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Musings of a Singaporean Transgender

(I wish this was me)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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


Addiction


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

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

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

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

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


Negative Impact on Self Esteem


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

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

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

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

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

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

(Some days just kind of suck)

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

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

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


Wishing for a Miracle


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

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


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

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

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

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


Superpowers


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

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

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

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

(Me when I see that beautiful evening gown)

Crossdressing is such an expensive hobby. 

I can imagine some of you girls are already nodding in agreement. The amount of money spent on kitting out the female wardrobe and trying to look convincingly female adds up to a surprisingly substantial amount.

Some of you may argue that, no, crossdressing can be done on a budget. All you need are a dress, a wig from Taobao, undergarments from Cotton-On, stuff the bra cups with socks, a pair of simple flats and Voila! Guy to Girl in under $60. Well, that does count, but how long before another pretty dress or gorgeous pair of high heels captures your attention? And you'll need a daily outfit, a formal outfit, an OL outfit (or maybe 3 🤣), etc. The costs add up! Not to mention, guys need additional paraphernalia to properly achieve a more feminine look.

Of course, you may also argue that there are even more expensive hobbies out there (e.g. vehicle modification and detailing, skiing, skydiving, collecting luxury handbag, raising a child 🤣), but for an activity that is done so infrequently, crossdressing ain't cheap! 

Let's do a very rough breakdown of money I have spent over the years to feed the woman inside:

Clothes = $4500 (too many to properly count. I may have underestimated)
Lingerie = $400 (I'm guilty for having way too many lingerie sets)
Wigs = $600 (I've 15 cheap Taobao ones, and 1 expensive Girl Hairdo one)
Makeup = $400 (drugstore. Includes brushes)
Shoes = $500 (8 heels, 5 flats)
Breastforms = $250 (4 forms, 1 breastplate)
Padding = $350 (1 taobao pads, 1 dresstech hips)
Accessories = $150 
Photoshoot = $938 (did 1 in japan. Results were meh. And a bridal shoot in Singapore)
Total = $8,088*
(*Updated as of 2022)

I'd say my expenditures might be in the medium range. Some sisters who go for branded rather than drugstore makeup, regularly rent hotel rooms to crossdress or undergo permanent hair removal will see their costs shoot way higher. And most would have purged their perfectly functional female wardrobe at least once during their journey, which further adds to the costs.

But like my dad likes to say: "钱赚来就是要拿来花的"。(Loosely translated: We work to earn money, so it is only right that we spend it"). Despite being an expensive hobby, crossdressing makes us really happy and we are very willing to spend on the inner woman. Life is short, so we should try to create as many happy moments as we can. 

Nevertheless, I believe it is important to focus on what the guy mode does to grow our finances properly. Only when we are well able to meet our basic human needs do we have the mental and financial bandwidth to properly spend on our hobbies without worries. Swap out "crossdressing" with any other hobbies or whims in life and it still generally holds true.
(I wore 4.5-inch heels the first time out. Highly NOT recommended if you lack practice)

Looking back, it is pretty amazing how far I have come on my crossdressing journey. If I were to ask my younger self if I would go out in public dressed as a girl, it would have be unfathomable. I've no regrets to do so, because it is very liberating to go out in public and do simple everyday stuff like shopping. The first step out in public is always the hardest, but one of the most memorable.

Since the eventful big reveal to my wife about my crossdressing on 16 June 2018, many things have happened. My wife saw my female self for the first time ever. I have my own wardrobe of girl's clothes (hung up and arranged according to colour), I started getting a bit better at make up after more practice and I started ordering clothes online to be delivered directly to the house. The next major milestone for me was stepping out into the public's eye as a woman.


This started with me going onto the now defunct SG Butterfly forum to chat with like-minded individuals who were interested in dressing up. It was great that the conversations were pretty decent (moderators clamped down hard on soliciting of sex and NSFW content), so it was just clean chit chat about crossdressing. Up to that point in time, I had never really communicated with local crossdressers, so I was pretty curious to meet up with a few in person to find out why they crossdressed, how they dealt with life and a bit more on the local community. Of course, I made sure to tell my wife about my intentions and got her approval to meet other sisters within the community before I did so. 

