Tales from the Headmaster's study Archives - Page 4 of 6

cane hand spanking Jonathon OTK strap Tales from the Headmaster's study Toby Haines Tom Eisenburg video trailers Wheals of Misfortune Xander Hollister

Trailer for Tales from the HeadMaster’s Study II “Wheals of Misfortune”

September 6, 2013 Bruce

Scroll down to view the preview video trailer for Trailer for Tales from the HeadMaster’s Study II “Wheals of Fortune” staring Toby Haines, Xander Holister and Jonathon You can either…

Jonathon soothing cream Tales from the Headmaster's study Xander Hollister

It’s a tough Job …..!

August 25, 2013 Bruce

Its hard labor but I guess someone has to do it! From Episode 11 of Tales from the Headmasters study is Wheals of Misfortune

cane hand spanking Jonathon OTK school strap Tales from the Headmaster's study Toby Haines Wheals of Misfortune Xander Holister

Tales from the Headmaster’s Study 11 – Wheals of Misfortune

August 22, 2013 Bruce

Episode 11 of Tales from the Headmasters study is Wheals of Misfortune staring Xander Holister, Toby Haines and Jonathon Well in to the term and prefect Brian Harper (Toby Haines)…

Alex Canley cane Conner Levi Dexter OTK school strap Tales from the Headmaster's study video trailers Xander Hollister

Video trailer for Tales from the HeadMaster’s Study (Episode 10) Student Vices

June 1, 2013 Bruce

Scroll down for the video trailer for Tales from the Headmaster’s Study (Episode 10) Student Vices Click here for the storyline plus high definition pictures Video trailer This 30.47 minute…

Alex Canley cane Conner Levi hand spanking OTK school sex scenes strap Tales from the Headmaster's study Xander Hollister

Tales from the Headmaster’s study (Episode 10) “Student Vices”

May 29, 2013 Bruce

Tales from the Headmaster’s study (Episode 10) “Student Vices” The students as ever get up to all sorts of things and the usual detentions and demerits get handed out. Whilst…

caption quiz Leonardo King Tales from the Headmaster's study

Caption quiz

May 12, 2013 Bruce

Click to enlarge Can anyone suggest an appropriate caption for this picture of Leonardo from Episode One of Tales from the Headmaster’s study? Please leave your suggestion in the comment’s…

cane Dexter hand spanking Kamyk Walker Kurt Maddix OTK school Tales from the Headmaster's study Tim Law video trailers

Video Trailer for Tales from the Headmaster’s Study (Episode 9) – Report to Mr Hiedrick

May 11, 2013 Bruce

Scroll down to view the preview trailer for Tales from the Headmaster’s Study (Episode 9) – Report to Mr Hiedrick Tim Law receives his first ever bare bottom spanking in…

cane Dexter hand spanking Kamyk Walker Kurt Maddix OTK school Tales from the Headmaster's study Tim Law

Tales From the Headmaster’s Study (Episode 9) – Report to Mr Hiedrick

May 1, 2013 Bruce

Introducing Tim Law in his debut performance The latest Episode of Tales from the Headmaster’s Study is Report to Mr Hiedrick, staring Kamyk Walker, Kurt Maddix, Tim Law and Dexter…

Kamyk Walker Tales from the Headmaster's study

Coming Soon from Sting

April 29, 2013 Bruce

Tales from the Headmaster’s Study – Episode 9 – to be released this week

cane Conner Levi Jesse Magowen Kamyk Walker plimsoll Rudi Vallance school slipper Tales from the Headmaster's study video trailers

Video trailer – For Days of Discipline

March 10, 2013 Bruce

Scroll down to view the trailer for the latest Sting download Tales from the Headmaster’s Study (Episode 8) “Days if Discipline”. Video trailer Click here for more pictures and the…

Trailer for Tales from the HeadMaster’s Study II “Wheals of Misfortune”

It’s a tough Job …..!

Tales from the Headmaster’s Study 11 – Wheals of Misfortune

Video trailer for Tales from the HeadMaster’s Study (Episode 10) Student Vices

Tales from the Headmaster’s study (Episode 10) “Student Vices”

Caption quiz

Video Trailer for Tales from the Headmaster’s Study (Episode 9) – Report to Mr Hiedrick

Tales From the Headmaster’s Study (Episode 9) – Report to Mr Hiedrick

Coming Soon from Sting

Video trailer – For Days of Discipline

You missed

Video Preview for CFNM : Now He’s Got The Message!

Sting CFNM: Now He’s Got The Message

The Video Preview for Another Painful Transaction

Another Painful Transaction

Category: Tales from the Headmaster’s study

You missed