Great, I just edited out a huge part of my post trying to fix editing. So, short version:
I actually like that, and here's why.
This is an actual psychological compliance technique, and is used in negotiations everywhere, from business, to interpersonal, to political. It's the "door in the face technique" opposed to the "foot in the door technique" which is what I've been mildly advocating so far. It's where a major request is made, in order to make a later (desired) request seem more reasonable by comparison, and likely to be accepted.
Basically, it simulates this: the captor wants the PC to submit to, say, wearing the collar. So, the lead-up is requesting the PC to whore themselves out for their captor, which the captor knows will be rejected out of hand. But, by making that request first, wearing the collar will seem a more reasonable concession to ask by comparison, and it's more likely the PC will accept it. But, by accepting it then, the captor knows the PC will end up habituated to obedience in the long run, and will eventually submit to being whored out anyways.
Whether or not it's a fun game play mechanic is up for debate (I think it is). But, it is realistic, and contextually consistent.
That sort of idea is what I was thinking of setting up for with the random demands for slave levels. Set up the player to choose what they perceive as being the lesser of the evils in order to avoid punishment or curry favor. That isn't really the problem with the event chain that Mario is bringing up.
The problem in that case is that there actually is no player choice or no stat checks in the event. It's a punishment scene that may randomly trigger if your punishment points are too high and causes a massive amount of willpower damage. If your captor then randomly decides to demand your next slave level event immediately afterwards, you have no choice because of the really low willpower. Punishment points can be randomly accrued through no fault of the player as well, so it is entirely possible to suddenly go from perfectly fine to the next level of slavery in three turn ticks without the player having ever made a choice purely due to random chance. It's mainly an issue with how the events play together and that there's nothing stopping the captor from triggering events over and over again in short succession.