Musings of a Singaporean Transgender

Recently one of my friends in the crossdressing community discovered the joys of shopping in public and oh was she a woman unleashed. Her outings enfemme spiked and she bought a lot more outfits than she would normally do so online.

Online shopping has its perks, but it doesn't hold a candle to shopping in person, at least for us crossdressers. Ever since I started shopping in person, I've stopped buying Isabelle's items online unless it cannot be easily obtained in brick and mortar shops (e.g. wigs, breastforms, costumey outfits) or I see something I really like at a good deal. Why wait 1 week for the few selected outfits to arrive in the mail when you can have IMMEDIATE gratification in the shops? Go to the right malls and you can even hit multiple shops in a few hours. Efficient and effective.

My friend's shopping spree is not unique to crossdressers in their discovery phase and it is likely temporary, so the damage to her wallet won't be that large of a bomb. 

Crossdressing is expensive. As if upkeeping 1 wardrobe isn't enough, crossdressers need to spend money buying pretty outfits on a regular basis to satisfy the inner girl (almost like maintaining a mistress, except she also shares your body 🤣). I think it is ok to buy clothes as long as you can afford it and it makes you happy, but my advice to crossdressers who have just discovered the joys of in-person shopping is to avoid what I term, the "shopping chain reaction".

The "shopping chain reaction" is where you buy 3 outfits on your first shopping trip. You wear one of these outfits during your next trip and buy 3 more pretty outfits. And 3 more in your next shopping trip. It's basically a nuclear chain reaction but for shopping (very geeky I know 😅). Before long, you'll have more outfits than actual outings to wear them. You need to realise that changing rooms have really soft lighting that makes you look great in the mirror, and because you're sort of on a high during these initial shopping trips, every other item you pick looks great in the mirror. I've wasted money buying so many clothes I no longer wear because I don't like them anymore.

So to do your wallet a favour, here's my 3 rules to rein in your inner shopaholic:

Regardless, have fun on those shopping trips! Sales people really don't care whether you're a guy in a dress or not, as long as you're a serious customer. So don't worry too much about being clocked or using your male voice if you really need to speak. Just own it and enjoy your moment enfemme. 

The term "Paradox of Privacy" usually refers to the disjoint between expressed privacy concerns and actual online behaviour. We bemoan about how big tech companies like Facebook and Google harvest our personal data and insidiously selling it to advertisers, yet we still willingly let them do so in exchange for convenience (google maps) and desire to show off our lives to the rest of our friends (sharing of photos/videos on Instagram and facebook).

I think crossdressers also suffer from their own paradox of privacy, albeit different from what I just described. We express privacy concerns and worry about the impact should our crossdressing inclinations be made known to our partners, relatives, friends and colleagues, yet we keep wanting to show our female selves to people, be it on Facebook, Instagram, Reddit, private chat groups, etc. This paradox is only faced by crossdressers who have not yet come out fully to the rest of the world (which is a lot of us in Singapore).

The crossdressers' paradox of privacy stems from the deep desire to accepted by others, to be told that you are beautiful/pretty/successful as a woman. Although the desire to be praised in this age of social media applies to everyone, for crossdressers the desire runs a lot stronger because acceptance is less easily available. Family and friends may not be understanding, while mainstream society has a tendency to brand a crossdresser a deviant (Crossdressers generally are viewed as perverts who get off from wearing women's clothes. It is really difficult for a crossdresser to explain that he likes to wear women's clothes because it makes him feel sexy or turns him on. A good parallel would be people who are into BDSM). Because acceptance and praise is in limited amount from a crossdressers' immediate circle, he turns to social media for likes/comments/praise. The way we "show-off" is also very narrow; usually it is a photo of ourselves dressed in out latest purchase, asking on social media if we are pretty or outright stating that we are. I am guilty of that measuring my success as a crossdresser by this same narcissistic metric.

Isabelle has social media accounts which a restricted group of crossdresser friends has access to. At times I think to myself: Why am I being so scared? I've taken so much effort to level up my skills to look sufficiently convincing as a girl, shouldn't I just make my accounts public or post my photos on more public platforms like reddit? This way I could be admired more, feel a sense of success, drive more viewers to my blog. But then my risk-reward alarm bells go off and my guy self slaps sense into Isabelle, reminding that such "recognition" that I seek on social media is ultimately meaningless and will not solve the deep rooted self-esteem and gender dysphoria issues that I face. And in exchange I flippantly squander away my privacy.

