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Madison: Red Cheeks 1 Madison: Red Cheeks 2 Madison: Red Cheeks 3 Madison: Red Cheeks 4
Madison: Red Cheeks
Madison is punished for her cheeky attitude.
Updated: Mon. Jun. 30, 2025
Mila: Long Hard Punishment with Paddle and Hairbrush (Part 2) 1 Mila: Long Hard Punishment with Paddle and Hairbrush (Part 2) 2 Mila: Long Hard Punishment with Paddle and Hairbrush (Part 2) 3 Mila: Long Hard Punishment with Paddle and Hairbrush (Part 2) 4
Mila: Long Hard Punishment with Paddle and Hairbrush (Part 2)
Mila is given a long hard punishment by the Headmaster. In part two, the Headmaster switches to the hair brush to make sure sad lonely little Mila has learned her lesson.
Updated: Fri. Jun. 27, 2025
Mila: Long Hard Punishment with Paddle and Hairbrush (Part 1) 1 Mila: Long Hard Punishment with Paddle and Hairbrush (Part 1) 2 Mila: Long Hard Punishment with Paddle and Hairbrush (Part 1) 3 Mila: Long Hard Punishment with Paddle and Hairbrush (Part 1) 4
Mila: Long Hard Punishment with Paddle and Hairbrush (Part 1)
Mila is given a long hard punishment by the Headmaster. In part one, she is given a legs up inspection and a paddling followed by some bare bottom OTK.
Updated: Wed. Jun. 25, 2025
Five Girl Punishment (Part 2) 1 Five Girl Punishment (Part 2) 2 Five Girl Punishment (Part 2) 3 Five Girl Punishment (Part 2) 4
Five Girl Punishment (Part 2)
Daija, Bridget, Heather, Lynn and Amber, all completely naked, are punished together by the Headmaster in the bedroom with paddle and strap.
Updated: Mon. Jun. 23, 2025
Mila: Late for her Meeting with the Headmaster (Part 2) 1 Mila: Late for her Meeting with the Headmaster (Part 2) 2 Mila: Late for her Meeting with the Headmaster (Part 2) 3 Mila: Late for her Meeting with the Headmaster (Part 2) 4
Mila: Late for her Meeting with the Headmaster (Part 2)
Innocent young Mila is late for her scheduled meeting with the Headmaster. In Part 2, she is sent to fetch a leather strap for further punishment. She is order to strip naked and is then made to kneel on the floor for a hard strapping.
Updated: Fri. Jun. 20, 2025
Mila: Late for her Meeting with the Headmaster (Part 1) 1 Mila: Late for her Meeting with the Headmaster (Part 1) 2 Mila: Late for her Meeting with the Headmaster (Part 1) 3 Mila: Late for her Meeting with the Headmaster (Part 1) 4
Mila: Late for her Meeting with the Headmaster (Part 1)
Innocent young Mila is late for her scheduled meeting with the Headmaster. She is whisked over his knee, her dress is lifted and she is given a stinging bare bottomed hand spanking.
Updated: Wed. Jun. 18, 2025
Daija: Where's My Money! 1 Daija: Where's My Money! 2 Daija: Where's My Money! 3 Daija: Where's My Money! 4
Daija: Where's My Money!
Daija borrowed money from the Headmaster that she has failed to repay in a timely manner. The Headmaster takes Daija over his knee for a hard and painful bare bottom paddling.
Updated: Mon. Jun. 16, 2025
Zara: The Punishment Room 1 Zara: The Punishment Room 2 Zara: The Punishment Room 3 Zara: The Punishment Room 4
Zara: The Punishment Room
Zara is ordered to the punishment room where her wrists are bound over her head. She is then given doses of the strap and the yardstick. She is quickly reduces to helpless sobs.
