Miss Featherly Ch. 01

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A professor's tutoring session is different than most.
4.5k words
4.53
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Part 1 of the 2 part series

Updated 09/28/2022
Created 05/22/2014
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Shysquirter
Shysquirter
1,046 Followers

The following is a work of fiction. All characters are at least 18 years old.

*****

Margarette had considered herself a refined lady for as long as she could remember. Her parents were set up with old family money to which they added from their lucrative careers as attorneys.

Perhaps because they took her to operas and classical concerts from a young age, she was much more comfortable in formal attire than anything else; she would never be caught dead dressed casually.

The body was a temple in Margarette's mind and should be adorned elaborately like all of the great cathedrals the world over. She was continually updating her wardrobe making sure nothing ever showed any wear. Her clothes were always fashionable, albeit quite conservative.

Her parents met at Penn State during their undergraduate studies. Dad became a district judge just as Margarette was going off to college. She chose to attend Temple, a decision that brought the confused ire of her parents.

She said she wanted to go to a smaller school that was more academically minded, but deep down she just wanted to get a rise out of her parents. While she appreciated all that they have given her, she felt that they valued their careers more than her.

Her college experience was pretty normal, if not boring. She had a small group of friends with whom she loosely hung out, but she never really got close to. Most people took her to be a bit of a snob. Although she was polite, she always seemed to give off a vibe that she thought she was better than everyone.

She would smile and carry a polite conversation with anyone, but it was like when a small child tried to seem important to adults. There was nothing you could say that could enlighten Margarette.

She got great grades in school and actually graduated Summa Cum Laude. She attended Pitt for her Masters degree, and then got a job at George Washington University, where she taught Freshman composition with classes that averaged about thirty students. She was a tough teacher, but the students who made it through her class and survived, tended to do better in their scholastic careers. She harshly hammered into them a deep respect for the English language.

The rest of the faculty respected her, but she never made any close friends on campus. Even with her lack of a PHD she still seemed to hold herself in higher regard than her peers. She got the job because her collection of short stories sky rocket up the New York Time's bestseller list. It peaked at number seven, but stayed on the list for months. The short stories were aimed at an adolescent audience and were unique in that they were very plain. They were simple tales of mundane everyday teenage life, but there was something in the stories that teenagers could really get behind. No one knew if she was working on anything else of late.

As to her personal life, it was very similar to how it had always been. She would occasionally get serious boyfriends, but they never seemed to last very long. All of her boyfriends were very similar. They were good looking, successful men that became completely subservient to her.

Eventually she would slowly drift away from them. It was as if she was just simply getting bored. They never talked bad about her after a relationship, and they never quite seemed the same either.

She ran her class like a drill sergeant. If anyone would even whisper out of turn she would berate them in front of the whole class. Most of her students loathed her at first, but typically, as they saw their own writing improve. While they had a general disdain for her methods, recognizing their own development and improvement in their writing skills, they realized it was for their own good.

John was failing her class badly. Too many late nights and too little effort, he had dug himself into an academic hole, with the realization of his impending failure imminent. John was desperate. If he failed her class he was in danger of losing his lacrosse scholarship. One late night he was telling his good friend Billy about his predicament over a multitude of beers when Billy's eyes lit up. He had been in a similar situation when he was a freshmen and one of his older fraternity brothers told him about secret "tutoring" sessions that Miss Featherly did for certain students.

After multiple reassurances that John would not tell anybody what Billy was about to tell him, Billy said that if John would do everything that Miss Featherly asked of him, he could pass the class. All Billy would say about the acts he would have to perform were that they were sexual in nature, and Miss Featherly would be in total control of the situation.

John was already a few sheets into the wind, and he saw no other possible way of passing her class. The thought of having to please her for a grade aroused John greatly. It seemed liked a win win situation, so he decided to go meet her in her office the very next day.

-

"Yes Mr. Williams?" Margarette didn't even look up from her book as she addressed the young man who had just entered her office.

"Hi Miss Featherly, I just wanted to talk to you about my grade." John seemed extremely nervous.

