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Boarding School Punishment, Scene One

Timmy get his punishment and reward.
Location: An all-boys Military Prep School for young men ages 18 to 22.


The Head-Master, Mr. L., is fifty five years old. He is a masculine, six foot, two hundred pound, short haired bisexual who rules the school with an iron hand.

Timmy is a slightly built, eighteen year old, 5’8” tall, 145 pound virgin male, who wishes he was really a girl. Timmy hides the fact that he wears panties and sometime crotch less pantyhose. Timmy masturbates four or five times daily thinking about being force to have sex.

Scene one:

Timmy is in the Head-Masters private office. He is there to receive punishment for not paying attention in class and also missing a marching drill.

“Timmy because you have broken our school’s rules and have been caught day-dreaming in class, you have been sent to me for punishment,” said Mr. L. “I want you to lower your pants to receive a paddling.”

Timmy just stood there in shock. He was thinking about the red silk panties with the white lace fringe he was wearing under his uniform.

“Mr. L. may I please have my spanking with my uniform on? You can even paddle me more than the standard twenty five spanks,” pleaded Timmy.

Mr. L. looked down at Timmy’s crotch and saw a slight bulge. He thought, 'Wow, the little fellow is getting a boner. This is really going to be fun.'

“No Timmy the rules state you must submit to a paddling with your pants around your ankles. Now remove those pants and submit to the humiliation of a spanking.”

Timmy held his breath and lowered his pants to revel his red panties. His skinny, very hard, four inch cock was pushing against the silky fabric.

“Well look what we have here, a sweet young man who is sporting a hard on and wearing my favorite color of panties. This is going to be fun,” said Mr. L. as he rose from his desk and came around and stood in front of Timmy. He looked at the trembling young man as he began to slowly remove his own clothing.

Timmy’s eyes widened as he saw Mr. L. remove his clothes. When Mr. L. removed his under shorts Tim saw his shaved massive cock and balls. His cock, at a soft seven inches, was perfectly shaped, smooth and thick. His balls were heavy and hanging down. Timmy couldn’t believe what was happening.

“Now, Timmy I want you to remove the rest of your uniform, but leave your panties on.”

Timmy did as he was told. Now standing in front of his Head-Master, Timmy was shaking with excitement. Mr. L. sat on the couch and instructed Timmy to bend over his lap for his paddling. Timmy bent over his lap with his ass high in the air. He could feel Mr. L’s big cock rubbing his stomach. Mr. L. put a hand on his back and rubbed Timmy from his shoulders to his calves. Then with the other, he pulled Timmy’s red panties down over his ass cheeks. Timmy could feel his small cock rubbing on Mr. L’s thighs. It was a dream comes true.

Mr. L. took his paddle and spanked Timmy’s bare ass twenty five times, causing it to turn bright red. He then rubbed Timmy’s ass to cool the fire. Then he spread Timmy’s ass cheeks first rubbing then inserting a wet middle finger into Timmy’s virgin asshole.

Timmy was crying as he received his punishment. It was a combination of pain, humiliation and sexual electricity. Bolts of lightning had surged to the tip of his very hard penis with each smack to his bare ass. Timmy felt Mr. L’s finger touch, then be inserted into his boy pussy. This sensation drove him to the very edge of coming. He also felt Mr. L’s cock grow to full hardness.

“Now stand up and remove those panties,” instructed Mr. L.

Timmy slowly pulled down his panties and kicked them off his feet. He stood in front of Mr. L. with his thin four inch hard on sticking up at a forty five degree angle and his tiny balls pulled up tight. Timmy looked down to see a large drop of pre-cum at the tip of his penis. His face was as red as his panties and ass.

“Now kneel in front of me,” whispered Mr. L.

Again Timmy obeyed. He assumed his position of shame, on his knees between his Head-Master’s legs. He was looking at Mr. L’s now fully erect nine inch cock with fear and great desire.

“Timmy I want you to kiss, lick and then suck my cock,” demanded Mr. L.

“I have never done that before, I don’t know how,” Timmy pleaded.

“Just kiss the tip, then the shaft, then my balls, then lick all around everything, then put it in your mouth,” said Mr. L.

Timmy was glad and egger as ever to comply and to please his Head-Master. He first examined his shaft, then the mushroom head and his huge balls. He noticed Mr. L. was completely hairless. Timmy loved everything he saw. He then did as he was told to do.

The first kiss was heavenly as he tasted Mr. L’s pre-cum, as was the kissing and licking, but nothing could compare to having Mr. L’s massive cock in his young mouth.

