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Musings of a Singaporean Transgender


I decided there was a need to write about this topic after a friend shared her unpleasant experience with another sister within the local crossdressing community. It wasn't the first time I've heard about what I would consider "unacceptable behaviour" by another sister. 

Crossdressing is a very niche interest and the community is tiny. Many of us take great solace in the social aspect of dressing up together, creating a safe space where one can let loose, be themselves and trust each other with our deep, dark secret that our closest relatives and friends do not know about. However, there are actions I consider to be unacceptable behaviour as a member of this small community. At its most harmless, it is an annoyance to the victim. At its worst, these unacceptable behaviours are borderline criminal.  

I will not cover illegal activities, such as stealing of women's clothes, attempting to take upskirt or partially undressed photos of other women in toilets. Such cases, which we read in the news far too often, are obviously criminal and will be dealt with swiftly by the law once found out. 


1) Non-consensual touching

The friend of mine shared that she was on the receiving end of non-consensual touching by another crossdresser, during a dress-up gathering in a hotel room (due to the inability to crossdress at home, it is common for hotel rooms to be booked by one or more sisters for a dress-up session / gathering). The incident occurred unexpectedly when she was alone in the room with the other sister, taking her by surprise as she had thought she was in a safe space. In her state of shock, she did not pack up and leave immediately. She was touched / grabbed inappropriately a few more times despite her protests, before she finally snapped out of her shock and made the decision to leave.

Although we are biologically male under the dress, padding and makeup, when we crossdress, we shed our male self and take on a female persona. Our movements are less harsh, our mannerisms more gentle. We feel female not just physically but mentally, but it means we can also feel more vulnerable.

It is undeniable that crossdressing is a sexually exciting activity for many in the community. For this majority, slipping on hoisery, zipping yourself into a mini-dress and strutting around in high heels usually has the potential to get one's engine going.  If the goal of a gathering is to crossdress together and partake in sexual activity (be it just touching or full blown sex), as long as it is between consenting adults, it is perfectly acceptable, and crossdressing together could be a fun, sexually charged experience. The problem arises when the touching is non-consensual, thereby pushing it into the realm of sexual harassment.

Having a common hobby is no excuse to touch another sister without obtaining consent. Neither is the fact that crossdressers have a tendency to wear outfits bordering on skankiness, drawing inspiration from the sexually-inclined male mind and the need to be over-compensate using hyper-feminine clothes, with the laciest lingerie, shortest mini-skirts and sky high stilettos. As is the case for women, don't blame the perpetrator's lack of self control on the victim's style of dressing. In fact, there is no excuse at all to touch someone else inappropriately without their consent.

My suspicion is that some of these sisters know very well that for many in the community, crossdressing usually has its roots in sexual arousal. By luring young / new crossdressers with the prospect of a safe space and care from a fellow sister, they can create an opportunity to touch the youngling, in hope that this physical contact could, tempt the trusting newbie to partake in sexual activity in the moment of headiness. One could argue that such actions is part of the chase, or part of helping another sister get over her self-denial and break out of her shell. Any sexual fun that results is between consenting adults. But what if the person being touched doesn't want to be (and yet is repeatedly touched)? Or does something she regrets? 

Let's put it this way. If a guy inappropriately grabs or touches a lady he does not know, or even a female friend without first obtaining consent, it is considered molest and a criminal offence (I'm no lawyer, but that's my layman understanding of things). Unfortunately, the fact that [1] crossdressers are basically all guys,  [2] non-consensual touching incidents between crossdressers tend to take place in hotel rooms or in clubs/bars, and [3] the secrecy surrounding this taboo activity we partake in makes it difficult for the "victim" to come out to anyone or make a police report (in severe cases). 


2) Stealing photos

This behaviour baffles me. Why would you steal another fellow crossdresser's photograph and pass it off as your own? One reason I can think of this "identity theft" is to catfish admirers on social media such that they can enjoy the attention, praise, get off on sex-texting, or perhaps try to obtain gifts in the process. 

There is one notorious crossdresser in the local community who has edited her face onto other crossdresser's photographs and posts the edited version on social media, claiming the photo to be of her. Like...why?! I know apps can do a face swap, to see how one might look with a body of a K-pop star, or wearing an ancient chinese princess outfit for the fun of it. But using other's photos and passing them off as yourself seems to take it to another level 😐

I suppose one can argue that this is the risk of social media. The moment it is shared on the internet, even if the account is private, there is a chance of your photos being downloaded and sent around. So if you share it with someone or on social media, you need to be ready for it to be shared in the public domain.


3) Outing someone

This is one of the worst crimes a crossdresser can inflict upon another. Maintaining privacy is a high priority among many in the community, and for good reason. Male to female crossdressing is not widely accepted in society. As much as society is slowly becoming "woke" and "liberal", the reality is that Singapore's society (family, school, workplace) in general still isn't very accepting of mtf crossdressers. More often than not, we are viewed as weird, unnatural, or worse - perverts.

Leaking out of a crossdresser's identity to family members, friends or colleagues can be potentially very damaging. Just like squeezing toothpaste out of the tube, there is no way to "unsqueeze" the toothpaste; the secret is revealed and damage is done. There is no way to justify such behaviour, even if the reveal was done accidentally (how can one be so careless with other's secrets?). If it was done intentionally, then whoever did so had malicious intent and needs to be branded a pariah in the crossdressing community. 


