A Tale of Two Canings
“Right Matthews, six more strokes and your caning is over,” announced Mr Jones the Deputy Headmaster in his soft, yet authoritative Welsh tones. With his trousers and underpants around his ankles, Alan Matthews breathed heavily and gripped the far edge of the desk ever tighter knowing that if the remainder of his caning was as merciless as the twelve strokes he had already received, his scorched and throbbing buttocks would feel like they had been positively flame-grilled by the time the cane finally came to rest.
Adding to this painful ordeal though, was the fact that Mrs Harwood the Headmistress had remained in the study for the duration of his caning. Although it was customary for two members of staff to be present whenever corporal punishment was being administered, the fact that one of them was not only female, but the Headmistress herself, was a point beyond humiliation for Alan.
Although in her forties, Mrs Harwood was an extremely attractive woman. Ever since Alan had gone on a fishing trip with classmate and friend, Jonathan Elliot along with Jonathan’s father, Alan had found himself entering into what was perhaps, forbidden territory for an eighteen-year-old lad, and had begun including the headmistress in many of his masturbatory fantasies.
“God, she’s got an amazing arse that headmistress of yours, pretty decent tits too, gorgeous woman, gorgeous woman,” Jonathan’s father had said as they sat patiently in the small, fibreglass dingy a mile or so from shore as they waited for the fish to bite.
“Certainly wouldn’t kick her out of bed, she’s a bit different to the headmistress I had when I was at school,” Mr Elliot had added with a grin.
With a slightly embarrassed look on his face, Jonathan had attempted to make light of his father’s comments, “Dad used to be in the merchant navy, spent months at sea without seeing any women so he gets a bit overexcited when he sees a woman he fancies.”
Mr Elliot pursed his lips and nodded his head as if confirming that what Jonathan was saying was actually true.
Alan had never really given any thought to Mrs Harwood’s personal attributes before that time. Miss Harrison the English teacher had certainly caught his attention, but she was in her early twenties and wore short skirts that displayed totally gorgeous thighs and every so often, as she leaned forward, she offered a fleeting glimpse of the lower part of her shapely, panty clad bottom. Mrs Harwood though, well she was the Headmistress, she just wasn’t someone an eighteen- year- old should be aroused by even if she was a good-looking woman.
The comments made by Jonathan’s father had though, somehow got Alan thinking. Mrs. Harwood was indeed an appealing woman and despite being similar in age to his mother, the ‘arse’ and ‘tits’ referred to by Jonathan’s father had suddenly become worthy of further consideration. Almost before he knew it, Alan found himself crossing the finishing line on many an occasion as he masturbated in the privacy of his bedroom to thoughts of Mrs. Harwood.
With a penchant for the female bottom and despite having never experienced anal sex, one of Alan’s most recurring fantasies was having Mrs. Harwood bent over the very desk that he now found himself bent over, and with her skirt raised and her knickers around her ankles, spanking and caning her ‘amazing’ arse before sliding his swollen cock deep into her beckoning anus as he kneaded her tender buttocks with his hands. At this moment in time though, Alan was fully convinced that he would never masturbate to thoughts of the headmistress ever again, in fact, his humiliation was such he may never masturbate to thoughts of anyone ever again!
As Alan once more felt the cane tap against his buttocks, he screwed up his face in anticipation of the agony that would soon follow and as Mr. Jones raised the cane high above his shoulder and brought it down with blistering force across Alan’s cheeks, it was all he could do to stay in position as he felt as though his buttocks were about to explode.
“AH, AH, OW...WOW, OW,” yelled the handsome, fair-haired teenager. “Thirteen Sir,” he added.
The next stroke soon followed and was similar in force, landing just a fraction lower on his buttocks.
‘OH, OH, OW, AH...... OUCH,’ he cried. “f******n Sir.”
With two more strokes swiftly applied, Alan contorted wildly, the searing bite of the cane making him wonder whether his bottom would ever recover from this terrible ordeal.
“Two more strokes Matthews,” announced the voice of the man from Harlech as he swished the cane through the air in preparation of the finale, causing Alan to flinch at the sound.
Out of the corner of his eye, Alan could see the headmistress unfold her arms and step up behind him to scrutinise his bottom. “I think Mr Jones, you need to aim a little higher on the boy’s buttocks for the remaining two strokes,” she said in her refined tones whilst pressing a fingertip against the part of his bottom that had yet to be challenged.
Displaying his bare backside to the Headmistress as he was being caned was humiliating in itself, but being referred to as a boy by a woman he’d included in so many of his recent masturbatory fantasies, was beyond humiliating.
Mrs Harwood continued to keep her fingertip pressed against the upper part of Alan’s buttocks, “The lower part of his bottom is already very marked and it’s best not to risk splitting any of those weals wide open, so place the remaining strokes about here and make them good and hard,” she added as she drew an imaginary line with her finger across the top of Alan’s bottom.
“Of course, Mrs Harwood, responded the Welshman as he adjusted his aim and offered the cane to the higher part of Alan’s cheeks.
Raising the cane for the penultimate stroke, Mr Jones thrust it downwards with all the force he could muster. As the cane cracked mercilessly against the tender flesh of Alan’s upper buttocks, another vivid red stripe was added to the colourful landscape he already presented. Grasping his buttocks with both hands Alan once more cried out, “EEEOWCH, OW-OW-OW....OH, OH……………S, S, s*******n………. Sir.”
“Back in position Matthews or you’ll get extra strokes,” snarled Mrs Harwood.
Without delay Alan returned his hands to the far side of the desk and firmly gripped its edge, the thought running through his mind that perhaps the headmistress was actually getting some sort of perverse pleasure out of watching his ordeal.
As Mr Jones addressed Alan’s bottom for the last of his eighteen strokes, the Headmistress once more intervened, “Grab your buttocks again Matthews and you definitely will get extra strokes, you’ll be given permission to rub yourself when I decide, is that clear?”
“Yes Mrs Harwood,” responded Alan. “Totally clear.”
After tapping the cane against the top of Alan’s buttocks, Mr. Jones once more raised it high above his shoulder and unleashed a stroke that nearly lifted Alan off his feet.
As the sound of the impact resonated around the study, the agony of the stroke felt to Alan like he’d had a red-hot poker laid across his cheeks.
“OW, WOW, WOW, OW,” AH, AH, OH, AH…..OH,” he yelled as he tightened his grip on the edge of the desk to avoid his hands straying towards his throbbing buttocks and running the risk of extra strokes. “Eighteen……S.. Sir,” he eventually added as he fought to recover just a little of his composure.
“Okay Matthews you may rub yourself now,” said Mrs Harwood. “When you’re ready, pull up your underpants and trousers and go home and don’t forget that first thing tomorrow morning you will come to this study and show me the letter of apology you will write this evening to Miss Danson for what you did to her car.”
“No, I won’t forget Mrs. Harwood,” responded Alan meekly as he frantically rubbed his throbbing bottom and resisted further pleading his innocence for fear of receiving more cane strokes.
Walking stiffly across the playground, Alan headed towards the school gates, grateful for the fact that he had been kept behind long enough after school for the playground to now be deserted. At least there was no one around to ask any awkward questions or revel in the fact that he had been caned. There was little doubt though, that he would need to prepare himself for the attention he would face the following day when his caning, as was customary, was announced to the entire school during assembly.
