Bugs
I've noticed a bug with the secretary pill demo. If you decline to the do the demo, it seems to take you to the screen where your boss tells you about it, but it is bugged out. You can continue and do it, but there's no way to skip it once you are offered the demo.
I also think there might be an issue with being asked to do housework (or I'm missing something). After cleaning once, I'm never asked again. The only thing I can think of is that I started contributing to the household and maybe that means you don't have to clean?
Thoughts on the update
The secretary stuff is fun, but the Wordle game can be a bit frustrating, especially with the arbitrary extra tasks. Using 5 guess to start a word with P when you know the word doesn't even have a P is rough.
I really like the new scene where you have to ask Bill for his cum. I see a lot of people echo'ing this and their own suggestions. What I'm hoping for is that maybe if your character is horny enough or maybe has progressed in some other way, you might even start lying to him about needing his cum. Another idea is that maybe he has a harder and harder time getting off, so he asks you to do more and more for him (masturbate in front of him, handjob, blowjob, etc.). I know your roadmap has more stuff with him later, but these things would be amazing.