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…
A Boring Book Since failing miserably twice before, it’s Vanessa’s third and last chance to pass her annual exam. And THIS time Headmaster Tom is in no mood for joking,…
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….
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!…
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…
A Quick Reminder Cheaters never prosper, and so long as there are those who do not wish to achieve and instead labor off of other individuals toils, so long as…
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…
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…
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…
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…
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…
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…
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…
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…
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 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…
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 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…
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…
Messed Up Rooms Maja and Marie sit tightly together on a bench in the Headmaster’s office. They have both forgotten to clean up their rooms and have appeared for punishment….
No Explanation Required Annie was on the second floor cleaning, unaware Headmaster Tom was below on the patio, talking on his cell. As she went to dump dirty water, the…
No More Warnings After being warned about coming home late two times before, Mary still has not learned her lesson. But she has learned there will be no more warnings….
The Lost Key Pig-tailed redhead Amy trudges up the stairs to the gathering room but, once there, realizes she has forgotten her key. Again. When she rings the bell Headmaster…
My Pantyhose The tables are turned once again as one student administers punishment to another. Abby is caught wearing another student’s “borrowed” fishnet pantyhose. So in order to cut to…
Learning or Swimming The Headmaster leaves Samantha to do her homework and then go to bed. She has barely done anything in the last two hours. After he leaves she…
The Training Of O – Jodi Taylor And The Slave Trainer Training of O delivers the hottest, newest starlets into servitude with hard physical slave training – like you will…
Enjoy The Lollicock NO LIMIT fucking. Plain and simple. This is HER LIMIT. In this edition we meet 4 new starlets up to the challenge. But are they ready? Directed…
Hogtied – Angela White’s First Time In Brutal Bondage And Tormented The legendary Angela White has decided that she wanted to be tied up and disciplined, and only wants the…
Mommy’s Little Pervert Pervy Corbin Dallas is jerking off furiously when his stepmom Julia Ann walks in on him. There he is, in her bed, smothering his face with her…
