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Musings of a Singaporean Transgender


When I came out to my friends, most of them were very shocked as there were zero signs that I was transgender. Probably not a good badge of honor, since it just meant I was too good at suppressing and hiding this part of me to the point where it was unhealthy. I'm quite certain the constant hiding and fear of being discovered shaped the way I lived, my personality, as well as taking a toll on me mentally. But that's a story for another post.

I never knew I was transgender until my egg cracked when I turned 35. While I didn't show/feel the common signs that a person was transgender back then (e.g. hate my body), looking back over the years, it was GLARINGLY obvious that I was transgender when I looked at the hints:
  • Envied the girls during racial harmony day for being able to wear a qipao
  • Always selected a female character when playing video games
  • Wishing/praying during birthdays and to God that I would wake up a girl
  • Wanting to fill my 6 choices of secondary school with all girls school, so that the administration had no choice but to send me to one of them
  • Regularly wanting to wear women's clothes
  • Feeling incredible fear that my desire to wear women's clothes would be discovered
  • Imagined I was put into a chrysalis like Sarah Kerrigan from Starcraft, except I came out female and beautiful
  • Wishing I was Jaceyln Tay in the local drama Legend of the 8 immortals
  • Being super smitted by a newspaper cutting of Catherine Zeta Jones from Zorro and wishing I looked like her
  • Wishing I could grow out and dye my hair, but didn't because I would be questioned by parents and friends
  • Wondering how it would feel to have female body parts
  • Wishing I had female body parts
  • Always identified with the woman when I watched adult films
  • Not feeling like I could click with the boisterous and sporty boys
  • Not identifying with masculine heroes for guys like football players
  • Being very curious about transwomen performers during a Thailand holiday but pretending to be super uninterested
  • Wishing I could be a bride because the dress was so damn pretty
  • Staring at brides (when I attended weddings), imprinting in memory how pretty the gown is so that I could imagine myself in it after the event
  • If I had superpowers, to be able to stop time so that I could go into shops to try on women's clothing safely
  • Feeling free and happy when I wore women's clothes
  • Feeling confident and powerful when I finally saw a well dressed female version of myself in the mirror
Ok some of the points in there is showing my age 😅 But the list is so damn long, it was amazing I didn't realise I was transgender until later in life. It was probably because I learned very early in life that boys are not supposed to like girls' things and it was shameful to want it. And saying it out would lead to derision, disgust, being ostracised and bullied. So it became a secret I guarded obsessively, a secret to be taken to the grave. To be fair to myself, there were barely any resources back then. I did try to find books in the library related to transgender and crossdressing, but found nothing. The early internet had some info on transwomen (transsexuals as they were called then), but it seemed so far fetched and impossible that I didn't even consider it a possibility ("I didn't hate my body, how could I be transgender?"). 

There is a tinge of envy when I look at younger transwomen who grew up with the large amount of information on the internet that sped up their discovery of themselves. Perhaps my egg would have cracked way earlier and I would have transitioned before puberty, without testosterone shaping my body into what it is now. But such thoughts are unhelpful and poisons the mind. Wishing for the impossible is an exercise in futility. There are many things in my life to be grateful for, even in my seemingly tumultuous journey. Like my kid, one of the greatest joys in my life, who would not be around had I transitioned earlier.

 

(Spilling the beans, after so many years)

I finally came out to my parents on 18 April 2025, Good Friday. No special significance other than wanting to give them more time to digest the news over the long weekend, although I had been joking with my friends that maybe my Mum would be extra understanding during the holy days where Jesus died for our sins.

Coming out to my parents was a key step in my transition journey, because I felt they had to know before I started telling more people about myself. The last thing I wanted was for them to hear from another source that their son is Transgender. Being a person who likes to be in control instead of leaving things to fate, telling them first was my way of de-risking a potentially incendiary situation. I had been wanting to tell them since February, but due to house moving, a super hectic Chinese New Year, followed by a family holiday in Japan, the wife was very uncomfortable with the timing. In addition, she felt that I didn't have a confident answer regarding how we will deal with our kid, which was something that my parents were bound to ask about. As a result, I postponed coming out, but it weighed increasingly heavily on my chest. After multiple rounds of back and forth, we finally came up with a detailed FAQ on how to address the tougher questions. 

I had many fears about how they would react to me being Transgender. My Mum was a staunchly devout Catholic, so there was a chance of rejecting me and what I was doing to my body (i.e. taking hormones, thinking of surgery). As for my Dad, while he had a more YOLO, pursue what you want in live mentality, he is an Asian Dad and I was the eldest (and only) son in the family. How they would react was a dice roll. 

I had been rehearsing coming out to my parents during the drive to work, arranging my points for cohesiveness, making sure they made sense, readjusting the points when it seemed a bit odd. It wasn't easy but I felt ready.
 
I went to my parents' place for dinner and had some random chit chat with them to try and relax. But I could feel the lump in my throat each time I tried to say that there was something important I needed to tell them. I could feel the fear building and nearly backed out, but it didn't feel right. I knew I would be kicking myself if I didn't see it through today. So I asked my parents if we could adjourn to their bedroom as I had something to tell them. Because I have never requested for a conversation in that manner, it was obvious my parents knew something was up. I could taste the anxiety in the air, especially from my Dad. I knew I couldn't drag it out or the anticipation would just build.
 
So I sat them both down and started.
 
