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Yes adding in new random events for keyholder specific isn't that hard. There are currently 4 random events (currently 35% chance a day if there isn't another daily event already) and could easily change the chance or add more events into the pool. I was thinking I wanted some events where the player has to think about it a bit harder, as generally they are pretty easy to fulfil now with little drawback or risk.

As for genders that does need improving. I largely tried to keep it gender neutral but after coming back to it after a few days I realised the events don't work nearly as well with a female chase and male keyholder.

I like the idea of being made to serve the keyholder with a loss of all slaves obediance and some more gender specific stuff would be good.

There are a bunch of great ideas here that I would like to implement. Next time I get a chance to work on the mod again I'm going to come back and implement what I can from here. Most of the ideas I think will be fairly straight forward to implement. Hopefully I'll get some time soon this week.

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".