For what it's worth, I didn't peg Serendipity as a prostitute, I thought she was just someone's fuckbuddy who had been magically reassigned. For me it wasn't "ha ha let's mock trans folk" it was "imagine how people in this setting use magic for sexual gratification". Like the joke about Anders using electricity during an orgy earlier in his life.
As for portraying trans people as having distinct gender fluid traits, or some tell that causes that character to stop passing; I don't know how much of that is socially prescribing how to view trans people, and how much is just a simple comedic outcome around things that we recognize as trans-related. In the same way that we might portray a group of men or women as having comedic characteristics, without necessarily prescribing that you should view all men as grunting apes who gather around cars and grunt at them, or women as shrill, cackling harpies sharing gossip and passive aggressively competing with each other.
A part of comedy is poking fun at our differences. I take the Serendipity joke to be poking fun at our differences, without the condemnation or intent to demean that I believe is being tacked on. The problem is not that trans people get depicted as prostitutes, since we know there are trans prostitutes just like we know cis men and women can be prostitutes. The problem is just that they don't yet get thrown in any other roles. In the 70s there were arguments that black people were only being shown as a part of the criminal element, nowadays when you see black actors playing criminals, you don't jump to racism because black actors also play world leaders, family men and women, God, pilots, executives, labourers, so on. I'm not going to lean on prostitute being an arbitrarily negative representation because I think sex workers probably receive more than enough social condemnation and judgement, but certainly it's becoming stereotypical, a little rote, and I think people are ready for trans people to show up in different roles. I don't want it to become "isn't it time for GTA to have a trans protagonist" or "I'm taking a star off this game because it doesn't have any trans people in it" and I'm sure most reasonable people would agree, but I think a television show for instance would have a huge competitive edge if it were a family sitcom in which one of the kids is trans. But of course I would see that as a competitive advantage.
It may have been because I was high at the time, but I thought the trio of trans prostitutes on Bob's Burgers were awesome. Even though they smoked crack, they just seemed like nice people, which you wouldn't expect from people on the fringes. Plus, one of them was Jack McBrayer. Which I guess explains the niceness.
I wonder if switching from a very feminine voice to a very masculine voice, or vice versa, was the world's first gender fluidity joke..? Or, person looks very feminine but has a super masculine voice or vice versa. Like that scene in Mrs. Doubtfire where the guy tries to steal Robin Williams' purse, and he responds first effeminately and then "GET THE FUCK OUT OF HERE!" in full dad voice. I wonder neurologically, what elements of a person we use first to determine gender, I feel like face and voice are the top two. The more extreme the difference is, the larger the incongruity, is where the comedy comes from. Breaking expectations itself has comedic elements to it, especially if it all still makes logical sense. When people play Saints Row and make big beefy guys with massive survivalist beards and then give them the effeminate lady's voice, it's not to demean transgendered people, it's to have fun with the incongruity.
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