Dressing in a feminine way is a form of advertising—me saying to partners, “see me for me”

My sexuality was like me setting myself a challenge–how to make it as difficult as possible to find a partner. After all, how many women out there are sexually interested in feminine men? Particularly in a patriarchal society? Pretending, so as to conform to the social norm was worse, a kind of slow death. I have been wearing women’s clothes, or at least items of women’s clothing, almost daily, for most of my adult life–starting when I was a teenager.  For me it is like drinking water–if I don’t do it, I will dry up and die. Technically, I guess this makes me a cross-dresser.

And yet…the whole narrative about cross-dressing has never worn well.  Why?  Because I don’t get aroused by wearing women’s clothing.  It isn’t something that turns me on.  Cross-dressing is a fetish, but I do not fetishize women’s clothing in a sexual sense.  But clearly, because clothes are gendered, it has to have a sexual underpinning, only not the same.  Women’s clothes have an existential meaning to me.

I started trying on girl’s clothes at a very young age.  Although family members were female, somehow wearing their clothes would have felt like a breach of intimacy.  Kind of vulgar, but also a betrayal of trust.  I never breached that self-imposed line.  Instead, I took my meagre pocket money, supplemented by odd jobs around the neighbourhood, and spent what I could on buying my own things.  I think I was 12 the first time I bought an item of girl’s clothing at the local department store.

What did I begin with? Black ballet clothes: leotard, tights, slippers, and a dancer’s silk skirt, because ballet was so angelic, so graceful, so utterly female.  And that is what I wanted to be. A princess, so light, delicate and ethereal. I sprayed them with a very feminine perfume and kept them in a suitcase in my room. Talk about needing to come out of two closets, neither in the traditional sense!  I loved the feeling of the sheets of my bed on my legs when I wore tights, and I loved how the clothes were clingy and tight, and how they made me feel.  This was before puberty, when I was frequently gendered female and I still had long, beautiful hair.

As I grew up, I began to wonder how I could reconcile how I felt about myself and how attracted to girls I was.  But when I saw a pretty girl, I didn’t have the feelings that boys my age expressed, a desire to “jump her bones”, but rather just wanted to be her. My romantic notions of being with a girl mainly involved kissing, touching, and cuddling. And absolution. Somehow, it was just this overpowering desire to be recognised, to be seen, and to be loved for how I felt. And only a girl could make me feel that way, could see me, could understand how I felt.  Girl’s clothes were like advertising for me—wearing hints of feminine, hoping that I would attract a girl who liked that in me.  I pushed the envelope all through school, trying to be attractive for the girls I had crushes on, and in truth, if she was pretty, I had a crush on her. How shallow, right? I was a pretty wild dresser in a very conservative environment–fringe, blousy shirts, Native American jewellery, what we call “hippie chic” or “boho style” nowadays.

I have no idea how I got away with obvious school dress code violations, though I know that sporting talent had a lot to do with it. If you were a “winner” in sports, the school tolerated a lot. Still, most of my classmates called me a “freak”. Funnily enough, one of the biggest bullies in the school, a beefy terror who was chief amongst the name-shamers, was also the sweetest to me…both publicly and privately he was protective of me–gentle ribbing was okay, but he was the first to stop others from going too far with me. I was always perplexed by that aspect of his character. And no, he’s not gay–he has grown into a total family man, cuddly, but all man, and super confident and relaxed in his masculinity. He has grown into one of the only men alive that I feel a little bit feminine around.

There was a lot of ritual in the way that boys and girls hung out together in high school, flirting, primping and preening on both sides, trying to be cool.  I was hard to place, outside of the system.  My feelings, my clothes, would have cast me out completely, someone to poke fun at, but thankfully my athletic gifts meant I could be aloof and not an object of ridicule.

My first girlfriend, the woman to whom I lost my virginity, gave me my first set of lingerie.  I did not ask.  We had never discussed it.  She just knew.  One day, after we had been fooling around, she handed me a lovely flat box with a bow around it.

“What is it?” I asked.

“Open it,” she said.  I did.  Inside was a black lace garter belt and matching panties.  “I hope you don’t mind, but someone gave these to me, and I’m not comfortable wearing them.”

“But its lingerie,” I said studying her face, trying to understand how she could see me so clearly.  

“You will get much more use from them than I ever will,” she said, somehow knowing how I felt.  I was totally floored–she was putting out in the open something I thought was hidden. The lingerie was a gift from an ex-boyfriend of hers, a boy in her class (she was one year above me), who was almost stalking her by modern parlance.  It was not the last gift of lingerie she gave me.  We never really talked about it; it just happened.  She liked making out with me when I wore lingerie.  She told me that I kissed like a girl, touched like a girl, and she just felt that I would appreciate it.  Wow!

She was an incredible person, to see me in a way that I couldn’t yet really see myself.  She was also the first of my partners (of many) to have been sexually abused growing up—and I don’t know if the issue is that so many women have been sexually abused, or whether somehow they sense in me a chance to heal—to reconcile desire for a male, but without all the baggage that usually comes with it (admittedly, they got a whole lot of other baggage!)

I was mistaken for a girl all the time before puberty hit.  I always felt it was a compliment.  I love the look of androgynous people of either sex.  Being called a gender-bender has always been a compliment.

But why this compulsion to dress?  Why is this not cross-dressing? 

I’ve always wanted to be female.  Clothes are like a uniform.  They carry gender in their shape and style.  Putting on women’s clothes and noticing the difference in fit is to feel how different the shape of a female body is, and to feel their psychological impact.  They are smaller, cover you much less, and are lighter, more delicate, softer.  Wearing them changes how I look at myself, how I feel about my body.

In other words, it is gender-affirming.  At least for me.  On the other hand, cross-dressers are fetishists and are aroused by wearing women’s clothes. This is not a criticism. I love cross-dressers.  Putting on panties or doing makeup and getting dressed are sexually exciting for them.  I’ve never had any of these feelings.  And yet, when I wear women’s clothes I feel much more sensual and it makes me want to be with a woman.

What’s going on?  Women’s clothes somehow make me more comfortable about my body.  I need that affirmation to feel whole.  To feel comfortable.  To feel understood.  The feeling I get when a woman looks at me and “sees” me because she recognises some item of clothing and knows it for what it is, and then looks at me not with surprise or disgust, but open curiosity, perhaps hunger or desire, is very fulfilling.  As if she is saying, how you present gives me comfort, and that comfort makes me want to be with you.

I love what Instagram figure @alokvmenon is doing with de-gendering fashion from a political standpoint.  It would be so nice to be able to just be out and about without judgement dressed in the clothes that make me feel my best.  But I also fear what he represents: I wear women’s clothes today precisely because they are gendered.  If he succeeds in “de-gendering fashion” would I still be able to find balance in women’s clothes?  

Will it ever be possible to de-gender fashion because of our divergent body shapes?  Wearing a gendered item is to say, “yes, I am bending the boundaries.”  I need that.

Would I still feel this way if clothes were not gendered?  I don’t know, but I think I look good in a skirt, really good in a dress, and that isn’t going to change.  They are right for my body.  Maybe the answer would be different for a cross-dresser?  Can someone who knows educate me please?