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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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 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…
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….
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…
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 – 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…
Sting Of The Carpetbeater Linda waits patiently in front of a huge heater. When the Headmaster enters he immediately makes her turn around and begins to spank her with the…
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…
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…
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…
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…
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…
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….
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…
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…
Semi Public Punishment This is a movie about the importance of proper clothing. Sophia waits for the Headmaster perched on a windowsill. They agree that Sophie has a problem with…
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….
Pantyhose Caning A In Pantyhose Caning A, Linda and Sophie, both dressed in black beverage dresses, wait nervously for the arrival of Headmaster Tom. It is time for bed for…
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…
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,…
Missed Article While reading, Mr. Lewis notices an article he wished to peruse has been torn out of the magazine. He believes the culprit is Grace and goes tearing up…
Gia Darling: Big Boob Adventures #3 Gia Darling is back to show off some of her favorite big boob transgender girlfriends! . Gia Darling and Redhead Threesome Bondage – Duration:…
X Professionals There may not be Honor Among Thieves, but there is OUTRAGEOUS SEX! Welcome to the World of Fast Cars, Fast Cash, and Faster Women! Warning: Dangerous Curves Ahead!…
Hogtied – Alt Dream Girl Krysta Kaos Abused And Fucked In Extreme Rope Bondage! Krysta Kaos returns so she can be punished and humiliated in The Pope’s sadistic dungeon. Her…
Hairy Pussy Vol. 8 As the old saying goes, where there is hair there is joy, and today on Private, we prove it with our 8th installment of Hairy Pussy…
