Misbehaving Again 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…
A Boring Book Since failing miserably twice before, it’s Vanessa’s third and last chance to pass her annual exam. And THIS time Headmaster Tom is in no mood for joking,…
Bye Bye Michael 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…
Shoeshine Girl 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…
New Resident Micaela Michael is trying to calm somebody down on the phone. He promises that Micaela will be dealt with immediately. He replaces the receiver and calls Micaela to…
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 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…
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…
The Cellar Room Elin finds herself fully naked in a place that is used only rarely for a punishment in this institution: the cold dirty cellar room! She clearly knows…
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 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…
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…
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…
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…
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…
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,…
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…
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…
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…
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…
The Photo Session Amber and Susan, dressed only in their underwear, are having a bit of fun taking photos of each other. But soon they are interrupted by Mr. Lewis,…
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:…
Deep Anal For A Blonde Bree is a beautiful, young, tall, slender, blonde European with full, natural breasts and alabaster skin. Her older muscular lover kisses his way down to…
Jacky William, a clown whose career is taking off with difficulty sees his future darken. Because in a video filmed without his knowledge where he reveals his premature ejaculation problems,…
Ultimate Reel People 1, The Taking a cue from the current reality driven entertainment-cinema superstar Ginger Lynn ushers in her own flavor of unscripted and approachable adult entertainment in “The…
Hogtied – Paige Owens: Hot, Young, And Willing To Suffer In Bondage Paige Owens begins in a predicament position with all of her weight balancing in her knees. Her feet…
Masseur’s Big Cock Makes Hot Teen Orgasm Isabeli is a lovely, small tittied, brown haired, teen babe. She’s lying on the massage table, waiting for the hung masseur to caress…
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…
Whipped Ass – Lesbian Latex Blasphemy: Ashley Paige Whips the Sin Out Of Bella Rossi Sister Ashley Paige is a sexy latex nun who finds the beautiful Bella Rossi desperately…
Hogtied – Delusional Desires In this fantasy update, Dahlia is a very skilled and professional sex therapist. Her services are needed, but Mr. Mogul finds himself growing bored with her…
