Musings of a Singaporean Transgender

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.

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.

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. 

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 😈

 

(Warning that this will be a bit of a ranty post)

Facial and body hair is a bane of crossdressers' existence. They're a bitch to remove and doing so takes way too long. Of all the things that I detest, the need to remove facial and body hair is right up there. And that's saying a lot because I'm of Chinese ethnicity, so compared to many other ethnic groups, I'm not very hairy. I've got leg hair that gets a bit wavy when long. I've little body hair on my chest, back and arms. In the facial hair department, fortunately I'm more of a Liu Bei (guy on the left in the photo below) than a Guan Yu. My facial hair is still thick enough to look like a brush if grown out and the distribution of it ages me 15 years and gives me a weird homeless look rather than a rugged masculine DILF look.

(I've always wondered how the guys in shows of ancient China have such sleek looking beards. Likely just attachments)

 

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?)

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.

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.  

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. 

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. 

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? 

 

(Transgender Youtuber Contrapoints. She is as gorgeous as she is funny)

Contrapoints: "I'm aware that the conventional beauty standards are a racist, sexist, ablelist, fatphobic, transphobic social construct designed to preserve power relations and sell products. But does that awareness mean I desire any less to be conventionally beautiful? Well...no. I want it more than ever! The problem with the intellectual exercise of critiquing things doesn't usually affect my desires that very much. So what am I supposed to do? Sit here in silent contemplation until my desires finally align themselves with the interests of the international proletarian revolution? Oh Fuck the revolution! I want to be a pretty rich girl."

If you haven't already discovered her Youtube channel that already has 1.6 million subscribers (as of Sep 2022), then you totally should. She is eloquent and hilarious, discussing gender related topics covering various view points. Putting out an excerpt from her video doesn't do her delivery of the topics any justice, so do watch her video on beauty, which I have linked down below. Do note that her videos are generally quite lengthy (30min or more).

So today's post is about beauty. Everyone wants to be beautiful. It is a desire that spans across sexuality and gender. Straight, gay, lesbian, bi, male, female, trans, non-binary folk all want to be beautiful. Don't we all follow Icons and Influencers on social media, wishing that we could look like them and enjoy the high life that their good looks has supposedly conferred upon them? Pretty girls seem to effortlessly become models and enjoy sponsorships, gigs, fancy meals, jet-setting lifestyles, supposedly high pay to sustain said lifestyle, and throngs of fans throwing themselves and dollars at them; things that the plain Jane (or John) on the other side of the phone could only dream of having. Winning the genetic lottery grants what is known as "pretty privilege" that opens many locked doors. 

It isn't just about the potential monetary benefits. As much as we need to learn to love ourselves, being conventionally beautiful undeniably makes us feel good. Looking into the mirror and being able to think "Damnnnnnn girl you look good" sends that dopamine rush to the brain. And when others heap on compliments, a person's self-confidence is boosted even further; to dare to speak a little bit louder and hold the head up a higher. Being acknowledged as pretty  makes us feel great about ourselves. 

For us crossdressers, the need to be beautiful is the ever present goal...or at times, the only goal. The highest prize is the ability to successfully emulate the conventional feminine ideal in appearance. Almost every single post on Reddit, Instagram, Facebook and other social media platforms used by crossdressers is screaming to show off this ability, demanding the Internet for validation with the question "Am I Pretty?" (Yes. Yes I am pretty. Tell me I am pretty. Goddamn it, like, upvote and share this post you anonymous, faceless other person over the internet. Even better, shower me with comments in a thousand different ways to tell me how pretty I am. Do it! Tell me I am pretty. Please? Oh and don't forget to follow). And the community itself feeds this need, along with a boatload of envy. Our chat groups regularly discuss how gorgeous some other young crossdresser or transwoman is, never mind that said beauty may be a product of plastic surgery or photoshop. We regularly lament our various flaws and fervently wish that we had this or that physical traits.

When asked: "Will you ever consider transitioning?", a reply I sometimes hear is "I'm too old to be pretty" or "Only if I can be pretty". Heck, that is the reply my brain tells myself too. For many of us (myself included), should the decision to transition be made, I don't think simple facial feminization surgery alone is adequate. If I am going to slide down the slippery slope of spending hard earned dollars on plastic surgery, suffering the physical, social and financial pain of transitioning, I'm sure as hell going to make sure I come out the other side looking drop dead gorgeous. After all, in for a penny, might as well be in for a pound. (Looking like Lalisa would be sweet. Or the goddess that is Gemma Chan.)