Wrapping Up

One could argue that what I described above as "unacceptable behaviour" is merely my opinion, and I should get off my moral high horse. Who am I to be the judge of what is acceptable or not in the crossdressing community? I suppose that could be true; I sometimes do sound like a goody-two-shoes. But in my book, these behaviours I described are red lines that I don't think should be crossed. For newly minted sisters just opening their own closet door and reaching out to others in the community, these are some behaviours to be wary of.

Short answer: No, wanting to crossdress doesn't mean that you are gay. But you could be (and that is independent of your love for crossdressing).

I presume the definition of "gay" here is being sexually attracted to other men.  There is quite a fair bit of fear among crossdressers that deep down, they are gay. This is likely due to how we have been brought up in society to shun that which is deemed not "normal". 

For most of the crossdressers that I know, they generally view themselves as straight. They find no sexual attraction to the male form, and are turned on by women. However, the confusion arises when the crossdresser is attracted only to women when wearing men's clothes, but when crossdressed, he has adopted his female persona and is willing to participate / turned on by sexual activities with other men. Or perhaps the crossdresser finds other crossdressers a turn on, regardless of the genitalia (sometimes especially because of genitalia). Throw into the mix the recurring question of whether to transition or not, and you've got yourself a really confusing state of affairs. 

I wrote a short post about the difference between "Gender Identity" and "Sexual Orientation", which are usually mixed up, and for good reason. These are non-binary, resulting in so many permutations (a sample list shown below). Our emotions and how society expects us to behave also tends to cloud our evaluation and cause us to conflate the two. 
  • Male ❤ Female = Heterosexual
  • Male ❤ Male = Gay
  • Crossdressed Male ❤ Female = Heterosexual? Or Lesbian?
  • Crossdressed Male ❤ Male = Gay? Or Heterosexual?
  • Crossdressed Male ❤ Crossdressed Male = Gay? Lesbian? Or Heterosexual?
  • Crossdressed Male ❤ Transwoman* = Heterosexual? 
(*To make it clear. Transwomen ARE women.)

My personal take is that you are likely to be bisexual if you are normally attracted to women, but are also willing to participate in sexual activities with men when crossdressed. Regardless, you shouldn't beat yourself up internally if you swing that way. Sexual tastes and preferences, as long as they aren't harmful to other people, should be more accepted (barring the truly bizarre ones...like *ahem* necrophilia). The good news about living in Singapore in this day and age, is that we can freely participate with members of the same sex  (I won't go into the whole issue about gay sex being illegal in Singapore, due to a very archaic law from the colonial days that has yet to be repealed. That subject is very incendiary and there's a whole range of polarising views on the matter).

I'm not an expert on the topic, so do take what I write here with a pinch of salt. There are articles on this question which you can find on google, such as here and here. Reading more might give you a bit more clarity on the matter. I do find that this site called the Genderbread Person on the differences between "Gender Identity" and "Sexual Orientation" is much more illustrative and may help you pinpoint where you call on the spectrum for sexual orientation.

No, no, no, no! You should never purge! 

Purging is usually a dramatic move, done in an attempt to stop/quit/swear off crossdressing. But as painful as the purging process is, it is ineffective in staving off the desire to crossdress. Personally, I think the desire to crossdress will never go away. It could be suppressed or fade with time, but it will still be there. Purging your female stuff is actually the easy part. The difficult part is being able to stay away from crossdressing completely, day after day. You may be able to suppress the desire, bottling up you emotions and urges for weeks, months, even years. But all it takes is a trigger and your crossdressing will come back with a vengeance. It is made even worse if you promised your partner or parents that your crossdressing days are over. Because you become stuck in a trap of your own making. Your partner / parents will be relieved to hear that you have stopped your "deviant" behaviour, but in your attempt to please them, you will feel even more guilty when you eventually fail to keep to your promise and dress being their back again. 

If you don't believe me, just do a quick google and you'll find many accounts of crossdressers purging for various reasons, only to end up rebuilding their female wardrobe again. And the cycle repeats. 

Further more, crossdressing isn't exactly cheap (unless you're fine with putting on a simple dress and wig). How much money did you spend to built up that collection of undergarments, dresses, blouses, skirts, heels, makeup, padding, wigs, etc? When that desire returns in a few months time, how much more are you going to spend rebuilding your wardrobe? Unless you've lots of spare cash, tearing down and rebuilding your wardrobe really isn't the best way to spend your hard earned money.

Hold your intent to purge. Instead, spend some time to reflect on the true underlying reasons for your guilt and possible solutions. Perhaps there is a need to take a course of action (e.g. coming out, or finding a special someone who accepts you, or rent a storage somewhere) that could allow you to indulge in your peculiar but harmless hobby.
(Image from the Genderbread Person)

They are all different! And it is important to know the difference, because people don't neatly fall into a binary. Even for biological sex, which for a majority of situations are a binary, there are occasions where people are born intersex and end up in the middle of the spectrum.

This is a complicated topic and I am definitely no expert. But I did chance upon a good site, with a very simple illustration that explains this the difference between "Gender Identity", "Gender Expression", "Biological Sex" and "Sexual Orientation" very clearly, called the Genderbread Person. I won't attempt to rephrase what the 4 components means, you can read about it more on their website.

