I can't remember the name of it (not very helpful, lol) but it was a game where MC lived with a guy who is transitioning to a women and she (the roommate) was working at some company for trans women. Had a personal trainer, a doctor (or scientist) and a librarian lady. Also had the head lady. And a banker (who was satan, or something). Not really my thing, but it was pretty neat.
and i found it.
https://f95zone.to/threads/sissy-maker-v2-91-sissy-maker.1310/
Drawing My Life is another. There is a path or two with helping your "roommate" transition, i think there is an option for another character too. and there are a few ladies with dicks in it too. If you play this one, be sure to download the intro and s1mo1 (in the OP) before playing the latest version. or you may get confused and will miss content.
https://f95zone.to/threads/drawing-my-life-s1m02-v0-6-five-against-one.12650/