Blackmailed MILF

As Sheila Moser, Assistant principal and Guidance Counselor at LHS, knelt naked in her office sucking the cock of one of her students, she wondered how she got herself into this dangerous position and thought back to when it started.

About twenty years earlier she had been the best looking girl in her senior class at LHS. She was voted Homecoming queen and Senior Prom queen and a year after graduation she was elected the region's Festival Queen. Her long wavy black hair framed her classically beautiful face. Dark eyes and full lips along with a curvy body on a five foot four inch frame, she was difficult to resist. But being told you were gorgeous your whole life can lead to conceit and that is exactly what happened. On the outside Sheila would smile and give out an occasional compliment to others but on the inside she thought little of anyone but herself.

As a result when she finished school and the richest man in town showed interest, Sheila jumped at the opportunity. After a short affair he left his wife when Sheila told him she was pregnant, though he never discovered it wasn't his child. Sheila enjoyed spending his money and living in the largest house in town but a few years later when he died of a heart attack she was surprised she had spent most of his money and that he had no insurance.

Sheila secured a job at LHS as assistant principal which required her to discipline the students and hand out punishments, a role she was well suited for because she was thought to be mean by the majority of the students. She was also made guidance counselor even though she did not have the qualifications. What she had was the ability to seduce the principal and superintendent into giving her the position in exchange for a few nights each of romance.

Thus she was able to pay her bills and raise her daughter Sierra who turned out to be as attractive a young woman as her. But about the time that Sierra reached eighteen and her senior year at the school, Sheila looked in the mirror and noticed the signs of age creeping up on her. Lines on her face, a few extra pounds and other things that might not have been obvious to others scared Sheila to death and now she had been having trouble sleeping because of this fear. She had always been dependent on her looks and now, she thought, they had begun to fade.

Possibly due to her fear of losing her looks Sheila had started to have dreams about one of the students that her daughter Sierra had been dating. (Sierra rarely dated just one boy at a time. She liked to see them compete for her affection.) Jason, like his Greek namesake, had the body of a Greek god. Now a senior, he was an athlete and starred in three sports. His long, curly blonde hair and blue eyes stunned the female population of the school, including the teachers and staff.

Even though he could get just about any girl at the school, he wanted Sierra. But she played head games with him and strung him along while going out with other boys. When he would come to their door Sheila couldn't help but drool over him. True he had an eighteen year old mind but she ignored that and concentrated on his looks. When Sierra would invite him to share the pool with her, Sheila would go to a window and stare and fantasize about running her hands over his sculpted body. At six feet tall and one hundred seventy pounds there was little fat on him.

Sheila herself had become frustrated with dating. There were few men around that she felt were worthy of her. She dreamed of having a man like the ones she had in her youth. Though there were many students at school who gave her lustful looks, Sheila knew that indulging herself with them could lead to trouble if not prison. As a result of all her frustrations Sheila began to drink.

When Sheila would watch Jason from the window, strip down to his trunks by the pool she often had a drink in her hand and she could feel tingling in all the right places in her body. So when the day came for Jason to enter her office for guidance counselling, Sheila was a bit nervous. Before her stood the boy she had been dreaming about lately. It didn't matter that he was young enough to be her son; she could feel her blood pressure rise.

It was during this counseling session that Jason noticed out of the corner of his eye that Sheila was glancing at his crotch. Sheila was chewing gum but Jason could still smell the whiskey on her breath. Even though she was much older than him she still looked good and the idea of fucking a MILF like Sheila was not an unattractive idea to him. Although both were thinking similar thoughts nothing happened that day.

It wasn't until the following week when Jason showed up at Sheila's house right after school while looking for Sierra that trouble started. Sheila had just consumed almost a half a bottle of her single malt scotch when she heard the doorbell ring. She was wearing nothing but a red silk robe that hung just to her knees. She quickly put on some shoes and walked to the door.

