Musings of a Singaporean Crossdresser

I chanced upon this gem of an interview shared in the sgbutterfly facebook group by the admin. I watched a bit of it without too much expectations and ended up making it through the whopping 3 hours long interview (broken into 3 separate episodes based on the themes and because it was too long). Kudos to the host for asking many interesting questions and for Aerie to share her story, along with giving well-balanced and thoughtful answers about many topics that transwomen and crossdressers face. Even though it was a long interview Aerie was pleasant and even slightly positive sounding, which was easy on the ears for sharing what could have very well been a heavy topic.

Aerie Rei is quite an interesting character, with a growing up story that I think many crossdressers and baby-transwomen can relate with, and a bit more. She came from a staunchly Christian family, spent 10 years in an all boy-school, started being drawn to everything female in Primary school, went through the phase of over-compensating by embracing toxic masculinity before snapping out of it, went to army, university, had a few girlfriends, worked in the Government, came out to her friends, colleagues and her parents, got kicked out of the house by her dad. She started her transition in 2020, at some point chose to be a porn star because it is something she loves doing and even flew to America for her first professional porn shoot. She was also fortunate enough to find love and married a Transman in Singapore (they have a polyamorous relationship). 

You could say, she had the typical middle income Singapore guy experiences and life trajectory before doing a major direction change. 

I think the interview is well worth the watch, especially if you're starting out or in the middle of your journey. If you've got no time, you can skip along to the parts that you are interested in. The host conveniently put a whole bunch of chapter links for each of his questions. 

Part 1 of the Youtube video is embedded below, while Part 2 and Part 3 are linked. Do have a watch! Alternatively you can also hear it as a podcast.

(The common time, money energy paradox...something is always missing)

I was walking past an elderly day care in my estate and saw a long line of old folks in their 70s to 80s, seated in chairs or wheelchairs, waiting patiently to be checked in by the day care staff in their 20s. Most looked like they needed varying degrees of physical help to move around. It reminded me to spend more time with my own parents who may be in a similar physical state in 10 - 20 years time. But it also reminded me of my own mortality; that in X number of years, even if I were to try an upkeep my body to the best I can, frailty is inevitable. 

Ageing is not just scary. It is utterly terrifying. No wonder religion has such a strong hold over humanity over all these years, promising that at the end of the tunnel when one has left the mortal coil there is a forever paradise waiting for all who were good and did the Lord's work (or a bad place for the naughty humans). Women fear the passage of time, because it robs them of youth and beauty. The skin sags and lines that mark the passage of time become apparent on the face, that no amount of plastic surgery can hide. Even men who are generally less concerned about appearances are not immune to the effects of time. If it were so, there wouldn't be a multitude of hair loss products in the market and drugs like Viagra that promise performance in bed as though he was a young man. Flipping through both history and mythology, we find kings spending hoards to find the potion of everlasting life, only to fail and pass on.

In my opinion, appearance and beauty is very important to the crossdresser; even more so than to actual women. This is because women have other things of importance to them that bring them satisfaction and a sense of accomplishment, such as a partner, children, career, etc. However for the crossdresser, his female self exists for more or less a singular purpose. To be the pretty woman that the crossdresser imagines himself to be. Which makes the concept of ageing even scarier, because beauty fades with age. I've already heard multiple crossdressers telling me that they are dressing as much as they can because they feel that they are growing old. And that they will quit crossdressing once they are no longer young enough to look pretty/cute (I highly doubt that, but we'll see).

But in a lot of the conversations, a certain number keeps coming up. 40 years of age. "Once I hit 40 I will stop crossdressing because I can no longer look pretty/cute anymore.". Holy shit. If there is any truth to that number, it makes me about half a decade more to expiry. Fortunately I think there isn't. But the big FOUR ZERO scares many people, because looks and physique does go downhill (the dreaded dad bod and beer belly becomes tougher to fight back). I'd be lying if I told you I wasn't worried. Even hitting 40 scares my male self, let alone the narcissistic inner woman who only wears 4 inch stilettos and obsesses over her social media likes and comments. There is always a tinge of envy when I see younger (and prettier) crossdressers coming out into the scene, because I missed that opportunity when I was younger. And I can no longer do things like grow out my hair, tying it into a man-bun in guy mode and styling it into a fabulous hairdo if I'm hitting the town as Isabelle. I recently tried on a Seifuku (Japanese school uniform) at iWan Selfie Studio and damn did I feel like an aunty trying to look like a young school girl. Fortunately I still have a relatively longer runway to pull off the sexy office lady look that is my forte.

A close sister who's a mature crossdresser told me that she can only pull of aunty looks now, but she tries to do a hot aunty. She puts in the effort and looks fabulous, but she also did say that age makes it hard to want to crossdress, since it is more challenging to meet the feminine ideal (especially the one in the mind). That having said, I also know of other crossdressers in their 50s - 60s who are going super strong, and are dressed so much more than they have ever done in the past (to be fair, it was a lot harder to meet up with others in the community and buying clothes online was non-existent 30 years ago). There is a huge sense of YOLO as well from these mighty gals, some of it because their children have flown the nest and if they do not live now, then when. It means that the drive to crossdress may dull with time, but it will still be there. Therefore I find it hard to believe that crossdressers who claim that they will quit after 40 will truly do so. I haven't got there yet, but I don't think I will quit at 40. But I definitely need to tamper my own expectations as I age, and instead be thankful that Isabelle did have many glorious days in the sun.