Timmy continued to do as he was told. Mr. L’s cock was so hard but also velvety soft. The head was warm in his mouth as he flicked his tongue back and forth on the underside of his master’s cock. He sucked the mushroom head and also rubbed his hand up and down on Mr. L’s shaft all the while playing with his balls. Mr. L’s balls were large, smooth and felt so divine in Timmy’s hand. Soon Mr. L’s cock swelled up. Timmy heard Mr. L. moaning with pleasure, then felt the first blast of hot sweet come shoot into his waiting mouth. Timmy swallowed over and over, not wanting to miss a drop and also wanting to please his master.

Mr. L. was moaning and his whole body was jerking as he continued to come in his student’s hot young mouth. It was the best orgasm he had in months.

Timmy continued to milk Mr. L’s cock of every last drop of his salty, sweet nectar. It was if Timmy had been sucking his cock his whole life.

Mr. L. pulled back his now limp spent cock from Timmy’s talented mouth. “Timmy, you have pleased me greatly but you punishment has just begun. I want you to sit on the edge of the couch”.

Timmy again obeyed his Head-Master. Once seated on the edge, he saw Mr. L. kneel between his legs, just as he had done did a few minutes ago.

Mr. L. reached out his left hand and encased Timmy’s balls. He squeezed. He then grabbed Timmy’s four inch very erect cock in his right and pulled. Timmy let out a squeal. It was part pain and part pleasure. Mr. L. continued to jerk Timmy’s cock by pulling it very hard. He was stretching his cock and pulling and squeezing his balls at the same time.

Timmy knew he was going to come any second and he shouted, “Mr. L. I am going to climax.”

Mr. L. quickly bowed his head to Timmy’s cock and took his entire cock into his mouth.

Timmy couldn’t hold back and sprayed his young hot seed into Mr. L’s mouth. Mr. L. swallowed it all.

When they both recovered Timmy stood and went to reach for his clothes.

Mr. L. said, “What the hell do you think you are doing?”

Timmy turned and saw Mr. L’s cock had sprung back to its full hardness. It really looked quite beautiful to Timmy. His cock was long, hairless and smooth with a large tube on the underside. The slit was also much bigger than Timmy’s pee hole. His balls were also hairless, smooth and very large. They hung down in their sack just waiting to be called upon to deliver another load of swimmers to join the fluid from the prostate to Timmy’s mouth.

However, Mr. L. had another place to fill on his mind.

“Timmy I want you to lean over my desk, on your stomach, spread your legs and pull your ass cheeks apart,” demanded Mr. L.

“Please,” pleaded Timmy, “I have never done that either. My ass is too small for your big cock. Let me suck you again. I will give you even a better blow job this time.”

Mr. L. would have now of that. He wanted Timmy’s virgin ass.

“Timmy because you refuse me, I will give you another twenty five spanks, then I will still have my way with you pretty little ass.”

Mr. L. took the paddle and spanked Timmy’s ass again until it was crimson and Timmy was crying with pain. He then took some gel and spread it on Timmy’s puckered bun. He pushed his middle finger into his asshole to be sure it was well lubed.

When Timmy felt Mr. L’s finger push deep in his ass he let out a squeal of pleasure. Maybe, he thought, this won’t be so bad after all. Timmy tried to relax for what he knew was about to come.

Mr. L. also lubed up his member, and then lined it up to Timmy’s waiting pussy. He put the head to Timmy’s small puckered hole and pushed. His large mushroom head popped right in.

Timmy yelled out from the blinding pain. He then felt Mr. L. stop and a few minutes later the pain was almost gone. Then Mr. L. pushed in again and Timmy felt his cock go deep into his bowels.

Mr. L. then started with slow short steady strokes as Timmy’s ass got used to the invasion.

Soon Timmy was actually enjoying the feeling of Mr. L’s huge cock as it pushed deeper and stroked faster into his then no longer virgin asshole.

Mr. L. shouted, “Oh fuck yes, oh fuck, oh fuck, oh fuck, I’m coming, oh fuck here it comes.” He then unloaded a torrent of hot cum deep inside Timmy.

Timmy’s, as he was being pounded, cock was rubbing on Mr. L’s desk with each stroke. When Mr. L. grunted and shot his come Timmy shot also all over Mr. L’s desk.

When Mr. L. removed his spent cock from Timmy’s dilated hole he stood up. That is when he saw the mess Timmy made.

“Timmy, lick up every drop of you cum from my desk,” screamed Mr. L.

When Timmy was finished licking up his own come Mr. L. had him clean off his cock with his mouth. Timmy was very happy to oblige his new master’s request.

“Now get dressed and say not a word to anyone. This is our little secret. Report back here tomorrow at the same time. I am not finished with you yet.”

Timmy was happy to hear Mr. L’s words.

Yes, Timmy thought, my ass is sore, my ass and belly is full of come, I had great sex and I shot my load in his mouth…I am a happy girl!

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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