The last thing is there anyway to add weight to the events? I was thinking that for some continuity instead of just picking an event at random they could have some sort of weight scale. Say every time you get a event the result adds a point. For example if you complete the event you'll get +1 submissive point, and if you refuse you get +1 failure point. And have the events tied to that? That way it would play out like a little chastity adventure where the stakes and consequences ramp up the longer your in chastity. It could also play in to what you were saying earlier about having different modes. High submission will make the key holder more lenient and will trade orgasms for more days in chastity, and higher failure will make the key holder more cold and strict. The hard part would be real consequences. For the submissive it could be something easy like a trainable traits, something that buffs the head girl position so you won't feel obligated to do it on every slave. And if your failure gets too high you could get a game over, something like "After you constant and repeated failures "owner" has decided to trade ownership of your brand to someone who will be more thorough in your training, you spend the rest of your days as a chastity slave".