The pain of the small cage and a plug that was 2 sizes bigger than you were used to was almost too much, but the pure pleasure you were feeling from the rush of arousal was enough to keep you going forward with your training.
Finding a friend who was also into chastity was amazing, her ability to be super cruel and leave you locked for days or weeks on end without anything except being teased the entire time, however, was slightly less awesome. You were almost regretting tell
She dressed you up in her old uniform and took your photo. You looked different enough, but people who knew you would know it was you. She then used these photos as leverage to get you to do more and more humiliating things until finally she locked you i
These days the girly looks and the cage were just part of the normal attire your mistress expected of you, however the leaking in the cage that was constant, was punishable by a whip, cane, or longer sentence. It all depended on her mood.
