Headmaster Tom

Blue Monday - Blue Bottom
Blue Monday - Blue Bottom
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Headmaster Tom hurries towards and into a large warehouse. He calls up a long flight of stairs for Jenny who comes down minus her knickers. She has been spotted with two boys during school hours.
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New Resident Annie
New Resident Annie
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Annie is a new transfer resident to Girls Boarding School. Annie is not used to the kind of rules here, so when she appears late for class one day ... she must have a meeting with the infamous Headma... more

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Headmaster Tom Annie
The Ring
The Ring
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Maria and Jodie are fighting in their room. Maria has accused Jodie of stealing and wearing her ring. The din rises to such a level that it eventually brings Headmaster Tom to their room. Although Jod... more

OTK Instructional
OTK Instructional
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Some educational movies have been stolen from the GBS library. This means Headmaster Tom must recreate them with the help of an assistant. Today it is Sarah and the instruction is for OTK. Follow alon... more

Starrings:
Headmaster Tom Sarah
Fired Little Balls
Fired Little Balls
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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 he wonders what is going on! Crouching behind a wall, this cau... more

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Headmaster Tom Sally
The Lost Key
The Lost Key
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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 Tom pulls her into the room and lines ... more

Starrings:
Headmaster Tom Amy
Trying To Cheat
Trying To Cheat
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Linda is sitting on the side of the bathtub, considering whether or not her plan will work. She decides to try it, to smooth lotion on her bottom beforehand to ease the punishment that looms ahead. Bu... more

Starrings:
Headmaster Tom Linda
Linda's Morning Sports
Linda's Morning Sports
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Linda has arrived at Headmaster Tom’s office to show off her morning sports. She beings with squats, then jumping jacks. The Headmaster has to leave and instructs Linda to continue with her exercises.... more

Starrings:
Headmaster Tom Linda
Jodie's First Caning
Jodie's First Caning
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Headmaster Tom summons Jodie to his office. We see a cane resting on a nearby chair. He demands Jodie tell him her real, full name and where she comes from. When she won’t, she has to partially disrob... more

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Headmaster Tom Jodie
Hidden Man
Hidden Man
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On a rainy day, Headmaster Tom returns to Girls Boarding School. After entering he hears strange, sexy sounds coming from Alexa’s room. Answering his knock in bra and panties, the girl claims she was ... more

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Headmaster Tom Alexa
No Explanation Required
No Explanation Required
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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 pail slipped and the dirty water splashed all over the ... more

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Headmaster Tom Annie
Domestic Work For Amy
Domestic Work For Amy
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Headmaster Tom comes home to a complete mess in the kitchen. He checks the schedule and finds the responsibility today is Amy’s. He calls her downstairs, hauls her roughly into the room, chastises her... more

Starrings:
Headmaster Tom Amy
Keagan's Punishment
Keagan's Punishment
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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 no longer and commenced ... more

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Keagan Headmaster Tom
Sentenced To Be Caned
Sentenced To Be Caned
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Irelynn is a new student at Girls Boarding School and is in need of some serious discipline. She forgot to knock before entering Headmaster Tom's office, and she must learn her lesson. He instructs ... more

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Irelynn Headmaster Tom
Beach Day Gone Wrong
Beach Day Gone Wrong
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Don't be deceived, Sanna! Your startling discovery that Headmaster Tom is not in the house does not necessarily mean that he is not around! Well, guess Sanna should have read this warning BEFORE she d... more

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Headmaster Tom Sanna
The Neighbor's Barbecue
The Neighbor's Barbecue
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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 Headmaster Tom and his first chance of finall... more

Starrings:
Elin Headmaster Tom
Bye Bye Michael
Bye Bye Michael
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Get close to the action when Headmaster Michael gets dismissed from Girls Boarding School!

