What is it Like to be a Crossdresser?

Antonia Ceballos
The Shadow
Published in
5 min readJan 28, 2021

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For a long time it was absolute magic, a beautiful broken taboo blooming with fantasy where, in my imagination, I drew a bit closer to being the person I always wanted to be. When I dressed, I felt feminine and pretty, somehow less angry or at odds with the world, softened and comfortable. I felt something akin to the joy one feels when homesickness dissolves into the excitement of knowing you are nearly home. But as one weight lifted from me, it was replaced by a heaviness of heart that the feeling I got dressing wasn’t my reality 24/7. It was an unbearable lightness but I wanted to bottle it up and keep it.

Very often, I would suppress my dressing for months at a time but pervasive fantasies and dreams of turning into a woman, of becoming right, persisted… Those would always intensify until compelled by an overwhelming need to dress. When I did finally give in and do it again, it was a heart pounding rush not at all dissimilar to the first time kissing a crush. I’d see a girl in the street or a photo in a magazine and be filled with shattering dread that I wasn’t like her, I wasn’t in the right body. I’d be filled with an urgency to dress in women’s things. Often, I had purged them and I would need to buy more items, again. If I didn’t do it though, I’d spiral into deep depression. Those thoughts and feelings had been there as long back as my memory stretched but oh, so had the nagging feeling that they were wrong.

Sourced via Google from Archie Comics. Alterations by me

Another way I talk about the need is arriving home after a run that stretched longer than planned, the sort of exercise where one pushed past her limit. She returns ravenous and thirsty, her body screaming for water, sugar, salt and starch all at once. Everything she consumes is so much more pleasurable and satisfying than usual. To eat and drink in that state satiates a profound physical need in a very heightened way. Although the high from the run lingers, you realize you overindulged and after the binge, one feels ashamed and wishes she had a modicum of self control.

Sourced via Google — no source data available.

That describes three decades of my gender transgressing cycle: An emotional binge and purge. But I think it really had nothing to do with self control, it is rather self-denial, the effects of suppression of one’s innermost person. I don’t know why I’m like this, I just am, it’s always been there. The pain stems from the shame, it is refusing to accept one’s true self because culture says it is wrong, taboo for a male to choose to become feminine and ‘lower his social status’, to throw away the privilege of his birthright. As a result, I spent a lot of time hiding, lying and covering my tracks. What triggers the shame and confusion is that it feels perfectly harmless and somehow right yet you know, in the eyes of the world, you are bad for having the thoughts you do, defective for your innermost feelings. But the real problem isn’t so much the world, it is that you believe those things yourself.

Eventually, I broke that cycle in the most unexpected way. I came out to some people close to me and I stoped caring so much what others thought if I still bore remnants of my time en femme: Traces of eye makeup and orange blossom perfume, nails still painted. When one’s shame is given voice and drawn out into the light, shame cannot survive. Now, a lot of what I hid is just something I do everyday without all that much of a buzz. For example, androgynous items I wear to work, the jeans, shirt or flats from the women’s section have just become my clothes, even the underthings and nail varnish, a rather banal part of my dress. For me, that is the trade off of being out; it’s been worth it.

Oh, I do miss the electricity I used to feel when I’d draw the curtains and lock the door, pull on tights, pull up a skirt and step up into heels, the bittersweet longing I’d experience as I’d finish my makeup with mascara and then lipstick, knowing I’d have to wash it all off in a couple of hours. Then came the day, around 35, I gave in and admitted my face had aged so squarely masculine, my beard shadow so dark, I could no longer look reasonably feminine. I had to shift my approach, give up attempting to look like a woman. I’d always looked at my reflection and felt the person looking back at me wasn’t me but at least I had been able to transform that face and make it up it into a somewhat convincing semblance of congruence.

Often, in that twilight moment in the early morning, between the world of dream and wakefulness, before the tasks of the day enter my consciousness, all seems fleetingly as it should be. It is a warm, comfortable, deep glow of potential and excitement that swiftly dissolves into the background. A white noise phases in as reality settles over me. ‘One day,’ I think, ‘I shall roll out of bed, startled awake and realize it was all a dream and I really am a pale, raven-haired girl named Antonia and like Virginia Wolfe’s Orlando, I will be matter-of-factly underwhelmed by the reality of it: ‘Same person. No difference at all… just a different sex.’ …or is it perhaps more Talking Heads — ‘same as it ever was?’

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Antonia Ceballos
The Shadow

Thee/Thine/Thou/Vos/Ud./Tú/Y’all Y’alls/Yous/Thy/Ye/whosamawhats