Your Search Returned 1080 Results
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
© Alpine Entertainment Group Inc. 2009