Musings of a Singaporean Crossdresser

I was only ever caught once by a family member for wearing a dress. The details of the day are a bit hazy; I was perhaps around 5 years old. I remember I was playing with my sister. One of us initiated that I try on one of her dresses. I don't remember how it looked, except that it was a white, red and blue flared dress. What I remember vividly to this day however were two distinct feelings. I felt very pleased and pretty when I wore my sister's dress. And I felt an incredibly intense shame when my grandmother caught me in it. I knew it was wrong; boys shouldn't be wearing dresses. I remember scrambling to hide in futility when I heard her coming from the living room, fearing that she would find out. When she told me that boys shouldn't wear dresses and asked me to remove the dress, I dearly hoped that she would not tell my father about it. The incident put me off so much, I never touched dresses or skirts for a long while after that.

A lot of the shame we feel as adults start off as simple boundaries that we learn as children and are reinforced over the years due to the way society is set up. Because these gender boundaries are so deeply rooted, the feelings of shame and the fear of deviating from accepted norms is typically intense. Both genders are subject to different types of "programming" from young, but for this article I will focus on boys, since that is my personal experience. 

Boys wear pants and girls wear skirts. Boys aren't supposed to like dresses and dolls. Boys aren't supposed to like pink or anything with ribbons or frills. Boys cannot cry because they should be strong. The list goes on. We praise little boys for feats of independence and bravery, chide them for actions or choices that are decidedly "female". 

Shame, is a natural result of shaming. And this shaming starts as early as kindergarden or primary school. Effeminate boys are ridiculed as gays, sissies, bapok*, ah-gua* and all manner of derogatory terms. "Why don't you dare to do <insert daring activity by children's standards>? Are you gay / a sissy?". Revealing any inclinations or curiousity in feminine accoutrements results in immediate teasing from peers and possible social ostracisation. Kids really are brutal. Only the bravest revealed their true selves and I was not one of them. I was a nerdy kid who just wanted to fit in and be liked. While I didn't partake in any shaming or bullying of others when I was at that age, I was fearful that hanging out with any who were slightly effeminate would cause me to be similarly ostracised. I also avoided anything that might suggest of my inclinations; no clothes with feminine colours, trying to be good at sports, etc. I even remember feigning boredom and pretending to be utterly uninterested when watching a transgender performance ("ladyboy show" as they were known) when holidaying with parents in Chiang Mai, though deep down I was enraptured! What beauty and what glorious outfits they wore! Note that these were the days of dial up modems, so I had near zero access to information to rationalise any of this. The media available on television or movies always portrayed transfolk as caricatures, perverted villians, or oddities to be gawked at. Talking to parents was obviously out of the question as well, since they were the ones who taught us the gender stereotypes in the first place. For those brought up in Christian or Muslim households where homosexuality and crossdressing is explicitly taught to be a sin, bringing up our "deviant" ways is out of the question; it might cause us to be scolded, beaten or thrown out of the house. Also, boys are supposed to be strong and they don't share their problems do they? They just grit their teeth, shove their feelings deep down and push on ahead (only for it to manifest as a kraken-sized monster that probably needs years of therapy to properly resolve). Because all this starts at such a young age, we build up decades worth of fear and shame. 

The fear of being labelled as gay is also tremendous for guys. It is somehow wrong to be gay, so any whiff from actions or words that might suggest one is such, is treated with incredible aversion. This can be being too close in proximity with another guy, taking too much care of your appearance, or even hesitating when being asked if you are gay. I thought this was hilariously captured in this short interaction between a stand-up comedian and his audience.

In Singapore, it is a running gag before enlistment and during basic military training (BMT) that you should not drop the bar soap in the toilet since the showers cubicles are without doors, lest you get boned in the butt by a horny homosexual hungry for sex. (This last bit is never explained, just left to be inferred after some immature chuckling by guys). In such an environment where being gay is met with derision, it is no wonder all guys who proclaim to be straight are immediately defensive of their sexuality.

