Musings of a Singaporean Crossdresser

4 years of university zoomed past and before I knew it, I was quarter of a century old and into the workforce. This meant that I was back living with my parents (fewer opportunities to dress up) but had more disposable income (SHOPPINGGGG 🛍👗).

I had started to build up a larger stash of clothes (nowhere near my current size), and squeezing in dress up sessions when I could. I had yet to discover makeup and took no effort to do so, in part because I didn't have the luxury of space and time to properly try it out at home. Although I could have booked a hotel room to try it out, blowing $200 just to dress up for the night didn't exactly feel justified.

(I could have booked Hotel 81 to save money but I wasn't that desperate 😅)

Work was stressful at times and I felt that my gender dysphoria flared up a bit more at night during these moments. In my brooding moments I would question my sexuality, the unfair cards that life has dealt me, and whether I had the strength to stay in the closet for my entire life. In the darkness I would wish fervently that I was a beautiful woman, but open my eyes to see a flat chest and manly arms/legs. It was disappointing that it would all remain a dream. 

But being a realist, I just counted the good things going on in my life and tried not to feel so sorry about my self. Plus there was also work the next day so I just brushed it all off and went to sleep. Usually, the busyness of the work day and people all around was a pretty good distraction to brooding thoughts. That being said, I don't think I had sorted out my emotions properly. Guys have this bad habit of not talking through their feelings, ignoring emotional needs and shoving them deep down, only for accumulated issues to manifest again with a vengeance.

On the relationship front, guy mode was doing pretty well. After a long period of dating, I finally popped the question and asked my girlfriend to marry me (she said "Yes"). I had considered telling her about my crossdressing on many, many occasions, but I chickened out everytime. I couldn't bring myself to jeopardise the relationship I had spent so many years building, and felt obligated to continue the illusion that I was just a normal dude. I swore to stay in the closet for life (Nope, I didn't 😅. More to come in a future post)

Nevertheless, I was happy that I was marrying the girl I loved. We went into wedding preparations rather quickly. Some guys are known to hate wedding preparations, but oh no, not this guy. It was pretty fun, and one of my favourite activities was visiting wedding dress shops. I would walk down racks of wedding dresses and occasionally feel the fabrics of a gown I fancied. If it was really pretty, I'd pick it for my wife to try. In a sense I was living vicariously through her. My taste wasn't too shabby, so my girlfriend was very open to my suggestions. Win-Win for everyone 😁

(The old Gown Warehouse in an industrial building in Woodlands. They have since moved to Dempsey. Oh how far they have come)

Of the shops visited, I especially liked Gown Warehouse. It was a massive shop decorated with plush carpets, chandeliers, with rows of neatly arranged dresses. But what I loved was the elevated platform at the front of the shop; with large full length mirrors at different angles, and spotlights aiming down for maximum effect. Even till this day I would occasionally fantasize about being the bride-to-be, trying on gowns, admiring myself on that stage and feeling like an absolute princess.

Ok, I should stop gushing about trying on wedding dresses 😬 Back to the story

(BTOs are cheaper but man do they take a long time to build)

Married life didn't really have an impact on my crossdressing, as my wife and I occasionally lived apart in our parents' home as our flat wasn't ready yet. I still had my own private space now and then. It was only when we moved into our own BTO flat did I start to feel the change. I took extra care to designate well-hidden spaces in the house to squirrel my ladies' clothes, brestforms, wigs and heels (they were in opaque boxes, within unsuspicious plastic Toyogo wheely boxes, out of sight at the back of the storeroom). But even with this precaution, I felt a growing worry that my wife would accidentally stumble in on me in women's clothes and the fallout that would ensue. For the first time, I was unable to sleep away this worry. My questions had come back to haunt me once again. Was I truly able to stay a closeted crossdresser for life? 

I'm skipping my pre-university and army days as this period wasn't too eventful, crossdressing wise. Pre-U was a really hectic time, with studies, CCAs, exams, dating, etc. Army surprisingly wasn't too much of an issue, which is sort of proof that crossdressers fit in with the other dudes equally well, and sometimes even better. Being outfield, exercising and doing army stuff took my mind away from crossdressing.

University however, was a different story. It was the time when my crossdressing was taken to the next level; owning ladies' clothes, wigs and shoes. This was made possible with the advent of online shopping (Asos ❤). 

Prior to this I had only been wearing my relatives' clothes. My sister's clothes were too small and my mum didn't have great style (read: too auntie). 

I lived in a dorm, so it was kind of my own space. That meant that I was also able to dress up without the fear of making too much noise and waking my parents at night, or my sister suddenly coming into my room. I even bought a large mirror so that I could see myself in girl mode (Yes, very narcissistic. But come on, which CD isn't?)

It was LIBERATING.

I remember very clearly the first few items I purchased. I had a penchant for evening wear, so I wanted to feel like I was a debutante, or a high school girl going to the prom. After scrolling through countless pages on ASOS, I finally picked out a red bandeau prom dress with a sweetheart neckline, black bra and panties with lace trimmings, and 14cm black leather high heel pumps. Delivery was estimated to take a week. During the lead up, I was absolutely obsessed, thinking constantly about the presents I just gifted myself.

When the goodies finally arrived, I could barely hold in my desire to try them on. My heart was hammering in my chest with excitement as I slipped into my own lingerie, zipped myself into the snug confines of the red dress, stepped into my stilettos and placed the wig on my head, my crowning glory. So what if my bra cups were stuffed with balled up socks? Wearing my own lingerie, dress, heels and wig, I truly felt like a woman for the first time.