The first time I ever met fellow crossdressers was on 27 Oct 2018. It was the halloween weekend (a.k.a the holiday season for crossdressers), so it was timely to plan for an outing in public. At that point in time, my goal was just to dress up and chit chat indoors and I had zero intention of going out in public. The organiser booked a small room in a 3 star hotel as a private place to transform ourselves from normal guys into girls. The room was clean, but was tiny and felt a bit budget. Nevertheless, it served its purpose as a base to dress up. Including myself, there were a total of four crossdressers during that meetup, and it was the first time anyone in the group had met each other. After a brief introduction, everyone started find a corner of the room with a mirror to put on their makeup, which was made slightly challenging with the dim mood lighting of the room.

I brought a few outfits that day, but my best outfit was my New Look black off-shoulder bodycon dress. The other sisters also gave a nod of approval to this outfit

(The exact dress I wore in public the first time)

By the time we finished dressing, it was around 7pm at night. Unsure if we were going to go out dressed, we decided to order in a large pizza for dinner, but even though there were four of us, we couldn't even finish it. Maybe everyone was more in the mood to dress up and less interested in eating. Also, pizza really isn't the best type of food to eat if you want to keep you makeup intact.

After about an hour of chatting, the mood started to feel like we couldn't be cooped up in the room for another hour. After all, everyone was dolled up and it was a waste not to go out. Two of the girls were also really keen on going out in public to one of the LGBT bars to check out the halloween festivities. After a bit of internal debate, I too felt that halloween weekend was really the best time to go out crossdressed. Despite the dress showing my rather broad shoulders, I still felt quite passable that night (looking back at photos of that night...I think I have improved a lot since).

When we all stepped out of the room, my emotions were a heady mix of excitement and fear. I was out in public as a girl! Nevermind that it was just a hotel corridor. As a dragged my suitcase and glided down the hallway in my LBD and 4-inch heels, I felt like I was an air-stewardess who was just about to check out of her hotel. But I was also incredibly nervous, which made me glance down slightly and away when the hotel staff suddenly appeared in the hallway walking towards me. Being in public also made me hyper self-conscious; of how my hair was like, how I stood, where I placed my hands, the way I walked, etc. 

Fortunately, the lift lobby led directly to the carpark and within a few minutes we were all safely in my car. It was convenient since we didn't need to squeeze into a cab, which would have made me feel even more awkward. As my nerves calmed in the car, we set of to our intended destination, Tantric.

(Tantric bar. It was a bit emptier when we first arrived, but it gradually became this packed)

I parked in a nearby public carpark a short 50m away from the bar. But because it was my first time out, I had to steel myself for what felt like a really long distance to me. As I swung both legs out of the car and planted my heeled feet on the tarmac, it dawned on me that brisk walking was out of the question. Silently cursing my poor choice of shoes, I followed the lead of the other girls, teetering in my heels towards the club. The side walk was pretty narrow, so I pretend to look away or at my handphone when other people walked by in close proximity. Where were all the people in halloween costumes!? Everyone was dressed in very normal clothes. 

Finally, we reached the entrance of the bar. The bouncer was checking everyone's bag prior to entry. When it was my turn, the bouncer said "Miss, your bag please." OMG. It was the first time another person called me "Miss". Although I was pretty sure the bouncer knew I was a guy, I still felt super validated! It was awesome. I held up my black handbag (very feminine, yay), which he shone a torchlight in it before waving me in.

(Inside the bar. We were just sitting in one of those booths and I was just feeling perpetually self-concious)

At the bar, we found a booth with high chairs and sat down, before we each ordered an alcoholic drink. Even though we were in a safe space (it is an LGBT bar after all), because everyone looked so normal and I didn't see any other crossdressers around, I was just content hiding in my booth, trying to have a conversation with my sisters over the loud music. The only time I left my seat was to drop by the unisex loo (it felt so weird waiting for that ONE stall) together with other male customerd in the same tiny toilet. We ended up spending 90% of the time at the table pretending to be invisible and 10% of the time walking around trying to look for a more comfy place to hang out and talk. Not the most fun experience as far as trips to bars go.

