Object of the Teacher’s Attentions

1970’s twelfth grade English. Missus O’Callahan. A statuesque redhead with a beguiling Irish lilt to her voice. I had no idea if she was really attractive but at the time I was captivated, enthralled. It didn’t hurt that she wore miniskirts and sat on her desk in front of me giving me many glimpses of her colorful panty collection. These views of her exotic panties would lead to furious masturbation sessions when I got home.

Miniskirts were everywhere and glimpses of the girls and even a teachers panties was common, especially if you put a little effort into it. I seemed to put in more than most. It had gone from a passion to an obsession and Miss O was a regular feast for my eyes and imagination. Unlike the usual pedestrian panties that the girls my age wore the view up Misses O’s skirts was always something spectacular. She often didn’t wear pantyhose which gave to better viewing of her panty selections and on occasion she would even wore nylons with a garter or girdle.

Another boy, a bully, noticed that I was often distracted in English and soon figured out why. He was big for his age while I definitely wasn’t. He started teasing me and I tried to ignore him but he was relentless. Finally in frustration I lashed out at him and he responded violently. Luckily for me a teacher broke up the fight before he could inflict too much damage but we were both marched off to Mr Wagner’s the vice principal’s office. The large unhappy man then delivered ten of his best with the school’s strop across the palms of our hands.

The bully took his and though he looked like he was going to cry, he didn’t. I had never been strapped before and I was bawling after the first strike. After the second I pulled away only to be told that if I did again the punishment would start over. It really really hurt and it didn’t help that I could see my tormentor smiling out of the corner of my eye. I knew he couldn’t wait to tell everyone what a cry baby I was. And he did. Soon I was the object of nearly everyone’s taunts and ridicule. Even the girls wouldn’t leave me alone. Finally when it was too much I again lashed out at another student. It was in Miss O’s class and her voice shrilled as she berated me for my behavior. Taking me roughly by the arm she marched me out of the classroom heading for the school’s offices.

I broke down in terror before we got ten paces down the hallway. My distress was so apparent that Misses O looked at me astonished. I pleaded with her through tears not to take me to the office to face Mr Wagner. Babbling almost incoherently I promised to be good, I promised to behave, I promised anything. While I wept Misses O loomed over me seeming far from impressed until eventually disgusted with it all she relented and gave me a week of detention instead of a visit to the vice principal.

Overcome with relief I enthusiastically agreed, pledging that I would not let her down. Unimpressed Misses O told me to stay in the hallway until the end of the class to compose myself and left me there sniffling. I watched Misses O walk away with her nylon covered legs disappearing beneath the hem of her short skirt. The slit at the back of her skirt parted with every step giving me fleeting glimpses of the tops of her nylons and just maybe a glimpse of her colorful panty. I sniffed back a tear and chewed on my lower lip secretly thrilled that I had a week’s detention with Misses O.

The other kids remained relentless making the rest of my school day a nightmare but at least I had my detention with Misses O to look forward to. As soon as last bell sounded I sped through the hallways to get to her classroom. When I entered she was doing paperwork and ignored my presence. I stood there respectfully silent until she finally looked up at me and I shivered with anticipation. Misses O just stared at me seeming to be silently gauging my worth, perhaps enjoying the hold her power as a teacher had over me.

As if in a dream Misses O finally murmured, “Sit there,” while pointing purposefully at the desk in front of her. “Books on the floor,” she intoned deliberately. “Hands on the desk, eyes straight ahead,” Misses O directed me, “back straight David and no fidgeting.” Her use of my proper name sent another tingling shiver through my body. I felt my nostrils flare as I drew a ragged breath trying not to stare at her while acutely aware of the erection growing in my jeans.

I could feel Misses O’s gaze on me but didn’t dare meet it. After a while I heard papers being shuffled and realized that she had returned to her work again ignoring me. Dutifully I kept my hands on the desk, eyes forward and back straight and did not fidget. After what seemed like an eternity Misses O rose and moving into my sight of view began writing on the chalkboard. Her body seemed to move with more animation than usual as she scrawled out a list on the board. It was disturbingly hypnotic all the more so because when she had stood up Misses O hadn’t adjusted her skirt appropriately and as I watched captivated the slit at the back open and closed exposing tantalizing views of her purple lace panty. My erection was becoming painfully hard.

I stared transfixed until Misses O abruptly turned startling me. I gaped into her bemused twinkling eyes terrified that she knew exactly what I had been staring at and worse knew what I was thinking about while staring at her panties. Misses O’s amusement faded as she announced, “David, you will complete each assignment I have listed here and present that assignment to me each day of your week of detention.” Misses O stood aside so that I could read her list and her amusement returned as she watched the realization of how much work she was giving me dawned on me.

“Any questions David,” Misses O inquired obviously amused. When I couldn’t find the words to answer she snorted her disdain before informing me derisively, “Hadn’t you better write this down David?”

I frantically scrambled for my books on the floor so I could comply. While I wrote down her list Misses O moved a wooden straight back chair in front of my desk. When I had finished I managed to look up at Misses O expectantly and was unnerved to see the implacable glare she was casting upon me while tapping a wooden pointer into the palm of her hand. “Stand,” she announced abruptly while drawing a deep chest heaving breath that stretched the thin material of her blouse over the lacy brassiere beneath. I tried not to stare at her nipples as she watched on unimpressed at my fumbling attempt to comply and hide my erection from her probing eyes.

Misses O made me stand before her until it suited her to curtly demand, “Come here,” indicating the place before the chair with her pointer then snarling, “kneel on the chair David.”

Startled by her tone I quickly complied without thinking of the implications of what I was going on. “Hands on the back of chair David,” Misses O requested haughtily. Uncertainly I gripped the back of the chair becoming so nervous that my body shook with apprehension. Coolly Missus O murmured, “Palms up David.” Hesitantly I complied, fearful of what Missus O was getting to.

As I knelt there on the hard wooden seat Misses O laid her pointer over my upturned palms. I swallowed hard dreading the possibility that Misses O would use her pointer like the vice principal had used his strop. My body trembled as I fought to hold my position for her while Misses O casually strolled around humming quietly to herself. I shivered when she lent into me from behind. I could feel the heat of her breast and the lace of her brassiere as she pressed into my shoulder. Breathing into my neck she murmured quietly into my ear, “Each assignment done to my satisfaction David.”