Jason asked for Sierra and Sheila replied. "She's out and won't be back till late tonight." Then Jason asked to use her bathroom. She agreed. Jason didn't want to leave. On one hand he was angry that Sierra was probably out on a date with one of his rivals and on the other hand he didn't want to leave the sight of Sheila in a slinky robe. She was obviously nude underneath it and he could see the imprint of her erect nipples under the material.

As Jason stood in the bathroom pretending to be using it he suddenly realized why he was so attracted to Sheila. She had an uncanny resemblance to his favorite porn star Lanny Barbie. She could be her older sister, he thought. Of course Sheila, if you had asked her, would have no idea who Lanny Barbie was but most of Jason's friends did. Jason quickly thought out a plan.

Jason asked Sheila if he could swim a few laps in the pool. Sheila was pretty drunk so she agreed but stated that she would have to watch since it was a house rule that no one could swim alone because of the danger of drowning.

When they got out to the pool Jason stated that he had no trunks with him and asked if he could swim in his underwear. Sheila paused, took another sip of the whiskey and agreed. Then she sat in a chair and watched Jason strip trying not to be obvious about her enjoyment.

Jason's briefs quickly became transparent after diving in the water. As he made laps his breaststroke revealed solid buttocks and his backstroke revealed a bulging package. Sheila put on her sunglasses to hide her gaze. The more she saw the more she drank until she was tempted to jump in the pool herself. She hadn't had sex in over six months and she was going out of her mind at the show she was seeing.

When he finally came out of the pool he might as well have been naked. Sheila could see everything and her mouth was watering. Jason stood there next to the pool, his body all wet and every muscle pumped with blood from the exercise. He began to wipe off the water with a towel and then suggested that he couldn't wear his wet underwear under his clothes. He said, "Could you turn around while I change?"

Sheila stood up and turned her back as Jason peeled down his underwear. Then as she waited for his okay she felt his presence behind her. She pretended not to notice. Suddenly she felt his breath and then a kiss on the back of her neck. She stiffened but didn't pull away.

Soft, breathy, whiskey soaked words slowly crept from her mouth, " Jason...? Jason... don't." But the tone of her voice said yes.

Then his strong, damp arms encircled her, caressing her and pulling their bodies together. Sheila could feel a firm erection pushing up against her buttocks. She took one last sip of the whiskey and the glass in her hand fell to the grass beneath her. Passion and sexual frustration had taken control and there was no turning back. The fantasy she had dreamed of for months had taken control of her mind and body. She wanted what was behind her, pressing up against her back.

As Jason nestled his mouth against her neck, pushing aside her hair she could feel his hot breath on her ear. She kept her hands at her side but they began to tremble revealing what was in her mind. Jason knew that when Sheila did not turn quickly and push away that he had received the green light he wanted. He reached down from behind her and undid the tie at her waist and the robe fell open. Then he slid his cool hands inside the robe, feeling the heat of her body. His hands slid up and down her stomach until they rose to her breasts and encased them both. Her breasts weren't as firm as the teens he dated or as large as a porn stars' but they were large enough to fill his hands and firm enough to excite him even further.

Sheila's head fell back and her breathing began to speed up as he massaged her mounds. She knew this was wrong but her sexual passion was so strong that she convinced herself she would find a way around the trouble. That's when she felt Jason's hands peel off her robe. Sheila stood there completely naked except for her black high heels.

Jason turned her around and quickly embraced her. Neither spoke before their mouths touched and went into a deep kiss. Jason's hands descended to Sheila's ass and her hands roamed the muscular back of the teenage boy. She could immediately tell by his kiss that he was no beginner at this game. Her hands then descended to his ass and she tried to squeeze what seemed like marble mounds, as if he were a statue in a museum.

Sheila took an opportunity to look down to spy his erection. It stood out hard and was clear of any hair, something the swim team did on all their bodies. The only hair on him was the curly blonde hair on his head which still dripped onto her body.

