Crossing over — How wearing heels taught me a thing or two

Kai Motta
5 min readNov 4, 2023

How free are we? How free are we to be openly who we feel we are? How free are we to escape the confines of our comfort zones, our enclosures of safety, our abodes and mix with society? To speak frankly, openly and willingly? To dress in the clothes and styles we desire? To embrace our sexuality and gender? To be able to simply just be?

I make a lot of films and in a recent comedy short it required me dressing up as a woman. Now as a child I never liked my face being painted. I hated it with a passion and while other kids ran around parties and events with butterflies, ghosts or whatever painted on their faces I always refused. It just made me feel uncomfortable, I didn’t like the feeling of something on my face. I never went through a period of wearing make up in my teenage years like a few friends did and like many others, I grew up in a very masculine environment. Alas, such was and is the patriarchal system we live in today. C’mon Kai, be a man! Man up! Interestingly I discuss with my teenage daughters the subjects of sexuality and gender, and when they tell me a male school friend is gay, I explain how that it is a huge move forward that he is able to be so open, considering when I was in education if a boy said he was a homosexual, his life by some would have been made hell. The liberal sexual environment my children now witness unfortunately didn’t really exist in Britain in the late 80s, early 90s.

Now until I recently slipped into a stunning yellow dress, blonde wig, applied my make up and stepped into 4-inch heels in front of the camera never did I sit and question, ruminate and research about how our society is conditioned by the division of male and female. Obviously, I knew it existed, but selfishly, I really had had no need to think about it in such an in-depth manner. I had political and societal interests elsewhere, and this subject had yet to surface. We simply can’t involve ourselves profoundly in every issue, unfortunately there just isn’t time.

If I was going to play a woman in my comedy film, I wanted to truly embrace my inner woman. I wanted to fully immerse myself in the role. I wanted to be unreservedly feminine. I wanted to cross the great divide to the very soft tender delicate effeminate space from the extremely tough macho rugged masculine arena. This may say more about me, but it is also an indication of the social environments we are also subjected to throughout our lives. I have to confess, it felt odd, wrong, taboo like and out of place but also exciting and lasciviously libidinal as I placed my feet into the 4-inch heels and transformed myself with the blonde wig! My character has always been one of rebellion. From as early as I recall I never liked people telling me what to do and got a kick out of crossing the line and behaving in an insubordinate manner. This was most definitely the results of a father who spent his years telling me from when I was a child ‘Should is a word that shouldn’t be in the dictionary!’ and then proceeded for the next 40 years of my life trying to tell me how I ‘should’ behave.

As I started to search through Vinted for heels and dresses for the comedy show (needless to say I now own more pairs of heels than my girlfriend, is that what’s known as a heel fetish?) I suddenly felt a wave of pressure from somewhere, something internal fighting against a type of conditioning that this wasn’t correct, it was out of place, it just wasn’t how a ‘man’ should conduct himself. Don’t misunderstand me now, I’m not saying I literally couldn’t walk through the high streets, shopping centres or congregate with others in pubs and clubs dressed as a woman, nothing was physically stopping me, but if I had I knew I would be subject to derision, odd looks and possibly violence. Because of my rebellious streak there was part of me that wanted to do this, not because I wanted to dress like this permanently, was transitioning or felt I was actually feminine rather than masculine, but simply because a societal conditioning had demarcated the genders and had defined who I was because I was a born with a penis.

It seemed strange to me that there should be any type of societal resistance to people expressing themselves in any way they choose if it truly doesn’t affect another. Afterall how freely do most people want to tell you how open minded they are, how they believe in the old worn-out maxim ‘live and let live’ and pull out the freedom of speech card only to swiftly show the boundaries of their minds in an instant and become the true small minded draconian figures they were raised and influenced to be. Of course, I’m not suggesting that any man that doesn’t want to dress as a ‘woman’ is unfree and imprisoned by social conditioning, on the contrary, I’m proclaiming should a man want to dress as a woman, why not? Really, what is the problem?

It wasn’t until I read Ciara Cremin’s book ‘Man-Made Woman — The Dialectics of Cross-dressing’ mixed with my unhealthy obsession with neoliberalism that I started to gain an insight, an understanding of what was happening, what was taking place, what the whole picture consisted of. Why do I feel a certain pressure not to dress as a woman? Why did it feel wrong? And it is now clear there is a strong relation to patriarchy and economics.

As men we know either consciously or subconsciously, in my case now, consciously, that as men we rank high on the social economic echelon. We’re privileged compared to the females we mix with in society due to how our societies have been organized. We know our place and understand the position of females. As men we don’t want to be feminized because somewhere deep inside, we fear it can remove us from our privileged position. We fear we have too much to lose. We know where the dividing line is and don’t want to cross it. Why would we, when we are benefiting? Our social surroundings and conditioning tell us that to be anything like a woman is to be further down the food chain. To be anything like a woman is to be weak. To be anything like a woman, is to not be a man. But thankfully it looks like there is a change coming… Heels or no heels.

This clearly tells us a lot about not only ourselves, but also the economic patriarchic capitalist system we are all currently drowning in. I’m not advocating men dressing as women at all. Although I quite enjoyed it, the libidinal eroticism involved in the action, though I think this is somewhat related to an act of rebellion… Freud! I think it interestingly highlights the inequalities of the current patriarchy many of us are struggling to exist within and how that affects us psychologically.

Let’s be honest, really, who would honestly advocate any form of inequality? Particularly, if it stops you wearing 4-inch heels!

Ciara Cremin’s book ‘Man-Made Woman — the Dialectics of Cross-Dressing’ is available from Pluto Press

All 3 of Motta’s novels are available from Amazon

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Kai Motta

Kai Motta is a British born author with three self-published novels on Amazon. He also paints, performs comedy, composes music & makes films www.kaimotta.co.uk.