Musings of a Singaporean Transgender: Dressing in Public

The last time I went out in public properly as Isabelle was in April 2023 for Cosfest at Gardens by the Bay. A month later my egg cracked and I started HRT. Since then I've not been in the proper headspace to go out in public as Isabelle. While I did dress up as Isabelle in a private indoor space, I felt incredibly dysphoric about my appearance when I dressed. Gone was the confident Isabelle, replaced with a terribly brainwormed baby-trans. I hated all photos I took of myself, nitpicking every masculine facial feature. I felt like a fraud; a man in a dress, unpassable even with makeup, let alone with a bareface. I stopped dressing up, partly because I was living with parents and didn't have a safe space to transform into Isabelle, mostly because it was just too painful to see that my best efforts fall short of the passing mark.

I could not see myself as a woman. Fighting inner demons on a near daily basis, I was constantly worried about whether my hair would grow out properly, impatient about the effects of HRT and facial hair removal, constantly anxious that even after waiting for a few years, I would still be unable pass. Never mind the fact that when I went out as Isabelle during my crossdressing days, I was able to try on clothes in women's changing rooms and navigate through a mall without too many quizzical stares. My brain felt a bit broken.

But as my hair grew out slowly, I could occasionally see glimpses of the woman I would become. Though I was still sporting a mullet because my fringe wasn't long enough, I felt that maybe, just maybe, Isabelle was ready to make a reappearance, this time without needing to wear a wig. Coming out to my hairdresser and having her reassure me that my hair could work despite my fringe was the validation I needed. Since renovation of my new home was also recently completed, I decided it was time to stop hiding in my shell, driving myself insane by constantly worrying I wasn't going my own expectations. If I was going to present female 24/7, I needed to get used to weird stares and uncomfortable comments from others. I decided to dress up as Isabelle for my voice therapy session and shopping at Somerset.

On the day I was supposed to go out, there was an unexpected hiccup that nearly derailed my plans, because my kid suddenly complained of pains in both her calves to the point where she didn't want to walk. It was quite worrying so I brought her to see the doctor, who did a check and reassured that it wasn't anything to be too worried about. I enjoyed a McDonald's breakfast with the kiddo before dropping her off with my Mum for the day. It was time to let Isabelle out.

I hadn't put on makeup in almost a year, but it was muscle memory at this stage and came back to me rather easily. An hour later, the familiar, dolled-up version of myself reflected back in the mirror. The flaws were still there, but all in all, I didn't look too shabby. I felt brave enough to go out as Isabelle once again. For the day I had picked out a ribbon-tie sleeveless green maxi dress with a floral design. It was dressy enough for a shopping outing but not too formal for wearing in Singapore.

It was the first time I dressed as Isabelle without a wig and holy hell was it such freedom! I wasn't sweating buckets in Singapore's humidity, there was no wig cap constricting my head like Sun Wu Kong's golden headband and I didn't need to worry about flyaway fringes. It was a good start even before I stepped out of the house.

The first stop was my voice therapy appointment at Alexandra Hospital. I look forward to these sessions because the voice therapist I work with is incredibly encouraging. It is also a safe space for me to practice my female voice (which is still terrible and needs a lot more practice in my opinion). As I peeked through the door of the clinic, the voice therapist stared at me quizically for 5 seconds before bursting out laughing: "Omg Isabelle I couldn't recognise you, I thought it was someone who got lost!". We started chatting, updating each other on the things that transpired over the past 5 months and did a few voice/video recordings. I'm not sure why, but she was convinced that while my pitch wasn't high, my voice worked really well with my feminine appearance and wanted to graduate me from her voice therapy sessions (Nooooooooo!). Fortunately I convinced her to give me one more voice therapy session in June.

I went on to meet friends in Somerset for sushi dinner and shopping. Being dressed as Isabelle made me put in the effort to use my female voice more, which I was able to do so for most of the night 😁 We went to the usual hits; Love Bonito, Mango, Zara, Playdress and Pomelo before grabbing bubble tea to round off the night.

Unlike the early days of my crossdressing journey that were primary filled with excitement and euphoria, there was instead a huge sense of freedom and calm this time. I didn't worry about my wig looking out of place (and therefore fake). I somehow didn't get stares despite the Friday night dinner crowds. I felt like I blended in well; just a regular gal out shopping with her friends.

I could use such feeling of calm and happiness more regularly.

(Some days, it just feels like we have Dune-sized brainworms)

Brainworms. I only recently learned about this term. While urban dictionary defines it as "cognitively degenerating" or "going off the deep-end", the way it is used by younger generation transgender folks seems to be to have an illogical, unjustified belief that one is unpassable, despite evidence otherwise. "Brainworms" is a catchy and an easy way to describe the thoughts of self-doubt that even the most passable crossdressers and transgender have. Taken to the extreme, it might push some to go for surgery after surgery, to correct the "flaws" or masculine markers that one perceives. We regularly jest with each other that it isn't just HRT that is needed, but a thorough regime of deworming.

I've been having a bad case of passability brainworms recently. Catching a glance of my furrowed brows in the mirror, I think about my browbone being overly prominent. The toilet downlight casting an unflattering light on my face, accentuating all acne scars and my angular jaw makes me feel annoyed. In my quiet moments, I think about the genetically gifted, youthful transwomen that I will never measure up to, and I regularly worry about my ability to pass without makeup or surgery. It takes good friends to bonk me on the head and bring me back to earth again. But the cycle repeats, to the point where I already feel "paiseh" for voicing the same concerns to the same group of friends.

I believe there are two phases to the bad case of brainworms. The first is before/during the transition phase, when there is uncertainty associated with transitioning and constant worry of how the future in 2 to 3 years time will look like. I can't speak for early transitioners, but I'm sure for those transitioning in their 30s or later, the need to tear down work/life/social structures built up over decades makes the brainworms especially numerous and wriggly. This is where I am right now, where I keep seeing an uncle in the mirror and cannot envision how the future will be; whether HRT will allow me to come closer to my appearance goals, whether growing out my hair is even possible, whether I could look decently female without a full face of makeup.

Someone shared the photo below, which I thought was rather apt. The changes associated with transitioning such as fat distribution, electrolysis and hair growth takes time, so it is important to be patient. Even non-bodily changes such as developing a style that suits us, gender-aligned mannerisms and voice training isn't achieved in a few months.

(Please don't say "Yassss Kween" 😖)

The second phase is after transition. There are certain physical traits that do not change due to HRT, which can continue to be a source of some dysphoria. Height, size of ribcage (which results in a strong looking back), size of hands and feet, lack of hips, etc, the list goes on. While they don't create mental discomfort as regularly, society has a way of bringing typically dormant dysphoria to the fore, be it intentionally or unknowingly. There's always some random ass***e who points out that you are using the wrong toilet. Or an accidental misgendering by a stranger even though you felt extra passable that day. The reality for most transgender folks is that regardless of how "successful" one gets, there are always days where the brainworms come out to play.

