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Sophie & Madison: Adventures in Babysitting (Part 3) 1 Sophie & Madison: Adventures in Babysitting (Part 3) 2 Sophie & Madison: Adventures in Babysitting (Part 3) 3 Sophie & Madison: Adventures in Babysitting (Part 3) 4
Sophie & Madison: Adventures in Babysitting (Part 3)
The Headmaster offers instruction and guidance to Sophie in the proper techniques of discipline, as the two of them take turns spanking Madison.
Updated: Wed. Jan. 08, 2020
Sophie & Madison: Adventures in Babysitting (Part 2) 1 Sophie & Madison: Adventures in Babysitting (Part 2) 2 Sophie & Madison: Adventures in Babysitting (Part 2) 3 Sophie & Madison: Adventures in Babysitting (Part 2) 4
Sophie & Madison: Adventures in Babysitting (Part 2)
The Headmaster offers instruction and guidance to Sophie in the proper techniques of discipline, as the two of them take turns spanking Madison.
Updated: Mon. Jan. 06, 2020
Sophie & Madison: Adventures in Babysitting (Part 1) 1 Sophie & Madison: Adventures in Babysitting (Part 1) 2 Sophie & Madison: Adventures in Babysitting (Part 1) 3 Sophie & Madison: Adventures in Babysitting (Part 1) 4
Sophie & Madison: Adventures in Babysitting (Part 1)
Sophie and Madison's babysitting adventure continues. When Sophie is unable to tame a wild and undisciplined Madison, the Headmaster is forced to step in to deliver some old school discipline to both unruly girls.
Updated: Fri. Jan. 03, 2020
Amber: Unauthorized Party 1 Amber: Unauthorized Party 2 Amber: Unauthorized Party 3 Amber: Unauthorized Party 4
Amber: Unauthorized Party
When the Headmaster learns that Amber organized a social gathering without first getting his approval, all hell breaks loose! The Headmaster orders her to remove her skirt and put her hands on the wall. He alternates between strap and paddle for a vary painful punishment.
Updated: Wed. Jan. 01, 2020
Daija: After School Spanking 1 Daija: After School Spanking 2 Daija: After School Spanking 3 Daija: After School Spanking 4
Daija: After School Spanking
Daija, still in her adorable school girl uniform, is welcomed home, after a hard day at school, by the Headmaster.
Updated: Mon. Dec. 30, 2019
Brooke: Getting Dressed (Part 2) 1 Brooke: Getting Dressed (Part 2) 2 Brooke: Getting Dressed (Part 2) 3 Brooke: Getting Dressed (Part 2) 4
Brooke: Getting Dressed (Part 2)
With the Headmaster's careful supervision, Brooke continues to get ready to go out. He sends her on her way with a loving and tender OTK hand-spanking.
Updated: Fri. Dec. 27, 2019
Brooke: Getting Dressed (Part 1) 1 Brooke: Getting Dressed (Part 1) 2 Brooke: Getting Dressed (Part 1) 3 Brooke: Getting Dressed (Part 1) 4
Brooke: Getting Dressed (Part 1)
Wearing only panties and pearls, little Brooke goes over the Headmaster's knee for some OTK. He then sends her to dress, interrupting her at regular intervals to continue her punishment.
Updated: Wed. Dec. 25, 2019
Daija: Painful Caning 1 Daija: Painful Caning 2 Daija: Painful Caning 3 Daija: Painful Caning 4
Daija: Painful Caning
The Headmaster gives Daija a healthy dose of a thin wickedly painful cane on her bare bottom.
Updated: Mon. Dec. 23, 2019
Brooke: Playing Dress Up 1 Brooke: Playing Dress Up 2 Brooke: Playing Dress Up 3 Brooke: Playing Dress Up 4
Brooke: Playing Dress Up
Brooke's Day of punishment continues. After an OTK hand spanking, she is ordered to get completely naked, then change into a lovely summer dress, before going back over the Headmaster's knee for an additional dose of OTK punishment.
Updated: Fri. Dec. 20, 2019
Daija Spanked for Not Cleaning Kitchen 1 Daija Spanked for Not Cleaning Kitchen 2 Daija Spanked for Not Cleaning Kitchen 3 Daija Spanked for Not Cleaning Kitchen 4
Daija Spanked for Not Cleaning Kitchen
Daija learns that she had better clean the kitchen when told. Having not done so, she receives 201 slaps on her bare bottom as she bends over and kneels on the kitchen counter.
Updated: Wed. Dec. 18, 2019
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