But let's try to run through two examples to illustrate. Do forgive me if I didn't capture this correctly 😅 For the typical heterosexual male, it will be as follows:
  • Gender Identity - "I identify as a Man"
  • Gender Expression - "I wear masculine attire and behave as a man would"
  • Biological Sex - "I am born Male"
  • Sexual Orientation - "I am Heterosexual. I am turned on by women."
For me, I suppose it is as follows:
  • Gender Identity - "I identify as Genderqueer. On most days I am a Man, but I also identify as a Woman on other days"
  • Gender Expression - "I wear masculine attire and behave as a man would, but I am also very feminine and love to show my female side to the world. I am not androgynous"
  • Biological Sex - "I am born Male"
  • Sexual Orientation - "I am Heterosexual. I am turned on by women."

It is totally understandable why people get confused with the terms. They just seem so similar! It gets even more confusing if we ask questions like "Am I heterosexual or homosexual, if I like (1) mtf crossdressers or (2) other men, but only when I'm dressed as a woman?". Personally, for (1) I think you are heterosexual since I view mtf crossdressers as women. For (2) you are heterosexual. However, it is likely that you are also attracted to women or other crossdressers in male mode, so by extension you are bisexual.

It is all rather confusing, I must admit. I am probably not entirely correct in my assessment above. If we in the LGBTQ community already get confused about the terms, those who are outside of the community will find it even harder to wrap their heads around this. It is also very easy for them to pigeonhole us into a binary, as general society has done. So we do need to be a bit forgiving if people don't fully understand the differences. However, the main message should be that Gender Identity, Expression, and Sexuality isn't binary, but a spectrum. And we shouldn't beat ourselves up for who we just because we don't fall neatly into the either ends.

Gender Dysphoria definitions:

Merriam webster: "a distressed state arising from conflict between a person's gender identity and the sex the person has or was identified as having at birth"

Cambridge: "the unhappy feeling that some people have when they feel that their identity (= who they are) as a man or a woman does not fit with the sex that they had, or were said to have, at birth"


Although the definitions of gender dysphoria are quite similar, I find the Cambridge definition better, as "distressed" is too severe a word to use to generalise the experiences of all who experience gender dysphoria. 

Regardless of where you are on the transgender spectrum, I believe that we crossdressers struggle with gender dysphoria to varying extents. We may not detest our male body parts as strongly as some transwomen do, but there are elements of envy. It boils down to the desire to look not only female, but also  beautiful. The inability to do so convincingly, regularly or reconcile reality with expectations in the mind (possibly unrealistic) manifests in feelings of unhappiness or discontent. For me, these feelings are usually non-existent or mild. But every now and then, they bubble up to the surface and burst forth like an erupting geyser. It is usually triggered when I get stressed and want to run away from reality. Stressors include:
  • Work (e.g. so many deadlines, my work is stupid. Why can't I be a pretty model and earn big bucks just by looking pretty)
  • Shortfalls in real life (e.g. My peers are more successful than me. Why is financial freedom so far away)
  • Seeing beautiful women on the street or on social media (e.g. how is it that ALL these women look so effortlessly beautiful and I cannot be like them. Why is it that with my best efforts I only achieve a fraction of their beauty/femininity)
  • Seeing other CDs who are effortlessly feminine (e.g. why are they born so feminine naturally? life is unfair...sobs)
I think that continual comparison with unrealistic beauty standards do exacerbate the feelings of inadequacies and gender dysphoria. I previously wrote about the perils of social media in destroying personal self-esteem, and it is definitely a source of immense envy and triggers of gender dysphoria. 

Although I don't hate my male body, there are days when I wished my features were less manly. The squarish jaw and ever present stubble, the veiny arms that cannot be hidden except with long sleeves, the large calves, feet and hands. And the irreversibly receding hairline (this means I can never grow out my hair even if I were willing to do so in guy mode). On worse days, I have severe cleavage envy, wishing I had a pair of boobs. Or wishing I have a typical celebrity almond shaped face framed by long wavy tresses. And even female plumbing down there, so that I could truly feel like a woman.

For a brief period of time after my wife's acceptance of my crossdressing, I started wearing women's nightgowns to sleep. They were super comfy; airy and made of a lovely soft material that felt great on the skin. Wearing them also made me feel a bit more feminine. However, after a few weeks in, I stopped doing it and went back to my cotton tshirts and sweatpants. The reason? Whenever I looked into the mirror, the person looking back was a 30+ year old guy with stubble, rough skin and a flat chest in a nightgown. It felt so weird! (Kudos to my wife for not batting an eyelid whenever I walked around the house in that). I was unable to get over the mental hurdle that by stripping off the makeup, wig and padding, I'm simply not feminine enough.

(Left: What I feel I look like. Right: What I see in the mirror. Ok maybe less buff)

Some who have seen Isabelle may comment that I am relatively passable and should be content/thankful for what I have. I do not have very hairy arms/back which would be insanely difficult to dehair, or very masculine bone structures like extra wide shoulders or a giant ribcage which would make looking like the feminine ideal and blending in much more challenging. I am quite slim and not super tall, which makes passing as a woman in Singapore a lot easier. They are probably right; I'm well aware that I am not sufficiently thankful of my blessings. But it would be foolish to berate myself more than I already do. The struggles with personal inadequacies and the feeling that I will never be female enough sometimes pull me into a darker place that I would like to be. 

