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…
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…
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…
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…
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…
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…
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…
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…
Little Fuck Slave Mickey Mod and Jane Wilde were partners in crime and now that he’s the boss, he keeps Jane prisoner in his house to use only for sex….
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…
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…
Everything Butt – Beautiful Asian Biker Babe Prospect gets an Anal Hazing from Bikers Sheena Rider is a bad ass biker bitch looking to impress the Biker Bar Boss Lady,…
Butthole Prison: Dee Williams Locks Up Charlotte Sartre for Anal Fraud Charlotte Sartre is a very disobedient inmate at the all women’s prison. She’s been keistering anal toys and copulating…
Prove Your Worth Madame Kelli Provocateur and Betty Solace make meaty muscle boy Davin Strong prove his worth with a delicious Double Domme dungeon session that gets his cock rock…
Whipped Ass – Fuck Love Party: Leigh Raven And Delirious Hunter Clear The Room Its the Fuck Love Party of the year and everyone is having fun except for poor…
Brutal Sessions – Skylar Snow’s Abject Anal Invasion Sweet Skyler Snow gets all of her holes slammed by Seth Gamble, as she’s used and abused in bondage. We open with…
