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Musings of a Singaporean Transgender

(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. 
(I wish this was me)

The sisters whom I chat with regularly know that I've got a massive penchant for bridal gowns. It's a once in a lifetime outfit that epitomise elegance and feminine beauty. Call it a fetish if you will, but it is my dream to experience having my bridesmaid lace me into a form fitting gown, feel the delicate lace, satin and silk against my body, the weight of the dress as I glide onto a pedestal, and see a beautiful bride in the full length mirror.

To satisfy my desire, I went shopping on Taobao many years back and actually bought a bridal gown with a mermaid silhouette a number of years back. It's pretty amazing what one can buy from the Taobao and how cheap it was. Including the veil and underskirt, the entire outfit cost me $70. I wasn't too hopeful based on how much I paid and the quality of the fabric did show; the satin and lace were slightly rough to the touch. Nevertheless, the dress did look more impressive than I expected. I still remember myself trembling with excitement on a weekend where my parents were out of town and I had the house to myself. Unfortunately the dress was a lace back style rather than one with a back zipper, and I quickly found out why brides actually need bridesmaids to help them change into their different dresses during wedding banquets. After five tries I eventually did succeed in lacing up the dress, but it wasn't as tightly done as I wish, resulting in a cylindrical silhouette rather a beautiful mermaid I had imagined 😑

(The mermaid silhouette I imagined but was unable to achieve)

I'm not sure how this preference for elegant outfits came about, but it's something I've been desiring for the longest time. Perhaps it was due in part to society's messaging to little girls about being a princess, successful advertising from the wedding industry machine and knowledge that as a guy, it was unlikely that I would get a chance to wear a bridal gown (after all, we crave strongly what we cannot have). I wrote about enjoying gown selection with my wife during my wedding prep in an earlier post, but I think we can all agree that choosing your own outfit is definitely better. 

With social media, I found out that this dream might not be too far fetched after all. Many sisters, both local and overseas have gone for bridal photoshoots, to capture them at their most beautiful and immortalise it in photos. Ever since, one of the items in my bucket list is to do a proper bridal photoshoot...with me as the bride. As far as dreams go, it is one that is quite easily fulfilled, as long as I set aside the budget for it and find a suitable, willing (and good) studio.

Unfortunately, as many newly-wed couples can attest to, bridal or pre-wedding photoshoots as it is called, is very expensive to do in Singapore. I did a few casual checks with bridal shops with an indoor studio and the packages quoted were at least $1,500, for 1 gown and a limited number of digital photos. Some shops quoted a minimum package price as high as $3,000+! To be fair, labour in Singapore is quite expensive, and the studios that quote a higher price do appear to have way more elaborate gowns and prettier advertorial photos on their social media page, promising a fantastic and unforgettable experience. But to spend $2k or more on something as frivolous as a wedding photoshoot does make my inner budget concious uncle flinch a lot.

More experienced sisters have recommended me to do my photoshoot in Taiwan instead. Not only do they have a huge number of photography studios in Taipei, the outfits, studio sets and photography style is more varied (e.g. steampunk, 古装, lolita, cutsey gowns, normal bridal styles, etc). Not only that, Taipei is LGBT friendly (some studios explicitly state that guys can crossdress), as well as wallet friendly. I had originally planned to head to Taiwan at the end of 2020 to do a photoshoot, but Covid-19 decided otherwise 😑 Covid-19 please go away soon so that life can go back to normal and we can all enjoy travelling again. 

(UPDATE: I've fulfilled my dream! You can read my detailed gushing of the entire experience here!)
(That amazing feeling when you buy a new, pretty outfit)

Guy's clothes are generally quite boring. It is no wonder guys are generally uninterested in shopping for clothes (I can't say the same for things like cars and tech gadgets which guys tend to obsess over).

Shopping for women's wear on the other hand is just OMG. It is just so much fun. There different styles, fun colours, cute accessories, the perfect item to match something you currently own. I never really understood why women loved shopping so much until I finally did so in person while dressed as a girl. I do a lot of online shopping and it's pretty great too, but it doesn't beat the experience of browsing the clothes in person, feeling the soft lovely fabrics with my fingers, holding up dresses in front of the mirror and trying outfits in the changing room. There's also a waiting time involved with online shopping as compared with shopping in person, where I get INSTANT GRATIFICATION. 

To date, I have gone shopping in girl mode around 10 times. The first few times have been quite scary, but just like most escapades, they felt extremely liberating. It was good fun to walk around the shop and pretend to be a normal girl browsing for clothes. After a while, I realised that in clothing shops, other shoppers are too engrossed in their own browsing that they don't pay me much attention. The only ones who occasionally give the odd glance are bored companions who are stuck shopping with their female counterparts. 

