I like the idea of Derek being so naughty and greedy that he’d have to get himself off as a wolf; I don’t think a cock cage would stay on during a change but I def think they would both love the thought of Derek getting disciplined and not having the freedom of touching himself whenever he’d want…
Maybe he gets all hot and bothered when he sees the little key to his cage around the Sheriff’s neck; or watches him stuff the small chain beneath his shirt before leaving for work, knowing that he has to wait for the Sheriff to come home in the evening.
I don’t think the Sheriff would be terribly angry at him disobeying, though; it’s all just in good fun, after all, and they both enjoy the discipline part so much ❤