I said that what I was about to tell them is very shocking, so I hoped that they would remain calm and allow me to finish explaining before asking questions. That regardless of how they react, I would love them. I told them that I am Transgender, that I have had feelings of wanting to be a girl since I was 5 years old and gave examples. I told them that I am on HRT and was seeing a psychiatrist in NUH, who had diagnosed me with gender dysphoria. I stressed that I was born this way and it wasn't due to upbringing, nor was it their fault. I reassured them that I will not wear a dress in front of my kid until she is a teenager and understood things better (this however, is something that I don't agree with, but to quell potential anxieties, that was the stance I took). To make things easier, I wouldn't wear a dress at family gatherings too.
 
Despite multiple rounds of practice, the words that came out of me felt like a gibberish mess in comparison, slow and stuttered with me constantly looking away, only stealing the occasional glance at their faces. I could see that my parents were trying their best to stay calm and understand the situation. They asked if there were medicines that I could take to managed this "condition", to which I explained that there was no such medicine. The solution to gender dysphoria in my case was to start HRT and transition to live as a woman. 

My parents' concerns were primarily about bringing my kid up well and my wife's views on me transitioning. My Mum said she would pray for me, while my Dad (who has a more enlightened view to life) said that the most important thing is that I live my life and pursue happiness, but don't do stupid things like off myself, especially since I have a responsibility to raise my kid. Everyone else's viewpoints don't matter.
 
At the end of our chat, my parents reiterated that they will support and love me. It's about as good a reaction as one could expect, although it was clear my parents didn't fully understood what it all meant. But I guess when you've never seen your eldest son in such pain, crying a bit and trying to share heavy stuff, they probably held back their reactions.

Coming out to my parents was terrifying and cathartic at the same time. The huge weight I had been feeling was lifted and I could breathe a bit lighter. They now had answers to why I was growing out my hair and I could come properly spill the beans to more people. Since coming out to my parents, I have told three more close friends, who were all incredibly shocked by ultimately supportive. I feel seen as a complete person, with more people knowing about Isabelle. The imagined scene of my own wake that used to bring me to tears consistently no longer had the same power it does.

I separately approached my parents 2 months after coming out to ask them about insights they have had since I told them I was Transgender. My Mum told me she wants her son and that she will pray to God to help me overcome my mental struggles, to which I responded that I could not give her what she wants. My Dad still maintained his YOLO stance about life, but reiterated the responsibility I had to my wife and child. Hilariously, he also said to ignore what my Mum wants, since it is ultimately my life. It is still early days and my parents will be tested further as I gradually present more female. But it is my life and I am feeling hopeful. 

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. 

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.


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 seems promising, so fingers crossed there.

Relationship with my Wife came so very close to the precipice. Fortunately the foundation we built over the years helped to hold it all together. It took a while and many, many tears, but we managed to become more honest with each other and ourselves. While still a work in progress, we are now able to communicate at a level that we have never been able to do before. Home is stable and I am extremely thankful for that.

My mental state has been generally terrible this year, as described in earlier posts. Dissociating happens a lot in order for me to continue functioning. But through the emotional roller coaster ride, the pensive thoughts, I've become a bit more in touch with my emotions. I'm learning how to reach through the layers of bubble wrap to connect with feelings other than rage, impatience and envy. I've broadened my emotional vocabulary that allows me to better describe why I feel a certain way. I'm still working on being less self-critical and learning to love myself despite my flaws.

I still don't see Isabelle in the mirror and get "sir-ed" consistently by random people I meet (which sucks). Granted, my polo-tee and berms look definitely screams "Singaporean Uncle", but it would be nice to see the occasional confused look in people's eyes. Currently I still feel like an imposter and not confident enough to present female without makeup.

My new home is finally taking shape. Renovation delays despite my best efforts meant that I cannot move in by the end of the year, but I'm almost near the finish line. Which means a larger safe space for me to express myself a bit more.

2024 was a hectic year. 2025 is already promising to start off blazing with action. But I am holding to hope. With some time and luck, Isabelle might regain confidence to finally show herself more regularly.

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 will be obstacles or unexpected forks in the road. It feels like a long, lonely journey, but I know that the only way is forward. Left foot, right foot. Keep moving forward. 

I've been on HRT for 1.5 years now and if you've been following my other posts, mental health has been a struggle since February this year (10 month mark onwards). A lot of it stems from anxieties of the future, fear of acceptance by people closest to me and worries that I will not be able to hit the goals that I set for myself despite my best efforts. Seeing a rather guy looking person in the mirror and bodily changes such as hair removal and fat distribution happen at a glacial pace doesn't help either.

I'm in a midway transition phase right now, which is the hardest part of transition. A recent video from Dr Zhikhareva highlighted why the midway transition phase is so damn hard, even more so that the initial decision to begin transitioning. It was a video that resonated with me, but also served as a reminder that better days are to come. I just need to be patient about it and kinder to myself. 


Usually when we see photos of transgender individuals online, they're usually happily transitioned and living as their authentic self. A pre-transition photo is also usually shown as comparison to contrast how far they have come. The journey of these transwomen and transmen are something to be celebrated for sure, because it was definitely not an easy one. However, you will be hard pressed to find photos of the midway transition phase. Understandably so, because who wants to show the part of their journey where they feel ugly, incomplete and vulnerable?

It is this middle phase where there is significant uncertainty in what is to come in the days ahead. It is a period where misgendering often happens, because appearance wise we are somewhat in between the binaries. Family, friends and colleagues are also just coming to terms with news that you are transgender. Internally, there is also significant impatience in reaching the end goal of "passing" and living as our intended gender. The difficulties of the midway transition phase can be exacerbated by the lack of financial / social / emotional support. Imagine feeling like you need facial surgery in order to reduce certain masculine features and misgendering, but do not have the financial resources to do everything. 

