Tag: sissy training

CEI for Lipstick Sissy Mimi Penny Barber

Does little sissy Mimi want to cum? How badly do you need it? What if I have certain conditions. For one, you have to be wearing these silky soft pink panties that I just got from Victoria’s Secret. Two: you […]

October Sissy Lesson Penny Barber

October is here and of course that means Halloween themed sissy assignments! Obedient sissies will have some slutty costume shopping to do and plenty of sissy treats to eat. This clip includes a little mutual masturbation with Mistress fantasy to […]

Sissy Sports Failure Penny Barber

I should have know you were too timid and dainty for the football team but I never thought you would embarrass me by crying and running away like a wittle girl in front of the whole team and the cheerleading […]

Sissy Lessons Cam Slut Penny Barber

In this lesson you lucky sissies get camming instruction from a truly talented professional, Mistress Penny. Not bragging, just the facts ma’am. Tips on everything from flattering angles to lighting to handling pushy clients. Even if you just want to […]

Back To School Sissy! Penny Barber

This month’s theme is Back to School! That means sissy schoolgirl skirts, Hello Kitty notebooks, and trips over Principal Barber’s knee! FORCED FEM, FEMINIZATION, SCHOOL UNIFORM, SISSY TRAINING