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The headmaster and the boy

by Icey

Copyright on this story text belongs at all times to the original author only, whether stated explicitly in the text or not. The original date of posting to the MMSA was: 05 Jul 2011


My first fantasy fiction



He knocked and entered. He could see the headmaster sitting at his desk and a chair placed in the middle of the room. He could fell the butterflies in his tummy. He didn't listen to the lecture.

The headmaster liked to punish boys. He liked to break their will and make them “headmasters' house captains'” He was in his sixties, very experienced, grey and balding with a red complexion form the wine and Viagra he had taken earlier.

“Shoes and socks off” he barked and sat on the chair. He beckoned the boy with a plump finger. He was a horny old man and he was going to enjoy this.

The boy stood as told between the heads parted thighs, hands on head. He could smell the alcohol on his breath and noticed a thin line of sweat on his top lip. He felt the fumbling hands undo his shorts and stepped out of them as they reached the floor. He felt warm hands in the waistband of his pants as they were removed. He couldn't help the swelling in his cock as the headmaster looked up to his eyes, cupped his balls in one hand and gently pulled back his foreskin.

He liked the humiliation of his pupil. It was part of the punishment. After all he was checking the boy was “clean”. He playfully slapped the boys cock and smiled as it bounces back up. “Naughty boy” he said, and produced a clean hanky from his pocket and laid it carefully on his left thigh

“Right then, over we go”

He lowered himself over the headmasters lap.

“Hold on tight to the rungs of the chair boy and don't let go until I say”.

He felt hands on this bottom, caressing. He felt the heads arousal pressing into his tummy. He felt a finger trace a line from his lower back between his cheeks to his anus and tensed.

The head felt the clench. “You need to stop that behavior if you want to be a house captain, shall we try that again?” He paused, “legs apart”.

The boy felt the cold lotion as a small amount was worked into his crack and on to his pink anus.

The heads liked smooth bottoms. His thumb traced the crack of his buttocks and slowly rotated around his virgin hole while his fingers lightly squeezed his scotum. “That's better” he encouraged as he sensed the boy relax.

The boy was starting to enjoy the sensation and was confused as the head barked “Five minute spanking boy let us begin”

The first spank shocked the boy. Not because it was particularly hard it was the sudden shift from caress to slap. First the right cheek then the left back and forward at a steady pace working all over his buttocks. The heat began to spread but it was a nice heat and after a minute or so the boy started to writhe in anticipation and grind his hips on the heads lap.

The head read the signs; he had more in store for the boy and didn't want him shooting his load just yet. He paused and repositioned the boy on his left leg and carefully moved him back a little so that the boys penis was pointing straight down to the floor and against his thigh. He wanted to spank him “cock soft” and see it retract. He placed his right thigh over the boys' legs and clamped him into position. The boys bottom was now perfectly presented and already a nice shade of red.

“Enough warm up, let's see what you're made of”

Suddenly 1 2 3 4 5 6 hard smacks rained down on the same place on the right buttock then 6 more on the left then back to the right , 6 more just overlapping the last area and so on, back and forth.

The boy soon noticed the difference. He tried to remain quite but the hurt! He tried to dodge the slaps but he was held firm.

“OHHHH Sir, Ahhhhhh ohhhhhhh no more”.

“Please sir, ohhhhh please stop”

“Ahhhhhhhh it really stings”

His knuckles were white gripping the chair rung, he felt the tears welling up inside. He tried to hold them back but he had lost control and still the smacks came six right, six left. The tears flowed.

The head wanted tears, he wanted to break the boy to his will but he wanted real tears. Some boys would cry easily to try and reduce the punishment so he continued, just to be sure. He noticed unlike himself, the boy had lost his erection as he continued to wriggle cry for mercy.

“No more please sir” he sobbed “I can't take any more”

And let go of the chair with one hand to try to protect his very red bottom.

“Will you be a good boy and do exactly as you're told?” the head said as he slowed a little and smacked either side of the boys desperate defense.

