00:54:06 | 1280×720 | mp4 | 919 MB
Sissification is at the center of Miss Jess’ fetishes. She grew up with a sissy and understand the psychology inside and out. So one of her favorite types of privates to do is with a person exploring this kink for the first time. In this extended recording a private show, Miss helps a first time sissy come to terms with their desires and explore different aspects of being a sissy. She picks out panties and a cute (and pathetic!) dress, and set of panty hose, and verbally role plays how she would coax and finangle and persuade you to put them on for her. She just wants you to look cute, after all! If a pretty girl asks you to do it, it doesn’t really count. In fact, isn’t it kind of fun to play act as one of her girlfriends and give up that big strong man act for awhile? Of course, being a sissy isn’t just limited to the costume. The most fulfilling part is embracing your inner slut, and Miss gently encourages her first-timer to play with their ass, stroke and rub like a girl, role play getting pegged, and ultimately lick up their cum. This is the longest sissy video that Miss Jess has released and showcases her playing with fantasies and fetishes that are near and dear to her own desires. If you’ve enjoyed her shorter sissy instruction videos, this one goes deeper to show how Miss plays in private with her girls.
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