As the bar became more crowded, we noticed more people in halloween costumes and a few drag queens in the bar who were slated to perform later in the night. A very friendly drag queen dressed head to toe as a cheetah (I think she is Dahlia Rose. I remember her huge gold choker with "Dahlia" on it. She looked absolutely regal in her outfit) saw us and started chatting with our timid group, complimenting me on my shoes, look and how she loves her "fishy girls". It was the first stamp of approval from an experienced drag performer, which made me rather happy. It was pretty nice to actually try socialise with someone in the bar. We hung around to chit chat a bit more, but eventually though it got really crowded and warm around midnight, so I decided to call it a night.


Parting Thoughts

Although the outing went pretty well, on hindsight, it was probably not too great an idea to meet a group of strangers for the first time in a hotel room. It's probably the only place most crossdressers can dress up safely, but in a different country other than Singapore, such a scenario could have gone horribly wrong. Even in Singapore, it is probably better to be safe than sorry too. I've since adopted the low-risk policy of not meeting other crossdressers I've never met before in hotel rooms.

That having said, I was pretty happy that I got dragged out of the room despite my initial fear and misgivings. Tantric was a safe space, and I should have been more daring whilst at the bar and chatted with others (or joined in with those who were dressed up), since it was Halloween and people were definitely less judgemental. Perhaps the next time when Covid-19 has blown over and Halloween comes around again, the mousey Isabelle will be no more; instead, reborn as the sultry vampiress 🤣

This is a post to any wife / girlfriend who stumbles onto my rather obscure blog (no no no please don't leave! I promise some insights!)

You're likely reading this post, because somehow you just found out that your Prince Charming actually prefers to be the princess, and life as you know it is crumbling before your eyes. There's a million questions in your mind and you're not sure if you know the answers to them. 

I will be upfront and tell you that your situation isn't unique, but it is undoubtedly  complicated. So let this fledgling blogger and life-long crossdresser attempt to answer your questions. Please note that these are all my opinions and I hope I do not inadvertantly offend anyone. If you want to read about my coming out story, you can find it here.


1) Why does my husband / boyfriend like to wear women's clothes? Is he a pervert?

No, your husband / boyfriend is not a pervert just because he likes to wear women's clothes! There are a myriad of reasons why men likes to wear ladies clothes and makeup to feel like a woman; some just want to look pretty, some do it as a form of escape, some want to destress, some are turned on by crossdressing, some view it as an expression of themselves, some just do it for fun to confuse people, while some are transgender. What is common is that crossdressers tend to experience the urge to do so from a very young age (around 10) and they have been doing so in secret because this behaviour is frowned upon.

Although crossdressing may be viewed as a perversion by some, it shouldn't be! Women crossdress all the time, by wearing clothes which are supposedly masculine, such as boyfriend shirts or pants, but don't get any flak for it. Society is still largely unable to accept why a man would want to degrade himself by putting on lacy undies and wear a dress.

Personally, I view crossdressing as a hobby like any other. It brings joy to the individual, there are amateurs and professionals in the field, and as long as it is not illegal, done obsessively or cause grievious hurt to others, it should not be seen in such a negative light as it is now. 


2) Is my husband / boyfriend gay?

It depends. Loving to crossdress and looking like a woman does not automatically make one gay. There are many crossdressers who are straight and cannot fathom to get it on with another guy. However, there is also a possibility that he is afraid of tell you of his interest in men, or he could be in denial of his sexuality.

Do consider broaching the topic gently to tease out an honest answer to your question. You need to be aware that there is a broad spectrum of sexualities and for your partner who has been a closet crossdresser since young with no one to talk to about his secret, it has been an extremely confusing journey.


3) Does he want to transition?

