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Musings of a Singaporean Transgender


I was listening to a podcast that people do not talk enough about death when they are healthy, which results in problems when a sudden unfortunate event throws everyone and everything into chaos. This triggered random and rather morbid thoughts that I've always had. If I were to meet an untimely demise tomorrow, how would Isabelle's friends know that she is no longer on this world? Would my sudden silence in group chats and social media hint to friends that something untoward has happened to me? Or would they speculate that other circumstances have made me decide to socially purge Isabelle's existence? Given my current age, the latter seems a lot more likely. But if suspicions start to grow, how would Isabelle's friends even get the closure to their speculations? (assuming they needed such a closure). Would my friends be sad that they have lost a friend in life? Or was Isabelle's existence superficial and fleeting, like footsteps on a sandy beach; easily washed away and erased with each wave. Hopefully not. 

Thinking about death is a bit sad as it triggers all manner of emotions. But it is a good thought exercise to help prepare for the future. It made me wonder, how I would plan my posthumous activities.


1) What would I do with my female stuff?

If I could, rather than donating them to salvation army or selling them, I will give away all my stuff to fellow crossdressers who could put them to good use. I've accumulated quite a lot of women's clothing over the years. Counting everything that is in good condition, I have at least 40 outfits (majority are dresses), 10+ wigs of various designs, hippads and breastplates that are very usable, 5 pair of heels and a whole bunch of accessories that would make more than a few crossdressers very happy (after all, these are the items that have brought me so much happiness and joy over the years). 


2) Would I take the secret to the grave?

I did consider having a final request for me to be dressed up and cremated as Isabelle in a beautiful white gown. After all, though I could not be a woman in life, I could be one in death. But that might be a bit too much for my family to take since none of them knows of the secret. It's common for the top of the casket to be open for friends and relatives to pay their final respects. Imagine the shock/horror/disgust/incredulity when they walk past and see me as my female alter ego in there. So probably not such a great idea to leave my immediate family to explain and deal with the fallout of such a shocking public revelation. And since I'm dead, I'll be unaware and unable to help explain the reasons behind my dressing, leaving my family to face and clean up the "mess". So definitely no public revelations

As for coming out to specific people in my life, it will depend on who it is. Currently, only my wife knows of my crossdressing. So in terms of family members, I have my parents, my sibling and my kid. While I could reveal it to my parents and sibling posthumously, they probably would have enough to deal with already and don't need to be saddled with this revelation. There is no need for my secret to taint the good memories that they have of their son/brother. While my dad might be able to rationalise it, my mum is very religious and will struggle to come to terms with my crossdressing. As for my sibling, I think acceptance shouldn't be an issue, but not a must to know.  

I definitely want my kid to know about Isabelle at some point in the future though, when my kid is older and understands gender and its nuances. Because of how important my kid is to me, a secret as big as my female alter ego Isabelle should be shared. I want my child to know other facets of me, that would give a more complete picture of me as a father. My continuous struggle with gender dysphoria since young and the slow-blooming of Isabelle as my female alter ego has shaped the way I think and behave. It might help my kid understand my actions and behaviour when I was still alive (while I have taken great pains to hide Isabelle from my kid, small things will invariably leak out. This is an interesting article on the BBC about parents that kept the nature of the family business secret from their children). If my kid turns out LGBT in the future (never say never), knowing of Isabelle's existence might help to bring greater acceptance. 


3) Will I want to reach out to Isabelle's friends?

Definitely yes. Isabelle has made a few close friends in the crossdressing community and I feel like I owe it to them to inform of my demise. This would bring closure to the sudden silence. And perhaps, similar to how I feel grateful to have them as my friends, they also would feel happy to have had Isabelle been a part of their lives. I will definitely need to rely on my wife to reach out to them via my social media accounts. 

The other avenue that I want to reach out is a final farewell post through my blog, to conclude what I feel is one of the legacies I will be leaving behind. While my blog isn't widely read (given the subject nature), it is a collection of my thoughts and musings. It is a piece of me, immortalised in prose (well, that is until the Internet no longer exists or Blogger gets shut down). 


4) Would I regret having not lived/experienced my female self fully?