I chanced upon this gem of an interview shared in the sgbutterfly facebook group by the admin. I watched a bit of it without too much expectations and ended up making it through the whopping 3 hours long interview (broken into 3 separate episodes based on the themes and because it was too long). Kudos to the host for asking many interesting questions and for Aerie to share her story, along with giving well-balanced and thoughtful answers about many topics that transwomen and crossdressers face. Even though it was a long interview Aerie was pleasant and even slightly positive sounding, which was easy on the ears for sharing what could have very well been a heavy topic.

Aerie Rei is quite an interesting character, with a growing up story that I think many crossdressers and baby-transwomen can relate with, and a bit more. She came from a staunchly Christian family, spent 10 years in an all boy-school, started being drawn to everything female in Primary school, went through the phase of over-compensating by embracing toxic masculinity before snapping out of it, went to army, university, had a few girlfriends, worked in the Government, came out to her friends, colleagues and her parents, got kicked out of the house by her dad. She started her transition in 2020, at some point chose to be a porn star because it is something she loves doing and even flew to America for her first professional porn shoot. She was also fortunate enough to find love and married a Transman in Singapore (they have a polyamorous relationship). 

You could say, she had the typical middle income Singapore guy experiences and life trajectory before doing a major direction change. 

I think the interview is well worth the watch, especially if you're starting out or in the middle of your journey. If you've got no time, you can skip along to the parts that you are interested in. The host conveniently put a whole bunch of chapter links for each of his questions. 

Part 1 of the Youtube video is embedded below, while Part 2 and Part 3 are linked. Do have a watch! Alternatively you can also hear it as a podcast.

(The common time, money energy paradox...something is always missing)

I was walking past an elderly day care in my estate and saw a long line of old folks in their 70s to 80s, seated in chairs or wheelchairs, waiting patiently to be checked in by the day care staff in their 20s. Most looked like they needed varying degrees of physical help to move around. It reminded me to spend more time with my own parents who may be in a similar physical state in 10 - 20 years time. But it also reminded me of my own mortality; that in X number of years, even if I were to try an upkeep my body to the best I can, frailty is inevitable. 

Ageing is not just scary. It is utterly terrifying. No wonder religion has such a strong hold over humanity over all these years, promising that at the end of the tunnel when one has left the mortal coil there is a forever paradise waiting for all who were good and did the Lord's work (or a bad place for the naughty humans). Women fear the passage of time, because it robs them of youth and beauty. The skin sags and lines that mark the passage of time become apparent on the face, that no amount of plastic surgery can hide. Even men who are generally less concerned about appearances are not immune to the effects of time. If it were so, there wouldn't be a multitude of hair loss products in the market and drugs like Viagra that promise performance in bed as though he was a young man. Flipping through both history and mythology, we find kings spending hoards to find the potion of everlasting life, only to fail and pass on.

In my opinion, appearance and beauty is very important to the crossdresser; even more so than to actual women. This is because women have other things of importance to them that bring them satisfaction and a sense of accomplishment, such as a partner, children, career, etc. However for the crossdresser, his female self exists for more or less a singular purpose. To be the pretty woman that the crossdresser imagines himself to be. Which makes the concept of ageing even scarier, because beauty fades with age. I've already heard multiple crossdressers telling me that they are dressing as much as they can because they feel that they are growing old. And that they will quit crossdressing once they are no longer young enough to look pretty/cute (I highly doubt that, but we'll see).

But in a lot of the conversations, a certain number keeps coming up. 40 years of age. "Once I hit 40 I will stop crossdressing because I can no longer look pretty/cute anymore.". Holy shit. If there is any truth to that number, it makes me about half a decade more to expiry. Fortunately I think there isn't. But the big FOUR ZERO scares many people, because looks and physique does go downhill (the dreaded dad bod and beer belly becomes tougher to fight back). I'd be lying if I told you I wasn't worried. Even hitting 40 scares my male self, let alone the narcissistic inner woman who only wears 4 inch stilettos and obsesses over her social media likes and comments. There is always a tinge of envy when I see younger (and prettier) crossdressers coming out into the scene, because I missed that opportunity when I was younger. And I can no longer do things like grow out my hair, tying it into a man-bun in guy mode and styling it into a fabulous hairdo if I'm hitting the town as Isabelle. I recently tried on a Seifuku (Japanese school uniform) at iWan Selfie Studio and damn did I feel like an aunty trying to look like a young school girl. Fortunately I still have a relatively longer runway to pull off the sexy office lady look that is my forte.

