The Housemaster’s Study 16

The Housemaster’s Study 16

Its not a lucky day if you know you are in deep trouble and have to report to the Housemaster’s study. Today is Jackson’s (Finn Harper) worst nightmare, he is reporting to Mr Conway (Ryan Conway) and of course will be unable to explain away his recent misdemeanours detailed in a letter. It can only end one way.

And so it does as the boy bends over to take the first session of the cane. Starting on his tight shorts ..


Click on the Read More tab below to see what happens next!!




It will come to an end only when a good set of stinging cracks have scorched his defenseless bare bottom. In actually fact its is only the penultimate end.

Next will be the traditionally long, over the knee, spanking on the boys already raw, previously caned, bare bottom. Jackson will certainly leave the Housemaster’s office today knowing he’s been properly dealt with and that perhaps also he well deserved it!

The Housemaster’s Study 16 stars Finn Harper and Ryan Conway




The Housemaster’s Study 16 – in 1080p Extra High Definition

The Housemaster’s Study 16 – 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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30 comments on “The Housemaster’s Study 16

  1. Great to see Finn being caned and spanked again, Another 10 out of 10 production and as to those shorts doubt if they could be shorter and how is lovely bottom filled them out. They also showed of his long thighs and legs, Brilliant

  2. Also should have said how nice it was between the caning and spanking to see a boy start to get hard and trying to hide his embarrassment!!!!!

  3. What a wonderful video this is. The delightful, and ever more handsome, Finn in those tight shorts, in trouble again!! Thank goodness for we voyeurs!

    Ryan Conway certainly made his mark on Finn with Finn coming up with some new facial expressions and a few different sounds.

    Ryan makes good top and I hope we see lots more of him in that role – he does though need a few lessons in the art of caning. He was too close to Finn and used the middle of the rod to do the work. It wrapped around Finn’s rump and caused much more damage to the right side than to the left. Practice will make perfect though and I am sure Sting will assist with that.

    Well done Finn and Ryan.

  4. From Finns sharp haircut to his perfectly fitting underwear and yes those tight shorts – this is a visual delight. Perfect 10. Photos are great too particularly the last cheeky photo. Great video where Finn and Ryan are at their best. Thanks Sting this is a winner.

  5. Oh dear those shorts look awful I really dislike them there not even that tight just very skimpy almost like female shorts that look very odd I have suggested some brilliant clothing wear to Rob before now which Finn would look so much better on but three shorts I can’t take it seriously. T his is so unappealing to the younger audience.

    • Thanks for your feedback Luke, Sting value all perspectives even though you seem to be in the minority camp on this issue.

      • Now, there, Bruce, I really have to stick my oar in and say a resounding ABSOLUTELY! Those short shorts, especially being filled out by young Finn’s deliciously smackable bottom, are exactly what so many of us have been waiting for! For gentlemen ‘of a certain age’ who grew up in the days when shorts truly were short, I’m sure that this video will bring memories, some delightful, some no doubt painful, flooding back!

        I’ve got to say, I’m not too sure of the lack of appeal to the younger audience either. I don’t know about anybody else, but I’ve noticed in just maybe the past couple of years that shorter shorts seem to be making a comeback with young lads – no doubt the widespread fashion for boxer-briefs as underpants has contributed to this since they allow for the wearing of shorter shorts. And as it happens, I was in my local outdoor store recently for some climbing gear when I heard a lad, who could have only been in his very early twenties, ask the assistant in the clothing department if they had any shorts that were shorter than the ones on display. While they didn’t have what he wanted, the assistant was able to recommend a shop that could help him! I might be wrong, but I have a feeling that younger lads who were into spanking would love this video!

    • The shorts are VERY hot, and Finn with his beautiful legs looks particularly hot in them. I spontaneously asked a few people yesterday (all in their twenties, all members of what you call the “younger audience”), and all of them without exception agreed that the shorts were hot. Some of them would have preferred something like Adidas-style shorts, the others found the grey school-uniform trouser style hot. But they all agreed in unison that Finn should only wear shorts of that length, which put his lickable thighs on full display.

      More of Finn in these shorts please, Sting!

