I don't want to go around saying that there's a right and a wrong way to do it, when you start from that premise you'll usually end up saying that there's only one right way and I've never been okay with a particular (usually unaddressed and unaware) prejudice that many who end up there have against other cultures' depictions of androgyny. Way too often I've seen people pretentiously say that the japanese for instance are 'behind' in their representation and portrayals of trans people and it's like...behind who? You do remember how, less than 10 years ago, western game companies were still aggressively scrubbing away any and all queer characters from japanese games, right?
The way I like to judge these things instead is tone and storytelling choices. Whether the particulars of it align more with trans, futa, otoko no ko, sissy or whatever else what I look for is the erotic theme behind it and the tone it takes first. If it's immediately and visibly about emasculation and the tone is very dehumanizing, sadistic in a way that phrases the state this character is in as some failure of manhood then I'm taken out of it. There have been instances where I felt that was done well, and that's where storytelling choices come in, but what I immediately think of is the generic twine sissy game setup where some porn-addicted self-insert loser gets bullied into acting like a slut.
Even keeping the emasculation theme in play there are much better ways to do that. One of my favorite futa/trap games is Pandora's Forest, and that works by not treating it strictly as emasculation. There's some inherent androgyny in the fact that, like in a violated heroine game, you need to protect the hero's purity/chastity to some extent and corruption is not strictly sluttiness but also some feminine things, such as crossdressing, having different parts of the body 'developed' to be made more sensitive &c. There are both advantages and disadvantages to these things; it's not strictly good or bad to increase them. In other words it's not just phrasing it as having masculine purity taken away from you and being left weak and emasculated, there's a strength in feminine corruption that only results in failure if, in chasing it, you lose yourself to it completely. It's totally possible to make a great game from a theme that I don't usually like.
What I would like to see more of are these interesting, well-developed ideas/themes rather than specific takes on it ("it has to specifically be trans or futa and it has to be fully supportive or totally not gay" or whatever). I won't say I'm not biased against the coddlingly sweet games you might find on itch or the overwhemingly negative ones you can find on TFG, I've seen them go down the same well-worn roads that make me roll my eyes more often than not, but what I want to say is that you can make a supportive-in-tone game that doesn't treat the readers as fragile and harsh-in-tone games that aren't just "now put your dick in a box while stolen porn gifs laugh at you".
