The Headmaster and Mr Flint

The Headmaster and Mr Flint

It’s not only senior lads who can fall foul of the strict college rules that have to be followed. The Headmaster set a precedent that all the newly appointed junior staff would get the same punishment as older lads might expect rather than face dismissal for any infraction. This seemed to be working well and in this way no junior staff member would lose their jobs.


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One such staff member, the junior coach, Mr flint (Ryan Conway) had got himself in to trouble and was reporting to the Heads study to explain himself. There seemed little room for manoeuvre and soon he found himself bending over to take punishment like any sixth former he too might have had to deal with!




The Headmaster and Mr Flint – in 1080p Extra High Definition

The Headmaster and Mr Flint – in Standard Definition


An HD version of this video is also available through Sting Raw at Clips4Sale for customers who wish to use an alternative processor.

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10 comments on “The Headmaster and Mr Flint

  1. It’s just the cat’s ass to see Richard back in action, and administering a good thrashing with his snappy, supple cane across young Ryan’s deliciously pert and cheeky bottom, looking so smackable in those jeans, with a hint of waistband. so full of Eastern European promise! And as the jeans come down, the promise is more than filled with a pair of conservatively coloured, but nonetheless coloured briefs, which, are the perfect length to frame his naughty bottom for the hard discipline that Richard is laying on with his customary severity! That thrashing across his bare bottom seemed finally to have brought back some eye-watering memories!

  2. Ryan looking exceptional. This is great – Ryan in his tight jeans bent over the bench withComment
    a glimpse of his underwear over the waist of his jeans. And what a treat we hen we get to see his tight dark grey underwear. Would have been great to have some more photos ( a lot more) of Ryan in his tight underwear.
    Great to see Rich back in front of the camera and delivering his no nonsense approach to Ryan. This makes for a superb video.
    Thanks for including Ryan on the receiving end – good to see some slightly older hunky guys put in their place – especially by Rich. Would like to see James Holt put in his place again soon.
    Ryan & James Holt would like great in suits in an office scene.
    If Sting would consider including more photos of certain videos – would be agreat addition. (for purchase) been great to have a series of Ryan in his tights jeans and underwear over the bench.
    One final comment can Sting get Finn in some tight dark briefs under those short shorts receiving a good hand spanking on the seat of the shorts and underwear…………….just a suggestion for the future.

  3. Tip of the hat to the Good Doctor. Didn’t see your review until after I posted mine. Succinct and colorful comment. Mine was a bit of a ramble but seems we both enjoyed this video.

  4. Great minds definitely think alike when it comes to the discipline of those cheeky young Stinglads, Ethan!

    I would add my voice to yours, as I believe I have done before, in calling to see young Finn laid over the knee and spanked in those bottom-hugging shorts, with dark-coloured briefs underneath – preferably navy-blue or maybe black!

    How about it, Sting? The only props required are a chair for the spanker to sit on, school uniform including the short shorts, a pair of dark-coloured briefs (as opposed to boxer-briefs, Finn’s habitual preference in underpants) and a hard hand! And Finn the Lad himself, of course. You’ve got two takers here – and I’m sure there’d be others. It would be the realisation of a dream and one I’d be prepared to pay more for!

  5. Thanks for the very hot Mr Flit getting a good caning. Great video, I hope he get many more caning to save his career, Very hot starting in tight jeans which is his case set such an enticing target, But of course ending bare butt bent with the bench to keep legs just wide enough apart. More of these please, and the same to master James Holt and Finn in similar position for te cane (with and without his short shorts and speedo style underpants.

  6. Mr Flint (Ryan) looking hot in tight jeans defintiely needs some more. And after reading the comments, Finn in some tight dark briefs gets my vote too Finn looks great in tight jeans short shorts and tight boxer shorts lets see him in some briefs too – Merci.

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