A close sister who's a mature crossdresser told me that she can only pull of aunty looks now, but she tries to do a hot aunty. She puts in the effort and looks fabulous, but she also did say that age makes it hard to want to crossdress, since it is more challenging to meet the feminine ideal (especially the one in the mind). That having said, I also know of other crossdressers in their 50s - 60s who are going super strong, and are dressed so much more than they have ever done in the past (to be fair, it was a lot harder to meet up with others in the community and buying clothes online was non-existent 30 years ago). There is a huge sense of YOLO as well from these mighty gals, some of it because their children have flown the nest and if they do not live now, then when. It means that the drive to crossdress may dull with time, but it will still be there. Therefore I find it hard to believe that crossdressers who claim that they will quit after 40 will truly do so. I haven't got there yet, but I don't think I will quit at 40. But I definitely need to tamper my own expectations as I age, and instead be thankful that Isabelle did have many glorious days in the sun. 

It's been quite a few years since Isabelle first stepped out in public. I still remember the thumping in my chest, the fear of being recognised as a guy wearing a dress, the shame when someone stares at me for longer than usual and the euphoria of unexpected validation. But mostly the fear, which wells up from the gut up to your throat and paralyses both the mind and body. The first time out in public was so very scary. But I've gone out in public many times since that faithful Halloween of 2018 and I feel a lot less stressed when I do so now as Isabelle. 

Don't get me wrong, going out en-femme still has its stressful moments. Stepping out and returning home as Isabelle is always the most stressful because I really don't want my neighbours to see me. I still don't like eating out as Isabelle because I'll be seated in close proximity with other patrons who can gawk at me with impunity (more importantly, the long hair really gets in the way). And being stared by multiple uncles/aunties in quick succession at the shopping malls still throws me off a bit. But I'm no longer uptight about stepping out and feel relaxed most of the time. There are a number of reasons why this is so. I've gained more experience being out in public and honestly, Singapore's a pretty good place to crossdress since it is safe and people generally mind their own business. I've improved my skills since 2018 and confident that my style allows me to blend in the best I can. I'm also a bit older too, so there is the element of YOLO where I don't really care as much about whether people realise I am a guy in a dress or not. To top it off, mandatory mask wearing due to the Covid pandemic has allowed me to hide my manly lower jaw and larger nose, which helps me to blend in even more. 

Although being in public puts a crossdresser in a "riskier" position of being recognised as male, a lot of this risk isn't consequential unless it is a partner/friend/relative/colleague who recognises you. And usually if it is your friend, I'd think they'll generally be understanding and supportive of what you do. The upside of going out in public en-femme is that I get to do a lot more regular day to day things as a woman, with shopping right at the top of the list. It also creates opportunity for validation, which is something that so many of us crave. These moments are usually fleeting and insignificant to any other observer, but to us crossdressers who aren't fully out yet, it means a lot. Even something simple like being called Ma'am by the bouncer at the club during my first time out in public was validating. My makeup was middling at best, my wig was unnaturally shiny and I could barely navigate in my 4 inch heels, but it still felt great. 

I've since had multiple occasions where I interacted with other people who seem to be perfectly comfortable with Isabelle. A sales assistant giving me a small nod and smile when I picked out items to try in the changing room. The bridal studio's makeup artists and photographers who were casually chatting with me throughout the entire photoshoot, occasionally telling me that my female self looks pretty decent (service for the paying customer perhaps. But the comments didn't come across to me as fake). I've also had a lot more close encounters with random strangers recently when I visited iWan Selfie Studio in March 2022, due to the relatively small studio and the close proximity which I have to be in with other patrons. I don't attempt to use a "girl-voice", so whenever I spoke everyone else in the room would be able to clearly tell I was a guy, but none really bat an eyelid about it. Most of the ladies just gave me a smile when we occasionally made eye contact and went back to busy themselves with dressing up and taking selfies/tiktok videos. 

