what with all the conditions and reparations that needed to be adhered to.

Looking back on these experiences, they’re almost like different acts in a story. The inciting incident with the cleaner, the rising tension with my colleagues, and the climax against my family. There is still much external opposition to people like me, and I fight that at all levels while dealing with the internal opposition between Charlotte and the male body she inhibits.


The best way to approach this is by vigorous self-criticism and questioning.

Have I ruined my relationship with family? Perhaps. I don’t trust them as much now. I have difficulty talking to them, as they still expect to see their son, their brother, their nephew. It’ll be hard for them to change their opinion, and I think the best thing I can do is distance myself from them for now. At the same time, crossdressing is my own niche, and I don’t want them intruding on it. I think it’s in everyone’s best interests that Charlotte doesn’t see the family. As much as I want to love my parents, it’s not a good time now.

Am I trans? Not now, but maybe. This also depends on your definition of transgender: does it require gender dysphoria? I used to think so, but I was wrong: some trans people don’t feel it. Do I feel it, then? I think not, but recently I’ve noticed that I feel uncomfortable looking at old pics of myself with shorter hair… For now, I’m labelling myself genderqueer. It’s a catch all term, for I am not solely male nor female. And just as I told my family, I’m not intending to transition: hormones and surgery are too scary and expensive for me right now. (That’s just my take, though: get what you need for your own body!)

Is this a fetish? Maybe. But so what if it is? I’m not harming anyone through crossdressing. The media enjoys depicting crossdressers and trans folk as harmful: from serial killers to “traps” and a plethora of prejudiced portrayals in between. And it is time we reclaimed our identities in media: rejecting discriminatory tropes and telling our own stories.

Am I privileged? Maybe. The very fact that I don’t feel dysphoria is already good compared to other trans folk who do. I don’t have to live as an outsider in my own body: I just have the freedom to switch between male and female characters. As I type this, I’m wondering if there are more people like me out there, struggling with their gender identity to various degrees, and I should like to help them if possible. Pink Dot might be a good start.

Where do we go from here? Charlotte is very grateful for the support from all her friends: (almost) everyone in this generation of youth is at least tolerant, if not outright supportive, of LGBTQ folk. Even the professors are nice to her! She is eager to go out again, explore, and find out who she really is, be it through NUS modules or experimentation or just watching videos.

And come what may: whether I turn out to be trans, queer, or even ditching Charlotte entirely, regardless of whoever tries to attack me for being who I am, I hope that I’ll always be the one making the decisions, with full autonomy.

(I just thought this picture was funny. The stars aligned for me to stand in front of the word “Gal”)

Thank you for making it to the end of the article! As promised, my Instagram account is @char1otte.web. If you’d like to follow me, please drop me a message too telling me you came from the CNM Types article!


Note from CNM Types: Happy new year everyone - we hope everyone is well. Thank for reading this far and showing your love and support to Charlotte and us here in CNM Types. As 2023 approaches, be sure to look out for more of our upcoming articles. Also, while you're on the app following Charlotte, why not drop us a follow as well :D

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