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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
Mila: OTK Just Because 1 Mila: OTK Just Because 2 Mila: OTK Just Because 3 Mila: OTK Just Because 4
Mila: OTK Just Because
Mila is given a OTK spanking by the Headmaster just because he wants to. He starts with hand and moves on to hairbrush and hugs.
Updated: Fri. May. 02, 2025
Brooke: Bedroom Punishment 1 Brooke: Bedroom Punishment 2 Brooke: Bedroom Punishment 3 Brooke: Bedroom Punishment 4
Brooke: Bedroom Punishment
The Headmaster punishes Brooke in her bedroom with hand, hairbrush and a painful wooden scrub brush, first over her panties, then on-the-bare and finally completely naked.
Updated: Wed. Apr. 30, 2025
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
Daija: OTK, Hand and Ping Pong Paddle 1 Daija: OTK, Hand and Ping Pong Paddle 2 Daija: OTK, Hand and Ping Pong Paddle 3 Daija: OTK, Hand and Ping Pong Paddle 4
Daija: OTK, Hand and Ping Pong Paddle
For failing to stay on top of her chores, Daija goes over the Headmaster's keen for a painful bare bottom spanking with hand and ping pong paddle. (Watch for a cameo by the dog.)
Updated: Fri. Apr. 04, 2025
Sadie: Pleasure and Pain (Part 3) 1 Sadie: Pleasure and Pain (Part 3) 2 Sadie: Pleasure and Pain (Part 3) 3 Sadie: Pleasure and Pain (Part 3) 4
Sadie: Pleasure and Pain (Part 3)
Sadie is on the receiving end of a long session of pleasure and pain. The Headmaster deftly weaves painful ping-pong paddle strokes with inappropriate touching to leave poor Sadie bewitched bothered and bewildered.
Updated: Wed. Apr. 02, 2025
Sadie: Pleasure and Pain (Part 2) 1 Sadie: Pleasure and Pain (Part 2) 2 Sadie: Pleasure and Pain (Part 2) 3 Sadie: Pleasure and Pain (Part 2) 4
Sadie: Pleasure and Pain (Part 2)
Sadie is on the receiving end of a long session of pleasure and pain. The Headmaster deftly weaves painful ping-pong paddle strokes with inappropriate touching to leave poor Sadie bewitched bothered and bewildered.
Updated: Mon. Mar. 31, 2025
Sadie: Pleasure and Pain (Part 1) 1 Sadie: Pleasure and Pain (Part 1) 2 Sadie: Pleasure and Pain (Part 1) 3 Sadie: Pleasure and Pain (Part 1) 4
Sadie: Pleasure and Pain (Part 1)
Sadie is on the receiving end of a long session of pleasure and pain. The Headmaster deftly weaves painful ping-pong paddle strokes with inappropriate touching to leave poor Sadie bewitched bothered and bewildered.
Updated: Fri. Mar. 28, 2025
Daija: Schoolgirl Hairbrush Punishment 1 Daija: Schoolgirl Hairbrush Punishment 2 Daija: Schoolgirl Hairbrush Punishment 3 Daija: Schoolgirl Hairbrush Punishment 4
Daija: Schoolgirl Hairbrush Punishment
Daija, in her schoolgirl uniform, is laid over the arm of the couch, her bottom exposed, and soundly punished by the Headmaster with a hairbrush.
Updated: Wed. Mar. 26, 2025
Mila: After School Special (Part 2) 1 Mila: After School Special (Part 2) 2 Mila: After School Special (Part 2) 3 Mila: After School Special (Part 2) 4
Mila: After School Special (Part 2)
Mila is made to hold her ears as she is punished to help remind her to LISTEN while at school. In Part 2, Mila is ordered to strip naked and get down on-all-fours for a taste of the heavy strap.
Updated: Mon. Mar. 24, 2025
Mila: After School Special (Part 1) 1 Mila: After School Special (Part 1) 2 Mila: After School Special (Part 1) 3 Mila: After School Special (Part 1) 4
Mila: After School Special (Part 1)
Mila is made to hold her ears as she is punished to help remind her to LISTEN while at school. In Part 1, she is punished with the Headmaster's Mighty Rule.
Updated: Fri. Mar. 21, 2025
Daija: Home Again 1 Daija: Home Again 2 Daija: Home Again 3 Daija: Home Again 4
Daija: Home Again
Daija returns to the Academy to get a break from her troubled home life. The Headmaster welcomes her with warm open arms, but reminds her that discipline is required at the Academy. He takes her over his knee for a refreshing wake up spanking on her bare bottom.
Updated: Mon. Mar. 17, 2025
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