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The Cane, Miss Bush, and Me Part 3

It was late August and a few days earlier I’d received good news about my A Level results. My grades were good enough for me to go to university and it wouldn’t be long before I had to pack my things and head off to the opposite end of the country.

I’d decided to wander across to the amusement arcade to see if any of my friends were about as they often hung out there. In truth the Summer holidays were becoming rather boring and I was already in university mode, well, in my mind at least, as I imagined the vast number of attractive girls I expected to encounter when I got there.

Although Sandra had continued to feature regularly in my masturbatory fantasies, my interest in her in the real world hadn't come to much. I did though, get to fuck her a second time, which proved eminently more successful than the first attempt as it lasted considerably longer and I was fairly confident, brought her to orgasm. Well, if it didn't, she certainly put on a bloody good display!

Early in August and having not seen Sandra around for a few days, I'd casually spoken to her mother while she was watering the plants in her front garden, and asked how Sandra was. “She's gone back to Birkenhead love, to live with her boyfriend now that he's decided to leave the army,” she said. “Sandra's father and me have never been keen on him, thought she might have had a change of heart and settled down here when she met you.”

I smiled and went on my way slightly puzzled that Sandra's mother knew anything about me. Damn, did she know that I'd been in her house and fucked her daughter twice, I wondered!

I did though feel slightly flattered that Sandra had mentioned me to her parents even if she did already have a boyfriend that she'd never told me about. Perhaps she actually liked me a bit after all.

My route to the arcade took me through the park and with the weather still totally glorious, it was awash with the colours of people in summer clothes sat at picnic tables or laid on blankets on the ground with some stripped off as far as legally allowed with tinny sounding transistor radios blaring out as they soaked up the sun. Thankfully there were plenty of scantily clad young women around, with at least some of them well worth a second glance.

The small cafeteria at the centre of the park appeared to be doing a good trade with people heading back to their chosen spot carrying ice-creams and chilled drinks and others constantly joining the queue to be served.

As I followed the path which ran close to the cafeteria, I heard my name called out, “TOBIAS....TOBIAS, OVER HERE.” I paused and looked around, unable to distinguish who had called me and not immediately recognising the voice above the cacophony of sounds around me.

I then spotted an arm waving and noticed Miss Bush in the cafeteria queue beckoning me over. Thoughts of that involuntary erection flashed through my mind and triggered inner embarrassment, but I went over to her anyway.
“Join me for and ice-cream Tobias,” she invited. I smiled and accepted.

Miss Bush looked totally gorgeous in a pale lemon skimpy summer dress and white sandals. Since my brief encounter with Sandra, Miss Bush was never far away from my fantasies, yes, she had made a full return.

In my fantasies, Sandra's beautiful bottom had been caned by Miss Bush countless times, as had my own. Sometimes Miss Bush had made me cane Sandra and Sandra cane me. Sometimes we had caned Miss Bush and most of my fantasies included various permutations of sex between the three of us. God, where did these bizarre ideas come from?

Perhaps Sandra's mother would be glad that her beautiful daughter had gone back to Birkenhead if she had even the slightest inkling of the fantasies I'd included her in!

As soon as Miss Bush was served at the cafeteria, she handed me the ice-cream she'd bought me and we sat at one of the cafeteria tables and talked about my university plans, she congratulated me on my A Level grades.

“Thanks for the ice-cream Miss Bush,” I said as my eyes were drawn to her deliciously pink, moist tongue as it stretched provocatively from her mouth as she begin licking her vanilla cornet. I was unable to avoid imaging her doing the same to my cock and with the weather seeming hotter than ever, the sight of perspiration trickling down Miss Bush's face and from the tops of her shoulders, made her seem even more sexy than ever.

Oh, my God! Miss Bush was immediately back at number one with Sandra hastily moved down to number two!
I began to imagine my former headmistress naked as I rubbed her intimate parts with my ice-cream, watching it melt on her breasts and vagina and trickle into the glorious valley between her buttocks, cooling her in the heat of the sun before I licked off every last drop entwined with the delightful, salty aroma of her perspiration.

Beneath the table, my cock began to grow and I thought that maybe I'd forget going to the arcade and return home for a wank instead!

“Is your ice-cream okay,” she asked, bringing me back to reality.