Updated: Fri. Jun. 13, 2025
Amber: Long Naked Hand Spanking 1 Amber: Long Naked Hand Spanking 2 Amber: Long Naked Hand Spanking 3 Amber: Long Naked Hand Spanking 4
Amber: Long Naked Hand Spanking
Amber has just been released from jail and the Headmaster welcomes her home with a long hard naked hand spanking.
Updated: Wed. Jun. 11, 2025
Daija: Faces 1 Daija: Faces 2 Daija: Faces 3 Daija: Faces 4
Daija: Faces
Daija is bent over the desk and given a hard spanking with the ping pong paddle. A camera tight on her face peers into her very soul as she endures a life changing punishment.
Updated: Mon. Jun. 09, 2025
Kyndall: Bed Time Spanking 1 Kyndall: Bed Time Spanking 2 Kyndall: Bed Time Spanking 3 Kyndall: Bed Time Spanking 4
Kyndall: Bed Time Spanking
Pretty new girl Kyndall ends her first day at the Academy with a bed time spanking. The Headmaster spanks her bare bottom OTK in her bedroom.
Updated: Fri. Jun. 06, 2025
Daija: Attitude and Exposure 1 Daija: Attitude and Exposure 2 Daija: Attitude and Exposure 3 Daija: Attitude and Exposure 4
Daija: Attitude and Exposure
Daija's confusing, random and unexplainable actions earn her an afternoon with with the ping pong paddle.
Updated: Wed. Jun. 04, 2025
Mila: The Discussion (Part 2) 1 Mila: The Discussion (Part 2) 2 Mila: The Discussion (Part 2) 3 Mila: The Discussion (Part 2) 4
Mila: The Discussion (Part 2)
Mila is called in for a 'discussion', by the Headmaster. The topics covered are varied and far reaching and include a bare bottom and much enthusiastically inappropriate touching and what not.
Updated: Mon. Jun. 02, 2025
Mila: The Discussion (Part 1) 1 Mila: The Discussion (Part 1) 2 Mila: The Discussion (Part 1) 3 Mila: The Discussion (Part 1) 4
Mila: The Discussion (Part 1)
Mila is called in for a 'discussion', by the Headmaster. The topics covered are varied and far reaching and include a bare bottom and much enthusiastically inappropriate touching and what not.
Updated: Fri. May. 30, 2025
Mila: High and Tight (Part 2) 1 Mila: High and Tight (Part 2) 2 Mila: High and Tight (Part 2) 3 Mila: High and Tight (Part 2) 4
Mila: High and Tight (Part 2)
During a routine inspection, the Headmaster discovers Mila has been slacking in her personal hygiene rituals. To help keep her motivated he beats her with a hairbrush, lovingly.
Updated: Wed. May. 28, 2025
Mila: High and Tight (Part 1) 1 Mila: High and Tight (Part 1) 2 Mila: High and Tight (Part 1) 3 Mila: High and Tight (Part 1) 4
Mila: High and Tight (Part 1)
During a routine inspection, the Headmaster discovers Mila has been slacking in her personal hygiene rituals. To help keep her motivated he beats her with a hairbrush, lovingly.
Updated: Mon. May. 26, 2025
Daija: Packing 1 Daija: Packing 2 Daija: Packing 3 Daija: Packing 4
Daija: Packing
Daija and the Headmaster pack for their upcoming trip to Paris. Daija fails to follow the Headmaster's instructions. She is paddled into a quiver lump of obedience.
Updated: Fri. May. 23, 2025
Daija: Photo Shoot (Part 2) 1 Daija: Photo Shoot (Part 2) 2 Daija: Photo Shoot (Part 2) 3 Daija: Photo Shoot (Part 2) 4
Daija: Photo Shoot (Part 2)
Daija is late for her photo shoot and the Headmaster is not amused. In part two, Daija is dressed up and made to kneel on a chair for a painful paddling. She is then posed in several very exposed positions for photos.
