Musings of a Singaporean Transgender

In the daily grind, the brain regularly wonders how to get more sources of income. Other than buying the occasional lottery ticket and hoping for a moonshot, a common advice flung around ad nauseum is to monetise your hobby. There's good reasons for this advice. After all, if you love to do something and it is supposedly your "passion", isn't it great if you could make money from it at the same time? Then your job will no longer be a job.

Of course things are a lot more complicated than that. If everyone could simply convert their hobbies into their regular and constant stream of income, we'll be seeing people do it left right and center. Not all hobbies have money generating potential, let alone be something that can earn you more than what the day job provides. Most will require a significantly high level of skill in order to generate decent returns (e.g. just because I enjoy football does not make me an English Premiere League level player).

It could be considered a bit sad, but when I am asked what is my hobby, I usually struggle to answer the question. I wouldn't consider crossdressing a hobby per say (it is a part of me), but I obsess about it a fair bit, I don't tire from doing it repeatedly and derive a lot of joy in doing it, which kind of makes it sound like a hobby. I've been asked more than once about monetising it, but I knew the the pressure to generate sellable products/services/content would lessen the enjoyment I derive from crossdressing. The only idea that I more seriously considered was monetising this blog via advertisements. Unfortunately after a 2 month wait following my application with Google Ads, Google decided my blog was of low quality content without bothering to provide any explanation why it was classified as such 😑. But oh well, it was worth the shot.

So if I really wanted to monetise my crossdressing "hobby", what were the possible avenues I could take it?

Storage service

Providing a storage service is a feasible business, although one that has very limited growth potential, since the local crossdressing community is really small. The amount of money one can potentially get from leasing out a room is also limited by the amount of free space one has. In addition, people renting my space would know where I live, which is something I couldn't come to terms with. There's probably better storage options out there.

Makeup / dress-up service

If I significantly improved my makeup skills, this could be a potential side business, although I'd likely have to undercut a lot of the existing makeup artists out there. It is an immensely competitive industry with low barriers to entry, and anyone with a bit of patience and willingness to pick up makeup won't want to seek out a makeup artist unless they're planning for a special shoot. When they do plan for a special photo-taking session, they'll want someone really skilled. There are amateur crossdressers who would be willing to meet a fellow crossdresser, and learn how to elevate their makeup skills in a safe space, but they also tend to be younger with lesser disposable income. Younger crossdressers are also a lot more daring nowadays, willing to come out to friends who could teach them makeup and provide the safe space to dress up, meaning that there isn't a strong need to engage special services to teach them how to transform into a woman.

Youtube / streaming

Youtube and streaming platforms like Twitch, Bigo, etc, are probably a feasible source of side income. The internet allows the potential to reach a huge global audience beyond Singapore. With consistent, quality content pushed out regularly, it is possible to The scene is however, immensely crowded with everyone essentially shouting for attention (figuratively speaking). Another downside would be the need to put myself in the public domain, where everyone can see and hear me. With enough videos/streams out there, I think it wouldn't be too difficult to put two and two together to figure out who my male self is. Maybe at some point when I'm ready to come out I could do it. Or maybe not. I think my transformation from the male self to Isabelle is quite drastic, so it could make for a couple of interesting videos, but that is probably about it.

Patreon / Kofi / OnlyFans

Patreon and Kofi are possible platforms if I ever decide to go down the route of cosplaying, taking superb photos and effectively selling them on an online platform. I've improved in my photography and posing skills quite a lot, but to do it as a professional cosplayer feels like next level stuff. Anyway I don't think I'm pretty enough to have hordes of fans wanting to buy my photos.

As for selling NSFW photos/videos via OnlyFans, well this is something I'd never do (it is also illegal in Singapore if there is nudity, per the Titus Low case). But it seems to be a popular option among many many crossdressers to either fund their hobby or to *ahem* release their inner wild woman. I think crossdressing is a sexually charged activity for many in the community and wanting to monetise this is a win-win option in a sense. But whatever is uploaded onto the internet stays there forever, so got to be careful when one decides to supplement income via OnlyFans.

