Musings of a Singaporean Transgender

Integrating Isabelle

April 04, 20250 Comments

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...

Dressing in Public My Journey

Venturing out as Isabelle after a long hiatus

February 24, 20251 Comments

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....

My Journey

Seeing friends and relatives during festive season

February 15, 20250 Comments

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...

My Journey

2024 in Reflection

December 28, 20240 Comments

2024 has been a tumultuous year, but despite the ups and downs, I think it has been a net positive overall.Work has been largely frustrating for the first half of the year, leading me to seek out a more stressful but perhaps more rewarding role. So far it...

Mental Health My Journey Transgender

Midway Transition Hurdles

November 23, 20240 Comments

This photo captures how my transition journey feels at times. There is a road forward that many middle-aged transwomen like me have taken, but it is shrouded in misty uncertainty. I don't know how long I need to travel on the road, nor do I know whether there...

(I still sometimes wonder if I am Transgender, based on the usual metrics)

One thing I struggled with before starting HRT was whether I was truly Transgender. Even after popping those tiny blue pills twice a day for more than a year, I still wonder if I am "Trans" enough. The self-doubt is significant, and justifiably so. Transitioning is by no means a simple undertaking, with large financial, social and possibly health costs. It is literally shooting a bazooka to your old life and what is recognised as "normal". The constant and recurring critique is the brain's way of protecting oneself from the whims of the heart.

But it isn't just about the "worth it or not?", "cost-benefit-analysis" line of thinking that I tend to go into when making big decisions. The constant thoughts of whether I was "Trans" enough also stems from having lived as a guy for 3 decades with some degree of success. While I am by no means an Alpha-male, I did successfully navigate male adolescence and adulthood without too much trouble. And I feel quite comfortable existing as a regular Singaporean working adult male, Husband and Dad. So how could I possibly be transgender? Some questions that I had considered and still do include:

How can I be transgender if I don't hate my male genitalia?
How can I be transgender if I enjoyed doing "guy" stuff, and was perfectly functional as a guy, including during my army days?
How can I be transgender if I was never effeminate?
Did I just allow my fetish of women's clothes to take over the steering wheel?
Is wanting to transition a superficial whim?
Do I want to transition, or is it the rose-tinted hope that I can be successful like the very small number of transgender women influencing me to also want to transition?

Apparently, such self-doubt is common among people who transition after their 30s, as they have lived through a good part of life as a guy. Even by stretching my imagination to its limits, I still struggle to think of how I was going to unlearn all the male socialisation if I were to transition socially (aka let the whole goddamn world know I am Transgender).

I found three blog posts from the same author that resonated with me greatly. With decades of living as a guy and external reinforcement of her gender as "male", the writer described that acknowledging she was transgender felt like believing a conspiracy theory about herself. Like me, she didn't fit the popular, accepted narrative of the feminine, young transitioner who was absolutely certain of their "Trans"-ness, and that continued existence as a guy will cause significant distress. To the writer, being a guy just had a lot of feelings of dissociation rather than distress. The writer also saw it necessary to describe how she realised she was transgender (her most popular post. Read it!) and write a guide to help people figure out if they transgender, which I found incredibly useful.

I've come to terms that I am transgender, although I think the self-doubts will remain until the cat is fully out of the bag. A friend shared that as I come out to people and transition socially, I will gradually figure out which parts of myself are armour that I had put on over the years and which are core. And Isabelle will slowly develop over time.

Right now however, I don't even know which parts are armour that my male self had learned to be so comfortable wearing and which parts are core. Every part of me feels core! It even feels like when I fully transition, I'd still be 99% my male self, that I'd just be pretending to be Isabelle and co-opting feminine mannerisms not because that was truly me, but because it matched my new exterior and society would be more inclined to accept me if I behaved that certain way (Jokes on me, society will always brand me as transgender, with all the associated negative labels). All this however, is conjecture based in worries for what the future holds. Only time will tell how Isabelle will be like when she has been fully let out into the world.

Gender Dysphoria Mental Health Transgender

Dr Z PhD's Channel - A great (and free!) resource

September 19, 20241 Comments

I've been posting predominantly about my transition journey so far, which makes me feel like I've neglected the crossdressing community quite a bit for the past year. So I'd like to share a great resource I recently discovered that I think will be very useful for anyone with...

Mental Health Transgender

My mental state isn't great these days

August 11, 20240 Comments

I wrote about how my mental state hasn't been the best 9 months into transition (around February this year), and keeping it healthy was a constant struggle. Well it seems that things haven't really improved. My mental health has been in the pits. Here's one of many similar journal...

HRT Social media Transgender

Estrogen is NOT a magic pill

June 10, 20240 Comments

(This post is probably going to get me cancelled 😕)Captions of "Estrogen is magic!", "Estrogen is pixie dust!" "Estrogen is crack!", followed by a side by side pre-transition photo of a man with facial hair and a post-transition photo of a long haired woman with makeup are so...

HRT My Journey Transgender

My HRT Transition Journey (Year 1)

May 05, 20240 Comments

I read that it is important to keep a journal to log down emotions, thoughts, bodily changes and other details throughout HRT, so I've started this post to record them all down. It is on the longer side with bits that might not flow as smoothly, since they...

Blending In Dressing in Public Gender Dysphoria Transgender

Passability brainworms

April 23, 20240 Comments

(Some days, it just feels like we have Dune-sized brainworms)Brainworms. I only recently learned about this term. While urban dictionary defines it as "cognitively degenerating" or "going off the deep-end", the way it is used by younger generation transgender folks seems to be to have an illogical, unjustified...

Transgender

Guard yourself against self-doubt

March 27, 20240 Comments

(I love comics from @theAwkwardYeti, so if you haven't heard of him, do check his blog out)The trigger for this post was something that happened when I went for my hair transplant in Bangkok. I'll just paste the note I wrote when I was feeling incredibly emotional. ...

Musings of a Singaporean Transgender

Integrating Isabelle

Venturing out as Isabelle after a long hiatus

Seeing friends and relatives during festive season

2024 in Reflection

Midway Transition Hurdles

Dr Z PhD's Channel - A great (and free!) resource

My mental state isn't great these days

Estrogen is NOT a magic pill

My HRT Transition Journey (Year 1)

Passability brainworms

Guard yourself against self-doubt

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