Red, Red And Red Irelynn could hardly believe her eyes when she read the punishment note a few days ago: a bruised bottom for 2 weeks! In other words: bottom…
Funny Signs Headmaster Tom is getting some ice from the fridge when he notices that the fridge door is sticky and dirty. He calls for Maggy and hands her a…
New Resident Vanja Michael, a headmaster at GBS finds Vanja, a new resident, kneeling on a wooden stool, her long blonde hair tied in two plaits and her hands on…
New Resident Linn Linn is sitting at the table using her laptop. Michael, a master at GBS, comes into the room. He wastes no time in telling her why he…
Shoeshine Girl Headmaster Tom is obviously livid with Nicole. He calls her into the living room to see what he has prepared for her. Her horror plainly shows on her…
Bye Bye Michael Get close to the action when Headmaster Michael gets dismissed from Girls Boarding School! What a disappointment for the one and only Headmaster Tom when he arrived…
Misbehaving Again Elin is bringing herself into trouble again! Did she REALLY believe that Headmaster Tom wouldn’t find out about her late return, hours after the committed time? Slipping under…
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….
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…
Dress Code Attitude When new resident Sanna came back home to the institution in the evening, Headmaster Tom could hardly believe his eyes! She was wearing black leggings, a fancy…
The Broken Cell Phone Another case of disobedience and stupidity at GBS. Against all warnings Maggy couldn’t resist fiddling around with Headmaster Tom’s shiny new toy, a brand-new cell phone…
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…
Sista Slam Some chicks just need more than one dick. These guys are packing some of the biggest black boners that our desperate divas have ever seen. When this heinously…
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…
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…
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…
Caught In The Act Alone in her room, the young girl is giving herself some pleasure. Unfortunately, Headmaster Tom hears her moans of ecstasy and breaks into her reverie. He…
The Cellar Room Elin finds herself fully naked in a place that is used only rarely for a punishment in this institution: the cold dirty cellar room! She clearly knows…
Spanking The Laziness Out Of Her Roseanne is a lazy schoolgirl having a lazy afternoon. She’s just reading some nice magazines and listening to some cool music. Being alone at…
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…
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…
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…
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…
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…
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…
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 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…
These girls know how to keep the crowd thoroughly entertained. Most cheerleaders have team spirit but some live and breathe…and fuck for their team. That’s exactly how it goes for…
It’s A Group Thing When three’s a crowd, take off all the clothes and see what happens! Threesomes between MMF and FFM here, with all ebony ‘actors’ sucking and fucking…
Little teen nymphs who live to fuck and suck! These hot young fuck-sluts are wet and ready to go. They love cock more than anything, their creamy young thighs are…
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…
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…
Bangin’ There’s only one word that can describe the bodies of these beautiful woman. Bangin’; curvaceous, large voluptuous breasts, full lips, and a tight pink pussy that can juice any…
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…
Where Have You Been? Headmaster Tom summons Marie. When he asks her where she has been tonight she repeatedly answers that she has been at home. At this he stands…
Have sex like the best selling novels! Explore the eroticism in being bound and vulnerable. Enhance passion during the art of spanking. Stimulation ultimately enhanced with the intimacy of food….
Without Knickers As the Headmaster is going over her school work with Tina he discovers, to his horror, that she is not wearing any knickers. Since she thinks it’s so…
