Here is my guess : you have to turn femdom on play until you lose then turn it back off. If you want to see the MC get punished. Earlier game versions only had femdom on/off variable and there was no separate setting for MC punishment. So it might be a part that still uses femdom on /off to determine whether the MC can get punished or not.You must tell Chloe that Emily will watch the spanking at midnight, if she says no then do it 2 more times and she will allow it.
Now for my own problem.
I have femdom off because I hate that crap.
How to get the spanking for MC in the quest/event "Aunt Makes Mistakes" View attachment 373338 I have won all options now at least 6 times each with no lost at all.