What a disappointment for the one and only Headmaster Tom when he arrived at his institution for ... more

Katie's Bathroom Punishment
Katie's Bathroom Punishment
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Katie is smoking in the bathroom which the stupid girl knows is forbidden at GBS. When we next see Katie she is bending over her bathroom sink getting struck by the paddle on her bottom. Headmaster To... more

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Headmaster Tom Katie
Bed Time Trouble Day 3
Bed Time Trouble Day 3
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Third day - 3rd punishment, and obviously the worst one! Vanessa is shivering with fear when Headmaster Tom enters her bedroom with the big heavy scrubbing brush in his hand, turning her naked buttock... more

Starrings:
Headmaster Tom Vanessa
Hands & Feet
Hands & Feet
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Keagen left wet all over the floor from walking out of the shower and is accused for leaving the apartment a mess. Headmaster Tom complains to her about having to pay the maid extra because of the exc... more

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Keagen Headmaster Tom
Thank You, Sir!
Thank You, Sir!
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Jenny sits nervously on the side of the bathtub waiting for Headmaster Tom’s arrival. When he does arrive he doles out a paddling punishment on Jenny’s white, regulation panty-clad bottom. Halfway thr... more

Wall Standing For Laura & Clair
Wall Standing For Laura & Clair
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Laura and Claire, dressed in jeans and t-shirts, are waiting for punishment with bowed heads. There are two thin canes perched behind them. Eventually Headmaster Tom arrives to administer to them. Rep... more

$30,000 Lost
$30,000 Lost
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Lexa has been rude to Headmaster Tom’s business associate Mr. Stern. Her behavior has cost him a business deal and $30,000 a week. This angers the headmaster very much and Lexa’s punishment must be se... more

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Headmaster Tom Lexa
Proper Clothing
Proper Clothing
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Headmaster Tom has asked Maria many, many times to wear the proper clothing at Girls Boarding School. Now he has run out of patience. She is made to lean against the wall with her jeans pulled down as... more

Starrings:
Headmaster Tom Maria
Sophie's Birching
Sophie's Birching
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Headmaster Tom has caught Sophie coming in late. Forty minutes late! She will be punished with the birch for this transgression. Headmaster bends her over and applies the birch to her bum, Sophie’s br... more

Starrings:
Headmaster Tom Sophie
Lisa's TV Evening
Lisa's TV Evening
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It’s time to revisit Girls Boarding School! Lisa is much like many of the girls here – beautiful, but naughty and of course disobedient! Lisa is hoping for a quiet and relaxing evening, but she’s cau... more

Starrings:
Headmaster Tom Lisa
Pantyhose Caning A
Pantyhose Caning A
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In Pantyhose Caning A, Linda and Sophie, both dressed in black cocktail dresses, wait nervously for the arrival of Headmaster Tom. It is time for bed for first there is a matter of a caning. Both girl... more

Laura In The Attic
Laura In The Attic
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We see Laura crouched on the floor of the attic, naked except for her white knee highs. She will receive her punishment there, hands prone against a cold, brick wall. After Headmaster Tom strokes her ... more

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Headmaster Tom Laura
Introducing Jenny
Introducing Jenny
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The Headmaster commands Jenny to get over his knee. She knows what it is for. Her young, smooth, round bottom is in for some rosiness. Headmaster Tom flips up her short school girl’s skirt and proceed... more

3 Implements
3 Implements
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Linda, the Headmaster’s assistant, is working at her desk. Headmaster Tom enters and asks if she’s seen the letter in his hand, then, without waiting for an answer, he smacks her across the head with ... more

Starrings:
Headmaster Tom Linda
Wrong Dress Code
Wrong Dress Code
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It seems like Elin is in a little trouble for not adhering to the proper dress code at her boarding girl. First, headmaster Tom orders Elin to show her bra. Then, she's ordered to show her knickers,... more

Starrings:
Elin Headmaster Tom
My First Day
My First Day
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Christine is sitting demurely on a straight-backed chair, explaining how she came to be at an institution like Girls Boarding School. She had a wake-up call one day, when she realized that she was dri... more