Transitioning is usually likened to the important chrysalis phase, where the fuzzy caterpillar transforms into a beautiful butterfly. Time is needed for the body to change, for the wings to form and harden. It cannot be rushed, otherwise the metamorphosis is incomplete and what emerges is a butterfly that is unable to take flight. Many a cautionary tale has been shared where some transwomen rush through the physical aspects of transition (facial feminization, SRS, body sculpting, breast augmentation), but are still deeply unhappy because the integration and self-acceptance has not been done. However, the chrysalis is a vulnerable phase that sometimes feel like it is in the way of getting to the end state of becoming a butterfly. Also, nobody wants to be a freaking Metapod.

(Like seriously, how do I win battles in life if Harden is the only move I know)

Just to end off the post, I have been making multiple efforts to better my mental health. While I still complain to my friends regularly and go into my moody periods, I try to keep afloat and positive. I've been seeing a psychologist to help unpack some of the feelings that I've shoved aside for decades. I'm also learning to be kinder and less self-critical; a trait common in many Singaporeans. Recognising that I am doing my best during this tough period is already a step in the right direction. I'm also trying to change the way I think to help integrate into my current self the hidden parts of Isabelle (e.g. her vivaciousness, friendliness, curiousness), so that when I eventually emerge from this vulnerable phase, I'll be a lot more comfortable with my identity. 
(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.

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 were written at different months of my transition.

<Note: Any commentary here is entirely empirical and based on my personal observation (i.e. experiment of ONE). So nothing here is medical advice, nor a reflection of what you will experience if you plan to be on HRT. As they say, "Your Mileage May Vary (YMMV)", so tamper your expectations and please do your research.>


Day 1
(4 May 2023)
Spiro - 100mg/day, Estrofem - 4mg/day
Weight - 55.5kg

Unintended, but my first day on the journey to womanhood happens to be the unofficial Star Wars Day. I just started, so there aren't any expected changes, other than a mixed bag of emotions that I've felt for a while now; a great sense of hope for the future but also significant trepidation of the challenges to come, now that I've set myself down the path of transitioning. If anything, popping the anti-androgen and estrogen pills for the first time felt extremely anti-climatic, as though my fear of HRT's risks were irrational and unfounded. But the best (and worst) is yet to come. So let's see how this goes. 

May the Force (4th) be with me. 


Day 7
No change to dosage and body.

It's still early days so there are no visible physical changes. Some transwomen report experiencing a greater sense of calm, while others felt they were more in touch with their emotions and less numb. Well...I felt neither 😅 I did feel more light headed in the initial days and my baseline heartrate seems to have gone up. Hope that is just a temporary phenomenon. I also felt a bit more tired, but it could have been due to the general lack of sleep.

Libido took a near immediate hit within a few days of popping the pills. Little fella down below seems to be less inclined to stand. A bit of a downer because I'm not too bothered by my male appendage. My desire to dress as a woman also went down a lot (linked to libido it seems) and I also found myself uninterested in posting photos on Instagram. 


Month 1
(June 2023)
Spiro - 100mg/day, Estrofem - 4mg/day
Weight - 55.5kg

Around the 2nd week my nipples started to feel a bit tender, with a feeling of soreness when they are pressed directly. By the 3rd week, it felt like there was a small, hard marble behind each nipple, and they were perkier than before. The other observation was an increased sensitivity in my nipples. I've had zero sensitivity previously, but now when I gently rub them it seems to stir something down below? Interesting sensation and definitely welcome. 

Emotionally I've still not felt much ups and downs that some may have reported when on estrogen. My brain did occasionally catastrophise my decision to transition, such as worrying that I will never be convincing and passable, that HRT changes will be minimal and I will end up looking like a guy with teenage girl's boobs. But I successfully shoved these thoughts under the carpet by ignoring them. After all, it is still early days and nothing is irreversible. I guess years of compartmentalising has it's benefits 😅

As the changes due to HRT are very gradual and will take around 2 years to be more visible, the journey to womanhood feels like a really long one. For those who are dying to have their bodies become womanly and live as one ASAP, it's best to tamper those expectations significantly. I did a comparison with photos I took on Day 0 and there were no differences except for slightly perkier nipples.


Month 2
(July 2023)
Spiro - 100mg/day, Estrofem - 4mg/day
Weight - 57kg

Some fat has been building behind the nipple, causing them to push out a bit more prominently. While I am nowhere at risk of being outed, they are a reminder that in X months time, it is going to be quite hard to hide them. Nipples are also permanently sensitive and sore, which is ok until I bump them into something by accident and it's ouchie. 

I noticed that I was putting on a bit of weight since my baseline appears to have shifted from around 55.5kg to around 57kg. As there hasn't been any changes to my exercise, diet or lifestyle, HRT is definitely the cause. If I want to keep my figure I had better watch my diet more closely.

It also appears that muscle strength has dropped quite significantly. I casually went up to a chin-up bar and to my surprise I could only do 7; which was a big drop from my usual 11 (without any gym training). I also struggled to do more than 30 sit-ups, when just a few months back I could very easily do a burst of 40 sit-up. While I was aware reduced strength was an effect of being on HRT, I was quite shocked at how quickly loss of strength took place.