You might wonder why am I bringing up the fear of being labelled as gay in a blog about crossdressing. In my view, shame of crossdressing is sometimes tied very closely with the shame of being gay, given how gender and sexuality are frequently confused with each other. Sexual shame is real. For a lot of us, I think we are terrified of being gay. For example, if I like wearing women's clothes and being a girl, does that make me gay? Does it mean i should like men? If I watch porn and I identify strongly with the actress, am I gay? If I am curious about butt play, does that mean I am gay? No, oh god no, I cannot be gay. Not only am I a pervert who inexplicably likes to wear women's clothes, I'm gay too? That is too much to deal with. It's like a double sin in Asian society or religious circles.

Shame is a huge issue faced by us guys who have a penchant for wearing women's clothes. We constantly ask ourselves, why does wearing something as simple as a pair of black stockings and a tight skirt feel so right, so good, so arousing? Why do our fingers tremble and hearts pound with excitement as we roll the hoisery up our legs and zip ourselves into a body-hugging dress? If it is so wrong, why do we love it so goddamn much? Why are we so deviant and perverted? The shame we feel is a significant hurdle that holds us back in our exploration to better understand our female selves. It delays our decision to come out to others, to experiment, to transition (if we want to). It is shame and fear that leads to over-compensation in the form of misogynistic, aggressive behaviour. It is this shame that creates immense guilt when we crossdress, leading to purging, self-loathing and depression. 

I have a fair amount of public interaction as Isabelle to date and I have made significant progress in being confident as her. Yet it is strange that i feel some manner of fear when people stare at me in public. When others walk past me I still look away, hoping not to see their quizzical gaze attempting to figure out if I am a guy under the makeup, wig and dress. Walking into the makeup aisle at Watsons (a local pharmacy brand) in guy mode still makes me embarrassed, especially if there is a sales person nearby. Somehow I have the irrational worry that I will be identified as a man in a dress. Even at home, despite my wife's acceptance of my alter-ego, I still feel very awkward dressing in front of her, especially when my outfit is too sexy or over the top feminine. It is as though I should be the proper guy she married, not a tart sashaying around the house in stilettos and a bodycon mini-dress. The emotion I think here, is shame. I admit that while a large part of this shame is from years of repression, it is also self-inflicted, since I am not being ridiculed by passersby, outed by sales assistants or judged by the wife. 

I decided to write this post because, while there are bold ones who don't feel this shame and are unabashed in pursuit of their personal happiness, I think many of us have experienced shame in our journey through life, to varying degrees. For those who have overcome it and are fully secure in your masculinity, I am truly happy for you. For those who still experience it like myself, there is a need to continue to work on rationalising and overcoming the shame, to achieve that inner equilibrium. It will take time and effort, but I believe it is all worth it. 

To end off this post, here's an entertaining and introspective video by Contrapoints about the topic of Shame. She explains the shame she felt, after dating a really great and good-looking guy post-transition, only to realise that she was actually a lesbian transwoman. She could only see herself in a long term relationship with a woman. Strange isn't it? That after overcoming years of shame and the social stigma of transitioning, she suddenly finds herself faced with the the greater shame of failing to be a model transwoman; i.e. one who likes men. As always, Contrapoints shares interesting perspectives with her own entertaining brand of dark humour, so do set aside some time to watch the video.

I don't think I can handle any more facial and body hair than I already have right now. 1 day before each planned dress up session, I will epilate my arms, legs and armpits, taking around 20 minutes. Epilating of my armpits are painful, but it is brief and tolerable. Facial hair removal on the other hand, is what annoys me the most. I used to shave, but it is impossible to cleanly remove all facial hair, resulting in dark "spots" that will poke through the makeup. I could hide the hair if I slap on enough makeup powder, but that's only feasible if I'm going full drag queen (which is not a look for day time shopping). So what I do is to pluck each individual strand using a pair of tweezers. This process takes at least an hour. One. Goddamn. Hour. It hurts a bit too, especially the parts just under the nose. While I have gotten used to the pain, it is the time taken that really galls me. Hair removal is a Sisyphean task; within a week my facial hair is back and I need to pluck the individual strands out again if I want to dress up.😒

If I had zero facial and body hair, Isabelle will be let out a lot more often. This is because the time taken to get ready will just be the makeup time (35 minutes if I'm quick, 1 hour if I'm more detailed), and there's no need to plan and sync my dress up sessions with my beard growth cycles. Yes you read right, beard growth cycle. Facial hair needs to be of a certain length and size in order to be plucked easily (and strangely, it's less painful). If facial hairs are too short or too fine, plucking them with tweezers is incredibly difficult and even impossible. After plucking, the clean look lasts for at most 2 weeks as they newly grown hairs are very fine and I can get away with just shaving. After that it is a mix of thick and fine stubble for around 2 weeks, meaning that having a fully clean look isn't possible. So I just shave regularly until my facial hair is uniform once again before I plan for another dress up session and do another round of dehairing. 

