Musings of a Singaporean Transgender

 

(Transgender Youtuber Contrapoints. She is as gorgeous as she is funny)

Contrapoints: "I'm aware that the conventional beauty standards are a racist, sexist, ablelist, fatphobic, transphobic social construct designed to preserve power relations and sell products. But does that awareness mean I desire any less to be conventionally beautiful? Well...no. I want it more than ever! The problem with the intellectual exercise of critiquing things doesn't usually affect my desires that very much. So what am I supposed to do? Sit here in silent contemplation until my desires finally align themselves with the interests of the international proletarian revolution? Oh Fuck the revolution! I want to be a pretty rich girl."

If you haven't already discovered her Youtube channel that already has 1.6 million subscribers (as of Sep 2022), then you totally should. She is eloquent and hilarious, discussing gender related topics covering various view points. Putting out an excerpt from her video doesn't do her delivery of the topics any justice, so do watch her video on beauty, which I have linked down below. Do note that her videos are generally quite lengthy (30min or more).

So today's post is about beauty. Everyone wants to be beautiful. It is a desire that spans across sexuality and gender. Straight, gay, lesbian, bi, male, female, trans, non-binary folk all want to be beautiful. Don't we all follow Icons and Influencers on social media, wishing that we could look like them and enjoy the high life that their good looks has supposedly conferred upon them? Pretty girls seem to effortlessly become models and enjoy sponsorships, gigs, fancy meals, jet-setting lifestyles, supposedly high pay to sustain said lifestyle, and throngs of fans throwing themselves and dollars at them; things that the plain Jane (or John) on the other side of the phone could only dream of having. Winning the genetic lottery grants what is known as "pretty privilege" that opens many locked doors. 

It isn't just about the potential monetary benefits. As much as we need to learn to love ourselves, being conventionally beautiful undeniably makes us feel good. Looking into the mirror and being able to think "Damnnnnnn girl you look good" sends that dopamine rush to the brain. And when others heap on compliments, a person's self-confidence is boosted even further; to dare to speak a little bit louder and hold the head up a higher. Being acknowledged as pretty  makes us feel great about ourselves. 

For us crossdressers, the need to be beautiful is the ever present goal...or at times, the only goal. The highest prize is the ability to successfully emulate the conventional feminine ideal in appearance. Almost every single post on Reddit, Instagram, Facebook and other social media platforms used by crossdressers is screaming to show off this ability, demanding the Internet for validation with the question "Am I Pretty?" (Yes. Yes I am pretty. Tell me I am pretty. Goddamn it, like, upvote and share this post you anonymous, faceless other person over the internet. Even better, shower me with comments in a thousand different ways to tell me how pretty I am. Do it! Tell me I am pretty. Please? Oh and don't forget to follow). And the community itself feeds this need, along with a boatload of envy. Our chat groups regularly discuss how gorgeous some other young crossdresser or transwoman is, never mind that said beauty may be a product of plastic surgery or photoshop. We regularly lament our various flaws and fervently wish that we had this or that physical traits.

When asked: "Will you ever consider transitioning?", a reply I sometimes hear is "I'm too old to be pretty" or "Only if I can be pretty". Heck, that is the reply my brain tells myself too. For many of us (myself included), should the decision to transition be made, I don't think simple facial feminization surgery alone is adequate. If I am going to slide down the slippery slope of spending hard earned dollars on plastic surgery, suffering the physical, social and financial pain of transitioning, I'm sure as hell going to make sure I come out the other side looking drop dead gorgeous. After all, in for a penny, might as well be in for a pound. (Looking like Lalisa would be sweet. Or the goddess that is Gemma Chan.)

Will the quest and need to be beautiful for ever end? For us crossdressers, I don't think so. But it is important to recognise that in our pursuit of it, we should not let it consume us with envy. 

I was recently chatting with a newbie crossdresser who commented that she came out to her friends recently, who turned out to be very accepting of her gender fluidity, positive vibes all around. But she also read my blog and had wondered if she was too daring to take such a big risk. Of course she was already out to her friends during a dinner and dance event, so any potential worries about being too open was well, moot. She was in her early 20s, so she attributed the difference in risk tolerance level between herself and what I seemed express on this blog to be a generational thing.

Damnnnnn. 

