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Musings of a Singaporean Transgender


The last time I went out in public properly as Isabelle was in April 2023 for Cosfest at Gardens by the Bay. A month later my egg cracked and I started HRT. Since then I've not been in the proper headspace to go out in public as Isabelle. While I did dress up as Isabelle in a private indoor space, I felt incredibly dysphoric about my appearance when I dressed. Gone was the confident Isabelle, replaced with a terribly brainwormed baby-trans. I hated all photos I took of myself, nitpicking every masculine facial feature. I felt like a fraud; a man in a dress, unpassable even with makeup, let alone with a bareface. I stopped dressing up, partly because I was living with parents and didn't have a safe space to transform into Isabelle, mostly because it was just too painful to see that my best efforts fall short of the passing mark.

I could not see myself as a woman. Fighting inner demons on a near daily basis, I was constantly worried about whether my hair would grow out properly, impatient about the effects of HRT and facial hair removal, constantly anxious that even after waiting for a few years, I would still be unable pass. Never mind the fact that when I went out as Isabelle during my crossdressing days, I was able to try on clothes in women's changing rooms and navigate through a mall without too many quizzical stares. My brain felt a bit broken.

But as my hair grew out slowly, I could occasionally see glimpses of the woman I would become. Though I was still sporting a mullet because my fringe wasn't long enough, I felt that maybe, just maybe, Isabelle was ready to make a reappearance, this time without needing to wear a wig. Coming out to my hairdresser and having her reassure me that my hair could work despite my fringe was the validation I needed. Since renovation of my new home was also recently completed, I decided it was time to stop hiding in my shell, driving myself insane by constantly worrying I wasn't going my own expectations. If I was going to present female 24/7, I needed to get used to weird stares and uncomfortable comments from others. I decided to dress up as Isabelle for my voice therapy session and shopping at Somerset.

On the day I was supposed to go out, there was an unexpected hiccup that nearly derailed my plans, because my kid suddenly complained of pains in both her calves to the point where she didn't want to walk. It was quite worrying so I brought her to see the doctor, who did a check and reassured that it wasn't anything to be too worried about. I enjoyed a McDonald's breakfast with the kiddo before dropping her off with my Mum for the day. It was time to let Isabelle out.

I hadn't put on makeup in almost a year, but it was muscle memory at this stage and came back to me rather easily. An hour later, the familiar, dolled-up version of myself reflected back in the mirror. The flaws were still there, but all in all, I didn't look too shabby. I felt brave enough to go out as Isabelle once again. For the day I had picked out a ribbon-tie sleeveless green maxi dress with a floral design. It was dressy enough for a shopping outing but not too formal for wearing in Singapore. 

It was the first time I dressed as Isabelle without a wig and holy hell was it such freedom! I wasn't sweating buckets in Singapore's humidity, there was no wig cap constricting my head like Sun Wu Kong's golden headband and I didn't need to worry about flyaway fringes. It was a good start even before I stepped out of the house.

The first stop was my voice therapy appointment at Alexandra Hospital. I look forward to these sessions because the voice therapist I work with is incredibly encouraging. It is also a safe space for me to practice my female voice (which is still terrible and needs a lot more practice in my opinion). As I peeked through the door of the clinic, the voice therapist stared at me quizically for 5 seconds before bursting out laughing: "Omg Isabelle I couldn't recognise you, I thought it was someone who got lost!". We started chatting, updating each other on the things that transpired over the past 5 months and did a few voice/video recordings. I'm not sure why, but she was convinced that while my pitch wasn't high, my voice worked really well with my feminine appearance and wanted to graduate me from her voice therapy sessions (Nooooooooo!). Fortunately I convinced her to give me one more voice therapy session in June.

I went on to meet friends in Somerset for sushi dinner and shopping. Being dressed as Isabelle made me put in the effort to use my female voice more, which I was able to do so for most of the night 😁 We went to the usual hits; Love Bonito, Mango, Zara, Playdress and Pomelo before grabbing bubble tea to round off the night.

Unlike the early days of my crossdressing journey that were primary filled with excitement and euphoria, there was instead a huge sense of freedom and calm this time. I didn't worry about my wig looking out of place (and therefore fake). I somehow didn't get stares despite the Friday night dinner crowds. I felt like I blended in well; just a regular gal out shopping with her friends. 

I could use such feeling of calm and happiness more regularly.

Festive seasons can be stressful events; other than the logistics and multiple visitations, there's also the need to interact with friends and relatives not seen in a while. Beyond initial pleasantries, there are questions of how one is doing with life, job, love and comments about appearances. For some this can be energising, but for me, all I want to do is to hide in a corner and potato. Nevertheless, one's got to do the expected and power through the festive period. 

This year was relatively tame for me, since I still present as my male self during the recent Christmas and Chinese New Year holidays. The biggest difference to those who have not seen me in a while would be braces and my near shoulder-length hair. After the initial big reactions of "Omg your hair!" or "WAAA!!" the follow-up question was why I wanted to grow out my hair. So far I've swatted away the question by saying "I'm trying a new look" or "I'm growing it out so I can do a man-bun, but right now it still isn't long enough". 

I'm quite self-conscious about my long hair so I usually tie it up into a semi-bun during gatherings, since letting it down might be a bit too feminine. However, the wife did tell me not to be so self-conscious about my long hair, since there are more guys keeping their hair longer these days.

Festive events in the next few years will be interesting, since my hair will be a lot longer and I will be presenting more androgynously. Or I might have gone for a surgery or two that skews my look into even more feminine territory.
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