Will the quest and need to be beautiful for ever end? For us crossdressers, I don't think so. But it is important to recognise that in our pursuit of it, we should not let it consume us with envy. 

I was recently chatting with a newbie crossdresser who commented that she came out to her friends recently, who turned out to be very accepting of her gender fluidity, positive vibes all around. But she also read my blog and had wondered if she was too daring to take such a big risk. Of course she was already out to her friends during a dinner and dance event, so any potential worries about being too open was well, moot. She was in her early 20s, so she attributed the difference in risk tolerance level between herself and what I seemed express on this blog to be a generational thing.

Damnnnnn. 

Your girl Isabelle is old. No offence taken from the conversation of course. But it was interesting to hear that perspective. The newbie crossdresser had already attended Pink Dot SG, got support from her female friends (and some male ones), and was all ready to explore her female self. She did not strongly identify as transgender (at least not yet), so in terms of the mindset and need to be recognised as female, I'd say she is considered to be a crossdresser. The willingness or the feeling of readiness to come out this early certainly did not occur to me when I was her age. Back then, I was all ready to keep this secret to myself and take it to the grave; a scared crossdresser in her room wishing to set her inner girl free but too worried about the implications of letting the world know. To this day, other than my wife, nobody else knows. Granted, this situation is of my own design, since there isn't really any great reward if I let others know about Isabelle (other than seeing their amazement).

Of course, the internet was fledgling back when I was in my 20s, smartphones weren't really a thing yet and online shopping only just started. There were some resources on the internet for transgender folk but very limited. 

So there is a generational gap. Quite a number of crossdressers my age are still in the closet, whereas the younger ones seem to be exploring their female selves in public and coming out to their friends at a much earlier stage. There is definitely some bias of course; we are only aware that someone is out of the closet when their social media presence reflects as such and not everyone is so open on social media, so statistically speaking this observation cannot be verified. Nevertheless, I think it is definitely a fact that members of Singapore's LGBTQ+ community, crossdressers included, are coming out at a younger age. The internet has showed that our "condition" isn't unique and it is ok to be a bit different from other boys and men.

Now more importantly, with this realisation that I am a product of my era, other than attempting to look hot and lean into the MILF vibe, how is an ageing crossdresser going to stay relevant? Hmmmm

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.

Occasionally I have younger crossdressers message me to say they wished there was a local community or event that they could join, to meet others who understands them and to hang out enfemme. I tell them that there is a community in Singapore, but they will need to reach out through social media, as the community stays largely private and away from public eyes. However, I had a rethink of whether I used the term "crossdressing community" appropriately. The local crossdressing community isn't so much a community, but a collection of individuals belonging to scattered cliques that occasionally overlap. Over time, some gradually expand as new crossdressers join the group, while others become inactive and die out due to various reasons, such as internal disagreements, lifestyle changes of group members, or lack of leaders who actively organise gatherings. In its heyday, local crossdressers had Sggurls; perhaps the largest and most active since the advent of the Internet. It had a core group of crossdressers who organised annual gatherings that were as large as 30 - 40 people comprising of all ages, at different stages of their crossdressing journeys. But over time, the group splintered into other groups due to internal disagreements (so I heard). None of the splinter groups achieved the same amount of success, nor have new groups ever since. I belong in a few local groups and I have seen them try to expand, but they never seem to successfully grow beyond 10 members. Attrition rate is also high, with members deciding to leave or slowly becoming inactive and "ghosting" due to reasons unsaid. This shows the immense challenge in keeping a community alive and convincing people to stay on once it begins to grow beyond a certain size. 

In order for a community to form and take root, a number of ingredients are required:

Of the 3 criteria, the first is easily met. Regardless of motivations and style, we all like to dress up and be our prettiest self. The second criteria is a bit more challenging, since it requires community leaders who put in effort willingly to keep the doors open, whilst maintaining a certain safety and privacy standard that allows those who joined to feel safe and comfortable to continue to remain. The third criteria is the most difficult to achieve but is absolutely critical; without strong enough incentives to meet, even the best community leaders will also lose interest over time and dissolve the glue holding all the individuals together. 