No. Could I have done more? Definitely. But do I regret not having lived? I don't think so. Isabelle has had her time in the sun. I have done much more than I have ever thought possible when I was in my youth, checking off many items in the bucket list. Isabelle has blossomed over the past few years, and despite inching ever closer to my 40s, my continuous struggles with dysphoria and some regrets (e.g. not doing proper skin care when young), Isabelle is currently her most confident and beautiful iteration. 
Back in 2019 I attended my first large scale gathering of crossdressers in Kuala Lumpur, Malaysia. Jointly organised by Malaysian and Singaporean friends, it was the annual bilat event that sees attendance of 40+ crossdressers from both sides of the causeway, all dolled up to the nines. I made some good friends in the community whom I've continued to chat with regularly despite having only met them once during that gathering. Due to covid, work and life, I've never been able to join subsequent gatherings since, so when the opportunity for a 3D3N solo trip came along I decided to head to Kuala Lumpur once again to meet with old friends (sanctioned by the Wife of course. She called it my "Eat, Pray, Love" trip. Not the right reference, but it was a movie about a solo trip of self-discovery). 

I planned for my 1st night to be at a fancier hotel so I could do an indoor photoshoot in a nicer setting, while the remaining nights were at a budget friendly hotel within walking distance of the major shopping areas.

Day 1 - Photography
Being mindful of the potential checkpoint jam due to the long weekend and not wanting to waste any time, I began my drive towards Kuala Lumpur at 5.30am. I cleared both border customs in record time of 15 minutes, which was very shocking as that has never happened in any of my trips to Malaysia (perhaps going in early is the way to go). Stopping only for a coffee and toilet break, I reached my first Kuala Lumpur hotel at 10.30am. Fortunately they had an available room so I got to check in super early. The hotel was located in the city fringes so there weren't too many sights for me to explore which was fine since my primary objective was to take fancy photographs within the hotel. After a quick lunch and nap, I ditched my male trappings and began the transformation into Isabelle. 

Self-portraiture using a DSLR on a tripod and flash photography isn't the easiest thing to do. Not only do I need to do my own makeup, I have to set up my photography equipment, use my handphone as a timed wireless-tether to trigger the camera shutter, while being the model being photographed. This is something I do regularly at home and they tend to be long drawn 4 to 5 hours events with around 200 photographs taken. And this was exactly what I did at the hotel. I started at around 4.30pm and after multiple outfit and position changes in the room, I finally called it quits at 11.30pm as I was too hungry and tired to continue. By the time I changed back to my guy mode, ate my cup noodles for dinner and rolled into bed for that sweet glorious sleep, it was already 2am. Was it worth it? Definitely. You be the judge.

(The dress I was going to wear for New Year's Eve. Photo taken of me from behind)


Day 2 - New Year's Eve
I originally planned to wake up early for a morning photoshoot by the hotel pool in a bikini (which would have been awesome), but there was no way in hell my middle-aged body was going to survive another day with 4 hours of sleep. So I opted for a late morning lazy breakfast, before I checked out of the fancy hotel and headed into central Kuala Lumpur. The second hotel was unable to cater for an early check-in, so I spent a bit of time wandering around Lot 10 and Pavilion mall to suss out the shops and potential places Isabelle could go shopping on the 3rd day. The latter had a Parkson Elite with a huge array of fancy dresses and cheongsams so that would be my go to. Day 2 however, was New Year's Eve and the main event. 

My friends had pre-booked a small table in a club/bar from 8pm till late. Events like this are hard to come by for us crossdressers, so looking like a million bucks was an absolute must. After nearly 2 hours of makeup, accessorising, sticking on fake nails and slinking into a sliver sequined mini-dress, I stepped out into the hotel lobby feeling like an absolute Queen.

I linked up with my friend and we headed over to the bar. Tapping on a nondescript door that looked like a maintenance access, it opened to reveal a fancy corridor that led to a swanky looking venue. I never understood the concept of a speakeasy, but I suppose some do enjoy the feeling of exclusivity. Also, this place was LGBT friendly, so being a speakeasy was probably a slight benefit in the more conservative Malaysia.

And so the night began! My guy self might be a homebody, but Isabelle...she loved looking glam and she loved the night life. There was a live band with a male lead singer who sang many suspiciously closet gay songs (there was George Michael - Careless Whisper, Lady Gaga - Bad Romance, Cher - Do you Believe). The food was surprisingly tasty for a bar so we stuffed our faces with food to hit the minimum spend (rather than drink ourselves silly). 

