♥ Site recommended story ♥
A hot new femdom caning story by very special guest author Barry Spockings. This story is exclusive to The Canery! All the characters are 18 or over. WARNING: ADULTS ONLY!
DELAYED RETRIBUTION by Barry Spockings
Some 5 years after leaving Grammar school I was surprised to receive a letter from my old Headmistress, Miss Gray, inviting me to a school reunion. It surprised me as I had had nothing to do with the Grammar school since leaving it and also that she knew of my new address. However my main concern was that I had left the school under a bit of a cloud and was worried that she might remember it. It was the last week of term and exams were over and as we were all looking forward to the summer holidays and perhaps thereafter studying at University, our spirits were high and as we were not being supervised some of the sixth formers’ behavior was a bit over the top. Roy Suckling, whose foolhardiness had frequently got him into trouble resulting in his reputation of being the most caned boy by the Headmistress in the school, was unfortunately seated in the next row to me and as I was about to sit down he pulled my chair away causing me to fall to the floor, painfully banging my head and making the whole class laugh. Naturally I tried to pull my chair away from him but in so doing he also fell to the floor resulting in breaking both his chair and mine!
This was a serious situation and would be interpreted as vandalism carrying serious painful consequences for the perpetrators. Suckling and I quickly exchanged our chairs for two spare ones at the back of the classroom hoping no one would notice the damage. However our hopes were dashed at the end of the final assembly on Friday when Headmistress Gray announced that the previous day there had been a serious case of vandalism in the sixth form room discovered that evening by the caretaker. ‘’The person or persons responsible are expected to report to my study immediately after this assembly and can expect some painful consequences for their reprehensible behaviour!’’
I immediately said to Suckling that we should own up as everyone in our class knew that we were both responsible. He disagreed as he said it had been his fault and that I should not be involved. ‘’I have been caned by the Headmistress many times before so it will be no big deal.’’ I was so relieved to hear this as I had never been caned before and was terrified at the prospect. So we left it at that and he left me feeling more than a little pusillanimous and, strangely, perhaps because I had never been caned before I had a paradoxical attitude towards being caned – it would be painful but there was a strangely appealing aspect about being punished by a woman. I did not see Suckling again after he visited her study but learnt later from one of his friends that he had been sent home after receiving twelve strokes of the cane on his bare bottom! I felt awful as I considered myself as much to blame as he was and should have shared his punishment. But Friday was my last day at school and I left it unpunished.
Now five years later, after university and starting a career as a science teacher, I was returning to the Grammar school for a reunion. I parked my car near the entrance and entered the school through the main entrance to find it strangely deserted. Perhaps I had got the wrong date for the reunion – then I heard footsteps behind me and turned round to find Headmistress Gray approaching me.
“Ah, Barry Spockings! I am so pleased you could make it. Please follow me to my study. “
Meekly I followed her, a still very attractive woman now in her late forties. I noticed she had maintained her slim, trim figure and was dressed in a daringly short tight skirt with black stockings and black high heels. I found it strange that she had not married, as I always considered her to be very attractive. She entered her study and I followed in as she sat behind her desk. Addressing me she began by saying that she had to apologise for misleading me.
“I am sorry but I have brought you here under false pretenses – there is no school reunion today. I am afraid instead I have brought you here for some unfinished business or as I call it delayed retribution!”
My heart skipped a beat – and I suddenly suspected that I possibly faced the prospect of a beating!
“You may recollect that on your last day at this school I had to give Roy Suckling a severe caning for an act of vandalism. Do you remember?”
“Yes Miss Gray.”
“Well at the time I suspected that he was not the sole perpetrator despite his denials. However a few weeks ago by chance I met Janet Priday, a classmate of yours and Roy Sucklings, at a local coffee bar and we reminisced about her time at the school. By chance I asked her what she remembered about her last day at school and, not surprisingly, she remembered that Roy Suckling was caned for vandalism which she had witnessed in class. Naturally I asked if he was the only one responsible and she said no another boy was involved and on asking his name can you guess what she said?”
I knew this was coming and realized that I could not deny that it was me so I said “Barry Spockings?”
Headmistress Gray smiled at me saying “Absolutely correct! And she told me where you now lived and that you too had become a schoolteacher. So how do you propose I should deal with this matter?”