Misses O’s hot breath on my neck caused my body to shudder as she continued to lay down the terms of my detention to me, “If I deem your efforts to be inadequate David you will suffer a punishment.” Drawing a deep shuddering breath I tried not to contemplate what Misses O could mean by ‘a punishment’.

Unrelenting Misses O continued, her murmured words and hot breath overwhelming my senses, “I will allow you to choose your punishment David.” Misses O allowed me a moment to tremble before hissing maliciously in my ear, “Do you understand David?” When I could only muster a whimper in response Misses O continued, “You will learn to understand David.” Abruptly she pulled away leaving me panting for breath, my body trembled uncontrollably and a painful erection strained against the crotch of my jeans.

While I held my position on the chair as best I could Misses O retrieved her pointer and flicked so that it whistled through the air menacingly while she stated matter-of-factly, “you will have two choices to start with David.” I couldn’t help flinching when she dramatically flicked her pointer towards my upturned palms only to arrest the motion in time for it to merely tap against my finger tips. I chewed on my lip to stop myself from crying out with fright and anticipated pain. Tapping her pointer repeatedly across my palms and fingers Misses O smiled her eyes twinkling malevolently, “Your choice will be between your hands David or your buttocks.”

As she drawled out ‘buttocks’ Misses O raised her pointer and as it swished through the air behind me I was expecting another dramatic show only to be utterly shocked when the pointer painfully lashed my buttocks. I lurched forward on the chair howling my surprise nearly falling off. Tears filled my eyes as I tried to regain my balance and not outwardly cry.

Misses O rested her pointer on my buttocks as she again lent forward pressing her breasts into my body while breathing in my ear, “Oh I’m sorry David but I wanted that to be a reasonable representation of what you can expect if you choose your buttocks over your hands.” With that Misses O stepped back abruptly and I cringed as her pointer again swished through the air to crack searingly across my upturned palms. My fingers clenched tightly into fists as the white hot pain radiated out through my body. Biting my lip and squeezing my eyes as tightly as possible against the agony of the lash I whimpered silently.

Misses O was back whispering in my ear, “As you can feel David across the palms is very painful and I now see that my earlier demonstration on your buttocks just isn’t sufficient to give you proper context for when you will have to make your choice.”

As she prattled on I tried to regain my composure only noticing too late that Misses O had deftly opened my pants and was pulling them and my underwear down enough at the back to expose my buttocks. As the realization of her intentions dawned on me Misses O’s pointer was already swishing through the air to lash my exposed buttocks. I lurched forward shrieking with pain tumbling awkwardly off the chair.

Missus O let me writhe in agony at her feet as I clutched my stinging ass cheeks with my still burning hands. Eventually Missus O drawled unsympathetically, “Oh do get up David and assume your position on the chair so I can finish.” Slowly, hesitantly I rose from the floor. With a sense of shame I tried to pull up my pants but stopped when Missus O cleared her throat threateningly. I looked pleadingly towards her only to be crushed by the implacable harsh glare of her eyes. Meekly I crawled back onto the hard chair to assume my position partially relieved that at least my shameful erection was gone.

Missus O tapped me here and there with her pointer until she had me arranged properly. Wedging her pointer into the crack of my ass she commanded, “Squeeze.” Automatically I did my stinging butt cheeks holding the nasty pointer in place. Eying me closely Missus O smirked before returning to her desk and paperwork.

While I knelt there trying to figure out how this had happened to me Missus O hummed away seemingly oblivious. When the door to the classroom opened abruptly I let out a startled gasp frozen to my spot on the chair. Filling the doorway was the school custodian Mr Jones. He was a large man dressed in laborers greens and I stared at him in horror. He appeared to be completely nonplussed by the sight of a student kneeling on a chair with their buttocks exposed while their teacher sat at her desk marking papers.

His voice seemed to boom as he asked with deference, “Would you like me to come back later Missus O’Callahan?”

Beaming Missus O responded gaily, “Oh no Mr Jones please continue.” The large man nodded his head in acknowledgement entering the room pulling a trolley behind him. Hanging my head in shame I didn’t dare look in his direction as he performed his menial tasks. He worked around both Missus O and myself nonchalantly as if nothing was amiss until he was sweeping around my chair. He stopped, I could feel his eyes upon me and I could smell the rawness of his body odor.

My body started to tremble uncontrollably again and I was startled when his voice boomed, “You need any help here Missus O’Callahan?”

There was an extended pause where my mind went blank with fear as we waited for Missus O’s response. Relief flooded through me when she casually announced, “Oh not today Mr Jones.” I sucked in deep breathes to calm myself only to I freeze once more when Missus O continued pleasantly with, “But I may very well require your assistance in the future.” The large man grunted something incomprehensible and was soon gone.

With out rising Missus O hissed, “Get out,” at me. Uncertain I cast a despairing look at her. Her cold glare cowed me before with a arch of her eyebrow she murmured darkly, “Best hurry David before I call Mr Jones back.”

I scrambled off the chair to comply sending the pointer clattering to the floor. I am sure it must have been comical to watch as I fumbled about trying picking it up while also trying to hold my pants from dropping to the floor. After retrieving the pointer I didn’t know what to do with and in a fluster dropped it on the chair then hurriedly got my pants done up, grabbed my books and scurried from the room.

When I looked back Missus O had returned to her paperwork as if nothing had occurred and I had never been there. I rushed into the hall so intent on getting away that it wasn’t until I was nearly home that I began to register the pain emanating from hands and buttocks. Stopping I looked over my shoulder and shivered over the thought of what a painful experience Missus O’s detentions were possibly going be. And I had an erection again. That night my masturbation fantasies took a dark and disturbing turn towards humiliation and pain.

Day two of my detention.

That I was keen, almost eager, to attend my detention was slightly confusing for me because though I was excited to be the focus of Missus O’s attentions I was also very fearful of her use of her pointer. When I entered her classroom she was busily marking papers and while barely acknowledging my presence indicated my desk with a flick of her hand. Dutifully I took my seat, sitting straight backed, books under the desk and my hands on the desk in front of me. At the front of the classroom stood the straight backed wooden chair with Missus O’s pointer resting on it. I swallowed down a mixture of excitement and fear.

