On -isms: Let's Talk Trans
My experience with transgender people at the time was effectively nil. I had had gay friends and associates for years, but I had never known (to my knowledge) anyone who identified as a gender other than what they had been biologically born as. The closest to knowing a transgender individual I had come was seeing cross-dressers on television. And, if you're at all familiar with trans people, you'll know that that's roughly the equivalent of saying that you're familiar with geese because you saw a cartoon where Bugs Bunny put on a duck costume.
So going into that conversation, my knowledge and experience was based on nothing resembling reality. I didn't know that at the time, of course. Chalk up my ignorance to growing up in a town that wasn't all that different from Mayberry. (Seriously, my best friend's dad was the chief of police and our postman was also the mayor.) It seemed as if the rule of the day was that things were great in the 1950s and there was no reason to go on screwing that up just because a few decades of social change had taken place in The City. But the bottom line is that I was an ignorant and somewhat arrogant ass on the subject of transgender folks well into adulthood.
But even though I didn't quite get what my girlfriend was trying to tell me about the issue, it did give me pause enough to look into it more. I don't recall if I started actively looking for comics that discussed this, or if simple awareness made me more prone to noticing it, but I started coming across some webcomics that were written very much from a trans perspective. In reading them, I don't claim by any stretch to fully understand all the issues surrounding gender identity but I'm certainly more cognizant and appreciative of some of the bigger issues after having read them. So I'd like to take a moment to point you to some webcomics, if not exclusively about transgender issues, that discuss them in some capcity.
As the Crow Flies by Mellanie Gillman
The protagonist is actually "a queer 13 year old girl" but one of the friends she makes at camp is transgender and is hiding it from pretty much everyone else.
Assigned Male by Sophie Labelle
"The incredible adventures of Stephie (who happens to be trans)"
Empathize This by Tak
Although not exclusively about gender issues, they look at real-world stories of discrimination and isolation based on superficial issues.
Mock Girl by Terra Snover
"The story of a transgender girl (Sam) who moves to a new town where her life goes nuts, dealing with the mob, crazed reality stars, and more. Everything that can go wrong seems to do just that."
The Princess by Christine Smith
Although the strip hasn't been updated since 2013, it highlights a very self-confident young girl whose mother doesn't understand why she can't just be a "normal" boy.
Questionable Content by Jeph Jacques
It's one of the long-running classics of webcomics these days and has a broad cast, but the protagonist Marten has recently started dating the transgender Claire.
Trans Girl Next Door by Kylie
Comics about the author's life as a trans-girl in her 20s. Straight-forward and honest material here.
Transchizophrenic by Tresenella
"A webcomic about the life of Sarah, an introvert trans-girl who has to face gargantuan problems like dealing with family, overcoming boredom and procrastination, and going outside her room to engage in eventual social interaction with other human beings."
Validation by Christian Beranek and Kelci Crawford
"Validation is the story of Ally, a transgender girl doing her best to live a fulfilling day-to-day life."