Tag Archives: Older Woman / Younger Women

It was a simple mistake, but in this old-fashioned office, standards are not negotiable. Miss Zee is to the outside world, the very definition of refinement, impeccably dressed, measured in …

Winter thinks she can escape her chores and hit the town in a ridiculously slutty dress, but her mom, Samantha, has other plans. Catching her bratty daughter trying to sneak …

Mischievous cousins Sarah and Matilda are caught red-handed riding the luggage cart up and down the hotel halls, drawing noise complaints from other guests. Shocked mothers Miss Iceni and Miss …

Lady Jose entrusts her home to Willow as house sitter, with simple tasks like watering the plants, bringing in the mail, and ensuring all is well. After completing her duties, …

In this hour special custom long film, meet Dr. Sarah, a former newly qualified nurse under Matron who later in life becomes Matron’s superior. She is young and ambitions but …

Miss Mathews has caught the new student, Olivia, trying to cheat on the upcoming English exam, and doesn’t think she acted alone. Pointing past a similarly downcast Helen, Olivia identifies …

Marianne failed to show up for class today, once again shirking her studies by feigning illness. Unfortunately for her, she’s even a worse actor than she is a student, and …

In part 1, Lizzie is being punished for flirting with the boys and letting them take liberties with her body. When her knickers come down for a bare bottom spanking, …

Georgina 1: Georgina is a new student here, about to learn the hard disciplinary ways of this school. She’s never been spanked, but that ends today with her first spanking …

Dolly’s reckless decision to wear inappropriate clothing to school has consequences she never saw coming. Sent home in shame, Dolly’s mom is furious, leaving work early to collect her wayward …