Musings of a Singaporean Crossdresser

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)

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.

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:

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).

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.

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).

 

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:

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.

(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).