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[Backstory hidden by spoiler: feel free to read in entirety or scroll to bottom for summary.]
The first memory I have of being uncomfortable with anything gender-related was at age 5 or 6, when my dad told me about a news article of a boy who had transitioned. He jokingly remarked, "hey, if you wanna transition, don't wait too long or it won't work." In hindsight, he wasn't suggesting that I wasn't behaving enough like a boy. I simply took the joke too seriously, and ever since then, I often found myself begrudgingly having to reaffirm my male identity, because I picked up on his suggestion that transitioning is an absurd idea. Absurdity is probably people's default view of transitioning, where I grew up (China).
Around age 9, I often shamelessly borrowed dolls from a girl whose mother was co-renting a house with my mother, but I did what you'd expect a boy my age to do: create elaborate combat sequences. In other words, they stood in for action figures.
Around age 12, I felt attraction to a girl for the first time. I hesitantly talked to my mother about it, and because I didn't finish the sentence at "I like...", she actually had to coax the answer out of me, because I didn't consider that the answer could have been "guys". She reassured me: "you like girls? that's wonderful news, actually!" In other words, puberty hit, and my childhood default asexuality turned into standard teenage heterosexuality, and that was somehow a confusing event for me. Around the same time, I was constantly suspected by my classmates of being gay, when in fact I was just generally awkward and deliberately hid my attraction for girls I liked.
Shortly thereafter, I became fascinated with high heels for some reason. Maybe it had something to do with living alone with my mother who occasionally wore them, or maybe it had something to do with often noticing the one girl who regularly wore high heels to school despite being only one year my senior... in middle school. I tried on my mom's heels for the first time around this time, without her or anyone's knowledge. A lot of adrenaline built up to the moment, and as soon as I had them on, a boner shot up.
Naturally, the next thing I tried was wearing a bra, but to my surprise, that did nothing for me. I was also not fond of the idea of trying on panties, because it seemed unsanitary. I did get some excitement from wearing a strapless invisible stick-on bra that I found when my mom and I moved houses, but when she found it and realized she had no use for it, she threw it away, without knowing what I was up to, fortunately.
For the next several years, I didn't have many questions about gender identity, and I went on secretly exploring my love for high heels. However, I was always met with a wave of guilt/disgust/ridicule after pleasuring myself with heels on, which prompted me to remove them as soon as I was done. I distinctly remember being somewhat disgusted when one Halloween, I saw a high school classmate (who was an openly gay male) wear a ridiculous outfit which included high heels. I remember thinking to myself that I didn't want to be like that. I was also disturbed by traditional drag/crossdressing. Meanwhile, trap cosplay was being slowly brought to my attention, and I had mixed feelings about it.
My senior year in high school, I had been doing theater all through out high school, but it was the first time I was asked to play a gender-reversed role. The scene involved two couples, but someone in my group had the idea that everyone's gender should be reversed. I was the only person against the idea, and I had a rather heated disagreement with a group member who was the most frustrated out of everyone, with my refusal to cooperate during rehearsal. After rehearsal that day, I cried for a bit in my car, before going home to message my group about what was troubling me and how I just needed some time to work past it. What I basically told them was that my straight-male ego was fragile, and that it was being threatened by my having to get into the mindset of a female character. In the end, the scene went well, but I was more than glad to be done with it.
My first year in college, I made a platonic female friend when I matched with her on tinder and later discovered that we happened to be on the same floor of the same dorm building. I didn't get into the specifics, but I let her in on my secret for liking heels, both seeing women in them and wearing them. She was very accepting of it, since she often sent me images of different styles so that we could discuss their aesthetic appeal or lack thereof. I got the feeling that I was like her straight version of the stereotypical "gay bff", not that I was opposed to it.