(Look at this fancy cocktail!)

As we enjoyed the music, food and vibes in the bar, we chatted like a bunch of old friends, despite it being the second time we've met each other. We spoke of how life was treating us, of other crossdressers old and new, of future gathering plans, of the scary but heady experience of coming out to cis-gendered friends, etc. And before we knew it, we started the final countdown to the new year, which was capped off with a bang by a cabaret show (Nicki Minaj/Ariana/Jessie J's Bang Bang really riled the crowd up). The DJ started playing clubbing music and people began dancing in front of the stage with the cabaret performers and each other. Isabelle couldn't help but join the crowd on the dance floor, jiving and moving with revellers. We finally decided we had our fill of fun at 2am, bade each other farewell, Happy New Year and parted ways.


Day 3 - Shopping
The 3rd day was considerably uneventful as it was a dedicated shop/eat/relax day. I didn't remove my red stick-on nails when I went for breakfast at the hotel in guy mode, so I got a number of stares from other guests sitting near me as I ate my nasi lemak. This was the first time I ever did something this bold, but I didn't care or feel nervous about it. The beauty of a being in a foreign country is that I will never meet any of these people in my regular life and there is very low chance of meeting someone who might recognise me.  

For my casual shopping trip, I chose to wear a recently purchased black denim babydoll dress that came up to mid-thigh, a style that is pretty popular recently in Singapore and very suited for shorter crossdressers like me. One thing I noticed was that a lot of people still wore masks in Kuala Lumpur despite the Covid pandemic being largely over (perhaps around 70%?). So in order to blend in I also decided to wear a mask when wandering around Pavilion mall. 

(Definitely not my best mirror selfie, but the only one I took that day)

I was still feeling tired from the earlier two days, so there wasn't a huge motivation to go crazy shopping. Plus the public holiday weekend crowd also sapped my energy a bit (I dislike crowds). So I zoomed in on my main objective of cheongsam shopping...which unfortunately reminded me of how unforgiving cheongsams are. A perfectly tailored cheongsam on a lady looks incredible; poised, classy and shows off womanly curves (just look at Maggie Cheung from the movie "In the Mood for Love"). But with the wrong material, design or cut, it is so very easy to look matronly, too top heavy, or *gasps in horror* like a Bak-zhang (Hokkien for rice dumpling. Looking like one means looking swollen with all the meat and fats wrapped too tightly) I'm quite slim and have decent curves with help from my hippads, but none of the cheongsams I picked made the cut. Also, they all cost $100 and there was no way I was going to spend that amount of money unless I was going to look a smashing 10/10.

(The tasty tasty Bak-Zhang. But eat too many and you'll start to look like one)

By 5pm, I was utterly drained and decided it was time for Cinderella to finally transform back into a fella for good. After a simple dinner, I met up with my friend again and ended the day with another chit chat (this time we were both in potato mode) over a milkshake from Five Guys.  


Wrap Up
My 3 day solo holiday to Kuala Lumpur was the longest consecutive period I have spent as Isabelle (which also included sleeping in nighties that I brought for the trip). Though it was quite tiring due to me being overly ambitious, I thoroughly enjoyed myself. I've always wanted to celebrate New Year's Eve in a sequined dress as Isabelle and I did exactly that, checking off another item on my bucket list. I'm not sure if I will get another opportunity to attend the next annual crossdressers gathering or go overseas dressed as Isabelle, but I'll make a wee bit of effort to see if my schedule (and life) allows me to. In the mean time, I'll need to think of more things to add into my significantly shortened bucket list.