Month 3
(Aug 2023)
Spiro - 100mg/day, Estrofem - 4mg/day
Weight - 57kg

I had an annoying headache that lasted for 4 days and refused to go away. While a continued lack of sleep was likely a contributing factor, the doctor also said that it was likely due to higher or fluctuating oestrogen levels in the body. Fortunately it went away after a good long rest over the weekend, but it is something to monitor. The recent CNA documentary about increasing kidney failure rates scared me into reading about HRT more seriously, since popping pills apparently places a high load on the kidney as well. 
<Correction: Popping pills increases load on the Liver, not the Kidneys>

My weight has also been slowly creeping up. For the first time in a long while, I hit the 58kg mark, and my work pants occasionally feels too tight at the waist. Although estrogen HRT weight gain is widely reported (due to drop muscle mass and corresponding calorie burn), it is a bit disturbing. I've been cutting my rice intake, but more needs to be done to match the new baseline calorie burn.

I touched the back of my hand, which felt softer and less oily than I remembered, which was nice. I wonder if my skin would soften a bit further as the days progress. Sadly, I still have rather large pores and acne scars on my face, so the flawless skin that I see in so many other transwomen are likely a pipedream, even if I blow cash on laser and subcision treatments. 


Month 4
(Sep 2023)
Spiro - 100mg/day, Estrofem - 4mg/day
Weight - 57.5kg

I've been feeling sleepier than usual, which isn't helped by regular overtime and late nights. Fighting off the post-lunch sleep monster to concentrate on work was quite a challenge and I found myself consuming more cups of coffee than usual. It seems like a lack of the "get shit done" hormone has been putting my energy levels on a roller coaster. Hopefully this goes away at some point in the future. 

It might be my mind playing tricks on me, but there are some baby hairs sprouting in my bald spots. It still looks bare in photographs (which is a bummer), but it does give a bit of hope that the combination of finesteride, anti-androgens and estrogen is bringing some of my hair back. 

There were moments where reading a funny remark made me chuckle involuntarily. It was subtle, but a marked difference from how I would have reacted...which was no reaction other than registering: "This is funny". I don't recall ever having this involuntary reaction. When I shared it with other transwomen, they told me they had the same experience. One described emotions on HRT as accelerating faster and hitting a higher top speed. Sounds about right. I also noticed that I was less patient and more vocal about issues in the work place, although that could partially be attributed to stress. 


Month 5
(Oct 2023)
Spiro - 100mg/day, Estrofem - 4mg/day
Weight - 57.0kg

Recently I've been having more occasions where I feel more tired and down than usual. I'm not sure if it is due to regular lack of sleep or just the whole hormone imbalance causing lethargy. The "xian-ness" isn't due to one single factor; it is partly work related, but i can't say brainworms aren't getting the better of me. I've been fighting off thoughts that I'm gonna fall short of the expected goals of transition and I've already been managing my lowered expectations consistently (not setting an impossible goal of looking like a Kpop star, like some young transwomen do). Yet I feels like i'm gonna be a failure to myself and everyone around me.

Objectively, nothing much has changed, nor will it in the next few months. People from outside might see that I've got my shit together, doing alright at my job and life. But the brainworms remain. I saw an attractive middle aged cis-woman at Tiong Bahru plaza on 2 September in a long white dress whose whole look was exactly what I strived to be. But my brain immediately told me that as much as I hope, I will never come close to being like her.

I finally went for my first endocrinologist appointment at NUH on 19 September, after 4 months of waiting. If I had not sourced for my pills via the private route, this would have been day 1. The doctor I saw was an experienced looking man with a head of white hair. Entering into the room, he asked in a serious tone a bunch of background questions; when did my gender dysphoria begin, NS PES status and vocation, my age, whether I was married with kids, etc. He then proceeded to caution about transitioning in Singapore, that while there are some successful cases, he did encounter unsuccessful cases, including a transwoman 1 year older than me who had SRS, but was asking to detransition because the wife and children could not accept her transition. But then he called himself a hormone peddler, saying that with the psychiatrist's diagnosis, he will give me the anti-androgens and estrogen, as long as I am aware of the risks. After some discussion about the different types of pills available, he gave a presciption for Cyproterone and Estradiol Valerate (Progynova).

The endocrinologist ended off the session again with the warning that transitioning for middle aged adults in Singapore isn't easy, and that I will have to deal with all the social issues faced by transgender persons.


Month 6
(Nov 2023)
Cypro - 25mg/day, Progynova - 4mg/day
Weight - 57.0kg

It's been half a year since I have been on female hormones. Popping pills in the morning and evenings have become quite routine, though it makes me feel like a 60 year old man eating his high blood pressure medicine. I've switched to Cyproterone and Progynova in early Oct. Some of the experienced transwomen I met suggested that I reduce the Cyproterone dosage I was prescribed (25mg per day), since long term use increases the risk of meningioma, which is a brain tumour (Sigh). Generally, anti-androgens used for suppressing testosterone aren't great if taken in the long term, so I plan to cut my dosages further and monitor.

Emotionally, I don't think the switch in medicines resulted in much changes, so I guess it is ok? My energy levels feel a bit less nuked, which was something I felt regularly when I was on Spironolactone.  

In terms of physical changes, other than regrowth of hair on my head, I noticed that my waist has gotten a tad bit thicker (especially the lower tummy), but a bit of fat has also distributed to my butt and hips. Let's hope the latter continues. My brain might be playing tricks on me again, but I think my cheek apples also do look a bit more pronounced due to the subtle fat distribution.  