Two episodes at the selfie studio were especially validating. The first was when I overheard a bunch of 3 young chinese gals commenting among themselves about wanting to take photos in the 2D themed room I was in. I wasn't too keen on the room so I told them they could use it and one of the girls went "Ehhhhh, 你是男生!" (the Chinese equivalent of "Omg you're a guy?!"). Inside I thought to myself, YESSSS I passed 😆 (the ladies were quite self-absorbed so they probably didn't pay me much attention earlier). Another episode was during my 3rd visit to the selfie studio on a weekday, when a gaggle of aunties in their 50s who were just done with their session were hanging around the lobby and chatting with the owner about the package prices. I had picked out a sequined bodycon dress which fitted me surprisingly well and started taking photos in the kaleidoscope tunnel. A few of the ladies started observing, commenting to each other out loud about my slim figure, about the poses I did, how experienced I must be, about the more professional mirrorless camera used (It was very Singaporean auntie behaviour). I was so embarrassed and taken aback when 4 of them suddenly whipped out their own phones to take photos of me, that I stopped my own selfie-taking to engage in a bit of a conversation with the curious aunties. It turned out they truly thought my look was well put together and just wanted to take some photos (unacceptable from a personal privacy standpoint, but understandable when you view them as harmless Singaporean aunties with a compulsion to take photos of anything and everything). One of them requested for me to take a selfie with her, while another requested for me to do a twin pose with her in the kaleidoscope tunnel, both of whom I obliged. Another eagerly showed me the slow-motion view she took in the starry theme room and told me I absolutely had to do the same thing. They were also genuinely interested to find out how I remotely controlled my mirrorless camera using my phone. I resumed my phototaking, which got a few more ooos and ahhs from the aunties before they left for their belated lunch.

To suddenly have random people wanting to take photos with me because they thought I looked pretty was incredibly weird but trippy. I've never had so many compliments about my looks in my entire life, which threw me off but definitely felt validating. I know this all sounds superficial, but there is a tinge of pride when I think of the effort I put in to pass and how far I have come since my pre-coming out days. When I shared the strange episode with my wife later on, she quipped that I was the drag queen in a sequin dress that everyone wanted to take a photo of post-performance (LOL 😂). Perhaps that was the reason why they wanted to take photos of/with me. I'm uncertain if the aunties figured out that I was a guy or not though. Some of them surely did but never mentioned to me. But being able to just engage people normally without them sounding weirded out or giving me a puzzled stare is great. 

I wouldn't start putting myself in situations where I have close encounters with others, like going to a bar and actively chatting with others. Although most people wouldn't mind, not everyone is so accepting of crossdressing behaviour.  Nor do I want to be out to my family/friends yet, and sure as hell not to my work colleagues (Knowing about my dual-life as Isabelle still remain a "need-to-know-only" basis). But I'd continue to do more regular things as Isabelle and enjoy every moment of being her without a care of being clocked (up to a point). And if there is a need to strike up a conversation with others in my baritone, I definitely wouldn't mind doing so.

Although this seems to be an easy question to answer, I do get asked more frequently that I expected. They're mainly asked by those in the closet, although some who have a bit more experience dressing up do ask me occasionally as well. 

There are some dedicated clothing shops for crossdressers online, originating in the USA or United Kingdom. However, I do find that these shops seem to be a product of an older era, when it was much hard to buy items online and anonymous delivery or self-collect from delivery lockers (e.g. POPStations, Ninja Collect, Blu, etc) was not an option. Marketed towards crossdressers, the range of available styles are narrower and tend to be a lot pricier for equivalent items sold in regular brick and mortar shops for women. Nevertheless, they do have certain specalised products which can be very good (e.g. high quality silicone hippads), niche outfits that appeal to certain segments of the community (e.g. 100% satin or latex maid outfits, super frilly petticoats, ballet stilettos) or outfits for crossdressers with very large and masculine physiques. For regular day to day clothing however, you're better off buying from the large number of options that women have. I've tried to list down the various choices available to crossdressers and why you may want to go for them.

For crossdressers who have started to step out in public, big clothing chains such as Zara, Mango, Cotton On, H&M, Uniqlo, etc, are fantastic to shop at. The selection is massive, there are frequent discounts and the clothes are regularly refreshed so you can come back in a few months to whole new range (yes, fast fashion isn't great for the environment I know). One of the best parts is that sales assistants generally don't both you, and because of the large floor area you can do your shopping without bumping into other patrons. Not that it really matters too much, since the ladies in such shops are usually absorbed in picking out clothes, while the men are just wandering around in boredom or scrolling through their phones. 

Unfortunately, if you're still in the closet, you may need to purchase clothes without being able to try them, which is a real bummer as the clothes may not fit well. Return policies are quite liberal, but that means walking up to the counter staff again in guy mode to ask for your slinky sequin dress to be exchanged for a larger size. Very nerve wracking for the newbie crossdresser.