(Not in Singapore, but I think this is quite universal 😂)

I do have a few favourite shops I like to hit every time I go out shopping. They're large retail brands, so the shops are usually larger and I'm not squeezed into a tiny outlet with one sales personnel looking at me all the time, which makes me a lot more relaxed.
  • H&M - the huge full length mirrors and lighting are fantastic for photos😍
  • Zara - High street fashion. Nuff said
  • Forever New - Dresses are good quality and so pretty...but they're more suitable for dinner events and rather expensive
  • Cotton On - For the budget conscious babe. They've got decent yoga wear
  • Love Bonito - Local brand. Their stuff look and feel so good for some reason I think lined dresses feel nicer
(Random dress from Forever New. So damn pretty I want it)

I've been told that there are many other great shops out there that I should visit as Isabelle, like Love Bonito, MDS Collections. Lingerie (Victoria's secret, La Senza) and makeup shops (Sephora) are also surprisingly welcoming to crossdressers who look interested in what the shop has to offer (Probably because we are potential customers, sales staff have seen all kinds of people and when they treat us like a normal girl we'll happily whip out the $$). Although I generally avoid social contact when I go out in public, other sisters who shop frequently in person have told me that their experience with sales staff have been overwhelmingly positive, which is another reason for me to feel less self-conscious about myself.

There has been an awkward experience for me when trying on clothes in the shops though. I was shopping quite near to the shops' closing time, so the sales staff were getting ready to finalise the accounts and close for the day. While trying on outfits (and snapping a few photos in the process), I lost track of time and was probably the only one left in the changing rooms. The sales lady came to check by my stall and asked: "Ma'am, we are finalising the accounts, are you paying by credit card or cash?". I was very flustered, and my silence made her ask the question again. Finally I replied in my guy voice, "I'm almost done, sorry.". The sales lady got a bit of a shock and promptly left the changing room. Feeling super embarrassed, I quickly changed back into my clothes and left the shop.

After that awkward experience, I learnt not to (i) shop near closing time, (ii) pick a gazillion outfits and end up too long in a stall and (iii) be too quiet otherwise the sales person might come and do a spot check to see if there was anyone in the stall.  I don't think trying out clothes in a changing room reserved for females infringes any laws in Singapore , but it is better to be safe than having the cops called on me.  

Unfortunately, I've been incredibly busy and it has been a number of months since I have had the opportunity to go shopping as Isabelle. Hopefully my schedule will clear up and I'll do so before the year ends. This gal needs some Christmas lovin', and a pretty red dress would do the trick
(Nope, this isn't the type of breastplate I'm talking about. But this would be pretty cool)

All of us crossdressers dream of having a pair of perfectly shaped breasts with a fantastic cleavage. But unless you have a fair bit of chest fats, take female hormones over a period of time or go for breast implants that's pretty impossible. It means something is missing when we wear plunging V-necks, outfits with sweetheart necklines...let alone bikinis or lingerie.

Enter the silicone breastplate (No photos, otherwise my blog might be flagged as NSFW. But you can easily google them yourself). These are different as compared to normal breastforms which are 2 discrete "boobs" that you stick onto your chest. A breastplate is a skin tight, skin coloured silicone shirt with two breasts attached to it. By artfully hiding the neck, arm and waist seams, it promises crossdressers fulfilment of a dream; boobs that are not just realistic looking, but have a weight and bounce just like the real thing, a convincing cleavage and a feminine looking rack. Advertising for such products have gotten really good too. Watching such videos made me really want to purchase a breastplate. But it wasn't cheap, and I heard mixed reviews from fellow sisters who have purchased silicone breastplates. I finally decided to buy a set during a moment of weakness on one of those Taobao sales events (I got mine for S$140...and the lack of quality shows. The really good quality ones can cost up to $2k USD)

I have to admit, I was buzzing with excitement upon receiving it, but after trying it on, it was an "Expectations VS Reality" moment. 

I had a few issues with it, the biggest being how damn hot it felt while wearing the breastplate. Even with the air conditioner at full blast at the lowest temperature, I could feel sweat pooling underneath the silicone breastplate. As I moved around a bit, the silicone/skin seal would sometimes break and I feel large beads of sweat flowing down. Not fun. As if wearing a wig in Singapore's humid climate wasn't warm enough, I had to wrap a quarter of my body in silicone. Perhaps in a temperate country the breastplate would make more sense.

