A Trip to the Head

Rate This Story:

Another erotic story from the FLOGMASTER!

Copyright 1995-2009 by the Flogmaster. All Rights Reserved. Free distribution via electronic medium (i.e. the internet or electronic BBS) is permitted as long as the text is _not_ modified and this copyright is included, but _no_ other form of publication is allowed without written permission. This document _may_ contain explicit material of an ADULT nature. ***READ AT YOUR OWN RISK!*** Anything offensive is your own problem. This story is for **entertainment** purposes only, and it does _not_ necessarily represent the viewpoint of the author or the electronic source where this was obtained. All characters are *fictional* -- any resemblance to real people is purely coincidental.

Purchase this story in print form!


Don't like reading on screen? This story is available in print form in Ultimate Archive: Volume 2 at the Flogmaster's Bookstore. Purchase your copy today to encourage the Flogmaster to write more cool stories.

A Trip to the Head

(****, F/m, Severe, schoolboy caning)

A horrified lad discovers his first caning will come not from Headmaster, but the Assistant Headmistress. (Approximately 5,207 words. Originally published 1997-12.)

"Hey, Bark -- you gonna get the stick?"

I glared resentfully at fair-haired older boy approaching to torment me. "What makes you ask that?" I whispered, glancing around to make sure others wouldn't overhear.

James grinned saucily and spoke loudly. "Heard you got your third demerit in a week -- third one's the charm, boy. Always an automatic trip to the HM, bent across his desk, six-of-the-best."

I struggled vainly for dignity but I could feel my cheeks steaming. My prepared defensive response vanished from my mind at the terrifying image James painted. "S-s-six?" I mumbled, trembling despite my resolve to act brave before my mates. "He wouldn't do six, would he? It's my first time!"

By this time Andrew and Tom were approaching, wonder and amusement on their faces. "You got a third?" asked Andrew, a touch of respect in his voice. "Ouch!"

"Buck up, Barkley," grinned Tom, punching me on the shoulder. "It goes quick. Bam! Bam! Bam! and it's over."

I nodded glumly, staring at the floor. My stomach twirled with sick fear. How could this be happening? How could I have been so stupid? It was all that girl's fault -- a blonde named Gretchen. When she smiled prettily at me and slipped me a note to pass to her friend Rene, I couldn't refuse. Of course I was the one caught. I didn't dare tell Mrs. Davenport the truth -- I simply nodded when she wrote me down for a demerit. Fortunately the teacher didn't recognize the handwriting.

So now I was in the lockers, changing into the required gym kit, readying for my trip to the head. My gray shorts were thin and very tight -- the thought of a long cane smashing across them was dreadful.

"Better get going," said James, laughing as he pointed to the clock. "It's nearly four o'clock. If you're late the Head gives 'em pants and knickers down."

Icy terror lanced through my body as I stared at the older boy in disbelief. He couldn't be serious, could he? The head would cane me bare bummed? But Tom and Andrew weren't denying his assertion, which meant either they were party to his joke or he was telling the truth. Slipping on my white gym shirt I hurried from the lockers, the laughter of the boys echoing after me. My dawdling had cost me -- I had exactly three minutes to reach the head's office.

I made it, though I was panting and flushed when I got there. The pretty secretary, Melinda, took the note I offered her. "I-I -- gasp -- am here to-to... to see the Head." I hung my head low, embarrassed.

Melinda licked her ruby lips as she studied the note from Mrs. Davenport. It showed that she'd given me my third demerit in a week, which was an automatic trip to the Headmaster's office. Her brown eyes went large. "Oh!" she said. "I see you've been a naughty boy, Barkley. Better go right in. The Head's not here but you can wait in his office."

She gave the note back to me with a sympathetic smile. I gulped and nodded, my hand trembling shamefully as I grabbed the piece of paper. My face burning, I turned away quickly and started down the long corridor to the Head's office. His door was at the far end, nearly twenty feet away. "Headmaster Grimm" the sign on the door read. I'd only been inside once before, not long after arriving at school, and that time I'd gotten a stern lecture and six strokes with the slipper across the seat of my shorts. Even now my bum tingled at the memory. Suddenly I felt woefully underdressed.

