Sting: T​ales from the Headmaster’s Study 11 – ​ Wheals of Misfortune

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

7 Responses to Sting: T​ales from the Headmaster’s Study 11 – ​ Wheals of Misfortune

  1. Just watched this. This film is absolutely perfectly done. The scenes are very convincing and the acting from all concerned was just spot on!
    I can highly recommend this film. Don’t miss it!

    P.S. I admit to just being a tiny wee bit biased because Jonathon is in this one.

  2. Avatar Anonymous
    Anonymous says:


  3. Avatar Anonymous
    Anonymous says:

    Richard dear boy, your product can hardly be bettered but your spelling needs to be supervised. First we had “Something to wine (sic – whine)about’ and now we have ‘Wheals (sic – weals) of Misfortune’.
    I appreciate the attempt at punning, but you must go to the bottom of the class, and report to the Head for correction . . .

    • Avatar Anonymous
      Anonymous says:

      With respect “wheal” and “weal” can both mean the same thing, a raised and reddened area of skin also known as a welt in fact the plural is generally spelt with an “h”

      As to “Whine” and “wine” in “something to ‘wine’ about”, that was obviously a play on words in that the boys were punished over stolen wine.

  4. This is a masterful journey into male spanking erotica, the sight of Xanders pert rump displayed over Rich’s firm knee was a joy to behold, he is iftly becoming one of my favorites, up there with Rudi and Matt Mills, even though he is rather more twinky

    Jonathon was perfect as well, and a very accomplished actor. It was so hot that Jonathon got a painful injection in each butt cheek just before he went on to get repeatedly spanked on those same aching butt cheeks, what a perfect scenario, and what perfect butt cheeks for such punishment.

    Toby is also a great performer, who can take a lot of punishment,he is a very reliable Sting actor.

    So, all in all I really can’t fault this episode

    Love that Sting have started including a series of rapid file slaps toward the end of the spanking, just when the boy’s bottom is getting to its most sensitive.

    The guys at Sting know what they are doing, I can’t recommend this enough. It is a Disciplinarian’s Delight

    Kudos to all cast and crew

  5. Avatar Anonymous
    Anonymous says:

    Tom Eisenburg is good as a spanker, he hits the sit spot. He is also very good at being scary

  6. Avatar Nathan Roper
    Nathan Roper says:

    This has to be one of the sexiest spanking movies I have ever seen. Every thing about it comes from the deepest hottest fantasy. Everything!!

    More like this please