This clip showcases a scenario that has played out for Miss Jess many times in her life. She meets a cutie who is a little curious and a little kinky - they love buttplugs and playing with their ass, they're curious about wearing panties - but they've never fully explored their kinky side with a real Mistress before. Miss Jess takes that curiosity and open-minded kinkiness and ruthlessly exploits it to push her visitor down the path to being a sissy. She refers to them only as a girl, she roleplays them modifying their appearance and haircut to appear more feminine, she teaches them to use their nipples and their holes for pleasure, and she ties all of these things to their sexual arousal. For Miss Jess, sexual gratification comes from taking a "man" and making them pathetic, robbing them of their manhood, and ultimately turning them out as yet another cock-hungry sissy slut, and this process is on full display in this video. Once you've gone down this rabbit hole, there's no going back - you've been warned.