I thought I was absolutely gorgeous, as I posed in front of the mirror. Thinking back, I probably didn't look great, but the "pink fog" that clouds a crossdresser's judgement when in girl mode had addled my mind and skewed my perception. A slightly geeky guy was standing in front of the mirror no longer. I was a girl attending her prom, waiting to be crowned queen.

The "prom queen" outfit had a bit more mileage, but before long, my inner woman wanted more. She wanted to be the tarty secretary in the office, dressed in the classic white blouse and black pencil skirt. When Kate Middleton got married in an elegant lace gown with a plunging neckline, my inner woman wanted a similar white dress too (with lingerie to match).

It was hard to keep myself from buying more and more clothes. There was always a new exciting style to try. Fortunately, budget and wardrobe space kept me from going on massive shopping sprees.

During school breaks, I had to move out from my dorm, so my stash had to be brought home with me. Being slightly paranoid, I was very careful and kept my ladies' clothes under lock and key. It was harder to dress up at home with my parents around, so I could only do so super early in the morning or very late at night.

All in all, University was a pretty fun time. I compartmentalised both guy and girl modes pretty well, managing to dress in my room reasonably frequently without being discovered. It might have helped that in my guy mode, no one would have ever suspected that I was the slightest bit inclined to wear ladies' clothes.

Some of the questions I had in my mind back then included:

It didn't help that when I was a teenager, dial up modems were a thing, google didn't exist and people found information primarily from libraries or their parents / elders. 

So how on earth was a fledgling crossdresser like me to find answers to the gnawing questions that I had? I tried searching for books on crossdressing or transgenderism in the library, but didn't find any. And the internet searches lead to a few obscure sites about successful transgenders, history of transvestism, or transgender erotica (Avenue Q was right. The Internet is for Porn). 

Television was poor sources of information too. Jack Neo and his crossdressing act as 梁细妹 or 梁婆婆, Jacky Chan as Chun-Li or some characters in a stephen chow movie were caricatures of crossdressers. It was slapstick comedy and these actors were dressed for effect.

Manga and Anime were surprising sources of exposure to characters who crossdressed. I remember watching this police anime called "You're under arrest!", and the prettiest, friendliest, most ladylike cop Aoi Futaba was a guy. Such characters were accepted which gave a bit of hope, but it is what it is; fiction.

It was hard not to feel alone in the world.

I think millenial crossdressers do get it better, given the wealth of information out there. Which might be why I observe CDs dressing up in public at a younger and younger age.

I don't remember when exactly it began, but sometime around the age of 10, I felt inexplicably drawn to girls clothes. This manifested in longing thoughts of wanting to wear a skirt to school, or silly acts like stuffing both legs into a single sweat pant leg hole to pretend it was a pencil skirt.

(The cartoon captures the feeling spot on. I wish I knew who drew it so I could credit the artist)

In upper primary, feelings of gender dysphoria became a bit stronger. We had racial harmony day in school every year, so a lot of the girls were dressed in their pretty and brightly coloured satin qipao (旗袍), my sister included. I still remember tremendous feelings of envy. Why do they get to wear such pretty clothes?! I wanted to go to school wearing one too! But I knew it was impossible, since I was male. Society and my family have told me that it was wrong.

When the opportunity came, I snuck into my sister's room to try hers on. The qipao was the sort with multiple clasps (instead of a back zipper), and my hands trembled with a heady mix of excitement and fear of being discovered. Unfortunately I was larger in size and wasn't able to fit in the qipao, but feeling the satin against my skin momentarily made me a very happy girl.

Another poignant memory was secondary school selection. All Singaporeans children aged 12 will go through the Primary School Leaving Exam (PSLE). Each secondary school had a minimum entry score and qualifying to enter was dependant on your PSLE score (out of 300). Back in the day, you had to select (up to 6) secondary schools you wanted to go to and rank them from your first to sixth choice. A booklet with all the options were given to everyone. 

I remember flipping through the book in my room and letting my imagination run wild. I'd scheme to secretly submit only all-girls school for all my 6 choices. The school would have no choice but to accept me, and I'd be forced (not unwillingly) to attend an all-girls school and wear a skirt to class. Was Singapore Chinese Girls School (SCGS) the one for me? After all, the pretty ones all seemed to choose there. Or was I a brainy girl, who could enter Raffles Girls School (RGS)? Or maybe I'd choose one of the schools with pretty pinafores.

It was a silly mental exercise, but wanting to be a girl did occasionally border on obsession. Alas, it was all fantasy and I stuck to the script, out of fear of the repercussions, and the knowledge that it wouldn't happen in reality.

I liken it to any other hobby. For example, football⚽️. People get obsessed over football because it brings them joy. Staying up till 3am to watch EPL matches, discussing non-stop about the mad skills of certain players, buying matching jerseys for the entire family and making the once in a lifetime pilgrimage to the Team's homegrounds.

For me, I love to shop for new outfits online and in person. I obssess a bit after each purchase and refresh my feed constantly when I'm waiting for goodies to be delivered. I am willing to spend to replicate a look I saw in a magazine. And it is my dream to wear a wedding gown for a photoshoot (a girl can dream).

The only difference is that general society currently labels crossdressing as deviant (unless you're really pretty). A man is supposed to be the Alpha; a leader, someone strong and in charge. Dressing up in women's clothes emasculates him and makes him "lesser".

As much a I wish my hobby will be socially acceptable in Singapore, I have no illusions that it will not happen in my lifetime. However, Singapore is pretty great in general and a safe place, so I do thank my lucky stars for being born here.