From cosplay to crossdressing, a question of reality?

Crossdressing is a widespread practice that is little understood. The male-to-female crossdresser, who differs from a transgender woman, has a palette of roles to chose from. But what impact does this playing with apearences have on our relationship to reality?

Estimated reading time: 7 minutes


Playing roles

You could say we are all playing roles in our lives, if only by unconsciously limiting our behaviour and dress to conform with the expectations that go with a profession or a role as husband, wife, parent or whatever… But for some people the roles they play and how they dress for them are more consciously and deliberately fashioned and acted out. I’m not talking about actors, whose job is to play roles. Nor am I talking about politicians, who sadly seem completely lost in the fictitious roles they play. But rather about everyday people who, from time to time, choose to play at being someone else, sometimes to such an extent that that ‘someone-else’ becomes a central part of who they are.


Take the example of Cosplay. The Japanese are particularly enamoured of this activity, which involves dressing to look like a character from a film or video game or that corresponds to a social role like teacher, secretary, nurse or schoolgirl. They parade as that character at dedicated events or in the streets. As such, there is often an element of caricature in the roles adopted. They are both larger and more limited than life. Yet despite this travesty of life, Cosplay is more acceptable socially than crossdressing, probably because it embraces roles in a way that is far less emotional and engaging.

Crossdressing: the hold of clothes

Emotional? A fundamental difference between the run-of-the-mill cosplayer and the male crossdresser who dons female clothes with relish lies in the emotional hold those clothes have over him and their link to gender and sexuality. Rather like with a fetish, in crossdressing female clothes are imbued with a power that seems almost magical. Magical? The hold the clothes have over the person is hard to resist, yet that drag (excuse the pun) defies rational explanation (See my article: Boy dressed in girl’s clothes). They are embracing the female in themselves, you might think. But it’s much more. For example, wearing female clothes and the associated feeling of femininity bring a heightened awareness of one’s body. At the same time, such clothes generally procure sexual stimulation for the wearer which plays itself out with others whether male or female, but equally can culminate in an ecstatic self-satisfaction in which the crossdresser plays all the roles.

Preparing a face to meet the faces…

In Prufrock, TS Elliot wrote: To prepare a face to meet the faces that you meet (…). His words are pertinent here, even if, in 1917, he was no doubt writing about a completely different encounter. Indeed, preparing a face to meet the world is exactly what most crossdressers do – those who dare show their face – not just with skilful makeup and padding here and there, but also specialised apps that make young beauties out of possibly less pretty, older men. And why not? They don’t necessarily make a secret of the fact. Not that they publish before-and-after photos – that would destroy the illusion – but rather they refer to their online selves as ‘virtual’, saying even that their real self is ugly. In a way, they have created a convincing female avatar which can take on a life of her own. In that virtual space all fantasies are permitted as reality with its unfortunate inconveniences and limitations is suspended. They ‘trap’ – to coin an appropriate word used to refer to those male crossdressers who convincingly pass as female – the casual viewer into sharing the illusion they can be pretty and desirable, inviting him or her to join them in a make-believe romp.

Crossdresser or transexual

It may be important here to make a distinction between crossdressers and transsexuals. This can be the most graphically seen in the attitude to clothes. The crossdresser dons female attire because it is identified as female whereas he is male. This cohabitation of ‘opposites’ is a source of satisfaction, if not intense pleasure. In comparison, the person who feels herself to be female despite being born in a male body wears female clothes because it is natural for her to do so. Of course, in reality, the distinction may not always be so clear cut.

Multiple roles to play

Amongst the considerable ‘community’ of men who crossdress, there are multiple roles. For example, some dress as a caricature of women, aiming to be more woman than women, with immense breasts, pulpous lips, large hips and seductive, colourful clothes. In some cases they go so far, it’s almost as if they want to cast ridicule on the people they are so fascinated by. At the other extreme, there are those who aim for the mousy submissiveness and silliness of another female stereotype often played out in a relationship of dominated to dominant with men who are seen as all-powerful ‘alpha males’. There is no place in such a scenario for the powerful, creative woman that all women could be. Then there are those for whom age is a key factor. They dress to look much younger than they are, ‘licensed’ to flaunt current social taboos because they are in reality adults in a consensual relationship with themselves. Or yet again, there are those who rest suspended between boy & girl, the femboys, who relish the ambiguity of being both female and male but also young. They very often portray their feminine side as submissive. Finally, let’s mention those who don’t give a damn if they are taken as a walking contradiction with beards and hairy legs and knobbly knees under a dress or blouse and skirt sporting bright red lipstick and pink-rimmed spectacles. Their very appearance is a screaming challenge to established binary divisions that can be far more disturbing than their ‘trappy’ counterparts. They could be portrayed as champions of a ‘truth’ that refuses to be silenced.

A fall from grace?

This whole phenomenon, for all its richness and fascination, comes with an unfortunate feeling of foreboding that does not hail from moral or religious considerations. It’s simply a suspicion that something’s amiss in the fabric of society. In this proliferation of gender role playing, the underlying question is the long-term impact of flirting with, if not drowning in, a simulacre of life? That said, it may well be that life itself as most of us live it has become a sequence of fanciful roles, much of which we take for granted, but which ultimately moves us ever further from reality. A path down which politicians with their alternate facts and disregard for reality are hurrying us. Why is that undesirable? Because, it is only by referring to a reality in which we can trust that we can make appropriate decisions about how to act and what to do (See On Truth by Harry G. Frankfurt, 2006). Without that solid link to reality, we are slaves to the self-serving, alternate realities people in power feed us and which can lead to catastrophic miscalculations. It’s a rather depressing thought, but the growing experimentation with gender roles may not solely be the gloriously ambiguous coming-of-age of humanity it’s advocates herald, but also a further indicator of a growing rift between us and reality in what might amount to a second fall from grace.

Alan McCluskey, Saint-Blaise, August 2022.


There are many aspects of this subject that I haven’t been able to include in this article, making writing it a challenge. One such aspect is the role of clothing as a shield or a ‘screen’. Another more over-arching topic is the nature of reality. Within the limits of such an article, I often had to allude briefly to key points that would have merited more development. One answer would have been to embark on a book about crossdressing, but I prefer to stick to exploratory articles as questions arise and keep the more extensive writing for novels where the questions explored find an echo. The Boy & Girl saga, of which I am currently writing a fourth book, touches on, amongst other things, the joys and challenges of teenage crossdressing.

Find out more about the Boy & Girl Saga

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