NOTE: This is just stuff that passes as romance. Obviously I've read infinitely more trans stories.
NOTE 2: This is just what I've read. Will add more as I read them.
NOTE 3: The title says it but this is just trans girl stuff! Comment any cool trans masc stuff you know though I'll make another list.
Note: A Safe Girl to Love is a collection of short stories, I think around ten. I only included the ones that I think qualify as romance.
A Safe Girl to Love (Other Women) by Casey Plett: This might be my favorite Casey Plett short. Is it because I'm straight? Yeah probably. I love this story, and I love Mark. He's exactly the kind of guy I fall in love with but only in retrospect. Wishing I could have tried to make something more of the few cis boys who'll have me. A lot of melancholy stuff throughout the story, the romance segments are very short. That's a running theme throughout this whole list which shouldn't be surprising to anyone.
A Safe Girl to Love (How Old Are You Anyways?) by Casey Plett: This one's basically smut with bdsm undertones. I like it. It's gay.
A Safe Girl to Love (Lizzie and Annie) by Casey Plett: This story might actually be the closest to a true romance out of all of Casey Plett's stories, but it actually feels the least like a romance of the three I recommended. It feels like a relationship trapped in limbo, in a “this feels very real and touching but isn't making me feel things” kind of way. Which is magical in its own right. This one's also gay.
The Chaser by Torrey Peters: The Chaser is my favorite piece of short writing ever. It left me wiped for an entire day when I first read it. The beginning is absolutely a romance in the most breathtaking and insidious way. I have a big soft spot for stories about boys who are definitely not boys trapped in that limbo between being a boy and being something else, especially in the context of not very healthy or clean cut relationships. This one's super heavy.
CisWorld by Torrey Peters: Ok this one isn't exactly a romance. But it does feature a very slapstick depiction of a het t4t couple in a way that's both hilarious, insightful, and troubling. It's fun.
If I Was Your Girl by Meredith Russo: Basically what if your teenage romance novel was trans. You don't really get to see the relationship develop too much which is pretty standard. Bonus points for being straight. Not really my taste but I'm sure someone will enjoy it. I tend to like my romances messier, ala The Chaser.
Note: There's plenty of trans webcomics that I'm sure are incredible. To be honest, I'm not very well versed in webcomics. Very much open to recommendations.
The Pervert by Remy Boydell & Michelle Perez: The Pervert isn't exactly romance but there are a few scenes that certainly fit the bill and give me chills. The entire nurse segment is extremely sweet, and there's plenty of other moments. This one's heavy of course.
Fanlee and Spatzle by Pseu Jones: Most twitter strip comics don't really qualify as a romance for me, but Psue’s stuff definitely fits the bill at times. It's all really charming.
920London by Remy Boydell: Not exactly a romance, but it kinda fits. If you can enjoy those not quite dating, not quite friends, definitely not super healthy but nonetheless there for each other situations, then sure this fits. Very melancholic.
The Lover of Everyone in the World by Beatrix Urkowitz: A beautiful, surreal comic about loving people. A lot of people. It’s really good, really sweet, romantic, and melancholy. Also it’s short.
There's not a lot of movies I know that are trans and center romance in any capacity, but also I'm not a movie person. It's definitely my biggest blindspot media wise. Open to recommendations!
Euphoria: Oh boy. Euphoria. I can't decide if I like Euphoria, I feel like I'm stuck in a limbo with it. You know when there's a piece of media you think you're going to hate a lot based on everything about it, but then you actually enjoy it? That's Euphoria for me except I still hate a lot of it. Still, Jules has a lot of great scenes. I also banged older guys for a bit, and the sort of superfluous bisexuality of the whole thing is something I can get behind.
Her Story: Short series on youtube, very romantic with straight & lesbian romances.
I should know more trans games. If you know any please tell me.[a] I can't keep making Gwyndolin fan comics forever.
One Night Hot Springs by npckc: The sequel in particular covers a trans relationship. It's mostly about the best friend figuring out she's ace though. Very very simple, but maybe someone will appreciate it.
Heaven Will Be Mine by Worst Girls: Had these in the honorary mentions section but yeah they do belong here.
We Know the Devil by Worst Girls: I'll write more about these games later.