The door creaked open slowly, revealing a dark room filled with Dreadful Things. I could feel the invisible presence of generations of naughty schoolboys and schoolgirls crying, and I could hear the appalling "swish-crack!" of a slender cane whacking a tender arse. I flicked on the light, fully expecting to see dozens of teary-eyed children staring at me woefully and rubbing their sore bums, but the room was deserted.

The room was exactly as I remembered it. A large bookcase stretched across the wall in front of me. To my left was a small couch where guests or waiting students would sit, large stuffed chairs on either side. To my right was the Head's huge mahogany desk, clean and tidy, and gleaming with shine. Next to the desk were wooden filing cabinets and storage systems.

But the Featured Item was on prominent display behind the desk. Attached to the wall was a large wooden gun case with a glass door. Through the glass I could see three crock-handled canes. They were light brown, slender, and slightly warped from years of use. My mouth went dry as I stared at them. Though I didn't want to see them, I couldn't have looked away for a million dollars.

The shortest one was at the bottom. It was perhaps two-and-a-half feet long and very thin. That, I knew, was the junior cane. It was most often used on first offenders, and usually on the hands. The other two were the same length -- over a yard -- but the top one was much thicker and knobbed in places. It was frightful, and I prayed that I'd never taste the senior cane. Surely for me it would just be the junior one, hopefully no more than two or three strokes.

Time passed with agonizing slowness. The room was as still as a tomb. I was nearly afraid to breathe because any sound unnerved me. After an hour of twiddling and fiddling and impatient wiggling on the sofa, staring at those horrible canes, I glanced at the clock above the door. It was four-ten. I nearly began to weep. It was bad enough to be caned -- worse was the interminable waiting!

Finally I heard a slight creak from the corridor. Every muscle in my body tensed in horror as footsteps approached. The door slowly creaked open. But instead of the ponderous bulk of Mr. Grimm, the Headmaster, a tall, elegant woman entered. My gasp was distinctly audible in the quiet.

She turned and looked toward me, her angelic face pale with rosy cheeks and bright blue-green eyes.

"M-Miss Craven!" I nearly shouted, leaping to my feet.

The Assistant Head was every schoolboy's dream. Her neat, curly blonde hair was trimmed short around her oval-shaped face. Her lips were pink and moist and her even white teeth gleamed magnificently when she smiled. Her eyes were mysteriously deep and friendly -- one just melted into them. I'd seen more than one fifth-former begin to cry simply because she glared at him with disapproval.

I was horribly embarrassed at her finding me here. This was the last place on earth I'd want to meet Miss Craven. Her opinion of me, if she even had one prior to this moment, must be extremely low. I flushed and bowed my head.

"I-I'm waiting for the Head, Miss," I whispered, to ashamed to look at her.

The woman shut the door firmly behind her. Even from several feet away I could smell her delicious perfume, a soft, feminine scent, rich with meaning. It had me shivering. I opened my eyes a bit and glanced up, afraid those beautiful azure eyes would be glaring at me with disapproval. My knees felt weak.

Instead she was smiling slightly, her lips pursed together in a thin line that turned up at the corners. "Yes, I know, Barkley," she said primly, removing her dark blue blazer and hanging it on a tall wooden post by the door.

She stood and faced me, hands on her hips. She was a large woman, tall and imposing, athletic and strong. She wore a tight white blouse and a long navy skirt that swished when she moved. I had absolutely no idea how old she was, but she seemed far too youthful to be an Assistant Headmistress.

"Mr. Grimm was called away on a family matter this morning. I have taken over his duties for the day."

Her words slowly drifted into my thick skull and penetrated my brain. I tore my attention away from her soft bosom and focused on what she had said. The Head was to cane me. The Head was gone. She was taking over for the Head. Therefore, _she_ was to cane me!

I staggered back and nearly fell I was so surprised. "But ma'am--"

Again, her gentle smile gave me strength. It was filled with a touch of humor that I found marvelously enchanting. "You don't think a woman has the ability to cane a naughty boy?" she asked, her eyes twinkling with sparks of fire.

"Uh, no ma'am, it's not that--"

"Then you don't think a woman can cane a naughty boy as hard as a man, is that it?"

"Uh, no ma'am, I'm sure you can, it's just that--" I stopped, frozen in terror and bewilderment. How could I explain? The thought of a caning from Mr. Grimm, as severe as that was, now seemed like a mild torture compared to what I was facing. That this delicate, beautiful creature was about to whip my arse sent dozens of contradicting messages to my brain and body. Was I excited? Was I afraid? Was I curious? Was I about to laugh or about to cry? I had absolutely no idea.