(That said. I do wonder if the most successful Transgender beauty queens like Yoshi Rinrada even have such concerns. For them, perhaps it is about maintaining their youth/beauty in the highly competitive space, rather than passability concerns. Because come on. Look at her).

Life is less stressful if we stop caring about what other people think of us and live the lives we want to. Might explain why uncles over the age of 60 look chill, since they just don't give a f*** about what anyone thinks. It's easier said than done of course, but definitely something to work on.

Gender dysphoria is a battle that is largely fought alone, so when they take the form of wriggly brainworms, we just have to treat them like every other problem we face in our daily lives; try out best to beat them with a stick and soldier on.

(The Awkward Yeti, delivering real life comics, as always)

(Yes, I'm a beardy man almost all of the time, No, I sadly do not have glorious hair like him)

This post is more of a life status update rather than dressing up as Isabelle, but I've been putting out so little content on my blog I'm feeling ashamed from the neglect. I rarely dress up these days because life gets in the way, and with the latest events I find my free time and energy dwindling to a trickle. Such is the life of a working parent in Singapore.

After living in my current place for 5+ years, the wife and I decided that it was time to sell the place. While we do love our 3-room flat, its status as a weekend home after our kid came out made us reconsider our needs. We wanted to move nearer my parents so that we could stop "booking-out" from my parents' home on Fridays to stay at our own place on weekends and "booking-in" on Sundays. The back and forth travelling finally wore us down after years of doing so. With home prices at all time highs, we decided it was an opportune time to cash out and wait for a good unit to be listed on the market. After multiple viewings by prospective buyers over a 4 month period, we finally had an offer and inked the sale.

So I am now in the middle of throwing, sorting and packing my stuff into boxes. And damn, do I have a lot of crap for a 3-room flat. People, stop buying stuff on whim that you don't need. They just take up space and collect dust, only for you to throw it out when you move out of your house. I made a promise to myself that I will keep myself in check, even if I have a bigger space (heck no. ESPECIALLY if I have a bigger space).

I won't be able to dress up as Isabelle until I get my own place, so all her stuff had to be put into cold store once again (the last time was just before my kid was born). Through packing, I realised that I bought way too many things over the years. After picking out 20 outfits to give away, I still had 1 full suitcase and 2 vacuum bags (70cm x 45cm) squeezed to the brim. I'm proud to say that since my last blog post, I've not bought a single item for Isabelle. Let's see how long I can keep that up.

There's a tinge of sadness about moving out from the place I've called home for more than half a decade. After all, it was the warm, cozy abode where we rested and relaxed. We had fantastic, friendly neighbours that made the living environment even better. Home was the safe haven where Isabelle could doll up each time without worry of judgement, which allowed her to gradually blossom. But this is life. We savour moments past, both happy and sad, before moving on to the next phase of life, hoping with a tinge of excitement in our hearts that change would bring us joy and more memories to come.

I wrote about my abject dislike of facial hair previously as it really got in the way of presenting female. Shaving doesn't work for me since the stubble remains very visible under my makeup. My go to method to get a very clean look is to pluck the hairs out one by one using tweezers, but not only is it painful, can only be done if the hairs are long enough, but it also takes a good 1+ hour in front of the mirror. This meant that I had to plan my facial hair growth if I wanted to dress up. Absolutely effin annoying.

I had been considering permanent hair removal but I wasn't too willing to spend the money. It was only this year that my annoyance of facial hair plucking boiled over and I decided to just get it over and done with. After all, what was the point of working so hard if I was just going to hoard money in my bank account.

There are 3 main forms of hair removal out there. Intense pulse light (IPL), laser and electrolysis. In Singapore there is a preference for IPL or laser, as it hits a much larger area within a short span of time. Both technologies are also more effective for chinese who have black hair against fairer skin. Apparently the efficacy of hair removal is reduce for people with fairer hair or darker skin. However, I also read that the effects may not be permanent, especially for facial hair. The thought of spending thousands of dollars, only for the hair to grow back a few years later wasn't appealing. I wanted something permanent. So I decided I had to go for eletrolysis.

Unlike IPL and laser, electrolysis isn't too commonly provided in Singapore and for good reason. Electrolysis targets each hair individually, meaning that it takes significantly longer than the other two technologies. It is done by inserting a hollow probe into the hair follicle, introducing heat to kill the hair follicle, before the hair is then tweezed out. The cycle then repeats for hair in the target area. The time taken to do a full clearance of facial hair depends on how hairy a person is. I heard that HairFreeSG was pretty decent for electrolysis so I decided to do a prelim consult. It was estimated that I would need around 20 to 30 hours to permanently removal all of my facial hair, which translates to an expense of around 2.3k to 3+k. It wasn't cheap, but I really hated my facial hair so I decided to stop being a cheapo and begin my permanent hair removal journey.

The electrolysis session starts of with application of numbing cream on the areas to be treated and having said areas wrapped in cling film (probably to avoid accidentally wiping off the cream). I had to wait around for an hour before the actual electrolysis session. In the well air-conditioned room, I lay on my back while the electrologist with her special magnifying spectacles painstakingly zapped my face hair follicle by hair follicle.

Readers will be wondering, does electrolysis hurt? Well the numbing cream definitely did help make it quite bearable, so for cheeks and chin I'd say it is pretty ok, perhaps 2.5/10? The neck and upper lip area however is another animal. My oh my. I had to grit my teeth through the pain as the electrologist did her work. On the pain scale, 5/10? (Ahah I don't know what this arbitrary scale is. Maybe 10/10 is "Give me an epidural you monster!") I can't say that it is unexpected though. When I dehaired prior to a dress up session, plucking the hairs on my upper lip always hurt a lot more.

While the length of each electrolysis session is up to the individual's pain tolerance, I was recommended to cap it around 1.5 hours, since clearing the entire face at one go might result in a fair bit of swelling that is obvious. However I didn't want to make so many trips to the studio and I wanted a full clearing ASAP, so for my second session I decided to go for two 1.5 hour blocks with a rest period in between for myself. The studio has a team of electrologists so they can take turns if necessary.

For those worried about recovery, at the end of 3 hour session there was some swelling at the treated areas and it definitely looked like I had a strange sunburn on my face and some peeling skin that lasted for 3 days. I was also advised not to shave my face, as my skin was sensitive and razor blades might introduce bacteria that cause infections. So if you're thinking of going for electrolysis as well, do plan a bit if you might get queried on why your face has red patches/slightly swollen. Fortunately for me, only my wife and another friend asked about my patchy face.