It's no surprise to anyone that manga has a lot of trans stories that fit very nicely into the romance genre compared to their western counterparts. But most of it sucks and is in the danger zone section below.
Double House by Nanae Haruno: Double House might be one of my favorite mangas ever, and is a massive writing inspiration. The beginning is slow but wow, the dialogue later rolls so smoothly. Multiple lines gave me happy shivers and I love the dynamic between the main two. This manga is one of my few reminders that cis people can actually write good naunced stories about trans people.
Hanayome wa Motodanshi by Chii: Yeah, The Bride Was A Boy is the most run of the mill trans memoir you could muster. Still, I couldn't really not include it given it centers the author's relationship with her husband. Definitely qualifies as romance.
The Danger Zone
This is the stuff people might call dubious or just bad representations that I love nonetheless. A lot of this is manga, because there's not a lot of bad yet still genuine romances depicting trans ladies I've found outside of manga. Obviously, I refuse to call a story where the trans lady is dumped/murdered after revealing she's trans on this list, which is a lot of what I've found over here. Either that or the stuff I've found just doesn't center the trans romance in any capacity (I mean I don't consider my work romance. Maybe Staff Activities… but I wouldn't put it in this list).
The Flower by Takako Shimura: Takako Shimura is an all time favorite author of mine. I adore her work to death, and she stands as a massive inspiration for everything I make. Still, she really loves to tackle trans topics and fudge it up a bit. The Flower is a short oneshot about a trans woman flirting with a married man during a train ride. It's messy, it's understated, I love it.
Wandering Son by Takako Shimura: Yeah. Of course this was gonna be here. I love Wandering Son. I'm fascinated by it as one of the longest stories fully centering a trans girl I've ever read. Countless scenes completely blow me away, but it has a lot of flaws which drove me to put it down here. For one, one of the three older trans people you meet can be read as a pedophile which isn't great. The transmasc lead, Yoshino, absolutely gets the short end of the stick and has a pretty pathetic story past the first half. The story also dwells way too much on back and forth crossdressing without anyone putting their foot down, which after a while gets repetitive. I want to call Wandering Son unrealistic… except I literally began crossdressing due to being encouraged by theater kids I knew, and did so on and off for years before transitioning. Also I knew a lot of pedophiles. It's almost sad how much of my own life is mirrored in it's story. Still, the main girl's romance with Akira is really really sweet. I adore the ending.
Bokura no Hentai by Fumi Fumiko: Christ. I could defend not including the two Takako stories in this section, but Bokura no Hentai is nothing if not rough and flawed. The plots are corny, over dramatic, and ridiculous. The character's torture each other endlessly to the point that it gets fustrating. So why do I like it? Well… the Marika does have some genuinely incredible scenes, and I do like how naturally the characters fall in and out with each other. The story really picks up after the halfway point when the author finally decides to interview a trans lady. Go figure. By the way, my absolute favorite chapter if this manga is actually the Parou centric bonus chapter at the end. If you do decide to read, please seek it out. Oh, and this ones very grim at times. Sexual assault and pedophilia are both subjects, and I'd be lying if I said they were handled gracefully.
This section is for all those stories that are definitely not romances, but scratch that itch for me nonetheless.
The Red Strings Club
Nevada (by Imogen Billie)
Napkin (by Carta Monir)
Otokonoko Doushi Renai Chuu
Feast for a King
The Lover of Everyone in the World
Valerie Halla’s Porn Comics
[a]I have only played the first of these so cannot vouch for the rest (also mostly text games) but:
can you say my name again, by Nadia Nova - visual novel about being a trans lesbian, anxiety, and getting intimate and having sex.
Get Your Gun, Dragonfly - interactive fiction - sci fi love story between two trans women in a violent future-dystopian America.
why is this dragon so fucking cute??, by Nadia Nova - short visual novel about a dragon and a warrior, both are trans lesbians
Perseids, or, All This Will Go On Forever, by Freya C - twine story about four trans girlfriends going on a road trip to see the perseid meteor shower - ‘very little conflict, drama, no-one dies. Just a good time.’ (also worth following the link to the Trans Gal Jam and looking at the submissions for more games by trans women + transfeminine people if you’re looking for em!)]