Musings of a Singaporean Transgender

One of my primary struggles with gender dysphoria have been about desperately wanting to see a woman reflected in the mirror. With makeup and the right outfit, I could see that. But my bare-faced self looked androgynous to me on good days and male on bad ones. Being regularly gendered male by random strangers further confirmed that perspective to me, causing a lot of internal turmoil, with swirling emotions of anger, disappointment, envy, resentment and resignation. I felt that FFS was necessary for me, chiseling bone to carve out a feminine appearance. But I also struggled with the shame of so intensely desiring FFS, instead of working to accept myself as I am. Friends and my wife have said that I conflated passing with beauty. But the line between wanting surgery to look less masculine versus becoming conventionally beautiful was blurry; the latter to me was an added bonus, as long as I didn't keep pursuing surgery after the initial FFS.

A year ago, I decided to book a consult with a surgeon in the US. Popular doctors in the US have long wait times stretching years, so I knew I needed to get my foot in the door, even though I was still early in my transition. This involved waking up at 5am to call the clinic due to timezone differences and jumping through a few hoops because the clinic thought my call was spam and blocked my number initially. But I eventually secured an appointment for a consult about 1 year ahead (it has gotten worse for this doctor. Currently waitlists are almost 2.5 years).

"Why US?", many have asked. Taiwan, Thailand and Korea were nearer, cheaper, and had surgeons familiar with Asian faces. The waitlists were also much shorter, with prelim consults done using photos sent over to the clinic. While that was true, being unable to properly research a surgeon's credentials based on reviews, having a language barrier and a tendency for surgeons to be aggressive in the amount they corrected that resulted in unnatural results was something that bothered me. I wanted my post-surgery look to be natural. Korea had an added problem of "ghost doctors", where the person doing the surgery isn't the person that you signed up with. Patients usually have no idea of the bait-and-switch until something goes terribly wrong. It was my face and I couldn't bear the thought of living with a less desirable or failed result, after significant financial expense and enduring the long recovery process. Knowing myself, I would regret, hate and shame myself forever. I needed to go for something with assurance of success.

Finally after what felt like an eternity of waiting, it was time to fly to the US. It was 16 hours of flight time, with a 2 hour layover in Japan. By the time I rented a car and drove to my accomodation, I had travelled for a full day. As I lay down on the bed exhausted, I wondered what the f*** I was doing travelling this far. Maybe Asia was a better choice. I missed my family, I had to tell my kid and my parents I was on a "work trip", and felt like I didn't have anyone to lean on in this trip. I didn't do much research so I booked an accomodation near the hiking spots and premium outlet mall. Which turned out to be so far from the city, there was no way I could partake in the queer nightlife. So my exploration as Isabelle was mainly shopping 😅

The consult took place on Day 4 of my trip. I parked in the medical building at 8.30am, to go for a CT Scan of my facial bone structure before my doctor's consult at 10am. The purpose of such a scan is for the doctor to have a clear understanding of the facial bones, where and the extent to which they can shave down the bone to obtain a more desirable structure. After paying for the scan, a technician led me to lie down on a flat bed, which moved me back and forth into a donut shaped scanner. This process was fast, taking only about 5 minutes.

I returned to the clinic to wait for my doctor's appointment. I had been feeling anxious before the trip even started, so this morning was no different; this was the consult I had been looking forward for so long, an expensive but necessary step forward in my transition. I sipped on my coffee and ran through my notes on the questions and issues to bring up to the doctor. Soon enough, a nurse called my name and gave me an elastic cloth to hold back my hair for the consult. 

The doctor was a young, confident man who spoke with a reassuring voice (important for doctors). After exchanging pleasantries, he asked me about my personal history, past surgeries, my medical and social transition journey. He was quite amazed that I took a 16 hour flight to the US just for this consult and also asked me why I didn't go to Asia. As his specialty was in brow and nose work, and because I was paying out of pocket, he suggested that for any chin and jaw work, it would be much cheaper for me to do it in Korea, adding that he would provide me with recommendation of a clinic in Korea.