The woman eased her backside onto the Head's desk and sat, legs dangling, grinning at me in amusement. "This is your first time, isn't it?" She opened a manilla folder she'd brought with her and studied it intently for a few minutes.

The silence was deafening. I kept hearing echoes of canes swishing and cracking in my head. Every now and then the woman would cluck her tongue, whether in surprise or disapproval, I couldn't know. Finally she put down her folder and shook her head at me.

"I see that you are a consistently naughty lad, Barkley," she said, her lips curling downward in a frown. My knees wobbled in terror. "While you've only been here once before -- that was for cheek, and you got six with the slipper -- you seem to regularly earn demerits, one or two a week it seems. Your behavior isn't bad, just naughty. This time, however, it seems to have caught up with you."

Her beautiful eyes gazed at me sternly. "Make no mistake, young Barkley -- it shall be the cane for you today."

I trembled and shook. "Oh, please, Miss," I murmured, but my voice was so soft I could scarcely hear it myself. Tears had gathered in my eyes and a blinked them back furiously. I couldn't let Miss Craven see me cry. I was twelve years old now. A big boy. "Buck up, Barkley," I said to myself. I stood straighter and nodded solemnly at the woman. She smiled back.

"Please give me your note," she ordered. I did not move. "Hello? Your note, please. Barkley! I am speaking to you!"

It took all my strength to comprehend her instruction and move forward. Her sweet scent was overpowering as I grew near to her. I held out the note, willing myself not to tremble. It was in vain. As she took the piece of paper from me her hand squeezed mine gently but firmly.

"Be brave, lad. It will be over soon," she whispered. I flushed and looked away in shame.

She read the note in silence, then placed it inside the folder and put that on the desk next to her. "Shall we get started?" She hoped off the desk and held out her hand.

Frightened beyond belief, but somehow incapable of running away, I placed my hand in hers. She led me behind the desk. Walking next to her was a dream. I could smell that delicious scent and hear the soft rustle of her clothes as she moved, the hiss as her thighs rubbed together. It was intoxicating.

Letting go of my hand, she smoothed her skirt down behind her, and sat in the Headmaster's large leather chair. "Come across my lap," she said quietly.

I stared at her in terror and confusion. What was she doing? This was no way to administer a caning. I'd expected a lecture, perhaps, but not... this, whatever this was.

"Ma'am?"

"Shhhh," she whispered, placing a slender finger across my lips. "Do not speak. You are frightened and nervous. This is your first time. I understand. Please, let me give you a little spanking. It will relax you and prepare you for the cane."

Horror or horrors! This woman was asking to spank me as though she was doing me a favor! Every instinct in my body and brain told me to flee. I imagined myself turning, rushing to the door and flinging it open, and running down the corridor and pasted Melinda, the beautiful secretary. But I couldn't move. My feet were nailed to the floor. So I stood and stared in dumbfounded apprehension, my hands moving behind me on their own accord, protecting my bottom.

I didn't resisted when Miss Craven's gentle hand took my arm and pulled me forward. If she had been placing my head into a guillotine I wouldn't have struggled any more or less. I was like a rag doll, limp and pliable. I felt myself being drawn forward and down, and as her sweet smell overwhelmed me, I went along helplessly.

My face passed closely over Miss Craven's lap. I could see the slight indentation where her skirt had sunk between her legs, showing me the sleek outline of her thighs and -- for a scant second -- the bulk at her crotch. Then I was staring at the floor on the other side of her, my heart pounding so loudly it hurt. My belly settled across her lap, my legs dangling. I could feel my shorts tight across my bum and my face burned with shame. This was impossibly humiliating. I moaned, wiggling as best I could.

"Be still," came the sweet voice, and I felt a hand gently squeeze my bottom. I'd never felt anyone grab me like that and I froze in fear and wonder. My body quivered with bewilderment. Electricity was shooting through me. I sweated profusely though the room was cool. My mouth was dry and I could not speak. The hand rubbed my bottom gently, caressing me, and I felt like I would explode the tension inside me was so great.

