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.
She said she had never cum from oral before. You thought you could prove her wrong so she bet you that you couldn't do it, and would be locked in chastity until you made it happen. Perhaps you were too confidant in your abilities. You thought you would
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.
The cage had been locked on for months now, you could no longer take it and started signing up on message boards for anonymous meetings in public. You hoped they would give you pleasure and let you cum, but more often than not, you were just a play thing