The Charlotte Chronicle - My Experience as a Crossdresser [Part 1]

Feature Article

Writer: Charlotte

Part 1 of 2

“If you could press a button and instantly become the opposite gender, would you press the button?”

Maybe you’d say no. That’s cool. You’re valid for being comfortable in your own self. But for some, I’m sure the thought has flitted across your mind. Nothing too serious, but still present: the curiosity to present as the opposite gender, or something else entirely.

I am Charlotte, I am a crossdresser, and this is my story.

ORIGINS

My first crossdressing experience started as a stereotype. As a child, I wore my mother’s clothes, and she scolded me. Quite Freudian, isn’t it? Simple, easy to imagine yet difficult to understand. My mother must have thought me a freak back then. (Spoilers: she still does now.)

And yet, something must have worked in her scolding. I forgot about crossdressing or the desire to become a girl as I finished primary school, entered an all-boys secondary school and served the nation for two years. My life was standard boy stuff, with no space or time for a girl who didn’t even have a name.

Charlotte’s second coming was unexpected. It was the day of my Econ final (I won’t mention the module), and I had crammed into my brain an entire whiteboard’s worth of equations. Amid all that studying, I needed a break, and watched a video from Philosophy Tube. (Yes, I do weird things with my study-rest routine.) In the video – spoilers, again – the host, Abigail, mentioned she was a trans woman, which really shocked me. She was so pretty that I couldn’t tell! Perhaps, she was the first trans woman I’d ever seen. I’d only seen caricatures of trans people before that, after all.

And, out of that initial reaction, the most important question: could that be me?

I carried those thoughts with me into the exam, struggling with thoughts of whether I was meant to be in this male body, while solving for total cost and marginal revenue and all that Econ knowledge. Between that, and my laptop dying on me halfway through the paper, that was probably my most memorable exam.

The thought of becoming female stuck in my mind for an entire semester thereafter. I had no idea what to do with that until my Residential College (RC) launched the theme of our farewell dinner: The Great Gatsby. It was my favourite book while I was still studying Literature at A Levels, so I had fond memories of the theme. Yet, I thought suits were getting boring, having worn them all my life… what if I wore a dress instead?

After preparing my makeup as best as I could, I slipped on a black maxi dress and strolled into Kent Ridge Guild House. I was dressed as Jordan Baker (a character from The Great Gatsby), but with all the stares I felt on me, I might as well have been Cinderella.

(My first cross dressing experience!)

So, there you have it. Charlotte’s origin and rebirth: a journey that took nearly 13 years to start. The ship’s in the water and it’s still sailing.

And why the name Charlotte? That comes from my favourite Instagram crossdresser – Charlotte February – and the novel Charlotte’s Web, where a spider rescues a pig from being slaughtered by weaving messages into her web. I admire her ingenuity: both the crossdresser’s and the spider’s.

DEVELOPMENT

I can’t deny it: it felt good to be noticed as Charlotte. Something just felt right about dresses and makeup that “male clothes” couldn’t provide.

Still, I was not ready to be a girl full time. I pondered the relationship between Charlotte and her male-at-birth body: was Charlotte a werewolf, only available at a certain time every month? Or was she a female Hyde to my male Jekyll? All very negative depictions: every thought I had of crossdressing was tinged with shame.

Those feelings came to a head when I went for Pink Dot 2022. The first half of the day resembled a well-planned heist mission. Leaving home in a singlet and shorts, I procured a dress from a friend that I could still wear my male clothes under. When I reached the MRT station, I was very worried about wearing the dress: which toilet should I use? Would it be okay if I entered in male clothes and came out en femme? My face didn’t have makeup on it, would I look presentable?

And it was under the blazing hot sun at Hong Lim Park that I realised: it all didn’t matter. Pink Dot was a space for me to be myself, to be Charlotte. With everyone there accepting themselves and others for who they were, it was time for me to learn that too. It didn’t matter that I probably didn’t pass, that I still thought I didn’t look good: what mattered was that I felt good. With that thought in mind, I’d never been happier to dance to ABBA music.

(I need to go find that fan again...)

Charlotte has developed in other ways, aside from dolling herself up. I’ve met other crossdressers: Isabelle, who runs her own blog, provides a far more in-depth exploration of what it’s like to be a crossdressing adult. It’s especially interesting how Isabelle and I have varying views of the stigma against crossdressing and hiding our female selves, which she has written about here. I’ve also met trans women whom I can share experiences with, be it the latest 11.11 sale for dresses, or more in-depth thoughts about transitioning.

The Internet has also been a great help in my exploration. I’ve watched so many videos from Philosophy Tube and Contrapoints: they obviously write their experiences as trans women into their content, but the philosophical content in their videos are valuable to everyone. The Twitch streamer F1NN5TER (aka Rose) crossdresses while streaming Minecraft and interacting with his fans. Watching him have fun in “girl mode” is everything I’d want if I started a YouTube career.

(He's really goals, how does he look so pretty???)

So, as much as being Charlotte is unconventional, it has been one of the most exciting things I’ve done. Even if I still present as male 95% of the time, the itch to transform into Charlotte will always be there, and I am glad that I still have the chance to fulfil it.

But growth usually comes with suffering…

Stay tuned for the next part, where I go into depth about that. While you’re waiting, do check out The Charlotte Crisis, a visual novel I wrote for NM3222 Interactive Storytelling!

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Note from CNM Types: Thank you Charlotte, for such an insightful and interesting article. Keep your eyes on this page everyone for part two!