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!

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.
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.


Certainly these lads have turned an unlucky Wheal of Misfortune.
(Jonathon a appears courtesy of the Magic Spanking Factory)




Running Time: 00:30:32


By Bruce

7 thoughts on “T​ales from the Headmaster’s Study 11 – ​ Wheals of Misfortune”
  1. My goodness jonathon and xander hard to decipher who has the best bum. Both are beautiful and ripe love to rim them both at the same time. Xander looks wonderful in a thong his globes are so creamy and juicy as for jonathon so so nice I would love to suck both their cocks rim and then fuck them both. Great work guys. Perhaps Jonathon should have his arse eaten by xander.

  2. Anonymous– Great clips. both these young,an have very hot bodies and also very hot Hides from the punishment they got and deserve

  3. If Richard and Robert would like to take a break, I would be very willing to baby sit for them.

    You could be confident the boys would learn to behave

  4. Jimbar — In addition to a Red Hot Cast We have a couple young men who have a. red Hot and a very Sore. Hiney .Imdoubt very much if either of these young man will be siting down in the immediate future.Perhaps this lesson and learning experience will serve these men well .One thing for sure what these two young men got will be a Ass Whipping to remember The clips were excellent the various positions in assuming the position were more Good

  5. I downloaded this on the recommendation of a friend and it is quite incredible. The production values are better than any adult movie I have seen ever, it could be a mainstream production (except for all the bare bottomed boys getting spanked)the acting is also very professional, including by the young actors, which is also most unusual.

    I am biased because this wonderful movie includes one of my ultimate fantasies of a boy getting an injection in both buttocks and then getting spanked. That is so cool.

    And what a handsome he new guy Jonathan is, I wish he has less of a tan line, but otherwise he is perfect. That final scene with the German teacher is wonderful, although a couple of tears would have been the icing on the crispy creme

    More like this please.

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