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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 area below

By Bruce

33 thoughts on “Caption quiz”
  1. Boy: “Not that strap again Sir! I still can’t sit down from the last time!”

    Master “And you won’t sit down before the next time either!”

  2. Well Ok…I guess, if you think it will help somehow. But I think you should get your glasses, I’m the math TEACHER! Not the wayward student.

  3. “Do you think that with this belt we’ll have a better go than with the previous one?”
    “I can’t say yet, it depends on how many belts you still have in store for me, sir.”

  4. “Seriously? I’m so sore from your hand spanking, now you’re going to belt my behind? What’s next, you going to cut a leg off this desk and shove it up my ass, too? Please, Sir, no more, I’ll be good!”

  5. “Ok, according to the book, the next step is 25 across your bare butt with this belt. I think I like this parenting guide by Larry Townsend.”

  6. It’s very good quality leather ,Sir, and our outfitting department has trousers that go with it.

  7. Yes Sir thats the belt I meant. I really enjoyed it last time and I could see by the damp patch in your trousers that you did too.So lets both enjoy ourselves, Ill tell you when Ive had enough and then we can jerk each other off.

  8. Harsh, happily-haphazard-hoodlum-he-hood-hush-hardening-heeding headmaster hisses heartily to hellhound-harshly hard-handedly howling-humble-hound hollerer Hollis “Count yourself lucky, lad: the next two dozen may be the last lashes leathering your lazy-lout-lower limbs limp lava-lividly with the belt if I’m pleased with the letter you’ll write, while remaining remorsefully-red-reared rigidly-rules-reminding-rebel-rump-roasted in the perfectly-perilously-pantless-puerile-posterior-presenting-pupil-punishment-position I prefer protracted, to thank your superiorly-sane sound-stripped-scoudrel-squirt-spanking-sessions-severity-sympathizing step-uncle the saddler on behalf of your mischievous mate-cahoots-cohort for his generous donation to our school in the mail : at its arrival, all classes, corridors, common-quarters and staff offices will be foppish-fledgling-fanny-fierely-flagellating-fit-furnished fast and forever with first-rate flogger-fun-feast-fit flails, just as every room at your home when your firm, flogging-fond father finds his equally generous gift – three-tail tawses to the toughest thuggish-teen-twacker’s taste, to thriftily thrash thy trouserless-trembling-truant-trash-tail tender-tanned to true-tears time and time to teach thee and them thousands of things and train timeliness and total-tractibilty tremendously-thougher, ‘t-is top-time for thy thorough teachers therafter!”

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