Musings of a Singaporean Transgender

Hello fellow sister,

This is a letter to you, especially if you're relatively new to crossdressing or have been in the closet for the longest time. 

While our origin stories and the winding routes that we take through life are different, we all share a single commonality; our penchant for wearing women's clothes. It may have started inexplicably when we were 5 years old, or it only started in our 20s as part of a dare. But regardless, the activity of dressing up as a woman brings us great joy.

There is an unparalleled thrill solely reserved for us crossdressers when we unwrap our online purchases, to slide that new little black dress up our body and step into a pair of stilettos. The heart thumping in the ears and the quivering fingers as you feel the rear zip enclose your body in the dress. How is something deemed so wrong by society able to feel so damn right?

Remember, this is your life. While we are accountable to the people closest to us and have different responsibilities, this is the only life we have and we have to live it to the fullest (sorry readers who believe in the afterlife or reincarnation). So make plans to be financially secure and enjoy the female side of you, hopefully in public too. 

Most importantly, love yourself, always.

We are all cis-men who love to wear women's clothes, and that's ok. After all, women's outfits are f***ing gorgeous and better than boring men's clothes 😆

I was listening to a podcast that people do not talk enough about death when they are healthy, which results in problems when a sudden unfortunate event throws everyone and everything into chaos. This triggered random and rather morbid thoughts that I've always had. If I were to meet an untimely demise tomorrow, how would Isabelle's friends know that she is no longer on this world? Would my sudden silence in group chats and social media hint to friends that something untoward has happened to me? Or would they speculate that other circumstances have made me decide to socially purge Isabelle's existence? Given my current age, the latter seems a lot more likely. But if suspicions start to grow, how would Isabelle's friends even get the closure to their speculations? (assuming they needed such a closure). Would my friends be sad that they have lost a friend in life? Or was Isabelle's existence superficial and fleeting, like footsteps on a sandy beach; easily washed away and erased with each wave. Hopefully not. 

Thinking about death is a bit sad as it triggers all manner of emotions. But it is a good thought exercise to help prepare for the future. It made me wonder, how I would plan my posthumous activities.

If I could, rather than donating them to salvation army or selling them, I will give away all my stuff to fellow crossdressers who could put them to good use. I've accumulated quite a lot of women's clothing over the years. Counting everything that is in good condition, I have at least 40 outfits (majority are dresses), 10+ wigs of various designs, hippads and breastplates that are very usable, 5 pair of heels and a whole bunch of accessories that would make more than a few crossdressers very happy (after all, these are the items that have brought me so much happiness and joy over the years). 

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

To be honest I was considering whether to write about this or not. 

I have mentioned before that crossdressing is just like any other hobby, where people with a shared interest chat, meet up and participate in the activity that brings them so much joy. However, there is one major difference which sets it apart. The unfortunate reality is that when we crossdress, we take on a female name and persona of our own creation. Isabelle is my creation and my circle of friends who crossdress also know me as Isabelle. Although the thoughts and experiences I share with others in my chats, as well as my blog posts are true, I am ultimately still hiding behind a facade; no one really knows my real name, what I do for a living, as well as other aspects of my life. Such a separation of male and female lives is my isolation by design, and a strategy that many other crossdressers also adopt. This is because, it allows me to completely cut-off all ties should the need arise. Because the risk of my secret hobby being made known via another party (intentionally or accidentally) to relatives, other circle of friends or worse, colleagues, is too high for me to bear. Like any other friendship, circumstances can turn it sour. In especially bad scenarios, it can become hateful. Crossdressing is quite a superficial hobby and many who partake have different priorities, objectives and complicated life-stories. I've heard way too many stories of animosity developing over time within the community and in the same chat groups due to differing views or plain cattiness. As a fair amount of private info can be shared within such groups, being too open would increase my risk profile. I cannot fathom the regret I would feel if someone were to out me to my relatives/friends/colleagues. Even if such an action would brand the person a pariah, the damage would be done. 

As such, even if someone is willing to open up to me or share their personal phone numbers, I usually find it hard to reciprocate, since our risk profiles are different. The other party may already be out of the closet, careless with secrets, single (and thus do not need go worry about partners), or worse; catfishing. Whereas I'm only out to my wife and plan to keep this delicate balance for the rest of my life. I generally don't chat with or add profiles on social media that cannot be corroborated with other known crossdressers in the community, don't show their faces, or hide behind heavily AI-edited photos (i'm looking at you FaceApp). The irony is that if my younger self were to reach out to my current self now, I may very likely ignore my younger self (oops). 

This behaviour might be viewed as being uppity by some for not replying to messages/chats or accepting friend/follow requests on Facebook or Instagram, but I simply cannot adopt a careless attitude with regards to privacy.

That said, it is possible to have close friends within the community. I've seen some groups in the community who spend a lot more time together than with their other circle of friends and hanging out not only to crossdress, but to enjoy other aspects of each other's friendship. This is really great and comforting to see. Friendships is more than just a shared hobby. Hopefully in your journey, you find your own close knit group of friends.