Angela Bailey was sat on one of the benches in the park waiting for Alan to come along. She lived quite close to Alan and knew that like her he always took the short cut through the park on his way home.
As she saw him approaching along the path that ran through the centre of the park, she was eager to find out what had happened, wondering whether he had told Mrs. Harwood that it was actually her who had let the air out of the tyres of Miss Danson’s rusty old Austin A40.
As Alan approached, Angie called out anxiously, “Harwood’s kept you ages, does she know it was me, did you tell her anything?”
“No, I didn’t Angie you stupid cow, in fact, thanks to you I got twelve strokes of the cane across my bare arse from Jones because Harwood accused me of letting down Danson’s tyres because I was seen near her bloody car, and then I got another six because one of the bloody cleaners had told Harwood that she saw a girl with me but wasn’t sure who it was.”
“Oh God,” responded Angie, her mouth forming a near perfect circle.
“I told Harwood I didn’t touch Danson’s tyres and told her I didn’t know anything about a girl, but she obviously didn’t believe me.”
Angie’s jaw dropped, “Oh God Alan, it was all my fault I really thought that unscrewing those cap things on the tyre valves would let the air out. Thought if I took those caps off and legged it the tyres would go down on their own, I didn’t know you had to push those pin things in as well.”
“Yeah, well next time you want to get back at a teacher for dropping you from the netball team, don’t involve me.”
Alan walked on leaving Angie on the bench.
“But Alan wait,” she called out as she grabbed her satchel and put the strap over her shoulder, before hastily scurrying after him.
“Leave me alone Angie, my arse really hurts and to be quite honest, I don’t think I ever want to speak to you again,” responded Alan curtly.
“Look I’m really sorry you got the cane and I’m really grateful you didn’t give my name. I really wish I’d gone to Harwood myself and told her the truth and that it was me that got caned, please forgive me ’cause, well, I really like you Alan and I’ll go and tell Harwood the truth in the morning. If I get my bare bum caned too then I’ll just have to live with it. Anyway, I got caned by Harwood last term so it’s no big deal really.”
Stopping in his tracks, Alan turned and faced his classmate. In truth, he really liked Angie, fancied her too, she was actually very attractive and although a little wild on occasions, was always good fun to be with.
As Alan walked on with Angie at his heels, he slowly began to soften and although the thought of this attractive girl being caned rather aroused him, his chivalrous side seemed to take over, “Look Angie, there’s no point in you getting the cane as well, I can hardly be uncaned can I? Anyway, if I hadn’t told you how to open the valves on Danson’s tyres this would never have happened.”
Knowing that he wouldn’t have been able to stay mad with Angie for long, Alan smiled at her, “It’s okay, I’m sure my bum will eventually recover and well, I like you too, fancy you I suppose, so instead of falling out over this maybe sometime we could go to the pictures or something if you like.”
Angie looked into Alan’s eyes and broke into a beaming smile displaying her perfect teeth, “Yeah, I’d really like that,” she said. “Do you really mean it?” she added.
“Yeah of course,” replied Alan, glad that if nothing else, getting caned for something he hadn’t done had at least given him the courage to ask Angie out.
Alan stood and looked at Angie, with a pretty face framed by long, dark hair which flowed over her shoulders, small pert breasts and a delightfully round bottom she really was an attractive girl and before his obsession with Mrs Harwood, Angie had often featured in his fantasies.
“You can come back to mine now if you like, we’d have the house to ourselves, my parents both work in London so won’t be home for ages,” said Angie hopeful that he would accept.
Alan smiled, “Okay,” he responded. “I don’t really want to go home until the pain eases a bit in case my mum notices. She’s like a bloody detective, never misses anything,” he added with a grin.
The two walked on until they reached Angie’s house. It wasn’t far from where Alan lived but was a completely different style and in a much more upmarket road. Angie’s parents both had good jobs in London and were obviously better off than Alan’s parents. As Angie and Alan entered the large Victorian, three storey house they both removed their shoes.
“Mum goes mad if she finds any marks on the carpet,” said Angie as they headed up the staircase to Angie’s bedroom.
As the youngest of three and with her brother away at university and her sister married and having flown the nest, Angie had the attic floor entirely to herself. After following Angie up the second staircase to the attic, Alan’s jaw dropped as they reached Angie’s bedroom, “Wow,” he said. “This is amazing, it’s ten times the size of my bedroom and you’ve even got your own shower and sink and a double bed.”
Angie grinned, “The shower’s only just been done, think my parents got fed up with me hogging the bathroom. Actually, the double bed is really for when we have guests, I have to move to a different room when that happens.”
As Angie slipped her satchel from her shoulder and placed it on the floor, Alan noticed that the pink, daisy shaped flower on the flap of the satchel was the same as the flowery wallpaper in Angie’s room, “You’ve copied that from your wallpaper,” said Alan pointing towards the satchel.
Angie laughed, “Yeah, well spotted, I painted it on, quite like daisies.”
“Maybe I should decorate my briefcase,” responded Alan as he put it down next to the satchel. “Not really worth it now though, with only one more term after this one before we leave.”
Angie stepped forward and stood in front of Alan, “You can kiss me if you like,” she said pouting her lips in invitation. Alan wasted little time in placing his arms around Angie, he had certainly put this delightful girl through some bizarre ordeals in his fantasies, but as he tasted the delicious flavour of her mouth, he knew that the reality of their intimacy would far outweigh the secret fantasies she’d featured in.
As they passionately kissed, Angie’s hands were drawn towards Alan’s bottom and as she clasped his tender cheeks in her hands, he let out a whimper.
“Sorry,” said Angie. “I almost forgot about you getting the cane, let me see what it’s done to you.”
Alan undid his trousers and slipped them down just far enough to reveal the weals on the upper part of his buttocks.
“You’re not shy are you?” giggled Angie. “I have seen a bare bum before you know, let’s have a proper look.”
“No, of course I’m not shy,” responded Alan as he slowly slipped his trousers and underpants down to the top of his thighs whilst doing his best to protect some of his modesty by hanging onto enough of the front of his underpants to keep his penis and testicles covered.
“Wow,” said Angie as she cast her eyes over the extent of his wounds. “Jones certainly didn’t hold back did he, you’ve got some pretty amazing welts?”
“It was bloody Harwood really, she told him what to do, Jones is usually okay but Harwood told him how hard to whack me and even what part of my bum to aim at. Anyway, I’m sure she actually enjoyed watching me being caned.”
Angie reached forward and began to gently stroke Alan’s buttocks. “You’ve got a really lovely bum Alan, I bet Harwood really did get off seeing a good-looking lad like you being caned. Reckon she might be bi though, ‘cause she always seems to turn up in the girls’ cloakroom when we’re in the shower, couldn’t take her eyes off Louise Kershaw last week when she was showering after cross country and I reckon she really enjoyed it when she caned my bare bum last term.”
As Angie continued to caress Alan’s buttocks the thought of Angie being caned on her bare bottom by Mrs Harwood was enough to cause a stirring between his legs. Despite his earlier thinking that he might never be able to masturbate about the headmistress or anyone else ever again, he now had little doubt that Angie being caned by Mrs Harwood would doubtless feature in his future fantasies.
