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Musings of a Singaporean Transgender


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

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

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

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

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

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

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


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

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

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

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

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

There's nothing wrong if crossdressing turns you on. But always remember, everything in moderation 😉
If you asked me before 2019 whether I would dare to step out in public it would have been a flat out no. And if you retorted to say that not only would I dress up in public multiple times, I would also participate in an interview as Isabelle for a video that would be shared on multiple social media platforms, I would say that you were insane (and probably stopped talking to you).

Oh how wrong pre-2019 Isabelle was.


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

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

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

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

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

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

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




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

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


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

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

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

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


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

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

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

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

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


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

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

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

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

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

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


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

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

Looking back though, my outfit was super cringey. I looked like crap, my wig was a wreck, my makeup was barely there and my looks wasn't great for going anywhere (the whole look even looks like garbage in the few photographs I took). But we all have to start somewhere. This event was the beginning of my adventures as Jessica in public, and in spite of my amateurish dressing, I'm glad I took the plunge and opened the door to expressing my feminine side."
- Jessica aka Microsoft Excel 2007 (Canadian)


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

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

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

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

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

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


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

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


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

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


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

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

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

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


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

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


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

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

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

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


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

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

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


7a) Retirement
Sadly, the fires of excitement that burned so brightly in the past will fade away with time, either due to age, fatigue from crossdressing or a lack of novelty. Once everything in his crossdressing to-do-list has been checked off multiple times, he may decide to hang up his stilettos, little black dresses and retire for good. 

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


7b) Full time girl mode / Transition
For some crossdressers however, dressing as a woman reaches an inflection point; he realises that his gender dysphoria is so strong that the infrequent crossdressing isn't sufficient to meet his personal needs. He is transgender and wants to spend his time living as a woman permanently. Whether he undergoes hormone replacement therapy, feminisation surgery or SRS, this threshold is the largest one to cross, as he isn't a crossdresser anymore; she's now a woman. It is very challenging, as it requires her secret to be made known to relatives, friends and society. But despite its challenges, there are success stories of crossdressers who eventually live full time as women. 


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

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

To be honest I was considering whether to write about this or not. 

I have mentioned before that crossdressing is just like any other hobby, where people with a shared interest chat, meet up and participate in the activity that brings them so much joy. However, there is one major difference which sets it apart. The unfortunate reality is that when we crossdress, we take on a female name and persona of our own creation. Isabelle is my creation and my circle of friends who crossdress also know me as Isabelle. Although the thoughts and experiences I share with others in my chats, as well as my blog posts are true, I am ultimately still hiding behind a facade; no one really knows my real name, what I do for a living, as well as other aspects of my life. Such a separation of male and female lives is my isolation by design, and a strategy that many other crossdressers also adopt. This is because, it allows me to completely cut-off all ties should the need arise. Because the risk of my secret hobby being made known via another party (intentionally or accidentally) to relatives, other circle of friends or worse, colleagues, is too high for me to bear. Like any other friendship, circumstances can turn it sour. In especially bad scenarios, it can become hateful. Crossdressing is quite a superficial hobby and many who partake have different priorities, objectives and complicated life-stories. I've heard way too many stories of animosity developing over time within the community and in the same chat groups due to differing views or plain cattiness. As a fair amount of private info can be shared within such groups, being too open would increase my risk profile. I cannot fathom the regret I would feel if someone were to out me to my relatives/friends/colleagues. Even if such an action would brand the person a pariah, the damage would be done. 

As such, even if someone is willing to open up to me or share their personal phone numbers, I usually find it hard to reciprocate, since our risk profiles are different. The other party may already be out of the closet, careless with secrets, single (and thus do not need go worry about partners), or worse; catfishing. Whereas I'm only out to my wife and plan to keep this delicate balance for the rest of my life. I generally don't chat with or add profiles on social media that cannot be corroborated with other known crossdressers in the community, don't show their faces, or hide behind heavily AI-edited photos (i'm looking at you FaceApp). The irony is that if my younger self were to reach out to my current self now, I may very likely ignore my younger self (oops). 

This behaviour might be viewed as being uppity by some for not replying to messages/chats or accepting friend/follow requests on Facebook or Instagram, but I simply cannot adopt a careless attitude with regards to privacy.

That said, it is possible to have close friends within the community. I've seen some groups in the community who spend a lot more time together than with their other circle of friends and hanging out not only to crossdress, but to enjoy other aspects of each other's friendship. This is really great and comforting to see. Friendships is more than just a shared hobby. Hopefully in your journey, you find your own close knit group of friends.

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. 
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