“It's delicious Miss Bush,” I replied, almost wanting to tell her that in my opinion she was even more delicious than the ice-cream!

“By the way Tobias, it’s not Miss Bush any more,” she said with a broad smile.

“You mean you’ve got married?” I clumsily blurted out in shocked fashion, secretly hoping this wasn’t the case.

Miss Bush laughed, “No Tobias, I mean you’re no longer one of my pupils so I’d prefer it if you called me Karen.”
I felt myself blush as despite the embarrassment of being caned by her and that bloody erection, I couldn’t help but think about the umpteen fantasies in which she played a starring role as I'd masturbated. Calling her by her first name somehow just didn't seem right. Teachers were the enemy, or at least they had been for me up until recently, tormenting her in my fantasies had always seemed like a perfectly acceptable form of retribution.

With ice-creams consumed, I expected to bid 'Karen' farewell and had decided that I'd forget the arcade and head straight home to masturbate about her, but as we walked slowly toward the park gates, she placed her hand on my arm and softly said, “I'm going for a dip in the school pool to cool down, why don’t you come and join me Tobias?”
Perhaps my imagination was running away with me, perhaps not, but the touch of her hand and this unexpected invitation had caused another stirring between my legs. As I glanced down at my crotch I was relieved that despite the tightness of my cut off denims there was no noticeable bulge.

I paused for a moment before answering, “I suppose I could join you, I haven't really got any plans for this afternoon.” Knowing that to decline this offer would probably haunt me forever.

As we walked the few yards to her car parked along the tree lined avenue which bordered the park, the butterflies in my tummy seemed to be doing acrobatics, but as I squeezed myself into the snug passenger seat of Karen's Triumph GT6 and we set off on the mile or so journey to the school, I began to feel more at ease.

My mind though, was invaded by the thoughts of what happened the last time I entered that swimming pool, but curiously, these were not entirely unpleasant thoughts!

Pulling up outside the school gates, Karen asked me to take the large bunch of keys from the glovebox and open the gates. As she drove through she called through her open window, “Better close and lock the gates again Tobias, we don't want any intruders spoiling our fun.”

The emptiness of the school grounds and the silence of the imposing school building during this summer holiday period, made it hard for me to believe that it was the same place that I had attended every school day for almost eight years, but as the sun continued to beat down, my thoughts were quickly redirected to cooling off in the swimming pool with Karen. Perhaps she liked to swim naked I considered!

Karen unlocked the main door to the school and ushered me toward the study, “I don't suppose you have trunks under those shorts.“ she said. I shook my head and chuckled, “I haven't actually got anything on underneath. It's fine though, I can swim in them, I'll just take off my top and trainers,” I replied.

Karen smiled, “It's up to you but I'm sure there will be some trunks in lost property if you want to go and look.” I declined the offer and simply glanced around the study as thoughts of the many fantasies that I'd based in that very room, percolated through my mind.

“I'll just go in here and put on my costume,” Karen announced as she headed into her private cloakroom.
As I awaited her return my eyes focused on the desk, the scene of my caning almost eight weeks earlier and the setting for so many of my fantasies about Sandra. Despite the anguish of my caning, I had a powerful desire to bend over that desk again and offer my naked bottom for punishment.

Peeling off my top and kicking off my trainers, I emptied the pockets of my shorts in preparation for my dip in the pool. Apart from some loose change that I'd intended for the machines in the arcade, I found the one remaining condom from the packet I'd purchased with Sandra and hastily wrapped it inside my discarded top out of view. Damn, was it really over six weeks since I'd last had an actual fuck!

Karen emerged a few minutes later from her cloakroom clad in a white swimsuit and holding a towel somewhat larger than the towel she had given me to dry off on the day she had caned me. My eyes feasted on the delicious display of her near perfect contours afforded by the swimsuit.

“Okay, shall we go and cool off?” she asked rhetorically as she headed for the study door.

Following her to the pool was a delight in itself. The snug fitting swimsuit displayed her bottom to perfection and my eyes were immediately drawn to every movement of that bottom as I followed her to the pool.

I was first to enter the water, diving into the deep end, perhaps trying to demonstrate to Karen that I was a strong swimmer and her judgement of my aquatic skills on the day of my caning was totally unfounded.