Probably not, if he says so explicitly. If your partner came clean to you about his crossdressing, it means that he wants to continue his relationship with you and has decided to confide in you in hopes of gaining your acceptance of his occasional crossdressing.

However, there is a possibility that he is so deep in denial that he does not realise that he is actually transgender at the point of coming out to you. Once he becomes more honest with himself, he may "come out" to you again some point in the future. It is important that you sit down with him and calmly understand his motivations for crossdressing. To be fair to yourself, if you are uncomfortable with your spouse transitioning, it should be made clear right from the start. 


4) Should I tell my best friend / relative about his behaviour?

NO! As much as you are emotionally hurt and feeling betrayed, telling a 3rd party about your husband / boyfriend's crossdressing has massive repercussions. Not everyone has the discipline to keep such a juicy secret under wraps and it can spread like wildfire. Society generally frowns upon a man in a dress; as such, crossdressing behaviour can potentially damage careers or wreck family relationships. Your husband / boyfriend may have struggled for years and finally decided to trust you with his deepest, darkest secret. It is only right to treat his confidence in you accordingly.
 
I repeat, please DO NOT spread his secret to 3rd parties.


5) He promises to throw away all his ladies clothes and never crossdress ever again

Unfortunately, that is a promise that he will not be able to keep. He probably said this in the heat of the moment, so as to stop you from crying/screaming at him/convince you not to leave him. He might be able to purge his ladies' clothes completely and bottle up his emotions and urges for weeks, months, even years. But all it takes is a trigger and his crossdressing will come back with a vengeance. It sucks for him because he is in a conundrum; he cannot dress openly or you will know he has broken his promise, which will shatter for a second time the illusion he had rebuilt. The only way is thus to do it in secret and hope you do not find out

Sorry fellow crossdressers. You all know this bit is true.


6) My Husband / Boyfriend is sending sexual messages OR took lewd photos of himself and sent them to other men!

This is a situation where I think there is a need to separate (i) the act of crossdressing and (ii) actions of infidelity. 

Although some religions may disagree, the act of crossdressing in itself is not wrong or harmful. It is simply wearing of clothes that are normally associated with the opposite gender. However, actions of infidelity wander into the realm of betrayal which I think should not be condoned. Yes, crossdressers can be sexually confused, but it is not an excuse to go around trying to hook up with other people when you are married / attached.


7) I am not a Lesbian. I cannot accept my Husband / Boyfriend looking like a woman

If your partner is a great person, is straight and dresses as a woman occasionally, you could consider setting ground rules such that you do not need to see him enfemme. It will be a compromise position, which is a win-win for both parties. He would appreciate your acceptance of his crossdressing and bring his crossdress into hiding, and you will not need to break the mental image of him as a masculine guy.

However, everyone is entitled to their opinions. If the mere thought of your partner wanting to crossdress repulses you so much that your normal life / love life is affected, perhaps it may be best for both parties to go separate ways.


8) I'm lost and afraid! What should I do?

Firstly, calm down and don't freak out. You are in a situation where the best course of action is to have a frank sit down talk just between your partner and yourself. It might be difficult and potentially long, but this is the only way to properly understand the situation. If you need some time and space to clear your thoughts, let him know.


9) Why is he telling me that he crossdresses? What does he want?

He is telling you because he is trusting you to keep his secret and hoping for some form of acceptance. To be able to crossdress freely, in the comfort of his home without the need to hide it from you. It may come as a shocker but chances are your partner is more terrified than you are. Remember that he has probably never told anyone his secret and is extremely worried about your reaction to him coming out, especially if you are married with children. 

You are under no obligation to accept his behaviour of course, but it is important to view it objectively. Just because he likes to wear silkier, lacy clothes at home does not make him a totally different person.


10) Are there questions I can ask my Husband / Boyfriend?

I think it is important to ask about his sexuality and whether he intends to transition. These are important issues that can be deal breakers for many relationships.

Ask about his crossdressing story. When did he start doing so, how did he start, why does he do it, where does he keep his ladies' clothes, whether he has gone out in public enfemme before, whether he has told anybody. You should also find out why he is choosing to share his secret with you.