Suddenly the hand was gone and my bottom tingled and felt naked and alone. I heard the dull "whack" long before I felt it. The hand was already high in the air when a dull warmth flooded through me and I realized with astonishment that Miss Craven was indeed spanking me like a little boy!

The hand came down again, the warmth intensifying. I cannot say that it hurt. Over my shorts and knickers I was fairly well protected, and Miss Craven was not spanking me very hard. In my confused state she could have placed a branding iron against my skin and I doubt I would have felt it. But it was horribly humiliating. I whined and moaned, kicking my legs and fidgeting, pleading with her to let me up.

Miss Craven ignored me completely, concentrating on whacking my bum as soundly as she could. She spanked slowly and deliberately, and nothing I did varied her tempo in the least. Soon the dull warmth became a mild burn, and then a sizzle, and I began to writhe and turn my bottom to avoid the blows. It wasn't something I did consciously -- I couldn't help myself. There was no escaping the spanks, but I did manage to rotate my bottom so the spanks never landed in the same spot twice in a row.

"Stop wiggling," scolded Miss Craven, not halting her discipline in the least. "You are a big boy now and should be able to take a little boy's spanking without fidgeting so much!"

I tried to be still but the burning was growing hot and uncomfortable. Breathing was becoming difficult and I gasped for air. My legs kicked and thrashed and Miss Craven intensified her tempo. Now she was spanking me at a blow per second, a rapid bam-bam-bam that threatened to overwhelm me. I moaned loudly, wiggling frantically. "Please, Miss! No more, Miss! It hurts!"

But the hard spanks continued. Tears stung my eyes and I shook my head furiously. It was not fair. How could she do this to me? Dread filled me as I remember the caning was still to come! Surely not. Surely this spanking was my punishment. She couldn't seriously expect to cane me in addition to spanking me!

Suddenly the hand was resting on my bottom again, the strong fingers kneading and squeezing my backside.

"Feels good and warm," she announced to the world. "Have you had enough, young Barkley?"

"God, yes!" I gasped, moaning. "Please, no more. Please let me up!"

"Certainly," she said, giving me a final couple pats on my backside. "Get up now."

She helped me up, sliding me to her right so my feet came in contact with the floor and I could rise. My left hand brushed across her thigh as I stood. I felt a tingling in my hand as I sensed the smooth, warm flesh under her skirt. My face went hot and I couldn't look at her, but she didn't appear to take any notice of my action.

"Ready for your caning, Barkley?" she asked boldly.

"Oh, Miss," I groaned, tears rushing to my eyes. "Please have mercy!"

"I told you, Barkley, you were going to be caned today. I am a woman of my word. Now, which cane shall it be?"

I blinked and stared at the woman through my tears. She had turned away from me and was unlatching the cane case. I couldn't help but notice her slender figure and rounded bum as she leaned forward and stretched upward. She slid the glass panel up and studied the canes. To my horror she took down the senior cane!

She bent it experimentally in her hands. "Ah, a nice stout cane this one. Been here for generations. I tasted it myself when I was a schoolgirl."

My jaw dropped open imaging Miss Craven bending over for a caning. And with the senior cane no less!

The woman winked at me. "But this one's too severe for a first caning, I think. Perhaps in a few years, when you grow into a young man you'll be ready for a man's caning."

I nearly wept with relief as she replaced the senior and took down the tiny junior cane, bending and swishing it through the air.

"Not bad," she murmured thoughtfully. "Stings, I'm sure." She winked at me again, as though her thoughts and my thoughts coincided. "But you're much too big a boy for a whipping with this one. This one's for little girls. No, I think the medium cane will do perfectly."

Dread overcame me as she put the junior back and took down the middle one, fully as long as the senior cane, but much thinner and lighter. It would sting and leave marks, but the marks would fade in a few days. Stripes from the senior cane lasted for weeks.

The tension of this game the woman was playing, winking at me and drawing out my punishment inexorably, got to me suddenly. With resolve that astonished me I boldly stepped forward to the desk and bent over it.

"How m-many, Ma'am," I asked bravely.

The assistant headmistress seemed delighted by my courage, walking quickly around the desk to stare at me from behind. I flushed and bravely held position.

"The standard punishment for a first offense is three strokes," she said mildly, "but you are a very naughty boy, are you not? Don't you think I should whip this bum much longer?" Her hand patted my rear as she spoke and I shuddered.