 

He started the consult by asking me the parts of my face that bothered me and wanted to change. In descending order of dysphoria causing parts, I told him that I wanted to advance my hairline, smooth out my browbones, reduce the size and bulbosity of my nose and sharpen my jaw and chin a bit to give it a slightly sharper V-angle. I told him that I liked my cheekbones, even though they protruded outwards a bit and another Taiwanese clinic had recommended for zygoma reduction. He listened to me before giving his opinion on what he felt should be done, limits and risks. He touched the skin of my forehead and said that it was quite tight, so he would only be able to advance my hairline to 70% of where he would have liked it, with the difference easily made up with a future hair transplant. He felt the texture of my nose to determine if it was skin or cartilage, to get a sense of how challenging the rhinoplasty would be. Based on the number of surgeries recommended, he estimated that it would take 6 hours, which was just at the self-imposed limit that he doesn't exceed. For those who are curious, the doctor's notes are shown below:

It would have been a happy day, if not for a curveball during the consultation. In the medical history form, I had indicated that I have a heart issue, where some general anesthetic drugs are not recommended, due to the potential to increase the risk of ventricular arrhythmias, which could lead to cardiac arrest. Unfortunately for me, the drug not recommended for use was exactly the one used in the clinic. And no surgeon wants to have a risk of their patient going into cardiac arrest midway through what some might consider elective surgery. He told me that there was a low chance that he would be my doctor, but he would like to get my medical records and run them through his anesthesiologists to see if alternatives were possible.

I felt time stop and my heart drop so hard I nearly broke down in the clinic. It was a terrible feeling, to feel like there was another road block to my transition. I had been looking forward to this surgery consult for more than a year and this was a huge wrench in my plans. One step forward, two steps back. If this doctor didn't go through with my surgery, I needed to go back to sourcing for another doctor that I could trust, wait even longer for a surgery date and delay my transition further. I could feel the anguish building in my chest, which I shoved back down with my well-practiced skill of suppression. On hindsight, perhaps I should have just let myself cry in the clinic.

The doctor could see the disappointment on my face and tried to reassure me that there could still be a chance for the surgery to proceed. We moved on to taking photographs as part of records for consultation, before moving on for the final chat with his assistant, who explained logistical details about the cost, post-care needed, payments, how to go about booking the next surgery date (April 2026 was the earliest) and other details. With that, it was the end of the consultation. The main objective of my trip to the US was done, albeit with a new, unexpected detour.

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 questions on gender identity, sexuality, being a crossdresser or being trans/enby.

Dr Natalia Zhikhareva, or Dr Z PhD as she is known on her Youtube channel, is a clinical psychologist specialising in transgender care. The gateway video I'd like to share is about crossdressing, sexuality, gender identity and gender dysphoria. Throughout my journey, I had been incredibly confused about who I was and how the 4 things tied in to each other. The video takes a while to get into the meat of the topic, but it is very illuminating to those who are still confused about who they are, especially crossdressers who have to navigate the boat load of shame associated with liking clothes of the opposite gender.

Dr Z has many, many gems in her youtube channel, that I have been devouring over the past year during my commute to work. She also made a 7 part series for partners of trans-identified individuals, which I had shared with my wife. In the videos, she provides a balanced position to partners that doesn't blindly take sides.

It's rare that clinicians who truly understand the struggles and journey of individuals who struggle with gender issue provide free content that is very useful. So do have a watch if you want to find out more about matters of gender. If you do like her videos, you can also support her channel by subscribing.

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 belief that one is unpassable, despite evidence otherwise. "Brainworms" is a catchy and an easy way to describe the thoughts of self-doubt that even the most passable crossdressers and transgender have. Taken to the extreme, it might push some to go for surgery after surgery, to correct the "flaws" or masculine markers that one perceives. We regularly jest with each other that it isn't just HRT that is needed, but a thorough regime of deworming.

I've been having a bad case of passability brainworms recently. Catching a glance of my furrowed brows in the mirror, I think about my browbone being overly prominent. The toilet downlight casting an unflattering light on my face, accentuating all acne scars and my angular jaw makes me feel annoyed. In my quiet moments, I think about the genetically gifted, youthful transwomen that I will never measure up to, and I regularly worry about my ability to pass without makeup or surgery. It takes good friends to bonk me on the head and bring me back to earth again. But the cycle repeats, to the point where I already feel "paiseh" for voicing the same concerns to the same group of friends. 