If you're feeling bold, ask him to show you how he looks like enfemme. However, be careful not to mislead him into thinking that you are accepting his crossdressing if you feel otherwise. Honesty is the best policy, but the situation should be handled delicately.


End note

There are many articles and resources in the internet answering questions from distressed wives / girlfriends about their partner's crossdressing, especially on forums like reddit and quora. Do take what you read with a pinch of salt as everything is someone's opinion.

However, you can take some comfort in knowing that you are not alone in the world out there. And if your husband / boyfriend is an awesome person whom you want to spend your life with, accepting his crossdressing will definitely make him cherish you even more and enhance your relationship further.

Many have asked me about my coming out story. For those who don't know me, spoiler alert, the story has a happy ending. But perhaps it is more the process I went through which you might be interested in.


Why I U-turned and decided to tell my Wife

In an earlier post on my crossdressing journey, I wrote about how I had consigned myself to being in the closet for the rest of my life. Well, all that started to unravel after I married my wife and moved into our brand new flat. I gradually felt a sense of being boxed-in, due to a fear of my stash of women's clothes being discovered or my wife accidentally walking in on me crossdressed. I knew I was a bad liar and would be unable to talk myself out of a compromising situation, nor did I want to put myself in a position where I needed to lie directly to my wife's face. The feelings of mental claustrophobia was possibly exacerbated by a sudden drop in opportunities to crossdress secretly at night and release the pent up urges, since I now shared a room with my wife. Sooner or later, she was going to find out about my crossdressing habits.

Another factor that made me reconsider coming out was a possibility of success. My wife has a few close friends who were gay/lesbian. She wasn't religious, so she didn't subscribe to any potential anti-LGBTQ+ teachings. And she recently started watching copious amounts of RuPaul's Drag race (more for the drama than anything really). There was a sliver of hope that perhaps my wife would be at least grudgingly accepting of my crossdressing and I didn't need to constantly hide from her or live in fear of accidental discovery.

I decided I had to come clean to her. Honesty in a relationship is important, and if I had to face an enraged spouse, I rather control the parameters of the confrontation than be caught in an uncontrolled explosion.


Preparing for the Worst

My memory is a bit hazy, but I think it took me 1+ month of internal struggle on how to come out to my wife. Some of the rejected ideas along the way were as follows:

  • Wine and dine her, and when she's in a good mood, tell her - I rejected this idea because restaurants may be too noisy (can't talk in whispers) or quiet (awkward silences would be made worse), and an ugly fallout in public was a risk I didn't want to take
  • Dress up in women's clothes to show her - Mad ah! I immediately rejected this idea. Might work if you're the hilarious type
  • Leave out pieces of ladies' clothes for her to find - Too random. What if she doesn't find it when I want her to?
  • Test the water by casually chatting about crossdressing on TV and ease in the subject - It is a viable approach for some, but i felt it would be awkward for me to open with this
  • Sit her down after dinner / work at home and come clean - this was the most sensible, low risk option, but I was certain I would not be able to verbalise the complicated situation to her properly. I tried practicing alone in the car, saying: "I've got something important to tell you. I like wearing girl's clothes", but just the opening already came out very forced.

I finally decided to write a letter to her, because it would be clear and detailed. Writing the letter took me around 2 months, as I spent pockets of free time drafting and re-drafting to make sure the letter covered the main points: (i) What is crossdressing, why I do it and that I have been struggling with this since young, (ii) I'm not gay, I don't want to transition, (iii) apologise for not telling her before marriage, (iv) I hope for her acceptance.

To increase my chances of a less explosive situation, I was also selective of when to come out to her. I didn't want to choose to tell her after work on a weekday when she was tired and possibly still feeling the stress from work. I decided that the "auspicious" date had to be the 1st day of a long weekend. She would be more relaxed, and it would give her more time for the revelation to sink in and accept the situation. 

