Musings of a Singaporean Transgender

It's amazing that I've already been on HRT for 2 years now. The egg crack, first coming out to my wife, feeling the initial bodily changes due to HRT, feels like a fevered dream. And what a rollercoaster ride it has been the past years. I don't think my life has ever been this tumultuous. 

Bodily changes wise, it feels like everything has stalled after the first year. While my hips and bum do feel fuller, I've had fat redistributed to my lower waist that seems to cancel each other out with regards to getting more feminine proportions. Boobs have been the same size since the 1 year mark (friends and I jokingly call them our xlb 小笼包 boobs), while other more visible changes aren't HRT related; specifically the reduced facial hair due to electrolysis and longer hair on the top of my head, which is taking painstakingly long.

Emotionally, there has been so many ups and downs, it's amazing how I even functioned the past 2 years. It's been no secret that my mental state has been terrible since the 9 month mark of transition, battling fears of falling short of my transition goals, envying feminine transwomen in the community that seemed to cross the threshold so effortlessly, worrying about rejection and hating my reflection that I see in the mirror on a near daily basis. The midway transition phase is known to be the most challenging, when you're neither here nor there, but all that can be done is be patient and wait.

My relationship with the wife has also seen many ups and downs. While she is supportive, my increasingly feminine appearance brought out all manner of fears in her and triggered feelings of grief; the loss of the man she married, being replaced by a familiar person, but yet total stranger named Isabelle. Transition isn't easy for the one transitioning, but it isn't a cake walk for partners either.

Nevertheless, there were many things to be thankful for in the past two years. I made new close friends that I feel could potentially be lifelong friendships. I came out to my sister, a close friend and most recently, my parents (a separate blog post needed for that). I started to see the woman in the mirror as my hair grew out, making me hopeful for the future. A few funny moments when guys second guessed their entry into the toilet was validation that I looked female, even though I was wearing uncle berms. And most importantly, having a partner willing to work through the challenging issues together.

The 3rd year is going to be more exciting as I come out to more people. It is scary, but I look forward to it.

So far I reference Isabelle almost entirely in the third person. "Isabelle", "She", "Her". I've also become so adept at compartmentalising that Isabelle's become somewhat of a narrowly defined character. A well dressed, glammed up woman that makes an occasional appearance to paint the town red. 

But I've been finding this very unhelpful in my journey to integrate Isabelle into daily life. And most importantly, Isabelle isn't a separate persona, nor is she just one part of me. I am Isabelle. In entirety, comprising of all facets of myself. The glamorous, dolled-up version, the bare-faced sloppy version, the bespectacled work version, etc. Even moments when I feel masculine or need to play stereotypically masculine roles (e.g. as a dad), these are all parts of Isabelle. I've come to realise that transitioning isn't about becoming Isabelle. It is about accepting that I am Isabelle.

Of course, the reality is that physical changes are important in helping me to see myself as a woman. So a year ago when the reflection in the mirror was very much a short-haired guy, it wasn't possible for me to see myself as a woman. And I've been so used to doing this huge switch from frumpy guy to dolled-up woman, that it has been a challenge to see myself as Isabelle without makeup. But as I reach my 2 year hrt anniversary and my hair is a lot longer, the internal barrier to seeing my daily self as a woman has been lowered. There is a need to shift how I view myself.

There's also internalised shame associated with being transgender that is a barrier to integrating Isabelle into my daily life. It still feels weird to tell others the words "I am Isabelle". Heck, I only told my wife recently (Mar 2025) that the name I chose for myself. That's a really long time, considering that I came out to my wife in 2018 and that I have gender dysphoria. So far, it has been much easier to refer to the female self in the 3rd person. But that might have also led to the wife viewing Isabelle as this person that looks somewhat like me but is a stranger, with demands that she be let out, demands that she be seen and acknowledged. Which is very unhelpful in getting my wife to be comfortable with me as Isabelle. But as a friend rightly pointed out to me: "Isabelle...even you're not comfortable with Isabelle". Being secure in my own identity is the first step in integration.

It isn't easy, especially having lived so many years as a guy and building an entire identity as one. But I try to celebrate the small wins on this transition journey and acknowledge that I am a constant work in progress. Slowly but surely, I will come to see that I am a woman. I am a transwoman. I am Isabelle.

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. 

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.