Musings of a Singaporean Crossdresser

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