Headmaster;

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Headmaster’s Pensieve Hogwarts School, Scotland, UK Preposity takes a glimpse inside the W

The Headmaster’s Chair Hogwarts School in Scotland, UK Preposity takes a glimpse inside th

mrtwarse: Tammy was told to fetch headmaster’s cane for her punishment for being disruptive in

So would I, but I think we both know that isn’t likely Headmaster.

dadhikrav: Snape is the Headmaster of Hogwarts. 8th year

Elin and Headmaster Tom from GBS.

Brainstorm and his partner Arcana; together they form an Autobot Headmaster that I skipped over earl

dundee47: Spanked by the headmaster as the headmistress waits her turn with cane in hand.

yoomschoocs: Collab with @cara-kira again!!We drew the boys in suits, check out Cara’s profile

nbdsrc: gloriousfartjellyfish:Students with poor academic results end up on the headmaster’s l

Pokemon Combat Academy, pg 38-39Hey, looks like Gao woke up and is watching alongside Headmaster Gor

Join us this #SexySunday for Molly Malone’s brutal retaliatory caning on her former teacher, J

w00dgreen: When she saw the Headmaster was holding the 3 foot long ruler, she knew she was in for a

When a hair growth spell goes wrong, magic students Nimue and Ron are punished with a bare bottomed

Lilah the Eladrin Cleric. Daughter of the headmaster of the College of Hearthcrest, Lilah has spent

ffaiirrm: (via jennyispunished, cornertime) Outside the Headmaster’s office while he phones ou

Pokemon Combat Academy, pg 34-35Whoops, the guys got caught not doing their training, but Headmaster

twinkacademy: The Headmaster examines the newest of his young charges

messing with the professor(inspired by this post)

spank-my-dirty-mind: Source- Girls Boarding School The Headmaster told Amy first thing this morning

“Oh hey check it out, it’s my headmaster,” Gao said enthusiastically,

soonersilver: “It’s okay, Headmaster Stiffman. I know you didn’t mean to shoot

The Headmaster’s Secret Training Tape

mrspankyheadmaster:She was very naughty in swimming class, and sent to see the headmaster right away

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