“Ohhh ahhhhh yes sir, I'll do anything you say” he managed to gasp between tears.

The head stopped and admired his handy work. A beautiful red rear glowed up at him. He could feel the heat as he moved the back of his hand over it. The boy lay limp across his knee sobbing quietly, broken to his will. He was breathing hard and eager to relieve his own throbbing member but he knew this boy could be worked a bit harder. He released his right leg that was still pinning the boy and reached over to his desk for the cooling gel.

The boy was still sobbing. The heat in his bottom was unbearable. Then something cold touched him and expert hands which were moments ago raining fire on him were cooling and soothing. Slowly the sensations began to arouse him again, his head felt dizzy and he parted his legs and let the hands explore and gently probe him. “Relax” the heads voice said as he felt the tip of a finger slowly move in and out of his little bum.

The head slowly eased the boy of his knee to the floor between his thighs. He looked at the tear stained face and smiled.

“Come hear dear boy” he said as he guided his face to his obvious erection. “Do you want to be a house captain?”.

The boy gulped as he felt the enormous cock pressing on his cheek through the headmasters trousers. He wanted to thank him for stopping the spanking but what did the headmaster want him to do, undo his trousers and put it in his mouth? He was too scared to move

The heads patience was thinning. He grabbed the boys' hair and forced his face hard against his bulge.

“Remember boy, anything to be a house captain?” The boy remained terrified

“Right young man, let us continue.” He head said impatiently “Go and stand facing the corner, hands on head feet 18 inches apart”

The boy did as told his shirt riding up as he placed his hands on his head to expose his sore bottom and semi erect small penis. The boy felt the heavy breathing of the headmaster behind him. He felt a gelled hand reach round and gently start wanking his cock. He was soon very hard. He wanted to cum desperately. He was rocking with the hand motion, going up on tip toe clenching and thrusting his buttocks forward

“Do you deserve to be milked boy?” Asked the head. He knew he had the boy on the brink. He stopped abruptly and let go. The boy thrust his cock forward and it bounced up and down in anticipation. He liked the boys movements to encourage him. He squeezed his balls and playfully slapped his cock and admired how it stood proudly out. He moved behind the boy and worked his cokc with one hand and his balls with the other.

The boy could feel the headmasters erection against is buttocks. He was being brought expertly back and forth to the brink.


The headmaster turned and walked to a wall cupboard. “I think you need to earn your milking boy” he said as he surveyed the array of spanking implements on display.

The boy glanced nervously over his shoulder, still rocking forward and pressing the wet tip of his hard cock against the wall desperately craving its release. He wanted the headmaster to continue.

The head selected a wooden paddle brush about 4 inches by five hanging by a leather loop on a hook. He returned to the wide eyed boy.

“Right, up on tip toes” and to encourage him he griped his hard cock with his left hand and pulled.

“Stick your bottom out”. With that he brought the paddle down twice on each cheek.


The boy howled with pain, but could hardly move as his penis was being held firm.

“This is my favorite paddle brush” the head said as he put the leather loop over the boys throbbing member.

“Its special to me, if it fails on the floor in the next ten minutes, I will spank you with it very hard”. “Do you understand?”

The boy nodded grimly

“Now face the wall and don't let it fall”.

The headmaster moved back to the chair and sat down. He had a side on view. He watched the boy tensing to keep his cock hard and marveled as his red bottom moved as he clenched and unclenched. He rubbed his swollen member through his trousers. “Not long now” he thought. He undid his fly and pants and pulled his cock out.

“Concentrate boy” he said as he noticed the boy's erection beginning to subside. This only heightened his arousal.

The boy was in turmoil. He wanted to cum and he wanted to please the headmaster. He didn't want to be spanked again but he did. He liked the warm afterglow and he really liked how the head “touched” him. Could he please the headmaster, could he put it in his mouth???