Your girl Isabelle is old. No offence taken from the conversation of course. But it was interesting to hear that perspective. The newbie crossdresser had already attended Pink Dot SG, got support from her female friends (and some male ones), and was all ready to explore her female self. She did not strongly identify as transgender (at least not yet), so in terms of the mindset and need to be recognised as female, I'd say she is considered to be a crossdresser. The willingness or the feeling of readiness to come out this early certainly did not occur to me when I was her age. Back then, I was all ready to keep this secret to myself and take it to the grave; a scared crossdresser in her room wishing to set her inner girl free but too worried about the implications of letting the world know. To this day, other than my wife, nobody else knows. Granted, this situation is of my own design, since there isn't really any great reward if I let others know about Isabelle (other than seeing their amazement).

Of course, the internet was fledgling back when I was in my 20s, smartphones weren't really a thing yet and online shopping only just started. There were some resources on the internet for transgender folk but very limited. 

So there is a generational gap. Quite a number of crossdressers my age are still in the closet, whereas the younger ones seem to be exploring their female selves in public and coming out to their friends at a much earlier stage. There is definitely some bias of course; we are only aware that someone is out of the closet when their social media presence reflects as such and not everyone is so open on social media, so statistically speaking this observation cannot be verified. Nevertheless, I think it is definitely a fact that members of Singapore's LGBTQ+ community, crossdressers included, are coming out at a younger age. The internet has showed that our "condition" isn't unique and it is ok to be a bit different from other boys and men.

Now more importantly, with this realisation that I am a product of my era, other than attempting to look hot and lean into the MILF vibe, how is an ageing crossdresser going to stay relevant? Hmmmm

After a really busy period, I finally carved out time to take a day's leave and have some Isabelle time to scratch the shopping itch. So on a Monday morning, I did my usual dress-up ritual; wake at 7.30am, travel from my parent's place to my own house, eat a heavy breakfast that would double up as lunch (eating in girl mode is a bitch and messes up my makeup, so I usually skip lunch on dress-up days. Also I dislike being stared at while eating), shave, bathe, dig out all my crossdressing stuff from the storeroom, spend an hour putting on makeup and transforming into Isabelle by around 11am. I'd then travel to the usual mall to visit my favourite shops. I'll pick out pretty outfits that catch my eye, try them out in the changing room, take some photos/videos, before heading back home by 3pm to round off the day with an outfit test of the new dress and wig I had purchased online a week back. There wasn't enough time to do a proper photoshoot at home, so I just used my phone camera as I was also feeling lazy (which resulted in underwhelming photos that weren't sharp enough). By 4pm I had to de-drag, take another shower, pack my stuff back into the storeroom, before travelling to my parent's house just before the evening peak our traffic.

Whew. What a day. I sated my desire to shop, but I felt....unsatisfied. Dressing up felt like a rush and obligation, which left me even more tired than a full day in the office. A chore consisting of a huge to-do list to tick off. Like why did I even bother to dress up? 

I did a quick poll with my Instagram followers and feeling unsatisfied after a dress-up session wasn't a unique experience. Although the rush that I put myself through during each session was definitely a contributing factor, I don't think it is the only reason. I've been in the normalisation phase for quite a while now and have this niggling sense that my desire to dress up has been waning. The feeling of having been there and done that has sapped away the novelty of dressing up. What is the next thing for me to look forward to when dressing up? I've even started looking around for another bridal studio to do another photoshoot, but it feels like another attempt to blow a couple thousand dollars to chase the next hedonistic high. I get to wear some pretty gowns for a couple of hours, have photos to show off for it, and then what? 

I suppose this is why people retire from crossdressing after a number of years. Because the hassle of dressing up outweighs the derived satisfaction and desire to do so. 

I do have some plans to make dressing up seem less like a chore, starting with getting rid of my facial hair. I absolutely detest having to grow out a week long beard to a decent length before spending one hour plucking the individual hairs out for a truly clean look. I've gotten used to the pain but the time it takes just annoys me to no end. I do also hope to dress for a longer period without having to rush back home for my parental duties, so that will require some logistical arrangements. Halloween and Anime Festival Asia (AFA) is coming back this year with all the covid restrictions removed, so I also do hope to at least try attending in costume, which would make things a bit more interesting.