At the point of posting this, I've done around 4 hours of electrolysis and yet to do a full clearance 😫 I estimate that I need another 1.5 hours to achieve that, after which the hairs should grow back a bit finer (hopefully some don't grow back at all). I find a massive irony for us guys who like to present female. We've got facial hair on the bottom of our faces which we don't want, but when it comes to wanting to grow a luscious head of hair, it may be impossible due to receding hairlines as we grow older. So we spend money, time and sweat to removing hair from one part of the face and even more money to transplant hair on another. Wanting to present female is bloody darn expensive.

<Update>: As of 1 May 2024, I have gone for around 30+ hours of electrolysis. My facial hairs are finer and the time taken for a full clearance by the electrologist is around 1.5 hours currently. While this is an improvement from before, it is longer than I had hoped for. Unfortunately, permanent hair removal takes time so I just have to keep going for sessions diligently every 2 to 3 weeks. Hopefully 60 hours is enough to finally rid myself of facial hair.

The first cosplay event I attended was AFA 2022, which I did so as a bucket list item. Though I felt quite a bit too old to cosplay, I had some fun in that event. A few friends in the crossdressing community were also itching to attend a cosplay event as they have not done it before, so their egging also made me decide that I had to give cosplay another shot. After all, cosplay was also an opportunity to dress up in fancy outfits to take photos, which was totally up my alley.

We decided to attend Cosfest 2023, which was going to be held in Gardens By the Bay (GBB) to coincide with the final week of the Sakura theme. For those who don't know, GBB has fixed themes every year, of which the shortest but most popular one is the Sakura theme. The flower dome will display real Sakura flowers in bloom and the decors will be decidedly Japanese. During the school holiday weekend this year, there was also a Pikachu mascot dance where 3 cotton candy haired Pikachus made a brief appearance.

I always wanted to cosplay as 2B from the game Nier Automata since I felt I could pull the character off and I already have the wig, but it seemed mismatched with GBB's theme which calls for a kimono (I realised post-event that 2B has a kimono outfit, but it's black so once again, not so matching). Two crossdresser friends were keen on going as Raiden from the game Genshin Impact, so after some consideration, I decided to go as Yae Miko! Yes, I'm cosplaying another pink haired fox spirit, but it's a cute look so what the hell.

The real reason that was holding me back from cosplaying as Yae Miko was the price of the outfit. Cosplays outfits are not cheap and perhaps due to their popularity or complicated looks, outfits for Genshin characters are bloody expensive, with the cheapest shops selling them for around $80 and the premium ones going as high as $200! For an outfit I wasn't going to wear very often, the ROI did not make sense. That said, when my female self wants something pretty, she gets something pretty....so I finally decided to buy the Yae Miko costume from a Taobao shop called 1/3 delusion. When it was delivered, I could tell that the material was more premium that your usual Taobao shop. Sadly there were noticeable defects that I would consider to be poor workmanship and unacceptable for such a price. It was still wearable and good enough for photographs and I received the outfit too near the event date so shipping it back for a refund or exchange was out of the question. One thing for sure is that I'm going to milk this cosplay as much as I can.

Yae Miko's makeup was simple enough; pink eyeshadow and blush, a well drawn eyeliner and a light red lipstick. What was challenging was her hair, which required styling the wig with the right amount of kinks, something I've never done before. I wanted to get the character right, so after a few Youtube videos, 2 hours of combing, hairspray and styling, I ended up with a wig that was...passable for a first time attempt. I understood why some cosplayers I follow on Instagram complain about wig styling; it is so time-consuming, yet absolutely essential if you want your character to really look polished and as close to the Anime or Manga.

Cosfest was on a Saturday so I had to dress up and leave the house before 9.30am, which was around the time my kid wakes up. This is so that my kid will not see me dressed as Isabelle and be confused as to why Daddy is dressed like a woman. To meet this hard deadline, I woke up at 5am to prepare, such as moving all my gear to the car, eating a heavy breakfast, showering, make-up and dressing up). Even with the really early morning, I only managed to step out of the house at 9.40am (can you believe it. 4.5 hours just to prepare). Fortunately my kid was still happily sleeping in for the weekend.

I reached GBB at 10am, a good two hours before the event so I was the ONLY cosplayer as far as the eye could see. The morning crowd at GBB were primarily made up of families and I could feel every single eyeball staring at me as I walked from the carpark to the entrance of the flower dome as Yae Miko. If it was my first time crossdressing in public, I'd have died of embarrassment and made a beeline back home. But it wasn't so I just ignored the stares and carried on walking, confident of how I look.

I was already feeling quite warm under the sheltered walkway, so I went directly into the flower dome to enjoy the best thing there; the cool temperate feel from the dome's powerful air-conditioner. Without it, cosplaying would be quite unbearable. The dome was still relatively peaceful and uncrowded in the morning as the travel buses full of tourists had yet to arrive. I brought my tripod along hoping to take some photos by myself, but there were already signs prohibiting the deployment of tripods, so I ended up just walking around the dome and waiting for my friends to arrive.

Two incidents at cosfest made me feel extra validated and really happy. I was sitting under tall trees in the dome to rest my feet when a pair of young cosplayers came up to me. I thought they needed help to take a photo, but it turned out that they wanted a photo with me as they felt my Yae Miko looked good. One of them also complimented my makeup, which made this Yae go "Yay!" inside😏. The second incident was when I walked to meet a friend in the queue to collect cosfest tickets to enter the flower field hall. I caught a glimpse of 3 chinese teenage girls eyeballing me and one of them gushing about the Yae Miko character and my cosplay. My friend was just queued up a few metres behind the group and when I spoke, I also saw the sheer surprise in the ladies' faces that I was actually a guy. Later when we were wandering around the flower dome, the chinese girl who had been gushing about Yae Miko earlier came up to me to tell me how much she loved my cosplay and was really happy to see me again so she could take a photo with me. To be frank I was quite surprised as she was really pretty and would clearly make a much better Yae Miko if she decided to cosplay. But her reaction just meant I was doing something right. It was the best moment of the day and made me really happy. I swear, compliments and validation from cis-women are truly the best. Just keep em' coming.

(Isabelle as Yae Miko under the Tori, almost as though I'm in Japan. Not too shabby for a 1st attempt!)

Yae Miko's outfit is a backless halter top so I did not want to wear a bra as it would show. I was hoping that my adhesive forms would stick to my chest properly through the entire day as they were new and the adhesive was still quite sticky...well unfortunately they did not🙄. When I got too sweaty, the forms would detach and slide down to my waist (held up by the obi), resulting in a very weird look. I ended up visiting the toilet multiple times in the day just to wipe off my chest sweat and to adjust the positioning of the forms. Very annoying and something that needs to be sorted out the next time I cosplay.