“God you’re going to be sore for ages, your bum feels quite warm,” said Maggie as she took her hand away from Alan’s bottom, allowing her eyes to scan the vivid lines that embossed his cheeks.
“I think there’s a jar of cold cream in the bathroom downstairs, I reckon that would help a bit.”
With that, Angie headed out of her bedroom and as her footsteps could be heard heading down the stairs, Alan quickly stood in front of her dressing-table mirror and craned himself around to get a view of his bottom. Studying his reflection from an awkward angle though, didn’t give him the clearest of views, but he could see enough to tell that the strokes which had landed on the lower part of his buttocks had blended into one rectangular mass of red and purple and that two parallel weals about an inch apart, were displayed higher on his buttocks.
Angie returned from the bathroom a short while later clutching a large folded towel and the jar of cream she had gone in search of. Spreading the towel out on her bed she instructed Alan to take off his trousers and underpants and lay face down on the bed. Despite having to come to terms with the humiliation of being caned, there was something that Alan could not deny was totally arousing about having his well-caned bottom tended by this attractive girl. Any thoughts on protecting his modesty had now completely evaporated as he delighted in the fact that Angie’s gaze had been momentarily directed to his male parts as his underpants went south.
With Alan face down on the bed, Angie dipped her fingers into the jar and placed a thick dollop of cream onto the centre of each buttock, its coolness providing an almost instant soothing effect to his skin. As Angie delicately worked the cream into him, Alan began to writhe to her touch, occasionally wincing as her fingers worked against the swollen ridges that traversed his cheeks.
“Oh, that feels so good Angie,” groaned Alan. “Thank you,” he added as he became conscious that his cock was beginning to swell.
“Tell me if I’m hurting you,” said Angie.
“It’s fine, the welts from the cane are really tender but it’s actually quite nice when you touch them even though it does hurt a bit.”
“Kinky!” responded Angie with a giggle. “When I got caned last term, I had bruises on my bum for ages, quite liked pressing them when no one was around, ‘spose that makes me kinky too.”
Alan’s cock grew ever harder at Angie’s admission and with every movement causing the tip of his swollen cock to brush against the rough surface of the towel beneath him, he knew that he would be unable to conceal his arousal for long.
Angie leaned forward and kissed the centre of each of Alan’s buttocks, “There you go, all rubbed in,” she said perkily. “I quite enjoyed doing that, perhaps you should get caned more often,” she added with another giggle as she slowly slipped her hand between Alan’s thighs, gently brushing against his balls before wrapping her fingers around his rigid penis.
“I knew you were hard,” she chuckled. “Go on, roll on your back and let’s have some fun with your cock,” added Angie gleefully.
Alan rolled over as Angie wiped the cream from her hands on the corner of the towel, smiling at the sight of his swollen cock pointing almost directly to the ceiling. Hastily she began to set about removing her school uniform, first taking off her blouse and then removing her skirt and regulation navy-blue knickers.
“Better not get any of that cream on my uniform, my mum would go crazy if I asked her to wash it before tomorrow and I definitely wouldn’t want to explain how I ended up with cold cream on it!”
Soon, Angie stood naked save for her white knee length socks as Alan looked her up and down, delighting in the view of the thick, dark bush between her legs and as she pirouetted for his scrutiny, the sight of her beautifully round bottom, every bit as perfect as he had imagined from the way it moulded her grey, pleated school skirt so admirably.
“You’re really lovely Angie, I think you’re totally gorgeous,” he said.
Angie smiled and although her breasts were small, they were firm and hung well unaided. As she moved towards him, Alan reached up and placed his hands on them, squeezing each breast gently as his thumbs caressed her nipples.
“I always thought you didn’t fancy me,” she said. “A good-looking lad like you could have any girl he wanted so I didn’t think you’d be interested in me.”
Alan screwed his face up, “I’ve fancied you for ages Angie, thought you preferred Simon Palmer to me, you’re always hanging around with him.”
“God no,” responded Angie. “He’s okay as a friend but I really don’t fancy him,” she added.
Angie climbed onto the bed and once more wrapped her fingers around Alan’s penis, slowly working him with her hand as he soon began to writhe to her touch.
As Alan guided her to kneel astride his head, Angie continued to work him with her hand before bearing down and taking his cock deep in her mouth, sucking him energetically.
Delighting in the feel of Angie’s course, pubic bush against his face as he nuzzled against her vagina, Alan absorbed the aroma as her juice began to flow. As he nibbled her labia and penetrated her simmering chasm with his tongue, Angie’s mouth continued to offer a warm and stimulating haven for his swollen cock as she sucked him ever more vigorously.
With his hands on Angie’s delightful, firm young buttocks, Alan eased them apart as he relished the view of the neatly puckered anal ring of that most private of orifices. Before his recent obsession with Mrs Harwood, his fantasies had so often featured Angie’s anus, erotically imaging sliding his hardened member through the tightness of her sphincter as she groaned to the intrusion but did not complain.
With that very anus presented to him for real, Alan knew that if he was ever to sample the full charms of that hole, it would not be today. Gripping Angie’s firm, young buttocks and kneading them wildly, he felt compelled to offer his tongue to that most private orifice, working his tongue up and down her cleft as he enjoyed the flavour of this delicious young creature, spurring her on to suck him ever harder and frantically work the root of his cock with her fingers. Suddenly and inevitably though, Alan reached journey’s end as he felt himself release into Angie’s mouth.
>>>>>>>>>>>>>>>>>>
The following morning, Angie arrived at school early. She had been dropped off by her parents on their way to the railway station to travel to London as they did every weekday morning. Angie had agreed with Alan that despite their new found intimacy, walking to school together or being seen together too soon after the incident involving Miss Danson’s tyres, was a risk too far. Angie had though, invited Alan to go to her house after school, when they would doubtless make up for lost time.
As Angie stood in the playground her tummy began to revolve as she saw Mrs Harwood heading with purpose towards her.
“I want you in my study now Bailey, so get yourself moving,” growled the Headmistress.
Standing in front of the Headmistress’s desk, Angie stood nervously as Mrs Harwood began her spiel.
“Mrs Philpott, the cleaner has just spotted the pink flower on your satchel from the window and tells me that she now realises that the girl she saw with Alan Matthews yesterday after school around the time Miss Danson’s tyres were let down, was you Bailey.”
Angie took a deep breath, “I think she is mistaken Mrs Harwood,” pleaded Angie nervously.
The Headmistress stood up straight and placed her hands firmly on her desk, “I want the truth Bailey. If you lie to me, I will find out and you’ll only make things considerably worse for yourself.”
Angie hung her head and gnawed her lower lip, “I’m so sorry Mrs Harwood I, well, I don’t know how to tell you this, but it was me who let down the tyres not Alan, he had nothing to do with it, just happened to be passing. I know I shouldn’t have done it, but I was annoyed when Miss Danson dropped me from the netball team for the match against St Peters just because I missed one of the after-school practice sessions.”
Angie had said this quickly and having done so puffed out her cheeks and widened her eyes with a sense of relief that she had got this over with, regardless of the consequences.
“I see, but this creates a problem for us both Bailey,” said Mrs Harwood looking somewhat perplexed.