I believe there are two phases to the bad case of brainworms. The first is before/during the transition phase, when there is uncertainty associated with transitioning and constant worry of how the future in 2 to 3 years time will look like. I can't speak for early transitioners, but I'm sure for those transitioning in their 30s or later, the need to tear down work/life/social structures built up over decades makes the brainworms especially numerous and wriggly. This is where I am right now, where I keep seeing an uncle in the mirror and cannot envision how the future will be; whether HRT will allow me to come closer to my appearance goals, whether growing out my hair is even possible, whether I could look decently female without a full face of makeup. 

Someone shared the photo below, which I thought was rather apt. The changes associated with transitioning such as fat distribution, electrolysis and hair growth takes time, so it is important to be patient. Even non-bodily changes such as developing a style that suits us, gender-aligned mannerisms and voice training isn't achieved in a few months.

(Please don't say "Yassss Kween" 😖)

The second phase is after transition. There are certain physical traits that do not change due to HRT, which can continue to be a source of some dysphoria. Height, size of ribcage (which results in a strong looking back), size of hands and feet, lack of hips, etc, the list goes on. While they don't create mental discomfort as regularly, society has a way of bringing typically dormant dysphoria to the fore, be it intentionally or unknowingly. There's always some random ass***e who points out that you are using the wrong toilet. Or an accidental misgendering by a stranger even though you felt extra passable that day. The reality for most transgender folks is that regardless of how "successful" one gets, there are always days where the brainworms come out to play. 

These days, I almost exist entirely as my regular uncle self "Bob", since I don't dress up much. But Belle still lives rent free inside my head, reminding me of her presence in many different ways on a near daily basis. Which made me wonder...how would it feel as a "regular" guy, with no female alter-ego and no gender dysphoria? It is unfortunately, an entirely hypothetical question, since people with gender dysphoria will never get rid of it, and regular guys will never get to feel it. 

We spend so much of our waking hours thinking about gender matters; in youth, we wondered why we wanted to literally be in the shoes of the opposite gender, struggled with feelings that such thoughts were deviant and weird, yet circling back to think about them again and again.

We deal with the fervour of wanting to dress as our female selves on a regular basis and obsess over creating opportunities where we can do so. This fervour is especially bad when there are long dry spells, but the withdrawal post dress-up isn't great either. 

When we finally get to dress as our female selves, we fret about imperfections in our makeup and attire, overly magnifying all the masculine attributes we think will cause us to get clocked. We worry that our feminine-inclinations will be discovered by people we know and be branded by others as a pervert or a weirdo. 

We deal with varying degrees of body dysmorphia, being concered about appearance related issues that plague women, like weight, height, skin, attractiveness...except our base template is male, so the gap between our current and preferred looks is usually even larger. There's always unhappiness with certain parts of the body and the envy that comes along with it. Do you know how damn annoying it is to see a pretty girl on the train and think "I wish my skin/features/hair was as good as hers. But that will never be possible. Oh well."

So much of our time, energy, effort and mental bandwidth is spent because of gender dysphoria, soothing it in one moment and fighting it in the next. Life without gender dysphoria would be so much easier I think. Much less guilt, fear, discontent and obsessing over gender stuff. Just need to be a regular guy doing regular bro stuff. 

A bit of a disclaimer, if you're reading this post hoping for some shocking revelations that Isabelle is going to reveal about herself, then you're in for a disappointment because there aren't going to be any. What this post aims to do is attempt to lay out my thoughts as I try to uncover the reasons for why I crossdress. 

When I first started this blog back in Aug 2020, I wrote about a short post on why I crossdress. I likened it to a hobby that makes me feel beautiful, sexy, desirable, feminine and is a bit of a turn on. I did it because it makes me happy. While all of that still holds true, with multiple experiences of dressing out in public, talking to various people in the community, that short 3 year old post seems a bit dated and overly simplistic on review. It feels timely for a deeper dive into my base motivations for crossdressing. 