(Yae Miko from Genshin Impact. Apparently she's hiao and a tease. Kind of like me😝)

I finally linked up with all the remaining crossdressers around 1pm and we made our way gradually through the dome as a group, dressed as Yae Miko, Raiden, Yelan and Saber. I'd say that for a bunch of guys, we cleaned up and presented as women decently, but walking in a group of 4 attracted a ton of attention. As we strolled down the winding path of the flower dome, we were frequently stopped by random tourists asking for a photo, which we obliged. I was the only one who attended such an event in cosplay previously, so kudos to the rest of the gals for being such great sport and not freaking out when others asked for photos.

We parked ourselves at the junction near the flower field hall and where the main Sakura and Japanese theme displays were at, chatting with each other and taking the occasional photograph. But after a while we noticed that because of our position and how we naturally stood out, we kept getting approached for photos. There was a point when a continuous stream of tourists and locals came up to us to take photographs. Most were really nice about it, appearing genuinely interested and excited to take photos with us. But some were quite rude, snapping photos without asking for permission. I think the worst offender was an auntie tourist from Russia or one of the Baltic States who casually said "Oh these are the ladyboys" to me and a friend, which pissed me off a bit. But by then I was too tired to argue or make a scene, especially with a tourist.

The rest of the day was spent flitting in and out of the flower dome, linking up with other friends to take photos. The crowds started to throng and by 2pm the outside of the flower dome was jam packed with cosplayers, photographers, tourists and regular families, all the way to the ticketing counter. If I had to compare it with AFA 2022, I think Cosfest was worse because of the lack of air-conditioning in the "free" section (i.e. outside the dome).

My friend and I decided it was time to call it quits around 3.30pm because it got stupidly crowded and we were both quite tired from walking around in the humidity. My overly tight wig cap was also giving me a bad headache and I was all ready to ditch the kimono for my regular uncle clothes. I couldn't de-drag at home since my kid was around and my wife had friends over to help with the babysitting, so I drove to GBB's Bayfront plaza carpark to use the handicapped toilet. The carpark was a lot more secluded so I didn't have to worry about hogging the toilet while a wheelchair bound or elderly person was stuck outside waiting for me. Just like Cinderella at the stroke of midnight, I quickly transformed back into my male self and headed home to my regular Dad duties.

Some post-cosplay event musings:

1) For 1st time crossdressers, choosing a cosplay event as your 1st time in public is going to be scary AF due to the sheer number of people, but because everyone is dressed up, there's little judgement passed (unlike going to a mall crossdressed) and the shock to your system actually can help you gain confidence very quickly. But you've got to turn up in cosplay.

2) Having a ton of people asking for photos is pretty darn tiring. But compliments from cis-women? Keep them cominggg 🥰

3) I'm at the age where I'm really not interested in merchandise, be it cute anime collectable or art. They're nice but I've zero attachment to anime or manga, so buying convention tickets is quite a waste of money

4) I definitely need to redo my Yae Miko outfit. The photos turned out great, but there's still room for improvement, such as getting the obi to fit properly, getting the forms to stay properly on my chest, making sure the ear attachments can stay on, etc

5) Battery operated fans are a godsend if cosplaying in places with no air-conditioning. Experienced cosplay photographers will carry some of these around to help make the heat more bearable for their models

6) I need to remember to ask others to help me take more photographs and also try to make more friends in the cosplay community. I took a grand total of 27 photos using the DSLR that I was lugging around for 5 hours. Quite a waste

Although Cosfest at GBB was insanely crowded and the humidity was an absolute killer, I had a pretty good time. So I foresee myself turning up in cosplay once again. AFA 2023, I'm coming for you!

Back in 2019 I attended my first large scale gathering of crossdressers in Kuala Lumpur, Malaysia. Jointly organised by Malaysian and Singaporean friends, it was the annual bilat event that sees attendance of 40+ crossdressers from both sides of the causeway, all dolled up to the nines. I made some good friends in the community whom I've continued to chat with regularly despite having only met them once during that gathering. Due to covid, work and life, I've never been able to join subsequent gatherings since, so when the opportunity for a 3D3N solo trip came along I decided to head to Kuala Lumpur once again to meet with old friends (sanctioned by the Wife of course. She called it my "Eat, Pray, Love" trip. Not the right reference, but it was a movie about a solo trip of self-discovery).

I planned for my 1st night to be at a fancier hotel so I could do an indoor photoshoot in a nicer setting, while the remaining nights were at a budget friendly hotel within walking distance of the major shopping areas.

Day 1 - Photography

Being mindful of the potential checkpoint jam due to the long weekend and not wanting to waste any time, I began my drive towards Kuala Lumpur at 5.30am. I cleared both border customs in record time of 15 minutes, which was very shocking as that has never happened in any of my trips to Malaysia (perhaps going in early is the way to go). Stopping only for a coffee and toilet break, I reached my first Kuala Lumpur hotel at 10.30am. Fortunately they had an available room so I got to check in super early. The hotel was located in the city fringes so there weren't too many sights for me to explore which was fine since my primary objective was to take fancy photographs within the hotel. After a quick lunch and nap, I ditched my male trappings and began the transformation into Isabelle.

Self-portraiture using a DSLR on a tripod and flash photography isn't the easiest thing to do. Not only do I need to do my own makeup, I have to set up my photography equipment, use my handphone as a timed wireless-tether to trigger the camera shutter, while being the model being photographed. This is something I do regularly at home and they tend to be long drawn 4 to 5 hours events with around 200 photographs taken. And this was exactly what I did at the hotel. I started at around 4.30pm and after multiple outfit and position changes in the room, I finally called it quits at 11.30pm as I was too hungry and tired to continue. By the time I changed back to my guy mode, ate my cup noodles for dinner and rolled into bed for that sweet glorious sleep, it was already 2am. Was it worth it? Definitely. You be the judge.

(The dress I was going to wear for New Year's Eve. Photo taken of me from behind)

Day 2 - New Year's Eve

I originally planned to wake up early for a morning photoshoot by the hotel pool in a bikini (which would have been awesome), but there was no way in hell my middle-aged body was going to survive another day with 4 hours of sleep. So I opted for a late morning lazy breakfast, before I checked out of the fancy hotel and headed into central Kuala Lumpur. The second hotel was unable to cater for an early check-in, so I spent a bit of time wandering around Lot 10 and Pavilion mall to suss out the shops and potential places Isabelle could go shopping on the 3rd day. The latter had a Parkson Elite with a huge array of fancy dresses and cheongsams so that would be my go to. Day 2 however, was New Year's Eve and the main event.

My friends had pre-booked a small table in a club/bar from 8pm till late. Events like this are hard to come by for us crossdressers, so looking like a million bucks was an absolute must. After nearly 2 hours of makeup, accessorising, sticking on fake nails and slinking into a sliver sequined mini-dress, I stepped out into the hotel lobby feeling like an absolute Queen.