“As you probably don’t yet realise Bailey, after school yesterday, Alan Matthews received eighteen strokes of the cane in the belief that it was he who let down Miss Danson’s tyres.”
“Oh God,” responded Angie trying her best to sound shocked.
“Admittedly six of the strokes his own fault for not conveying your name,” continued the Headmistress, ”But if you’d had the decency to admit your part in this senseless act of vandalism or preferably not committed the act in the first place, the boy would have been spared the pain and humiliation of having his bare buttocks caned at my instruction by Mr Jones. I now have the embarrassing task of apologising to Matthews for my error of judgement.”
Angie did her best to continue the impression that she knew nothing about Alan’s caning. She could hardly divulge to Mrs Harwood that she had massaged cold cream into Alan’s bottom in her bedroom and had sex with him afterwards!
“Oh God, I’m so sorry Mrs Harwood, I know I should have come to you yesterday and admitted what I’d done when I found out that Alan had been sent to the study, but I never imagined he was going to be caned.”
As the Headmistress stepped away from her desk and opened the door to her secretary’s office, Angie had little doubt regarding her fate. “Mrs Jenkins please come through, I regret I need you to act as witness to a caning.”
Moments later, Angie found herself bent over the desk with a senior crook handle cane lying next to her as the Headmistress raised her skirt and tucked it into its own waistband before peeling her navy-blue knickers down to her thighs.
With the cane clutched firmly in her hand, Mrs Harwood offered it to the centre of Angie’s pouting bottom, tapping it against her as she weighed up the target on offer, “You obviously haven’t learnt from the caning you received last term, have you Bailey?”
From her bent over position, Angie slowly shook her head, “No Mrs Harwood, it seems like I haven’t.”
“Twelve strokes Bailey and count yourself lucky that I’m not giving you eighteen after what happened to Matthews yesterday.”
Just as the Headmistress prepared to draw the cane back for the first stroke there was a firm knock at the study door.
“Oh please see who that is and tell them they’ll have to wait Mrs Jenkins,” said the Headmistress, angrily.
The rotund figure of Mrs Jenkins headed across the room to the door, opening it just a fraction and closing it again a moment later. “It was Alan Matthews, Mrs Harwood, says he has a letter you asked to see so I’ve told him to sit and wait on the bench in the corridor.”
“Thank you, Mrs Jenkins,” responded the Headmistress as she once more began to tap the cane against Angie’s bottom.
“Twelve strokes, Bailey count them for me please,” snarled the Headmistress.
Angie nodded, “Yes Mrs Harwood,” she replied meekly.
Without delay Mrs Harwood raised the cane and brought it down firmly across the centre of Angie’s bottom. “Ow,” cried Angie, before responding with, “One Miss.”
As the cane struck her buttocks for the second stroke, Angie jolted back and drew breath through her teeth before responding “Two Miss, Oh, that really stung Miss.”
As the third stroke landed firmly across the lower portion of her bottom it seemed that Angie was beginning to process the true agony of a caning as she yelled. “AAH, AHH! Oh Miss, it hurts so much….....Three Miss.”
With three, painful red stripes now decorating her delightful, young bottom, Angie contorted her bottom as the Headmistress wasted little time in offering the cane to the point where buttock and thigh merge before drawing it back for the next stroke. The sound of the cane cutting through the air as it heralded the fourth stoke caused Angie to flinch and as a line was painted a fraction lower than intended. Angie shrieked, “YEEOW, AAH! AAH! OW, WOW! That was the top of my legs Miss, OW-OW….Four Miss.”
Mrs Harwood lowered the cane and ran her hand across the swollen ridge which immediately blossomed at the top of Angie’s thighs. “You need to keep still young lady, if you wriggle about it will only make it worse for you.”
Sat on the bench in the corridor, it hadn’t taken Alan long to realise that it was Angie who was being caned. The study door was solid enough to muffle much of the sound, but as the caning progressed and Angie became more vocal, Alan was left in no doubt that it was Angie who was currently at the Headmistress’s mercy. With the agony of his own caning still fresh in his mind, he knew that Angie must be suffering, but to his inner embarrassment, he had little control over the swelling that was building in his trousers.
Two more strokes swiftly followed and painted stripes across the higher part of Angie’s bottom, “OW-AH-OW…… Five Miss” she cried rocking from foot to foot, “OH….S-Six Miss,” she squealed as the halfway point was reached.
Drawing the cane back once more, the Headmistress brought it down firmly across the centre of Angie’s bottom causing her to arch her back in an effort to quell the agony of the stroke. “EE-OW! ………Seven Miss,” she shrieked, but almost before the echo of her cries had faded from the room the next stroke landed high on her bottom as she tightened her grip on the edge of the desk. “OUCH! OUCH!..OUCH!.. Oh, that really, really hurt. Eight Miss,” she cried.
Glancing along the corridor to make sure he was alone, Alan placed his hand against the bulge in his trousers and began to gently work himself. The thought of the magnificent bottom he had been privileged to explore just a few hours earlier now receiving a severe caning, was arousing beyond control.
Raising the cane again the Headmistress delivered another hard stroke to the lower part of Angie’s bottom. “OW..OW..OW” squealed Angie. “Nine Miss.”
With three further strokes remaining, Mrs Harwood wasted little time, swiftly dispatching the next two in quick succession.
“Ten Miss,” she cried.
“Eleven Miss. OW-OW-OW,” she shrieked. “
“One more to go Bailey,” announced the Headmistress as she offered the cane to Angie’s bottom for the final stroke.
Angie screwed up her face as she awaited this final challenge and as the cane landed low down on her buttocks the sound of its impact echoed around the study like a pistol shot as Angie contorted her bottom wildly and thrust her head back.
“YEEOW. OW, OW, OW, AH, AH, OW…..Twelve Miss,” she wailed.
As Mrs Harwood stepped back and lowered the cane, she gave Angie permission rub her bottom.
Frantically, Angie set about tending her wounds, knowing that Alan was waiting on the bench outside the study and had probably heard everything.
“Pull up your knickers and tidy your skirt Bailey,” ordered the Headmistress with a satisfied expression as she quickly scrutinised the well-marked bottom before her. “During morning break you will write a letter of apology to Miss Danson for what you did to her car and show it to me.”
“Yes Mrs Harwood,” responded Angie wincing as she carefully guided her knickers back into place over her throbbing buttocks.
“I don’t ever want to see you in this study again for punishment, is that clear Bailey? Now go and join your class.”
“You won’t Mrs Harwood, I’ll never do anything like that again I promise,” replied Angie as she turned toward the door.
As Angie left the study and closed the door behind her, she came face to face with Alan in the corridor.
“Oh Angie, you didn’t go and tell her did you?” whispered Alan, thankful that his cock had now wilted somewhat.
“No, bloody Philpott the cleaner recognised my satchel ‘cause of the bloody flower on it,” whispered Angie in return.
“Better go, see you later,” added Angie before walking slowly and stiffly down the corridor with her hands rubbing her buttocks through her skirt as she went.
Glancing at his briefcase and smiling at the thought of the pack of condoms he had bought on the way to school and squirreled into the lining, Alan quickly returned his gaze to Angie as she continued along the corridor, watching until she finally disappeared from view and imagining the pleasure that beautiful well-caned bottom would afford later that day.