I swam a few lengths as Karen edged her way down the ladder into the shallow end claiming that she did not wish to get her hair wet as it would go frizzy. “I'm not really much of a swimmer,” she informed me. “But I do like to come here most days for a dip as I find the water so refreshing in this hot weather.”

I recalled the fantasy I'd had about fucking Sandra in the pool and the part 'Miss Bush' had played in caning us both for our trouble. Perhaps Karen would like to hold onto the side as I fucked her from behind I thought. We could certainly do that in the shallow end I fantasised.

We didn't stay in the pool for very long, but as I watched Karen, suitably refreshed, climb the ladder out of the pool, my eyes once again focused on her glorious bottom. With her swimsuit now wet, its white fabric was close to transparent and to my delight, left little to the imagination.

As I followed her out of the pool we quickly moved to stand on the grass as the heat of the paving slabs which surrounded the pool was too much for bare feet to tolerate for long.

Karen wiped herself down with the towel she had brought, pressing it hard against her swimsuit to remove as much water as possible before handing the towel to me. The damp feel of the towel from Karen's body created an erotic feeling within me as I used it to dry myself.

Once back in the seclusion of the study I looked into Karen's sparkling blue eyes and she into mine, although she said nothing I somehow knew that she hadn't brought me here just for a swim.

Slipping down my shorts I could feel my pulse racing as I wondered whether I was making a terrible mistake, but as I stood naked she stepped forward and placed her hand around my cock, simultaneously bringing her lips to mine, causing my doubts to immediately evaporate.

I could feel my cock begin to swell ever harder within her grasp and I could only hope that my one remaining condom would soon be put to good use.

“Take off your swimsuit,” I whispered in her ear. “I've imagined you naked since the moment I first saw you.”
Slowly Karen stepped back and peeled down the shoulder straps of her swimsuit, her tongue erotically travelling around her lips as she did so. I stood and watched her every motion as she slowly peeled herself free from this garment and achieved the nudity I so desired.

“God, you're even more beautiful than I'd imagined,” I told her as my eyes drank in the perfection of her body.
Magnificent breasts displaying the delightful hardened buds of her nipples and the perfect symmetry of her areola was indeed a feast for the eyes as was the neatness of her closely trimmed vaginal hair.

As Karen slowly revolved, displaying her full charms, I was to enjoy my first proper view of her naked bottom. Delicious feminine buttocks, beautifully contoured like two identical tear drops placed side by side tapering down to beautiful thighs and shapely legs that had long since captured my attention.

As I stepped back mesmerised, it was Karen's turn to compliment me.

“You're an attractive young man Tobias,“ she said with a broad smile. “I've thought about you many times since that day.”

I of course, knew the day she meant even if she seemed to avoid saying it outright. “You mean the day you caned me?” I offered with a slight giggle, relishing the opportunity just to say it.

Once more we brought our lips together, and as our tongues entwined I explored Karen's delightful buttocks with my hands as she once more slipped her fingers around my cock immediately restoring it to full hardness. God, after all the fantasies I'd had about that magnificent bottom of hers, I actually had it grasped in my hands!

“What would you like me to do for you?” she asked softly.

Pausing for a moment, I gently brushed the golden ringlets of her hair away from her ear, my lips brushing against the gold, hooped earring on her left ear as I whispered, “I want you to cane me 'Miss', just like you caned me before.”
As I stepped back awaiting her reaction, she smiled, “I think I can manage that, but only if you promise to fuck me completely senseless afterwards.”

I smiled back, “Try stopping me,” I replied. “I've got a condom with me,” I added, immediately considering how juvenile this must have sounded to a woman in her mid-thirties.

I watched as Karen turned toward the stockroom, my eyes transfixed on her naked buttocks as I wondered whether in the real world she had ever been on the receiving end of a caning herself. Perhaps I should ask her, perhaps she would tell me that she wanted to feel the cane across her own buttocks. Maybe though I shouldn't overstep the mark at this point.

Karen returned a few moments later clutching what appeared to be the same crook handled cane which she'd used on me following the swimming pool incident. She now sported a tasselled mortarboard perched on top of her wild ringlets of golden hair and I was immediately reminded of a saucy calendar I'd seen in the office of the garage where my friend's brother worked as a mechanic.

