My wife and I have been playing with chastity for a few years now. About three months ago, we agreed to go full-time with chastity and we laid down several rules that I would follow. For her part, she agreed to enforce my obedience through punishment (not defined - left to her choice). We also put an out clause in the agreement with the understanding that if either of us opts out, we are done with chastity for good and we won't re-explore it. For her part, she can basically opt out at any time that she chooses if she feels that I am not behaving properly. I was given two outs: one after the first three months and then annually on my birthday. After a rough start where she punished me on a regular basis for rule infractions, I settled into the 24/7 arrangement. Honestly it was difficult at first and because I thought I could sweet talk her into things, I didn't respect the rules. She has since made it clear that she is in charge and, while I am now constantly horny, it has made it easier in many ways because my mind isn't thinking about how to get out of the situation. By the end of the first three months, we were pretty regularly fooling around (with me locked in the device) on a a near daily basis. Contrast that to once a week or every other week in our pre-chastity days. When the end of the three months came, I was feeling a bit conflicted. On one hand, I wanted to relieve myself and on the other, I enjoyed our new relationship. I asked her what she wanted and she said that it should be very clear already that she enjoyed our new situation. She said that if I wanted out that she felt we would slip back into our old patterns that didn't satisfy either of us. She also said that even if I wanted out, she would expect that I would still obey the non-chastity rules and she reserved the right to crop me for disobedience. In her mind, the chastity part was disconnected from the obedience part. After a bit of a long day trying to decide, I gave her back the keys with the lock untouched. She told me that she knew I would make the right decision. She let me please her and then afterward she used the crop on me because she didn't appreciate my wishy-washy behavior about the chastity and how long it took me to do the right thing. That was about a week ago. Now I am in for another 7 months and at her mercy for releases. Last night, she has told me that if I want the same level of releases (roughly monthly), I will need to step up my behavior. She has also told me that she thinks it is a good idea to have weekly evaluations of behavior with discipline sessions so I can learn to better submit. I'm not a big fan of punishment and she knows that but I'm hesitant to question her because that is one of the rules on the list and I know from past experience that she will punish me for questioning her. I am going to go with the flow for now but if it gets too much, I will need to talk to her. Even with the rules, it's a mutual agreement.
Sounds like a good start, and a good arrangement to me, and it sounds like she is really getting into the "swing" of things... Maybe suggest that during the evaluation meeting you be allowed to speak freely about any desires, concerns, etc. That would give you an opportunity to address the issues that might hurt the long term relationship.