Mistress Jolie wanted to turn this guy's chastity humiliation into a hobby and that is exactly what she did. She did not want to let herself down and that is why she did what she had to do. She used her chastity humiliation to pass a message to him and to dominate as well as degrade him. He cried but she did not care and she had him do it all.
Mistress Jolie wanted to use chastity humiliation to get her way and that is exactly what she did. She did not care what this guy felt as all she wanted was to humiliate him and take advantage of him. She had fun having him wear a chastity device and then teasing and denying him and it was super fun for her but it was torture for him. There was nothing much he could do about it.