Crossdressing — where’s my compass?

Fiona Dobson
7 min readJul 15, 2019

When one first realises that there’s a little more to crossdressing than simply putting on a pair of panties, most of us start a journey without a compass. Almost inevitably we do so alone.

For many of us finding out that there is a world of gender fluidity is a revelation in itself. As we explore it further, either through online discovery or tentatively exploring alternative lifestyle in our community the first steps are laden with challenges. When something is as simple as a fetish it is easily contained and managed. The suppression of a side of ourselves that has been trying to find expression throughout our life is likely the cause of unhappiness and probably depression. As it begins to grow stronger and we move to a point where it is no longer suppressed we start to find joy and fulfillment. However, for many of us there is no yardstick and no guideline to follow that steers us in the right direction.

Instead most of us fumble around in isolation. I am incredibly fortunate to live in a very liberal city where ideas of gender fluidity are far from unusual. It’s accepted and in the LGBTQ community is quite well understood. Now, that’s not to say it’s without challenges, some of which come from the LGBTQ community itself. There are people in the LGBTQ community who reject the idea of gender fluidity and struggle with people in the various stages of trans life, reasoning that you’re either gay or you’re not — or a lesbian or not a lesbian. I would not even be aware of such differences if I were living in some remote town in Minnesota. However, living where I do I can observe some complicated politics and how it affects friends and acquaintances around me.

You’ll remember that throughout the blog I often reference the idea ‘Accept yourself as you are, create yourself as you desire’. Part of this acceptance is not judging others. This makes it doubly unfortunate that some in the LGBTQ are so judgemental. However, our job is not to educate others, it’s to find a path and be the person we are meant to be.

For many of us, when we’ve first become aware of our differences, approaching family or friends is the last thing we’d do. If this is something that comes during teen years it’s got the potential to break the family, and destroy what limited means of support we have. For others it’s emerges in middle age and can be equally loaded with difficulty. It’s not unusual for this to emerge following divorce, and we can mistaken think it’s just a phase as a result of the end of marriage. I have a private theory that the trauma of the end of marriage can shaken things loose at a psychological level, and we are forced to re-evaluate ourselves in some pretty fundamental ways.

All of this brings me to a point that I’ve been thinking recently. I am so fortunate to have a vibrant LGBTQ community that I stand on the periphery of. There are however many people struggling along on their journey without such a reference point. Those who have no one to discuss issues such as thoughts around big issues like transition, and small issues like shoe styles for crossdressers are outside of any community with which to have a reference point. For instance, there will be many out there who have no one to talk to about gender fluidity, and so turn to the medical profession, for lack of guidance elsewhere.

Being gender fluid is not an illness. However, to someone who is confused by the lack of guidance and experiences feelings of shame and body dysphoria it can sure feel like it is. Having someone to sit down and talk to about it is a blessing of huge import. Being able to talk to some friends who may be on a path of transition, and others who simply enjoy dressing androgynously, and still others who just love to go to a drag bar and wear feminine clothes only to abandon them in the office the following day provides a wealth of experience and support.

Such communities can be both supportive and a place to provide support. Such communities build strength for all of us. Sharing ideas around sexuality and of alternative ways of dealing with gender helps us understand where we are in this landscape. Make no mistake, it’s a very complicated landscape. Some people are occasional dressers and very happy to be just that. Others simply dress because their partner loves it. Others dress freely all the time, yet have no plans for transition. Still others long for transition, knowing that from birth they’ve been wearing the wrong body. All of these varieties of trans person have a place somewhere on the gender fluid spectrum. Understanding where we are, or where we’re going, is very difficult for most of us in the best of circumstances. To be outside of an accepting community is a recipe for disaster and a good way to get completely lost. A program like my Premium Program endeavours quite successfully to give points of reference, but many of us also love to be able to discus and interact with others on our journey, which is the real value of a group like our Elite Whatsapp Group. Think of it a little like the difference between having a map, and being given constant radio messages from a control tower. The maps essential, but those messages are really important, too.

There are many forms of community. Whether one gains access to one by travelling to a nearby city with a drag community, or by joining an online forum such as The Fiona Dobson Whatsapp Group, there are means to access physical and digital communities to help get a reference point. Gender Rebels, Fiona Dobson and numerous other online communities can provide forms of digital community and raise talking points that are important in the understanding of our development.

My good friend Lenni, a lesbian who is in danger of having to surrender her lesbian card, tells me some interesting stories about LGBTQ culture. When I’ve talked to her about this she’s pointed out something obvious to anyone who has been immersed in LGBTQ life all their adult life, but less obvious to those of us who come to this in mid life.

“Why do you suppose so many teenagers in rural communities run away from home. They end up in large cities with LGBTQ communities and find people who actually understand their issues. Many of them aren’t equipped with the educational or life skills to earn a living any way but one.”

As a privileged white person this was not immediately obvious to me. As a lesbian in the LGBTQ world, it was painfully obvious to Lenni. So much so that I may have seemed incredibly ignorant to have supposed that this might be anything but the case. However, it was not a part of my life, so not really something I’d thought about much.

I almost feel a need to apologise for my whiteness and my good fortune to have been born with a fairly good hand of cards. Nonetheless, the fact remains there are issues that I have been blind to for much of my life, though not particularly by choice. This is, however, simply a fact of life. It is what it is.

For a moment consider the idea that the teenage run away and the middle aged white guy have more in common than at first meets the eye. They are both struggling with gender issues, though one in a much more acute manner than the other. The privileged white person has the luxury of making choices, while the disadvantaged teen often has situation thrust upon them. Their path offers little in the way of choice. Yet, the middle aged white person has likely suffered depression and other issues over the years, as the part of themselves they’ve denied has eaten away at them. The perils of this can go from mild ill health to suicide and can have some pretty unpleasant outcomes. Where this really goes is to the idea that the gender journey is a complex and difficult one but we may have more in common with each others than is immediately apparent.

I am certainly not belittling the struggles of the teen runaway. In an unsupportive family or a community that simply has no acceptance of trans issues it is hardly surprising that people search for something more. The pain of this is something that those of us that sail the gender fluid seas should always do our best to understand and reach out to ease in any way we can. Understanding it is the first step. Dropping judgement is the next.

Looking for understanding outside the Queer world of genderfluidity is likely to be fruitless. We’re only going to find understanding within our communities with ‘people like us’. The moment we start connecting with others we acquire our compass and have some points of reference.

In this hierarchy of fortune, the privileged white person is likely at the top. Below we can see tiers based on race, age, gender and affluence. Depending where one is it’s likely that the lower tiers are tragically occupied by aboriginal and low income individuals. The power imbalance in the trans world is both obvious and tragic. And this is where we really can help. Those of us able to participate in a community are able to be supportive to all levels in this hierarchy. And in this case we have to learn to ‘Accept all as they are, and help create ourselves as we desire’.

Fiona Dobson

http://Fionadobson.com

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Fiona Dobson

The trans blog you’ll love even if you’ve never tried on your sister’s panties. http://FionaDobson.com