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…
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….
New Resident Lucy Lucy, inconsiderate girl that she is, enters the living room without knocking. When she returns after knocking she delivers a speeding ticket notice to the Headmaster. He…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
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…
Have sex like the best selling novels! Explore the eroticism in being bound and vulnerable. Enhance passion during the art of spanking. Stimulation ultimately enhanced with the intimacy of food….
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…
Femdom Factory! Introduction Of World Class Dominatrix Fetish Liza! Divine Bitches eastern European expeditions continue on to Germany! We’re happy to announce the collaboration & debut of world famous femdom…
Whipped Ass – Featuring Felony and Ashli Orion Ashli Orion is hot for Felony and excited to submit to her deepest, darkest bondage fantasies with this stunningly beautiful taskmaster! Felony…
Caged Feet! In this foot fetishists fantasy come true film we pay homage to one of my favorite genres of early pornographic films, Women In Prison exploitation films! Dangerous steamy…
Hogtied – Submissive Goth Girl is Bound, Tormented, and Made to Cum This is Charlotte’s first time on Hogtied and she definitely doesn’t disappoint. She is very timid upon first…
Rough and Sweet Winter Ryleigh A rough and sweet reunion with Winter Ryleigh. Kissing, spanking, blowjob, facefucking, doggy, riding, and missionary until I pull out and cum in her mouth….
Gal Ritchie: Predicament Bondage, Torment, and Suffering Makes for a Happy Gal Gal Ritchie is brand spanking new and has set so many things in motion to be right in…
Jemma Jansen in Fucking the Babysitter Hi there, Jemma here. Erica Cherry, the babysitter, is here wearing her favorite pink top, jean shorts & long ponytails. Basically feeling bored, she…
Cherry Mavrik 6 You catch hottie Cherry Mavrik hopping into the shower after a long, hot day. But you’d rather give her a bath with your tongue! Your eagerness makes…
Mature Spanish Woman and a Filipino Teenager are Having Sex, A A Mature Spanish Woman and a Filipino Teenager are Having Sex. Carla Pons’ experiment. She’ll try to make all…
