Private Pleasures Every woman has secret sexual fantasies, Private passionate thoughts. So few live out their dreams. Join Playgirl on an exotic adventure exploring sensual desires. A journey where a…
New Resident Emily – No Discussion Required Emily, new to GBS, secrets herself in a bathroom and confidently lights up a cigarette. Later, we see her nervously gnawing her nails…
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…
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…
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…
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…
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…
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…
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…
Monthly Punishment Day Maja is just stirring in bed when the Headmaster arrives unannounced. She cannot imagine why he is there until he shows her an appointment book while swishing…
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…
Spanking The Laziness Out Of Her 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…
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…
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…
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…
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…
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…
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…
Cuties With Booties We got nuttin’ but azz for you. Some of the cutest booties around gettin’ fucked up and down. Damn, you’ve never seen a movie with so many…
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…
Sisterhood All Girl Orgies It’s all about sisterhood, or is that sister’s hoods? Not a neighborhood, and not a society that fosters caring and unity, but the hood that hides…
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…
New Resident Angelina – Disgusting Behaviour Mr. Lewis roughly pushes a naked Angelina into a room. She has to make up three weeks of homework in order to get her…
Hot Teen Sluts Stuffed Full! Anal & DP These slutty little nymphos love to get their tiny holes stuffed with cock. From deep throating massive meat to wicked anal poundings…
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…
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…
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…
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…
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…
It’s A Group Thing When three’s a crowd, take off all the clothes and see what happens! Threesomes between MMF and FFM here, with all ebony ‘actors’ sucking and fucking…
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…
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…
