The Mean Roommate It’s a Sunday morning – why is Maggy wrapped in a duvet and sobbing her little heart out? Headmaster Tom is amazed to hear that Maggy’s roommate…
What A Mess Clothing on the floor, clothing hanging on the door and cascading out of drawers. This is the mess Headmaster Tom encounters when he cautiously enters Jodi’s room….
Private Pleasures Every woman has secret sexual fantasies, Private passionate thoughts. So few live out their dreams. Join Playgirl on an exotic adventure exploring sensual desires. A journey where a…
Keagan’s Punishment Obstinacy can lead to all kinds of adverse consequences. Just ask headstrong Keagan. When she committed house rules infractions one time too many, Headmaster Tom could take it…
Bridget’s Addiction Bridget has been summoned to Mr. Lewis’ detention room. The girl has been subscribing to lewd sites and has run up a $600 bill! Mr. Lewis punishes her…
Broken Glasses Amy tiptoes across the patio and past a dozing Headmaster Tom. She gently pilfers the door keys from his hand. After she enters she removes her shoes to…
The New Disciplinarian Sophie sits and waits for Headmaster Tom. When he arrives he tells her he has a surprise! She is not excited when she finds out that the…
Monthly Punishment Day Maja is just stirring in bed when the Headmaster arrives unannounced. She cannot imagine why he is there until he shows her an appointment book while swishing…
Linda Is Playing Ill Standing at attention, with her hands on her head and her pants removed, Linda has a thermometer in her mouth. Headmaster Tom takes it out and…
Punishment Memories Linda is sitting in a corner feeling sorry for herself and sniffling back tears. Jenny joins her on the floor and wraps Linda in her arms to comfort…
Mobile Services Sally has kept the Headmaster waiting. As he paces outside, she sits staring and giggling while texting on her mobile phone. After awhile Headmaster Tom has had enough…
A Caning For Elin It’s not even 1 week ago that Elin had been told to take better care of her grades. More precisely, it was clearly announced that each…
A Broken Paddle Kathrin is awaiting her much needed punishment. When Headmaster Tom comes into the room, she is bent over with her head well down – trousered bottom well…
Caught & Punished Claire and Emma are searching through the Headmaster’s bed chambers. Claire finds some money and quickly stuffs it in her sock before Headmaster Tom comes in and…
Young Chicks Chocolate Dicks Young chicks don’t care about the motion of the ocean, they only care that the boat is an ocean liner with all the trimmings. That’s right…
The Neighbor’s Barbecue It’s the first time that the neighbors are inviting Headmaster Tom and a chosen resident from Girls Boarding School for a barbecue. It’s a major honor for…
Stolen & Lost After Maja arrives home, she frantically searches her handbag. When she doesn’t find what she’s looking for she holds her head in her hands in frustration. When…
Cuties With Booties We got nuttin’ but azz for you. Some of the cutest booties around gettin’ fucked up and down. Damn, you’ve never seen a movie with so many…
Stealing Will Not Be Tolerated Alex is shocked to find out Kissie has stolen underwear from one of his shops. Kissie is a friend of the family which makes it…
New Resident Eve Eve, a blonde newcomer, listens attentively to Headmaster Tom’s lecture for new girls. He will administer her first OTK spanking, ever. She reluctantly crawls across his lap…
Bed Time Trouble As you all know, Headmaster Tom is an advocate of quick and precise decisions. Put another way for Vanessa: being 3 hours late for bed time, means…
A Reverse Gangbang Movie Meet the two luckiest studs in the world. They get to plow their big cocks into the steaming snatch of some of the hottest sluts on…
New Resident Maggy Maggy, a new resident, is two hours late to arrive. As she waits, the Headmaster runs down her reasons for being at GBS for a full three…
Double Tawse Punishment Linda and Jenny wait nervously for Headmaster Tom, both silent in their fear of what’s to come. And what comes is a double tawse punishment for the…
New Resident Angelina – Disgusting Behaviour Mr. Lewis roughly pushes a naked Angelina into a room. She has to make up three weeks of homework in order to get her…
A Bed Room Mess There are certain internal procedures at Girls Boarding School. Let’s see what happens when a girl repeatedly ignores the issue of keeping her bedroom tidy and…
Long Distance Keagen is lying on a sofa well into a conversation with her friend Jess – then she receives the warning that her credit is about to run out….
The New Resident Natascha At first Headmaster Tom wonders if there is something wrong with Natascha but eventually realizes that she must speak Russian and not understand him. She refuses…
New Resident Tina Student Tina has left open the GBS gate overnight which has caused the Headmaster’s dogs to escape. She is horrified but the Headmaster even more so since…
The New Resident – Part 1 Lisa and new resident Gina, enjoy a game of billiards in the basement. Headmaster Tom is taken aback by the new girls’ presence. He…
Nightmares Mr. Lewis has found Alexia in his private detention room without permission. She claims nightmares but Mr. Lewis doesn’t buy it and either way she should not be in…
Sting Of The Carpetbeater Linda waits patiently in front of a huge heater. When the Headmaster enters he immediately makes her turn around and begins to spank her with the…
Young Black And Sexy These are some of the hottest, nastiest, sexiest girls you have ever seen. They can’t wait to take that big dick where ever it fits. ….
Hot Asses Pounded Hard The nastiest anal queens on the planet are right here. These girls want their asses pummeled so deep that your cock comes out their mouths. That’s…
Special Audience For Annie David Myers, the facilities manager, has reported Annie to the Headmaster. She was supposed to clean the outside area but neglected to do so and her…
Special Positions Janie is called into the living room by a very unhappy Headmaster Tom. He places her over his knee with his one leg covering both of hers so…
The Tutor Amber gets a mild spanking from the Headmaster tutoring her in Mr. Lewis brief absence. She has failed to do her homework and when he questions her she…
What’s A Paddle Good For, Alice? Alice decides to use a spanking paddle as a toy. The Headmaster catches her and decides to show her what it’s really for, as…