My god, I needed to pinch myself to make sure that I wasn't dreaming. The sight of a beautiful naked woman in a saucy photo' was one thing, but actually being in the presence of one clutching a traditional school cane and wearing her academic cap was beyond my wildest imagination.

“So Tobias, tell me what you've been up to to deserve another caning,” she said with a mischievous tone to her voice. I hadn't planned for such a question but responded with the first thought that entered my head, “ I've been masturbating Miss, masturbating a lot.”

Karen turned and pointed the cane toward the desk.

“Put the telephone on the window sill and bend over the desk,” she growled. “It's twelve hard strokes of the cane for your disgraceful behaviour, young man.”

I removed the 'phone and leaned across the desk gripping its far edge. As I did so, the smell of polish entered my nostrils and almost made me sneeze. I imagined that during the holidays, the study, as with the rest of the school building, had received a thorough clean in readiness for a new academic year.

With my position settled and my bottom at Karen's mercy, I gritted my teeth and awaited my fate, my eyes once again focusing on the panoramic photograph of the whole school which hung on the centre of the wall in front of me.
This time though, it was a new photograph taken towards the end of the last term. From the range I was viewing it, the photo was little more than a sea of indistinguishable faces, but I could make out Karen positioned at the centre of the front row and knew that I was somewhere towards the left in the back row.

As I felt Karen address my bottom with the cane I questioned myself as to what the hell I was doing relishing the kind of punishment that had sent total trepidation through just about everyone who had attended this school and just about every other school in the land for the last hundred years or so.

Thoughts flashed through my mind of even the toughest of individuals reduced to tears as they had bent over this very desk and returned from this very study following a caning.

I recalled amongst others, Joanne Powell, a vicious bulldog of a girl, who struck terror into the hearts of many a fellow pupil, reduced to a blubbering mass after just six strokes of the cane on her fat and thoroughly unappealing bottom.
Steven Wheeler also, a bully and giant of a lad who cast fear into his fellow pupils, reduced to crying like a baby after a caning from Mr. Pickering.

With the cane touching the pinnacle of my buttocks I somehow welcomed the first stroke, if only perhaps, to reassure myself that I would really be able to cope with the pain.

Since my last caning I had many times fantasised about being caned, but at this very moment I truly had doubts about the wisdom of my request.

Karen paused and ran a hand over the contours of my bottom, sliding a finger the full length of my cleft. “You have a lovely bottom Tobias, quite beautiful,” she informed me. “But it needs to be caned hard to teach you a lesson.”

“I understand Miss, I deserve it and by the way, I like your bottom too,” I replied. Karen chuckled, presumably at this compliment.

“Right Tobias, twelve strokes of the cane and if, when your caning is complete, you display even so much as a hint of an erection, I'm going to make you fuck me. Is that clear?”

I enjoyed Karen's humour and nodded my head, “Yes, Miss, perfectly clear.”

As the first stroke landed across the centre of my bottom, I gasped as its full ignition exploded in my bottom. Despite the pain, I was determined to remain as stoic as possible.

The second and third strokes arrived swiftly and with little time between each, slicing into my flesh and feeling like I'd had a red hot poker thrust against me. “AH, AH, AH, OW,” I shrieked as I near crushed the edge of the desk with my hands.

As the next three strokes arrived, they compounded my agony and as I tensed and untensed my body to quell the pain, I questioned in my mind why on earth I was putting myself through this.

With six strokes administered, Karen lowered the cane and gently ran a hand over my throbbing buttocks. “How does your bottom feel?” she asked. “It hurts Miss, but sort of in a good way,” I responded, my words somehow bizarrely reminding me of the Millie Jackson record from a couple of years earlier, 'It Hurts So Good'. Had my predicament been different I'm sure I would have begun humming the tune!

Placing the cane on the surface of the desk next to me, Karen placed her hands on my hips and eased herself toward me, slowly and deliberately rubbing herself intimately up and down my wounds. The coarseness of her neatly trimmed vaginal hair as it tickled against my buttocks and the moistness of her seeping juices almost made me want to cum there and then as my erect cock pressed ever harder against the hard surface of the desk.

