Musings of a Singaporean Crossdresser: November 2021

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

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

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

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

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

There's nothing wrong if crossdressing turns you on. But always remember, everything in moderation 😉

If you asked me before 2019 whether I would dare to step out in public it would have been a flat out no. And if you retorted to say that not only would I dress up in public multiple times, I would also participate in an interview as Isabelle for a video that would be shared on multiple social media platforms, I would say that you were insane (and probably stopped talking to you).

Oh how wrong pre-2019 Isabelle was.

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

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

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

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

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

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

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

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

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

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

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

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

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

- Chiharu (Singaporean)

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

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

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

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

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

- Anonymous (Singaporean)

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

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

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

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

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

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

- Lily Siow (Malaysian)

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

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

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

- Jessica aka Microsoft Excel 2007 (Canadian)

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

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

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

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

- Claire (French)

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