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.
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
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.