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…

Fiona Dobson

The crossdressing blog you’ll love even if you’ve never tried your sister’s panties.