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….
Blue Monday – Blue Bottom 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….
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 Broken Cell Phone 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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
These girls know how to keep the crowd thoroughly entertained. Most cheerleaders have team spirit but some live and breathe…and fuck for their team. That’s exactly how it goes for…
Nightmares Mr. Lewis has found Alexia in his private detention room without permission. She claims nightmares but Mr. Lewis doesn’t buy it and either way she should not be in…
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…
Little teen nymphs who live to fuck and suck! These hot young fuck-sluts are wet and ready to go. They love cock more than anything, their creamy young thighs are…
Big cocks spew in tight barley legal teens! 2015 AVN Award Nominee for Best Specialty Release ? Other Genre Katerina Kay was intrigued when her mom’s boyfriend pinched a tent,…
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…
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…
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…
Where Have You Been? Headmaster Tom summons Marie. When he asks her where she has been tonight she repeatedly answers that she has been at home. At this he stands…
