Tag: feminization

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 […]

Pantyboy Humiliated At Camp Penny Barber

Getting caught in a girl’s cabin is bad enough but it looks like you were on a little panty raid too, huh? Was it a dare or were these for your personal wanking enjoyment? Does not really matter because the […]

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 […]

Little Sissy Wank-A-Long Penny Barber

Does the little sissy want to cum for Mistress? Of course you do but before you cream your pretty panties I want you to follow along as I play with myself. When I stroke you can stroke but remember Mistress […]

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

Cosplay Princess For Mistress Penny Barber

How much would you love to be my comic con sissy date? Dressed up as a little Disney Princess with your stiff, leaky clitty hidden under your puffy skirt, white stockings with pink bows on your legs, and sweet little […]

Sissy Lessons Clitty Pics Penny Barber

Listen up pantyboys it is time for a very important Sissy Lesson. Today I am going to teach you how to take clitty pics and sissy selfies that Mistress actually WANTS to see! Remember what is most important is attracting […]

Sissybaby For Halloween Penny Barber

Hurry up silly, it is time to put on your costume. Oh you thought this cute little dress was for me? Nope, I will be going as a vampy Mistress and you will be my little sissybaby. Now hurry and […]