Tenta encerrar a v0.15.50 primeiroThe dominatrix path was there from the start under the "Forceful Path" when you fight Lucy when she catches you in Mom room and do not forget she "raped" you in the shower. Also here is a post I did with the path for Lucy I was going to follow:
https://f95zone.to/threads/bobbys-memoirs-of-depravity-v0-15-491-ziptiefun.130448/post-10759666
Also as far as Ms. Anna becoming a slut suddenly, well you need to play about 3 to 4 hours of the game to get to that point. There is also some back story you will get from Evelyn about when she and Ms. Anna was growing up this will be part of pool party events. And don't forget she was nearly sold as a sex slave so that may affect her as well .
As I stated before there is still alot of backfill content to be put in to expand out the game as it is still very empty. Sadly I not running out of ideas instead I have too many ideas and not enough time to add them in.
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# I really think you should take a step back, take a deep breath and come to the conclusion that you must focus on finishing v0.15.50 asap. Make it leaner, bug free, loose ends free and then, only then, start new events (in a new chapter/game perhaps...). You know better than this. This is killing the game.