My third year in college, I got in touch with the kink community local to my university (since I had long been fascinated with the idea of being with a tied-up girl, or being myself tied by a girl, or less realistically, being the tied-up girl). Around the same time, I ordered my first pair of heels from online, which I rarely had a chance to wear because I lived in a dorm apartment with 5 other guys. I did enjoy secretly wearing them to bed though. This year in college held a lot of growth for me, as I got to see lots of other people be comfortable with their unorthodox identities. I was still not a fan of seeing highly feminine attire on people who still had identifiable male qualities, but it did give me enough courage to sometimes sport high heels with my normal guy attire when attending events with the kink community. At one event, I think I impressed a few people by removing a jenga tile using only a heel.
My fourth year in college, I was invited to attended a small Halloween party with a few friends from the year prior, and after heavy deliberation and reassurance from my wisest friend and then-roommate, I threw together a joke costume which consisted of platform stiletto sandals, black sweatpants, a black t-shirt, cardboard cuffs, and cardboard bunny ears mounted on my beats headphones. I called it my "low-budget playboy bunny" costume. When I showed up at the party, the three other friends (all women) were first surprised by how tall I was all of a sudden and then more surprised when they looked down and saw why. Over the course of the party, they expressed multiple times how impressed they were by how well I walk in my heels. They also said they had a lot of questions, but for better or worse, most of those questions went unasked. We happened to watch a movie where a character was made fun of for her "stripper shoes" being impractical, as it was a horror/comedy. Naturally, everyone turned toward me, and we had a good laugh. On the way home, my roommate commented something to the effect of "you seemed more... complete" with the heels on. I proposed that it was merely because I normally slouch a bit, whereas heels force me to maintain decent posture, and he agreed, but "complete" was etched into my memory.
The year after that, I found the need for black leggings, because they seemed like the most practical solution to a problem I had, and because I thought they could be kind of sexy. I had just bought work attire, which consisted of a couple of well-fitting dress shirts, a pair of slim black jeans, and black sneakers. However, I found that sitting down lifted my pant legs above my socks (these were the first pants I've bought for myself), and that biking to work in jeans early in the morning was uncomfortably cold. I had a pair of men's leggings that my mom bought me, but they slid easily, weren't all that comfortable, or warm for that matter. The supermarket where I frequently got my groceries happened to have super cheap black leggings (only $2), but I was a little embarrassed to even visit that aisle, since it was mostly a feminine product aisle. I circled the area for half an hour trying to come up with a cover story if I was confronted (building a Van de Graaff generator), which in hindsight, was probably more suspicious than if I had just gone and grabbed what I wanted. In the end, they were everything I expected them to be, and they were super comfortable. Although my hips are rather narrow like a normal dude's hips would be, I think the profile of my butt and legs looked pleasantly feminine in leggings.
When quarantine started, I decided it was a perfect opportunity to see what happens if I let my hair grow out. It's been about a year since my last haircut, and after a few months in the too-long-for-short and too-short-for-long range, I think my hair finally looks nice right after a shower, but I haven't put any effort into maintaining that look for the day-to-day (so my current hair looks like Michio Kaku's, but all black, and a little messier). My Chinese relatives have begun to nag me about getting my hair in order and lightly ridicule me for looking like a girl, but I don't really mind, because I'm past the point of questioning my identity or reaffirming my identity to others.
[End of backstory, hats off to anyone that actually sat through the whole thing.]
I've come to terms with who I am by acknowledging that I don't necessarily need to identify with any specific labels, and that's all well and good until I need to start thinking about presenting myself to others. I present myself as male by default, because it's just easier to go along with people's social expectations for the most part, but where I'm having doubts is how to present myself to attract people that I'm attracted to. As I am now, I'm a slim Asian guy that gets some attention in China but next to none in the US. Conventional male attractiveness is probably attainable if I work at building muscle over the years, but I also kind of don't want to part ways with the option of convincingly presenting as feminine if I ever felt like it. I think I'd enjoy looking in the mirror and occasionally seeing a version of myself that I find attractive, but the makeup and wardrobe skill I'd need to develop for that is also nothing to scoff at. I think at least once, I'd like to attend some kind of appropriate event where anyone who saw me would think "cute girl" until I hit them with a bass-baritone "sup bro", but I can't see myself ever presenting as even remotely feminine in day-to-day life.
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