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.
It's been 25 days of being locked up, at the start you swore you'd never suck dick, but a strap on doesn't count, right? Now that its the only way to earn release, you hope it still works.
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.