Alright, so I did some research on what everybody else thinks about this topic. A lot of people who were not trans thought that representation in anime was complete bullshit. As a trans person, I've actually been quite pleased by my representation in media. Everyone knows about Ouran High School Host Club, the story of a Female to Male dude who goes to a high school for the rich and bored. He makes friends and explores his identity, and everyone looks like they were drawn in MS Paint by a person with half an arm. Anywho, I found it boring. If you want an intro into LGBT in anime though, this is your go to.
Now if we want to talk about something very cerebral and powerful, Black Butler's Ciel Phantomhive is our guy. A lot of people see his romp through gender in the first few episodes as a reflection of drag, or an excuse for man-in-drag humor. Well, there's a lot more to it than that. When I was coming out to myself, I was incredibly transphobic to myself, saying that "I can't be a girl. It's not allowed". This mindset kept me from my own truth for 13 years. Ciel is very opposed to many things he defines as feminine and un-manly. When he has to infiltrate the party of a perverted count, he dresses in a frilly dress and pigtails. We can see how uncomfortable with it he is at first, squirming and complaining. Later in the series however, he comes to embrace parts of it. He wears clothes that could be considered androgynous, embraces a feminine side, and becomes quite the diva.
I like to think of the first season as a reflection of Ciel's mental state. He lives the first couple episodes blissfully, as a Cisgender male. In episode 4, he "dons an evening gown", and allows the possibility of this other sex. I remember doing this very briefly at a young age, considering being a female. To be perfectly honest? It freaked me the f*ck out. I was terrified of being who I was, so I ripped the idea from my mind. This is exactly what happens to Ciel. The only difference is that when I thought I might be female, I wasn't almost sold on the black market like Ciel.
Later in the season Ciel allows the possibility again, through subtle remarks at his butler, servants, and peers. He realizes that there are deeper levels to his psyche, and without spoiling anything, he confronts his traumatic past in a number of ways. One major piece of evidence is when the theme song changes midseason. Originally, the opening lines of the song say, "The monochrome blows
Through our colorless encounter. I shall entrust each of my pains to you." Later in the series, the opening lines change to, "Since then, I've actually come to like the night. In a sea of dependence I forgot even to breath." If that doesn't convince you, nothing will. Ciel is a Trans woman, like it or no.
Another awesome example of a Trans female in anime is Chihiro Fujisaki of the Danganronpa franchise. This is a slightly more to the point story of Transgender psychology. Chihiro Fujisaki is one of the many students trapped in the hellish prison school of Hope's Peak. Chihiro is "the ultimate programmer", having created game changing software and programs. Chihiro is also biologically male. We don't know this until she turns up dead, and the only reasonable cause of this was someone in the Boy's locker room murdered her. Chihiro got into the locker room using her birth sex as an excuse. This is something I myself have done in the past in order get myself out of sticky situations.
Chihiro is also known for being very socially awkward, depressed, and kind. These are all characteristics very common of teenage Trans females. I myself have fit each of these categories. Chihiro is a perfect example of a passable Trans woman flying perfectly under the radar until being looked into further. If you knew how many Trans people would kill for this, you'd realize how truly rare Chihiro is as a character.
Chihiro notably built herself what is known in the programming world as a "Construct". For those of you unaware, a construct is a direct copy of the users brain, rewritten via computer code. "Alter Ego", as she is called, is a version of Chihiro built to protect and inform the other students. Now, if only I had an artificial intelligence to answer peoples stupid questions about being Trans!
Of course, on the subject of Trans anime, there's enough transmisogyny to go around. Let me show you some iconic anime clips you may not have known were transphobic;
Naruto's "Sexy Transformation"? Transphobic.
Ouran High School Host Club's Over-explanatory Lines? Transphobic.
Black Butler's Pronoun Butchering of Grell? Transphobic.
I hope this has informed you on the potential of Trans people in anime. I highly suggest you check out shows like Black Butler, Ouran Host Club, and Danganronpa. There's so much more on this topic I want to bring up, but will save for next time (i.e. Trans*). I'll be back next time for more queer anime articles, but in the meantime, TRANS PRIDE!!