(So many long sexy legs in this OnlyFans photo 😆)

I'm sure there are more creative ways out there to make money from crossdressing beyond what I listed down above. There are many super successful folk out there (beauty bloggers who sell cosmetics especially), but the market for crossdressing services remain generally small and niche. Maybe if you do think of something interesting, add it in the comments so I can expand this article!

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.

(Not me nor fellow friends, but I'll get here someday)

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.

1. Easy to walk around - Big clothing chains

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.

2. Personalised service - Small brick and mortar shops

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).

3. Free returns - Zalora, Asos

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).

Besides free returns, the next best thing is that you can deliver and return your parcels all via POPStations, which means you can make your purchases without worrying that your mother might "accidentally" discover her son buying women's clothing. Neither Zalora or Asos state the contents on the outside of the package, meaning that you can choose to deliver to your house without too much worry.

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.

4. Local online shops - Carrislabelle, MGPlabel, Topazette, etc

I don't really buy from such shops as they usually charge a delivery fee for smaller orders and do not have free returns (yes, I go for value and buying something that doesn't fit properly or look good irks me significantly). However, the upside of local online shops is that they tend to fit the asian physique better (read: short). They could also be of decent value, as local shops tend to sell clothes in the price range of $30 - $50 for something that feels a bit better quality than some outfits sold in Zara (this depends on the brand too of course). I consider Love, Bonito to be in this category as they used to be an online only shop, though they have recently expanded aggressively into major shopping malls. I absolutely adore Love, Bonito's clothes as the material is heftier and feels high quality. I have also bought a white mesh dress from Carrislabelle, which turned out to be one of my favourite outfits because of how well it fits and they way it hugs the body. It was also a lined dress with material that felt more premium than what I would have normally got at that price point.

(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.

5. Anything you can think of - Taobao, Lazada, Shopee, Shien

Taobao, Lazada and Shopee really brings the world to your doorstep. Anything that you can think of, they sell. Especially so for Taobao. Lolita dresses, cosplays, wigs, accessories, props, wedding gowns, school girl outfits, cheongsams, maid outfits (long victorian, cosplay, or even skanky ones), are all sold on these platforms. Large sized Louboutin stiletto knock-offs? No problem.

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.

(Photo of $27 sequin maxi dress sold on Shein. Looks fantastic, but I have my doubts on the quality. The model looks so glam, it looks like it may have been from a prom dress shop selling $100+ dresses. On Asos this would be $60 or higher, especially if the dress was lined)

6. Online 2nd hand - Carousell

Buying 2nd hand is recommended for crossdressers, considering how infrequent we wear our female attire. Carousell is a one stop portal that allows us to search for and buy 2nd hand women's clothes easily on our mobile phones. If you're afraid to meet up with the seller in person and reveal that you are a guy, you could easily arrange for the item to be sent via mail for a couple of dollars. This makes shopping via this app a very feasible option for crossdressers still in the closet.

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.

7. Cheap 2nd hand - Refash

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.

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).

Fetish: a form of sexual desire in which gratification is linked to an abnormal degree to a particular object, item of clothing, part of the body, etc.

Based on the definition provided by Google, I don't think it's too far off the mark to say that yes, crossdressing is a fetish for many in the community, whether they like to admit it or not. For many, wearing pieces of female clothing usually results in sexual arousal. I'll be lying if I said that dressing up in female attire doesn't get my engine revving as well. It is also one of the reasons why I think the urge to crossdress increases exponentially after the onset of puberty, when sexual desires emerge due to the new chemical cocktails swirling in the body. The desire to "get off" while crossdressed starts around that age too.

I'm not saying that crossdressing is a fetish for everyone in the community. There are many reasons why one decides to crossdress and not all of them have their roots in deriving sexual pleasure. Some do it because it is fun, some do it to to feel whole and complete, etc. Our motivations to crossdress may also change as we grow older and more experienced as well; it could start off as a sexually stimulating activity, but the fires mellow over time and one crossdresses because it is a relaxing, fun activity to do. Shopping as a girl is undeniably more enjoyable by MILES compared to shopping as a guy.

