The Headmaster and Hackett

The Headmaster and Hackett


A senior boy has been up to no good and upsetting the English class teacher. The boy in question Hackett (Jerry Bosak) is up before the Headmaster to explain himself. Its not good to get a far as knocking on the Heads door as it will almost certainly mean a tough disciplinary session for this misbehaving senior.

这名淘气的男孩Hackett(Jerry Bosak)现在站在校长面前,为他自己辩解。偷窥校长办公室的门可不是什么好行为,所以毋庸置疑,这名不守规矩的高年级生将得到严厉的惩罚。

The Headmaster makes Hackett wait for his punishment.


Hackett is ordered to take his blazer off and bend over for the cane.


First on his grey trousers now tightly wrapped around his backside.



Click here or on the Read More Tab below to see more pictures



Then on his shorts …

eventfully the bare bottom.

Hackett is in the sports team and has a particularly appealing bottom when it comes to a receiving a caning.


Like all naughty lads, afterwards he’ll do some corner time nursing his scorching buttocks, before taking a spanking.


He takes this with difficulty though especially over the now sore stinging cane welts received earlier!


Jerry Bosak plays Hackett




The Headmaster and Hackett – in 1080p Extra High Definition


The Headmaster and Hackett – in Standard Definition



This video will also be available through Sting Raw at Clips4Sale shortly, for customers who wish to use an alternative processor.

Sting Pictures


Title 2257

3 comments on “The Headmaster and Hackett

  1. This video is a real treat. I have been critical of the just-bend-over-and-take-it position in the past and I would like to clarify what’s different about this video and why I like it. First of all, the filming and editing of this is top-notch, and Jerry looks spectacular. What gives this release an edge, however, is its believability and authenticity: Jerry’s pants remain around the ankles and he grabs his ANKLES, he doesn’t merely rest his hands on his knees; likewise, his knees are quite bent and his legs are not locked. This makes all the difference: Jerry appears more submissive, as he should, and having to maintain the position enhances the painful nature of the caning. His vocal “ows,” while standing in the corner, are an unexpected highlight. Rich is, as always, great, and the phone call — which has been an important detail in other recent videos– is well employed here and distinctly dramatic and erotic. A straightforward, no-nonsense video and I recommend it!

  2. I concur with HRHs comments.
    It is a real treat to see a boy properly bending over however, I do prefer the touching toes stance.

    Jerry has opened a new dimension to Sting productions and its nice to see a muscular boy who has an open face and looks close to the part of a sixth former. Of course I still adore the likes of Robin, Andy and Richard etc.

    He was truly well caned and spanked by Rich as evident by the fierce looking cane welts on his bottom and its complete redness after a hard spanking. This looked a very authentic act of discipline not like some of the held back scenes necessary when some models are engaged.

    Thank you indeed Rich and Jerry.

  3. I know I say this all the time but I just love this play-out… Caned (with some good sore welts) then spanked OTK its just such a great combination and Stings approach is so fantastic having the lad getting the most severe punishment which is the cane then having to get hand spanked on top is so stimulating to my spanking brain! Sting have done this many times and its always a very hot set-up. My favourite is when the lad is spanked at school then by his father at home as someone mentioned above having the phone-call is then important. I think Jerry looks great in this particular clip his body looks sexy and I love the white socks and this pictures is is nice I am getting Travis vibes from Jerry I suppose that is a rather good thing.

Leave a Reply

Your email address will not be published.