I was gobsmacked! I had dated Janet for a while whilst at university but we broke it off unceremoniously so I was surprised that she had kept tabs on me but not so surprised that she had revealed my participation in the vandalism. I did not know what to say to Headmistress Gray and said so.
“Well I consider that there is unfinished business that needs completing. Also I consider that there is interest to pay – your failure to own up was both cowardly and unfair to Roy Suckling, allowing him to take all the blame! In effect you took a loan on his willingness to shoulder all the blame. Well today is payback day and when you take a loan over time there is interest to pay – if you had owned up you would have received the same punishment as Roy Suckling – twelve of the best on your bare bottom! But that was five years ago and twelve strokes at ten percent compound interest over five years earns an extra ten strokes. So I propose to give you a total of twenty two strokes with the senior boys cane on your bare bottom! What do you think?”
I was shocked! But the paradoxical attitude I had towards being caned resurfaced – yes it would be painful but there was the strangely appealing aspect about being punished by a woman, especially a woman as attractive as Miss Gray!
She added “I have checked the school punishment book for the time you attended this school and discovered that you were never caned during your time here. A rare occurrence indeed! But today I intend to rectify this omission despite your age and no longer being a pupil here. What do you have to say for yourself?”
I was at a loss for words – here was I, an adult male facing the prospect of a bare bottom caning from my very attractive ex-Headmistress. Reluctantly I decided to say yes and so I stuttered out the words – “Well if you really think I deserve it and you really want to do it how can I refuse?”
“Good boy! But I warn you it will be really painful as I intend to give you the very hard thrashing I think you deserve. Are you certain that you are willing and also believe that you can take it?”
“Yes Miss Gray.”
“So be it then – but you must do exactly what I say. I have caned many naughty boys’ bare bottoms but up till today they have all been juniors or sixth formers – you will be the first adult male to receive a bare bottom beating from me and I think I am going to enjoy giving your bare bottom the hiding it deserves. I have always found that caning the older boys bare bottoms an exhilarating experience!”
At this she rose from her chair and walked to a slim wall cupboard from which she withdrew a long crook handled school cane, which I presume she applied to senior boys’ naughty bare bottoms.
“The procedure is as follows – I am going to remove your trousers and underpants, you will then bend over my desk and hold on to the far side. You will open your legs and stick your bottom well out and when I am satisfied with your position I will commence caning you. You will stay in position until after the twenty second stroke and I tell you to stand up. If you try to get up or try to resist or attempt to protect your bottom with your hands I will start your punishment over again. You can, of course, cry out as that is to be expected. Is that all understood?”
“Yes Miss.” What more could I say as I had agreed to the caning. However I had developed another problem. The thought of being undressed by this very attractive Headmistress I found arousing and I was embarrassed to feel my penis stiffening. It continued to grow and felt fully erect as she approached me, took my jacket and undid my belt before pulling my zip down and then my trousers which she took off over my shoes. I was wearing only skimpy briefs and my fully erect penis was prominently “tenting” them to the obvious amusement of the Headmistress.
“I see that part of you at least is looking forward to your punishment – but I very much doubt whether your nether regions will enjoy it! Now let’s get these off so I can get down to business!”
She then gently pulled my briefs down, carefully easing them over my erect and now weeping penis.
“My goodness you are a big boy!” She exclaimed “Perhaps later I will see if we can avoid that going to waste.” At which point she gently gripped my penis and led me to her desk before pushing me and it against the woodwork before bending me over it. I did as she said and clutched the far side, opened my legs and stuck my bottom out, releasing my erection which continued to dribble.
“Well done Barry, you are in the perfect position to take a good caning!”
Tantalisingly I heard her swish the cane several times in the air before resting it across the centre of my buttocks. I felt her tap it six times before I heard the swish and on impact it initially felt harmless but microseconds later it became an incredibly painful collision with both buttocks as she thrashed the cane down on my unprotected bottom. I could not help but cry out in pain. Somehow I managed to remain in place but wondered how on earth I could take another twenty one such strokes. About ten seconds later I heard that terrible swish and felt the dreadful agonizing impact of the second stroke. Again I cried out. The next eight cuts were equally unbearable, with me yelling out in distress after each stroke. Amazingly despite the throbbing in my buttocks my penis was still erect and also throbbing!
