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.