The Headmaster and Myself

effmyass

Literotica Guru
Joined
Aug 1, 2006
Posts
698
Kelsey Johnson
18
36C, toned arms and legs, stomach is kind of doughy.she's not fat but not skinny either
Wears tight clothes and acts slutty but hasn't gone past making out before.
She's an heir to a multi million dollar fortune
---


Ever since she came to boarding school, Kelsey has been in trouble.She probably done everything wrong in the book.Now that she's done with boarding school, her parents are sending her to a small private school that will prep her for the rest of her life.But Kelsey still hasn't outgrown her troublesomeness.



ooc:I will play Kelsey. I am looking for someone to play the Headmaster of the small private school who will disipline Kelsey and take advantage of her in different ways. The headmaster may be male or female. PM me with your character description and I'll tell you if you may join.There may also be a Sidekick that helps out the Headmaster w/ certain things.Put in your profile who you want to be.
 
Headmaster John Kelso
30 years old exmilitary
Still is in very good shape due to keeping up with his military workout program even after leaving.


John had decided last year that it was time for him to leave the military and try something new. Before joining the military he was going to be a teacher so he thought why not try something in education. His family was a well to do family with many connections so it was easy for him to find a job. A friend of the family suggested a headmaster job at a private school where he was on the board. He thought that John would be great dealing with some of the spoiled brats since he both came from money and was very strict on discipline thanks to the last 10 years in the military. John took the job last year and straightened out a few of the troublemakers right away. He was enjoying his job and was looking forward to the first day of the new semester.
 
Kelsey was caught smoking out the window of the girls bathroom on the third floor by Sister Judy.Kelsey was then taking to Headmaster John Kelso's office where she waited on a bench for him to call her in.When she was called in.She slumped down in the chair across from him.She crossed her legs and the skirt of her uniform rode up to show most of her legs.She twirled her hair and stared him down.Her shirt unbuttoned to show off most of her cleavage and her the shirt moved up and down showing off more and more every time she breathed.
 
effmyass said:
Kelsey was caught smoking out the window of the girls bathroom on the third floor by Sister Judy.Kelsey was then taking to Headmaster John Kelso's office where she waited on a bench for him to call her in.When she was called in.She slumped down in the chair across from him.She crossed her legs and the skirt of her uniform rode up to show most of her legs.She twirled her hair and stared him down.Her shirt unbuttoned to show off most of her cleavage and her the shirt moved up and down showing off more and more every time she breathed.
Kelso was going through some of the begining of semester paperwork when he got a ring on his phone. Already someone sent to him for disciplinary purposes. This is rediculous he thought. "Send her in"
He looked across the desk and recognized her as one of the new students so he pulled out the file on her history to get to know her better. "Sit up straight young lady and button up your shirt. This school is here to teach you to be a successful woman in life not a cheap whore on the streets."
He gazed down at her file and realized she had a record of disciplinary issues. This should be a fun one he thought. "So tell me miss Johnson why were you smoking when you knew it would just land you in here?"
 
Kelsey rolled her eyes.

"Oh, maybe it was the erotic pleasure of getting caught.Or maybe I just like cigarettes."

She sat up in her chair but pulled her shirt down more.

"I bet all these nuns are whores too.I bet you have your way with them all the time, you just don't want your students to know."

She smiled wickedly at him.She was dying to get under his skin.
 
effmyass said:
Kelsey rolled her eyes.

"Oh, maybe it was the erotic pleasure of getting caught.Or maybe I just like cigarettes."

She sat up in her chair but pulled her shirt down more.

"I bet all these nuns are whores too.I bet you have your way with them all the time, you just don't want your students to know."

She smiled wickedly at him.She was dying to get under his skin.
When she sat up it was hard for him not to notice her ample cleavage. He did have to admitt if he would have met her while touring that he probably would have seen just how much she liked men in uniform. He focused again at the job at hand and let her finish talking.

"Ok smartass. First if you want to smoke I do not have a problem with it as long as its not on school grounds. Rules are rules and they are to be followed. I see you have had problems with authority in the past but I am here to help you with that. Now I will ask you one more time to button up that shirt"
 
Kelsey smiles at him and then puts on a fake pout.