I linked up with my friend and we headed over to the bar. Tapping on a nondescript door that looked like a maintenance access, it opened to reveal a fancy corridor that led to a swanky looking venue. I never understood the concept of a speakeasy, but I suppose some do enjoy the feeling of exclusivity. Also, this place was LGBT friendly, so being a speakeasy was probably a slight benefit in the more conservative Malaysia.

And so the night began! My guy self might be a homebody, but Isabelle...she loved looking glam and she loved the night life. There was a live band with a male lead singer who sang many suspiciously closet gay songs (there was George Michael - Careless Whisper, Lady Gaga - Bad Romance, Cher - Do you Believe). The food was surprisingly tasty for a bar so we stuffed our faces with food to hit the minimum spend (rather than drink ourselves silly).

(Look at this fancy cocktail!)

As we enjoyed the music, food and vibes in the bar, we chatted like a bunch of old friends, despite it being the second time we've met each other. We spoke of how life was treating us, of other crossdressers old and new, of future gathering plans, of the scary but heady experience of coming out to cis-gendered friends, etc. And before we knew it, we started the final countdown to the new year, which was capped off with a bang by a cabaret show (Nicki Minaj/Ariana/Jessie J's Bang Bang really riled the crowd up). The DJ started playing clubbing music and people began dancing in front of the stage with the cabaret performers and each other. Isabelle couldn't help but join the crowd on the dance floor, jiving and moving with revellers. We finally decided we had our fill of fun at 2am, bade each other farewell, Happy New Year and parted ways.

Day 3 - Shopping

The 3rd day was considerably uneventful as it was a dedicated shop/eat/relax day. I didn't remove my red stick-on nails when I went for breakfast at the hotel in guy mode, so I got a number of stares from other guests sitting near me as I ate my nasi lemak. This was the first time I ever did something this bold, but I didn't care or feel nervous about it. The beauty of a being in a foreign country is that I will never meet any of these people in my regular life and there is very low chance of meeting someone who might recognise me.

For my casual shopping trip, I chose to wear a recently purchased black denim babydoll dress that came up to mid-thigh, a style that is pretty popular recently in Singapore and very suited for shorter crossdressers like me. One thing I noticed was that a lot of people still wore masks in Kuala Lumpur despite the Covid pandemic being largely over (perhaps around 70%?). So in order to blend in I also decided to wear a mask when wandering around Pavilion mall.

(Definitely not my best mirror selfie, but the only one I took that day)

I was still feeling tired from the earlier two days, so there wasn't a huge motivation to go crazy shopping. Plus the public holiday weekend crowd also sapped my energy a bit (I dislike crowds). So I zoomed in on my main objective of cheongsam shopping...which unfortunately reminded me of how unforgiving cheongsams are. A perfectly tailored cheongsam on a lady looks incredible; poised, classy and shows off womanly curves (just look at Maggie Cheung from the movie "In the Mood for Love"). But with the wrong material, design or cut, it is so very easy to look matronly, too top heavy, or *gasps in horror* like a Bak-zhang (Hokkien for rice dumpling. Looking like one means looking swollen with all the meat and fats wrapped too tightly) I'm quite slim and have decent curves with help from my hippads, but none of the cheongsams I picked made the cut. Also, they all cost $100 and there was no way I was going to spend that amount of money unless I was going to look a smashing 10/10.

(The tasty tasty Bak-Zhang. But eat too many and you'll start to look like one)

By 5pm, I was utterly drained and decided it was time for Cinderella to finally transform back into a fella for good. After a simple dinner, I met up with my friend again and ended the day with another chit chat (this time we were both in potato mode) over a milkshake from Five Guys.

Wrap Up

My 3 day solo holiday to Kuala Lumpur was the longest consecutive period I have spent as Isabelle (which also included sleeping in nighties that I brought for the trip). Though it was quite tiring due to me being overly ambitious, I thoroughly enjoyed myself. I've always wanted to celebrate New Year's Eve in a sequined dress as Isabelle and I did exactly that, checking off another item on my bucket list. I'm not sure if I will get another opportunity to attend the next annual crossdressers gathering or go overseas dressed as Isabelle, but I'll make a wee bit of effort to see if my schedule (and life) allows me to. In the mean time, I'll need to think of more things to add into my significantly shortened bucket list.

Covid had put a huge damper on events in Singapore since 2020. No festivals, no celebrations, no conventions. With almost all restrictions lifted in 2022, cosplayers started coming out of the woodwork to gather and go for events. And the biggest Anime and cosplay event of the year was the 3 day Anime Festival Asia (AFA) held at Suntec City Convention Centre.

Attending a cosplay event has been something on my bucket list, so with a bit of YOLO in my heart, I decided I had to attend AFA 2022. I dipped my toe into cosplay a few years ago by buying an outfit from Taobao purely for the fun of it. After looking at multiple choices online and eliminating those which revealed too much skin, required too much booba or had hem lengths so short nothing would be left to the imagination, I finally decided on a maid outfit of Tamamo no Mae, a kitsune (fox) spirit from the once popular game Fate Grand Order (FGO). It was really cute and the outfit could hide all the manlier parts of my body, such as my deltoids, my veiny arms and rather strong calves. The lack of hips was also not a problem, since a petticoat gave the skirt a lot of volume and flounce to balance out the broad shoulders. I knew FGO was no longer popular, but I wasn't going to spend $80 on an outfit I'd wear only once. So Tamamo no Mae for AFA 2022 it was (minus the tail, which was too unwieldy). Anyway, cute maid outfits are always welcome at cosplay conventions.

(Fox girl + Maid outfit + Pink hair with two ponytails = Kawaiiiiiii 😍)

For those who have not cosplayed before, outfits have a LOT of fiddly bits. Putting it on requires a bit of time and preferably a mirror. Not wanting the hassle of lugging around an outfit to AFA, I decided to set off from home in cosplay. It was going to be slightly embarrassing if someone saw me in cosplay, but the most I was going to get was 1 or 2 quizzical looks from people in the neighbourhood seeing a guy in a maid outfit walking to the carpark.

Oh boy, was I wrong.

I always dress on weekdays so the neighbours are at work and the lift never stops at any floors on the way down. Being cautious as usual, I'd peek out into the corridor to make sure no one was there, quickly take the lift to the 2nd floor so the lift doors doesn't open to a bunch of neighbours, spy the route to the carpark to make sure the coast is clear, before walking 1 flight of stairs to the car. Precautions are taken, because my neighbours all know my family and I don't really want to answer awkward questions on who that woman coming out of my house was.

AFA on 26 November 2022 was a Saturday and it was 1pm when I was dressed and ready to leave the house. I peeked out into the corridor and didn't see anyone, so I quickly stepped out and locked the door and pressed the lift. But while waiting with my face looking directly at the lift door, I realised to my horror that my neighbour's door was open...AND MY MALAY NEIGHBOUR WHO STEPPED OUT SAW ME IN A MAID OUTFIT WITH A PINK WIG. AHHHHHH!! I was just thinking omg omg omg hurry up lift, why are you taking so long to come down from the 25th floor. The lift did eventually reach my floor and when the door opened, it was packed with people, including a family with a little girl (she did refer to me as auntie so that was a good sign). I felt incredibly embarrassed but had no choice but to endure the lift ride down. The lift proceeded to stop at 3 more times to let people in, before finally reaching the ground level.

