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Daija & Amber: School Girl Paddling (Part 2) 1 Daija & Amber: School Girl Paddling (Part 2) 2 Daija & Amber: School Girl Paddling (Part 2) 3 Daija & Amber: School Girl Paddling (Part 2) 4
Daija & Amber: School Girl Paddling (Part 2)
The Headmaster puts troublesome school girls Amber and Daija through a classic school punishment as they are made to bend over and grab their ankles for a painful paddling.
Updated: Mon. Jun. 29, 2020
Daija & Amber: School Girl Paddling (Part 1) 1 Daija & Amber: School Girl Paddling (Part 1) 2 Daija & Amber: School Girl Paddling (Part 1) 3 Daija & Amber: School Girl Paddling (Part 1) 4
Daija & Amber: School Girl Paddling (Part 1)
The Headmaster puts troublesome school girls Amber and Daija through a classic school punishment with a hands on knees paddling.
Updated: Fri. Jun. 26, 2020
Maria: Preemptive After School Spanking 1 Maria: Preemptive After School Spanking 2 Maria: Preemptive After School Spanking 3 Maria: Preemptive After School Spanking 4
Maria: Preemptive After School Spanking
In a further effort to help Maria remain focused on school, the Headmaster gives her a preemptive OTK bare bottomed hand spanking.
Updated: Wed. Jun. 24, 2020
Daija: Homework Gone Bad (Part 2) 1 Daija: Homework Gone Bad (Part 2) 2 Daija: Homework Gone Bad (Part 2) 3 Daija: Homework Gone Bad (Part 2) 4
Daija: Homework Gone Bad (Part 2)
During a naked homework session, Daija decides to be difficult. The Headmaster lands in the middle of her with both feet.
Updated: Mon. Jun. 22, 2020
Daija: Homework Gone Bad (Part 1) 1 Daija: Homework Gone Bad (Part 1) 2 Daija: Homework Gone Bad (Part 1) 3 Daija: Homework Gone Bad (Part 1) 4
Daija: Homework Gone Bad (Part 1)
During a naked homework session, Daija decides to be difficult. The Headmaster lands in the middle of her with both feet.
Updated: Fri. Jun. 19, 2020
Bridget: 'Where's My Dinner?!' 1 Bridget: 'Where's My Dinner?!' 2 Bridget: 'Where's My Dinner?!' 3 Bridget: 'Where's My Dinner?!' 4
Bridget: 'Where's My Dinner?!'
Bridget is supposed to be making dinner. She is not. The Headmaster finds her napping. He delicately awakens the sleeping angel with soft cane caresses. Once he has her attention, she is spanked with a yardstick, a wooden spoon, a wicked thin cane and a heavy leather strap.
Updated: Wed. Jun. 17, 2020
Maria: Bench Belt Whipping 1 Maria: Bench Belt Whipping 2 Maria: Bench Belt Whipping 3 Maria: Bench Belt Whipping 4
Maria: Bench Belt Whipping
To help curtail Maria's continued flirting with the boys, the Headmaster lays Maria out over a bench and whips her already well marked bottom with a heavy leather belt.
Updated: Mon. Jun. 15, 2020
Daija: C on a Test 1 Daija: C on a Test 2 Daija: C on a Test 3 Daija: C on a Test 4
Daija: C on a Test
Daija, in her schoolgirl outfit, receives a painful OTK hand-spanking from the Headmaster for the C she 'earned' on a recent test.
Updated: Fri. Jun. 12, 2020
Kyndall: Polishing the Headmaster's Shoes 1 Kyndall: Polishing the Headmaster's Shoes 2 Kyndall: Polishing the Headmaster's Shoes 3 Kyndall: Polishing the Headmaster's Shoes 4
Kyndall: Polishing the Headmaster's Shoes
After a naked Kyndall is warmed up with a hard hand spanking she receives careful instruction from the Headmaster (and his crop) on the correct way to polish his shoes. The lesson finishes with additional OTK hand spanking.
Updated: Wed. Jun. 10, 2020
Stephanie & Desire: Bedtime Spankings 1 Stephanie & Desire: Bedtime Spankings 2 Stephanie & Desire: Bedtime Spankings 3 Stephanie & Desire: Bedtime Spankings 4
Stephanie & Desire: Bedtime Spankings
Pretty new girls Stephanie and Desire, dressed for bed, are put over the Headmaster's knee for good hard before bed spankings. Both girls end up naked and in tears before he finishes.
Updated: Mon. Jun. 08, 2020
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