Musings of a Singaporean Crossdresser

Work has been extra stressful of late, with impending hard deadlines, multitude of presentations lined up and long work hours. There are days I just wonder if there is more to life than just working from Mondays to Fridays (maybe on weekends too), grinding at a job that doesn't give me much satisfaction, just to pay the bills, save for retirement and go for that occasional holiday. I suppose I am lucky not to have lost my job during this Covid-19 period, which has been challenging for many people. 

Nevertheless, work stress is what it is; a source of worry that makes one work harder, but also wish for some form of reprieve or escape. Unlike schooling days, where the stress of exam ends at the end of the year, work never ends. So the stress just lingers, spiking now and then as deadlines arrive. Some thrive on it, and a bit of stress is always healthy, but too much and the cracks start to appear.

For me, work stress causes my sleep to be less restful, increased grouchiness in the day and my gender dysphoria to flare up more than usual. Feelings of wanting to let Isabelle out and the desire to be a woman rush to the surface like a wellspring. It could take the form of wishes of being a beautiful model wined and dined at fancy restaurants in elegant outfits, or a elfin-faced cosplayer dressed in pretty lolita outfits. A simple photo of a girl with a skinny waist, glorious looking cleavage, or an elegantly worn outfit could send me to fantasy land. Anything to be away from endless emails and powerpoint slides. I'm sure I'm not the only one who feels this way.

As much as letting Isabelle out is a balm to my stress, I know that it isn't the cure. My brain is turning to a known form of relief and hoping that somehow, by partaking in dressing up and unrealistic fantasies, it would solve the root problem. Such thoughts are nothing more than escapism. There is a need to manage such emotions and make an effort to address the cause of the stress, rather than to attempt to run away from it.

As far as countries go, I'd say that Singapore is one of the safest in the world. Homicide rates are very low in Singapore and there's near zero chance of being shot (in part due to the lack of access to guns). Even petty crime appear to be rare, although the police will likely say other wise. The perception of a general absence of crime is so prevalent that people develop a sense of complacency, being perfectly comfortable to leave their bags to "chope" or reserve seats at the hawker centre. This is shown in the chart below.

I cannot imagine crossdressing in a place where people have easy access to guns and religious conservatives have very strong views about what a Man should and shouldn't wear. Perhaps I am wrong, but the presences of these 2 factors just raises the risk of being a recipient of hate crime significantly.

So if you're coming from out of town to Singapore and plan to crossdress, I'd say you'll be very safe. But do plan your trip around air-conditioned place, because the humidity and heat can KILL 😅

When I was still in the closet, I felt very alone and didn't think I would meet others who had a compulsion to crossdress. Websites at that time about crossdressing were largely limited to sources from the USA and UK. How was a crossdresser who was so deep in the closet and fearful of telling people about his secret going to find peers in Singapore? Well, fast-forward to 2018 and the internet is a very different place than it was before. Since I had come out to the wife, I decided to reach out into the community via forums (like the now defunct Sgbutterfly) and Instagram to chat with people similar to me and hear about their experiences. I'm glad I did so, because I discovered a whole community of local crossdressers in Singapore. We may be few and far between, but it is nice to know that we are not alone. 

It turned out that back when I was in my university days, there have been quite an active community that started off mainly from the forum Sgbutterfly. One of the main groups is Sggurls, by founder Nicole. Apparently in the group's hey day, the gatherings were pretty large, as seen from photos in old blogs like this. I don't think crossdresser gatherings in Singapore are this large and happening any more, partly because they aren't easy to plan. Many crossdressers in Singapore are also in the closet. Nevertheless, having chatted with more local CDs, I've come to know that there are quite a lot of small group gatherings that typically take place in hotel rooms or restaurants (for the bolder and more experienced). I've participated in some of these and it's really nice to have a safe space to doll up, chit chat, share dresses, tips, life stories and take a crap ton of photographs. 

I've also come to know, that a short 4 hour drive away from Singapore, in the bustling city Kuala Lumpur (or KL, as it is usually referred to), there's a vibrant crossdressing community. It's pretty amazing, because there are annual events organised by a core group, and crossdressers from various parts of Malaysia (Ipoh, Johor, Penang) drive down to attend the gathering. It has even attracted Singaporean crossdressers to join the fantabulous weekend escapade! Singaporeans and Malaysians, building diplomatic bridges one sparkly dress and sky high stilettos at a time! Unfortunately, there's Covid-19 raging everywhere, so going into Malaysia to join such an event will need go be on hold for now.

(So many crossdressers at the Malaysian event! The organisers are honestly amazing. I might get flak for posting a group photo publicly, but it is so grainy its impossible to make out anyone's features, and this photo was somehow found on Quora)

The last and most out of this world crossdresser gatherings are in none other than the LGBT friendly Taiwan! While starting out on Facebook, quite a number of very convincing crossdressers seem to be Taiwanese. Some background research on their profiles (*ahem* stalking) showed that not only does the Taiwanese crossdressing community have pretty regular gatherings in cafe and in each other's homes, every year they have massive 伪娘 gatherings. The photo of the 2019 event had upwards of EIGHTY crossdressers! It was like a mini company dinner and dance event with a stage, emcees, activities, photobooths and what not. Would be great if I could participate in one of their events sometime in the future. 

I don't think Singapore's community will be anywhere near the scale that Taiwan does it. But it isn't a competition, and as long as we find a friendly and like-minded group to regularly chat with and gather for dress up sessions, it's more than one can ask for.