For crossdressers, it is important to realise that there is nothing wrong to feel turned on by wearing women's clothes (there is sometimes a lot of post-dress-up / post-release guilt involved). Just because something is a fetish does not mean that it is a perversion. These two words have a tendency to be confused together. As humans, we all have our different personal tastes and kinks. For a more mainstream example, guys like it when ladies with long legs show off their figure in short, tight bodycon dresses and high heels. Isn't that a fetish too? But it is never considered a perversion to have this preference (unless you're living in a super conservative part of the world, which in Singapore, we are not).

Perhaps in the definition above, "abnormal degree" is the part that we crossdressers need to be conscious of. It differentiates a healthy kink from an addiction that consumes your everyday thoughts, to the point of affecting your ability to function properly day to day as another member of society.

There's nothing wrong if crossdressing turns you on. But always remember, everything in moderation 😉

If you asked me before 2019 whether I would dare to step out in public it would have been a flat out no. And if you retorted to say that not only would I dress up in public multiple times, I would also participate in an interview as Isabelle for a video that would be shared on multiple social media platforms, I would say that you were insane (and probably stopped talking to you).

Oh how wrong pre-2019 Isabelle was.

As horrible as 2021 has been as the 2nd year of Covid-19, Isabelle marked off two amazing things that I never thought she was ever going to do; doing a bridal photoshoot in January and ending off the year with an interview.

(The only photo I snapped on the day of the interview)

The local media network Must Share News (under the parent company The Smart Local), sent out DMs via social media to a number of crossdressers in the community for their "Ask me anything" video series. Who would have thought crossdressers specifically would be of interest. After all, the stories and struggles of transgender folk who daringly transition are more interesting, and crossdressers tend to be very closeted. There is only one video from a local crossdresser's perspective that I know of, which is this piece on crossplayers here by Channel News Asia.

When I received the email from MSNews, I was wondering if it was real. But the email was written too formally to be fake and after a bit of digging around I verified that it was a legitimate request for an interview. The question now was, should I agree to be interviewed? It would be a fun experience to be interviewed as Isabelle. I could share my views and experiences to shed a bit of light on the very closeted community. But agreeing to the interview increased the risk of being recognised tremendously. The risk-reward calculator had alarms blaring in the background. Unlike my own social media account where I could control who had access to it and what was shared online, this video would be in the public domain. Relatives, friends, co-workers, acquaintances could be watching this video without my knowledge and suddenly realise that it was my guy self under the wig, makeup and dress. The thought of being outed was very very scary, because what was at stake was not only me, but my family as well.

I think there's a large amount of stupidity and YOLO involved here (vanity too, if I'm honest with myself), but I eventually agreed to the interview. I truly hope I don't regret my decision.

The team at MSNews were respectful and very efficient in doing a pre-interview, arranging for the actual shoot and tidying up the drafts and final video, all within a couple of weeks. I suppose in this social media age, speed is very important.

You can watch the video embedded below, or via the links on Youtube here, or Facebook here. For regular readers of my blog, you'll find the content familiar. But video as a medium is a lot more appealing and easily digestible. I see this as a little contribution to the community, to hopefully show society that crossdressing is quite a harmless activity and that the community exists! And many of us are in the closet, hoping to one day stride out into the open without being judged negatively.

Going out in public for the first time is usually one of the biggest hurdles that crossdressers face (the hurdle is really a mental one). When one is still in the closet, dressing out in public is a Herculean task and feels like a mountain that they want to but will never be able to scale. So when it does happen, there is a rush of emotions that is quite unforgettable.

This post took longer than I expected to write, as it took some time to find sisters who were willing to share their stories, and pen them down in a way to capture what they wore, their motivations and how they felt. If you're just starting out on your crossdressing journey, I hope this short collection of experiences inspires you to take that tiny step out of the door. Because one thing is for sure; none of these fellow sisters regret stepping out enfemme. The biggest hurdle that all of them had to over come was the one in the mind.

