Tales From The Headmaster’s Study 11

Staring Xander Holister, Toby Haines and Jonathon

Well in to the term and prefect Brian Harper (Toby Haines) has gotten himself in to detention again. How he keeps his badge is anyone’s guess!

Elsewhere, for his clinic appointment is Taylor Crosby (Jonathon) He has plans for later and that doesn’t include going back to school. He’s going to meet up with Watson (Xander Hollister) who we last saw being punished by the Headmaster for misappropriating another master’s funds, in other words nicking cash!

So there is justice in the fact that Crosby is going to start his day with a sore bottom when the doctor gives the deserving lad a painful injection in both bottom cheeks!

He doesn’t know it then but it will be a lot sorer very soon!


It’s the Headmaster who finds Harper sitting in detention. Unluckily for this hapless senior it’s the very classroom the Head is to take a lesson in. Annoyed that Harper is there in the first place he decides to mete out a faster and of course more painful reminder to behave. The senior perfect soon finds his bottom bared and a hail of stinging hand slaps connecting with his well-rounded cheeks.


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The now reddened orbs of young Harper are repositioned to meet the cruel leather strap conveniently left in the desk draw by Mr Roberts, whose classroom this normally is. The Headmaster wastes no time in putting this well used instrument to good use, the pale cheeks of this petulant prefect now burning with each lash.

Crosby and Watson didn’t get back to school that day and spent most of it in an amusement arcade. Their luck ran out however when they were spotted and this information was quickly passed back to the College. Unsurprisingly the Headmaster is furious. These two rascals are going to be severely dealt with and a good spanking for each of them is just a start!

Watson is first over the Headmasters lap

 Next the first stage of Crosby’s punishment begins

 If they think their ordeal is over they are very much mistaken

Being out of college without the knowledge of a master is a serious issue, one that needs firm correction. For this the cane is the only option. Both boys are ordered over the Heads study desk and a burning set of stripes is applied to both lads protruding and twitching backsides.

For young Crosby however this is just a start. His Housemaster Mr Eisenburg also the German teacher will be none too happy to hear of this episode. His method of punishment will no doubt be a very long and firm spanking, on an already very sore bottom!

Certainly these lads have turned an unlucky Wheal of Misfortune.

And unlucky Crosby was the sorest looser of them all

(Jonathon a appeared courtesy of the Magic Spanking Factory)


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Sting Lads – Only Fans

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By Bruce

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