The easiest reason for why I crossdress is to attribute it to me being transgender. I don't deny that I am somewhere along the spectrum. But is the measure of how transgender a person, the extent to which one feels dislike/discomfort with the genitalia and male gender markers one was born with? By that yard stick I don't think I'm that transgender (if it can even be measured), although it could also be a case of being conditioned to feel ok with my male self over time, after years of suppressing. I've written about my struggles with gender dysphoria, that while I don't actively and continuously hate my male body, there are moments where the wish to have certain female traits rears its head. Like how great it would be if I have a nice pair of breasts that would let me pull of that dress with a plunging neckline. Or more delicate facial features that would let me pass much easily. I do have a great deal of envy for guys who have delicate facial features like those korean boy band singers. They really don't need to do much to be easily perceived as androgynous or female. 

I did consider whether I was gender fluid, enjoying flitting between male/female modes and sometimes blurring the two. But I find that my embrace of gender fluidity is binary; there is no in between. I am either decidedly male when in uncle mode, or unquestioningly female (dresses, skirts, stilettos, long hair, makeup, hippads, forms, the full works). My need to crank up my female "traits" to the max is so intense, gender fluid doesn't seem like the correct label. 

When I feel the urge to dress, I put on a full face of makeup and spend the day shopping or taking self-portraits. It's fun, but recently I've felt like the whole process was...pointless. For shopping, it felt like aimless wandering, hoping to uncover a special outfit that would make me excited (I'm usually unsuccessful in finding that special outfit). For self-portraits, it is still enjoyable and I like the final product, but after posting it on social media I usually get this weird sense of dissatisfaction. I check my phone repeatedly, feeling momentarily glad with each compliment before emotions crash down into a disappointing feeling of how meaningless it all is. What am I trying to achieve each time I dress up? To have people tell me that I am pretty, in order to validate my desires to be female and be the balm for my crushing insecurities? How many people do I need to tell me that I look good, will I be happy/satisfied? Because it feels like I will never be happy/satisfied. Am I an addict constantly chasing the next high? With so many of my bucket lists checked in the past year, I don't know what else remains. Cosplay and photography are currently a good avenue to direct my energies to sate the desire to be even better, since it is quite technical and my skills are amateurish. But I foresee that this will exhaust in time; and then what?

I've also been wondering whether my recent bouts of pensiveness is due to hitting a perceived "ceiling" in my ability to present as female. While I've never been better at my game, I'm left wondering if this is really the best that I can be? Because I still don't feel I am female enough, or good enough. (I sound like I'm going through a goddamn mid-life crisis). I can pour money and time into levelling up my skills in makeup, learning to style hair, getting the best wigs and even derma procedures to improve my skin. But this "ceiling" feels like it isn't just skill and product related, but physically limited. 

This however is quite a scary line of thought. Are my inadequacies and dysphoria nibbling away at my barriers to take the next big leap to break this perceived "ceiling"? Will I be satisfied only when I start taking hormones to make me develop female characteristics like budding breasts and softer skin? Or will crossing that line lead to me wanting to push the envelope even further with facial feminisation surgery to gives me a undeniably female face? Is a full transition the be-all and end-all? Will it be the point where I am truly satisfied?

Hello fellow sister,

This is a letter to you, especially if you're relatively new to crossdressing or have been in the closet for the longest time. 

While our origin stories and the winding routes that we take through life are different, we all share a single commonality; our penchant for wearing women's clothes. It may have started inexplicably when we were 5 years old, or it only started in our 20s as part of a dare. But regardless, the activity of dressing up as a woman brings us great joy.

There is an unparalleled thrill solely reserved for us crossdressers when we unwrap our online purchases, to slide that new little black dress up our body and step into a pair of stilettos. The heart thumping in the ears and the quivering fingers as you feel the rear zip enclose your body in the dress. How is something deemed so wrong by society able to feel so damn right?

Remember, this is your life. While we are accountable to the people closest to us and have different responsibilities, this is the only life we have and we have to live it to the fullest (sorry readers who believe in the afterlife or reincarnation). So make plans to be financially secure and enjoy the female side of you, hopefully in public too. 

Most importantly, love yourself, always.

We are all cis-men who love to wear women's clothes, and that's ok. After all, women's outfits are f***ing gorgeous and better than boring men's clothes 😆