As Alan’s cock began to once more stir in his trousers the study door slowly opened and Mrs Harwood stepped into the corridor, “Alan,” she said with a gentle smile. “I’m so sorry to have kept you waiting, please come in.”
The End
Adding to this painful ordeal though, was the fact that Mrs Harwood the Headmistress had remained in the study for the duration of his caning. Although it was customary for two members of staff to be present whenever corporal punishment was being administered, the fact that one of them was not only female, but the Headmistress herself, was a point beyond humiliation for Alan.
Although in her forties, Mrs Harwood was an extremely attractive woman. Ever since Alan had gone on a fishing trip with classmate and friend, Jonathan Elliot along with Jonathan’s father, Alan had found himself entering into what was perhaps, forbidden territory for an eighteen-year-old lad, and had begun including the headmistress in many of his masturbatory fantasies.
“God, she’s got an amazing arse that headmistress of yours, pretty decent tits too, gorgeous woman, gorgeous woman,” Jonathan’s father had said as they sat patiently in the small, fibreglass dingy a mile or so from shore as they waited for the fish to bite.
“Certainly wouldn’t kick her out of bed, she’s a bit different to the headmistress I had when I was at school,” Mr Elliot had added with a grin.
With a slightly embarrassed look on his face, Jonathan had attempted to make light of his father’s comments, “Dad used to be in the merchant navy, spent months at sea without seeing any women so he gets a bit overexcited when he sees a woman he fancies.”
Mr Elliot pursed his lips and nodded his head as if confirming that what Jonathan was saying was actually true.
Alan had never really given any thought to Mrs Harwood’s personal attributes before that time. Miss Harrison the English teacher had certainly caught his attention, but she was in her early twenties and wore short skirts that displayed totally gorgeous thighs and every so often, as she leaned forward, she offered a fleeting glimpse of the lower part of her shapely, panty clad bottom. Mrs Harwood though, well she was the Headmistress, she just wasn’t someone an eighteen- year- old should be aroused by even if she was a good-looking woman.
The comments made by Jonathan’s father had though, somehow got Alan thinking. Mrs. Harwood was indeed an appealing woman and despite being similar in age to his mother, the ‘arse’ and ‘tits’ referred to by Jonathan’s father had suddenly become worthy of further consideration. Almost before he knew it, Alan found himself crossing the finishing line on many an occasion as he masturbated in the privacy of his bedroom to thoughts of Mrs. Harwood.
With a penchant for the female bottom and despite having never experienced anal sex, one of Alan’s most recurring fantasies was having Mrs. Harwood bent over the very desk that he now found himself bent over, and with her skirt raised and her knickers around her ankles, spanking and caning her ‘amazing’ arse before sliding his swollen cock deep into her beckoning anus as he kneaded her tender buttocks with his hands. At this moment in time though, Alan was fully convinced that he would never masturbate to thoughts of the headmistress ever again, in fact, his humiliation was such he may never masturbate to thoughts of anyone ever again!
As Alan once more felt the cane tap against his buttocks, he screwed up his face in anticipation of the agony that would soon follow and as Mr. Jones raised the cane high above his shoulder and brought it down with blistering force across Alan’s cheeks, it was all he could do to stay in position as he felt as though his buttocks were about to explode.
“AH, AH, OW...WOW, OW,” yelled the handsome, fair-haired teenager. “Thirteen Sir,” he added.
The next stroke soon followed and was similar in force, landing just a fraction lower on his buttocks.
‘OH, OH, OW, AH...... OUCH,’ he cried. “f******n Sir.”
With two more strokes swiftly applied, Alan contorted wildly, the searing bite of the cane making him wonder whether his bottom would ever recover from this terrible ordeal.
“Two more strokes Matthews,” announced the voice of the man from Harlech as he swished the cane through the air in preparation of the finale, causing Alan to flinch at the sound.
Out of the corner of his eye, Alan could see the headmistress unfold her arms and step up behind him to scrutinise his bottom. “I think Mr Jones, you need to aim a little higher on the boy’s buttocks for the remaining two strokes,” she said in her refined tones whilst pressing a fingertip against the part of his bottom that had yet to be challenged.
Displaying his bare backside to the Headmistress as he was being caned was humiliating in itself, but being referred to as a boy by a woman he’d included in so many of his recent masturbatory fantasies, was beyond humiliating.
Mrs Harwood continued to keep her fingertip pressed against the upper part of Alan’s buttocks, “The lower part of his bottom is already very marked and it’s best not to risk splitting any of those weals wide open, so place the remaining strokes about here and make them good and hard,” she added as she drew an imaginary line with her finger across the top of Alan’s bottom.
“Of course, Mrs Harwood, responded the Welshman as he adjusted his aim and offered the cane to the higher part of Alan’s cheeks.
Raising the cane for the penultimate stroke, Mr Jones thrust it downwards with all the force he could muster. As the cane cracked mercilessly against the tender flesh of Alan’s upper buttocks, another vivid red stripe was added to the colourful landscape he already presented. Grasping his buttocks with both hands Alan once more cried out, “EEEOWCH, OW-OW-OW....OH, OH……………S, S, s*******n………. Sir.”
“Back in position Matthews or you’ll get extra strokes,” snarled Mrs Harwood.
Without delay Alan returned his hands to the far side of the desk and firmly gripped its edge, the thought running through his mind that perhaps the headmistress was actually getting some sort of perverse pleasure out of watching his ordeal.
As Mr Jones addressed Alan’s bottom for the last of his eighteen strokes, the Headmistress once more intervened, “Grab your buttocks again Matthews and you definitely will get extra strokes, you’ll be given permission to rub yourself when I decide, is that clear?”
“Yes Mrs Harwood,” responded Alan. “Totally clear.”
After tapping the cane against the top of Alan’s buttocks, Mr. Jones once more raised it high above his shoulder and unleashed a stroke that nearly lifted Alan off his feet.
As the sound of the impact resonated around the study, the agony of the stroke felt to Alan like he’d had a red-hot poker laid across his cheeks.
“OW, WOW, WOW, OW,” AH, AH, OH, AH…..OH,” he yelled as he tightened his grip on the edge of the desk to avoid his hands straying towards his throbbing buttocks and running the risk of extra strokes. “Eighteen……S.. Sir,” he eventually added as he fought to recover just a little of his composure.
“Okay Matthews you may rub yourself now,” said Mrs Harwood. “When you’re ready, pull up your underpants and trousers and go home and don’t forget that first thing tomorrow morning you will come to this study and show me the letter of apology you will write this evening to Miss Danson for what you did to her car.”
“No, I won’t forget Mrs. Harwood,” responded Alan meekly as he frantically rubbed his throbbing bottom and resisted further pleading his innocence for fear of receiving more cane strokes.
Walking stiffly across the playground, Alan headed towards the school gates, grateful for the fact that he had been kept behind long enough after school for the playground to now be deserted. At least there was no one around to ask any awkward questions or revel in the fact that he had been caned. There was little doubt though, that he would need to prepare himself for the attention he would face the following day when his caning, as was customary, was announced to the entire school during assembly.
Angela Bailey was sat on one of the benches in the park waiting for Alan to come along. She lived quite close to Alan and knew that like her he always took the short cut through the park on his way home.