  6. Donner und Blitzen! Und fishfingers! Well, we asked for it and young Finn got it! Boy, did he not half! This spanky little video really is the baboon’s buttocks! I think that of the naughty schoolboy scenarios we’ve seen this drop-dead gorgeous young lad in, this is the best one by a long way – and that’s with some STIFF competition! (Come to think of it, that’s not the only thing that’s stiff round here right now, haha!)

    I know I’m not the only one who wanted to see Finn disciplined in a pair of short, tight school shorts, and as he came into Mr. Conway’s office, the word ‘PHWOOARR!!!’ just exploded from my lips! Even from the front, he looked so incredibly spankable, if I could have lifted him off the screen and laid him over my knee there and then, I would have done it! The shorts are the perfect length for punishment and I thought, ‘He’ll have to have a good short pair of underpants on under those short shorts! I wonder what colour they are?’ More of that in a moment.

    Finn has a delightfully provocative way of bending over – not the traditional ‘Touch your toes! Legs straight!’ approach, but with his legs sufficiently bent to make sure his bottom is sticking out quite cheekily! I don’t know if he assumes this position consciously, but if it’s accidental then it is a very happy accident! The observant among us will have noticed the vague outline of the legs of Finn’s underpants standing out just above the leg-line of his shorts.

    The wayward youth’s expression when he catches sight of the rod that is not going to be spared is priceless, and as Ryan begins to lay the supple cane across Finn’s bottom, it is clear that he knows what he’s doing, even though I’m sure this must be the first time, on film at any rate, that he has caned a lad. There might be a case for saying, as one fan has suggested, that the cane will sting a boy’s backside more if the tip of the cane is applied to it, but when we get to see the red weals that have been raised across Finn’s bum, there is no doubt about Ryan’s skill – even if it might take a little honing! And no doubt the other Sting spankers will be more than ready to assist with his training in that respect!

    When the magic moment comes when Finn is ordered to take his trousers down, he is revealed to be wearing perfect punishment underpants! Black, my third favourite colour for spankingwear, tight and, again, the optimum length to frame the boy’s bottom for the severe corporal punishment that is being laid on! And what I like about this particular selection from Finn’s pants-drawer, is that there are no seams up the seat to mar its smoothness! I am always slightly disappointed by boxer-briefs with such seams – my own naughty boys never wear them, at least not when they have to report to me to receive well-deserved chastisement! Anyway, down come the boxers eventually to reveal the raised welts which, alongside Finn’s reactions to the hard strokes of the cane, show that Ryan’s new-found skills are certainly shaping up! I don’t know what anyone else thinks, but I do get the impression that Ryan starts to lay the cane on harder after Finn takes his shorts down. Perhaps the site of the lad in those tight black boxer-briefs was spurring him on to fresh efforts – I know it would have done had I been wielding the cane!

    It’s at the moments like when Finn has to strip naked to be laid over the knee for a good spanking that I find I am reminded of just how gorgeous he is! And although we’ve seen him shirtless before now, I think this is the first time I’ve noticed what a whippable back he has – beautifully straight and nicely tanned! What fun I could have with my cat-o’-six-tales across those shoulders!

    After forty-one hard strokes over the backside with a swishing, stinging cane, it must have been hard for Finn to have to be laid over the knee and feel Ryan’s hand good and hard across his very bare and hairless bottom, and indeed the fact that he, towards the end of his ordeal is at times looking almost tearful, very much bears that out! I love the clear discomfort he demonstrates as he gingerly and with obvious pain, pulls his underpants and then his short shorts up over his smarting bottom, bringing to a close a film that has gone straight into my folder of ‘Fave videos’, where Finn is in good company with Robin Palmer, James Lewis and Austin Cook!

    I have got to say about Ryan that, while it is always the cat’s ass to see him getting his own deliciously pert bottom smacked, I think he is brilliantly suited to his new role as a spanker – tall and muscular with a superbly stern expression on his face as he disciplines his young charges! His treatment of Finn says loud and clear: “I might be a young teacher, new to my job, but don’t mess with me, my lad!” I am sure it’s a role he’s going to grow into magnificently and I look forward to seeing how he’s going to develop it!

