Original Spanking Art — Darcy 10: School Caretakers

More Darcy from the archives — four original drawings with narrative on the theme of school caretakers.


Middlemiss Academy for Young Ladies is a high-end private educational establishment with a reputation to protect. So any girls caught misbehaving on, or off, the property are dealt with in a firm and traditional manner. Here we see Ashley and Elizabeth, waiting for their punishment in the hallway outside Mr Briggs’ office as is the custom. Both were caught vaping behind the janitor’s shed. A very silly place to hide, seeing as the janitor — that’s Arthur sweeping the hall — is a real stickler for the rules. In fact, the girls are convinced he spends more time snooping around trying to catch them out than he does actually looking after the school. And he always seems to have a job to do in the hallway or outside of Mr Briggs’ window when the smacking and the caning and the strapping and the tawsing and the belting and whatever else Mr Briggs sees fit to dole out — is going on. Arthur does so love his job.

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Silly girl. Mr Smith, or Smiffy, the caretaker, caught Amber with one of the boys from town. Don’t let her innocent look fool you. She was giving him a most experienced looking hand-job in the bushes by the school gates. Smiffy had the presence of mind to film the whole thing on his phone. But he’s given her the choice. He won’t show the headmaster — or her parents — providing she visits him once a week in his equipment room. This is her second visit and she knows what to expect. A good talking to, followed by a spanking and then the cane. And when the caning gets too much, she offered Smiffy the same relief she gave her young male friend.

Unknown to Amber, Smiffy is filming each of these sessions as well.

Today he plans to cane her even harder. Let’s see what she offers him to make it stop…

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Saturday morning at Davies Lane school. While the boys football team played at home, these four miscreants were caught red-handed by Jimmy the caretaker stealing from the boys bags in the changing room. ‘What’s it to be you thieving little bitches? I tell the headmaster and you get expelled? Or you come to my workroom and take 12 of the best on your bare bums?’

The girls agreed to take the punishment. But Jimmy insisted that the visiting team get to watch through the basement window.

‘Come on girls. Let’s get on with it. Everything off then touch your toes. And let’s see who we can get to cry the loudest.’

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Lucy had been very careless. For several months she had been meeting with “sugar-daddies” she connected with on-line.  She was always careful to meet them a long way from St Swithins, the boarding school her parents paid a pretty penny for her to attend. But her latest liaison had been insistent they meet near the school. And that she bring her uniform.

They met at The Queens Arms in the neighbouring village. Lucy knew she’d be well rewarded for her time. But unluckily for her, Mr Banks, the school caretaker, was also there.

Girls were strictly forbidden from visiting pubs, much less meeting with boys — or in this case men. He took a couple of photos in case he might get the opportunity to apply some pressure to the winsome Lucy. They were incriminating, but not enough to get what he hoped for. So he followed them out to the car park.

His heart raced when he saw Lucy climb into her male friend’s car. Creeping closer he saw her wriggle out of her clothes and change into the St Swithins blazer and skirt. Phone at the ready he managed to get a clear view.  The pictures he took of Lucy in her uniform, getting first a spanking and then a good hard seeing to, were all he needed.

Next day, confronted with the evidence, Lucy was offered a trip to the Headmistress — which would lead to instant, shameful expulsion. Or a weekly visit to Banks’ “office”.

That all happened ten weeks ago. Lucy knows what to expect now. A long hard punishment followed by a long hard caretaker inside her. Banks keeps her knickers as a souvenir. Today he plans to cane her extra hard…

Comments

  1. Excellent stuff, Darcy. Just when a girl thinks she can do as she pleases, with all the masters safely in the staff room, the trusty caretaker is there to take advantage when she engages in activities that she shouldn't.

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  2. New Moral Order31 March 2023 at 08:47

    Ah yes, indeed, the school caretaker! One of the most beloved and enjoyable archetypes in all of Blushes' spanking lore. These cackling, uncouth, lecherous, wily, sometimes quite brutish, and always very dirty and smelly old men are every pretty sixth form schoolgirl's worst nightmare. The thought of one of them achieving any form of close or intimate contact with their fragrant and lithesome young persons has to be one of the most vomit inducingly flesh crawling scenarios imaginable. Unfortunately for the Annabels and Sallys of this world, these chaps' every waking moment is commited to doing just that, and quite often succeeding!

    I have to diverge slightly from Darcy's excellent depictions here. The 'Miss Hobson's choice' frequently presented in these stories is not one between expulsion and the (caretaker's) cane but between the Headmaster's cane and the caretaker's desire for various and often unspecified (it frequently being left to the reader's imagination) depraved versions of 'the other'. Doubtless the caretaker would cane them if he could but he'd surely lose most of his 'bargaining power' if he did so. I'm sure a good spanking would be in order, however, together with whatever else he chooses to do with them.

    I must say that I find the juxtaposition between the headmaster's caning on the one hand and whatever else the caretaker wants to get up to more pleasing than that between expulsion and a caning from the caretaker. Firstly, I think most of the offences the caretaker keeps a vigilant eye open for spotting - running or talking in the corridor, arriving late for lessons, taking a forbidden shortcut across the school lawn to avoid being late for a lesson etc. - are too trivial for expulsion, but nevertheless excellent caning fodder for the Headmaster. Secondly, is expulsion that dreadful a sanction anyway? Yes, I know, all dreadfully shaming for one's parents etc., what with the school fees they've paid out etc., but I can't help but think it's all too easy a way out for the recalcitrant young Miss! Plus, the Headmaster wants to keep hold of his nubile young lovelies, not lose them! Thirdly, it's just a much more interesting choice between the sheer agony of the cane on the one hand, and the repulsive, clammy attentions of the caretaker on the other, with young ladies often reluctantly plumping for the latter. Just rather interesting how the terrifying threat of the cane concentrates the schoolgirl mind into contemplating, and ultimately acceding to, what was previously and horrendously the unthinkable. Also has the benefit of taking them down a peg or ten sexually. As we know, the rod of flesh can be just as effective as the rod of rattan in certain ways!

    Excellent drawings though, Darcy. I'm particularly charmed by the final one, with the parade of girls' knickers hanging up in what is presumably the boller room - the caretakers' previous trophies or 'scalps' no doubt. I'm sure he finds fun things to do with them also, even when their owners are not present.

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