Karen whispered in my ear, “I'm going to give you the final six quickly Tobias, I can see that you're enjoying this just a little more than you should, so remember, my cunt is ready and waiting for you.”

As she picked up the cane for the final onslaught I once more braced myself.

The seventh stroke landed on my buttocks squarely and firmly and was swiftly followed by the eighth and ninth. “EEEEE-OW,” I cried as my behind felt ready to burst into flames. With the next two strokes delivered with equal swiftness close to the point where buttock and thigh merge, I began to contort wildly as the agony became close to unbearable as it spread down the backs of my legs.

“Just one more to go Tobias,” announced Karen. “This one's going to be the hardest. Are you ready?”

“Yes Miss, I'm ready,” I replied, my voice strained from my agony.

As Karen tapped the cane gently against the centre of my bottom, I held my breath and tightened my grip on the desk in preparation for what I knew would be an excruciating finale to this caning.

Suddenly and without warning, Karen drew the cane back, bringing it down squarely across the centre of my bottom at seemingly full force, causing me to thrust myself upright as its impact fully ignited. “OW, WOW, WOW, OW,” AH, AH, OH GOD, AH,” I yelled . It was a final stroke that certainly didn't disappoint, and for a brief moment I truly wondered whether I would ever be able to compose myself again.

With my caning over, Karen discarded the cane and guided me to bend back over the desk as she examined my ravaged buttocks.

Dropping to her knees, she placed a kiss on the centre of each of my quivering cheeks before running her tongue along the swollen ridges that now embossed my once smooth skin. “Is that soothing Tobias?” she whispered as she paused her attentions.

“It's very soothing Miss,” I replied thinking that I would be very happy for her to lick me forever.

Karen slowly eased my buttocks apart exposing my anus to the air and doubtless her view, before prodding a finger against it.

Despite the attentions of her tongue, the pain in my buttocks remained close to unbearable, but in the knowledge that it wouldn't be long before the initial agony subsided into the pleasurable soreness of the aftermath, I had no regrets at having requested this punishment.

“Okay Tobias, stand up and let's take a look at that cock of yours.”

I knew it was hard, perhaps not fully hard, but hard enough to convince me that submitting myself to a beautiful woman for a caning was something that I curiously craved.

“Well Tobias, I warned you what would happen if your cock was in any way stiff after I caned you,” grinned Karen.

“You did Miss,” I replied managing a smile through my agony in return. “Does that mean I have to fuck you now Miss?” Just uttering these words, enough to further swell my cock.

Karen clasped my cock in her hand, “It's a lovely hard cock Tobias, far better to use it for fucking than masturbating, so I hope you've learned your lesson.”

Dropping to her knees, Karen took my rigid member in her mouth and clasped my tender buttocks in her hands, the firmness of her grip causing me to wince. Slowly, she pulled herself back and forth, my fantasising in the park as I'd watched her lick her ice-cream, seemed to have truly come to reality!

As I looked down, the sight of the mortarboard perched precariously on her head with its tassel flicking back and forth in unison with her movement, seemed to send me to the point of no return. Suddenly and uncontrollably I released into her mouth, the mortarboard falling from her head as I did so. Damn, had I blown my chance of fucking her properly?

Karen continued to suck hard at my cock as if ensuring that she had every last drop of my cum before rising to her feet and swallowing it down before my eyes.

Being sucked by Karen was certainly mind-blowing, there was no denying that, but at the same time, I felt a sense of dismay that my hopes of fucking her properly, now seemed lost.

“It's okay Tobias,” said Karen softly. “I actually wanted you to cum in my mouth, you'll soon recharge and when you fuck me I want it to last.”

Well, if some had doubted Karen's ability as a headmistress during the two terms she had been at the helm, I could now at least vouch for her teaching skills!

Cradling her breasts in her hands, Karen offered them for my attention. As I began to knead them, sucking the hardened buds of her nipples as I did so, I had little doubt that my passions would soon rekindle. With the right stimulation passing through my veins, I knew from experience that I was able to masturbate multiple times within a short period.

I have never considered myself a breast guy and although Karen's offering was a delicious 'hors d'oeuvre' to the main course, I rapidly progressed to that part of the female anatomy that I seemed uncontrollably programmed to find the most stimulating.