Looking on the bright side, as embarrassing as it was, it would be very easy to explain that I was going to a cosplay event, which was the reason for me being in an elaborate maid outfit and as a female character. Had I been in regular clothes, it would have been difficult to explain to the neighbour why I was dressed as a woman.

I made my way to Suntec City and reached the convention centre around 1.30pm, by which time the tickets to the AFA Expo hall were already sold out. Not that it mattered since I wasn't planning to visit any of the booths. I was expecting AFA to be really crowded, but stepping off the escalator into the crowds thronging around did make me momentarily very self-conscious. I've never been dressed as Isabelle in such a crowded location in the day. But realising that around 30 - 40% of the people were in cosplay and nobody was giving me a second look, I quickly shed of any sense of unease.

While attempting to link up with a fellow crossdresser, I walked around to get a feel of the event itself. The crowd was young, mainly consisting of tertiary students and some young working adults. Many were dressed as characters from the popular game Genshin Impact, but other Anime and games characters also made an appearance. Everyone was doing their own thing; Cosplayers were applying their makeup, taking photos with each other, doing cool/silly tiktok videos, sitting in a secluded wing to hide from the crowd and heat, queuing to get into the Expo hall and taking even more photos.

I spotted a significant number of crossplayers while walking around, ranging from those who put in a lot of effort to look like their favourite female character, to the low effort macho guy in a wig and dress. At least 5 other guys were dressed in maid outfits and we gave each other knowing nods when we saw each other. Takes one crossplayer to recognise another crossplayer (I find it is our manly backs that is always an immediate give-away).

(Cosplayer was dressed as Surtr. She was really pretty)

The setups for photography stations at AFA intrigued me a fair bit. There were simple ones with just a single softbox and speedlight. There were also elaborate setups with C-stands, multiple softboxes, reflectors and backlighting. Normally for the stations with elaborate setups, there was usually a really pretty and well dressed cosplayer posing for a huge group of photographers. It would have been nice to be the centre of attention, but I didn't feel courageous enough to go up to one of these stations.

I did see a number of old uncles in their late 50s or 60s with good compact mirrorless cameras equipped with separate flash made for taking selfies, going around taking photos with the prettiest female cosplayers. While it could be argued that everyone is entitled to their tastes and the cosplayers were happy to take the photos, as an observer it honestly did feel quite creepy.

Considering the large number of really good looking cosplayers with elaborate outfits, I was surprised that a few people actually came up to me asking if they could take a photo. Strangely, they were boys who looked to be early to late secondary school age, so I did have a slight suspicion that they probably wanted photos with "female" cosplayers who were actually a guy (one of them did admit that he was collecting such photos to share with his guy friend). But whatever. I was however, pleasantly surprised when a little girl came up to me shyly for a photo request.

(Yes that's me. Sorry no showing of face here as my makeup was too light)

I manage to link up with my friend and we took a bunch of photos together, as well as with other cosplayers. The favourite photo I took with another cosplayer was with this little 3 year old girl dressed as Anya from the Spy X Family anime. She was so insanely cute and was continuously stopped by people for photographs. Made me wonder how cool it would be if I were to dress my daughter up for an Anime convention.

(I like high heels. But my toes do not)

I lingered around AFA till 5.30pm before calling it a day. Having spent a good 4 hours walking around the crowd in my 5 inch heels, my feet were absolutely killing me. (The heels made me look fantastic, but these shoes were NOT made for walking). I changed out to regular clothes, went to Don Don Donki for a simple sushi dinner, popped into H&M for a quick round of shopping as Isabelle before heading home. I was so tired from spending one full day as Isabelle at AFA that I spent the rest of Sunday taking multiple naps to get my energy back. Also I think I caught a bug from AFA that caused me to develop a sore throat and cough that lasted for a week (likely Covid, though I strangely kept testing ART negative).

Attending AFA was an eye-opening experience and it's great to check off an another item on Isabelle's bucket list. On reflection, there are a few take-aways from my first cosplay convention:

1) While I did feel too old to cosplay, I foresee myself going for at least one more cosplay convention. After all, I like dressing up in costume and taking a lot of photos. It can be really fun, especially if you have friends you can coordinate an outfit and take photos with.

2) At cosplay conventions, nobody gives a damn if you crossdress. Apart from Halloween, I find cosplay conventions to be the next best event to try going out in public dressed as their female self. While it can be a bit scary due to the crowd if it is your first time out, there are many other fellow crossplayers attending as well. It could be just the thing to build up your courage to do regular things enfemme.

3) The amount of effort taken to cosplay is really high. Other than getting a fitting costume, there is a need to style the wig, properly apply makeup, learning to pose and just being daring enough to be out there. I think this is something that the crossdressing community could take a leaf from. Put in the effort to look your best self, be bold and show the world your beautiful female self!

Halloween is known in the community as international crossdressing day. The day where you can step out into the streets wearing almost any outfit, regardless of how slutty it is and not have anyone bat an eyelid.

It was also on this day 3 years ago that Isabelle took her first step out in public. I was utterly terrified and hyper self-concious, constantly worried that I'd be recognised as a guy in a dress. But Isabelle has grown so much since that day. I've improved my makeup skills, mannerisms and dress sense. But most importantly I've realised that my fears were largely unfounded and lived entirely in my head. This Halloween, I stepped out confidently in public, feeling glorious and a perfect 10/10, in the same dress I had worn on my first time in public. I was ready to show the world the confident, elegant creature I had become. It was my Halloween Homecoming.

I went for a she-devil/vampire look, with a white wig, black choker, clip-on devil horns, smokey amethyst and black eyeshadow, dark red lipstick and that killer off-shoulder bodycon little black dress that hugged all my curves. It took me around 1.5 hours to fully doll up since I didn't do a test run for my eyeshadow, but the end results was on point. I felt like a succubus all ready to drink deep on a poor sod's mortal soul. Too bad I didn't get faux vampire fangs, otherwise the look would have been perfect.

(Rare photo of Me. Because I felt so on point that not sharing would be a mortal sin.)

I didn't have any plans for Halloween 2022 originally and was content to just rest my old bones at home, but my fellow sister was incredibly persistent (in a nice way) to drag me out to Marquee, a club in Marina Bay Sands (MBS), to soak in the Halloween atmosphere since they having a themed party. Incidentally MBS was also the first place I met this fellow sister. While I'm definitely not the clubbing sort, I decided to just give it a shot in girl mode. I was sure clubbing while dressed as a pretty girl was also going to be a lot more fun than a frumpy guy.