My areolas have darkened in colour, as well as expanded from 2cm pre-HRT to around 3.5cm at the six month mark. Chest development wise, my left boob seems to be developing a bit more than the right. They're both conical in shape now, which causes the nipples to poke out of my shirt a bit and makes me look like I'm having mild gynecomastia. No one has commented on them yet, so I guess I don't need to start wearing chest-binders to hide them. Because I live with my parents and wear T-shirts while at home, I do consciously pull the collar of my T-shirts forward so that the extra material helps to hide my developing chest.


Month 7
(Dec 2023)
Cypro - 12.5mg (3 times per week), Progynova - 4mg/day
Weight - 56.5kg

Since I switched to Progynova (estradiol valerate), it feels like my bodily changes have stalled. Boobs appear to be slightly smaller when comparing the 7th and 6th month photographs. My nipples also no longer feel sore (which I take to be a sign of development), which was the case when I was on Estrofem (estradiol hemihydrate). It could be a nocebo effect, after I found out that the bio-available estrogen was lesser for the same dose of estradiol valerate as compared with estradiol hemihydrate. Nevertheless, I think I will at least continue this dosage until the next blood test, to get a sense of what my levels are. 

One of the best things so far is how soft and smooth my skin feels. I actually like running my hands over my forearms to feel this newfound softness. I also no longer have bad acne, which is amazing. God, why didn't I start HRT earlier. Years of cystic acne and scarring from these massive "volcano eruptions" would not have happened. 

While there hasn't been many visible changes, my emotions this month have been more in-flux. While nothing too dramatic, I've gotten frustrated over situations/people easily, and I also had a few depressive episodes. It could have been due to situation in general though. 


Month 8
(Jan 2024)
Cypro - 12.5mg (3 times per week), Progynova - 4mg/day
Weight - 56kg

I went for a blood test in early December at NUH. Results wise, it seemed like my Estradiol (E2) levels were quite low despite maintaining the same 4mg dose of estrogen pills. The main change was my switch from Estrofem to Progynova back in October. As blood tests aren't frequent there was no confirmation that this was the cause, but instead of increasing my dose further to 6mg of Progynova, I asked the endocrinologist to put me back on 4mg Estrofem instead which he gladly agreed (since taking a lower dose is generally preferred in the eyes of healthcare professionals).

The other issue was that my progestin levels were really high. I was concerned about this, because persistently high levels could potentially lead to brain tumours in the long term. Strangely, the endocrinologist said it wasn't a big concern, but to be safe, I decided to cut my weekly dose further from 3 x 12.5mg per week to 2 x 12.5mg per week. Hopefully this will help to bring down levels during the next blood test. 

Bodily changes wise, there did not seem to be significant changes. Might just be in my head, but there may have be further growth in the chest department, albeit very gradual. Wearing T-shirts with the soft cotton material (e.g. Army admin tees) are starting to look a teeny bit suspicious.


Month 9
(Feb 2024)
Cypro - 12.5mg (2 times per week), Estrofem - 4mg/day
Weight - 58kg

HRT is making me fat. I can feel a fair bit of fat build up at my lower belly, that if I don't suck in my tummy when looking in the mirror, looks like a paunch. My work pants feel tighter in a bad way and I find myself regularly loosening my belt by a notch after lunch. While my weight is still healthy, it is creeping up even though I didn't increase my food intake. I don't really want to bust the 60kg mark. Sadly, the fats aren't going to my chest area as much. There doesn't seem to be major observable chest growth, and I still guy mode without comments at work or at home.

The further loss of strength and muscle mass is also obvious. Recently I tried to do pull-ups and could only manage 4, down from 7 in the third month and 11 pre-HRT. Muscles does increase metabolism, so lesser muscles meant that my metabolism did go down too. 

Emotionally, I find myself easily irritated during the 1 - 4 hour window after taking estrogen, where I feel a grey cloud over my head and become extra snappy about things. This is worsened if I'm tired and in need of sleep.


Month 10
(Mar 2024)
Cypro - 12.5mg (2 times per week), Estrofem - 4mg/day
Weight - 58.5kg

It appears that fat distribution due to HRT is starting to give me wider hips. The changes can barely be seen in the mirror, but when I look at the pre-HRT photos, 6 month and 10 month photos, the effects are shockingly obvious. While my body doesn't have the hourglass shape, it's still pretty amazing how hormones can change the body shape. My hair is still quite short so I still pass as a guy without any effort (because I still look like one).  

A comment from my Dad recently took me by surprise. Over breakfast, he suddenly said that my face shape has changed. I acted cool and asked him what he meant. He said that my face looked sharper, probably due to my braces. Whew. While some of it could be due to braces, pretty sure some of it was due to HRT. 

On 18 March, I had a very bad episode of emotional deregulation. While it was triggered by certain conversations, the root cause was being really frustrated that the changes from HRT were taking so damn long. Some transwomen were already looking and presenting female at their 1 year mark, but for me, I still look like a guy. Being able to present female was nowhere in sight. I joke around that being in uncle mode works to my advantage as I do need a bit longer to ease into social transition, but honestly, it kind of sucks. It feels like transitioning is taking forever, and I will never reach my transition goals.


Month 11
(Apr 2024)
Cypro - 12.5mg (2 times per week), Estrofem - 4mg/day
Weight - 57.5kg

While my breast development isn't significant, there are some shirts I can no longer wear (e.g. Army admin tee, slim-fit work shirts). I had to buy new clothes with thicker material and a looser fit at the sides so that I could better hide my chest at work and on weekends when I am out with relatives/friends.

