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Musings of a Singaporean Transgender


I don't have statistics to back me up, but based on conversation with other crossdressers in the community, revealing to your girlfriend or wife that you crossdress is akin to playing Russian Roulette with your relationship (except there are probably 5 bullet rounds in the chamber rather than 1). There's a chance that you'll come out unscathed, but the odds aren't very high. 

I've heard too many stories of regular(?) relationships that crossdressers have ending in divorce or breakups. Or if the relationship continues, there is simmering unhappiness and discontent on both sides; the guy will be feeling constrained and unable to freely dress up, needing to take various measures to do it behind the wife/girlfriend's back, causing the crossdressing behaviour to go deeper underground. While the girl will either be constantly wondering if her husband/boyfriend is crossdressing behind her back, or be worried that he might decide to transition all of a sudden to live as a woman full time, which is way more than she had bargained for.

Vivienne, a New Zealand based blogger who writes about crossdressing, documented on her blog how her marriage began its downwards death spiral three years after tying the knot, when she revealed to her wife about the crossdressing. It was quite a sobering reminder that even in a developed nation fairly accepting of LGBTQ members in the community, when things hit close to home, acceptance may not be as easy. 

I can fully understand the conundrum that wives and girlfriends have to face when their special other owns more high heels than they do and prefers wearing dresses and lacy lingerie over regular men's wear. Their entire mental model of how their partner should be is thrown out of the window in an instant. Flip it around and it's easy to appreciate how challenging it is for wives and girlfriends to accept crossdressing. Imagine one day during dinner, your wife/girlfriend tells you that she prefers to bind her breasts, wear boxer shorts to bed and shave her beautiful long hair into a crew cut because it makes her feel whole when she dresses like a man. How many husbands and boyfriends will balk at such a revelation? Of course, women wearing men's clothes in society is more easily accepted than men in dresses, but if you turn the masculinity dial up a few notches (like the scenario I described), it requires a big shift in the guy's mental model of how his spouse should look and behave. 

The "woke" community can argue to say that gender is not as binary as society has led us to believe, people should recognise this fact and be more accepting if their partners want to dress in a certain way. They are right that there should be greater acceptance. But the harsh reality is that society is very clearly split into two genders; Male and Female. We have been raised for years to identify certain traits as male and female, boy and girl (even my kid at 18 months old could easily point out whether someone was an "Uncle" or "Auntie"). It is going to take a good number of decades before gender fluidity can truly be accepted in mainstream society....if it is ever going to be at all. Even as a member of the LGBTQ community, I struggle to get my head around the bearded lady or guy in a dress aesthetic that some in the community go for (e.g. Billy Porter, Conchita Wurst); let alone someone who is less immersed in the concept of gender fluidity. 

Not all crossdressers' marriages end in tragedy of course (although I believe they still remain the minority). Apart from myself, I know crossdressers whose wives accepts their husband's crossdressing. For a lucky few, their wives even partake and enjoy the crossdressing behaviour. Usually for such cases, the secret is revealed prior to marriage, meaning that it was a conscious decision by the wife to decide to marry the guy despite knowing his feminine inclinations. 

For younger crossdressers who have yet to commit to a relationship, it is a good rule of thumb to be upfront about your crossdressing inclinations from the start (perhaps on date 3 or 5?). It is heart-wrenching to see a potential partner do a 180 degree after you do your big reveal, but think about how much more painful it is when you have committed years into a relationship and have marriage looming ahead. Or worse, you have a house and kids, but are suffocating inside because you are unable to let your female self loose once in a while (trust me, once you move in together with your wife, the "oppressiveness" and latent stress you feel from the need to constantly hide is no joke.). Although society isn't 100% ready for gender fluidity, each generation is becoming more accepting and open. So be just a bit braver while you have youth on your side.  

And just like that, 2021 came to a close. It lasted 365 days and was just like any other year (not counting those weird leap years), yet the crossing of the threshold from 31st December to 1st January somehow seems extra special. It is usually a time of reflection; of achievements attained and of things yet to be done. A time of stock taking and planning for the future. A moment for realignment of goals (if this was left neglected over the year). 

I would consider 2021 to be a fantastic year for Isabelle. Despite the pandemic, I checked off a number of bucket list items as Isabelle. Felt like it was done really long ago, but I went for the bridal photoshoot as Isabelle at the start of 2021. I was interviewed as Isabelle by the local media network Must Share News as part of their "Ask Me Anything" series. I wrote more on this blog than I had ever done which helped the blog reach the first page of google if you search for the correct terms. And both my makeup and personal photography skills to take photos as Isabelle have improved significantly. To think that I only starting using makeup and came out to my wife in 2019. Not to sound like I'm stroking my own ego, but I have improved massively as compared to when I first started out. 

With such a great run for Isabelle, it does make me wonder; what more lies ahead for her? What would the next achievement over the next 365 days in 2022 be? My bucket list feels a lot fuzzier than it did before and I don't know what the future holds for Isabelle. Sure, there's still a lot of things that I have yet to do (such as rocking a NYE's party in a sequin dress that I don't even own right now), but I strangely feel a weariness when I crossdress, definitely due in part to energy-sapping work/life stress from my male self spilling over and affecting my desire to dress. The excitement of crossdressing also isn't as intense as it once was given that the amount of preparatory work required to do so often seems not worth the effort (growing out a 1.5 week beard and moustache and spending 1 hour to pluck our the hairs individually is a damn chore). Despite knowing that social media is bad for mental health, I still follow beautiful people for inspiration, but am also reminded of my fleeting youth, financial obligations that doesn't allow for extravagant spending (on gowns, yes), and inability to reveal my female side to more people. 

But it is the natural course of crossdressers. And one should always stay hopeful for beautiful moments and unexpected achievements that lay ahead. The year just started and with the pandemic waning (hopefully), there is much to look forward to. So to my most ardent readers, thank you for reading my blog, stay beautiful, cheers to 2022 and to the great times that lay ahead 😁



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