In this clip, Miss Jess meets a cute submissive and is flabbergasted when she realizes they've never played with their ass before. As a sissy, its so important to put your asshole to use - its your sissy pussy, after all! Miss Jess takes the opportunity to train her sissy on how to use their ass, sucking a dildo to get it wet while slowly playing with their hole and working a few fingers in. Miss Jess instructs her sissy how to play with their prostate while she plays with her own. Sissy can't handle it and ends up making a big cummy mess all over herself, before licking it up for Miss on camera. This is a great clip for any sub or sissy who's curious about anal play and wants Miss Jess to hold their hand for their first time putting their boi pussy to use.