There's a free web series called Her Story that's about two trans women, one who's starting a relationship with a man when she's outed publicly, and another who's in a relationship with an abusive and controlling man, who leaves him for a cis woman, with a cameo from her trans lady indie musician ex. The trans characters all have trans actors, and a trans woman was involved in writing it.

It's usually not my type of thing because there's no sf/f element, but I watched it anyway because there's so little trans content and it was short, and for some reason it stuck with me. (I would watch a Violet/Bad Penny prequel, too!) It tries to explore how trans women's relation to their gender and dysphoria affects their relationships and who they feel comfortable with, such as Violet being attracted to women, but feeling insecure and body-conscious around cis women. It can be a bit roughly sketched out in characterizations, since it's hard to build up characters in that little time, but those parts had a certain realness to them.

Official site, entire series is on YouTube: http://www.herstoryshow.com/