"Please, Miss!"

"Yes, at least four, I think. Perhaps more, depending on how well you take them. You will be a good boy for me, won't you? Staying in position and not crying out and making a terrible fuss?"

I moaned and shook my head. The desk was hard and my awkward position felt dreadfully exposed. "N-not too hard, Miss, please," I begged. "I've never had the cane before."

"Then we must make your first experience with it memorable," said the woman, and I heard the chilling sound of the cane swishing through the air. My bottom twitched and the heat from my earlier spanking felt quite pronounced.

"I will warn you right now that I take canings very seriously. A caning does no good unless it's a stiff one, and I make mine the stiffest. I was caned as a child and though I can still remember how badly it hurt, it did me a world of good."

"Oh, please, Miss!"

"Now buck up, lad. Be brave. It will be over soon and you'll be the better for it."

Something hard pressed against the seat of my shorts and I tensed my legs in anticipation. My palms were sweaty as I gripped the opposite side of the desk. How much would it hurt? I thought.

There was a long pause, then a swish followed by a loud firecracker explosion. Intense, blinding pain overwhelmed for a few seconds, and then I became aware of a deep and biting ache across my bottom. The stroke had landed full across both cheeks, high across the top of my bum. The stinging was amazing, but it faded quickly. I blinked back tears and realized with surprise that I hadn't cried out.

"There's a good lad. Well taken. Stay down, now. That's one," came the sweet Siren voice of my tormentor.

I was more conscious for the second stroke, and gasped loudly. The pain was worse -- much, much worse. My fingers went white as I gripped the desk with all my strength so I wouldn't rise up. I couldn't let Miss Craven see how much she was hurting me. The line of agony across my seat felt like a hot branding iron against my bare skin. Surely she had sliced clean through my shorts. I could scarcely believe I had survived.

"Steady now. That's two."

Swish-CRACK!

"Ahh hhaah ahh!" I yelped, writhing in misery on the desk. Tears spilled unbidden from my eyes and splashed across the polished wood. My fingers hurt from their impossibly tight grip but that was nothing compared to the pain behind me. It rose and flooded through me, searing and burning. That stroke had been low, near my thighs, and I thought I would die the pain was so bad. My entire arse was on fire, all three stripes sending painful messages of alarm to my brain. I choked back sobs and moaned, stamping my right foot in a desperate measure to diminish the pain.

"That's very good, Barkley. Well-taken. I told you it wasn't so bad. Just one more, then we'll rest and take a look at those stripes."

The teacher's words flowed over me like water. I couldn't understand a word she said, but only sensed her tone. She found this an amusement. It was a hard thing perhaps, but nothing more than that. "It will be over soon" she kept saying, as though that made everything alright. Well it had taken an eternity to get this far. Soon wasn't soon enough for me.

I knew without any experience that the last stroke would be the hardest. I didn't see how I could endure it. I knew it would have me screaming around the room, dancing and holding on to my arse with all my strength. Miss Craven would see what a baby I was, and she would be disappointed that I couldn't take my caning like a big boy. It hurt me to realize this, but there was nothing I could do about it. She was about to whip my arse a fourth time and it was going to be the worst pain of my life. I would just have to fight it the best I could.

There was the soft swish and the cane struck me hard across my lower bottom, slightly below the previous stroke. Sharp, indescribable agony flooded over me, and for a few seconds I thought I was dead. Then the pain eased, slightly, and I could breath again. To my amazement the pain wasn't nearly as bad as before. Until then each stroke had built upon the previous, becoming more and more unendurable, but the third stroke had seemed to be the peak. The fourth stroke only extended the pain. It _was_ agonizing -- I could not stop weeping -- but it was endurable. I had not screamed and jumped about the room uncontrollably. I had taken my caning like a man!

"Very well done," said the soothing voice of the woman, and I felt her kneel next to me. "I know how hard that was for you. The first caning is always the worst."

Her hand rested on my back as I shuddered and quivered, huge sobs bursting from me uncontrollably. I wept more from relief than from pain, for the pain was already fading. The caning was over and I had survived!

Suddenly I tensed as the woman's hand palmed my bottom. She touched me gently, I knew that, but still her hand hurt and brought forth a huge, choking sob from deep within me. "Oh, please, Miss," I groaned, wondering what other possible torture she could have in mind.