As she saw him approaching along the path that ran through the centre of the park, she was eager to find out what had happened, wondering whether he had told Mrs. Harwood that it was actually her who had let the air out of the tyres of Miss Danson’s rusty old Austin A40.
As Alan approached, Angie called out anxiously, “Harwood’s kept you ages, does she know it was me, did you tell her anything?”
“No, I didn’t Angie you stupid cow, in fact, thanks to you I got twelve strokes of the cane across my bare arse from Jones because Harwood accused me of letting down Danson’s tyres because I was seen near her bloody car, and then I got another six because one of the bloody cleaners had told Harwood that she saw a girl with me but wasn’t sure who it was.”
“Oh God,” responded Angie, her mouth forming a near perfect circle.
“I told Harwood I didn’t touch Danson’s tyres and told her I didn’t know anything about a girl, but she obviously didn’t believe me.”
Angie’s jaw dropped, “Oh God Alan, it was all my fault I really thought that unscrewing those cap things on the tyre valves would let the air out. Thought if I took those caps off and legged it the tyres would go down on their own, I didn’t know you had to push those pin things in as well.”
“Yeah, well next time you want to get back at a teacher for dropping you from the netball team, don’t involve me.”
Alan walked on leaving Angie on the bench.
“But Alan wait,” she called out as she grabbed her satchel and put the strap over her shoulder, before hastily scurrying after him.
“Leave me alone Angie, my arse really hurts and to be quite honest, I don’t think I ever want to speak to you again,” responded Alan curtly.
“Look I’m really sorry you got the cane and I’m really grateful you didn’t give my name. I really wish I’d gone to Harwood myself and told her the truth and that it was me that got caned, please forgive me ’cause, well, I really like you Alan and I’ll go and tell Harwood the truth in the morning. If I get my bare bum caned too then I’ll just have to live with it. Anyway, I got caned by Harwood last term so it’s no big deal really.”
Stopping in his tracks, Alan turned and faced his classmate. In truth, he really liked Angie, fancied her too, she was actually very attractive and although a little wild on occasions, was always good fun to be with.
As Alan walked on with Angie at his heels, he slowly began to soften and although the thought of this attractive girl being caned rather aroused him, his chivalrous side seemed to take over, “Look Angie, there’s no point in you getting the cane as well, I can hardly be uncaned can I? Anyway, if I hadn’t told you how to open the valves on Danson’s tyres this would never have happened.”
Knowing that he wouldn’t have been able to stay mad with Angie for long, Alan smiled at her, “It’s okay, I’m sure my bum will eventually recover and well, I like you too, fancy you I suppose, so instead of falling out over this maybe sometime we could go to the pictures or something if you like.”
Angie looked into Alan’s eyes and broke into a beaming smile displaying her perfect teeth, “Yeah, I’d really like that,” she said. “Do you really mean it?” she added.
“Yeah of course,” replied Alan, glad that if nothing else, getting caned for something he hadn’t done had at least given him the courage to ask Angie out.
Alan stood and looked at Angie, with a pretty face framed by long, dark hair which flowed over her shoulders, small pert breasts and a delightfully round bottom she really was an attractive girl and before his obsession with Mrs Harwood, Angie had often featured in his fantasies.
“You can come back to mine now if you like, we’d have the house to ourselves, my parents both work in London so won’t be home for ages,” said Angie hopeful that he would accept.
Alan smiled, “Okay,” he responded. “I don’t really want to go home until the pain eases a bit in case my mum notices. She’s like a bloody detective, never misses anything,” he added with a grin.
The two walked on until they reached Angie’s house. It wasn’t far from where Alan lived but was a completely different style and in a much more upmarket road. Angie’s parents both had good jobs in London and were obviously better off than Alan’s parents. As Angie and Alan entered the large Victorian, three storey house they both removed their shoes.
“Mum goes mad if she finds any marks on the carpet,” said Angie as they headed up the staircase to Angie’s bedroom.
As the youngest of three and with her brother away at university and her sister married and having flown the nest, Angie had the attic floor entirely to herself. After following Angie up the second staircase to the attic, Alan’s jaw dropped as they reached Angie’s bedroom, “Wow,” he said. “This is amazing, it’s ten times the size of my bedroom and you’ve even got your own shower and sink and a double bed.”
Angie grinned, “The shower’s only just been done, think my parents got fed up with me hogging the bathroom. Actually, the double bed is really for when we have guests, I have to move to a different room when that happens.”
As Angie slipped her satchel from her shoulder and placed it on the floor, Alan noticed that the pink, daisy shaped flower on the flap of the satchel was the same as the flowery wallpaper in Angie’s room, “You’ve copied that from your wallpaper,” said Alan pointing towards the satchel.
Angie laughed, “Yeah, well spotted, I painted it on, quite like daisies.”
“Maybe I should decorate my briefcase,” responded Alan as he put it down next to the satchel. “Not really worth it now though, with only one more term after this one before we leave.”
Angie stepped forward and stood in front of Alan, “You can kiss me if you like,” she said pouting her lips in invitation. Alan wasted little time in placing his arms around Angie, he had certainly put this delightful girl through some bizarre ordeals in his fantasies, but as he tasted the delicious flavour of her mouth, he knew that the reality of their intimacy would far outweigh the secret fantasies she’d featured in.
As they passionately kissed, Angie’s hands were drawn towards Alan’s bottom and as she clasped his tender cheeks in her hands, he let out a whimper.
“Sorry,” said Angie. “I almost forgot about you getting the cane, let me see what it’s done to you.”
Alan undid his trousers and slipped them down just far enough to reveal the weals on the upper part of his buttocks.
“You’re not shy are you?” giggled Angie. “I have seen a bare bum before you know, let’s have a proper look.”
“No, of course I’m not shy,” responded Alan as he slowly slipped his trousers and underpants down to the top of his thighs whilst doing his best to protect some of his modesty by hanging onto enough of the front of his underpants to keep his penis and testicles covered.
“Wow,” said Angie as she cast her eyes over the extent of his wounds. “Jones certainly didn’t hold back did he, you’ve got some pretty amazing welts?”
“It was bloody Harwood really, she told him what to do, Jones is usually okay but Harwood told him how hard to whack me and even what part of my bum to aim at. Anyway, I’m sure she actually enjoyed watching me being caned.”
Angie reached forward and began to gently stroke Alan’s buttocks. “You’ve got a really lovely bum Alan, I bet Harwood really did get off seeing a good-looking lad like you being caned. Reckon she might be bi though, ‘cause she always seems to turn up in the girls’ cloakroom when we’re in the shower, couldn’t take her eyes off Louise Kershaw last week when she was showering after cross country and I reckon she really enjoyed it when she caned my bare bum last term.”
As Angie continued to caress Alan’s buttocks the thought of Angie being caned on her bare bottom by Mrs Harwood was enough to cause a stirring between his legs. Despite his earlier thinking that he might never be able to masturbate about the headmistress or anyone else ever again, he now had little doubt that Angie being caned by Mrs Harwood would doubtless feature in his future fantasies.
“God you’re going to be sore for ages, your bum feels quite warm,” said Maggie as she took her hand away from Alan’s bottom, allowing her eyes to scan the vivid lines that embossed his cheeks.