I haven't gone into such small shops because I still feel nervous about interacting with sales assistants using my guy voice as Isabelle, and I know I will feel obliged to at least buy something if the sales assistant is super friendly and accommodating. To save my wallet, I've largely avoided such small shops. But I know crossdressers who have done so and they find the experience great. You'll get the full attention of the sales assistant who is eager to help you out and let you try on the clothes, in order to close a deal. I think sales assistants are also usually bored out of their minds.

Just because shops are smaller does not mean that you will not be able to find clothes that you like. The benefit of smaller shops are that the clothes could potentially be cheaper, negotiation is possible and they may hold certain range of clothing not typically found in the big clothing chains (e.g. Taiwanese styles, Evening/bridal wear, some can tailor make outfits if you're willing to pay for it, etc). 

Oh free returns are really the best when it comes to online shopping. Zalora and Asos were such important platforms that helped me to try on a wide range of outfits when I was still in the closet and unable to shop in person. I was able to order a larger selection of clothes and only keep the outfits that looked good on me, which helped to keep my crossdressing expenditure down. They helped me to gradually figure out the types of outfits that worked for my body shape and allowed me to explore styles that I would normally have not picked as a 1st or 2nd choice. In addition, the selection from these shops are massive and sells everything a girl needs; you can buy dresses, tops, skirts, pants, undergarments, sleepwear, accessories, makeup, brushes, bags, etc from either sites. Currently, around 80% of Isabelle's wardrobe is purchased from Zalora and Asos, which is pretty significant. Zalora has amazing delivery speeds locally; there were days that I got the package the next day even though I didn't sign up for next day deliveries. Buying from Asos will mean you get your goodies a bit longer, as they need to be shipped from overseas. Asos also tends to be more expensive than Zalora, although the quality and range of their clothes can be even larger (e.g. I could never find proper sequin dresses on Zalora, but Asos has loads of them).

Zalora did change it's free returns policy in 2021 to a conditional free returns policy of minimum $50 purchase however, probably due to the large number of people abusing the free delivery and returns policy. To make sure I qualify for free returns, I usually make a massive order from Zalora (like 15 outfits) and throw in some guy clothes I actually need for good measure. This way, all it takes is for me to keep 2 outfits to cross the $50 threshold. 

(This is the model, not me)

Point of caution though, unlike Zalora and Asos, such shops may have fancier packaging and sometimes state the contents of the package within them. If you currently live with your parents and the shop you want to buy from is unable to deliver them to a self-collection delivery locker, you may want to give the shop a miss. 

There are a few downsides with using these platforms though. If you don't like an item or there are defects, returning such purchases can be a pain in the butt, especially for Taobao. Although some crossdressers like to buy dresses from Taobao, I find shopping on the platform tiring as cheaper shops have the bad habit of using photos nicked from other places, while more expensive shops with better quality clothes can end up being pricier that buying locally. As such, I only buy items from Taobao that I cannot get from local shops, such as wigs, cosplays, breastforms, clip-on earrings, unique lingerie and large sized high-heel shoes (Local shops only sell up to size 41, while I am a size 43). I generally treat my purchases from Taobao as disposable. 

Do take note that Lazada and Shopee has this bad habit of stating the contents of the package on the delivery label, which is very annoying if you live with your parents and are delivering to your home. Taobao does not have this problem. The other downside of using Taobao, Lazada and Shopee apps, especially if you do so on your guy mode phone, is that ads for items your browsed on these apps will bleed all over the place. I've seen cheongsams and wigs recommended to me when I was reading the news on my BBC app. Not great if trying to be discreet.

I added Shien to this category, as it feels like an English-language site for clothes sold on Taobao; massive range of clothes and budget friendly, but quality is a dice roll and the photo of models look like it was nicked from somewhere. I personally haven't bought any clothes from Shein, but I have heard a mix of good and bad feedback from other crossdressers. 

I've done my fair share of browsing on Carousell and find quite a number of clothes from popular local clothing brands being sold. This means that if you're hankering for a particular outfit from a local clothing brand, there is a chance you'll find it on Carousell. The downside of course is that the seller may not have your size. In addition, I find that the listing price has a tendency of being only at a slight discount from the original price it was retailed at. Nevertheless, being a 2nd hand online shop, a good deal is bound to pop up every now and then.

Refash is a decent option for buying clothing on the cheap if you don't mind wearing something second hand. Their selection is decent and the price is wallet friendly too, which is very important for us occasional girls. The downside of Refash however is that you have to shop in person and it is like trawling through the bargain bin; you don't know what you'll be getting and if you do see something you like, it is the only piece and there's a chance it might not fit. So go in with zero expectations and you might turn out to be lucky.