Guiding Karen to lean forward over the desk, I slid my hand over the perfect contours of her buttocks and as I began to knead and squeeze her supple, smooth flesh I was soon to become aware that my languid cock was already beginning to reawaken.

Easing these beautiful buttocks apart, I caught my first glimpse of her neatly puckered anus and with my fingers straying between her legs, I teased them against her deliciously moist cunt lips. After leaning down and tasting the flavour of her juices, I drew my tongue the full length of her cleft, brushing its tip against her anus as I did so. “ Have you ever been caned Karen?” I felt compelled to ask.

Karen gave a slight giggle before answering,”Oh yes, I was caned quite a few times at school, not always on my bum though, depended on who was giving the caning. Sometimes it was three strokes on the palm of each hand if it was Mrs. Bartholomew the Deputy Head.”

I smiled to myself, I had never before considered a hand caning to be particularly arousing, but where Karen was concerned, for me any part of her beautiful body being caned would have seemed unbelievably erotic.

“I had a boyfriend a few years back who liked to cane me,” continued Karen. “But it's the 'handle end' for me these days, think I'd die if anyone caned me now.”

As I concluded my scrutiny of her magnificent bottom I imagined the pleasure which would have been afforded me had she invited me to cane her. My overactive mind almost hearing her saying, 'Cane me Tobias, just like I caned you. I am guilty of endlessly fantasising about you since that day I first saw your swollen cock in this study. Cane me hard Tobias, I thoroughly deserve it.'

Alas, this was just the ramblings of my imagination, but if nothing else, I knew that my future masturbatory fantasies involving Karen were about to take an even more interesting turn!

With some further assistance from Karen's hand, my cock was once again restored to full hardness and as I passed her the one remaining condom from the pack I'd bought with Sandra, my entire body tingled as she expertly unrolled it down my throbbing shaft.

Karen sat herself on the edge of her desk and slowly laid back with her knees raised and apart. The sight of her simmering, moist cunt beckoned me towards her like a powerful magnet and even if my life had depended on it, I doubt that any amount of willpower could have stopped me from guiding my cock between those moist and welcoming cunt lips.

I had fucked Karen many times in my fantasies, but as I stood between her legs with the front of my thighs close to the edge of the desk, I slowly worked my swollen member in and out of the delicious chasm she offered. The pain in my buttocks from the caning was still there, but had mellowed into more of a feeling of stinging and warmth, and as I built up my rhythm, the tenderness of my buttocks as my muscles expanded and contracted, only served to add to my arousal.

As my member continued its quest in earnest, Karen soon began to cry out, her magnificent body squirming across the desk as my cock was driven in deep. Clutching her thighs under my arms, the feel of her delightful, supple flesh against my skin, convinced me that despite being sucked off by her only a matter of minutes earlier, the end of this amazing journey was getting ever closer.

“OH YES, KEEP FUCKING ME, PLEASE DON'T STOP,” cried Karen, elevating my own arousal ever higher.

“AH, AH, OH GOD, YES, YES, YES “ she cried, then moments later her entire body seemed to weaken as she flopped back like a beautiful rag doll. Karen had doubtless reached her personal crescendo.

With Karen laid back, heavy perspiration glistening on her skin as she breathed deeply, I continued to thrust inside her, my own crescendo still to come. Deepening my strokes ever further and thrusting ever harder I knew I was close and then suddenly and magnificently, my quest was at an end.

As I too weakened, I leaned forward and kissed Karen's delicious mouth, the perspiration on both of us near bonding our bodies together, and at that very moment in time, I would have happily remained bonded to this beautiful woman forever.

Hell, after the countless times I'd masturbated about Karen, I'd actually fucked her for real, a totally amazing fuck, without doubt the best yet!

As we remained entwined across the desk, Karen glanced at the clock on the wall, “ I think you should get dressed and get off home,” she said. ”Mr. Hinton, the caretaker does his rounds early evening but has been known to sometimes come a little earlier, best if he doesn't see you.”

Prising myself off of my former headmistress, the squelching sound of our flesh separating from each other caused us both to laugh. My now softened cock slipped easily from her beautiful cunt and I had to grasp my condom to stop it falling to the floor.