"My first time in public was in 2013 at an Anime convention in Suntec City Singapore. I cosplayed as Junko Enoshima (main antagonist from the Danganronpa franchise). I had always wanted to attend a convention crossdressed but was always afraid. It was the egging on of friends that finally made me take the plunge. A few of them were also attending the convention crossdressed, so it meant I had some company. I didn't know how to do my own makeup, so I had to meet up with a friend to help me with the make up.

The first step out of the door into the public was incredibly scary. I remember my heart was thumping so hard I could hear my own heartbeat in my ears. It got even worse when I got to the crowded busstop to catch the bus to the Anime convention, with all the aunties and uncles staring at me. I could almost feel their eyes bore into me, making me want to bury my head in the sand and just fade away.

I did succeed in getting to the Anime convention without throwing in the towel. It was one of my first conventions so I explored the venue with my friends. Although everyone was dressed up in their different costumes, I strangely didn't get more comfortable with time and almost wanted to shutdown. Wearing a skirt in public for the first time made me feel super vulnerable, especially from the large number of stares. The experience almost turned me away from cross dressing in public for good (fortunately I didn't. I have since become more thick skinned and learned not to give a f***)

Thinking back about my first time in public makes me want to cringe. Although a few of my friends were also crossdressed, I was clearly looked the worst; my wig was messy, the costume was ill-fitting and I did not even use breastforms. It was a damn nightmare."

- Chiharu (Singaporean)

"My first time in public was in 2019, when I was given the opportunity to spend a month in the US for work. It was one of the rare trips where I was able to be completely alone as my girlfriend didn't want to travel so far with me (said girlfriend also doesn't know about my female self). I planned ahead of time, ordering the wigs, clothes, heels and other female paraphernalia to be delivered to the hotel I would be staying at. The hotel staff were super nice to accept packages on my behalf, as long as I informed in advance.

During my month long trip I crossdressed almost every other day, but it was within the confines of my hotel room as I had still afraid to go out in public. However, in the final week of my US trip, an online conversation with a fellow Singaporean crossdresser made me muster up my courage. She said that one day I will be old and will regret not taking advantage of the opportunity I was given. By that time, it would be too late for me to fully enjoy being female in public. Since I wasn't anyone famous such that blackmail could be a possible problem, why did I need to be afraid of going out?

With my work trip in the US nearing the end, I decided it was now or never. Dressing up in the US, I ran an even lower risk of being recognised on the streets. The next day, I got up at 4am in the morning to prepare. By 5.30am, I was ready to go, dressed in a grey checked shift dress with white collars, black pantyhose, heels and my makeup on. Fear gripped me again just when I was stepping out of the door. It took a lot of breathing and "self-psycho-ing" before I rushed out my hotel room door, down the fire escape and straight into my car. My heart was beating with terror, but I felt a sense of achievement! I finally stepped out in public as a woman for the first time!

My first stop was a nearby CVS (a pharmacy chain in the US). It was pretty empty this early in the morning, so walking around wasn't too stressful. The cashier on duty didn't pay me any attention either when I purchased a few random items. As the morning went on I became more daring and visited a Starbucks, ordering a coffee in my girl voice and drinking it there, enjoying the experience of chilling in a cafe and observing random customers enter the store. The sun was up when I finished my coffee, so I went to a nearby children's playground to enjoy a ride on the swing. The gentle sunshine on my face and the rush of cold morning air past my hoisery covered legs felt glorious.

Eventually, it was time to return to my hotel room. By this time I had built up enough courage to enter the hotel via the front door, walking past the main reception to the lift lobby. Nobody even batted an eyelid. To commemorate my successful first time out in public as a woman, I took a few more photographs before transforming back into my guy self and back to work. Thinking back, I remember feeling how scared I was of stepping out in public. But by questioning and rationalising my emotions, I allayed my fears enough to finally step out in public. It felt super nice that after so long, I finally unlocked the achievement of stepping out in public enfemme. I didn't manage to squeeze another outing again in the US, but after returning to Singapore I began planning more trips in public as my female self."

