Headmaster; Gallery

collegecastings timelockedincamelot talones kelsi monroe bigtits
silvertopdaddyspanker: Me as The Headmaster….and I’m an expert with the cane!
maletoserve: helloplumber: Having just escorted a boy she caught smoking to the headmaster, she list
striphernaked: peachstripe: Drawing possibly by Anton The headmaster sits watching the tearful girl
otkfme: Your headmaster is sick this afternoon so I will punish you.
(via The Smiths - The Headmaster ritual)
thefingerfuckingfemalefury: darkknightjrk: Future headmaster of the Jean Grey School for Gifted You
bottomsandmore: ‘Yes Headmaster, the results from my class haven’t been up to standard,
The Headmaster’s Officewatercolor,  ink, gouache
badboypeter: The Headmaster is not impressed with your slouching. He’s planning on correcting
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
queen-scribbles: “Thank you for your time, Headmaster.”“Happy to help, Miss Shrike
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
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