Some might think that plucking facial hair is insane. Perhaps it is. But it is also dedication 💪😣💪 How else do I get the truly clean look?

At some point in time, I'm definitely going to shell out the few thousand necessary for IPL/Laser/Electrolysis (I've not done proper research on which is the most cost effective) and get rid of my facial and body hair for good. The wife dislikes the facial hair anyway, so getting rid of it permanently is a double win.

(Clarke Quay on the Halloween weekend can be pretty fun)

While picking a place is important, the journey to your destination will be your first brush with other people. If you don't drive, public transportation can be a bit daunting for a first timer since you'll be in a confined metal vehicle with strangers for a duration. One way to avoid talking is to book a private hire vehicle using an App, so the ride is paid for and you don't need to tell the driver uncle in your deep baritone where you want to go. 

Another key tip is something I've mentioned this before and will repeat ad nauseam. For your first time out, please please do not wear your 5 inch stilettos, paired with a mini skirt and pantyhose. And don't overstuff your bras (deduct 1 or 2 cup size from what you think you should wear). While it might be a massive turn on for you, you'll stand out like crazy, which will make you even more nervous. Unless you've got an exhibitionist streak and enjoy people staring at you (yes, there are some who enjoy the attention), do try to dress a bit more simply.

Alright! So hopefully this post gave you some ideas on where to go for your first trip out in public. If you are still deep in the closet and still on the fence, make plans for it! Don't be like me and step out only when you're starting to get wrinkly. The younger you venture out, the more you can explore and have all the fun that crossdressing has got to offer.

5) Little to no economic benefit: Sometimes I call crossdressing a hobby. Even though it is much more than a hobby to me, the way I participate and interact with other crossdressers is very akin to other hobby groups such as scuba diving; we meet for meals, chat about regular life, exchange tips and techniques, share information about "gear", help and encourage each other, etc. Unlike most hobbies however, there is little economic benefit to establish a name for oneself by making the effort to become an expert in crossdressing and to grow the local community. The "gear" we spend money on is sumptuously offered by the fast fashion and beauty industry which is impossible to compete with. Active crossdressers in Singapore barely number in the hundreds, with those who are out of the closet typically in their 20s - 30s (i.e. limited free time due to work, has some spending power but more willing to spend on clothes than events). Running events for profit for the crossdressing community is definitely not profitable. The incentives for individuals in the community to run an event are therefore for the fun of it (read: once off), or to meet new crossdressers for sexual escapades.

Of course, Isabelle does win the fight at times. I recently posted a photo of Isabelle in the public r/crossdressing community on reddit for the fun of it and because my gender dysphoria was raising its head again after seeing too many young and pretty girls being effortlessly successful on social media (Social media is really horrid for mental health). The photo got around 1,000 upvotes and random positive comments after a week which gave me a bit of a dopamine hit initially, but it felt hollow when I thought about it. So what if I got those upvotes and comments? It did not serve as a balm for my need to feel accepted/liked/recognised as a woman. I still felt like a beardy guy who takes hours of effort to look like a fraction of what cis-girls could look like. I deleted the photo from reddit a week after posting, but not before some Instagram account promoting transgender women and crossdressesers downloaded the photo and posted it on their own feed (they did tag me, but didn't respond when I asked for it to be taken down).

The struggle against our base need to be accepted, but I believe that acceptance ultimately has to be from yourself and from people you meet in real life. Social media is very helpful in reaching out to others in the community and keeping in touch with friends. But it never will be the source of acceptance, and definitely not worth trading your privacy for likes and comments, especially if you do plan to still remain partially in the closet.