- Anonymous (Singaporean)

"My first time in public was in May 2018, when I joined a Malaysian and Singaporean crossdressers event in Kuala Lumpur. I had always wanted to go out in public as my female self but never dared to do so. However, in the lead up to the event, many of the other experienced sisters encouraged and egged me to go out in public to enjoy the city as a woman. Starting with baby steps of course. I was lucky to have the experienced and patient Jessica as my "mentor", who gave me advice and gently encouraged me to step out in public.

While in Kuala Lumpur I stayed at the Le-Apple Hotel. It took me a while to choose the outfit for my first time out in public, finally deciding on something simple; a beige cotton tank top, a black cardigan with elbow length sleeves, a knee length skirt with lace details along the edges, a black chin length wig styled with a slight bob and shiny red nail stickers to give my outfit a bit of pizzazz. Not wanting to be too adventurous, I chose to wear black flats instead of heels for my first time out.

But I couldn't take the final step! Although I was all dressed up, I was drowning in my fears and didn't want to even open my hotel room door to step into the corridor...until Jessica (in guy mode) finally came into my room to drag me out. I had a perpetually nervous look on my face, asking Jessica countless number of times "Do I look ok or not?". It was super scary, but I made it into Avenue K (the mall next door). Jessica helped to take some photos in front of the Sephora store while we waited for the Singaporean sisters to arrive. Sticking extra close to Jessica made me feel a bit more secure during the wait. I was pretty sure the security guard noticed me because Jessica and I walked in and out through the main entrance multiple times. Eventually we managed to link up with the Singaporeans for a short stroll in the mall before heading back to the hotel for a rest.

But that didn't mark the end of my adventure in public! I had a dinner event to attend with a whole bunch of other Malaysian and Singaporean sisters. For dinner, I enlisted the help of a makeup artist to doll me up with a smokier night-time look. Outfit wise, I chose a long black sleeved top, a short black skirt with small white polkadots, a choker and a long dark brown wig that was just past my shoulders.

The dinner gathering was in Baan26, a Thai restaurant along Changkat Bukit Bintang. The organisers reserved the entire upper floor, which meant a safe space for all of us to mingle and interact. Before long, around 20+ sisters from various parts of Malaysia (majority from Kuala Lumpur) and Singapore streamed into the restaurant. Everyone was nice and friendly, and I spent so much time taking photos with fellow sisters at the restaurant that I don't think I ate much of my dinner. By the time we had to leave the safe confines of the restaurant and onto the bustling Changkat Bukit Bintang street, I was a lot less afraid to be out in public. The euphoria from the dinner event and having encouraging sisters accompanying me dispelled any nervousness I had.

I didn't get to dress up in public again after the event for some time due to familial responsibilities. But I was super happy that after my long journey as a crossdresser in the closet, I finally fulfilled the dream I had wished for the longest time. Without help from Jessica who literally dragged me out of my shell, this dream would never have materialised. It was an incredible, amazingly enjoyable whirlwind of a day, and I look forward to join another event like this."

- Lily Siow (Malaysian)

"I was in my late 20s when I finally mustered the courage to step out in public as Jessica for the first time, in the Winter of 2018. I always wanted to go out in public as a woman, to be seen as presenting as female. It was a strong desire from within to be validated. Back then, discord groups hadn't existed and the reddit sub on crossdressing was in its infancy, so I wasn't egged on to go out in public since my interactions with other crossdressers were minimal.

For my first time out, I wore a black hoodie, a black skirt, nude hoisery and my usual pointed heeled pumps. I intentionally chose to visit a park for a short stroll at night as it was a lot less crowded (and therefore, a lot less scary). Even then, the first step out into the open took a fair amount of self-convincing. I remember clearly sitting in my car for what felt like eternity, not wanting to open the door to make that first step. But when I finally did, boy was it exhilarating! I don't deny that I was still scared as heck, but my first day in public as Jessica was also the day I kind of realised that nobody really cares that you are crossdressed. There were a few passers but I didn't interact at all with any of them. Everyone was absorbed with their own lives and personal activities. After I was done with my stroll in the park, I also grabbed some cash from an ATM and attempted to find a mirror to take a photograph in (though I failed to find one).