I nearly aborted my plan multiple times in the lead up to the date I selected. I feared for the permanent damage revealing my secret would do, the potential fallout and how things would go downhill in our relationship. Will she scream at me? Will she cry in sadness at having married a man that secretly liked being a woman? Will she tell her family / friends and result in even more embarressment? Will she ask for divorce and even use the crossdressing reason against me?

Scenarios of the potentially catastrophic fallout played back in my head repeatedly and I struggled to muster the courage to stick to the plan. I clung on to the little hope that somehow she would accept me.


The Bombshell


The bombshell finally dropped on 16 June 2018 and it marks a massive milestone in my life. Although I planned on revealing the secret on the first day of the long weekend, I chickened out from doing so. 

On the second day of a long weekend, I resolved to come out to the wife. To clear my head and relieve some of the tension, I went for a jog at 6.30am in the morning (it did help a fair bit). After I was done with my post-run shower, my wife had woken up and was using her phone in bed. I knew it was time. 

Sitting in the living room with the printed letter in hand, I sent her a Whatsapp message saying that I had something serious that I needed to talk to her about. By sending the message, I had just cut off all options of backing out. There was only one way out of this and it was forwards. My heart was pounding and I felt a pressure on my ears, like the sensation of the 4 walls closing in and being engulfed in terror. It felt like time stood still as I waited for the double blue tick in Whatsapp and for her to reply.

I heard a rustle in the room and my wife with her morning bed head stepped into the living room, looking worried. I sat her down, swallowed my fear, handed her the letter and said "Please read". And then silence.

After reading the 3 page letter, she looked at me and said "Is that it?"

(Me in response to my wife's reaction)

EH?!? I was stunned. Of the scenarios I conjured up in my head, this wasn't one of them. 

Seeing how much of a loss for words I was, my wife went on to explain that she was expecting something much worse, such as being in serious debt or being unceremoniously fired from my job. My feminine side and interest in crossdressing was indeed unexpected given how I was like in guy mode, but not unwelcome. She was also empathetic that I had struggled alone with the desire to crossdress since a young age, hiding my secret with no one to talk to. She said I did not have to hide in front of her anymore.

It was surreal. 

She was more accepting and understanding than I could have expected and ever hoped for. I don't cry easily, but I briefly did that day, hugging her petite frame as hard as one could.

My wife told me that she was very curious about how I managed to keep this secret so well hidden from everybody including herself and where I kept my ladies' clothes. 

I dug out the two wheely bins from the corners of our storeroom to show her my goodies. We sat in the corridoor of our flat, with me slowly unpacking and showing her all the items I had kept hidden, while she gave a running commentary on the style of each item. She was amazed at the height of the heels which I had (they were all 4-inch heels). She was slightly grossed out that I hadn't washed the clothes since buying them (understandably, since I had no place to dry them), so she offered to wash all of them (given that I had zero experience in dealing with bras and delicates). 

She set aside a small space in her cupboard for my makeup and told me to deliver any items I buy directly to our house instead of the nearby POPStation (mail pick up point). 

At that moment, I truly felt like the luckiest person in the world. A heavy weight lifted of my shoulders that day. I no longer needed to hide any more in my own home.


Minority amongst Minorities

I am acutely aware that I belong to a fortunate minority in the crossdressing community, whose wife accepts her husband's crossdressing. Numerous sisters have told me about how lucky I am. Most spouses are not so willing to bear with, let alone accept a husband's crossdressing. Some adopt an "out of sight, out of mind" stance, some grudgingly bear with it for the sake of their children, while others vehemently prohibit their husband from crossdressing. A number demand for divorce. I've even heard of an angry wife outing the husband to his family members.

For this I am extremely grateful to my wife. She wad under no obligation to accept my crossdressing, especially since I didn't tell her my secret before tying the knot. I love her prior to coming out, and her acceptance just me cherish her even more. 