Though I was ostensibly staring straight ahead I scrutinized Missus O out of the corner of my eyes. She had an allure that I was unable to comprehend. Though my hands had still ached when I got home the previous afternoon I had stroked myself to a mind numbing orgasm, possibly the most intense one of my young life. For reasons I couldn’t explain the sight of the two red lines criss-crossing my buttocks and the memory of how they got there returned my cock to an erect state allowing me to climax again. I would probably have gone a third round if my mothers call for dinner hadn’t disturbed me.

Now I sat there before Missus O fantasizing about what she was wearing beneath her clothes, what punishment she was going to mete out today and willing my cock not to harden noticeably. I was jolted out of my perverse reverie by a curt demand of, “Assignment David.” When I could focus I saw that Missus O was holding out her hand but not looking at me. Tentatively I retrieved my assignment, rose and placed it carefully in Missus O’s hand. When she didn’t even look at me I stood there feeling foolish before returning to my seat confused.

After a cursory look at my work Missus O dumped the paper into her trash can. Instinctively I let out a small gasp of dismay but quickly stifled myself when Missus O cast a cold and uncompromising glare on me. She didn’t say a word but there was no doubt in her demeanor that she was not in the mood to humor me. I swallowed hard, bowed my head and looked away. Missus O’s snort of derision made me flush red shamefully and sink lower into my seat worrying about what Missus O wanted from me.

I sat in silence listening to the shuffling of papers, the occasional muttered comment and scratch of Missus O’s pen as she continued on with her marking oblivious to my presence. After about a half hour my butt ached and I started to fidget. It wasn’t much but almost immediately Missus O stopped her marking. In the dead silence I dared to look in her direction and felt myself shrink beneath the harsh contemptuous glare in Missus O’s eyes. Missus O held my gaze until I meekly looked away. After a moment the noises of her paper marking restarted and a shiver of relief trembled through me.

I remained seated perfectly still even when Mr Jones the custodian entered the room. Missus O and he exchanged pleasantries while I was totally ignored. Mr Jones performed his custodial duties before exchanging further banal pleasantries with Missus O and departed. I sat there trying not to move.

Despite the discomfort of the hard desk seat and the aching of my butt I slipped into an uncomfortable trance like daze. It took a moment for me to realize what was happening when Missus O abruptly stood and gathering up her things dismissed me with a curt, “Very well David, you can go.” Somewhat dumbfounded I rose but couldn’t quite figure out where I should go. Exasperated Missus O snapped, “Go home David. I will see you back here again tomorrow.” Dismissed I headed for the door, as I was leaving I looked back at Missus O and was surprised to see her watching me with a devious smirk on her face.

Confused I scurried home to try and turn my recent detention experience into an erection and orgasm. I managed to get myself excited and I brought myself to climax but was sorely disappointed with the result after the pleasure the day before. When I thought of my earlier detention, my humiliation at Missus O’s hands and painful shock of her punishments my cock surged. Mesmerized by the sight of it I slowly stroked myself to an orgasm that eclipsed yesterdays in intensity and the resulting pleasure. Spent I was almost too sexually exhausted to deal with my cock when it swelled to an erection again. Fantasizing about Missus O and my next detention I rubbed my cock raw again and again, and again.

Day three of my detention.

Sheepishly I crept into Missus O’s classroom certain that she would somehow know of my after detention activities as my masturbation sensitive cock was stirring in my jeans reminded me of my perversion. Missus O ignored me as she had the day before. Perplexed by my sense of disappointment I slipped quietly into my desk. Without looking at me Missus O snapped her fingers then holding out her hand obviously demanding my detention assignment.

Fumbling and uncertain I abjectly complied. Missus O didn’t even bother looking at my assignment before unceremoniously dumping into her trash can. Before I could react and still not looking at me Missus O spoke, her voice lacked any emotion as she intoned, “On the chair David.”

My eyes widened as a surge of excitement rushed through me. Breathing hard to maintain my composure I dutifully mounted the chair making certain that I assumed the position that had been dictated to me previously. Missus O let me kneel on the chair long enough for me to become uncertain as to what her intentions would be. Though tempted to look and see what she was doing I managed to control my curiosity not daring to peek.

Finally I heard her chair scrape across the floor then the click of her heals as she paced around me. Coming up behind me Missus O lent into me whispering dramatically in my ear, “Don’t move David.” My body went weak as her whispered command rippled through me. While I processed her words Missus looped a wide red ribbon over my head covering my eyes tying it tightly behind my head. When I instinctively started Missus O’s murmured, “David.” Taking a trembling breath I calmed myself allowing her to finish tying her knot.

The ribbon didn’t totally block out the light and I could sort of make out Missus O’s shape as she used more ribbon to tie my wrists to the chair. As she tied off my right wrist I tested the left one earning another murmured, “David.” While I concentrated on breathing and the growing erection in my pants Missus O opened them. I marveled that she either didn’t realize I had an erection or choose to ignore it as she pulled my pants down at the back to expose my buttocks again.

Missus O then placed her wooden pointer in the palms of my upturned hands murmuring quietly, “Do not drop this David.” With my wrists were securely tied off to the chair I dutifully gripped her pointer like good boy. Missus O checked her knots before pulling my hips back making my bottom stick out more. I couldn’t help flinching and then moaning as Missus O drew her finger nails over my exposed butt cheeks. I could almost feel her smile and moaned louder as she lightly traced my lips with the fingers on her other hand.

The blind fold seemed to make my skin hyper sensitive to Missus O’s fingers and her nails gently raking over the bared flesh of my protruding buttocks. My body trembled and shook as her fingers played over me. When Missus O pressed a finger against my lips and breathed against my neck, “Suck on it.” I moaned louder before sucking the tip of her fore finger into my mouth. “That’s a good boy David,” Missus O sighed breathlessly in my ear, “Suck harder.” And I did. Missus O began pulling her finger back to my lips before allowing me to suck back into my mouth. Soon her finger was slick with my spit and she added another. As I sucked both fingers in Missus pressed down forcing them in deeper, then pulled back before forcing them in again moaning, “Suck David.”

While Missus O’s fingers slipped in and out of my mouth her other hand continued to stroke my bare buttocks and with each pass of her nails she pressed harder into the creamy flesh. “Suck David,” Missus O encouraged me, purring, “be my good boy.” While I sucked enthusiastically on her fingers Missus O’s other hand stopped stroking and her nails began to dig into my bare buttocks. At first it was just a distraction but soon began to hurt and when the pain increased sharply I cried out around the fingers Missus O had filling my mouth.

