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Sophie & Madison: Adventures in Babysitting (Part 1) 1 Sophie & Madison: Adventures in Babysitting (Part 1) 2 Sophie & Madison: Adventures in Babysitting (Part 1) 3 Sophie & Madison: Adventures in Babysitting (Part 1) 4
Sophie & Madison: Adventures in Babysitting (Part 1)
Sophie and Madison's babysitting adventure continues. When Sophie is unable to tame a wild and undisciplined Madison, the Headmaster is forced to step in to deliver some old school discipline to both unruly girls.
Updated: Fri. Nov. 14, 2025
Brooke: Playing Dress Up 1 Brooke: Playing Dress Up 2 Brooke: Playing Dress Up 3 Brooke: Playing Dress Up 4
Brooke: Playing Dress Up
Brooke's Day of punishment continues. After an OTK hand spanking, she is ordered to get completely naked, then change into a lovely summer dress, before going back over the Headmaster's knee for an additional dose of OTK punishment.
Updated: Wed. Nov. 12, 2025
Daija & Amber: Paddle & Spank 1 Daija & Amber: Paddle & Spank 2 Daija & Amber: Paddle & Spank 3 Daija & Amber: Paddle & Spank 4
Daija & Amber: Paddle & Spank
The Headmaster works tirelessly to help improve Daija's attitude. As Daija holds several uncomfortable and exposed positions, the Headmaster applies a healthy dose of the paddle to her already red and tender bottom. Amber is then called into the room, ordered to bend over and grab her ankles and spanked lovingly.
Updated: Mon. Nov. 10, 2025
Zara: Naked Strapping 1 Zara: Naked Strapping 2 Zara: Naked Strapping 3 Zara: Naked Strapping 4
Zara: Naked Strapping
The Headmaster continues to celebrate wayward Zara's return to the Academy by bending her naked over the foot of the bed and further punishing her already well bruised bottom with a heavy leather strap.
Updated: Wed. Nov. 05, 2025
Brooke and Daija: Paddled Together in the Bedroom 1 Brooke and Daija: Paddled Together in the Bedroom 2 Brooke and Daija: Paddled Together in the Bedroom 3 Brooke and Daija: Paddled Together in the Bedroom 4
Brooke and Daija: Paddled Together in the Bedroom
When the Headmaster catches Brooke in a lie he wastes no time bending her over the bed and paddling her bare bottom. Smart mouthed Daija finds herself in the same position moments later.
Updated: Mon. Nov. 03, 2025
Amber & Daija: Punished School Girls (Part 2) 1 Amber & Daija: Punished School Girls (Part 2) 2 Amber & Daija: Punished School Girls (Part 2) 3 Amber & Daija: Punished School Girls (Part 2) 4
Amber & Daija: Punished School Girls (Part 2)
Amber and Daija, already tender and sobbing from their earlier paddling, are further punished by the Headmaster with hand and hairbrush.
Updated: Wed. Oct. 29, 2025
Jenna: Hard Strapping 1 Jenna: Hard Strapping 2 Jenna: Hard Strapping 3 Jenna: Hard Strapping 4
Jenna: Hard Strapping
As Jenna's grades continue to suffer due to her out of control drinking, the Headmaster heroically attempts to modify the troubled young girl's behavior through careful and selective negative reinforcement. She is sent to her room to strip and assume the appropriate position on-all-fours on the bed to receive a long hard strapping.
Updated: Mon. Oct. 27, 2025
Amber & Daija: Punished School Girls (Part 1) 1 Amber & Daija: Punished School Girls (Part 1) 2 Amber & Daija: Punished School Girls (Part 1) 3 Amber & Daija: Punished School Girls (Part 1) 4
Amber & Daija: Punished School Girls (Part 1)
Amber and Daija, in their school girl uniforms, are punished together by the Headmaster with hand and heavy wooden paddle.
Updated: Fri. Oct. 24, 2025
Amanda: Hand, Paddle and Hairbrush 1 Amanda: Hand, Paddle and Hairbrush 2 Amanda: Hand, Paddle and Hairbrush 3 Amanda: Hand, Paddle and Hairbrush 4
Amanda: Hand, Paddle and Hairbrush
Naked and her hair still wet from the tub, the Headmaster continues with Amanda's punishment. He begins with a hand spanking as she kneels on the floor, her head between his feet. The Headmaster then moves Amanda up on to a bench, puts her on all fours, and paddles her until she is screaming and sobbing. He finishes with an OTK and on-all-fours hairbrush spanking.
Updated: Wed. Oct. 22, 2025
Jenna: Naked OTK Hand Spanking 1 Jenna: Naked OTK Hand Spanking 2 Jenna: Naked OTK Hand Spanking 3 Jenna: Naked OTK Hand Spanking 4
Jenna: Naked OTK Hand Spanking
For continuing to run off without permission, the Headmaster gives Jenna a long naked OTK hand spanking.
Updated: Mon. Oct. 20, 2025
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