Unexpectedly she interrupted my punishment saying “I think we both deserve a break and as this activity is tiring I need a glass of water. So just stay in position while I get one.”
I heard her leave the study and lock the door. Despite being told to stay in position I could not resist standing up both to feel my bottom and attend to my penis. Even just touching my bottom was agonizing and I could feel the weals she had embedded into my buttocks. Strangely, despite the pain, my penis remained rigid, leaving me to wonder what she had meant when she said “Perhaps later I will see if we can avoid that going to waste.” Such thoughts, however, came to an abrupt halt as I heard her key in the door and I hastily resumed my prone position over her desk.
“Good boy – you have not moved! I feel refreshed and so we can resume where we left off! But first I want to check that part of you that seemed to be looking forward to your punishment….” I felt her cool hand move between my legs and towards my groin, brushing against my testicles before grasping my penis! “My goodness it is both erect and very hard so, despite crying out in torment on receiving each stroke, the caning has aroused you as much as it has aroused me! Let us hope it maintains this condition right until the end or your punishment! So stick your bottom out I am about to continue!”
As before I felt the cane rest across my buttocks and felt it tap six times before I heard the inevitable swish and resounding crack as it whipped into my poor bare beaten bottom! Naturally I yelled out and continued to do so after each of the next nine strokes. “Now that’s twenty strokes completed and, even if I say so myself, that is a jolly good job well done – your bottom has twenty parallel lines stretching from the base of your spine to the top of your legs! Two to come and they will each be a diagonal in opposite directions – very painful but it will be a work of art to admire when I have done! So brace yourself as these two will really hurt!”
And my god did they! Each stroke cut across twenty earlier ones causing the most appalling agony and I screamed out loud after each of the two strokes.
“Now Barry stay in position while I inspect the damage.”
Gently she felt each of my buttocks, trailing her fingers along each cane track, her cool hands gradually easing the pain as she softly massaged my bottom. I was in heaven and my arousal was now crying out for some attention! She seemed to sense this and once again pushed her hand between my legs before gently squeezing my scrotum and clutching my pulsating penis.
“Well although your caning was undoubtedly painful you obviously found it pleasurable as indicated by the state of arousal of this big boy! You probably have guessed that caning older boys bare bottoms I also find incredibly arousing so shall we indulge each other a little?”
My goodness this was totally unexpected but how could I say no given the state of my throbbing penis and her undoubted sexual appeal? So I readily agreed and she made me stand up and fully kissed me on the lips.
“Well my very naughty boy I like being taken by well-endowed men like you from behind in doggy style. Do you think you could oblige if I undress and bend over the desk?”
Could I? This was the subject of so many of my unfulfilled dreams! So I readily agreed and watched her slowly disrobe. She slipped her black figure hugging skirt to the ground revealing black stockings, matching suspender belt and red silk panties. On slipping off her white silk blouse I saw she was wearing a red bra matching her panties. All in all a very sexy outfit and not one I would be expecting a mature Headmistress to wear! But more was to come as she removed her bra revealing two well formed and ample breasts and then seductively slipped out of her panties.
“Now are you ready? “She said bending over her desk with legs wide open and her already wet pussy just waiting to be plundered!
I was more than ready and positioned myself behind her with my erect and dripping penis ready to pound her pussy and provide the sexual relief we both needed. And so I slowly entered her and she pushed backwards inviting more vigorous penetration. I obliged and she screamed out in ecstasy as I pounded in and out until we both climaxed simultaneously.
“Barry that was amazing! Can you remember any other naughty exploits you got up to at school and got away with?”
“Why?” I asked.
“I thought you might like a repeat performance!”
D I S C L A I M E R
All characters and businesses appearing in this story are fictitious. Any resemblance to real persons, living or dead, is purely coincidental.
Story and photographs ©MMXXII by Barry Spockings, used here by very kind permission.
Authors and the site management appreciate your feedback. Please leave a comment on this excellent story. Comments on this story are here.
Barry Spockings’ excellent earlier stories for The Canery are available here. Further stories by Barry Spockings are at this external link.