Phase 1 of chastity is playtime. Lots of little 3-day lock-ups. "Extra cruel" is saying no, keeping him locked a 4th day, for a thrill.
Phase 2 means pushing for more. He's so proud of a week locked. You're exploring how different oral might be from a chastity boy.
Phase 3 really begins once he's passed the 10-day mark. He's surprised to discover he doesn't need out. Maybe doesn't even want out. (Don't take it personally.) This is a good time to start compiling lists of chores and such you can keep him busy with when caged. Because he's starting to ask to be locked more often, for longer. Oh, and threats of chastity rev you both up when you DO have sex.
Phase 4: Two-week lock-ups are a regular thing now. Or maybe you release him for a fuck, then lock him right back up because it feels hot. You get oral on demand. Try out things you wanted that he "wasn't into." He wants to serve? Let him. Oh, and... don't let him out because you feel some guilt. Ask him. He doesn't want that.
Phase 5: You break the month mark. It's up to you. He can't make it without you keeping the key and directing all his hyper-productivity. The erotic intensity of a cage-ruin or a milking makes him realize this could be a lifestyle, not a game. Which is funny, since he can't turn back now. Because you won't let him.
Phase 6: Permanent or at least semi-permanent chastity where you'd count days Out rather than in. His lust for you is never-ending. Your pleasure is ever-available. You both find unceasing joy in his enslavement.
So ask yourself: which level have you reached? How far would you like to go?
Then sit him down and ask him how far HE wants to go. It's good to know where he *thinks* his ceiling is.
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