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…
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…
Playing A Prank Headmaster Tom is mad as hell! He missed an extremely important phone call when he couldn’t enter GBS because one of the girl changed the door code!…
Maggy Whipped By Headmaster Tom Headmaster Tom is making a very embarrassing phone call. A package has arrived at GBS addressed to Maggy. On being opened it was found to…
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…
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…
First Contact This movie shows Nicole’s first encounter with Headmaster Tom. Since she has been warned by the other girls, and since she heard all the rumors about him, she…
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…
2 Hot 2 Handle From The Liner Notes: From day to night your senses are working overtime. Pulse racing, your libido simmering to its boiling point. Just when your body…
Painful Tutoring It’s Simone’s second chance to give a talk about ‘Sweden’ as a part of her intermediate exam in geography. The week before, when she failed miserably in the…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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….
Stolen Money Mr. Lewis is very unhappy with Lisa. He has given her three occasions to clean the house and she has failed every time. He guides her around the…
Hot Teen Sluts Stuffed Full! Anal & DP These slutty little nymphos love to get their tiny holes stuffed with cock. From deep throating massive meat to wicked anal poundings…
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…
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…
Big titty mommies stacked to the rafters! Momma’s got a built-in playground. A sexual circus carnival with all the rides you need right under her massive big-top. Every ticket’s a…
Sisterhood All Girl Orgies It’s all about sisterhood, or is that sister’s hoods? Not a neighborhood, and not a society that fosters caring and unity, but the hood that hides…
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…
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…
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…
Big cocks spew in tight barley legal teens! 2015 AVN Award Nominee for Best Specialty Release ? Other Genre Katerina Kay was intrigued when her mom’s boyfriend pinched a tent,…
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…