I cannot believe that 2022 is over. 365 days, one more complete orbit of the Earth around the sun. It's been a hectic year with ups, downs and periods of sheer drudgery. One major positive is that Covid is more or less over. There's almost no restrictions and no more trace together QR code scanning. This meant that all the pre-covid activities such as gatherings, events, conventions and overseas trips are back. However, work has managed to successfully suck out the fun in many things, even in dressing up. So strangely, despite Isabelle going out a lot more in 2022, the year just feels less epic than 2021. This is not to say that I did not have a lot of fun. Though there wasn't another wedding gown shoot or interview, Isabelle did many things in 2022. I discovered a selfie studio and indulged in my photography and selfie inclinations. I went on a number of shopping trips and successfully controlled myself from buying too many outfits. I went clubbing as a she-devil for my second ever Halloween and thoroughly enjoyed myself.  I attended Anime Festival Asia (AFA) Singapore, my first Anime convention and looked pretty darn cute in a maid outfit with two pink ponytails. And I finally checked off a bucket list by attending a New Year's Eve party as Isabelle with good friends in the community, wearing a sequin dress that I believe I slayed in (yet to write the post. Will do so for another day). My perception of 2021 is definitely slightly warped, since 2022 was pretty darn eventful for Isabelle. I hope that 2023 will be better than both 2021 and 2022. 

Looking forward into 2023, to keep things simple, I've listed down 2 things to avoid and 2 things to do. It isn't just about my female self (after all, Isabelle appears an average of 1% of the time), but I'll angle it appropriately.


Things to Avoid
1) Stop selling myself short
Both in work, life and as Isabelle, I feel I have been self-censoring and selling myself short. I constantly feel like an impostor, second guessing my abilities. Am I good enough? Or despite my best efforts and hard work, will people find out that I am winging it half the time? Do they whisper nasty things about me during lunch time? Perhaps, and I definitely shouldn't care. I should do what is right and do it the best I can. As Isabelle, I keep feeling that even though I've progressed in leap and bounds since I first stepped out, I'm still not good enough. My hair isn't perfect, my hands are so veiny, my foundation is too cakey, etc, and each stare from the random passer-by is always a count to being clocked, rather than admiration of my outfit, even though I spend at least 1.5 hours putting everything together. Photography wise I don't know what I am doing or how to take good photos, even though the effort that goes into my pictures are already miles more than most crossdressers out there. So in 2023, I need to avoid being too much of a realist/glass half empty person and see the best in me. I'm doing pretty well all things considered.

2) Stop comparing with others
I have a natural human tendency to compare with others more successful. Sometimes I brush it aside, other times I feel absolutely shit about it at times. It could be a peer that is way more successful financially or career wise, or the young pretty influencer enjoying luxuries in life most girls dream of. But I seem to ignore the fact that I have a comparatively good life. While comparing has pushed me to improve and work harder to achieve better, I find myself sucked into an envy spiral that leads to paralysis and all manner of unhelpful, ugly thoughts. So this is something I need to work on in 2023. 


Things to Do
1) Prioritise family and friends
As I move past my mid-30s, I begin to feel that those who truly matter are a very small group. My parents who are growing older with each day, my wife who toils at work and does the heavy lifting at home, my kid who is growing so fast I suddenly that my adorable baby is now a chatty, opinionated toddler (still chubby and cute for now). My sibling and a few friends who have remained close over the years. For a time-scarce Singaporean, I must prioritise these important relationships. They are the ones who truly matter. I've admittedly neglected some of them, so in 2023, it is time to focus on this more. As for Isabelle, she has a small close group of friends whom she cherishes. While I recognise that a crossdresser's friendship can be fleeting and people may grow apart with time, may 2023 be the time to create more memories that we can look back in the future and feel warm in our hearts knowing that regardless of where we are in life 5, 10 or 20 years from now, we have enriched each other's lives when our paths crossed.

2) Live life to the fullest
Life is short, youth is fleeting. We live life within too many artificial boundaries and behave in ways we are told to behave. While some rules are important, our fears of breaking some of them hold us back from living life to the fullest. I've been having more YOLO thoughts in 2022 than I have ever had before. It's partly due to a mid-life crisis (i.e. is this all there is to life? Am I just going to do this till I retire at 68?), partly due to seeing people expire pre-maturely even before they retire, partly due to hearing people express regrets of being too afraid to do things and missing out on opportunities. So 2023 is the time to start living life to the fullest. While Isabelle isn't ready to come out to more people yet, there's more bucket list items to be checked off. Living life to the fullest also means spending more time learning, reading, exercising, doing things that brings me joy, and definitely a lot less time on social media.

Goodbye 2022, I leave you with mixed feelings. May 2023 bring greater happiness, satisfaction and new heights!
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