Other issues included how tight the silicone felt on my throat, which constantly reminded me of its presence, how obvious the seams were, how stiff the boobs felt and strangely, an oily layer on the boobs despite multiple washes. Perhaps the last 2 issues were brand specific, since I had no such issues with my dresstech hippads which felt high quality (price was high quality too, at S$300),

There are good points though. The breastplate has a very nice weighty bounce when I walked around, which was different from normal breast forms. It has also allowed me to take pretty good boudoir photos (Note: good is relative. Maybe someone might think my photos are absolutely crap). With some post editing to remove the seams and blend the colour tone to match my skin, it did look like I had real breasts. I've been doing a bit more boudoir shots to get mileage out of the breastplate. 

Despite the issues I have with my purchase, after trying it on a few times I have gotten used to them and look for work arounds. Like stuffing a ball of tissue to absorb the sweat, or selecting outfits that hides the arm seams well. Looking back, I don't regret my purchase

So if you are still undecided whether to purchase a silicone breastplate or not, maybe the following points can help

You should buy a silicone breastplate if:
  • You have spare cash
  • You want your lingerie/cleavage revealing photos to look better (after editing)
  • You are aware that the seams are very obvious
  • You are aware of how much you will sweat wearing it
  • You are aware that it is different from your skin tone
  • You cosplay and want massive knockers to match your character

You should not buy a silicone breastplate if:
  • You want to have "real" breasts and the breastplate will help you pass in public
  • You are just starting out crossdressing and don't have other essentials yet
  • You think they feel like real boobs
  • You think the neck/arm seams are not obvious in person (they are damn obvious)
  • You don't have good hippads. Hippads are way more important in passing (read more about hippads here)
  • You don't have spare cash (please just save the money)
Janna montana also wrote a very well written and detailed piece about the pros and cons of breastplates based on her experience. Anyone thinking of purchasing one should read her post before doing so.

Ultimately, it is your money and your choice whether to purchase a silicone breastplate or not. But it isn't cheap so do your research before getting one so you don't end up with buyer's remorse. As a note of caution, Taobao breastplates seems to be one size larger, so ordering a "C" might net you a huge "D" rack instead

This is a topic that is applicable to many people, not just to crossdressers, but I'll try to link it to crossdressing.

Instagram and facebook is pretty fun in general. We use it to connect and chat with people sharing the same interests as us, we posts photos of ourselves having fun and get praises, which gives us that little hit of the happy drug doapamine when the photo gets a ton of likes or comments that we're pretty/beautiful.

However, ever since I started using social media for my female self a bit more heavily, I quickly noticed 2 big issues which makes me think twice about maintaining the social media account.


Addiction


I started my open Instagram account back in Nov 2018 as a bit of an experiment, to see how many followers I could rack up and share my photos. I decided to post daily to generate activity and encourage followers. 

After about a month in, I shut my account down. 

I found that I was starting to be addicted to social media in a very unhealthy way. I spent way too much time open and closing the Instagram app to check if I had new followers, likes and comments. I started obsessing over how each new post compared with the earlier posts in terms of likes and comments. After posting a new photo, I'd start thinking about which photo to use and what caption to write for tomorrow's post. 

The addiction and obsession got a bit scary for me as I never felt it before in my guy mode. How much of my waking hours did I waste looking at social media apps and obsessing over something so superficial and vapid as comments and likes? It was so easy to do a double tap to like a post, or write a simple (and possibly) meaningless "Beautiful girl". After a while, I noticed that some followers basically commented on every post, which was akin to casting a wide net on many women, probably hoping for a reply.

Instagram wasn't the only culprit. There are so many places to while away your precious time and life, such as Facebook, Reddit, Twitter, etc. In small doses, social media is fun, but once it becomes obsessive and there are clear signs of addiction, I think it important to do a detox.


Negative Impact on Self Esteem


I believe that everyone has moments where we doubt ourselves and self-esteem is momentarily placed in question. Nobody is perfect. However, excessive use of social media tends to trigger unhealthy amounts of comparison with unrealistic standards, which can cause self-esteem issues.

Firstly, photos posted on social media are very curated. Only 1 out 10 photos taken make it to the Instagram feed (statistics not substantiated...but you get what I mean😜). This means no unglam photos, no accidental double chins, extra fats are hidden by a good photo angle, etc. I am guilty as charged! My social media accounts for both my guy and girl mode only show the best photos (of course my guy mode has way lower standards)

(Transgender Beauty Queen Yoshi Rinrada. Can you believe she was born male? Real girls will kill to look like this)

Secondly, we tend to follow certain accounts on social media. For crossdressers, these tend to be transgender beauty queens, beauty influencers, cosplay cuties and other prettier crossdressers in the community (as much as we hate to admit it, everyone wants to hang with the pretty and popular crowd). Seeing these beauties on a regular basis warps your sense on reality, making you think that such perfection in beauty is the norm. It simply isn't! Take a walk in the shopping mall and how many "Goddesses" do you see? Probably not as many as your Instagram feed. Yet sometimes I do the silly thing of comparing myself with someone like Yoshi Rinrada...it's almost akin to comparing myself with the Olympics Gold Medalist. The problem of comparison can be even more acute in crossdressers; after all, we are further from our ideal image, since we don't have real boobs, wide hips or other obviously female features.