“I think there’s a jar of cold cream in the bathroom downstairs, I reckon that would help a bit.”
With that, Angie headed out of her bedroom and as her footsteps could be heard heading down the stairs, Alan quickly stood in front of her dressing-table mirror and craned himself around to get a view of his bottom. Studying his reflection from an awkward angle though, didn’t give him the clearest of views, but he could see enough to tell that the strokes which had landed on the lower part of his buttocks had blended into one rectangular mass of red and purple and that two parallel weals about an inch apart, were displayed higher on his buttocks.
Angie returned from the bathroom a short while later clutching a large folded towel and the jar of cream she had gone in search of. Spreading the towel out on her bed she instructed Alan to take off his trousers and underpants and lay face down on the bed. Despite having to come to terms with the humiliation of being caned, there was something that Alan could not deny was totally arousing about having his well-caned bottom tended by this attractive girl. Any thoughts on protecting his modesty had now completely evaporated as he delighted in the fact that Angie’s gaze had been momentarily directed to his male parts as his underpants went south.
With Alan face down on the bed, Angie dipped her fingers into the jar and placed a thick dollop of cream onto the centre of each buttock, its coolness providing an almost instant soothing effect to his skin. As Angie delicately worked the cream into him, Alan began to writhe to her touch, occasionally wincing as her fingers worked against the swollen ridges that traversed his cheeks.
“Oh, that feels so good Angie,” groaned Alan. “Thank you,” he added as he became conscious that his cock was beginning to swell.
“Tell me if I’m hurting you,” said Angie.
“It’s fine, the welts from the cane are really tender but it’s actually quite nice when you touch them even though it does hurt a bit.”
“Kinky!” responded Angie with a giggle. “When I got caned last term, I had bruises on my bum for ages, quite liked pressing them when no one was around, ‘spose that makes me kinky too.”
Alan’s cock grew ever harder at Angie’s admission and with every movement causing the tip of his swollen cock to brush against the rough surface of the towel beneath him, he knew that he would be unable to conceal his arousal for long.
Angie leaned forward and kissed the centre of each of Alan’s buttocks, “There you go, all rubbed in,” she said perkily. “I quite enjoyed doing that, perhaps you should get caned more often,” she added with another giggle as she slowly slipped her hand between Alan’s thighs, gently brushing against his balls before wrapping her fingers around his rigid penis.
“I knew you were hard,” she chuckled. “Go on, roll on your back and let’s have some fun with your cock,” added Angie gleefully.
Alan rolled over as Angie wiped the cream from her hands on the corner of the towel, smiling at the sight of his swollen cock pointing almost directly to the ceiling. Hastily she began to set about removing her school uniform, first taking off her blouse and then removing her skirt and regulation navy-blue knickers.
“Better not get any of that cream on my uniform, my mum would go crazy if I asked her to wash it before tomorrow and I definitely wouldn’t want to explain how I ended up with cold cream on it!”
Soon, Angie stood naked save for her white knee length socks as Alan looked her up and down, delighting in the view of the thick, dark bush between her legs and as she pirouetted for his scrutiny, the sight of her beautifully round bottom, every bit as perfect as he had imagined from the way it moulded her grey, pleated school skirt so admirably.
“You’re really lovely Angie, I think you’re totally gorgeous,” he said.
Angie smiled and although her breasts were small, they were firm and hung well unaided. As she moved towards him, Alan reached up and placed his hands on them, squeezing each breast gently as his thumbs caressed her nipples.
“I always thought you didn’t fancy me,” she said. “A good-looking lad like you could have any girl he wanted so I didn’t think you’d be interested in me.”
Alan screwed his face up, “I’ve fancied you for ages Angie, thought you preferred Simon Palmer to me, you’re always hanging around with him.”
“God no,” responded Angie. “He’s okay as a friend but I really don’t fancy him,” she added.
Angie climbed onto the bed and once more wrapped her fingers around Alan’s penis, slowly working him with her hand as he soon began to writhe to her touch.
As Alan guided her to kneel astride his head, Angie continued to work him with her hand before bearing down and taking his cock deep in her mouth, sucking him energetically.
Delighting in the feel of Angie’s course, pubic bush against his face as he nuzzled against her vagina, Alan absorbed the aroma as her juice began to flow. As he nibbled her labia and penetrated her simmering chasm with his tongue, Angie’s mouth continued to offer a warm and stimulating haven for his swollen cock as she sucked him ever more vigorously.
With his hands on Angie’s delightful, firm young buttocks, Alan eased them apart as he relished the view of the neatly puckered anal ring of that most private of orifices. Before his recent obsession with Mrs Harwood, his fantasies had so often featured Angie’s anus, erotically imaging sliding his hardened member through the tightness of her sphincter as she groaned to the intrusion but did not complain.
With that very anus presented to him for real, Alan knew that if he was ever to sample the full charms of that hole, it would not be today. Gripping Angie’s firm, young buttocks and kneading them wildly, he felt compelled to offer his tongue to that most private orifice, working his tongue up and down her cleft as he enjoyed the flavour of this delicious young creature, spurring her on to suck him ever harder and frantically work the root of his cock with her fingers. Suddenly and inevitably though, Alan reached journey’s end as he felt himself release into Angie’s mouth.
>>>>>>>>>>>>>>>>>>
The following morning, Angie arrived at school early. She had been dropped off by her parents on their way to the railway station to travel to London as they did every weekday morning. Angie had agreed with Alan that despite their new found intimacy, walking to school together or being seen together too soon after the incident involving Miss Danson’s tyres, was a risk too far. Angie had though, invited Alan to go to her house after school, when they would doubtless make up for lost time.
As Angie stood in the playground her tummy began to revolve as she saw Mrs Harwood heading with purpose towards her.
“I want you in my study now Bailey, so get yourself moving,” growled the Headmistress.
Standing in front of the Headmistress’s desk, Angie stood nervously as Mrs Harwood began her spiel.
“Mrs Philpott, the cleaner has just spotted the pink flower on your satchel from the window and tells me that she now realises that the girl she saw with Alan Matthews yesterday after school around the time Miss Danson’s tyres were let down, was you Bailey.”
Angie took a deep breath, “I think she is mistaken Mrs Harwood,” pleaded Angie nervously.
The Headmistress stood up straight and placed her hands firmly on her desk, “I want the truth Bailey. If you lie to me, I will find out and you’ll only make things considerably worse for yourself.”
Angie hung her head and gnawed her lower lip, “I’m so sorry Mrs Harwood I, well, I don’t know how to tell you this, but it was me who let down the tyres not Alan, he had nothing to do with it, just happened to be passing. I know I shouldn’t have done it, but I was annoyed when Miss Danson dropped me from the netball team for the match against St Peters just because I missed one of the after-school practice sessions.”
Angie had said this quickly and having done so puffed out her cheeks and widened her eyes with a sense of relief that she had got this over with, regardless of the consequences.
“I see, but this creates a problem for us both Bailey,” said Mrs Harwood looking somewhat perplexed.
“As you probably don’t yet realise Bailey, after school yesterday, Alan Matthews received eighteen strokes of the cane in the belief that it was he who let down Miss Danson’s tyres.”
“Oh God,” responded Angie trying her best to sound shocked.