Missus O’s finger nails were digging deeply into my butt cheek when fingers disappeared from my mouth. I tossed my head back wanting to cry out from the pain when something soft and rubbery was pressed against my lips. My first instinct was to pull away but as if sensing my move Missus O murmured quietly but authoritatively, “Suck on it David.” I hesitated for a moment then sucked the rubber thing into my mouth. As I did Missus O’s finger nails released my buttocks ending the pain they were inflicting on my butt cheek. I could feel the marks her nails had left behind as I sucked to keep the bulbous rubber object between my lips.

While I sucked Missus O’s saliva wet fingers slid over my bare butt. It was a weird sensation and I would have been more concerned about them if I hadn’t at that moment noticed that from beneath the ribbon covering my eyes I could make out what seemed like Missus O’s hand slipping beneath the hem of her skirt. I stopped sucking as I tried to make out more while being vaguely aware that Missus O’s other fingers has slipped between my butt cheeks and were gently stroking me there.

I was nearly panting as I watched transfixed while Missus O’s hand rotated around under her skirt seeming to press against herself again and again. Not even aware of it I was sucking on the rubber thing in my mouth again. Though I felt Missus O’s saliva slick fingers playing over my anus I was too fascinated by her intriguing activity to care. Missus O gasped audibly and her body pressed heavily into mine. While she lent against me Missus O’s fingers began to pulse against my anus. Just as I was starting to worry about what she was doing her other hand emerged from beneath her skirt and she used it to start tracing my lips bulging around the rubber thing I was sucking on. Her fingers were moist and the smell from them was intoxicating.

“Yes David,” she whispered, “suck like a good boy.” Thrilled by her encouragement I did as she demanded while she traced my nostrils with musky scented fingers. While Missus O distracted me with her one hand the fingers on her other continued to gently probe my anus. With my senses overwhelmed with the scent of her I moaned over the rubber thing when Missus O’s finger popped inside me. A shiver of rippled through my body as I gave myself up to this woman.

I didn’t know what she had done when I felt the hot wetness dribble between my butt cheeks to slither down to Missus O’s fingers caressing my anus. She had drooled her spittle into to my butt crack to help lubricate her assault on my ass. I couldn’t have cared less, the scent of her on my lips with the sensation of her finger slowly pumping in and out of my anus caused my erection to press painfully into my constricting clothes. All I could think of was how wonderful it would be if i could get a hand free to touch myself or even better, if Missus O touched my erection for me.

Enthralled I sucked harder trying to hold the rubber thing in my mouth when Missus O’s fingers attempted to pull it out. Chuckling Missus O teased, “Oooh David so eager.” Then pulling the bulbous rubber thing from my mouth. I gasped as at the same time Missus O thrust the finger of her other hand deep into my ass. Startled by the sensation of being penetrated I pressed my head against the back of the chair pushing my bottom out to meet her finger. Then there were two. While I moaned Missus O worked her fingers in and out of my ass.

Missus O’s fingers vanished from my anus only to be promptly replaced by slick rubber thing that had been in my mouth. I moaned louder as Missus O pressed the thing against my anus until her scented fingers found my mouth and she forced them in silencing me. Immediately I started sucking hungrily on Missus O’s fingers tasting her scent on them. My back arched and a shiver of excitement wracked my body as the bulbous head of the rubber thing slipped into my ass. I moaned loudly over Missus O’s fingers and my body twitched and jerked as my erection exploded cum into my pants.

While my body convulsed with orgasmic spasms Missus O alternated between pumping her fingers against the rubber thing in my butt and delivering sharp stinging barehanded smacks to my butt cheeks all the while cajoling me with, “Do you like that David? Hmm.” But Missus O kept her other fingers deep in my mouth obviously not wanting or needing an answer.

“Do you like that?” Smack. “Huh little boy, do you like that?” Smack.

When I was whining with distress over her fingers Missus O whispered in my ear, “You’re going to be a good little boy aren’t you David?” Smack. “You’re going to be a good little boy for me aren’t you David?” Missus O purred snuggling her nose into my neck while her hand slipped deep into the back of my jeans and her fingers enclosed around my cum slick balls.

When she squeezed my balls playfully I whimpered so she squeezed them again harder digging her nails in threateningly. Squealing more with fear than pain I was relieved when she let go pulling her hand free and smacked my bare cheek again. Without warning her one hand left my mouth and the other one quickly substituted it. The taste was noticeably different and it took me a moment to realize that I was sucking my own cum off of Missus O’s fingers. When I stopped Missus O pressed her fingers into my mouth until I gagged and only relented when I started sucking again.

Missus O purred, “That’s it my good little boy suck my fingers.” While I did I realized that Missus O’s other hand was beneath the hem of her skirt again. “Enjoy the taste David,” she encouraged me before chuckling meanly, “you’re going to be tasting it a lot from now on.” I mewed pathetically around the fingers in my mouth not really sure what she meant but thinking that I wasn’t all too sure that I would enjoy it. Missus O groaned loudly beside before collapsing against my body again.

With a long shuddering breath Missus O rose off me pulling her fingers from my mouth. All business she released the ribbons binding my wrists to the chair and pulled off my blindfold. With a playful slap to my butt cheek Missus O told me, “Pull yourself together David. You can leave.”

With my dismissal Missus O went to her desk and started ignoring me again. Dumbfounded I somehow managed to pull my pants back up and gather my books. Casting an inquiring look at Missus O that wasn’t returned I headed for the door only to freeze when Missus O’s voice called out, “Oh David,” when I turned Missus O was beaming at me thoroughly amused. Chuckling she was pointing at the crotch of my jeans laughing, “You may wish to do something about that before you head home.”

To my horror the massive orgasm that I had experienced had left a large wet spot at the front of my jeans. Flushing red with humiliation I went to flee Missus O’s classroom only to pile directly into Mr Jones the custodian. Pushing me away the large man sent me sprawling across the floor.

My books lay scattered about me as Mr Jones loomed over me inquiring quietly, “Is there a problem here Missus O’Callahan?”

To the sounds of Missus O’s humiliating laughter echoing about the room and beneath the look of distaste on the large mans face I shook my head frantically no. Mr Jones seemed threateningly large as Missus O chuckled, “Oh no Mr Jones, the boy was just leaving.”

Standing over Mr Jones pointed at the wet spot spreading across the front of my jeans snorting with disgust, “The boy seems to have a problem there.” I was horrified that he had noticed my humiliating spot then dismayed when both he and Missus O burst into uncontrolled laughter.

