Your Search Returned 1080 Results
Sadie: Post Date Strapping
When Sadie returns to the Academy from her exciting night on the town, the Headmaster welcomes her home with a painful leather strapping.
Updated: Wed. Jul. 16, 2025
Daija: Failure to Study
Daija is in the study room, where she is supposed to be studying. She is not. The Headmaster orders her over the desk with her skirt lifted and paddles her soundly.
Updated: Mon. Jul. 14, 2025
Yvonne: Paddled Hard (Part 2)
Yvonne goes over the Headmaster's knee for a hard painful paddling. In Part Two, young Yvonne goes over the Headmaster's knee for a hard paddling. She is left with a well marked bottomed and a much improved disposition.
Updated: Fri. Jul. 11, 2025
Yvonne: Paddled Hard (Part 1)
Yvonne goes over the Headmaster's knee for a hard painful paddling. In Part One, she is lectured and goes over his knee for a little hand OTK to warm her up for the hard paddling to come.
Updated: Wed. Jul. 09, 2025
Madison: Home Late
New girl Madison returns home late. The Headmaster is not amused. She is pulled over the Headmaster's knee for a painful hand spanking over her colorful panties.
Updated: Mon. Jul. 07, 2025
Sadie: Van Spanking, Hairbrush and Hand
The Headmaster pulls to the side of the road to deliver a five minute hair brush spanking to Sadie's bare bottom. A good time is had by all.
Updated: Fri. Jul. 04, 2025
Daija: Hairbrush Punishment
As an anxious Kelly looks on, the Headmaster punishes Daija soundly with a hairbrush.
Updated: Wed. Jul. 02, 2025
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)
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)
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)
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)
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)
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!
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
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
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
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
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
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)
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)
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)
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)
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
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)
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
© Alpine Entertainment Group Inc. 2009