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.
You knew they were also locked when they asked to lock you up, but you had no idea they expected you to match the time they already had in their belt, and since she was Ace it wasn't difficult at all for her to last the 3 years she already had.
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.