In this video, Miss Jess helps yet another shy sissy come to terms with their kink. It starts like so many other sissy stories, a married man with a dirty side, secretly wearing his wife's panties to please a mistress. Miss Jess directs her new sissy to masturbate inside the panties, while worshipping her ass, removing a buttplug with their teeth in order to clean out the real man's cum from Miss' asshole with their tongue. The show then transitions into a role play, where Miss fantasizes about taking her new sissy shopping. She's going to take her sissy to buy panties at Victoria's Secret. She waits until sale day when the store is packaged with people, then asks the male clerk to measure her for panties in front of the crowd. Her sissy is too embarrassed, and they end up in the backroom for measurements. One things leads to another, and before you know, sissy is on all fours with Miss's strap-on up her ass and the clerk's cock down her throat. Everyone can hear what's happening from outside the changing room, and so there's a big crowd waiting when Miss Jess makes her sissy crawl out of the dressing room with cum on her face. The crowd of girls is laughing and taking pictures, but sissy still needs to pick out a pair of panties, and has to march around the store picking them out with her face covered in man glaze. This is a hot roleplay for new and curious sissies who are curious about the lifestyle and want to fantasize with an experienced sissy mistress.