When I could finally scramble to my feet I fled the room with their laughter ringing in my ears. Using my books to cover the ‘spot’ I rushed home praying that no one would see me. As I rushed along I became aware that the rubber thing was still in my ass. Stopping I worried about what to do about it but couldn’t think of anything so trying to ignore its presence in my butt I scurried the rest of the way home. When I got there I snuck in and up to my room to strip off my pants and underwear. My underwear was soaked from my orgasm and as I stood there naked from the waist down I felt my anus clinch around the rubber thing while surprisingly aware that my cock was engorging.

I spent the rest of the afternoon masturbating uncontrollably until it hurt to touch my cock. I was amazed that every time I ejaculated my anus would pulse around the rubber thing in time to each jet of cum spraying from my cock. Afterwards as I recovered my anus would continue clenching and unclenching the rubber thing invading it arousing me once more. Eventually I managed to remove it groaning as my body convulsed with sensations I didn’t understand. The experience left me breathless and stunned.

Day four of my detention

The next morning I awoke with a start from a feverish dream. Before I could recall it the dream slipped away leaving me disorientated and trembling. Closing my eyes I tried to bring the dream back but failed. As the effects of the dream faded I noticed that my cock was painfully erect and tender to the touch. Sighing with frustration I rolled onto my side and felt my anus clinch numbly. Oh god I moaned into my pillow pondering how I could face another day when my mothers voice compelled me to get up and get on with it.

I spent the day in something of a stupor. As the day progressed even my usual protagonists eventually relented and mostly just left me alone. I sat through Missus O’s English class like a zombie only taking notice of what was going on when she reminded me sternly that I had a detention with her after school. Dumbly I acknowledged her before shuffling away.

Filled with trepidation I returned to Missus O’s classroom for my fourth detention. It took all my will power to force myself through the door and into her presence. Missus O was standing in front of the hard wooden chair as I entered looking stern and implacable. Tersely she informed me, “On the chair David.” I hesitated torn between complying and fleeing. When Missus O cajoled me in a quiet calm tone, “Now David.” My will broke and I complied.

Once I had assumed the kneeling position Missus O required of me she deftly bound my wrists to the chair with her ribbons before slipping another ribbon over my eyes. Bound and with eyes covered I lost control and started to simper into tears. Ignoring my emotional outburst Missus O quickly opened my jeans pulling them down with my underwear. I gasped in shock as this time she not only exposed my buttocks but genitals too.

I distinctly heard Missus O humming as she promptly proceeded with exploring my exposed flesh with her finger nails. Her touch was light but insistent and when she grazed her nails over my engorging cock I groaned loudly and arched my back as a spasm wracked my body. Missus O purred in my ear as she continued to gently stroke my raw cock drawing more spasms from me. I was gasping for breath as my sore now erect cock was played with.

Missus O slipped away from my ear and I was aware of her sinking to the floor. Slowly but surely Missus O’s fingers enveloped my raw raging cock and began to stroke me. Each pump of her hand flooded my senses with electric sensations of lust combined with the stinging pain of tortured flesh. When Missus O’s lips closed over the tip of my erection I exploded. Fireworks of light flashed across my blindfolded eyes as my body shook and shuddered as I screamed soundlessly from the intense pleasure and pain of the experience.

By the time I regained some of my senses I was aware that Missus O was kissing me. Passionately kissing me. Her hands held my head and her tongue was swirling wetly about in my mouth. After kissing for what seemed like forever Missus O pulled away. While I swooned Missus O started tracing my lips with another rubber object. My lips and mouth were coated with a slick filmy coating that lubricated the rubber thing as she caressed my lips with it. Relentlessly Missus O then began to press her rubber thing into my mouth and I willing parted my lips to accept it, sucking it into my mouth for her. It was different from yesterdays, still bulbous but fatter, bigger.

While I sucked on it I heard Missus O intone, “Count for me David.” With the large bulbous rubber thing firmly between my lips I heard the whistling swish before the stinging impact of Missus O’s pointer biting into my bared buttocks. Though I screamed the rubber thing worked perfectly as a muffling gag and Missus O stroked my buttocks again with her wooden pointer calling out amused, “Are you counting David?” Before lashing my butt cheeks mercilessly with ten vicious strokes. I screamed again and again sobbing from the searing pain

When she had finally stopped I heard her chuckle, “That should distract him for a while.” And while I wondered why I heard a grunt, a very manly grunt. Though I couldn’t stop simpering because of the white hot welts crisscrossing my buttocks I felt a deep sense of shame washing over my body knowing that another person knew of and had probably witnessed my debasement. I wasn’t sure because of the blindfold but I suspected that Mr Jones the custodian was that person.

I heard Missus O chuckle playfully as I could vaguely make out two shapes that were soon one. While I sucked forlornly on Missus O’s rubber thing I listened to the two of them moan and groan their passion. While I sucked desk legs scraped and chairs crashed over while the noise of their passion increased. I could feel my cock responding to the action I could barely see and the sounds I couldn’t completely understand. The shapes seemed to crash over a desk and though I had no way to be sure it was followed by an extended bout of grunting before the man growled loudly and Missus O keened in response. Then silence.

Abruptly one shape rose and there was a flurry of activity followed by the loud slap of a bare hand on bare flesh and a female squeal of pain or delight or maybe both. A shape suddenly loomed over me and I quaked with fear. I knew by the size and the hoarse breathing that it was the man and probably Mr Jones. Terrified I sucked on the rubber thing for comfort until he yanked it from my mouth. With no warning the man dug rough fingers into my welted butt cheek pulling on it harshly to expose my anus. Unceremoniously he pressed Missus O’s slick rubber thing against my anus while I moaned from the shock and discomfort. When I instinctively clenched my butt pulling away the man landed a harsh hard open handed smack to my bare butt cheek.

The smack was so unexpected and so painful on my already well welted butt cheek that it took my breath away. While I moaned with agony he landed another smack on my other cheek that made me choke on my pain before sobbing uncontrollably. When his nails dug into my butt cheek again I whimpered allowing him to spread me wide. With determined force the man pressed the rubber thing against my anus until he forced it in. The sensation of being impaled stopped my sobbing as my body convulsed and shook with spasms. The rubber thing felt so large and my anus felt so full that I barely noticed when the man delivered two more loud smacks to my butt cheeks.