(Entrance to Marquee. I forgot to take a pic of the queue)

The queue to enter the club was insanely long, snaking for more than 100 metres across 2 levels. Though we joined the queue at 9.40pm, and the club opened at 10pm, we only managed to enter around 11pm. The bottleneck was because processing of entry ticket purchases was slow. It did give our group some time to chit chat and walk the length of the queue to see cool and quirky costumes. My favourite costumes was a zombie 包青天 (Justice Bao), 3 girls dressed as 梁婆婆 (Liang Po Po) and a guy dressed as a covid test kit. Most girls turned up as sexy maids, devils, angels, students, sailors and other occupations. There was one sexy policewoman pulling around her caucasian boyfriend who was dressed in orange convict overalls. Slight kink vibes there.

After a long wait where they checked our bags and ID, we finally got into the club. Pretty sure the guy checking my ID gave me a second take because my male photo ID clearly looked quite different. But I'm definitely older than 18 so he waived me in. Clubbing music filled our ears and as I strode into the dim light of Marquee's entrance wearing my 14cm heels, I felt a slight joy and bounced a bit to the music. Isabelle, clubbing for the first time! Another bucket list item checked.

Marquee was every bit the high end club, with all the nice bells and whistles. Being in Marina Bay Sands, there are standards to meet after all. It had a lot of LCD screens and strobes, a high ceiling which made the place look massive, a ferris wheel, a slide, multiple phototaking locations and a central dance floor. Occasionally someone would make a large drinks purchase and "runners" carrying led light illuminated bottles would walk onto the club floor to the table that ordered it.

Music was pretty great and there were dancers dressed in sequined flared mini skirts and makeup like crying dolls with running black eyeshadow. The dancers' moves were so, so good and insanely hot. I was mesmerised by their dance routine and couldn't stop watching. Their movements were so fluid, free flowing, yet every bit intentional. Almost made me want to sign up for some dance lessons to learn their moves.

(Short clip of the dancers. Pardon the potato quality as it was zoomed in)

There was also a good vibe in the club which put me in a mood to dance. While it was just bouncing around and moving my hands, being in heels felt totally different. The feminine energy made me feel sexy, unfettered by my male trappings. I felt...alive. I could move my body in any manner, however unmasculine and didn't worry about being judged. It was pretty nice.

Marquee's toilets had slightly magnified mirrors and warm lighting that were perfect for taking selfies. I spent at least 15 minutes posing and taking photos in front of the mirror (to be fair I wasn't the only one doing that). One cis-girl who was doing the same told me she loved my entire outfit, which was extra validation. But that night it was but cherry on the cake. I already felt female this Halloween night.

Before long, it was time for Isabelle to call it a night as I had a few appointments lined up the next day. After I got home, de-dragged and packed up all my stuff, I felt unusually awake despite it being 2.30am. I was still riding the high from being out and about. Though Marquee's entrance price was a steep $50, since I rarely club it was well worth the adventure. What a night, what a blast I had. I definitely incurred some serious sleep debt and messed up my sleeping patterns a bit but it was so worth it.

Isabelle's all ready for Halloween 2023 😈

(Clarke Quay on the Halloween weekend can be pretty fun)

Crossdressers who are still in the closet usually tell me that although they want to go out in public, they are very afraid of doing so. I fully understand how incredibly scary taking the first step out in public can be. I was once in your shoes, overwhelmed with fear and constantly worrying that people will recognise that I am a guy (I blogged about my first time). Fast forward 3 years and after massive improvements in my hair, makeup and dress sense, people on the street still easily recognise that I am a crossdresser. But my anxiety is no longer a blaring siren in my ears nor does it paralyse me. It is still there for sure, but it is now just a niggling thought that I largely ignore. We are lucky that Singapore is a safe place to crossdress. The primary hurdle we need to overcome is the irrational fear that exists all in the brain. So fellow sister who is still in the closet. Assuming you have mustered the courage to finally take the plunge, here are some suggestions on where to go. (While some crossdressers do go to HDB carparks in the middle of the night, I'm not going to suggest it. You're unlikely to see anyone there, but it is a horrible first time location. What are you going to do? Walk up and down the carpark ramp in your stilettos while you melt in your wig?)

1. LGBT friendly bars. Or Clarke Quay on Halloween

This is an awesome starting ground. Although getting to the bar itself might be a bit more challenging, once you're in the venue you can really relax a bit and be yourself. My first time out in public was to an LGBT friendly bar on the Halloween weekend. Even though I was sort of dragged out there and was so scared I was barely conversational, it did feel like a safe space, especially after the drag queens turned up. Although you are unlikely to meet other crossdressers (the community is tiny), a friendly transwoman or drag queen might decide to chit chat and give you a bit of encouragement.

If you're feeling a bit more daring, you could head to Clarke Quay. Try to aim for the Halloween weekend, since it is an excuse to dress up and be a bit sexier. Do remember to practice walking in your killer heels at home and bring out some plasters, or you'll be holding your heels and walking barefooted before the night is over.

2. Shopping malls

As scary as going out in bright daylight sounds, shopping malls are pretty ok places to crossdress. Most people are there on errands and will mind their own business. If you want to be a bit tactical, pick a large mall with big name brands (e.g. H&M, Zara) and go there on weekdays when the shops open (typically 10am or 11am, depending on the shop). There's barely a crowd because most people are working or in school, and sales assistant really don't care about whether you are LGBT or not. Boutique shops can be a bit more unnerving since it is smaller and the sales assistants might follow you around, but remind yourself that they are just being friendly.

3. Selfie studio

Selfie studios are kind of a new thing in Singapore. While this is a confined space that isn't exactly a "public" location, you will still need to interact with the owners of the place and possibly give a shy smile to other customers you see there. The good thing is that the owners usually don't care whether you are male, female or transgender as long as you are a respectful, paying customer, and anyone you see there wouldn't bat an eyelid about your crossdressing, since they'll likely be in costume too. Note that selfie studios usually charge by the hour.

4. Join an LGBTQ event in a public space

This might be scary, but it may just be the fastest way to make friends (I recently saw a Trivia night organised by the Katong Queers that looks really fun). I've also heard of group meet ups in the LGBTQ community for BBQ, board games and other very casual, non-bar/clubbing events. While I haven't joined any, with the LGBTQ community opening up more and more in Singapore, I think this could be a good starting point.

5. Cosplay event

I feel that cosplay is akin to a gateway drug for crossdressers going out in public. While I personally haven't gone to any events, quite a number of local crossdressers start off here. It can be a bit scary for a first timer, but with everyone just dressed up as their favourite anime character and having fun taking photos, it is a pretty safe starting point. Taobao has also significantly lowered the barriers of entry to cosplay since you can just buy off the shelf costumes. Might need a bit more courage than say....a carpark in the middle of the night. But you know, carpe diem right?