I decided there was a need to write about this topic after a friend shared her unpleasant experience with another sister within the local crossdressing community. It wasn't the first time I've heard about what I would consider "unacceptable behaviour" by another sister. 

Crossdressing is a very niche interest and the community is tiny. Many of us take great solace in the social aspect of dressing up together, creating a safe space where one can let loose, be themselves and trust each other with our deep, dark secret that our closest relatives and friends do not know about. However, there are actions I consider to be unacceptable behaviour as a member of this small community. At its most harmless, it is an annoyance to the victim. At its worst, these unacceptable behaviours are borderline criminal.  

I will not cover illegal activities, such as stealing of women's clothes, attempting to take upskirt or partially undressed photos of other women in toilets. Such cases, which we read in the news far too often, are obviously criminal and will be dealt with swiftly by the law once found out. 

It is undeniable that crossdressing is a sexually exciting activity for many in the community. For this majority, slipping on hoisery, zipping yourself into a mini-dress and strutting around in high heels usually has the potential to get one's engine going.  If the goal of a gathering is to crossdress together and partake in sexual activity (be it just touching or full blown sex), as long as it is between consenting adults, it is perfectly acceptable, and crossdressing together could be a fun, sexually charged experience. The problem arises when the touching is non-consensual, thereby pushing it into the realm of sexual harassment.

Having a common hobby is no excuse to touch another sister without obtaining consent. Neither is the fact that crossdressers have a tendency to wear outfits bordering on skankiness, drawing inspiration from the sexually-inclined male mind and the need to be over-compensate using hyper-feminine clothes, with the laciest lingerie, shortest mini-skirts and sky high stilettos. As is the case for women, don't blame the perpetrator's lack of self control on the victim's style of dressing. In fact, there is no excuse at all to touch someone else inappropriately without their consent.

My suspicion is that some of these sisters know very well that for many in the community, crossdressing usually has its roots in sexual arousal. By luring young / new crossdressers with the prospect of a safe space and care from a fellow sister, they can create an opportunity to touch the youngling, in hope that this physical contact could, tempt the trusting newbie to partake in sexual activity in the moment of headiness. One could argue that such actions is part of the chase, or part of helping another sister get over her self-denial and break out of her shell. Any sexual fun that results is between consenting adults. But what if the person being touched doesn't want to be (and yet is repeatedly touched)? Or does something she regrets? 

Let's put it this way. If a guy inappropriately grabs or touches a lady he does not know, or even a female friend without first obtaining consent, it is considered molest and a criminal offence (I'm no lawyer, but that's my layman understanding of things). Unfortunately, the fact that [1] crossdressers are basically all guys,  [2] non-consensual touching incidents between crossdressers tend to take place in hotel rooms or in clubs/bars, and [3] the secrecy surrounding this taboo activity we partake in makes it difficult for the "victim" to come out to anyone or make a police report (in severe cases). 

This behaviour baffles me. Why would you steal another fellow crossdresser's photograph and pass it off as your own? One reason I can think of this "identity theft" is to catfish admirers on social media such that they can enjoy the attention, praise, get off on sex-texting, or perhaps try to obtain gifts in the process. 

There is one notorious crossdresser in the local community who has edited her face onto other crossdresser's photographs and posts the edited version on social media, claiming the photo to be of her. Like...why?! I know apps can do a face swap, to see how one might look with a body of a K-pop star, or wearing an ancient chinese princess outfit for the fun of it. But using other's photos and passing them off as yourself seems to take it to another level 😐

I suppose one can argue that this is the risk of social media. The moment it is shared on the internet, even if the account is private, there is a chance of your photos being downloaded and sent around. So if you share it with someone or on social media, you need to be ready for it to be shared in the public domain.

This is one of the worst crimes a crossdresser can inflict upon another. Maintaining privacy is a high priority among many in the community, and for good reason. Male to female crossdressing is not widely accepted in society. As much as society is slowly becoming "woke" and "liberal", the reality is that Singapore's society (family, school, workplace) in general still isn't very accepting of mtf crossdressers. More often than not, we are viewed as weird, unnatural, or worse - perverts.

Leaking out of a crossdresser's identity to family members, friends or colleagues can be potentially very damaging. Just like squeezing toothpaste out of the tube, there is no way to "unsqueeze" the toothpaste; the secret is revealed and damage is done. There is no way to justify such behaviour, even if the reveal was done accidentally (how can one be so careless with other's secrets?). If it was done intentionally, then whoever did so had malicious intent and needs to be branded a pariah in the crossdressing community. 

One could argue that what I described above as "unacceptable behaviour" is merely my opinion, and I should get off my moral high horse. Who am I to be the judge of what is acceptable or not in the crossdressing community? I suppose that could be true; I sometimes do sound like a goody-two-shoes. But in my book, these behaviours I described are red lines that I don't think should be crossed. For newly minted sisters just opening their own closet door and reaching out to others in the community, these are some behaviours to be wary of.