MTATF is easy. Just keep a sissy in the dungeon for 250+ days straight. They will automatically accept 'You are a dungeon slave' idea, which unlocks the long-term dungeon agreement.
Now, for 'Clitmaker'. Put a sissy in chastity, an inverted one, that will make the progress faster. Requirements: 1 - 100% chastity endurance; 2 - 150 or more days locked in chastity straight. If these conditions are met, the sissy will accept 'You should be locked in chastity' idea.
They can also accept 'You don't need your balls anymore' idea on their own, this one has more conditions. When the brainwashing system is finalized, there will be a way to play game without planting ideas manually.
The game doesn't provide all this information, sorry about that. I'm still working on many aspects, and things are changing all the time. That's why I'm not making an in-game tutorial for now.
'1000 days' is definitely not working, it shouldn't have been included in the first place. I'm still working on challenges and overall progress, and many things will change in future updates.
Try all this and if it doesn't work for you - hit me up. Thank you!