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The HeadMaster

The HeadMaster

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Videos

11 videos featuring The HeadMaster

Strapped Bare 00:04:39
Strapped Bare
May 13, 2026
Without Her Knickers 00:04:01
Without Her Knickers
Mar 4, 2022
Commnunication - Passing Notes in Class 00:04:07
Commnunication - Passing Notes in Class
Jul 5, 2020
Simpson OTK Spanking 00:05:42
Simpson OTK Spanking
Apr 14, 2024
The Book Collector 00:09:02
The Book Collector
Apr 25, 2022
3 Caned 00:17:30
3 Caned
Jul 18, 2022
Susan in Trouble Again 00:06:27
Susan in Trouble Again
Aug 15, 2022
4 Girls Spanked 00:12:56
4 Girls Spanked
Jun 26, 2026
Lesbians Caught 00:17:02
Lesbians Caught
Dec 2, 2021
Tuesday Discipline 00:07:59
Tuesday Discipline
Aug 2, 2020
Late Again Spanking 00:05:29
Late Again Spanking
Nov 28, 2021

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