While my anus clenched and spasmed around the rubber thing I moaned my distress until I realized that the man was rubbing something fleshy over my lips that was slick with goo. When I tried to pull away he gripped my hair firmly with one hand and used his other to brush his slick flesh against my lips. I knew it was his cock but I didn’t want to know it was his cock. And even though it tasted vaguely like Missus O’s fingers I certainly didn’t want it in my mouth. He had other plans.

He stopped rubbing himself against my lips long enough to deliver a painful slap. Holding my head by the hair he shook my head snarling, “Open your mouth boy.” with a whimpering sob I complied and when I felt his gooey flesh brush against my lips I choked back another sob of utter shame sucking his flesh into my mouth. The man groaned above me pushing his hips forward offering me more of his goo slick flesh. I sucked the mans soft flesh into my mouth smelling his sex, tasting him and Missus O.

The mans firm grip on my hair held me still while he started to rock his hips back and forth pulling his flesh in and out of my mouth. As I grew used to the rhythm I would suck harder when he rocked forward while puckering my lips when he pulled away. It wasn’t long before I felt his flesh swell and harden. The man kept up his slow methodical rhythm until his flesh seemed massive between my lips and pressed into my throat when he rocked his body forward. Then suddenly it was gone. With a grunt of disgust the man announced loudly, “Won’t be wasting this on you boy.”

His hand was gone from my hair and the man had turned on Missus O again. I heard him growl, “Over the desk bitch.” Followed by loud scraping and what may have been ripping clothes. The man snarled, “Spread your cheeks for me you fucking whore.” There was a feminine whimper in response followed by a loud fleshy smack and the man snarling, “Shut the fuck up and take it.” There were several more loud smacks and a quiet female mewing.

The man was grunting in unison with the scraping of desk legs as I tried to make out what the shapes were doing. There was an angry roar and more smacked flesh to the sound of Missus O mewing keenly. Then it was over, the man rose and suddenly was gone. I watched the shape that was Missus O rise and move towards me.

Untying my wrists Missus O pushed me to the floor. I had no will power left and just lay there. Missus O sat on the chair before me reaching down to pull me up bodily by the hair. I whimpered mutely as she pulled my head between her spread thighs. I could feel the silky smoothness of her nylons and smell her sex as she drew my face towards her. I had never seen a woman’s naked pussy before and all the ones I had seen in magazines had been hairy. It came as a complete surprise when Missus O pressed my face between her thighs into hot moist bare flesh. Missus O used her grip on my hair to rub my face back and forth over her wet fleshy womanhood coating it with the mixture of hers and the man’s secretions.

Missus O was purring contentedly as she used my face to massage herself with. I was dumbfounded as to what she was doing and was mildly repulsed by the gooey mess between her thighs. Holding my face pressed against her womanhood Missus O murmured, “Lick me David.” When I tentatively flicked my tongue out and tasted the goo coating her flesh Missus O moaned, “Lick me harder David.” When I stuck out my tongue to lick her Missus O thrust her hips up to meet it. “Yessss,” she groaned wantonly, “That’s my good little boy, lick me. Lick me good David.”

Unsure of what I was doing I licked Missus O’s moist flesh swirling my tongue around in the goo. After licking her for a while the taste became less repugnant and the sounds Missus O made let me know she was enjoying my swirling tongue encouraging me to apply myself. While I licked Missus O she would raise and lower her hips directing my probing tongue where she wanted it most. Amongst the folds of her flesh my tongue found the entrance to her womanhood and Missus O’s hold on my hair tightened as she pulled my face into her crying out, “Yes David, lick me there.” And despite the copious amounts of wet goo I did while Missus O ground my face into her flesh. “Suck me David,” I heard Missus O cry out as her thighs squeezed around my head tightly and her moist flesh enveloped my face.

Missus O humped herself against my face squeezing tighter with her thighs while I tried to suck and lick her. I was being smothered in her moist hot flesh and it seemed like I was drowning when I felt Missus O’s body go rigid. I thought her thighs were going to crush my head or I was going to suffocate until suddenly her legs fell apart allowing me to breathe. I gasped for breath trying to see more through my blindfold. With every breath I smelt and tasted Missus O and whoever the man had been.

Missus sat panting in the chair still holding on loosely to my hair. As her breathing became more controlled her grip tightened and she was pulling my head back between her thighs. As my face neared her bare flesh Missus O whispered, “Lick me David.” With a deep breath I stuck out my tongue until I felt her flesh and began licking her like a puppy. “That’s it David. That’s better.” Missus O cooed above me, “Swirl your tongue around there David.” When I swirled my tongue around what seemed to be a hard nub of flesh she gasped calling out, “Suck me David suck me.” So I did, trying to suck Missus O’s fleshy nub into my mouth. Her hand ripped at my hair as she encouraged me to, “Suck gently David, gently.” I sucked on her like I was kissing her deeply, my tongue darting out tasting her.

Missus O hummed with pleasure while slowly sliding herself forward on the seat. Pushing on my head she forced me to kiss and lick her deeper between her legs. Slowly purposefully she forced my head down until my mouth was over what I was certain was her ass. She stopped me there pulling me into her. My nose was buried in the wet folds of her womanhood and my mouth was over her anus. I balked at licking her there.

When Missus O called out breathlessly, “Lick me David.” I couldn’t do it. Timidly I gave what must certainly be her anus a quick peck with my lips surprised and disgusted at how wet she was there.

Above me Missus O’s voice hardened, scolding me, “Lick me David.” When still I hesitated, her hand tugged on my hair and she repeated her demand, “Lick me David.” I didn’t, I couldn’t. Before I knew it she had pulled my face from between her thighs. I couldn’t she her face but her voice dripped with fury as she snarled, “When I tell you to lick me boy,” on ‘boy’ Missus O’s hand slapped me hard across the face and my face stung with a red hand print as she finished with, “you lick!” Missus O slapped me again.

I heard her spit before I felt the warm fluid hit my face. Shaking my head by my hair Missus slapped me again. I couldn’t see the slaps coming so they seemed to hurt so much more and I felt so humiliated as her spittle drooled down my face. Then slap. Spit. Slap. Missus O was breathing heavily into my face as I simpered in her grip fearing more abuse. Missus O eased herself back onto the chair pulling my head with her hand and forcing my face back between her thighs.