"Why would I cover this up? You know you like it, You don't get to see the nuns in anything.Maybe you like this better."

She walked around to his side of the desk and pushed his rolling chair back against the wall.She stood in front of him and leaned over the desk.
 
effmyass said:
Kelsey smiles at him and then puts on a fake pout.

"Why would I cover this up? You know you like it, You don't get to see the nuns in anything.Maybe you like this better."

She walked around to his side of the desk and pushed his rolling chair back against the wall.She stood in front of him and leaned over the desk.
"Ok if you are going to keep acting like a slut you will be treated like one. All sluts like to be spanked afterall"
He quickly pinned her bent over his desk in such a way she could move very much. He was glad that spankings were still allowed at this old fashioned school. He reached up and grabbed the paddle on the wall behind him. The one with the word discipline painted on it and holes carved in the middle. He thought to himself that he is more used to easing into spankings making sure the girl is enjoying herself but this is a different situation all together. He was going to make sure it hurt like hell from the first swat. Then he brings the paddle back and down very hard for the first swat.
 
Kelsey screams and then smiles at him.

"Ooh, that hurt so much. Why don't you go butt fuck one of your nuns?"

She laughs devilishly as she sees him admiring her butt.She watched as he played with the paddle a little before he brought it down again.She smiles at him and licks her lips.

"Ooh, You know you'd rather have your cock in it right now instead of using a paddle on it."
 
effmyass said:
Kelsey screams and then smiles at him.

"Ooh, that hurt so much. Why don't you go butt fuck one of your nuns?"

She laughs devilishly as she sees him admiring her butt.She watched as he played with the paddle a little before he brought it down again.She smiles at him and licks her lips.

"Ooh, You know you'd rather have your cock in it right now instead of using a paddle on it."
"Still wantning to act like a slut are you?"
He decided to make sure it was going to hurt like hell and leave a mark so he flipped up her skirt to remove that layer of padding. After seeing she was wearing a thong and just how round her ass was he did have to admitt he was enjoying the view even though he wouldnt let it show. He brought the paddle down hard repeatedly on her bare ass. It was pretty firm but still had a bit of ripples when the paddle hit her. He was now hitting her hard enough to leave visible marks for the rest of the day.
 
Kelsey screams out in pain.Her ass soon turns crimson and she starts to cry.

"Oh please stop.Please just stop.

She slumps over the desk.And when he finishes, she continues to lay there.She was unable to move.She raised her head slightly and looked at him.

"Go fuck a nun."
 
effmyass said:
Kelsey screams out in pain.Her ass soon turns crimson and she starts to cry.

"Oh please stop.Please just stop.

She slumps over the desk.And when he finishes, she continues to lay there.She was unable to move.She raised her head slightly and looked at him.

"Go fuck a nun."
He thinks he is finally getting somewhere with her as she starts crying. He knew he could break her. He looks at her ass and knows she wont want to sit for a good while. Then she opens her smart ass mouth again.
"what was that? Kelso begain wailing on her ass even harder than before. This was definately pushing the limits of what he was supposed to do but luckily he had the connections that it didnt matter."Stop crying slut you know you enjoy this all sluts do. It wont make me stop again" He brought down one last swat on her bright red ass even harder than he ment to breaking the paddle over her ass. He looked to make sure there were no splinters and had to admit there was something sexy about her round red ass. He quickly dismissed it from his mind though.
 
Kelsey screams out in agony as the paddle breaks.SHe slumps down again and lays there.She has tears trickling out of her eyes when the door opens and Sister Judy walks back in.

"Headmaster Kelso, are you done with her yet? She has a class in 5 minutes.Or do you want me to inform her teacher that she won't be there."
 
effmyass said:
Kelsey screams out in agony as the paddle breaks.SHe slumps down again and lays there.She has tears trickling out of her eyes when the door opens and Sister Judy walks back in.

"Headmaster Kelso, are you done with her yet? She has a class in 5 minutes.Or do you want me to inform her teacher that she won't be there."
He looks down at the sobbing mess below him. Part of him thinks about continuing the punishment to completely break her but decides her sitting in her chair will be very good punishment.
"Ok Sister Judy thanks for letting me know. Take her to class and make sure she sits still in her seat. Oh and on the way back can you get me a new paddle for my office this one was a little old and weak. If she is any more trouble let me know."