Mentally I feel a bit more stable this month. A chat with friends helped me through a bad bout of dark clouds that had lingered regularly over my head over the past weeks. Though I still mostly see an uncle in the mirror, occasionally I do see hints of the woman peeking through in my reflection. Right now I'm just waiting for my hair to grow out a bit more, which will help in my presentation.

Switching back to Estrofem seemed to also have helped my estrogen levels, as shown by the recent blood test. The increased rate of random hair drops I experienced after I switched to Progynova and Cyproterone for 3 months also seems to have stopped. I'm pretty glad Progynova and lower estrogen levels was the cause, because I really didn't want to go back to Spironolactone as my anti-androgens due to the tiredness that it causes me.


Month 12
(May 2024)
Cypro - 12.5mg (2 times per week), Estrofem - 4mg/day
Weight - 57.5kg

Amazing that I have already been diligently popping AA and Estrogen pills for one whole year now. While my transition journey has been much slower than I had initially hoped, the bodily changes are coming in; I just need to be patient. My bum feels fuller, hips wider than when I started transitioning. My left boob is about the size of a small orange, so with some luck, by end of year two I might just be able to squeeze out a bit of a cleavage with some push-up bras. The right boob does has catching up to do however. Nevertheless, seeing and feeling the changes does give me a great sense of comfort.

It's been a long post, so if you reached the end, whew! Thanks for reading all the way. I'll continue to log my 2nd year of changes. Hopefully at the end of it, Isabelle would have emerged both physically and socially.

Since my last post, quite a number of people have reached out to me to ask about things. Messages were mainly from people in the crossdressing community that I had known for some time. There were encouraging messages cheering me on and wishing me the best in my transition. Some who had transitioned told me that the thought process and fears I had laid out pertaining to work and family all resonated with them significantly. There was shock from some who could not understand my rationale for transitioning, since being a crossdresser was much easier and I had the best of both worlds. And a few started to feel their own egg shells crack. 

While I've got quite a number of blog posts incoming, I thought it is more timely to provide an update of how I am doing, 10 months into my transition.

Generally, I am ok. Balance at home with the wife is still preserved (for now), and I cannot overstate the importance of having harmony and a safe space at home. It is a privilege that most married transitioners do not have the luxury of enjoying and I do not take it for granted. With so many things in flux, I am extremely glad this area of life remains stable. 

I still look like a guy, so living as my guy self at home and in the office is a cakewalk. There hasn't been any weird questions or comments about my appearance, which is in a sense a blessing since my hair is taking forever to grow since my hair transplant in Nov 2023. The downside of that is that I feel like I'm on the same goddamn spot 10 months after HRT and that I will never reach my transition goals.

If I'm honest, I don't think my mental state and mood has ever been worse. Gender dysphoria and worries of the future is a near daily battle in my head that I constantly need to soothe. I have a tendency to catastrophise, and on bad weeks it happens every 2 days, leading me along in a doom spiral of envying the things others have that I currently do not, and the very many bad things that will come my way. My energy for the day is sapped and all I want to do is lie down and sleep for a really, really long time. I am thankful for friends in the community I can rant to, since it is very hard to share such fears with non-transgender folk without sounding inane and superficial. But sometimes it is the same friends who are further along on their own journey that are the intense source of envy and dysphoria. A casual comment could send my emotions on a downwards spiral. 

But life has to go on, bills and taxes need to be paid, work needs to be done and the kid need to be taken care of. So I trudge along, putting my best face forward, checking off the never-ending to do list while popping my HRT pills religiously and going for various treatments to inch me along in the direction I desire. I tell myself that weakness does not get me anywhere, only action does. 

If you met me in person today, you would only see a perfectly functional, middle-aged Singaporean man...which I am. But I'm barely holding it together on some days. Would be nice to win the next TOTO jackpot. I think that will help to alleviate a good number of recurring fears that I have. 

I'm Transgender.

I finally admitted this to myself out loud. And it is absolutely, fucking terrifying, like nothing I have ever known. The fear emanates from the pit of my stomach constantly, threatening to burst open from my ribcage like a chestburster from the Alien movies. Except there is no dramatic bursting from the chest and the fear continues. I still remember Em-Chan's profile stating how she was also "f***ing scared" when she realised she was Transgender in 2019. Never in my mind did it strike me that my turn would come. 

Perhaps some of the readers here saw it from a mile away. Some may say, "See, I knew she was going to transition". For the latter, please keep your opinions to yourself. Insisting that someone is an "egg" when a person is still questioning and struggling with gender identity is forcing a person into a mould and extremely unhelpful. Remember, breaking eggs from the outside harms the cute little birdy inside. The little birdy needs to break out of its egg by itself. 

I suppose I always knew deep down that I wanted to be female, but never allowed myself to consider that living as one was an option. I never let myself think of the possibility of undergoing hormone replacement therapy (HRT) and transitioning to become a woman eventually, because it was too damn hard and I was sort of ok with my male life? But a seed of a thought became the embers that started this blazing inferno; "Since I don't want more children and fertility isn't a must for me anymore, what happens if I took some hormones to make myself more feminine?". And this random musing led me to dig deep on my main reasons for crossdressing and down the rabbit hole. Googling the effects of taking estrogen as part of HRT also made me feel like...maybe I want this after all. Seeing my reflection in the mirror and my fast disappearing hairline was a continuous trigger of dysphoria that I've managed to shove aside in the past, but was finally coming apart at the seams. The feeling that my ability to present female would soon be lost forever, that I was going to ride off a cliff's edge and look like a bald, middle-aged man for the rest of my life created an intense, unbearable pressure on my being. Joining a discord group full of transgender folk also did not help. Before I knew it, the random thoughts became a serious consideration to transition, living as my male-self at work and my female-self at home (or vice versa actually, based on the latest situation).