He felt the weight of the paddle brush as it started to slide of his semi erect penis, he tensed his whole body and went up on tip toes.

It clattered on the floor

The head was slowly wanking himself. He saw the paddle brush begin its journey to the floor. He eased his thumb from the base of his helmet to its tip, catching a drop of pre cum. He licked his thumb and the sweet taste heightened his arousal. He covered is cock with his hanky.

“Pick it up and bring it to me boy”

The boy slowly walked to the headmaster head bowed so not to make eye contact. He gave the paddle brush to the headmaster. He noticed the hanky like a small tent, wet at the tip.

“Same as before boy”

He gingerly lowered himself over the lap, careful not to disturb the “tent”

“Please sir, I really tried,” “please don't spank me again my bottoms so sore”

He felt the headmasters right leg clamp into position over his own legs.

“Grip hard boy” and with that unleashed a steady flow of blows on ether cheek in quick succession.





The boy cried out and pleaded for mercy. He let go of the rungs and tried to protect his poor bottom with his hand but the headmaster was ready and pulled it up behind his back which held the boy in a vice like grip.





The boy was crying inconsolably and beating his left hand on the floor.





Breathing heavily the headmaster slowed to a stop and leant over and put the paddle brush on his desk.

“Have you learned a lesson boy” he said as he released the boys arm and the grip he had on his legs.

“Do you want to be a house captain?”

All the boy could do was nod his head and sob as he lay across the lap, hands gripping the legs of the chair. He longed for the cool gel.

The headmaster admired the glorious red orbs on his lap. He reached for the gel and squeezed a generous portion on each buttock then spread his cheeks to drizzle some inside his crack. He placed the gel back on his desk and proceeded to massage the boy's burnt rear with both hands.

The boys sobbing soon turned to purring as he wriggled his bum to attract more attention. His legs parted and his knees bent.

The head need no invitation to finger the boy and gently inserted his middle finger of his right to the hilt the slowly withdrew to the tip the entered again.

The boy started to raise and lower his bottom in time with the headmasters' gentle thrusts.

“Good boy” the headmaster encouraged and slipped his left hand underneath the boy and firmly gripped his hard cock.

The boy had never been in such ecstasy, The smarting of his burning buttocks, the gentle probing of his anus and tight grip on this cock. He tensed, let out a groan of pleasure and shot his load in the headmasters hand and over his lap.

He lay there exhausted.

The headmaster looked down at his own cock. The handkerchief had fallen to the floor. He stroked his erection again. He needed to be emptied. He gave the boy a moment to recover then eased him to the floor again between his parted thighs.

The boys' mouth was inches from the headmasters' swollen cock. He stared at it and tried to imagine taken it in his mouth.

“Please sir, I don't think I can”

“Quickly boy I'm ready to cum.” rasped the headmaster “take it now”

The boy took it both hands. It was thick and hot. He had never felt another cock before. He pulled back the foreskin and marveled at the enormous shinny helmet.

“TIGHTER BOY AND FASTER”The headmaster urged “TAKE IT..... NOW” and grabbed the boy behind his head and pulled him closer.

The huge cock exploded inches from the boy's face. As the headmaster jerked and lifted his arse from the chair, he shot his thick creamy cum and with every tug more shot out covering and dripping from the boys startled face and hair.

The head relaxed on the chair. He looked at the cum covered boy and smiled.

“There is a reason why we teach”O“and”A“levels to house captains at this school boy” and reached into his desk for a box of tissue.

“Clean yourself up boy and go back to your dorm.” “We'll keep the special punishment to ourselves shall we?”

The boy nodded.

“Thank you for punishing me sir”

“Let's not give me a reason to give you house captains punishment again eh?”

The boy carefully put his pants and trouser back on, tied his shoes and left the study.

He found is car keys in his coat pocket and walked slowly back to his car. He felt elated. He had finally found what he was looking for on the contact site. He might find it hard to sit still at work this afternoon. He planned to visit again soon!!

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