In my last play-through, I found that I was experiencing the same issue that
Apartment817 mentioned: I would choose "hold it" but the game would progress Emily's story as expected.
I resolved it by using the wait-time functionality to skip ahead in time and then immediately going to bed with Emily.
Also note, it doesn't have to be exactly 10:00 pm. I just chose that time since it's when Emily goes to bed.
If you are willing
spiegelbild, can you test the original save again? But this time, do
NOT use the wait-time functionality at all to move forward in time. Instead, just have the MC sleep to make the time pass.
Without the wait-time functionality, are you able to progress Emily's story normally or do you get stuck at handjob/blowjob?