Despite my many fantasies, I am also a realist. I recognise that I am male and will continue to be. That I am blessed in so many ways that I must be thankful for. Despite my occasional feelings of wanting to be a woman, they are but fantasies. I enjoy the priviledge of being a guy too much to give that all up. Also, that boat has long sailed for me; there is no amount of pills and surgery that can allow me to match reality with the unrealistic expectations in my mind. I also recognise that the root of my feelings of envy and inadequacies, although partly due to my desire to be female, are also due to my male self's lack of confidence and excessive comparison with successful / beautiful people on social media. The main hurdle here is mental. I need to learn to love myself more, stop measuring my self-worth against unrealistic standards. There is some wisdom in a local colloqual phrase from elders: "人比人,气死人" (read: incessant comparison with others leads to dissatisfaction and anger). I also need to take concrete step by step action to reach goals that will give me non-CD related satisfaction. (I'm sorry if this sounds a bit like self-psycho rant. Got to put it down to bring myself to reality)

Everyone's struggles with gender dysphoria is different; some a lot more painful than others. My own personal experience is but 1 example of the multitude of experiences out there. I hope that in attempting to describe how I feel, I do not over-simplify and trivialise what others in the community may feel.

(Yes, this is Me! So pretty right? 😝)

Yes, I have done it! 😁 After more than 2 decades, I finally fulfilled my dream of being a bride! 👰‍♀️

Previously I wrote a post about my dream of wearing a bridal gown and going for a proper photoshoot. Covid did scuttle my plans for travelling to Taiwan for a photoshoot this year, so after a fair bit of deliberation, I decided to spend my holiday budget on a studio pre-wedding photoshoot in Singapore. 

There are quite a number of bridal studios in Singapore that do gown rental, make-up and photography all within the same studio, but I eventually picked a studio located in Ubi industrial estate. Apart from pre-wedding photoshoots (indoor and outdoor) they also do family portraits, newborn, baby and maternity photoshoots. 

You may ask, how did I find a studio who was willing to let guys wear their wedding gowns? Well, I wasn't the first crossdresser who sought out their photography services, nor will I be the last either, I suspect. I came to know of the studio after chatting with another local crossdresser (Gin Kim). She visited the studio a few years back to take bridal photos and found them pretty good. With my decision to take bridal photos in Singapore instead of waiting out Covid, I sent the studio an email expressing my interest, but also pre-warned them that I was a guy. They replied almost instantly, letting me know that they were ok with it, as well as details of the package, which included returning all digital copies, 2 gowns and a price that wasn't eye-wateringly expensive (unlike some studios in Tanjong Pagar). I was pretty excited to try on some gowns, so I booked an appointment date and applied for leave (planned for a weekday so it would be less crowded)


Gown Selection

I went down to the studio on the morning of 11 Dec 2020 as Isabelle, as I knew there would be a gown fitting and I wanted to have the full experience of choosing my wedding dress. As usual, it was a mad rush to transform from uncle mode to the elegant creature that is Isabelle. It had been a while since I last dressed up, but I managed to put on a full face of makeup under 45 minutes.

When I walked into the bridal studio, I was greeted by Qiqi, the bridal consultant (and makeup artist). She was VERY friendly and professional, treating me as though I was any normal customer. At no point during the entire 1.5 hours did I feel awkward or unwelcome at all. I guess you could say she was trying to close a deal, but not everyone accepts a guy in a dress. There was another couple selecting their wedding outfit as well, so I was feeling a bit self-concious (as always), especially when I had to speak. Such situations really make me wish I did some voice training so that I could speak freely in a girl voice and not immediately out myself. Nevertheless, the studio had curtains to provide some privacy, which was great in creating that safe space. 

I wasn't prepared when Qiqi asked me about the style of gown I was looking for. Like...how about EVERYTHING? 😝 How could I not want to try the best that they had to offer! But that wasn't possible, so to help the process of elimination, I told her I didn't want a gown that was sleeveless or had tiny straps (which would emphasize my manly deltoids excessively), or a gown with a plunging neckline (since I did not have the cleavage to pull it off. I did want a ballgown style dress with a large train so that I could fulfil my inner princess' wishes. I also wanted a wedding dress in a mermaid style, as the silhouette would be just fantastic on me (with a boost to the hips using my dresstech hippads of course)

Qiqi brought me around the racks, showing me gowns which fit my description and my body size. After picking 7 of them, she led me to the dressing area and drew the curtains so that I could try on the gowns with privacy. 

The first few ballgowns were dresses with massive trains! But they were exactly the style I wanted, since it was a studio shoot and didn't require me to move around too much. Since they were all lace back dresses, Qiqi had to help lace me into the dresses (quite very tightly too). It was SO incredible to feel the dress close in tightly on my body, cinching to fit my waist perfectly. I probably couldn't remove the dress easily by myself if i wanted to. I felt so excited my heart was thumping in my eardrums and felt flushed (might have also been the spotlight shining on me though 😛). I glided around in the small stall, the weight of the gown reminding me that I was an absolute princess today. Qiqi kindly helped to snap a few photos of me in the dress. Unfortunately due to covid, I had to keep my mask on so that probably ruined the photos a little. The next few gowns I tried were in the mermaid style. Together with the hippads and a properly tight lacing by Qiqi, it gave me that glorious hourglass silhouette that this style is so well known for. 

It was so hard to narrow down the choices to the 2 gowns for the photoshoot, since all of them felt so good. Looking back, I wished I tried on more gowns of different styles and took more photos. I know some brides don't like trying on wedding dresses as it could be troublesome, but not your gal Isabelle here. Time flies when you're having fun, and before I knew it, 1.5 hours was over and it was time to go. But I knew I would soon be back for the proper shoot.