After a while, you'll come to realise that buying clothes isn't the difficult part for crossdressers. It's making the most of your money and spending them on items that fit you properly, rather than wasting money on outfits that don't look good. It is important to know your body type, measurements and styles that flatter your body, rather than outfits that look great on a svelte, doe-eyed model in her early 20s. Pretty girls can wear a gunny sack and still pull it off, so if you do buy clothes online, try to cover the model's face, or try to imagine whether the outfit will still look good if it were 1 to 3 sizes larger. Takes a bit of practice and wasting some money buying stuff that doesn't work, but you'll get there eventually. 

Unfortunately, 2022 has started off with...mountains of work. It began piling up in the end of 2021, but once January came around everyone suddenly woke up and the pace became even more frenetic. Between long exhausting hours at work, watching a kid who refuses to sleep early, household chores and squeezing in precious moments of me time, it meant that writing has unfortunately taken a backseat. Heck, even Isabelle hasn't made an appearance since Christmas. Given a choice between 2.5 hours of thorough dehairing and makeup just to let Isabelle appear for a day and catching additional sleep, I'll take the latter thank you very much.

So I apologies to avid readers of my blog, sorry for the inactivity! Things should stabilise soon and I'll find some time to write more regularly. I've got a few ideas bouncing around in my head which is good news...just got to write them down when I'm less bleary eyed and not nursing a headache. 

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 😁

The lack of a safe space to dress up is a common problem faced by crossdressers around the world. Usually the inclinations to crossdress start somewhere in puberty, meaning that in order to wear a dress without your parents discovering, you'll need your own bedroom and parents who give you some privacy. One typically live with parents until one enters university or joins the workforce, where you'll usually move out of your parent's house to a dorm or rented flat in a different city to finally live truly independently in your own space. This means you'll get the desired freedom to explore your feminine side around the age of 16 - 21.

Singaporean crossdressers however, face a peculiar situation; Singapore's housing situation. Renting your own room doesn't make sense from a financial standpoint, especially since parents usually have space at home and it is so easy to get around our tiny island to university or to work. Even if you do decide to rent, you will likely need to find other friends who are intending to rent (rare, since most people will continue living with their parents), risk the same group of friends discovering that you like crossdressing, as well as come up with a good excuse to explain to your parents why you no longer want to stay with them

Affordable housing in the form of HDB flats built by the Government are only available if you are married, which for the confused, fledging crossdresser is a catch-22 situation. Here is a crossdresser who is uncertain of his inclinations due to the inability to dress up and explore his sexuality/gender identity, yet in order to do so, he needs to find a girl who is willing to accept his crossdressing tendencies and marry him. This would seem like an insurmountable challenge. The typical scenario would be to keep the crossdressing inclinations a secret before and after marriage, keeping the stash somewhere unlikely to be discovered like the army duffel bag or in the car boot, occasionally letting the inner woman out to play. Once again, the crossdresser is back in a cage, except this time it is one of his own making. 

The other option left would be to purchase a HDB flat as a single. However, restrictions put in place by the Government means that the Singaporean crossdresser can only do so when he turns 35 years old! By then, the golden years of dressing up and exploring would have passed. Woe is the Singapore crossdresser who wants a home to call his/her own.   

It is no wonder that many Singaporean crossdressers are still deep in the closet, squeezing in secret dress up sessions when their parents are out of town, but unable to properly practice with makeup and letting their inner woman reach her fullest potential. Most also seem to be able to dress in public only in their mid-20s to 30s, which is around the time where their earning power goes up and they can book hotel rooms to do staycations in. Unfortunately, hotel stays are expensive and not something you can do regularly without causing a big dent in your bank account.

An alternative that some crossdressers go for are storage facilities. These can range from a small un-airconditioned store room, to a full fledged air-conditioned storage space with enough space to put tables, chairs and even a bed. Of course, the latter comes with a premium. Such storage facilities are cheaper than renting a HDB room or flat and comes with privacy too, albeit tending to be in slightly less accessible locations. 

I'm not very familiar with the storage options out there in Singapore so I cannot make recommendations. But fret not! Francesca, a local crossdressing blogger wrote 3 separate posts about the topic which I think will be very useful for crossdressers looking for a decent storage space to keep your growing stash of female clothes and having a place to dress up without worrying about parents, spouse or siblings stumbling upon your female self. You can find out more about Francesca's experience in renting storage units, as well as commercial units (part 1 and part 2).