They leave his office and Kelso starts to reorganize his desk to get back to work but keeps getting inturrupted by the mental images of her bare ass and ample cleavage. If only he had met her outside of school he thought.
 
Kelsey follows Sister Judy out.As she reaches the door, she turns and smiles.Lifting up her skirt in the back.

"I'll be back."

She walks to class and sits down on her painfully sore bottom.When Sister Judy leaves for a telephone call, Kelsey sneaks out with another girl and they make out under the bleachers.
 
effmyass said:
Kelsey follows Sister Judy out.As she reaches the door, she turns and smiles.Lifting up her skirt in the back.

"I'll be back."

She walks to class and sits down on her painfully sore bottom.When Sister Judy leaves for a telephone call, Kelsey sneaks out with another girl and they make out under the bleachers.
The Headmaster knew he was going to have some trouble with this one. No matter how bad the punishment she was going to rebel. He thought about trying to bribe her but realized it most likely wouldnt work and even if it did he wouldnt be doing her a favor at all. She had to be ready for the real world eventually. He knew he would have to break her to cause her to submit.
As he thought of ways to go about this he kept having mental flashes of her bare ass and ample cleavage. He couldnt shake the images from his head and felt himself getting arroused. He knew he had to shake it so he decided it was time to enjoy one of the perks of being a headmaster at such a high class private school and went to his private bathroom and started a cold shower. After a good long shower he was ok and dried off before getting back in his suit. He was finally able to focus on some of the paper work he started earlier that morning.
 
Kelsey waved at the girl she had had her make out session with and proceeded to walk away from the school.SHe headed downtown.Cars beeping as they drove by.She just smiled and wiggled her hips more.She found herself in front of a convenience store and walked inside to buy some cigarettes.
 
The headmaster looked up at the clock and realized he had let the day fly by without realizing it. He started putting away his paperwork and tried to decided what he was going to do for the night.
 
Kelsey starts heading back to the school, to board the bus.When she gets there she realizes it's past the time of school letting out and the bus has already left.She sits down on the steps and lights up a cigarette.
 
Kelso gathers his things and locks his office door. On the way out he says good bye to the janitor that is still working his round. He looks at his watch and realizes he has a few hours before poker night with some of his friends. As he walks out the from door he sees Kelsey sitting on the front steps smoking.

"Miss Johnson what are you still doing here? Just cant get enough of the school that you wanna stay after hours? You know I am sure Sister Mary could find something for you to do around the grounds"

He figured the day was over and he could be just as sarcastic as she was. He noticed her smoking but since school was out and she was outside there was nothing he could really do about that.
 
Kelsey looked up at the Headmaster.She could tell he liked how she looked.She stood up.

"I missed the bus.What are you gonna spank me over your car next? Or maybe you'll bend me over the hood and shove it in my ass?"

She smiled, moking angelicness.

"No, you'd be too pussy to do that out here."
 
effmyass said:
Kelsey looked up at the Headmaster.She could tell he liked how she looked.She stood up.

"I missed the bus.What are you gonna spank me over your car next? Or maybe you'll bend me over the hood and shove it in my ass?"

She smiled, moking angelicness.

"No, you'd be too pussy to do that out here."
At first he just wanted to gag her so he wouldnt have to hear her anymore. Afterall his day was over and he didnt want to have to deal with the brat until tomorrow. He thought about just leaving her there but decided to be the responsible adult and offer her a ride.....after a remark of his own.
"No reason to spank you at all. Besides I think you enjoyed that a bit too much anyway. Well according to your file you live on the way to my place. Do you wanna ride?"
 
Kelsey rolled her eyes and followed him to his car.She got in and quickly rolled down the window.Headmaster Kelso was such a stiff, it seemed like he never really let loose.
 
The Headmaster jumped in the driver's seat of his european sports car and buckled up. Out of the corner of his eye he could see her skirt riding up her firm thighs again. As soon as he started the car the 15in sub in the back of his car started hitting hard to the rap cd he had playing. He could tell that Kelsey was more than a little surprised. Then he pulled out of the parking lot and took off flying down the road.
 
OOC I think I am going to have to find a new Kelsey to continue this thread. Any takers
 
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