With my face planted firmly against her womanhood and my mouth over her anus Missus O asked me calmly to, “Lick me David.” Though disgusted with the thought of licking around any ones ass I did as she asked. Her anus was oozing fluid very much like the goo from her womanhood only funkier. “Yes David,” Missus O moaned, “Lick me good.” Dutifully with my face burning red I performed the horrid task.

With another deep moan Missus O sighed, “Kiss me David.” Though reviled I planted my lips over her anus and kissed her there. “Suck me David,” Missus O groaned but when I did a flood of the gooey fluid gushed from her anus. Horrified and ignoring her grip on my hair I pulled away. Missus O furiously pulled my head away and sitting up slapped she me. Repeatedly. I was too shocked and disgusted to even cry as Missus O vented her fury on my face.

When she finally stopped my face was on fire, and snot dribbled from my nose as silent tears trickled down my cheeks. “Open your mouth,” Missus O snarled. Meekly I complied. “Wider,” she hissed and when I stretched my mouth as wide open as possible Missus O spat in it. My initial reaction was to cough it back out but Missus O snarled, “Don’t you dare,” as her grip on my hair tightened.

I froze, violated, sickened. “Stick out your tongue,” Missus O demanded. Feeling fully defeated and used I did as she asked. “Make it stiff,” she sneered cruelly. When I tried she flicked my tongue with her finger sneering in my face, “Stiffer.” I tried to. Missus O flicked it again and I whimpered with pain and humiliation. “Good enough,” she continued sneering, “Now keep it stiff.”

With me straining to keep my tongue as stiff as possible Missus O guided my face back between her legs. I wanted to pull away but my well slapped face told me not to dare. Missus O guided my stiff tongue until it was touching her anus. I could feel that the wet goo was still there with my stiff tongue and tried not to think about what was going to happen next. Holding my head firmly still Missus O forced my stiff tongue into her anus. As my tongue entered her ass my nose entered her womanhood and Missus O sighed contentedly.

Hoping that that would be it I choked back my gag reflex when Missus O purred, “Stiffer David.” I strained to make my tongue stiffer for her while she pushed herself against my face. “Stiffer David,” Missus O panted as she began to hump my straining tongue and my nose buried in her womanhood. The goo still oozed from Missus O’s anus coating my tongue as I started to struggle to breathe. Above me Missus O cooed, “Stiffer David. Deeper David.” I couldn’t help whimpering my distress.

There was a moment of relief when a distracted Missus O pulled my face away. But it was short lived when she promptly slapped me sneering, “You’re just not trying are you David.” Whimpering and sniveling I endured several more stinging slaps that had me weeping. “Oh stop simpering like a sissy David,” Missus O sneered with contempt. Without releasing my hair Missus O spun around placing one knee on the chair. Leaning forward she hissed, “Stick your tongue out David.” Resignedly I did as I was told knowing that soon it would probably be pushing back into Missus O’s gooey ass.

She didn’t disappoint me. Missus O forced my face between her butt cheeks. When Missus O had my tongue in contact with her anus she started bouncing her buttocks on my face thrusting my tongue into her. “Stiffer David,” Missus O demanded. Soon she was panting, seeming to enjoy my tongue when she stopped. Grinding her hips down she pushed her anus against my tongue before purring, “Kiss me David.” Relieved that I could give my tongue a break, I dutifully planted a kiss to the area of Missus O’s anus.

Tsck tscking Missus O pressed me good naturedly, “Now now David give us a real kiss.” Fearing her retribution I pushed between her butt cheeks and planted a long almost passionate kiss to her anus. Missus O cooed with delight purring, “That’s the way David kiss me again.” Forlornly I pressed my lips against Missus O’s moist anus. While I was kissing her Missus O cooed, “Tongue me David.”

I almost hesitated but utterly beaten I gently probed Missus O’s anus with my tongue. “Oooh yessss,” Missus O cooed, “yes David tongue me good.” Slowly her hips started to rotate gently grinding her ass over my face and her anus onto my tongue. Missus O’s free hand slipped between her legs and I could feel her massaging herself.

I didn’t want to hear her when she gurgled, “Suck me David.” With a whimper of submission I pursed my lips over Missus O’s anus and sucked. She moaned loudly crying out, “Your tongue David, give me your tongue.” Completely subdued, I pressed my tongue as far into her gooey anus as I could while her hips continued to gyrate over my face.

“NOW SUCK,” Missus O cried and submissively I did. A stream of gooey discharge flooded into my mouth. Wanting to pull away the best I could do was purse my lips allowing the gooey flood to run down my chin. Missus O took deep breaths finally pushing me away. Sitting on the floor at the front of the classroom in semi darkness I waited for Missus O’s instructions. I could hear her rummaging around but had no idea what she was doing.

Finally she pulled the blindfold away from my eyes telling me distractedly, “Get up David and get yourself together.” When I could only sit there bemused blinking in the bright light Missus O kicked me with the toe of her heel snarling with exasperation. “Get yourself together David.”

It was easier said than done. Fumbling with my clothes I struggled to pull up my underwear and jeans. I felt dazed as I wiped a hand over my bruised lips appalled to see the gooey mess it wiped away. Missus O had no time for my befuddlement and handing me my books propelled me towards the door. It took me a few paces before I figured out that the large rubber thing stuffed into my anus was forcing me to take mincing steps. Stopping I felt limply for my anus and the rubber thing buried deeply there.

Missus O’s voice sounded almost kind as she told me, “Go home David.” Looking at her I was in awe of how radiant she looked. I wasn’t entirely sure what had happened during my detention but Missus O clearly thrived on it.

With a wry Cheshire Cat smile Missus O cajoled me, “Go home David.” Tearing myself away from her gaze I turned for the door. Taking shuffling steps that accentuated the rubber things presence I walked away in a daze. While I walked away I continued wiping at the fluids drying on my face. The rubber thing was forcing me to sway my hips as I walked and I could feel the welts raised on my buttocks by Missus O’s pointer chaffing against my clothes.

Fully distracted I was shocked to see the hallway in front of me blocked by the looming mass of the custodian Mr Jones. Stopping short my body started to quake uncontrollably with emotions I couldn’t explain. Mr Jones was watching me like I was prey and when I whimpered audibly an evil smile spread across his hard face. It felt like the floor was going to open up and swallow me as he continued to block my way. With a grunt of contempt Mr Jones pushed his cart towards me smirking as I cowered against the wall.

