Halloween is a transgender holiday!
The experience of discovering yourself in a disguise.
The first time I ever felt like myself, I was dressed as a poor facsimile of Madonna for a Halloween party in 2018.
I wore fishnet stockings from Spirit Halloween, a black miniskirt from who-knows-where, a bralette from Target, pink fingerless gloves, a cross necklace and some dangly earrings. My then partner did my eyeliner and makeup. I think the vibe was the “Like a Prayer” music video, which is one of my favorites at the time, although now I’m not really sure how much I actually looked the part.
I didn’t really care that I had short hair or visible stubble or that I had no boobs to speak of for the bra I was wearing. What mattered for me is that for the first time in my life, I got to go to a party, where I didn’t know people, and present as a woman to them. This, to use terminology I sort of hate, was when my “egg” “cracked."
Halloween is one of the few times in most of the country that it’s socially acceptable to crossdress, and I’d wager that for most trans people but trans women especially, it’s the first time most of us really experimented with our presentation or really tried to appear as the opposite sex. Growing up in suburban Texas, gender roles were strictly enforced. Wearing skinny jeans made you gay, which essentially made you a woman. (So did liking Sonic the Hedgehog, which, well look how I turned out).
There were precious few times you were able to have an exception to the rule1: Football games, but only if you were wearing drag for comedic effect, being a theater kid, and Halloween.
Living at home with strict parents who didn’t support me being trans, the times I was able to express myself, then, were limited. Before I realized I was trans, I would occasionally go to the mall and let my cis girl friends put me in dresses and other women’s clothes "because hahahaha wouldn’t it be funny if I wore a dress. That would be crazy guys!” A few times in high school, I tried working up the courage to put makeup on at school and wear makeup to class. I never made it past first period, usually the point when someone would go “Hey, what’s on your face?” After I came out and was denied by my parents, I wore women’s clothes and makeup, mostly donated by my supportive cis girl friends, in secret in my literal closet in my bedroom.
For the longest time, turning 18 was the magical milestone I longed to reach, where I could move far away for college, never talk to my parents or friends ever again, transition, and become an unrecognizable bimbo. That was what I survived for, what I strived for. Imagine my white surprise when I ended up at Texas A&M, living at home my first semester of college.
I don’t really remember how the idea of being Madonna came about. It may have been my ex’s idea, or it was mine. By then, I had begun to make some good, supportive friends through college radio and I had started floating the “aha i’m nonbinary” stuff that you do before you really decide to transition. But I still presented “I’m going to be Madonna for Halloween,” with the same intonation you do a joke, like “Can you guys believe I’m going to be a girl? For Halloween?”
But when I looked in the mirror after donning my costume, I was shocked. The person I saw in the mirror wasn’t me, or at least the me that I was used to seeing. I had worn women’s clothes before, though either in the company of a few friends who understood or in my bedroom in the dead of night when I knew nobody would barge in and catch me. But this time,I had been dressed by someone who understood what was flattering and (this is important!) what was not. I had wanted to trasnition for so long but felt hopelessly lost. My grotesque male body could never look feminine, I thought. Looking in the mirror at Madonna changed that. Staring in the mirror was a stranger, but a stranger I recognized nonetheless, and not just because I’ve watched the “Like A Prayer” video a gajillion times. It was the person I’m supposed to be, if just a glimmer of her, staring back. That moment, I know now, was when I realized that transitioning was a possible future for me. I went on hormones almost a year exactly later, and the rest is history.
I don’t remember really anything from that Halloween party I went to dressed as Madonna, except for two things: I got really drunk because I was 18 and didn’t know how to be drunk, and a guy poked my padded bralette and was like “wow, I thought these were real, I didn’t realize you were a guy.”2
It’s funny to look back at the photo seven years later. Since then I’ve come out, changed names, and been on hormones for six years. I pass way better now and I even though I haven’t gotten any surgeries, I feel secure in my womanhood.
I struggled with writing this a little bit. I still carry a little bit of shame with me about the way I think about this, which to me is crossdressing, even though I never thought of myself as a crossdresser.3 I’ve consumed a lot of TERF media about perverted husbands who, in their telling, get off on “stealing” their clothes. But I shouldn’t be ashamed to say that wearing women’s clothing as part of a bad Madonna costume made me feel a little more like myself.
Expressing yourself, trans or not, is a good that should be encouraged. I’m glad that trans people have a holiday where for one day a year, it’s safer to be ourselves.
For that, Halloween is a transgender holiday. Happy halloween, guys and dolls!
By the way, if you’re trans and have a story about dressing up for Halloween similar to this, I’d love to hear it.
Thanks for reading. I’m going to try to blog semi-regularly again as a way to stay in practice when I’m not working and have a good creative outlet that isn’t related to my job. Feel free to subscribe to get this in your email when it comes out.
This implies you care about the rules at all which again, guilty as charged.
If you’re thinking of transitioning, trying to pass at a college party full of drunk people can be great because they’re not scrutinizing you too much, but also you might get fondled. YMMV.
The word in general gives me Susan’s Place vibes.