Updated: Wed. May. 21, 2025
Daija: Photo Shoot (Part 1) 1 Daija: Photo Shoot (Part 1) 2 Daija: Photo Shoot (Part 1) 3 Daija: Photo Shoot (Part 1) 4
Daija: Photo Shoot (Part 1)
Daija is late for her photo shoot and the Headmaster is not amused. In part one, he finds wayward young Daija lounging on the veranda enjoying a relaxing smoke. He drags her into the house, orders her to strip naked and then delivers a noisy OTK hand-spanking to her sassy bare bottom.
Updated: Mon. May. 19, 2025
Yvonne: Day of Discipline (Part 3) 1 Yvonne: Day of Discipline (Part 3) 2 Yvonne: Day of Discipline (Part 3) 3 Yvonne: Day of Discipline (Part 3) 4
Yvonne: Day of Discipline (Part 3)
Nubile new girl Yvonne is still learning the way of things at the Academy. The Headmaster decides a day of punishment will help her to see the light. In Part Three, sobbing and squirming Yvonne is ordered down on the floor, her ass high and very exposed where her punishment with the Headmaster's massive yardstick continues. Her punishment finishes OTK with a wooden brush and then a hand spanking on the backs of her thighs.
Updated: Fri. May. 16, 2025
Yvonne: Day of Discipline (Part 2) 1 Yvonne: Day of Discipline (Part 2) 2 Yvonne: Day of Discipline (Part 2) 3 Yvonne: Day of Discipline (Part 2) 4
Yvonne: Day of Discipline (Part 2)
Nubile new girl Yvonne is still learning the way of things at the Academy. The Headmaster decides a day of punishment will help her to see the light. In Part 2, tiny Yvonne is inspected by the Headmaster and given a healthy does of the leather strap and the yardstick.
Updated: Wed. May. 14, 2025
Yvonne: Day of Discipline (Part 1) 1 Yvonne: Day of Discipline (Part 1) 2 Yvonne: Day of Discipline (Part 1) 3 Yvonne: Day of Discipline (Part 1) 4
Yvonne: Day of Discipline (Part 1)
Nubile new girl Yvonne is still learning the way of things at the Academy. The Headmaster decides a day of punishment will help her to see the light. In Part 1, Yvonne is introduced to the hair brush.
Updated: Mon. May. 12, 2025
Daija: Naked OTK 1 Daija: Naked OTK 2 Daija: Naked OTK 3 Daija: Naked OTK 4
Daija: Naked OTK
The Headmaster orders Daija to strip naked and go over his knee for a hard OTK hand-spanking.
Updated: Fri. May. 09, 2025
Clarice: Punished for Not Taking Care of Herself (Part 2) 1 Clarice: Punished for Not Taking Care of Herself (Part 2) 2 Clarice: Punished for Not Taking Care of Herself (Part 2) 3 Clarice: Punished for Not Taking Care of Herself (Part 2) 4
Clarice: Punished for Not Taking Care of Herself (Part 2)
Clarice's late night party till dawn lifestyle is catching up with her and affecting her health. The Headmaster offers holistic wellness counseling in the form of a long punishment session. In Part Two, the frail and sickly young lass is ordered to strip naked and bend over and grab her ankles. She then receives further counseling with hand, yardstick and strap. Based on the new found rosy glow in her cheeks, she seems well on the path to recovery.
Updated: Wed. May. 07, 2025
Clarice: Punished for Not Taking Care of Herself (Part 1) 1 Clarice: Punished for Not Taking Care of Herself (Part 1) 2 Clarice: Punished for Not Taking Care of Herself (Part 1) 3 Clarice: Punished for Not Taking Care of Herself (Part 1) 4
Clarice: Punished for Not Taking Care of Herself (Part 1)
Clarice's late night party till dawn lifestyle is catching up with her and affecting her health. The Headmaster offers holistic wellness counseling in the form of a long punishment session. In Part One, the sickly girl is given an OTK hand-spanking and some up close time with the Headmaster's mighty 'yardstick of negative reinforcement'.
Updated: Mon. May. 05, 2025
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