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Daija: Going Out While Grounded 1 Daija: Going Out While Grounded 2 Daija: Going Out While Grounded 3 Daija: Going Out While Grounded 4
Daija: Going Out While Grounded
The Headmaster learns that Daija has been sneaking out while she has been grounded and confined to the house. He takes her OTK and uses a hairbrush on her shapely bottom. Her squirming and crying suggests that he made his point.
Updated: Mon. Apr. 28, 2025
Mila: Cooking a Little Breakfast 1 Mila: Cooking a Little Breakfast 2 Mila: Cooking a Little Breakfast 3 Mila: Cooking a Little Breakfast 4
Mila: Cooking a Little Breakfast
Poor lovely simple minded Mila struggles to prepare even a simple breakfast for Headmaster Ken. He orders her naked as he punishes her with a yardstick across her shapely bottom.
Updated: Fri. Apr. 25, 2025
Daija: Paddled Hard 1 Daija: Paddled Hard 2 Daija: Paddled Hard 3 Daija: Paddled Hard 4
Daija: Paddled Hard
The Headmaster discovers Daija has been sending nude photos to her boyfriend. Her orders her to strip nude and bend over and grab her ankles for a hard painful paddling.
Updated: Wed. Apr. 23, 2025
Madison: Messy Kitchen 1 Madison: Messy Kitchen 2 Madison: Messy Kitchen 3 Madison: Messy Kitchen 4
Madison: Messy Kitchen
Waify yet incompetent Madison finds it impossible to keep the kitchen clean. The Headmaster helps motivate her with face slaps and an OTK hand spanking.
Updated: Mon. Apr. 21, 2025
Tabitha: Naked OTK 1 Tabitha: Naked OTK 2 Tabitha: Naked OTK 3 Tabitha: Naked OTK 4
Tabitha: Naked OTK
Naked, lovely and tattooed Tabitha goes over the Headmaster's loving knee for a lengthy OTK hand-spanking. Afterward she is posed and photographed.
Updated: Fri. Apr. 18, 2025
Daija: OTK - Hairbrush and Paddle 1 Daija: OTK - Hairbrush and Paddle 2 Daija: OTK - Hairbrush and Paddle 3 Daija: OTK - Hairbrush and Paddle 4
Daija: OTK - Hairbrush and Paddle
The Headmaster gently counsels Daija on the importance of keeping her personal space neat and tidy. She goes over his knee for a painful dose of the hairbrush and paddle.
Updated: Wed. Apr. 16, 2025
Zara: Submissive Training 1 Zara: Submissive Training 2 Zara: Submissive Training 3 Zara: Submissive Training 4
Zara: Submissive Training
Zara continues along her path to submissiveness, helped, as always, by the Headmaster's gentle guidance. Already stripped naked, and with a very bruised and sore bottom, she goes over the Headmaster's knee for a long slow hand spanking.
Updated: Mon. Apr. 14, 2025
Jenna: Return to the Punishment Room 1 Jenna: Return to the Punishment Room 2 Jenna: Return to the Punishment Room 3 Jenna: Return to the Punishment Room 4
Jenna: Return to the Punishment Room
Naked Jenna is bound with her hands above her head and punished by the Headmaster with crop and strap.
Updated: Fri. Apr. 11, 2025
Sophie & Madison: Learning the Ropes (Part 2) 1 Sophie & Madison: Learning the Ropes (Part 2) 2 Sophie & Madison: Learning the Ropes (Part 2) 3 Sophie & Madison: Learning the Ropes (Part 2) 4
Sophie & Madison: Learning the Ropes (Part 2)
New girl Sophie continues her orientation into life in the Academy. She is weighed, measured and interviewed further. Then Sophie and her 'special friend' Madison are both spanked by the Headmaster.
Updated: Wed. Apr. 09, 2025
Sophie & Madison: Learning the Ropes (Part 1) 1 Sophie & Madison: Learning the Ropes (Part 1) 2 Sophie & Madison: Learning the Ropes (Part 1) 3 Sophie & Madison: Learning the Ropes (Part 1) 4
Sophie & Madison: Learning the Ropes (Part 1)
New girl Sophie (aka 'GI Jane') continues her initiation into the Academy with her 'close personal' friend Madison looking on. Watch as Headmaster Ken skillfully bends this modern day warrior princess to his mighty will. In Part One, the defiant Valkyrie is made to lay out on the bed for a viscous and deliberate hand spanking.
Updated: Mon. Apr. 07, 2025
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