Back on my feet, I hastily gathered my things and dressed quickly. My still damp cut off denims feeling good against my sticky skin and sore buttocks. Karen though, remained naked and as my eyes once more scanned her beautiful body, I thought of how much I'd have liked to have stayed a while longer and complete my personal 'triathlon' with her, even though at this time in my life I had only experienced anal sex in my fantasies.

Karen gently placed a finger under my chin and looked at me seductively, “When you come back from university Tobias, make sure you get in touch so that you can tell me all about what you've been up to. I'm sure there'll be plenty of good reason for me to cane that lovely bottom of yours again.”

I smiled and as I let myself out of the study door I took one final glance at Karen's beautiful, naked bottom as she turned towards her cloakroom. It was an image that I so wanted etched in my mind forever.
As I let myself out of the building and took the route to the gap in the fence that I'd used so many times before on my way home, I couldn't resist jumping into the shallow end of the swimming pool to cool myself off and remove the perspiration from my body.

My desire to have anal sex with my beautiful, former headmistress may have eluded me on this occasion, but as I clambered through the gap in the fence and headed along the pavement on my way home I knew that when I reached the privacy of my bedroom, Karen's arsehole would play a major role in my next masturbatory fantasy.

From the day of my arrival at university it didn't take long for me to compile my new 'wanking list.' With so many attractive girls to choose from, I was spoilt for choice and sticking to my own rules of only ever including ten girls on my list at any one time, I could afford to be extremely choosy.

When I was at school, it was often difficult to find ten girls worthy of masturbating about, but university was a whole new deal.

With so many 'hungry' girls to choose from and living on campus in my own private room, I was soon to add to my sexual conquests. The words of my former football coach, Peter Burrows, remained firmly in my mind though, 'Sex is really great, but you really can't beat a damned good wank.'

Yes, despite my conquests, I continued to masturbate more than regularly. With new girls on my 'wanking list,' some of whom I'd been privileged to fuck for real, I was never short of stimulation.

Although Sandra had somewhat drifted away from my thoughts, only making the occasional appearance in my fantasies, Karen Bush remained at the top of my list and I masturbated about her frequently. Knowing that I would soon be back home for the mid-term break, I longed to once more be in her study and receive another caning on my naked buttocks. Perhaps this time I would actually get to sample the 'fuck hole' that had so far eluded me!

Shortly before the mid-term break though, I 'phoned home as I did most weeks and spoke to my mother. As usual, she was keen to make sure that I was taking care of myself as well as updating me on all the local gossip.

As our conversation came near an end she suddenly added, ”Oh, I nearly forgot to tell you. I bumped into Mrs. Draycott the other day in the post office. You know who I mean, her son Simon was in the year below you at school and she's got a daughter a bit younger than him. Well, she told me that new headmistress has been sacked.”

Shocked at this news I felt compelled to ask,” What's she been sacked for she was really nice?”

“Well, apparently,” continued my mother. “ She was caught with some young fellah who'd gone to do some work in the school one evening, a plumber, electrician, carpenter or something. One of the governors found them in her study with no clothes on having sex on her desk.”

A flash of embarrassment passed through my entire body as I wondered what my mother would have thought had she known about my own encounter with Karen in late August!

“Mrs Draycott thinks she's gone to Australia or it might be New Zealand, to avoid the scandal because she'd be lucky to get another teaching job here. That Mrs Abbott's in charge again now,” added my mother.

Knowing that I was never likely to see Karen again was truly devastating news for me. My mid-term expectation of another caning from Karen completely dashed.

What I did though know for sure, was that Karen Bush had taught me about myself, expanded my horizons. My curious fascination with the cane had at one time focused only on the bottoms of beautiful young women getting caned, something still immensely pleasurable to me.

Karen though, had taught me that submitting myself to a beautiful woman for a caning was something that I curiously craved and whatever the future held, this was now a part of me from which there was almost certainly no going back.

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to Sleazeboy: Thank you so much. I'm so pleased you enjoyed the story as I really enjoyed writing it. Positive comments are always great to receive and spur me on to write more in the future.
With this oeuvre you really have elevated the genre to new heights...beautifully written and highly erotic, I found myself massaging my knob through my pants, until I could not resist the overwhelming urge to enjoy a very satisfying wank at the caning scene. Just superb!!
4 months ago