You always thought you had problems with being insensitive down there, however, it would appear you just jerked off too much and lost sensitivity, 2 months in chastity fixed that.
Hypnotism never worked for you, but listening to it and fantasizing while doing it was hot, that is until you listened to the chastity swimsuit stories. Next thing you remember is being locked in a chastity cage and having new bikinis, you didn't rememb
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.
It never occurred to you that the reason your anal plug kept changing patterns was because your girlfriend was live streaming you all gagged and locked, and the audience was controlling it.
You never expected your house maid would find your key and then blackmail you to stay her little toy when she caught you wearing your cage and took some photos. If you fired her, she would just release the embarrassing photos.