Looking back though, my outfit was super cringey. I looked like crap, my wig was a wreck, my makeup was barely there and my looks wasn't great for going anywhere (the whole look even looks like garbage in the few photographs I took). But we all have to start somewhere. This event was the beginning of my adventures as Jessica in public, and in spite of my amateurish dressing, I'm glad I took the plunge and opened the door to expressing my feminine side."

- Jessica aka Microsoft Excel 2007 (Canadian)

"The first time I went out in public crossdressed was in the Spring of 2015 at one of the biannual conventions in my city (Manga and anime is HUGE in France, so conventions are quite common). I wanted to cosplay as a male character with a prop gun, but due to the terrorist attack that occurred just a few months before, all gun-like props were banned at the convention. I thought it was a good excuse to make a Lolita costume, so I bought a pink fabric with cupcakes designs and followed a Youtube tutorial by Yumi King to make my dress (which turned out surprisingly decent). I got my shoes and wigs from Bodyline (a low budget lolita/cosplay brand), pantyhose from Calzedonia and a petticoat from a 50s shops.

The lead up to the convention was really scary, as I was worried what others might have thought about me. But I soldiered on and decided to attend the convention crossdressed anyway. Opinions be damned! The first day of the convention had a focus on Lolita, which was a nice coincidence. I remember admiring and envying other cis-girls in their proper Lolita dresses. I was lucky enough to be asked by one of the girls if I was keen on trying on some of their outfits at one of the booths in the convention. There was no way I was going to pass up that opportunity.

I arrived early on the second day of the convention to visit the booth. Of the many pretty dresses, I picked out a beautiful blue one piece from the specialty brand "Baby The Stars Shine Bright" (BTSSB) to try on. My makeup was done by a fellow Lolita (who also happened to be a guy). The BTSSB dress was nearly impossible to get out of alone and I felt so incredibly pretty in it, which to be honest got me a bit turned on. All the newly christened Lolitas had to get their photos taken and I was no exception.

Sometime after the convention while browsing the local community site, I chanced upon a video of me in my DIY Lolita dress, telling another girl that I was a Lolita. Seeing myself on camera with my confidence in spite of my beginner level dressing was a super cringey moment. But I was glad I went for the convention anyway, which allowed me to discover more about myself, the Lolita world and meet girls in the local community."

- Claire (French)

Having chatted with multiple crossdressers in the past few years, I observe many parallels in their stories. Despite different backgrounds, ethnicities, nationality and upbringing, the majority of male crossdressers seem to have a similar starting point and go through the same phases. Age does not dictate which phase one is in, but it does have a big influence on whether one moves on to the next phase or not, due to financial independence, personal independence, or just an increasing sense of YOLO.

(Disclaimer: the following phases isn't based on research, but my opinions based on observations)

1) Initial Realisation

The first phase usually starts off young, around 7 to 12 years of age. Just like a switch is turned on, inexplicably strong feelings of desire and curiosity of hoisery, skirts, dresses and other feminine garments manifests itself. There's also a lot of confusion at this phase, since the newfound desires run contrary to society's programming of behaviour expected of males and females. Strangely, this phase seems to happens just before the onset of puberty and the awakening of sexual desire, which many of us find so intertwined with ladies' clothing.

For a minority, the realisation phase happens in the late teens / early 20s, usually triggered after a single crossdressing event (during halloween, due to a dare, etc), which helped to provide the first taste of how nice ladies clothes feel.