Photoshoot

The night before the shoot, I was feeling rather excited; almost as excited as my own wedding day. I got ready the night before by getting my eyebrows shaped, facial hair cleanly plucked, and epilated both legs and underarms. I also ran through all the preparations I needed to do before hand and the packing list to make sure I didn't screw up the shoot. This was because I had to go to the studio in guy mode, so there were quite a lot of stuff to bring along, namely the wig, hippads, adhesive boobs, and 2 pairs of high heels to match the gowns. I also intentionally wore a shirt rather than a t-shirt so i wouldn't smudge my makeup while taking it off.

I reached the studio shortly after lunch. The photoshoot date selected was on a weekday afternoon because the studio would be less crowded and I would feel less awkward. As expected, there was only 1 other couple but they were in the midst of their pre-wedding photoshoot so I didn't need to be in the makeup room or studio as them for an extended period. Qiqi was already expecting me. I told her I wanted to try out a long-sleeved style for the fun of it, which she obliged, picking out 2 gowns for me to wear. They both looked really pretty, but i still decided to stick with the original off shoulder dress i picked. With that decision, it was time for the magical transformation 😁

I was feeling quite relaxed as Qiqi worked on my face, chatting with her about random topics like how the studio advertised their services (mainly word of mouth apparently), tips on makeup and crossdressing, etc. It was pretty refreshing and enjoyable to have a professional do the work while I just relaxed in the leather chair, feeling assured that I was in good hands. The makeup process took about an hour or so to finish and it was time to dress up. 

The first gown was a champagne-coloured, off-shoulder gown with a diamante bodice and what was apparently the largest train among all the dresses in the studio. I stepped into the dress, held my breath, and as Qiqi tightened the laces of the gown one pull at a time, I felt...complete. Never had I thought in my youth and even early adulthood that I would be able to finally be made-up so elegantly, and wear a bridal gown of my choosing. It was a dream finally come true, the fulfillment of two decades of fantasies, when this boy finally becomes a bride. To look into the mirror and see a beautiful woman looking back, her cheeks pink with a hint of blush, her red lips parting as I smile, and the rise and fall of her bodice as I breathed in an out. I felt like a princess on her wedding day; the epitome of femininity, beautiful, waited on hand and foot, and kind of helpless in a massive but gorgeous gown. 

I finally understood why some brides like to choose a simple dress, because the massive train was more challenging than I had expected when I moved around the place. Occasionally I felt like I was going to knock of some prop unintentionally. Fortunately most of the items were pretty sturdy and I was the only other client there so there was no need to worry about embarrassing myself. 

The photoshoot started around 3pm, shortly after the other couple was done with their indoor shoot and were getting ready to head out for the outdoor portion of their pre-wedding package. The studio photographer was quite friendly and he didn't seem to mind that I was a guy in a dress. He did share that a few years back he did help take photos for Gin Kim, which was the first time he shot for a crossdresser, but has since got a bit more experience. The shoot started off with a simple lesson for me to follow his actions as though looking in a mirror to get into the poses. As he took the photos, he would correct my position with minor instructions like tilting my head slightly, sticking out my head to emphasize the jaw line from the neck, where to look, how to position the bouquet, angling my mannish-hands to hide its larger size and rather prominent veins, or positioning my feet to make my posture more feminine. It was honestly quite tiring to be posing in a massive wedding gown whilst wearing the 4 inch heels that I brought (but the heels did make me feel extra feminine so that was very important too). About 70% of the way in I was hoping to get out of the dress to take a break (oops), but decided to press on and do my best with posing. After shooting at five different scenes/backdrops, it was time to change into the second outfit.

The second gown I had chosen was a dark blue evening gown with a mermaid-silhouette and a sweetheart neckline. Qiqi switched out the accessories, adorning my hair with a circlet of faux sapphires, garnets and tiny dark blue roses, which I thought it was a good choice and matched the gown pretty well. The mermaid gown was surprisingly hard to walk in despite its significantly smaller train, but at least I didn't need to worry about knocking over a prop accidentally. For this gown, the photographer decided to go along with a more sultry vibe, occasionally having me reveal my leg and  stiletto I was wearing. The poses required next level skills in balancing and flexibility, neither of which I had 😶 

And in a blink of an eye, the photoshoot was over. I was quite surprised that 5 hours had passed since I stepped into the studio, because it definitely felt a lot shorter. It was a fantastic, endorphin fuelled 5 hours for me, not least because it had been my dream for the longest time to do a photoshoot as a bride. The staff were very professional and friendly, which also made the entire process from gown selection, makeup to the photoshoot extra enjoyable, and I am thankful for the staff for creating the fantastic experience. All in all, it was a really fun experience and something I wouldn't mind doing again in the future if I have the budget for it. It took about 2 weeks for the photos to be ready and I was very pleased with the results (even without editing, they looked great). The wife was also quite impressed with the photos and the good value of the photoshoot when I showed her the final product. I highly recommend  to do a bridal photoshoot at least once in your life, just for the fun of it, as well as to immortalise your female self at its most beautiful. 

During a conversation with another sister, the topic of regrets came up. About the "shoulda, woulda, coulda" in our respective crossdressing journeys. Like all such conversations, they are tinged with a hint of regret.