The primary incentive to meet other crossdressers is to feel a sense of belonging with others who not only understand the pain of hiding the "shameful" desires, but partake and enjoy the very same activities that we take so much effort to hide. There is only so much one can do dressing up alone before it starts to feel lonely. So we reach out to other crossdressers through social media to exchange stories and tips, acknowledgement and praise, all in a bid to build a connection and eventually do things together enfemme. Newbies still in the closet hope to be able to discover a safe space outside of their bedrooms to dress up, those who have been out publicly want to go shopping, clubbing or enjoy high tea as a group of girlfriends, while the more sexually inclined want to meet new crossdressers to enjoy kinky time. Our reasons for crossdressing vary, but fundamentally it is the desire to be seen by others that incentivise us to gather. 

Each person however, has as much staying power in the general "public" community as they have incentives. The greater the incentive, the more people are willing to overlook issues present in being involved within the community. Unfortunately, there are many issues that disincentivise crossdressers from being part of the public community and growing it.

 

1) Lack of a proper venue to host and meet up: Most locations are too expensive (e.g. hotels), too small (bars), too public (regular restaurants) or inaccessible to the point it discourages people from turning up (e.g. Changi village chalets). Even if the stars align and a sizeable venue is found, organisers run the risk of being unable to recoup costs due to no shows. Crossdressers are unfortunately, terribly shy and some do get cold feet near the date itself. This means that successful events with more than 10 persons are rare (at least to my knowledge). If individuals cannot meet regularly in a larger group setting, it is difficult for a larger community to form.

2) The crossdressing community is tiny in Singapore: If you subtract those who are so far in the closet they cannot fathom even meeting others, as well as those who transitioned and shed their ties with most other crossdressers to move to the next chapter of their lives, you're looking at an even smaller group. Finding new crossdressers to join whilst keeping longstanding members from leaving the public space after they have established their own little cliques is therefore not an easy task. 

3) We are exceedingly superficial and selective of who we want to meet: Everyone wants to meet and hang out with the young, slim guys who make the prettiest crossdressers. Those who are older or a lot more masculine therefore have a greater tendency to get sidelined or find it challenging to connect with those who are new, unless they are someone well known, respected or a mentor of sorts in the community. The wide skill gap between the experienced and newbie crossdressers also pose a chasm that is hard to bridge. Experienced crossdressers who have honed their skill in passing as female typically do not want to hang out with fledgling crossdressers with no makeup skills and look like a guy who threw on a dress for laughs at Halloween, since the latter will likely attract unwanted attention when out in public. It is also harder to discern whether the newbie crossdresser is truly interested in learning and improving, or an admirer throwing on a dress as a trojan horse to get into inner circles. What we see then is a developing of "standards" known only to existing members that any new crossdressers must meet in order to become part of the group. While such "standards" can range from essential (e.g. new member must be a crossdresser and not an empty account looking to voyeur) to superficial and arbitrary (e.g. only pretty crossdressers can join), the more standards are imposed the less open the group, meaning that it becomes difficult for the group to grow beyond a certain size. 

4) One of the strongest incentives to continually meet new crossdressers is sexual...but not everyone shares this motivation: I am not saying that wanting to meet for dress-up sex is bad; there is nothing wrong with wanting to meet other adults for consensual sex. Rather, because crossdressing related sexual desire is such a strong driver, it has the unfortunate tendency to encourage the most predatory individuals to continually reach out to newer entrants in the community, who are also possibly more naive. This in turn causes crossdressers who aren't looking for sex (at least not in their first few encounters) to be extra cautious when reaching out and meeting others.

The problem of sexual predators being drawn to the role of community leaders and event organisers is similarly faced by the kink community, although there are differences which makes it even more challenging for a strong crossdressing community to form. For kink, sexual desire is a core driver for everyone; it is clear that everyone is seeking to find a safe space to play out their sexual kinks and thus sex is freely discussed without shame. There is also a the mantra of "safe, sane, consensual". Although not everyone practices this, it is a constant reminder to everyone that this is how things should be and the (bad) reputation of offenders tend to spread very quickly within the kink community. Individual identities are also fiercely guarded through the use of nicknames and taking/posting of photos are not allowed unless given explicit consent (policing of infringements is an entire issue altogether of course).

