Boarding School Punishment, Scene One free porn video

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Location: An all-boys Military Prep School for young men ages 18 to 22.

Cast:

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!

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WARNING! All of my writing is intended for adults over the age of 18 ONLY. Stories may contain strong or even extreme sexual content. All people and events depicted are fictional and any resemblance to persons living or dead is purely coincidental. Actions, situations, and responses are fictional ONLY and should not be attempted in real life. If you are under the age or 18 or do not understand the difference between fantasy and reality or if you reside in any state, province, nation, or...

2 years ago
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PE Department Punishment Miss Downeys Story Chapter Five

Neither Lindsay Pinkham nor Laura Galley were shocked when their Form Mistress, Helen Downey had read out their names from the list that morning. Both eighteen-year-old sixth formers knew that they were due a punishment for not having their PE kit the previous day.Both girls had deliberately “forgotten” their kit as they hated what they were doing in PE. Gymnastics just wasn’t their thing. Laura Galley, the short, quiet girl who had missed out on being Head Girl to Kim Campbell wanted to be a...

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1 year ago
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The FreshmanChapter 35 Tiffanys Third Punishment

As the summer progressed, Cecilia realized that she was destined to become much closer to Tiffany Walker and Cynthia Lee than to Kimberly. The reason was the lives of Tiffany and Cynthia were similar to Cecilia's life, while Kim's life was very different. Tiffany and Cynthia were single and continued to be very American in their outlooks, while Kim was much more Danubian in her thinking, only a year away from becoming sworn in as a public official, and nearly two years into her marriage...

4 years ago
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A Typical Punishment at the FCI

Correction Officer Joanne Wilson had enjoyed her summer job so far. She had been working at the Female Correction Institute for two months and had succeeded in keeping the true nature of her full-time job a secret from her boyfriend Peter. Just as her boss, Karen Savage, had been advised, Joanne was a natural when it came to administering judicial-level punishments and had picked up the various aspects of the job quicker than most people.Despite her initial doubts, the twenty-year-old ex-Head...

Spanking
2 years ago
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Moms Unique Punishment Reimagined

Mom's Unique Punishment, Re-imagined Original story and concept by Suejrz, 2005 Fan "remix" by tealights, 2020 Synopsis: When Danny Exner gets caught shoplifting, it's the last straw for his mom, who resorts to a unique punishment to curb his bad behavior. If Danny can't learn to behave, maybe Danielle can... either way, it's going to be a long summer. Author's Note: Suejrz's original MUP series was one of my favorite stories on Fictionmania back when I was in college and I...

1 year ago
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Charlottes Punishment Letter

This is the third story in the current series about Mrs Denver. She has disciplined three adults, as well as giving 42-year-old Jenny Howe her second punishment. Charlotte goes home so her Mum can discipline her again and sign her Punishment Letter. It doesn’t go as smoothly as Charlotte had hoped. 25 year old Charlotte Thomson and 39 year old Kelly Hall were both rubbing their bottoms as they walked away from the Academy, each with their Punishment Letter in their hand. Jenny stayed at the...

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1 year ago
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The Dress Punishment

The Dress Punishment Katie Leone Being in the principal's office is never a good place to be, especially after you get caught doing something wrong. It makes you feel kind of nervous when you're sitting there waiting for the man in charge to come back in when you know he's getting all the dirt on you that he could. All I can do is sit here and look at the wood panel walls and watch the second hand of the clock move slowly. "Tick, tick, tick," the...

3 years ago
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Double Punishment DP

She watched as her daughter slowly undressed   Double Punishment January, Regina, Saskatchewan, Canada If you have ever lived in a country where winter lasts six months every year you will understands that from October to March or April you can?t go out without freezing your ass off. One of the worst things to be in these parts of the world is a teenager who has to spend her vacation indoors because she doesn?t have a car. Eighteen year old Brandy Simpson stood in her room next to...

1 year ago
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Silks Final Punishment

Introduction: This is the last part of Silks punishment. There is more to come of what happens before this but here is the last Part for now. Enjoy, comment and rate As I said, there is more to come on this. This is the last part that begins with Anger. I will be adding all this in as the weeks go by so read, comment and rate. And about all enjoy. Please inform me of mistakes too… Faith Michaels… ******************** Since Silk went out with Becker of her own free will, slept with Jason and...

3 years ago
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The Punishment Game

THE PUNISHMENT GAME by Cuirnoir The train would enter Paddington Station about ninety minutes late. An inauspicious start to my return home after my first term at University. I had timed my arrival so that my mother, who had offered to pick me up, did not have to hang around for too long in central London after work. Since we had quarrelled before my departure in October, I was anxious to avoid irritating her at the very beginning of the vacation. I had texted her, and she took the...