Stopping beside me Mr Jones loomed over me once more and I mewed with fear of his overwhelming presence. While I tried to blend into the wall Mr Jones’ smirk turned to amusement as I felt a hot wetness flood down my pants leg. Laughing heartily at my lack of control Mr Jones sauntered away as I stood gaping horrified at the wet stain down the leg of jeans. Consumed with shame of having just pissed myself I fled terrified that anyone would see me.

Somehow I managed to make it home and to my room undiscovered. Stripping off my soiled clothes I dithered, looking in the mirror on my door I was awed by the red welts criss-crossing my buttocks. Reaching behind me I trailed my finger tips gently over the still sensitive raised flesh. When my fingers brushed over the rubber thing stuffed in me my ass clinched and spasmed sending a shudder through my body. When I pushed against the base of the rubber thing it was like an electric shock rippling through me. My knees buckled and I sank slowly to the floor. My fingers pumped against the rubber thing and I watched transfixed as my cock swelled to a painful erection.

It hurt to touch my erection. It was agonizing to stroke it. But my fingers kept pumping against the rubber thing wantonly stuffing it deeper into ass helping me to ignore the pain and stroke my cock furiously. When cum sprayed from the tip I had to bite my lip to stifle my cry of utter ecstasy. It took a long time to recover. I was vaguely aware that at any moment I could be discovered but didn’t possess the energy to care. Eventually I dragged myself from my sex induced stupor to begin to pull myself together. Removing the rubber thing from my anus was more difficult than the previous one and when I finally managed I was left trembling while my anus pulsed numbly.

Detention Day 5

I was late. Missus O didn’t look up from her paperwork when I rushed into her classroom to stand before her desk. She ignored me. Hanging my head in resignation I stood there nervously waiting, unsure if I was in bigger trouble or not. It wasn’t soothing that the chair and pointer were again already in position at the front of the room. While I was pondering the possibilities Missus O cleared her throat to get my attention. When I looked up she was looking me over with a cold calculating glare, “You are late David,” Missus O announced with an off handed manner.

I tried to mumble some sort of excuse until her hand flashed up to stop me. “You’re assignment David,” Missus O requested, holding her hand out for it. Fumbling I dropped one of my books trying to extract my paper to give to her. When I was finally able to offer it to her it was too late, her hand was gone and she was looking away uninterested. In a flat monotone Missus O told me, “Just put it on my desk David.”

My hand trembled as I complied. Missus O ignored me for a while before disinterestedly picking up my assignment. She quickly scanned the cover page before abruptly ripping the document in half and tossing it into the bin. While I stood there dumbfounded Missus O informed me, “You have an extra day added to your detention David for being tardy.” Missus O bestowed a thoughtful look upon me seeming to dare me to speak before continuing, “You will repeat that assignment David and hand it in on Monday.” Withering before her I simply nodded my head in agreement as it slumped between my sagging shoulders.

“Right,” Missus O barked making me jump, “on the chair David. You know the position.”

Sheepishly I complied. Kneeling on the chair placing my hands palm up across the back unhappily contemplating the pain coming. Missus O rose from her desk and without ceremony marched over to stand beside me. With a calm calculated movement Missus O took up her wooden pointer. I couldn’t help flinching when she swung her pointer swishing through the air several times for practice.

“Well David,” Missus O purred, “which is it to be.” When I couldn’t bring myself to respond immediately she playfully tapped her pointer on my buttocks seeming to enjoy my uncontrolled flinch in response, “There David,” Missus O cooed seductively before resting her pointer on my upturned palms, “or here.”

Somehow I managed to mumble semi coherently, “My bottom please Miss.”

Missus O cackled in response mocking me with, “Oh little Davie would like to have his bottom stroked would he.” Flushing red with embarrassment I cringed before her mute until she lashed my buttocks with her pointer snarling, “Well does he?”

The unexpected lash of the pointer made me lurch and lose my balance. Trying to save myself from tumbling from the chair I wasn’t thinking when I cursed, “Fuck.” As soon as I said it I froze. The room seemed to be deadly silent. I could hear Missus O tapping her pointer gently against the side of her leg as I prayed that she hadn’t heard me. But she had. Her voice devoid of emotion Missus O inquired softly, “What did you say David?”

I couldn’t respond. I could only hang my head in shame knowing that I was now in greater trouble than before. Missus O let me flounder in my shame and I didn’t even dare to look up when the door to the classroom opened. In a fog I heard Missus O speak with the custodian Mr Jones. He was asking politely if everything was alright and if she needed his help.

After a thoughtful moment Missus O asked the man if he had any bars of soap on his custodians cart. Glad to be helpful Mr Jones replied that indeed he did and produced a bar for her. Missus O made a great show of removing the paper wrapper as she paced slowly around me. Stopping before my chair she requested politely, “Look at me David.” Slowly, resigned, I complied. “Open your mouth David,” she continued in a pleasant voice.

Unwillingly I parted my lips while Missus O gently rubbed the bar of soap over them. Back and forth she rubbed my upper lip then the lower one before pushing the horrid tasting bar between them. Back and forth she continued relentlessly forcing my mouth to open further with the bar as my spittle caused it to soften and foam. Back and forth Missus O pressed on as the bar foamed more, filling my mouth with the vile taste. Shuddering with humiliation the horrid taste of the foaming soap made me gag. Missus O ignored my plight forcing the bar deeper into my mouth over my tongue.

With my mouth filling with foaming soap I frantically tried to push back with my tongue while pulling my head away. When Missus O’s snarled, “Stop!” I froze. Forlornly I allowed Missus O to pump her bar of soap in and out of my mouth until she was satisfied that I was sufficiently cowed. Holding the foaming bar embedded between my lips Missus O turned to the custodian Mr Jones smirking, “Amazing how easily the youth of today are pacified isn’t it Freddie.”

Freddie, Mr Jones, had been standing by casually witnessing my humiliating submission to Missus O. With cold indifference he shrugged drawling, “Not much hope for the future are they Annie.”

Snorting with derision in agreement Missus O turned back to slap me open handed across the cheek. Not hard but the shock of the unexpected slap forced me to clench my teeth over the bar of soap while sucking in a sharp foam filled breath. Stunned, I knelt there on the chair with my mouth frothing soap foam, my cheeks flushed red with humiliation and from the stinging slap. While I fought to maintain my position on the chair and not gag further on the soap foam Missus O moved to open my pants hauling them down to expose my buttocks like before.