You would think after his encounter with the birch block, Shipley (Tom Malone) would try to steer clear of trouble. Not a bit of it, he now finds himself having to report to his Housemaster (James Holt) for misbehaving before lights out! Now he’s in for a darn good spanking!
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Shipley Can’t Behave – in 1080p Extra High Definition
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Shipley Can’t Behave – in Standard Definition
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I recognise that some people have a thing for underpants, but I prefer the lads to not wear them with pyjamas & sports shorts, at least not all the time, so this is a big plus for me! Though it would also be really good if the punishment started on the bare, maybe even if only occasionally, so that the lad’s ass could be observed changing colour from its pristine to corrected state.
When will James be a bottom again?
Haha! As it happens. as one of the guys with a ‘thing for underpants’, I am fully in agreement that pants shouldn’t be worn under pyjama bottoms – simply for the sake of realism. I’m guessing there are young lads who do it, but none that are personally known to me.
There again, I’m talking as a guy who has never even worn pyjamas for bed since his university days. They tend to be most inconvenient garments…
Lol. I’m the reverse. Now I wear pyjamas all the time… except when I have to go out. The climate isn’t quite warm enough for that (much to everyone else’s relief).
Oh was getting so excited once the slippers came off..
And then boom they remained on the floor..gutted lol.
Think I would of thrown one at James to anger him enough to go back otk and feel that slipper burn 🔥
Great pics as always though.
James is looking good here would be great to see him featured with Finn again soon. Its been awhile. Can we expect to see Finn soon?
That ship has probably sailed but agree with Blake would be great to see James on the receiving end again too.
Appreciate the range of models Sting features and was great to see Rudi featured recently hopefully becomes a regular once again. Also the compilation videos are great for those of us who missed out on earlier productions
As I am firmly in the ‘thing for underpants’ can we see more underwear in future videos when the context allows. Thanks
Hairy buttocks means that your body is totally manly and needs double the swats given other students delivered extra hard.
That’s an interesting one, Bill. I’ve always thought of young Tom’s well-rounded bottom as being ‘downy’ rather than ‘hairy’, but that’s probably the effect created by his light-coloured hair. I agree totally about the manly aspect and the need for more smacks!
Good scene, but more than just spanking for this young man please.
And please, cane James again, he look so naughty and has such a deserving butt