The thought process went something like this. Maybe I could stay on a course of estrogen without letting my family or colleagues know and I could eventually have a body that was more female. Maybe the estrogen and testosterone blockers will finally stop my male pattern hair loss and even help some of my hair grow back. Ooooo, softer skin from taking estrogen? Sign me up! Wait but this is a serious decision that requires some thoughtful consideration. Oh but remember the lingerie advertisement you saw on Instagram where the model filled up the cups so nicely? That could be me! But seriously. I'm in my mid-30s, looking like an uncle most of the time with a receding hairline and I'm thinking of transitioning? I must be out of my bloody fucking mind. I'm not going to look like the girls I follow on Instagram. It's more likely that I end up looking like a weirdly feminine version of my current male self, in a gender limbo. Why do I want to crank life's difficulty to "extra hard"? (this is the logical side of my brain screaming at myself not to proceed). But the other logical half of my brain tells me that the changes are gradual and can be managed. There's no harm in giving it a try for a while and if necessary I can always try to hide the more obvious changes in certain ways. And hand on heart, I really do feel like I want to be female and seen as want. My brain was vacillating between "yes transition" and "no transition" at such speeds it was giving me mental whiplash. I had to stop myself, try to push the thoughts away and distract myself with work/kid. But this time was different. The floodgates had opened, the toothpaste was out of the tube. My metaphorical egg had cracked and the yolk was making a goddamn mess everywhere.  

To manage my thoughts I tried to lay out all my fears and by golly there were so many. 


Fear number 1 - My Wife 
My biggest fears concerned my wife. How was my wife was going to take this? This wasn't what she signed up for when she inked our marriage certificate. And when I first came out to her about my female alter-ego, I told her that I was not going to transition. If she rejects, will I decide to just live as I am now with an increasing nagging inner voice that I'm always incomplete? If she accepts it and doesn't decide to leave me now, will she leave me in the future? How am I going to be the "man" in her life? How is our sex life going to be impacted if I can't even get the "little brother" up? How could I be so unfair to her, choosing to live life on hard difficulty and expecting her to support me through this decision?

[At the point of posting this, I had already told my wife of my revelation that I was transgender and was considering HRT. She told me that while she doesn't fully understand my gender dysphoria and the implications of HRT, she will support me in my decision. Since then, we've had our share of ups and downs, which I am not yet ready to share. Things are ok for now, but it is still early days and the full impact has yet to come. We did recognise that moving forward, this will change our relationship, and irreversibly so. I feel like there is no one else that I should or need to care about this massive decision other than my wife's. But transitioning is not so simple, so there is a lot more communication to be done. Although it absolutely breaks my heart into many pieces to even think of it, to be fair to her, if she wants to press the exit button down the line, it is not something I will resist.  We still have love for each other, but whether we still stay together in the longer term is yet to be seen.]


Fear number 2 - My Family
Transitioning will be a massive shock to my parents who have zero clue that their son actually wants to be a woman.

First up, there is the logistics of hiding all the changes from them in the initial stages. I foresee that in year 1 and 2 it will not be too difficult but beyond that, how am I going to hide the physical changes from my family, especially two prominent changes appearing on my chests? While I can potentially bind my chest when I am at work and wear thicker shirts, my parents are likely to wonder about things, especially my dad who is quite perceptive. I also plan to grow out my hair, which will get a lot of questions on why I am looking unkempt. While the excuse of wanting to sport a manbun might cut it (barely), it will get repeated commentary and raised eyebrows.

At some point I will need to come out to them, which goes on to part 2; managing the fallout. Will my parents be disappointed? Will they feel like they have failed as parents? Will they think that I have lost my mind? Throw into the mix Asian expectations of me being the eldest son of the eldest son. Although it might be very difficult for my dad to accept this change, he has recently expressed that we should take action so we do not regret things in life, so I think I can explain to my dad logically my reasons for doing so. It is a coin toss though, since he is quite the traditional Asian father. As for my mother, an extremely devout Catholic whose life revolves around church, I can already imagine her going into shock and plunging deeper into church life, hoping to pray it all away. Doesn't help that the Catholic faith does not view LGBTQ folk and activities in a positive light. I also see her occasionally harbouring some anti-LGBTQ views, though knowing her, there is a lot of blind belief in that area. She is oddly strong in certain circumstances, but also emotionally fragile in others, so once again it is another coin toss on what the outcome will be.

I know some transgender folk are like "If they don't accept, f*** family", but I think this is not for me. I have a good relationship with my parents which I want to maintain. So I need to do my best to help my them accept that I am still their son, even though appearances wise I will look less and less like one. 

I can imagine how family gatherings will change in the future. Perhaps I will be the transgender family black sheep, the pariah who is automatically "uninvited" to all future events. Honestly I don't care if they don't want me around, but I'm more concerned about the hurtful words that they might say to my parents. I've set myself a goal that if I present as female, I will do what I need to in order to be my best self, and as undeniably female as I can be, to reduce buyer's remorse. 
[Post note: I have been told that such thoughts are very common in baby-trans. To be pretty so that people will not judge. But the reality is that society doesn't care. If they have it in their mind a negative perception, there will always be some imperfection that clocks you as "Male" that cannot be magicked away.]