"Stay in position, lad," she scolded gently. "Let's just have a look at those stripes, shall we?"

I couldn't protest though every nerve in my body screamed in disagreement with her plan. Her fingers grasped the elastic of my gym shorts and slowly drew them down. I could not breath in my terror. Surely she did not intend --

Of course she did. My white cotton knickers quickly followed my gray shorts to my knees and I lay there and wept in the purest misery, too utterly exhausted to argue with the teacher.

"Oh, very nice," she murmured softly. "I can see four distinct stripes here. This first one is a bit weak, but the other three are indeed crackers."

Her finger went out and carefully traced each stripe for me, as if I couldn't tell where they were from the feeling. My arms and hands ached from my awkward position, but I couldn't have moved to save my life. I lay there and let the woman play with my bare bottom for God only knows how long. She poked and squeezed and patted and pinched, and I just moaned and wept and prayed for an end.

"There's quite an opening here, lad," the woman said, her hand carefully caressing the empty space between the first and second stripes. The three final ones were grouped together at the base of my bottom, leaving the middle area clear. "That's the trouble with caning over shorts: you can't see where the strokes land. Back in my day, every caning was given on the bare bottom."

I shuddered, my mind filled with the image of a stern headmaster holding a long cane in his hand, a naked Miss Craven bent across his desk waiting for her punishment.

"Your mates are going to tease you about this white area," mused Miss Craven, still caressing me. "I think we should fix that. What do you say to two more, with feeling?"

I didn't answer, too weak from shock to move my mouth.

"Come on, lad. It will be an even six. Your mates will be impressed. I'll put them right here so your bum will be well-striped."

I didn't have to ask if she meant to cane me bare bottomed. She was already lifting the cane and stepping back. I was too terrified to move. A distant impulse pricked at me to run for the door, but something held me in position.

There was a sharp swish and followed by a louder, more intense pop. The pain was startling. It came at me faster, a rush of stinging that took my breath away. Miss Craven mercifully didn't give me a moment to think about it but promptly whipped the cane down again, this time a bit lower, and I had no doubt that my bottom held six parallel strokes.

I rose up, howling in and grabbing my rear in distress. My face was streaked with tears as I danced and sobbed. "Oh, please, Miss Craven!" I moaned. "No more, no more!"

She smiled and approached me, kissing my cheek lovingly. "I think you've had enough, dear," she whispered. "You learned your lesson, didn't you?"

"Oh yes, Miss, yes!"

"Good." She hugged me, my face deep with her soft bosom, the smell of rose petals and cleanliness overwhelming everything. I forgot about my nakedness. I forgot about the pain in my behind. I forgot where I was and who she was. I clung to her, weeping without restraint. She hugged me for a second longer, then pulled away.

I thought I would die with shame as she knelt in front of me, slowly drawing my knickers up. The cloth against my bottom was a painful irritation, but I scarcely noticed it, too stunned at the woman seeing me so exposed. She didn't seem the least bit bothered, however, carefully rearranging my underwear to adjust for the sudden increased size of my penis. She patted it gently, through the cloth, and with a friendly smile, drew up my shorts. They seemed impossibly tight and she had to struggle extensively to get them to fit. It hurt unbearably, but I didn't move to help her, simply standing and wincing as she fiddled.

When I was dressed she stepped away from me, took up the cane, and returned it to the case. She closed the glass door and sat in the chair. She opened a drawer and took out a black book I recognized as the punishment log. She carefully wrote for several minutes, then turned and offered the book to me to sign.

Her inaccurate entry read: "Barkley Simpkins, 12, received six strokes of the cane across his gym shorts as punishment for mild but continual misbehavior culminating in three demerits in this week. Punishment administered by Angela Craven, Assistant to the Headmaster."

As she looked at me, eyes sparkling with that devilish amusement I found so enchanting, I realized with sudden rather adult perception, that it most likely was against school policy for a female administrator to punish a boy on the bare bottom. If I squealed she could be in serious trouble.

I let her worry for a moment, seeming to hesitate, and then signed. She smiled broadly at me. "Very good, Barkley. You're a good lad. I hope I shan't have to cane you again soon."

"Me too," I breathed. But as I shut the door softly behind me, the weals on my bottom aching as I walked, I wondered: had I told the truth?

The End

Rate This Story: