Because trans women are not portrayed as authentically beautiful without qualification in the media, generally. We are either 1)
sexually alluring (not beautiful) predators whose aim is to entrap men in an act of debasement, in which case the revelation of our "maleness" is an act of horror or shock (think Brian vomiting in Family Guy when he finds out the woman he has the hots for is trans), 2) buffoons to be mocked, i.e. the femininity is shown to be artificial, with inescapable trappings of maleness poking out the sides, she is portrayed as delusional- attractive or desirable only to herself. A prototypical example of this might be Snowflake from Ralph Bakshi's Heavy Traffic, or Mrs. Garrison or the Undercover Cop from South Park. 3) the "tragic" trans woman who, regardless of physical appearance, is fundamentally desexualized. They do not exist to love, to be aesthetically appealing, to have a fulfilling internal life. Their only purpose is to talk about their transness and suffer for their transness so cis audiences can pat themselves on the back for not being revolted by the sight of a tranny.
The totality of trans portrayal in the media is "beautiful but". You're beautiful, but you have a penis. You're beautiful for a dude. You're beautiful (sniggering in the background). You're beautiful [but then a friend walks by and says "bro why are you flirting with a dude?"]. Again, for mainstream media to have a cis man to say a trans woman is
beautiful, and then have that character not shown to be delusional, or creepy, to not have that trans woman immediately undercut that by doing something humiliating or masculine, for it not to be obvious to the audience through context that he is simply humoring her, is very rare. For that character to
be played by an actual trans woman even moreso.
I found an excellent series of essays the other day that do a good job of explaining transmisogyny, where it comes from, and how it functions. You can find part 1
here. But there's a passage at the end of part 3 that I think dovetails nicely with why a cis man calling a trans woman beautiful without qualification is remarkable (bolding mine):
I see value in any of my siblings getting paid. But politically, artistically, it doesn't particularly matter to me one way or the other. What I ultimately want, what I care about, is trans media. Art made by and for trans people, dealing with trans subjects through a trans lens. Art made about trans people, but by and for cis people doesn't tend to be particularly
good in my experience. Because it is always mediated through transmisogyny, and always carries the transmisgynistic predilections of the cis creators. Typically it's crass, demeaning, base; insulting if not outright triggering. The bar is in hell. Like we're literally talking about "
scenes where a trans person is present, is treated as a person, and nobody humiliates or insults her" as the apotheosis of good representation at this point. But if you contrast that with actual trans media: with She-Ra, or Steven Universe, or
The Prince, or Stone Butch Blues, or Preacher's Daughter, like the difference is night and day. The topics, the tone, the treatment, it's categorical. What I want is more of the latter,
especially media by trans women, who are all too often forgotten in drives for trans-inclusive media.
I don't. We have had some 50 years of cis producers of trans characters and actors, dating all the way back to Andy Warhol, and we're just as misunderstood and misrepresented as we've ever been. When traditional media gives the reins of showrunning to trans creators they're blips, random droplets rather than a gathering stream, and what authentic queer lens exists is arrived at by metaphor, by trickery, or at times by outright rebelling against the wishes or demands of the cis producer to the ultimate destruction of the show or the trans creator's career. What has changed recently is that it has gotten cheaper and easier to get art produced and distributed, and because of that there is a slight burble from below of trans people making the art, distributing it, and viewing it themselves. But ultimately trans women are, by and large, very poor, and this affects the types of media we can work in, the volume that is created, and the reach it ultimately has.
It doesn't lead to greater sensitivity though, is my point. It is to keep us as figurines that cis people can pull out of the display case to gawp at from time to time. In the same way that formalization, institutionalization, or legalization of a Thing can render it less free, safe, or easy to access because to formalize, institutionalize, or legalize something is to impose a box upon something, rendering it eternally subject to the whims of the institution. So it is the case with "trans representation" via cis media. We exist at the behest of the institution (of patriarchy). We
cannot transgress. We
cannot be authentic. We must only ever be portrayed in a manner amenable to a cis audience.
I imagine it might be something similar to dating or being married to a white person as a black person. No matter how cool a person is, no matter how much they might "get it", be empathetic and willing to listen and learn, there will always be a barrier between someone who has grown up in and experienced our white supremacist world as a black person vs as a white person. There's always going to be some gap in knowledge or experience you're going to run into that you're going to have to explain to that white person. And since the thing you're explaining necessarily entails a divergence from the reality they experience as a white person, there's always (often) the risk that you're going to bump up against a source of fragility or unreality, to which they might respond with resistance, incredulity or minimizing, which you will have to manage, both in terms of the other person's emotional state, and your own. Sometimes these gaps can be outright dangerous, such as perhaps in the way the white person is accustomed to move through space or interact with institutions. Managing these things, anticipating these things, bearing the load of having to keep these things in mind as you go about your day are a tax. Yes, they can definitely be worth the tax (I am dating a cis woman, after all), but it is still
a tax. It's a tax which doesn't apply
as much when you're dating a trans person as a trans woman. I don't have to explain to her how much of a mess navigating transmisogyny in institutionalized medicine is. I don't have to battle through incredulity, skepticism, or argumentative responses when I discuss transition goals or my antipathy towards medical doctors. I don't have to explain why a barista referred to me as "them" has resulted in me sobbing in an office bathroom. I don't have to ask for reassurance or explain the need for reassurance or comfort every time I have to go through TSA. I don't have to deal with a partner playing cis's advocate when I tell them a cashier is transphobic. I don't have to worry about bringing my partner into trans spaces or introducing them to trans friends. This also applies in reverse, of course: I don't have to argue with my cis partner, nor she with me, when one of us tells the other that we're being followed, or what we should do in response, when if I had a cis boyfriend, I might have to spend several minutes convincing him that, yes, I am being followed, yes this is dangerous, no can you please stay on the line so he'll think you're right around the corner?
There's a joke within trans culture that the way trans people make friends with one another is by sitting down for coffee and traumadumping on one another. I did it just last week in fact. And the thing that's nice and remarkable about it is the fact that a) so much of the trauma that we share resonates or is extremely similar, and b) that the act of sharing that trauma is humorous. We're able to laugh together about the horsehocky we went through. There's a funny tweet I saw recently which unfortunately I can't find again, but said something to the effect of "being a trans person is telling a story or anecdote from your life to a friend or coworker that you think to be normal, amusing even, and watching their expression turn to horror or pity as they listen to the most deranged, fudged up thing they've ever heard in their life." Like that's the difference. Me telling a story about getting bullied in high school because they could tell I was queer even if I couldn't yet is met with resonance, identification, a mutual laughter, rather than scrutiny, sympathy, or a misplaced anger "on my behalf." It's really refreshing to spend time with those who do the former. It's why it is not merely the case that many trans people find they prefer dating one another to cis people, but also why many trans people tend to flock together, and don't tend to have many if any cis friends or connections at all in their social circle: many are embittered by their experiences with cis people; they have the scars (some literal) to show from their experiences and see little point in creating or maintaining relationships that tax so heavily.