Margarette put down her book and studied the young man He was dressed in jeans and a T-shirt that was struggling to contained all of his muscles. His blonde hair was a mop of disarray on top of his head. She wondered when was the last time he had washed it. He did have a cute charm, despite his lack of grooming. White teeth shown from beneath a radiant smile and his sheepish blue eyes were simply lovely.

"Lets us talk then." She folded her hands on top of her large mahogany desk.

"Well," The boy continued timidly. "Grades are coming up, and I don't think I can pass your class. I mean, even if I get an A on the final, I still will have a D at best I think."

"Mr. Williams, if you got an A on the final, I would be quite surprised. You haven't gotten anything higher than a D so far if I recall, and you rarely even turn in your work. It seems that you are having a bit too much fun your freshman year of college. Am I right?"

His eyes opened a bit wider by her accusations, but she had nailed it. He wasn't sure if there was a time when he wasn't hung over or high in her class. "Yes Miss Featherly, its just that college is so different than high school."

"Many more temptations aren't there?" She looked up from her book and inspected him. Her eyes looks inquisitive behind her glasses.

"Yes, thats for sure."

"First of all you will address me with respect. i\It is Yes Miss Featherly, yes ma'am, or yes professor."

"Yes Miss Featherly."

"Secondly, what have been the greatest temptations so far for you?"

"Parties definitely. Miss Featherly."

"And have you been devoting your time to the pursuit of young coeds?"

"Huh, oh, yeah."

"Oh yeah? Did you mean to say, 'Yes, Miss Featherly?'"

"Yes, I guess I did ... I mean, yes, Miss Featherly."

"So what do you want to discuss about your grade Mr. Williams?" She sat arms cross, under her lovely breasts, while she was looked up at her student. She hadn't invited him to sit yet.

"Umm, well." Nervously he ventured, "I came to ask for some private tutoring. My friend Jack, Jack Peacock, told me that you offered private tutoring sometimes."

Miss Featherly's raised her eyebrows. He had piqued her curiosity. She now studied the attractive young man before her a bit more intently. She slowly rose from her seat and walked around her large desk and stood at the side of the young man studying him further. John was captivated briefly by her killer legs that suddenly came into view as she emerged from behind her desk.

"Jack Peacock, yes, I remember him. He became a fine student after some work." She walked behind her pupil. "Has Jack filled you in on the particulars of my tutoring?" John began to turn his head to answer, but suddenly he felt his teacher's surprisingly strong hands holding the sides of his head in place.

"I did not ask you to turn your head Mr. Williams."

"I am sorry." There was a long awkward pause. "I am sorry Miss Featherly. I am just nervous. Yes he told me how it worked. Come to your office office at the proper time, use the correct door, and make sure that I make all of the proper preparations. If you agree to tutor me that is."

Miss Featherly's hands slowly slipped from the sides of his face down to his powerful shoulders. She kneaded them as she thought. Suddenly John felt her warm breath on his neck and then his ear, as she instructed him in a sultry whispered voice.

"Your first lesson will be tomorrow. If any of your preparations are off, then the tutoring is over and you will fail. I think it will take three tutoring sessions to get you to pass with an C. Four sessions will get you a B, and five session for that A. That is if you are a good student." Her hands slid down his shoulders, along his sides, and then came to rest one on each of his firm ass cheeks. She gave them a little squeeze.

"Yes Miss Featherly thank you. Thank you so much." John's voice climbed an octave as he felt a hand start to stroke the front of his pants bringing his semierect member to a painfully rigid state almost instantly.

"Looks like you are going to enjoy this session as much as I will. Just remember to follow precisely all of the preparations Jack has told you to the letter. Any deviation will end our little agreement." She continued to stroke him. "Now I am going to leave you so you can collect yourself. It wouldn't be proper for you to walk out of my office with this ailment." She gave his cock a strong squeeze.

"I will see you tomorrow." Miss Featherly clicked her heels across the tiled floor as she left the room with John's mind spinning, but mesmerized by her beautiful stockinged legs.

The next night John was extremely nervous as walked up to the dark administration building. The brick walls still radiating heat from the day. The massive building looked completely deserted and ominous. Only a few hallway lights were still on. John found the door that was open a crack and let himself in. He scratched nervously at his groin. Minutes earlier he had shaved off all of his pubic and chest hair as instructed. His outfit was also carefully chosen. Jeans with no rips, no hat, collared shirt, closed toed shoes, and no underwear.

