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You gave already some rules to your submissive/ having already rules from your Master?

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I don't have a master (yet) but I did give a rule to my Sub and I was given the option to collar them, which I did


For most of the time I didn't have a rule set but this does also extend to previous playthroughs when I did give subs rules and I never saw an option for chastity ever. It's why I assumed it just wasn't in the game

And I've had this issue across devices. Before I used to play on Mac but then switched over to windows (But I did not always pursue the library storyline either to turn assertiveness and compliance into dominance and submission so that may be messing with my memories)

Ok I know it's been a while but I'm just gonna hope you see this

On a new character I have reached level 10 assertiveness (w/o cheats but I have it set to increase skills and relationships at a faster speed) and then  did the smith library tasks to unlock dom/sub skill 

I haven't gotten past the just unlocking that skill option part just yet though. When I went to my subs there was no option to put them in chastity, even the day after or if I owned chastity to match them. Is there something I'm missing? Is there a specific event I need that I just haven't run into yet because I kinda struggle to stick with one character (I'm getting better at that though)

Try gifting the right chastity device to your submissive, tried looking at the code, but i didn't find any relevant event to unlock it..

I have tried it before but it does not appear as an option to be gifted for me. Either when I'm talking to my sub or when I try to purchase a new chastity device.

I also double checked the rule thing by seeing if it might be different and the rule might appear if I do it via text and it does not. Should I just do like a clean reinstall and see if that might help? I have never seen it as an option even though I know it is supposed to be one.

My subs behavior with rules also do not change. They do not change their clothing if I tell them to except maybe with the collar and underwear (but underwear can be iffy and they may still disobey). They do not have any brat inclination either. I'm aware this is a separate issue but maybe my game is just broken?

Try to ask in Discord, the Devs or Community usually are friendly & if you think there's an issue a save file and a bug report will solve it and trace a possibly bug..