End Notes

The last thing I want from sharing my story, is for you, the reader, to be green with envy, or despair at your current situation. I know everyone's situation is different, and coming out is not an option for many. But I do hope that my story inspires you in some way, or gives you faith that even if you haven't found them, there are people out there who will accept you for who you are; that you are normal in their eyes, that your female self and male self are essentially the same person, only that one is a lot more fashionable and fabulous than the other 😁

If you are a girlfriend or spouse who just found out about your partner's secret, I wrote a post about some key things you may want to know.

With the internet at our fingertips, there is a wealth of information on transgender issues, gender dysphoria, challenges of being transgender, how to present oneself as female, youtube videos on makeup and crossdressing, etc, which makes it easier to "level up" and be more knowledgeable about the subject. Most of these are generic and applicable regardless of which country one is in. Resources in the English language however, tend to be be largely originating from the US or the UK, which also meant that the struggles or coming out experiences were in the context of their society.

It meant that it was hard to read or hear the struggles or coming out experiences in a local context. To make matters worse, crossdressers who don't identify as transsexual (i.e. don't intend to transition) form an even smaller slice of the transgender pie. The majority are usually so deep in the closet no one knows about them (I know, I used to be one).

As expected, resources on crossdressing in a local context (Singapore / Malaysia) are extremely sparse. Search "Singapore Crossdresser" on Google and the top few results are about dating crossdressers, news reports of crossdressers being arrested for some crime, or some porn site (Don't get me wrong, I've got nothing against porn). It is really not difficult to understand why crossdressers are very easily viewed by society as perverts or deviants (fortunately, there is always Wikipedia, a very neutral and informative, if not overwhelming source of info)

There used to be a forum called SGButterfly, which I understand that in its hey day, was an active online platform and safe space for exchange of information and experiences between CDs/TS both mtf and ftm. It has unfortunately been shut down, but we've got to accept that forums are a medium of the past. In its place there are facebook groups for crossdressers, but these tend to contain superficial content (i.e. posting of photographs)

I hope this blog on my crossdressing journey and answers to common questions serves as a decent guide to some of you readers. 

As an easy reference, I also list some of the local resources on crossdressers (and some transgender) that I have come across in the past.

Blogs & Articles:
(Updated as of 17 Nov 2022)
  • Gin Kim's Blog
  • Kim-Ann's Quora(she was known as Em Chan)
  • Dreamin Asa
  • Francesca's Blog - Guide to storage solutions for Singaporean CDs (Part 1, Part 2, Part 3)
  • Charlotte Chronicle
  • Not so secret life of crossplayers
  • Cosplayers in Drag
  • My name is Veron: Struggle of being a Malay-Muslim drag queen
  • Blurring the Lines
  • Account of a married crossdresser / transgender on Women's Weekly magazine
  • Reflections of an Intellectual Crossdresser (A great blog by a crossdresser in NZ. I find her posts to be very well written and articulated. Very useful)
  • A Beginner's Guide to Crossdressing (A pretty good resource by US blogger Hannah McKnight)
  • Gender Dysphoria Bible (Very detailed and well written resource on Gender Dysphoria. Not local, but too good not to include)
  • Transgender.sg (Site has a lot of good explanations)
  • How does crossdressing feel? (Fantastic answer on Quora by Em Chan)
  • When Daddy becomes Mummy
  • Price of being Queer in Singapore
  • Trans people actually don't have time to disrupt the social fabric (not CD, but it is a good article)
  • Enfemmestyle (not a local site, but there's a lot of short articles for CDs)
  • Breastplate FAQ (very detailed post by Janna, a crossdresser in the USA)

Youtube:
  • Ask Me Anything - Crossdresser (Interview which I took part in)
  • Confessions of Singapore's Crossplayers
  • Interesting interview of local transwoman Aerie Rei - (Part 1, Part 2, Part 3)
  • I crossdress (short interview with 2 malaysian crossdressers)
  • Spinvestigators - Crossdressing in Singapore
  • Quen's journey: Being Transgender in Singapore
  • My Life as a Transgender University Student (in Singapore)

I will update this post if I do chance upon relevant articles or videos. If you do know of any, do share and I can add them to this list
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