John's friend had told him about Miss Featherly's strict instructions on not sharing what went on in her tutoring sessions. Students were only allowed to recommend their closest friends to her. John pressed his friend on what the tutoring sessions entailed, but Jack was reticent to John's inquisition. All that he shared was that if John did everything Miss Featherly asked, he would get the grade he was seeking and have a good time in the meantime. He also made John promise never to tell anyone about what was going to take place.

The hallway was so quiet that all that John could hear was the near silent squeaking of his shoes on the linoleum tiles. All the offices were dark except one. At the end of the hall was Miss Featherly's office and an orange glow leaked out from under the door. He walked up to the door and was about to try the handle when he remembered about the knock. Four knocks firm but not too loud, each spaced out by three seconds. He waited two minutes until it was exactly 10.02pm, as instructed.

Knock.

He stood counting the seconds in his head, wondering what he was getting himself into.

Knock.

Only silence responded to his rapping.

Knock.

Last chance to turn and go home.

Knock.

The last knock hung in the air for a couple of seconds before he heard,

"You may enter Mr. Williams." The warm voice of Miss Featherly called.

He opened the door and stepped inside. Everything was the same as the previous time he was there except the light was much softer. He glanced at a lamp to his left and noticed that it had a red silk scarf draped over it.

"It is not polite to have your eyes explore a room upon entering it. It makes you seem weak and nervous. Always keep your eye contact with the one with whom you are speaking." Miss Featherly spoke softly but sternly.

She sat behind her desk again. She had on reading glasses, and her brown hair was up in a bun. She had on a white blouse that was buttoned all the way up. It seemed almost too tight for her. Her breasts, while not large, strained against the fabric.

"Yes Miss Featherly, I am sorry." He made sure to keep eye contact despite how nervous he was.

"There will always be mistakes in the learning process, that is to be expected. You are perfectly on time, that is very important."

"Before we begin I must make it perfectly clear that you can never tell anyone what is about to happen. If after our tutoring session, I deem you of good judgment then and only then can you recommend my tutoring to a close friend. Do you understand?"

"Yes Miss Featherly."

She looked him up and down like a piece of meat and she actually licked her her lips as she thought. "Not my favorite pair of jeans, but thats ok. They will look fine on the ground soon enough."

"Then we can begin. Please take off your shirt and place it on top of that file cabinet." She pointed with a wooden bookmark.

John did not hesitate. He quickly removed his shirt revealing a well toned chest and a flat stomach that had subtle hints of a six pack.

"Very nice Mr Williams." Margarette said as she stood up. John let out an audible gasp at the site of her. While she was dressed very conservatively from the waist up, she wore black stockings held up by a garter, and a lacy black g-string. Her legs were well toned and tanned, and she wore tall, black high heels, that accentuated her wonderful lines.

She walked around her desk and stood behind John.

She gently placed her hands on his chest and moved them softly up and down his chest and stomach.

"So you approve of my outfit?" She whispered in his ear.

He took a hard swallow before answering almost breathlessly, "Yes, very much. Your legs are stunning."

"Thank you Mr. Williams. I believe one's outward appearance speaks volumes about one's character. Judging from how well you tone your body I gather you are a hard worker." Her hand continued to gently stroke his chest and stomach. With each pass it crept lower and lower on his abdomen.

"A hard worker when you set your mind to it, and so far you have not set your mind to passing my class." She purred in his ear. "God, I love freshly shaven flesh. It is simply intoxicating." She dropped one hand to the front of his jeans and began to rub his growing cock.

"What have you been focusing on rather than studying for my class." She asked as she kept rubbing his chest and cock.

"Uhh. I, uhh. I have been partying." He struggled to speak while she rubbed him.

"What does that mean partying?"

"Drinking and listen to music."

"Is that it?"

"Sometimes I smoke pot."

"Bad boy." She tweaked his nipple roughly. "We will address that issue later. How about girls?"

"Yes Miss Featherly, I do mess around with girls."