As humans, we all have regrets. Perhaps a comment said too hastily or action done without sufficient thought that caused a relationship to breakdown. Or the consequence of inaction when time and youth were on our side, only to look back and wonder if things could have turned out better than it is now. If we could wind back the clock, other than buying a ton of bitcoins to make us filthy rich, I'm sure there are turning points in our lives where we wish we could undo or redo. In the context of crossdressing, many a times it is regarding that which was not done. Fear of the unknown holds many a crossdresser back from doing what we truly desire, be it coming out to friends in our youth, joining cosplay events, exploring one's sexuality, or even making that monumentous decision to take hormones and transition to full time womanhood before the onset of the irreversible effects of puberty.

I've wondered about what I would do differently if I could turn back the time. Broadly, I think I would have done these 3 things:

1) Come out earlier
If I understood crossdressing better and was less afraid, I definitely would have created opportunities to dress up more when I was younger, and come out earlier, perhaps even in my teens. It would have allowed many experiences and a longer crossdressing runway. I would definitely have come out to my wife earlier (before we got married), which would have been fair to her. And during my exchange overseas I would have tried to live as a woman for an extended period (instead of sharing rooms with other Singaporeans).


2) Sharing my female side with more people
Not necessarily to guy friends, but perhaps to female friends who would be more willing to accept and maybe even partake in the hobby. It would be fun to go out shopping with a bunch of girls who accepts Isabelle for who she is. And what better time to do so than during the schooling days, when one has no obligations other than do well in school and not run afoul the law. Maybe I could have even gone clubbing or the prom in girl mode.


3) Taking better care of myself
I do have some facial acne scars, which were the result of genetics, poor facial hygiene and very itchy fingers. If my younger self had put in more effort, I'd probably enjoy much better skin now, which would allow me to use a lot less makeup than I usually do. I would also have gone for braces to get a perfect looking smile as well. 

Another aspect is how muscular I got in army. Although it was a great confidence booster as a guy, the large number of chin-ups made my deltoids a bit too disproportionate for a woman's typical body, which makes me avoid spaghetti strap outfits like the plague. I can do the fitspo look very well now though, and occasionally look to local influencer Jamie Pang for inspiration, whom I seem to share the same body shape (minus the hips of course).
 

4) Hormones and Facial Feminization Surgery? 
If I'm brutally honest with myself, I sometimes wish I had both of these when I were younger, although it might really be a rose-tinted fantasy more than anything. Even if I didn't live as a female all the time, being more feminine would be a boon when switching between the guy/girl mode. The permanent effects of hormones however do turn me away quite a bit, especially the chemical induced sterilisation, which mean no kids of my own.


With regards to my crossdressing journey, I think I don't have too many regrets (Can't be said for my life in general, but that's a different story). I think coming out to my wife and her acceptance, at a point in my life when I was still reasonably young and able to dress up to try out new experiences was pretty important in allowing me to check off my crossdressing to do list. Also, whatever I have done (or not done) in my youth were decisions made based on knowledge, emotional state and at that time. 

Like all regrets, it is good to think about them briefly and what should have been done, before casting them aside and moving on. As much as possible, the past should not be a spectre haunting the present and holding back a better future.

To varying degrees, each one of us crossdressers have felt guilt after participating in what society views as "deviant". Since young we have been taught that boys should only wear boy's clothes, participate in sports and be manly. Playing with dolls, wearing anything with feminine trimmings (let alone dresses) or behaving effeminately is unacceptable and an embarrassment. Society is also swift in passing judgement, branding such any boys/men who do so as "sissies", "ah-kua", "gay", "homo", or a slew of other derogatory names. With the penchant for wearing girls clothes usually manifesting around 10 years of age, it means at least a decade of lessons on how boys/men should behave, it is no wonder that there is an incredible amount of guilt when one enjoys and desires to do otherwise when they participate in crossdressing.

Guilt isn't always a negative. For example, feeling guilty for indulging in so much rich and good food over the Christmas and New Year holidays could cause people to decide to start a diet or exercise regime. Or guilt when seeing others around you participate in volunteer activities or seeing the less fortunate struggle in life may encourage one to donate money or time in the betterment of others. However, the guilt that crossdressers feel tend to be negative, leading to purging, emotional mood swings, depression, self-esteem issues and self-loathing (please note that I'm no psychologist, so this is based on my personal experience, chats with others and articles that I have read). Although not everyone crossdress for the purpose of deriving sexual pleasure, for many, wearing feminine garments is an incredible turn on. How many times over the years have you felt a heady sexual high when crossdressed, only to have guilt crash down on you like a tsunami after sexual release? It manifests in self-loathing (e.g. hating oneself for a lack of self-control) and maybe you purge or swear never to crossdress ever again, only to do so a few months later, triggered by seeing a random pretty girl on the street wearing a dress and the opportunity to dress up served up on a platter (e.g. parents on a two week holiday, leaving the entire house to yourself).

In my opinion, there are a few reasons for guilt:
  • Pleasure from partaking in the "forbidden" or "taboo"
  • Feeling ashamed of inability to live up to society's expectations of a "Man"
  • Feeling ashamed at inability to be normal
  • Feeling ashamed at the inability to have enough self-control or willpower to stop crossdressing
  • Doing something "unacceptable" behind a wife's / girlfriend's / loved one's back
I am no different. I struggled with feelings of guilt until I was in my mid-20s. To manage it, I became very adept in compartmentalising my male and female self. I knew I enjoyed wearing women's clothes and the constant cycles of self-hate, promising to do better and failing was just depressing. I rationalised that just by wearing pretty outfits and wigs at home, as long as no one knew, I wasn't hurting anyone and was still able to enjoy myself. A win-win situation. That said, coming out to my wife and with her acceptance of my female side helped reduce this guilt tremendously, since crossdressing was no longer "wrong". I was also no longer dressing up as Isabelle in secret behind her back.  

