Your Search Returned 1085 Results
Bridget: Unauthorized Piercing
Bridget gets her lip pierced. This is not allowed at the Academy. The Headmaster rewards her with a painful caning on her bare bottom.
Updated: Mon. Jun. 04, 2018
Mila: Rise and Shine
Sleepy Mila is awakened warmly by the Headmaster with a loving caress and a taste of the strap. She then goes over his knee for a brisk and invigorating hairbrush spanking.
Updated: Fri. Jun. 01, 2018
Daija: Hiding in the Woods
Daija, in a futile attempt to flee the Headmaster's wrath, takes to the woods. But alas, escape is not so easy and he catches her in the old abandoned building down by the river (some say it is haunted). Justice is swift and painful as the Headmaster skillfully wields the ping pong paddle of righteousness on the troubled lass' tender bottom.
Updated: Wed. May. 30, 2018
Five Girls Punished: Paddle and Hairbrush
Daija, Lynn, Amber, Heather and Bridget are gathered together in the living room. They are lectured by the Headmaster and then all five girls are paddled. The girls are then ordered to strip off their uniforms for some further OTK hairbrush spankings.
Updated: Mon. May. 28, 2018
Daija: Getting Organized (Part 2)
Daija was supposed to have all her paperwork organized. She failed to complete this task. Now she can't find anything. The Headmaster continues her punishment in her bedroom. She is laid out naked on her bed, her bottom propped up on pillows, and is spanked until sobbing with paddle and spoon.
Updated: Fri. May. 25, 2018
Daija: Getting Organized (Part 1)
Daija was supposed to have all her paperwork organized. She failed to complete this task. Now she can't find anything. The Headmaster gives her several spankings with a ping-pong paddle. He then orders her to strip naked and wait for him in her bedroom for additional punishment.
Updated: Wed. May. 23, 2018
Lynn: Bedroom Paddling with Witnesses
The Headmaster uses the heavy wooden paddle on Lynn in the bedroom as Daija and Heather look on.
Updated: Mon. May. 21, 2018
Daija: Drunk Again
The Headmaster finds Daija drunk and passed out over the arm of the couch. He administers a swift and painful punishment to the troubled lass with paddle and palm.
Updated: Fri. May. 18, 2018
April: Bringing up the Grade Point Average
New girl April continues her orientation at the Academy with a private counseling session with the Headmaster to discus her grades.
Updated: Wed. May. 16, 2018
Daija: Preemptive Spanking to Keep Making Money
Daiji, in her school girl uniform and thigh high socks, receives a long OTK hand spanking on her bare bottom from the Headmaster to encourage her to keep making money.
Updated: Mon. May. 14, 2018
© Alpine Entertainment Group Inc. 2009