Finally, images online are usually edited in some form or another, they simply aren't 100% real. Of course there are really beautiful people who don't need photo editing software, but most crossdressers have used apps to smooth out skin imperfections, sharpen the jaw, enlarge the eyes, and apply beauty filters. I do that too, just to make myself look slightly better, but it just means what you see is not the real Isabelle. With apps like "Faceapp", it is even harder to tell if an image is real or not. So comparing ourselves to images that have been edited and perfected to modern beauty standards...is kinda dumb.

After using social media a bit more heavily, I finally understand why an increasing number of 16 year old teenage girls face self-esteem issues. 

(Some days just kind of suck)

Even without venturing onto social media, I struggle with some self-esteem issues. My skin isn't the best, I'm not as confident as I should be, and I always feel like I should and could do better. But when I feel really frumpy or hopelessly imperfect, I try to recognise that I am in a rut and the only way out is to stop digging myself deeper into it.

I'm jumping back to an earlier part of my crossdressing journey to share some of the random imaginations I had, which I believe you may have had too.

The human mind is an amazing thing. It is able to conjure up all sorts of fictitious situations that allows us to go on adventures that we cannot do so in reality. Before your own imagination runs wild, no this post is not about smutty scenarios. 


Wishing for a Miracle


I was from a partially religious family, in the sense that my mum is a really devout Christian. Since young, I was taught to believe that God is out there and he watches over us all. Every night we would sit in front of the alter and say a short prayer to give thanks and praise. I remember in my upper primary school days, I would slip in a short prayer to God for a miracle, that I could wake up the next day and be a real girl. But each day I would wake up the same, leaving me slightly disappointed but nevertheless hopeful that maybe God decided it wasn't time. Being a kid, I didn't know better and always made the same wish during other opportunities; wishing to Santa during Christmas to make me a girl since I had been a good boy, making a silent wish during my birthday just before I blew out the candles, or wishing upon a shooting star even though I could not even see any in Singapore's night sky.

Of course none of the wishes came true. As I got older, I gave up making such wishes and accepted that there was no such thing as "magic" or "miracles".


Characters in Video Games
(Female Commander Shepard from the Mass Effect Games)

Magic in video games though were in no short supply. I used to play a fair bit of video games and in a number of them, I usually projected my wish to be a girl onto these characters. RPGs were the best, since I could create a character and pretend it was me going around completing quests. The character was always female, as pretty as I could make the character based on computer graphics of the time. If anyone asked why my avatar was female, my go to excuse was that it is nicer to look at a female avatar.

In Diablo 2, I was the sorceress fighting off evil demons and casting powerful magical spells. In Final Fantasy 8, I was Rinoa, the pretty porcelain skinned beauty. In the Mass Effect series, I was female Commander Shepard, killing genocidal aliens, saving the galaxy, whilst banging the hot lesbian crew mate. Even in a real time strategy game like Starcraft, I imagined myself as being placed in a chrysalis like Sarah Kerrigan, only to emerge a real woman. I probably played way too many video games in my youth, but I look back to those memories fondly.

I truly looked forward to the day where VR has become so advanced that we are able to plug into a simulator so realistic that we could be anyone we wish to be (just like the movies "Ready Player One", or "Inception", but less dystopian)


Superpowers


Ah superheroes and their powers. I'm not just referring to the Marvel or DC Universe, but any fiction where there are superpowered beings. Popularised by comics, books, movies, games and even Anime, everyone wished they had superpowers at some point in time.

So what superpower did I wish I had when I was younger? Looking through the full roster of X-men mutants, the superpower I wanted the most was Mystique's power of shapeshifting. Yes, Wolverine was super cool, Magneto was powerful, but the power to take on any form at will? Count me in! I imagined taking the form of famous and beautiful actresses of the time and living as them for a time, wearing dresses and living the high life.

The other power I imagined having was the ability to stop time. If I could freeze everything and everyone but me, I could freely roam about the shopping centres, trying on women's clothes without fear of people stopping me or calling me out. One of the first places I imagined going to was a bridal boutique. I would stop time just past morning when the shops are open and help myself to the buffet of wedding gowns on display. I'd secretly sneak my favourite gown home so that I could put it on anytime I wished.

Thinking back about it, it was really a silly phase of wild imagination, reflecting my inner thoughts about wanting to be a girl.

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