3 years ago
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Ninas Punishment Letter Spanking

Nina was at least glad that the time to go home had come but knew she had one last difficult task to do. Having tidied up her desk, she stood up, making sure as she had always done since being spanked earlier that her dress did not ride up so far that her red legs would be easily seen by those behind her. She managed it, and then looked across at Miss Millie, took a deep breath, and, as her bottom was still stinging from the spanking, she walked over to her boss. Millie looked up as Nina stood...

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4 years ago
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Judiths Punishment

Chapter 1 Judith ConcedesSir Jolyon Lattimore reached into the inside pocket of his pinstriped Savile Row suit and took out a gold ballpoint pen which he handed to Judith. “What if I choose not to sign?” asked the young woman as she took the pen from him, a note of defiance in her voice. Sir Jolyon paused for a moment before answering. “Well, whether or not you sign is entirely your decision but should you choose not to sign you will leave me with no alternative other than to fire you on the...

2 years ago
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My Punishment Essay

My Punishment By Satinmaid ([email protected]) Mistress Lisa had cause to punish me recently. I have been living as her woman for the past six years and since that day six years ago when she sprung this on me, I have been utterly forbidden from wearing any form of trousers whatsoever. I am not allowed to wear women's slacks, hotpants, girl's shorts, clam diggers, leggings, skorts or even women's pyjamas. Obviously I am also not allowed boxer shorts, as I am forbidden from ANY...

1 year ago
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Silks Final Punishment

Faith Michaels... ******************** Since Silk went out with Becker of her own free will, slept with Jason and gave Donny a blowjob, which she purposely allowed Michael to catch her doing it just to prove she could have other men if she so choose, Michael felt that a punishment to strictly address this attitude was in order. Sending the other three away for the night Michael lined up something that he was sure would get Silk’s attention and make her never want another man again. He...

2 years ago
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Michelle Part 6 Punishment

My only wonder was whether Michelle had similarly set a trap for me, since she knew that the house was monitored by my computer system. Regardless, I told her I had a two-day conference and that I would fly out early the next morning. I allowed her to sleep in, for her sake, I said, and drove myself to the airport. I did take a flight, but only a lesson with a friend of mine who was still trying to help me get enough hours to complete my license requirements. When we landed we went to...

3 years ago
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Sexual Punishment

(Authors: If you would like to write for this story feel free to message me. The introduction should be ambiguous enough to allow for other genders, settings, fandoms, etc. All characters are 18 years of age or older.) It starts with a particularly mischievous and powerful spirit overlooking Earth. A virgin dies in an unlucky accident; their only sexual experience was an awkward, clumsy fondling session with a now-distant friend. The omniscient, reality-bending entity tuts at this revelation...

Mind Control
3 years ago
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Ninas Tennis Weekend Punishment Part 2

The following morning things returned to normal, as they always seemed to after Nina had to be disciplined. Forgotten was Mrs K’s decision to let Lexie cane Nina, as was Mrs K’s spanking and six more strokes of the cane she had to give Nina last night as the usual and so rightly given repeat punishment the naughty teenage acting forty-one-year-old always got if disciplined by anyone during the day. Of course, as with any punishment, whilst they both returned to the loving and respectful...

Spanking
3 years ago
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Jennys Punishment Letter

Jenny sat on a seat in the hallway clutching her Punishment Letter. She was still stinging from the punishment already given to her by the dominant Headmistress. Now, as her Mum was away, Mrs Denver was going to deal with her, just one hour after punishing her. She was exhilarated and pensive at the same time, still tensing her thighs and giving herself a series of mini orgasms. She still managed a wicked smile as she watched Charlotte and Kelly Hall leave the Academy, both rubbing their...

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1 year ago
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An Even Worse Punishment

Maya loves being spanked, but that means it takes cruelty to punish her. Being a child celebrity isn't easy, most of the time. Thankfully, Aaron made enough money to retire at 17 and decided to call it quits on the whole “working” part of being famous, however, he still indulged himself on the carefree part of it. Living in an apartment in his adult brother's name away from his parents, Aaron enjoyed a lavish lifestyle amidst still going to school. On top of being rich, Aaron was...

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3 years ago
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Punishment 6

Punishment 6 - by Debbie Johnson Chapter 1 - Expectation of a gentleman caller After Maria had taken Jim into her bedroom and repaired his tear-ravaged make-up, she had taken him in a gentle but tight embrace for a few minutes, all the while cooing softly in his ear that he had nothing to worry about and that she and Karen would take care of everything. Despite the punishment that the two girls were putting him through, a punishment that seemed to be continually shredding not only...

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