Tag Archives: Sissy Training

Maid Missy and sissy maid Jesse have been slacking on their chores around the house! Miss Sephie makes them hold up their skirts whole she spanks their naughty bottoms side …

I decided to introduce a sissy evening routine from now on. That means a nightly inspection – teeth, oral hygiene, hair, and clothing. This sissy failed on multiple levels. The …

Featuring Sam Johnson as Mistress Samantha and Maid Bettie . Mistress Samantha notices a large amount of money missing from her handbag and suspects her sissy maid of stealing it. …

What happens to arrogant and openly sexist boys in my school? See for yourself and bear in mind that this is not an old fashion institution but a modern school, …

After plugging his bottom and putting him in a chastity cage and diaper, step mommy takes Max over her knee for an embarrassing, uncomfortable spanking. She scolds and teases him …

You are late to your tutor who discovers that you are carrying around ladies’ lingerie in a plastic bag instead of your learning materials. To make matters wors your excuse …

Mestra Jussara and I are trying to shoot some promo reels for social media. Jussara is My good friend from Brazil. She is in New York because We love to …

Mommy has laid out all your sissy gear, with a pacifier and a lollipop for you to practice sucking on in preparation for our cock sucking training today. I know …

Caught on webcam! Babysitter Alice & Katherine spanks & diapers you while Alice’s friends watch on a live video stream! – HD 1080 Mom Katherine is running errands and at …

I live with my absolutely bonkers Aunt. She got it in her head that she can turn me into a girl, because she likes girls more than boys. I have …