6. Parks / Marina Promenade

I'd say, this barely made the list. Personally I don't like going out to non-air conditioned places because in Singapore's weather, wearing a long wig makes you sweat buckets, which then makes your makeup run. But going out at night is a lot more cooling so it could still be pleasant. The Marina Promenade area, including the area in front of MBS is a pretty place to walk around at night with its lights and cityscape, without being overly crowded. So that's a decent option.

7. Museums / Art Galleries

This wasn't in my original list but someone suggested it after reading a crossdressing reddit thread...and yes, it IS a great place to go. They're air-conditioned, generally empty, they're big so there's many areas to wander around. And the main ones in Singapore are really great places for taking photos (so many people go there to take their wedding photographs). So you could consider wandering around in a museum or art gallery.

While picking a place is important, the journey to your destination will be your first brush with other people. If you don't drive, public transportation can be a bit daunting for a first timer since you'll be in a confined metal vehicle with strangers for a duration. One way to avoid talking is to book a private hire vehicle using an App, so the ride is paid for and you don't need to tell the driver uncle in your deep baritone where you want to go.

Another key tip is something I've mentioned this before and will repeat ad nauseam. For your first time out, please please do not wear your 5 inch stilettos, paired with a mini skirt and pantyhose. And don't overstuff your bras (deduct 1 or 2 cup size from what you think you should wear). While it might be a massive turn on for you, you'll stand out like crazy, which will make you even more nervous. Unless you've got an exhibitionist streak and enjoy people staring at you (yes, there are some who enjoy the attention), do try to dress a bit more simply.

Alright! So hopefully this post gave you some ideas on where to go for your first trip out in public. If you are still deep in the closet and still on the fence, make plans for it! Don't be like me and step out only when you're starting to get wrinkly. The younger you venture out, the more you can explore and have all the fun that crossdressing has got to offer.

After a really busy period, I finally carved out time to take a day's leave and have some Isabelle time to scratch the shopping itch. So on a Monday morning, I did my usual dress-up ritual; wake at 7.30am, travel from my parent's place to my own house, eat a heavy breakfast that would double up as lunch (eating in girl mode is a bitch and messes up my makeup, so I usually skip lunch on dress-up days. Also I dislike being stared at while eating), shave, bathe, dig out all my crossdressing stuff from the storeroom, spend an hour putting on makeup and transforming into Isabelle by around 11am. I'd then travel to the usual mall to visit my favourite shops. I'll pick out pretty outfits that catch my eye, try them out in the changing room, take some photos/videos, before heading back home by 3pm to round off the day with an outfit test of the new dress and wig I had purchased online a week back. There wasn't enough time to do a proper photoshoot at home, so I just used my phone camera as I was also feeling lazy (which resulted in underwhelming photos that weren't sharp enough). By 4pm I had to de-drag, take another shower, pack my stuff back into the storeroom, before travelling to my parent's house just before the evening peak our traffic.

Whew. What a day. I sated my desire to shop, but I felt....unsatisfied. Dressing up felt like a rush and obligation, which left me even more tired than a full day in the office. A chore consisting of a huge to-do list to tick off. Like why did I even bother to dress up?

I did a quick poll with my Instagram followers and feeling unsatisfied after a dress-up session wasn't a unique experience. Although the rush that I put myself through during each session was definitely a contributing factor, I don't think it is the only reason. I've been in the normalisation phase for quite a while now and have this niggling sense that my desire to dress up has been waning. The feeling of having been there and done that has sapped away the novelty of dressing up. What is the next thing for me to look forward to when dressing up? I've even started looking around for another bridal studio to do another photoshoot, but it feels like another attempt to blow a couple thousand dollars to chase the next hedonistic high. I get to wear some pretty gowns for a couple of hours, have photos to show off for it, and then what?

I suppose this is why people retire from crossdressing after a number of years. Because the hassle of dressing up outweighs the derived satisfaction and desire to do so.

I do have some plans to make dressing up seem less like a chore, starting with getting rid of my facial hair. I absolutely detest having to grow out a week long beard to a decent length before spending one hour plucking the individual hairs out for a truly clean look. I've gotten used to the pain but the time it takes just annoys me to no end. I do also hope to dress for a longer period without having to rush back home for my parental duties, so that will require some logistical arrangements. Halloween and Anime Festival Asia (AFA) is coming back this year with all the covid restrictions removed, so I also do hope to at least try attending in costume, which would make things a bit more interesting.

Recently one of my friends in the crossdressing community discovered the joys of shopping in public and oh was she a woman unleashed. Her outings enfemme spiked and she bought a lot more outfits than she would normally do so online.

Online shopping has its perks, but it doesn't hold a candle to shopping in person, at least for us crossdressers. Ever since I started shopping in person, I've stopped buying Isabelle's items online unless it cannot be easily obtained in brick and mortar shops (e.g. wigs, breastforms, costumey outfits) or I see something I really like at a good deal. Why wait 1 week for the few selected outfits to arrive in the mail when you can have IMMEDIATE gratification in the shops? Go to the right malls and you can even hit multiple shops in a few hours. Efficient and effective.

My friend's shopping spree is not unique to crossdressers in their discovery phase and it is likely temporary, so the damage to her wallet won't be that large of a bomb.

Crossdressing is expensive. As if upkeeping 1 wardrobe isn't enough, crossdressers need to spend money buying pretty outfits on a regular basis to satisfy the inner girl (almost like maintaining a mistress, except she also shares your body 🤣). I think it is ok to buy clothes as long as you can afford it and it makes you happy, but my advice to crossdressers who have just discovered the joys of in-person shopping is to avoid what I term, the "shopping chain reaction".

(By the end of Trip 4, you now have 13 outfits but only worn 4 of them 😅)

The "shopping chain reaction" is where you buy 3 outfits on your first shopping trip. You wear one of these outfits during your next trip and buy 3 more pretty outfits. And 3 more in your next shopping trip. It's basically a nuclear chain reaction but for shopping (very geeky I know 😅). Before long, you'll have more outfits than actual outings to wear them. You need to realise that changing rooms have really soft lighting that makes you look great in the mirror, and because you're sort of on a high during these initial shopping trips, every other item you pick looks great in the mirror. I've wasted money buying so many clothes I no longer wear because I don't like them anymore.

So to do your wallet a favour, here's my 3 rules to rein in your inner shopaholic:

The outfit must at least be a 9 out of 10
The outfit must be in a style you don't already have
Maximum of 1 outfit per shopping trip

Regardless, have fun on those shopping trips! Sales people really don't care whether you're a guy in a dress or not, as long as you're a serious customer. So don't worry too much about being clocked or using your male voice if you really need to speak. Just own it and enjoy your moment enfemme.

Musings of a Singaporean Transgender

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