Sadie: Van Spanking, Hairbrush and Hand
Updated: Fri. Jul. 04, 2025
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.

Daija: Hairbrush Punishment
Updated: Wed. Jul. 02, 2025
As an anxious Kelly looks on, the Headmaster punishes Daija soundly with a hairbrush.

Madison: Red Cheeks
Updated: Mon. Jun. 30, 2025
Madison is punished for her cheeky attitude.

Mila: Long Hard Punishment with Paddle and Hairbrush (Part 2)
Updated: Fri. Jun. 27, 2025
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.

Mila: Long Hard Punishment with Paddle and Hairbrush (Part 1)
Updated: Wed. Jun. 25, 2025
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.

Five Girl Punishment (Part 2)
Updated: Mon. Jun. 23, 2025
Daija, Bridget, Heather, Lynn and Amber, all completely naked, are punished together by the Headmaster in the bedroom with paddle and strap.

Mila: Late for her Meeting with the Headmaster (Part 2)
Updated: Fri. Jun. 20, 2025
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.

Mila: Late for her Meeting with the Headmaster (Part 1)
Updated: Wed. Jun. 18, 2025
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.

Daija: Where's My Money!
Updated: Mon. Jun. 16, 2025
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.

Zara: The Punishment Room
Updated: Fri. Jun. 13, 2025
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.

© Alpine Entertainment Group Inc. 2009