For crossdressers however, we can be broadly split into 2 groups based on our core motivations; those who only want to do regular girly stuff (i.e. entirely SFW), and the group who wants to do regular girly stuff AND have dress-up sex together. The former sometimes view the latter group with suspicion ("Are you talking to me to try to get into my panties") and perhaps an unjustified of sense superiority ("I'm better than you because I am straight and don't try to touch your pee-pee"). Even if the former group have sexual desires stemming from crossdressing, they don't freely talk about it because it is not socially acceptable and doing so immediately means one is no longer "straight" (this of course is a misconception...sexuality is not so binary). The lack of a common principle governing all crossdressers and non-existent policing in local groups by spreading the word about unsafe individuals and calling out predatory behaviour to make the space safer for new entrants means that it is down to the individual to be the gatekeeper of personal safety and identity security. This creates layers upon layers that we need to peel off during initial interactions to discover each individual's motivations and "trustworthiness", which becomes inertia for crossdressers to reach out and meet new ones in the community.

I think that the crossdressing community will continue to be the way it is; small scattered cliques that gradually expand or die off over time. It sounds a bit sad, but we simply aren't numerous enough to form a substantial community, and the incentives to do so is heavily outmatched by the disincentives and factors that threaten to tear apart the community after it has formed. Even if Singapore becomes more liberal and crossdressing is viewed as a less shameful activity, it will take a while before we have an open and thriving crossdressing community. That said, I do hope to see the younger crossdressers taking up the mantle to attempt to grow the local community.

This post is a bit more complicated than most of my other posts, so I'm certain some of you will have differing points of views. Feel free to comment to share some of your own perspectives

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".

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:

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. 

The term "Paradox of Privacy" usually refers to the disjoint between expressed privacy concerns and actual online behaviour. We bemoan about how big tech companies like Facebook and Google harvest our personal data and insidiously selling it to advertisers, yet we still willingly let them do so in exchange for convenience (google maps) and desire to show off our lives to the rest of our friends (sharing of photos/videos on Instagram and facebook).

I think crossdressers also suffer from their own paradox of privacy, albeit different from what I just described. We express privacy concerns and worry about the impact should our crossdressing inclinations be made known to our partners, relatives, friends and colleagues, yet we keep wanting to show our female selves to people, be it on Facebook, Instagram, Reddit, private chat groups, etc. This paradox is only faced by crossdressers who have not yet come out fully to the rest of the world (which is a lot of us in Singapore).

The crossdressers' paradox of privacy stems from the deep desire to accepted by others, to be told that you are beautiful/pretty/successful as a woman. Although the desire to be praised in this age of social media applies to everyone, for crossdressers the desire runs a lot stronger because acceptance is less easily available. Family and friends may not be understanding, while mainstream society has a tendency to brand a crossdresser a deviant (Crossdressers generally are viewed as perverts who get off from wearing women's clothes. It is really difficult for a crossdresser to explain that he likes to wear women's clothes because it makes him feel sexy or turns him on. A good parallel would be people who are into BDSM). Because acceptance and praise is in limited amount from a crossdressers' immediate circle, he turns to social media for likes/comments/praise. The way we "show-off" is also very narrow; usually it is a photo of ourselves dressed in out latest purchase, asking on social media if we are pretty or outright stating that we are. I am guilty of that measuring my success as a crossdresser by this same narcissistic metric.

Isabelle has social media accounts which a restricted group of crossdresser friends has access to. At times I think to myself: Why am I being so scared? I've taken so much effort to level up my skills to look sufficiently convincing as a girl, shouldn't I just make my accounts public or post my photos on more public platforms like reddit? This way I could be admired more, feel a sense of success, drive more viewers to my blog. But then my risk-reward alarm bells go off and my guy self slaps sense into Isabelle, reminding that such "recognition" that I seek on social media is ultimately meaningless and will not solve the deep rooted self-esteem and gender dysphoria issues that I face. And in exchange I flippantly squander away my privacy.

I chanced upon this gem of an interview shared in the sgbutterfly facebook group by the admin. I watched a bit of it without too much expectations and ended up making it through the whopping 3 hours long interview (broken into 3 separate episodes based on the themes and because it was too long). Kudos to the host for asking many interesting questions and for Aerie to share her story, along with giving well-balanced and thoughtful answers about many topics that transwomen and crossdressers face. Even though it was a long interview Aerie was pleasant and even slightly positive sounding, which was easy on the ears for sharing what could have very well been a heavy topic.

Aerie Rei is quite an interesting character, with a growing up story that I think many crossdressers and baby-transwomen can relate with, and a bit more. She came from a staunchly Christian family, spent 10 years in an all boy-school, started being drawn to everything female in Primary school, went through the phase of over-compensating by embracing toxic masculinity before snapping out of it, went to army, university, had a few girlfriends, worked in the Government, came out to her friends, colleagues and her parents, got kicked out of the house by her dad. She started her transition in 2020, at some point chose to be a porn star because it is something she loves doing and even flew to America for her first professional porn shoot. She was also fortunate enough to find love and married a Transman in Singapore (they have a polyamorous relationship). 