“Admittedly six of the strokes his own fault for not conveying your name,” continued the Headmistress, ”But if you’d had the decency to admit your part in this senseless act of vandalism or preferably not committed the act in the first place, the boy would have been spared the pain and humiliation of having his bare buttocks caned at my instruction by Mr Jones. I now have the embarrassing task of apologising to Matthews for my error of judgement.”
Angie did her best to continue the impression that she knew nothing about Alan’s caning. She could hardly divulge to Mrs Harwood that she had massaged cold cream into Alan’s bottom in her bedroom and had sex with him afterwards!
“Oh God, I’m so sorry Mrs Harwood, I know I should have come to you yesterday and admitted what I’d done when I found out that Alan had been sent to the study, but I never imagined he was going to be caned.”
As the Headmistress stepped away from her desk and opened the door to her secretary’s office, Angie had little doubt regarding her fate. “Mrs Jenkins please come through, I regret I need you to act as witness to a caning.”
Moments later, Angie found herself bent over the desk with a senior crook handle cane lying next to her as the Headmistress raised her skirt and tucked it into its own waistband before peeling her navy-blue knickers down to her thighs.
With the cane clutched firmly in her hand, Mrs Harwood offered it to the centre of Angie’s pouting bottom, tapping it against her as she weighed up the target on offer, “You obviously haven’t learnt from the caning you received last term, have you Bailey?”
From her bent over position, Angie slowly shook her head, “No Mrs Harwood, it seems like I haven’t.”
“Twelve strokes Bailey and count yourself lucky that I’m not giving you eighteen after what happened to Matthews yesterday.”
Just as the Headmistress prepared to draw the cane back for the first stroke there was a firm knock at the study door.
“Oh please see who that is and tell them they’ll have to wait Mrs Jenkins,” said the Headmistress, angrily.
The rotund figure of Mrs Jenkins headed across the room to the door, opening it just a fraction and closing it again a moment later. “It was Alan Matthews, Mrs Harwood, says he has a letter you asked to see so I’ve told him to sit and wait on the bench in the corridor.”
“Thank you, Mrs Jenkins,” responded the Headmistress as she once more began to tap the cane against Angie’s bottom.
“Twelve strokes, Bailey count them for me please,” snarled the Headmistress.
Angie nodded, “Yes Mrs Harwood,” she replied meekly.
Without delay Mrs Harwood raised the cane and brought it down firmly across the centre of Angie’s bottom. “Ow,” cried Angie, before responding with, “One Miss.”
As the cane struck her buttocks for the second stroke, Angie jolted back and drew breath through her teeth before responding “Two Miss, Oh, that really stung Miss.”
As the third stroke landed firmly across the lower portion of her bottom it seemed that Angie was beginning to process the true agony of a caning as she yelled. “AAH, AHH! Oh Miss, it hurts so much….....Three Miss.”
With three, painful red stripes now decorating her delightful, young bottom, Angie contorted her bottom as the Headmistress wasted little time in offering the cane to the point where buttock and thigh merge before drawing it back for the next stroke. The sound of the cane cutting through the air as it heralded the fourth stoke caused Angie to flinch and as a line was painted a fraction lower than intended. Angie shrieked, “YEEOW, AAH! AAH! OW, WOW! That was the top of my legs Miss, OW-OW….Four Miss.”
Mrs Harwood lowered the cane and ran her hand across the swollen ridge which immediately blossomed at the top of Angie’s thighs. “You need to keep still young lady, if you wriggle about it will only make it worse for you.”
Sat on the bench in the corridor, it hadn’t taken Alan long to realise that it was Angie who was being caned. The study door was solid enough to muffle much of the sound, but as the caning progressed and Angie became more vocal, Alan was left in no doubt that it was Angie who was currently at the Headmistress’s mercy. With the agony of his own caning still fresh in his mind, he knew that Angie must be suffering, but to his inner embarrassment, he had little control over the swelling that was building in his trousers.
Two more strokes swiftly followed and painted stripes across the higher part of Angie’s bottom, “OW-AH-OW…… Five Miss” she cried rocking from foot to foot, “OH….S-Six Miss,” she squealed as the halfway point was reached.
Drawing the cane back once more, the Headmistress brought it down firmly across the centre of Angie’s bottom causing her to arch her back in an effort to quell the agony of the stroke. “EE-OW! ………Seven Miss,” she shrieked, but almost before the echo of her cries had faded from the room the next stroke landed high on her bottom as she tightened her grip on the edge of the desk. “OUCH! OUCH!..OUCH!.. Oh, that really, really hurt. Eight Miss,” she cried.
Glancing along the corridor to make sure he was alone, Alan placed his hand against the bulge in his trousers and began to gently work himself. The thought of the magnificent bottom he had been privileged to explore just a few hours earlier now receiving a severe caning, was arousing beyond control.
Raising the cane again the Headmistress delivered another hard stroke to the lower part of Angie’s bottom. “OW..OW..OW” squealed Angie. “Nine Miss.”
With three further strokes remaining, Mrs Harwood wasted little time, swiftly dispatching the next two in quick succession.
“Ten Miss,” she cried.
“Eleven Miss. OW-OW-OW,” she shrieked. “
“One more to go Bailey,” announced the Headmistress as she offered the cane to Angie’s bottom for the final stroke.
Angie screwed up her face as she awaited this final challenge and as the cane landed low down on her buttocks the sound of its impact echoed around the study like a pistol shot as Angie contorted her bottom wildly and thrust her head back.
“YEEOW. OW, OW, OW, AH, AH, OW…..Twelve Miss,” she wailed.
As Mrs Harwood stepped back and lowered the cane, she gave Angie permission rub her bottom.
Frantically, Angie set about tending her wounds, knowing that Alan was waiting on the bench outside the study and had probably heard everything.
“Pull up your knickers and tidy your skirt Bailey,” ordered the Headmistress with a satisfied expression as she quickly scrutinised the well-marked bottom before her. “During morning break you will write a letter of apology to Miss Danson for what you did to her car and show it to me.”
“Yes Mrs Harwood,” responded Angie wincing as she carefully guided her knickers back into place over her throbbing buttocks.
“I don’t ever want to see you in this study again for punishment, is that clear Bailey? Now go and join your class.”
“You won’t Mrs Harwood, I’ll never do anything like that again I promise,” replied Angie as she turned toward the door.
As Angie left the study and closed the door behind her, she came face to face with Alan in the corridor.
“Oh Angie, you didn’t go and tell her did you?” whispered Alan, thankful that his cock had now wilted somewhat.
“No, bloody Philpott the cleaner recognised my satchel ‘cause of the bloody flower on it,” whispered Angie in return.
“Better go, see you later,” added Angie before walking slowly and stiffly down the corridor with her hands rubbing her buttocks through her skirt as she went.
Glancing at his briefcase and smiling at the thought of the pack of condoms he had bought on the way to school and squirreled into the lining, Alan quickly returned his gaze to Angie as she continued along the corridor, watching until she finally disappeared from view and imagining the pleasure that beautiful well-caned bottom would afford later that day.
As Alan’s cock began to once more stir in his trousers the study door slowly opened and Mrs Harwood stepped into the corridor, “Alan,” she said with a gentle smile. “I’m so sorry to have kept you waiting, please come in.”
The End
3 года назад
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