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.
The hard plastic cage covering your privates didn't let any sense of feeling through, but for some reason you tried to still tug on it even if you knew it was a hopeless endeavor.
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.
Always wondering what it would be like to be a woman, you didn't believe what the packaging on the dildo said, but you decided to try anyway, after all, what harm would it cause?