Tag Archives: Sissy Training

I met this boy for a session, and he said we can record it and make a clip out of it. So of course, I said yes! You can tell …

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. …

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 …

After catching sissy Sharon sniffing my panties and spinking her bottom several times I decided to take out fun play time to a next level. He is an obedient sissy …

Governess Miss Zee arrives home early, and she catches her neighbour boy dressed up in his sissy attire and sniffing her panties! She knows about his weaknesses but did not …