Many of you who read this may still be early in your journey, or still deep in the closet. Regardless, it is important to take care of your own-mental well-being, and come to terms with the fact that the female and male sides of us are two sides of the same coin. Stop beating yourself up over what society views as "forbidden"* and learn to enjoy the journey. As long as you're not harming or hurting anyone, crossdressing is just another more peculiar hobby.

[*Note: Although my post is encouraging you to adopt a YOLO mindset a little, it is solely in reference to crossdressing. There are some "forbidden" activities that are truly abhorrent and should not be enjoyed under any circumstances, such as abuse, torture and others too horrifying to list]
(No, this is not me or my baby. But what a beautiful shot)

SURPRISE! I'm actually a girl and I gave birth to a baby! 😬😝

Ok I'm being rubbish. No I'm not a woman, but I did have a new addition to the family not too long ago. 

Being parent to a baby is tiring business. Your time is no longer truly yours, you can't remember when you slept 8 hours in a row without waking up between 1 to 3 times, and honestly when there's some free time you're usually so tired you just want to lie down and vegetate to Youtube or take a nap (not epilate hairy legs, shave, apply makeup for 1 hour just to put on a dress to take some photos and revert back to male-self after). The wife and I have had to make adjustments to our lives to make space and time for the baby. That said, it has been a very rewarding journey so far. Who knew a tiny human being could bring so much joy to not only me, but everyone else around.

So how has a new baby changed my ability to dress up as Isabelle? Well prior to delivery, we knew that the confinement nanny would be living in with us for the first month and my MIL would come to help regularly from the second month onwards. Which meant all of my female stuff that I took out and kept in the open after coming out to my wife had to be squirreled away again. I used to have a section of the study room cabinet dedicated for my girl clothes. Even my wigs were placed on stands to reduce tangling. The clothes were cold stored in vacuum bags to save space (yes I do have a ton of female clothes) and the wigs went back into their original packaging.

(Left: My girl clothes hug up. Right: Vacuum packed my clothes)

I also knew that I had to go cold turkey for at least 4 months after the baby was delivered, so I went on a crossdressing binge in the lead up to the estimated delivery date. Outing with other fellow sisters? Check. Bikini by the pool? Check. Photo of Isabelle in front of the waterfall at the newly opened Changi Jewel? Check. My final outing at Jewel sated the woman in me quite a bit, and I hoped that between work, caring for a newborn and new experiences meant that I had no time and energy to think about crossdressing.

Man was I wrong.

During the 4 months after my final outing, I suffered from a severe urge to dress, something that I had never felt so strongly before. It was actually the first time in my life that I was truly unable to create the opportunity to let Isabelle out. In addition, slipping on a dress or feeling soft fabrics no longer did anything for me. It was all the way or no way. Without epilating, proper plucking of facial hair and a full face of makeup, I felt manly and incomplete, so in order to let Isabelle loose, I needed at least to prep 1 day before and 2 hours on the chosen date to doll up and de-drag. Impossible when the confinement nanny or my MIL was in the house. Absence makes the heart grow fonder, and Isabelle screamed to be let out. Finally, I did get my chance around Christmas, and boy was it liberating 😁

From the fifth month on, my child care plan  change a bit, which allowed me to have my private space at home during weekends. However, dressing on weekends meant that 100% of the baby caring load fell on my wife  As I didn't want to let the wife shoulder baby caring alone while Isabelle went out shopping, it meant that the only real window was to apply for leave on weekdays to allow for sufficiently long guilt free crossdressing time. Which was fine really, since all leave reserved for holidays have been shelved (I can't imagine dragging my kid all around for a week overseas). This was the new normal for catering time for Isabelle to get out.

Some of you may ask if I will ever reveal Isabelle to my kid. I've thought about this question before and the answer is not until she is mature enough to understand the variations in the gender spectrum and what gender dysphoria is all about. It wouldn't make sense to confuse my kid when she is still young and couldn't possibly understand. Also, I really couldn't risk having my kid accidentally outing me to my own parents. Imagine my kid going up to her grandparents and say, "Last weekend Daddy dress like a pretty girl" (oh that would be catastrophic).


Work has been extra stressful of late, with impending hard deadlines, multitude of presentations lined up and long work hours. There are days I just wonder if there is more to life than just working from Mondays to Fridays (maybe on weekends too), grinding at a job that doesn't give me much satisfaction, just to pay the bills, save for retirement and go for that occasional holiday. I suppose I am lucky not to have lost my job during this Covid-19 period, which has been challenging for many people. 

Nevertheless, work stress is what it is; a source of worry that makes one work harder, but also wish for some form of reprieve or escape. Unlike schooling days, where the stress of exam ends at the end of the year, work never ends. So the stress just lingers, spiking now and then as deadlines arrive. Some thrive on it, and a bit of stress is always healthy, but too much and the cracks start to appear.