2) Closeted - Borrowing clothes

This second phase occurs almost in quick succession after the discovery phase. Because the crossdresser is usually a young child or teenager living with his parents, the only access to ladies' clothes will be those of his mother, sister or relative. Being in school also means very little spare funds to purchase his own clothes and wig, let alone makeup, lingerie and heels. However, because the crossdresser is so early in his journey, it doesn't take much to fulfil his desires to look like a woman. Just slipping on a silky chemise, a tight pencil skirt or feeling the tight constrains of a bra that's usually too small for his male chest is enough to get his motor going. The mind and imagination usually fills in the gaps that makes the crossdresser feel incredibly pretty.

At this early phase of his crossdressing journey, it can be a very confusing period. He knows that crossdressing isn't normal, perhaps even wrong as society has ingrained in him. Men and boys shouldn't be wanting to wear dresses and wanting to feel....pretty. Yet strangely it feels so damn good and he cannot help himself. When there is a window of opportunity for him to crossdress coming up, he will obsess in the lead up to it. Usually, there is a constantly recurring feeling of guilt, as he struggles between his personal wants and what he thinks society requires.

3) Closeted - Owning clothes / tried makeup

Unless there's a fashionista in the house, borrowing clothes from either mum or an elder sister gets old really quickly. Mum's tend to have a more mature style, while sisters probably have a smaller frame and thus harder to fit once puberty hits. I remember not liking ANY of my mum's clothes, and not being able to properly zip up my sister's dresses (except the stretchy ones). Also, borrowing clothes raises the risk of being found out, in case of accidental ripping of favourite outfits, forgetting to put them back to the exact location, or *ahem* having accidental biological release due to extreme excitement. Mothers are especially attuned to things that are out of place. So it is only a matter of time before crossdresser move to phase 3 - owning a feminine wardrobe. After all, you cannot keep trying on your sister/mother's favourite outfits or lingerie.

Nowadays, online shopping and delivery to pick up stations makes it very much easier to buy clothes and pick them up without even needing to speak to any person. All you need is a debit or credit card. Once a crossdresser has his own outfits, he will also take the effort to purchase essential accessories to complement his feminine look, such as wigs, breastforms, high heel shoes, hoisery, etc.

Crossdressers also begin dabbling in makeup after a while, as it is the next essential piece in trying to look pretty and convincingly female. It is potentially challenging though, as makeup is time consuming to apply and remove. Given that most Singaporeans live with their parents until they are married, they almost never have a truly private space to try on makeup at home. One can easily swap from female to male attire very quickly, but to remove a full face of makeup cleanly will take a lot longer. As such, being good in makeup can sometimes take a while.

I find that phase 3 usually lasts very long, because the mental hurdle that needs to be overcome in order to step out in public as a girl is very high. For some crossdressers, the fear holds them back and they never gets to phase 4 and 5, instead skipping on to the normalisation phase (phase 6). Some slightly more daring crossdressers do come out to their wife/girlfriend/friends, but they still do not go out in public as a woman. For these, they are also considered to be in phase 3.

4) First Time Out

Going out in public for the first time is very scary, but incredibly exhilarating. The chemical cocktail due to the fear of being discovered, guilt of doing the taboo, and desire to go out as a female, is a powerful, heady mixture. I still remember vividly the first time I stepped out in public how I could feel the thumping of my heart in my ears.

For many in Singapore, the first step out in public seems to often be in the dead of night when the risk of being seen by others is very low. Another common venue for a first time out would be to one of the LGBT clubs in Singapore, either alone or egged on by other more experienced sisters. For those who are bolder, it could be a trip to the park or shopping mall in the day, the latter being based on the logic that it's easier to blend in with so many people walking around, since people are mostly too busy (read: self-absorbed) doing their own things that they don't really bother paying attention to others. Going out in public for the first time usually marks the crossing of the threshold into a new phase of discovery of the crossdresser's journey.

5) Discovery

With going out in public as a woman no longer in the realm of fantasy, the flood gates are now wide open, showing a whole range of possibilities and new activities to try out. There's will be many firsts from here on out, such as shopping in girl mode for the first time, dining in a restaurant for the first time, taking that selfie in the ladies toilet for the first time, watching a movie as your feminine self for the first time, being addressed as "miss" for the first time, spending a few days in girl mode whilst overseas...the list goes on.

