New Resident Micaela Michael is trying to calm somebody down on the phone. He promises that Micaela will be dealt with immediately. He replaces the receiver and calls Micaela to…
Fired Little Balls Sally, mischievous imp that she is, decides it will be fun to fire little balls at Headmaster Tom! They land on his head and his work and…
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…
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…
New Resident Lucy Lucy, inconsiderate girl that she is, enters the living room without knocking. When she returns after knocking she delivers a speeding ticket notice to the Headmaster. He…
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….
It’s All Pink On The Inside 5 Remember – love is universal. It doesn’t matter what you look like on the outside, because it’s all pink inside, right? So, that…
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…
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 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…
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…
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…
New Resident Emily – No Discussion Required Emily, new to GBS, secrets herself in a bathroom and confidently lights up a cigarette. Later, we see her nervously gnawing her nails…
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…
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…
Hide & Seek While the Headmaster calls her name around campus, Linda is enjoying herself. She’s ensconced on a balcony smoking and sipping . She is too naughty to be…
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…
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…
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…
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…
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…
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….
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…
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 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…
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…
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…