You could say, she had the typical middle income Singapore guy experiences and life trajectory before doing a major direction change. 

I think the interview is well worth the watch, especially if you're starting out or in the middle of your journey. If you've got no time, you can skip along to the parts that you are interested in. The host conveniently put a whole bunch of chapter links for each of his questions. 

Part 1 of the Youtube video is embedded below, while Part 2 and Part 3 are linked. Do have a watch! Alternatively you can also hear it as a podcast.

(The common time, money energy paradox...something is always missing)

I was walking past an elderly day care in my estate and saw a long line of old folks in their 70s to 80s, seated in chairs or wheelchairs, waiting patiently to be checked in by the day care staff in their 20s. Most looked like they needed varying degrees of physical help to move around. It reminded me to spend more time with my own parents who may be in a similar physical state in 10 - 20 years time. But it also reminded me of my own mortality; that in X number of years, even if I were to try an upkeep my body to the best I can, frailty is inevitable. 

Ageing is not just scary. It is utterly terrifying. No wonder religion has such a strong hold over humanity over all these years, promising that at the end of the tunnel when one has left the mortal coil there is a forever paradise waiting for all who were good and did the Lord's work (or a bad place for the naughty humans). Women fear the passage of time, because it robs them of youth and beauty. The skin sags and lines that mark the passage of time become apparent on the face, that no amount of plastic surgery can hide. Even men who are generally less concerned about appearances are not immune to the effects of time. If it were so, there wouldn't be a multitude of hair loss products in the market and drugs like Viagra that promise performance in bed as though he was a young man. Flipping through both history and mythology, we find kings spending hoards to find the potion of everlasting life, only to fail and pass on.

In my opinion, appearance and beauty is very important to the crossdresser; even more so than to actual women. This is because women have other things of importance to them that bring them satisfaction and a sense of accomplishment, such as a partner, children, career, etc. However for the crossdresser, his female self exists for more or less a singular purpose. To be the pretty woman that the crossdresser imagines himself to be. Which makes the concept of ageing even scarier, because beauty fades with age. I've already heard multiple crossdressers telling me that they are dressing as much as they can because they feel that they are growing old. And that they will quit crossdressing once they are no longer young enough to look pretty/cute (I highly doubt that, but we'll see).

But in a lot of the conversations, a certain number keeps coming up. 40 years of age. "Once I hit 40 I will stop crossdressing because I can no longer look pretty/cute anymore.". Holy shit. If there is any truth to that number, it makes me about half a decade more to expiry. Fortunately I think there isn't. But the big FOUR ZERO scares many people, because looks and physique does go downhill (the dreaded dad bod and beer belly becomes tougher to fight back). I'd be lying if I told you I wasn't worried. Even hitting 40 scares my male self, let alone the narcissistic inner woman who only wears 4 inch stilettos and obsesses over her social media likes and comments. There is always a tinge of envy when I see younger (and prettier) crossdressers coming out into the scene, because I missed that opportunity when I was younger. And I can no longer do things like grow out my hair, tying it into a man-bun in guy mode and styling it into a fabulous hairdo if I'm hitting the town as Isabelle. I recently tried on a Seifuku (Japanese school uniform) at iWan Selfie Studio and damn did I feel like an aunty trying to look like a young school girl. Fortunately I still have a relatively longer runway to pull off the sexy office lady look that is my forte.

A close sister who's a mature crossdresser told me that she can only pull of aunty looks now, but she tries to do a hot aunty. She puts in the effort and looks fabulous, but she also did say that age makes it hard to want to crossdress, since it is more challenging to meet the feminine ideal (especially the one in the mind). That having said, I also know of other crossdressers in their 50s - 60s who are going super strong, and are dressed so much more than they have ever done in the past (to be fair, it was a lot harder to meet up with others in the community and buying clothes online was non-existent 30 years ago). There is a huge sense of YOLO as well from these mighty gals, some of it because their children have flown the nest and if they do not live now, then when. It means that the drive to crossdress may dull with time, but it will still be there. Therefore I find it hard to believe that crossdressers who claim that they will quit after 40 will truly do so. I haven't got there yet, but I don't think I will quit at 40. But I definitely need to tamper my own expectations as I age, and instead be thankful that Isabelle did have many glorious days in the sun.