She dressed you up in her old uniform and took your photo. You looked different enough, but people who knew you would know it was you. She then used these photos as leverage to get you to do more and more humiliating things until finally she locked you i
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.
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?
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
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.