"Be specific Mr. Williams." She was lightly scratching his chest with her long red nails.

"I like to have sex with girls."

"How many have you scored with since you have been here?"

"Uhh, I don't know. Ouch!" She stopped rubbing his now hard cock and pinched both nipples roughly.

"Ok, Ok!." She could hear him counting to himself. "Six, I have had sex with six girls since I have been here."

"Good boy, now we are getting somewhere. Did you fuck all of them." She reached down and unbuttoned his jeans. Slowly she unzipped him. She reached in and grabbed his rigid cock.

"Did you ram this big cock of yours in their hot little tight cunts?" Her hand was cool on his skin. She sucked in air by his ear.

"Yes, yes Miss Featherly." John barely mustered..

"It must be uncomfortable with your large hard cock crammed in your jeans." She pulled out his cock swiftly. It was a thick cock. Its veins were bulging as blood raced into it. She began to stroke it slowly. The area above his cock was cleanly shaven as long as his shaft and balls. It was almost comical to have such a large member devoid of hair.

"I just love young cocks. So smooth and hard. Was this the first time you shaved it?"

"Yes...Uhh..Yes Miss Featherly." John struggled to speak as he was slowly jerked into nirvana.

"Was it scary for you?"

"A little scary at first, but then it was kind of, exciting."

"Good boy, I like your honesty." She kept stroking and let his pants fall to his ankles. "And such a nice firm ass."

She gave him a couple of light slaps and then squeezed his cheeks as if she was checking a melon for ripeness. The sensations were too much for the young man. His cock twitched in her hand and immediately erupted a torrent of sperm onto her desk.

John felt as if he was going to pass out from his pleasurable climax. His eyes were shut as he relished the feeling of the orgasm. Finally he was roused to reality by Miss Featherly's disciplining voice, and she did not sound happy at all.

"Shame on you Mr. Williams. You have much to learn. You must always ask for permission to cum," she thundered. "How can you expect to please a woman if you act like a common 'Two Pump Chump'?" Her hand was still on his member expertly extracting the last drops of seman from his still huge cock.

"Look at the mess you have made of my desk." He opened his eyes and saw that a large puddle of his creamy semen was pooled on the desktop. "I think it might be prudent to cancel our sessions. Maybe you are a hopeless creature, unable to be disciplined and learn the finer points of my lessons."

"No, please Miss Featherly. I was just overwhelmed. I have never experienced pleasure like that." The pause that followed his statement seem to last forever.

"Fine, we will continue. Bend over Mr. Williams."

He paused for a second, and then immediately bent over her desk. He was looking down for a cum free spot to rest when she shoved him down onto the desk. He could feel his hot cum all over his chest and stomach.

"Now you stay like that and think about what you have done wrong. I will be back." The next thing he heard was her high heels clicking on the floor, then the door opening, closing, and her walking down the hall. He did not dare move.

He lay on the desk for so long that his legs began to cramp up, still he didn't dare to move. He needed to pass her class, and he would do practically anything to do that. On top of that, he had the added intrigue of what kind of sexual adventures lay ahead of him if he played along. He was curious to see where this adventure would take him.

After what felt like forever, he finally heard Miss Featherly's heels click clacking in the hall. He heard the door open, and her walk up to him. Next he felt her soft touch on his back. Slowly stroking him up and down with her long delicate nails.

"Very good. You knew not to move. I would have known if you had disobeyed me." She began to stroke his ass very gently. One finger fell between his cheeks and teased his crack and then his asshole.

"But since you obeyed me, your punishment will not be very severe." Her hand dropped to his balls and she traced them with her fingers. Next, she walked to the front of the desk and sat down. She placed a large yard stick down on the desk. She reclined in the chair and put her stockinged feet up. Her toned legs were demurely crossed as she spoke to John.

"You are a handsome devil Mr. Williams. We can have a lot of fun together if you are a good student. Would you like that?"

It was awkward for John to look at her, bent over with his head on the desk, but he dared not move.

"Yes Miss Featherly."

He strained his neck to watch her sensuously run her hands up and down her sexy legs. He could feel himself beginning to get hard again.

Shysquirter
Shysquirter
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