Crossdressing — When it’s not about clothes anymore.

Fiona Dobson
4 min readMar 8, 2019

“I wonder if there’s a deeper meaning here?” I mused as I watched the drag performance, along with a couple of friends. “Is there, maybe, some hidden message.”

It seemed just a little unlikely. I mean, how much meaning can one extract from “I’m just a girl who can’t say ‘no’” sung by a man with a beard?

Nevertheless, occasionally I find myself having to address the question ‘is it just about clothes’? The short answer is definitely ‘no’. There are a multitude of misconceptions about crossdressing, but I think I’m on fairly safe ground here saying that the clothes are really just an outward manifestation of a much deeper aspect of who we are.

For most crossdressers it starts with underwear, and it’s often a childhood experience. It then gets hidden away, and while there’s the occasional teenage fantasy it really just sits quietly at the back of ones mind. It’s only later that dressing really takes hold.

I’d like to point out right away that this is very different from the person who knows right away that they are a girl in a boys body. This is something radically different. This is about allowing feminine aspects of ones character to emerge. Not the total exclusion of male aspects. It’s too easy to think of this as one being either male or female. In fact, that’s rather the point.

For many of us, crossdressing is about rejecting the gender binary. We’re looking to explore that grey area between the poles. Few crossdressers have any desire to transition. In a survey of 2300 of my members only 8% defined themselves as gay, suggesting that there’s little correlation between crossdressing and sexuality. Crossdressers are generally happy to find that middle ground where they can adopt feminine aspects of themselves and blend them with the chosen masculine aspects that they wish to retain. Now, I’d be the first to say that can fluctuate. Some days I feel more masculine than feminine and there are most definitely some days where the feminine side of me is to the fore. And how wonderful it is to be able to express this in clothes, or in any other manner for that matter.

There are days when a touch of eye makeup is enough to make me feel complete. On other days I love to be completely made up, though wearing very androgynous clothing. And some days I am feeling neither one thing nor another. And why should I choose one or another, when I can blend the best of both?

If you were to look in a crossdresser’s underwear draw you may find it a little unusual. However, if you think the contents of my closet are disturbing, wait till you take a look at the contents of my head. As I move through my daily life there are moments when I want to nurture someone as I might a child. And there are times when I want to sit in quiet contemplation in a peaceful moment of gentleness that I really can only label as feminine calm. There are even moments in which I feel beautiful, rather than handsome.

And then there are moments of wanting to be the pushy guy, forthright and entitled by society. I’m not going to say it’s fair, but along with its drawbacks there’s doubtless some moments when as a crossdresser I can retreat in to the old and comfortable place of gender inequality that gives the masculine person all the unjust advantages that society has nurtured and seems so reluctant to release. It’s an easy, though somewhat craven thing to do. At least now I am aware that I can, and probably do, more than I really should.

A friend of mine recently had an incident in a public pool where a thoughtless male swimmer acted out a moment of threatening behaviour which was neither necessary nor warranted. My friend was wronged and took it. She said her piece, but with the resignation of someone who knew society wasn’t going to change that particular day, nor maybe for many years to come. It was just another case of being put in second place. Again.

As both a father and a crossdresser I can see the frustrations my daughters are likely exposed to daily in a different light. I also see the struggles people described as ‘queer’ face daily, though for me it’s in a very low level way. I feel very privileged to have a perspective that is a little outside the masculine norm, and I see a world that I didn’t really know existed in my masculine blindness. I am lucky enough to live in a liberal city where I am unlikely to be persecuted for my particular position, and so I experience few of the prejudices that I see played out daily toward some of my women friends.

So, no, it’s really not all about clothes. It ceases to be about clothes as we realise the clothing is just what we wear. What we feel is a better indicator of what we are. And it’s as different from the masculine stereotype as a pair of frilly panties is from a pair of steel toe capped work boots.

FD

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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