First TIme Meeting With HM Tom
First TIme Meeting With HM Tom
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It's been more than 1 year since Simone arrived at the Girls Boarding School for a good education and to learn the importance of obedience and respect. Simone wouldn't claim that she ENJOYS her stay b... more

Starrings:
Headmaster Tom Simone
Shoeshine Girl
Shoeshine Girl
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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 face at the sight set out before her. As her hands... more

Starrings:
Headmaster Tom Nicole
Broken Glasses
Broken Glasses
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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 make her way quietly through the house and to t... more

Starrings:
Headmaster Tom Amy
Emma's Big Plans
Emma's Big Plans
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Emma has written down a plan to escape from Girls Boarding School and hides it in a book. She wants to go to a far off land where there is no discipline, no punishment. But, unfortunately for her, Hea... more

Starrings:
Headmaster Tom Emma
Clean The Dishes!
Clean The Dishes!
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Headmaster Tom has returned to his apartment and a mess in his kitchen. He had asked Claire to clean but what she did instead was put the dirty things in his dresser drawer. She must know that this wo... more

Caught & Punished
Caught & Punished
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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 finds them. When his queries as to wha... more

Locked - Justine
Locked - Justine
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Mr. Lewis is in the storeroom looking for a snack. Suddenly, redheaded Justine approaches and quickly closes the door and locks him inside. She runs away grinning while Mr. Lewis bangs on the door and... more

New Resident Abi - Initial Interview
New Resident Abi - Initial Interview
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Abi, dressed very nicely in a halter dress with a short skirt, has requested a private interview with Headmaster Tom. Her life so far has been a series of bad mistakes. Under his questioning she revea... more

Starrings:
Headmaster Tom Abi
A Waste Of Time
A Waste Of Time
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Maggy is playing a prank. Isn't funny turning off the television again and again, hiding behind the curtains with a replacement remote control, while Headmaster Tom is trying to enjoy his well-earned ... more

Starrings:
Headmaster Tom Maggy
A Beautiful Sunday Morning
A Beautiful Sunday Morning
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Jenny sits in the dining room painting her fingernails a lovely shade of red. Knowing she is breaking the rules, she hides her fingers when the Headmaster arrives. But, unfortunately, she cannot hide ... more

Painful Tutoring
Painful Tutoring
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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 same matter, Headmaster Tom showed himself ... more

Starrings:
Headmaster Tom Simone
Dress Code Attitude
Dress Code Attitude
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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 skirt and a LEATHER JACKET?? Whereas it ... more

Starrings:
Headmaster Tom Sanna
The Broken Cell Phone
The Broken Cell Phone
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Another case of disobedience and stupidity at GBS. Against all warnings Maggy couldn't resist fiddling around with Headmaster Tom's shiny new toy, a brand-new cell phone with all the bells and whistle... more

Starrings:
Headmaster Tom Maggy
Misbehaving Again
Misbehaving Again
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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 the covers fully clothed... more

Starrings:
Elin Headmaster Tom
Kelly's Failure
Kelly's Failure
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Kelly, sitting on the floor behind the couch, waits anxiously for the Headmaster to arrive. And when he does he is furious. Kelly has failed her exams for the third time and that means punishment! more

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Headmaster Tom Kelly
Spanking The Laziness Out Of Her
Spanking The Laziness Out Of Her
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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 home can be fun! Alone?? Really??? Watch the video...Hea... more

Hide & Seek
Hide & Seek
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While the Headmaster calls her name around campus, Linda is enjoying herself. She's ensconced on a balcony smoking and sipping wine. She is too naughty to be believed. When Headmaster Tom finally loca... more

Starrings:
Headmaster Tom Linda
Linda Is Playing Ill
Linda Is Playing Ill
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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 with disgust pronounces her ok. But now she must stay to ... more

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Headmaster Tom Linda
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