Fear number 3 - My Work & Financials
Supporting myself is also a big issue. How is this decision going to impact my work? While I don't think I will lose my job as a result of this choice, the organisation I am currently working in is quite...traditional. There are also quite a fair number of Muslims and Christians, so views of transgender folk are likely slanted to the negative. While I plan to present male in my professional life for as long as I can, there might be a point where I am no longer able to hide the physical changes, or my views may change and I want to present as female. How will it affect the way I perform in the office? Deciding to transition will definitely slow promotions or close off certain job roles, since having a transgender leader might cause some discontent in the ranks. Bosses tend to also be of the older generation, so they may not want to work with someone deemed as "不男不女 (neither man nor woman)". 

I think I have enough money saved to last a while, but in terms of transferrable skills or networks that makes me a choice hire regardless of my gender, well that is uncertain. I do worry that my decision to live as someone true to my heart will screw up my finances in the long term and jeopardise the rest of my family. This decision could very well be the costliest decision of my life, and I'm not even factoring in the impending medical expenses and surgeries that I may have.

On the bright side, this has lit a fire under me. In 2 to 3 years, the changes will be difficult to hide, meaning that if I want to present female professionally, I need to make the necessary moves to change to a job or organisatiom that is more progressive. This means that whatever skills I need to pick up, I will need to do so now.


Fear number 4 - My Health 
While medicine continuously improves, medical science on transgender issues are lagging by a good number of years. This is simply economics; there isn't significant money to be made in researching transgender related medical issues because the population is too small.

Being on HRT for transwomen means taking estrogen and anti-androgens for life, and like any other drug, taking it regularly and over long periods does result in increased risk. A poor hormone balance results in increased risk of osteoporosis, and nobody really wants that. Another known risk of taking estrogen orally is an increased risk of stroke or Deep Vein Thrombosis (DBT), as well as greater stress on the liver due to the need to process the hormones, causing endocrinologists to be more conservative when prescribing hormones. While understandable, this leads to some gatekeeping by medical professionals. But the more fundamental issue is this. If I do this long term, would it really lead to poorer quality of life due to health issues when I am in my later years? (Uncertain. I need to read up more on this topic. So far it seems that the benefits of transitioning outweighs the costs). 

The other worry is insurance. The stance by insurance companies is unclear and can be quite varied. While some transfolk have made medical claims without too many issues, others have reported that their insurance policies were voided, despite having paid for YEARS. While it is understandable that there is now a potential increased chance of claim (due to say, higher risk of breast cancer for transwomen), this is really quite bullshit. People don't get their insurance voided for suddenly picking up smoking or drinking like a whale. Having this uncertainty with regards to insurance isn't great.


Fear number 5 - I will never pass
When I doll up, I don't look too shabby. But it takes time and the reality is that some of my features are quite masculine. My nose is larger that most women and my jaw is just a bit broader/longer in a guy kind of way. HRT might help by distributing fats and reducing muscle, but even if I decide to be a bit extreme and go for FFS, there are some parts of me that will be distinctively male. My hands and feet are both quite large/manly for my height, and I have a strong-ish looking back, so these will be immediate giveaway. 

But my biggest worry is my hairline. Unfortunately, the genetic gods have not been kind and my hairline has receded quite a bit for someone in his 30s, so it is a moonshot if my hairline grows back (I really, desperately hope it does). I am even prepared to spend stupid amounts of money and go through the pain of transplanting hair if it is necessary to restore my crowning glory. I'm not sure how successful such transplanting will be, but desperate times will call for desperate measures. 
[At the time of posting this, I am already on a regular dose of finesteride and gone for hair transplant surgery. So far the results are pretty good, although future hair transplants are necessary to give me a more rounded hairline]

As much as people say that women should not be overly concerned about their appearances, pretty privilege is a reality. People treat you better, or in the case of transgender folk, people feel a smaller amount of aversion. It reopens doors that would otherwise be shut. Transgender folk really cannot be faulted for obsessing over their appearance, because it is the difference between greater societal acceptance vs rejection, between being able to stealth vs constantly being clocked.


Fear number 6 - How deep does the rabbit hole go
A decade ago, I told myself that I would stay in the closet for life. 5 years ago I tried makeup and started going out in public. At that time I told myself that I would be happy to just crossdress occasionally and have no plans to transition. At the point of writing this post, I have decided to go all in and transition into a woman. It is absolutely shocking how my views have changed over the years (or perhaps, I always knew what I wanted but was too successful in convincing myself otherwise).

So the question remains unanswered. How far does the rabbit hole go? Will I want to change my name legally to Isabelle? Will I subject myself to facial feminisation surgery? Will there come a point where I want bottom surgery and change my legal gender, requiring me to void my marriage to my wife of many years? I'm quite sure that I don't want SRS, but in 3 to 5 years time will I have a different point of view? There is really no definitive answer.


Concluding thoughts
For crossdressers reading this blog who have an undercurrent of transgender and are in need of a push, here's a must read post on Reddit written by an aged transwoman who lived a textbook "good life" as a guy and suppressed her desire to be female, but when she discovered she had terminal cancer in her late-50s, she was overwhelmed with regret. And here's me. Wishing that I was daring enough to take the plunge years ago. We make our choices, we live with the consequences. No more regrets.

I suppose the name of this blog needs to change after this post. Isabelle is Transgender. 

I'm Transgender.

<Note: This post was written just under 1 year ago, but published later, as I was not ready to come out on this blog>
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