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…
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!…
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…
Both To Be Sentenced It’s not the content, it’s the words! Simone’s objective is to write an essay about proper punishment while spelling every word correctly. When Headmaster comes back…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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,…
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…
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…
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…
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…
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…
Sunday Evening Caning Maja has been summoned out of bed by Headmaster Tom. When he is ready to administer a caning he lowers her silk pajama bottoms and makes her…
The Photo Session Amber and Susan, dressed only in their underwear, are having a bit of fun taking photos of each other. But soon they are interrupted by Mr. Lewis,…
The Wet Cane The Headmaster is waiting when Maja enters the bathroom clad only in a fluffy white towel. He asks her to remove the towel and enter the tub,…
Nude At Daylight Christine has decided to take an early morning swim without her bikini. When the Headmaster encounters her on the stairs, covered only by a towel, he reminds…
Open Her Up When Brittney Stevens, Nicole Banks, Mahogany and Money signed up for the newest iteration of the Anal Wreckage series, they knew their assholes were in for quite…
Big And Black 8 In six scenes, white girls talk about why they can’t live without big fat black cock. Afterwards, they take a massive dick in each hole, the…