    Just a thought for the next time young Finn has to report to a master for punishment: could he wear those short shorts again? This can’t be the only time he’s seen in shorts that make him look SO smackable! And could he also be laid over the knee in them? A wardrobe combination that would work well would be the shorts and the bright-blue underpants he wore in ‘Marco takes charge again’. Just a thought – but I’m sure it would have a receptive audience!

  7. Great video and great to see these length of short trousers. Hope we see them again on other naughty lads.
    Would it be possible to put a school cap on a lads head as well at some point?

  8. Shoot, I commented on the Preview page by mistake. In short (pun intended!), great video, both men look hot. Dr Van S, I so enjoy reading your colourful reviews!

  9. Love the shorts on Finn but for the love of God PLEASE spank him in the seat of his shorts ! What’s the point in him walking in then just taking them off very disappointed

    • Hi Mike, I am sorry you were disappointed. Finn is caned on the seat of his shorts, but the OTK spanking occurs later in the video when he is naked. Perhaps in a future video the sequence will be reversed so the spanking comes first

  10. Perhaps there is a way to follow up what Mike is asking here, since I, too, have asked if we could see young Finn laid over the knee and spanked in those short shorts. Ryan’s words to the boy while he still has him laid across his knee, ‘No more notes!’ are surely just an open invitation, aren’t they?! Is it likely a naughty boy such as Jackson clearly is is going to get through the rest of his time at school with ‘no more notes’?! The way lies open…

    I really think that will be a winner!

  11. I agree with the good doctor – it would be good to see Finn spanked in those short shorts. Maybe in one of James Holt’s high over the knee spankings. Hopefully Finns new shorts will be getting plenty of use in the future. I particularly like Finns choice of underwear here – however Finn in a black or dark blue pair of briefs would be a firm request at some point. This update was excellent – great creativity in the photos and video.
    Ryan looked amazing here too so more of Ryan giving and hopefully still receiving at some point.
    As always please bring back Finn soon.

    • I would just want to endorse Ethen’s request to see Finn smacked in a pair of briefs! Preferably laid over the knee! He looks amazing in boxer-briefs, but briefs definitely have the edge when it comes to punishment underpants – and black and navy-blue are two of my favourite colours. They would go wonderfully with those short shorts!

  12. This video really is excellent! I bought this immediately I saw it was available – have been waiting to see Finn in shorts like this for AGES – thanks SO much everyone at Sting!

    Now that we know Finn fits into these shorts, hopefully there is no excuse to not get him into them again 😉

  13. Sting has a lot to answer for after Finn appeared in those shorts. It certainly has ignited a lot of imaginations.
    Hopefully it won’t be too long before we see Finn wearing them again – would it be possible to indulge us with an exteneded photo feature when the time comes? Certianly appreciated the photos this time but was left wanting a few (a lot) more of Finn in those awesome shorts. Patiently awaiting the sequel to this excellent video too.
    Would also love to see Luke Geer in similar shorts at some point. Is an update coming from Luke soon?
    Thanks Sting for all the excellent content

    • Completely agree with Ethan – there are just too many fantasies running through my head involving Finn in those shorts 🙂

      Are there more photos from this session Bruce? Appreciate there is a limit to the amount of free content Sting would want to be putting out – but I for one would certainly pay to see more shots of Finn posing in this outfit.

      Now that these shorts are out of the bag so to speak, I really hope we see them again on a regular basis 🙂

  14. In addition to more photos, maybe Sting could produce a “behind the scenes” version of this video or an interview with the models – I’m sure many fans would be happy to add either/both to their collections!

  15. Very nice little shorts! Please keep filming Finn Harper with these shorts and make him wear knee socks! This is the right outfit for a schoolboy. He has so pretty thighs and he is a very bad schoolboy. Cane him so much !

  16. It seems to me there’s a demand here that is just crying out for a response – I can’t remember when there were last so many comments! Let’s hope the response comes soon (might not be all that’s coming soon if I see young Finn laid over the knee in those shorts!)

  17. 10/10. And the amount of responses proof that. Have Finn again in and out of those short shorts for more caning., but do the same with Ryan. That said, Ryan does very well in the role of caner. Have him do that also again. I would actually love to see them getting the cane together

  18. Luke Geer would be a great candidate for the new short shorts. A video with Finn and Luke would be perfect. Is Luke being featured soon – he’s certainly been missed.

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