For the sexually adventurous, it could be the discovery of new sexual preferences, through meeting like-minded people in the community or just due to a greater willingness to reach out and try. Perhaps one also discovers how incredible sex may feel when you are dressed as a woman, be it with your girlfriend, wife, other crossdressers or even men.

Personally, I think this discovery phase is the best phase of crossdressing. The simplest activities that we take for granted in male mode are now wonderous and exciting as a female. Although some of the experiences are viewed through rose-tinted glasses (e.g. thinking that every outfit looks extra pretty when trying out clothes in the fitting room for the first time), because everything is new and exciting, these make for great memories that we will reminisce when we are further along in our crossdressing journey.

The younger one reaches the discovery stage the better, as crossdressing is more fun with youth on your side. Also, discovering your own sexual orientation and whether you plan to transition early is helpful in avoiding future regrets in life. Based on personal observation, crossdressers do seem to be reaching this phase earlier, due to the proliferation of smartphones, online shopping and access to easily available information about crossdressing via the internet.

6) Normalisation / Plateau

After having tried most of the common activities that crossdressers tend to do, one reaches a normalisation phase. It's frequently described as a "been there, done that" phase, where the novelty of crossdressing has waned. This is just like any hobby / activity really. Take for example travelling. Your first few holidays overseas would be incredibly exciting, but after your 50th holiday, cities and natural sceneries start to look the same. It takes a really epic destination or unique activity to get you excited again.

Similarly, crossdressing can still be exciting, but it takes a really pretty outfit or a new, novel activity to trigger the same desire that one used to feel in the discovery phase. When all it took in the past was sliding on a pair of stockings up one's legs to get the motor revving, it now requires dehairing, a full-faced makeup, immaculate hairdo, a perfectly coordinated outfit with matching lingerie, and perhaps an annual themed crossdresser gathering to get one equally excited again.

Frequency of crossdressing usually drops in this phase, due to the reduced interest in crossdressing, or that it simply takes a lot of effort. If the excitement derived isn't consummerate with the effort put in, why would you do so? A common reply to invitations to dress up might be "I'm too lazy to dress", when the you 5 years ago would have pounced on the same opportunity in a heartbeat.

7a) Retirement

Sadly, the fires of excitement that burned so brightly in the past will fade away with time, either due to age, fatigue from crossdressing or a lack of novelty. Once everything in his crossdressing to-do-list has been checked off multiple times, he may decide to hang up his stilettos, little black dresses and retire for good.

Another type of retirement that is commonly observed is early retirement (usually after a bout of purging), brought about by personal reasons (birth of a child, wife demands swearing off crossdressing for good, etc), or guilt of living a double life and not being a "proper" man. However early retirement tends to be temporary, with the hiatus lasting from a few months to a several years, until a trigger event happens that plunges the crossdresser back into the thick of his feminine ways.

7b) Full time girl mode / Transition

For some crossdressers however, dressing as a woman reaches an inflection point; he realises that his gender dysphoria is so strong that the infrequent crossdressing isn't sufficient to meet his personal needs. He is transgender and wants to spend his time living as a woman permanently. Whether he undergoes hormone replacement therapy, feminisation surgery or SRS, this threshold is the largest one to cross, as he isn't a crossdresser anymore; she's now a woman. It is very challenging, as it requires her secret to be made known to relatives, friends and society. But despite its challenges, there are success stories of crossdressers who eventually live full time as women.

Conclusion

For readers who have been following my blog posts and reading about my crossdressing journey, you probably can point out easily that I am currently in phase 6: normalisation. Crossdressing is still exciting, especially if I get to try a new outfit that I have been pining for the longest time that makes me look extra pretty.

So dear reader, which phase of crossdressing are you at? Do you agree with my observations and rough mapping out of phases which mtf crossdressers go through? Do let me know if there are phases or key details I may have missed out, so that I can expand this article.

Musings of a Singaporean Transgender

About Me

Pages

Popular Posts

Tags

Archive

Contact Isabelle

Total Visitors