What was hardest for your partner to do?

Once your partner has put you in the lock, what is the hardest part for them to do so that your chastity experience stays as pleasant as it can be? Clear and open communication are key to ensuring everyone agrees. For me, I struggled quite a bit getting my wife to tease from outside our sexual encounters. She wasn’t used to randomly feeling me up during the day and felt awkward doing it at first. I had to negotiate with her to get her on board as more of a flirt/tease, though even after that she still found it challenging. It’s definitely an ongoing process, but she is really making an effort to please me. How about you? Did you have any particular difficulty getting your key holder (KH) to do something for you?