For me, work stress causes my sleep to be less restful, increased grouchiness in the day and my gender dysphoria to flare up more than usual. Feelings of wanting to let Isabelle out and the desire to be a woman rush to the surface like a wellspring. It could take the form of wishes of being a beautiful model wined and dined at fancy restaurants in elegant outfits, or a elfin-faced cosplayer dressed in pretty lolita outfits. A simple photo of a girl with a skinny waist, glorious looking cleavage, or an elegantly worn outfit could send me to fantasy land. Anything to be away from endless emails and powerpoint slides. I'm sure I'm not the only one who feels this way.

As much as letting Isabelle out is a balm to my stress, I know that it isn't the cure. My brain is turning to a known form of relief and hoping that somehow, by partaking in dressing up and unrealistic fantasies, it would solve the root problem. Such thoughts are nothing more than escapism. There is a need to manage such emotions and make an effort to address the cause of the stress, rather than to attempt to run away from it.

As far as countries go, I'd say that Singapore is one of the safest in the world. Homicide rates are very low in Singapore and there's near zero chance of being shot (in part due to the lack of access to guns). Even petty crime appear to be rare, although the police will likely say other wise. The perception of a general absence of crime is so prevalent that people develop a sense of complacency, being perfectly comfortable to leave their bags to "chope" or reserve seats at the hawker centre. This is shown in the chart below.
(Image extract from Asiaone article)

That's great for residents of Singapore of course. But keeping in mind that as an Asian country that is somewhat conservative, a sizable portion of the population that is religious and the fact that society in general isn't too supportive of guys wearing women's clothes, how safe is it for a crossdresser in Singapore, especially one that goes out in public?

Well, the good news is that there's a very low risk of being stabbed or attacked for crossdressing in public, if one is just minding their own business. Even if some people will frown on crossdressers, stare or maybe name call (ah-kua, bapok or other slurs), violence is highly unlikely. This is especially if one goes out to public places where there are a bit more people, such as shopping malls, parks, airport, etc. So far in the 10 plus times I have been out in public, I have never felt unsafe. Of course I do try to keep a low profile and not draw excessive attention to myself.

I cannot imagine crossdressing in a place where people have easy access to guns and religious conservatives have very strong views about what a Man should and shouldn't wear. Perhaps I am wrong, but the presences of these 2 factors just raises the risk of being a recipient of hate crime significantly.

So if you're coming from out of town to Singapore and plan to crossdress, I'd say you'll be very safe. But do plan your trip around air-conditioned place, because the humidity and heat can KILL 😅
When I was still in the closet, I felt very alone and didn't think I would meet others who had a compulsion to crossdress. Websites at that time about crossdressing were largely limited to sources from the USA and UK. How was a crossdresser who was so deep in the closet and fearful of telling people about his secret going to find peers in Singapore? Well, fast-forward to 2018 and the internet is a very different place than it was before. Since I had come out to the wife, I decided to reach out into the community via forums (like the now defunct Sgbutterfly) and Instagram to chat with people similar to me and hear about their experiences. I'm glad I did so, because I discovered a whole community of local crossdressers in Singapore. We may be few and far between, but it is nice to know that we are not alone. 

It turned out that back when I was in my university days, there have been quite an active community that started off mainly from the forum Sgbutterfly. One of the main groups is Sggurls, by founder Nicole. Apparently in the group's hey day, the gatherings were pretty large, as seen from photos in old blogs like this. I don't think crossdresser gatherings in Singapore are this large and happening any more, partly because they aren't easy to plan. Many crossdressers in Singapore are also in the closet. Nevertheless, having chatted with more local CDs, I've come to know that there are quite a lot of small group gatherings that typically take place in hotel rooms or restaurants (for the bolder and more experienced). I've participated in some of these and it's really nice to have a safe space to doll up, chit chat, share dresses, tips, life stories and take a crap ton of photographs. 

I've also come to know, that a short 4 hour drive away from Singapore, in the bustling city Kuala Lumpur (or KL, as it is usually referred to), there's a vibrant crossdressing community. It's pretty amazing, because there are annual events organised by a core group, and crossdressers from various parts of Malaysia (Ipoh, Johor, Penang) drive down to attend the gathering. It has even attracted Singaporean crossdressers to join the fantabulous weekend escapade! Singaporeans and Malaysians, building diplomatic bridges one sparkly dress and sky high stilettos at a time! Unfortunately, there's Covid-19 raging everywhere, so going into Malaysia to join such an event will need go be on hold for now.

(So many crossdressers at the Malaysian event! The organisers are honestly amazing. I might get flak for posting a group photo publicly, but it is so grainy its impossible to make out anyone's features, and this photo was somehow found on Quora)

The last and most out of this world crossdresser gatherings are in none other than the LGBT friendly Taiwan! While starting out on Facebook, quite a number of very convincing crossdressers seem to be Taiwanese. Some background research on their profiles (*ahem* stalking) showed that not only does the Taiwanese crossdressing community have pretty regular gatherings in cafe and in each other's homes, every year they have massive 伪娘 gatherings. The photo of the 2019 event had upwards of EIGHTY crossdressers! It was like a mini company dinner and dance event with a stage, emcees, activities, photobooths and what not. Would be great if I could participate in one of their events sometime in the future. 

I don't think Singapore's community will be anywhere near the scale that Taiwan does it. But it isn't a competition, and as long as we find a friendly and like-minded group to regularly chat with and gather for dress up sessions, it's more than one can ask for. 
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