Jason moved Sheila down onto a padded mattress used for sunbathing next to the pool and he lay on top of her. The water from the pool still on his body lubricated their skins and they slid back and forth as they began exploring each other with their mouths and hands.

Sheila wanted to continue the foreplay but like most teenagers Jason was impatient and soon entered her pussy with his six inch cock. Sheila reacted moaning with pleasure as he shoved it in the entire way. Sheila's cunt was juicy from anticipation and there was no resistance. Jason propped himself up on his elbows and leaned down and gave Sheila another deep French kiss as he began to piston his cock back and forth in her pussy.

Jason was in a bit of a daze as he realized he was fucking the assistant principal and the mother of Sierra, but he and the boys at school had often referred to Sheila as a MILF they all wanted to fuck even though she was often mean and bitchy to the students. They were always saying, "She couldn't bitch if you put a cock in her mouth."

The drops of water falling on Sheila's face mingled with her tears of passion. She reached down and pulled his ass toward her pussy helping Jason lunge forward on each thrust. She was quickly nearing an orgasm brought on more by her anticipation. She began scratching at Jason's back and ass until the stars burst in her eyes and she bit down on Jason's earlobe. Of course Jason had no idea what was going on with her and just continued to thrust away toward his own climax.

After a few more minutes he came and Jason filled Sheila's cunt with his creamy load. He collapsed on Sheila, panting away as if he had just run the fifty yard dash. As much as Sheila was enjoying herself she was disappointed that the whole love making session had lasted less than ten minutes. She wanted more.

Jason pulled his still hard cock from her pussy and stood up. Sheila stared at it, all wet with their combined juices and swaying beautifully before her.

"That was fun, Mrs. Moser. We got to do this again. But right now I got to get going to practice."

Sheila was quickly regaining her composure when she replied, "Jason, we got to keep this a secret, just between you and me."

"Don't worry, I won't tell Sierra."

"I don't mean just her, I mean everybody. No one can know or we could both get in real trouble."

"Both of us? Even me?"

"Yes. Both of us."

Jason agreed and quickly dressed and was on his way but by the time he was gone Sheila had begun to worry. She didn't like his response, "Both of us?" It sounded odd to her as if he thought maybe only she could be in trouble. Sheila's dreams suddenly changed from fantasies about Jason and his body, to nightmares about going to court or even prison.

It was the following week that she noticed Jason's name had been added once more onto her schedule for counseling at school. Sheila began drinking vodka at noon for she was very uncertain about their 2:15 appointment. She was nervous about the two of them making contact on school grounds even though she was a school counselor.

Jason walked into Sheila's office at the scheduled hour with a big smile on his face. He had already received a full athletic scholarship even though his grades were marginal and really didn't need counseling. He closed the door behind him and closed the safety latch that had been added by Sheila's request in case of a school shooter attack. Jason put his books on her desk and just stood smiling. Sheila spoke up.

"What can I do for you today, Jason?"

He didn't reply but just stood there smiling. Sheila glanced down at his crotch and could see the outline of an erection growing. Sheila swallowed and repeated her question. When he didn't reply she stood up.

"Jason, listen, I think it is best that we forget about last week."

"Forget about last week, are you kidding? No way!"

Sheila couldn't decide whether to play hard with him or try a softer approach. She decided to play it soft.

"Jason, I really enjoyed last week but...we can't do anything here and-"

"Why not? The door is locked." Sheila panicked and tried a lie.

"I have other appointments later."

"A blow job won't take long."

Sheila was startled by the words being spoken in her school office but she quickly saw an opportunity.

"Jason...if we do this...you've got to promise me it will be the last time."

Jason lied and agreed. Sheila actually had mixed feelings for she was eager to once more get a hold of Jason's cock even though she would prefer that they fuck. As she came around the desk Jason spoke up.

"Take off your dress."

"What?"

"You don't want to get cum on it, do you?"

Sheila paused and thought he was probably right. She turned around and looked out the second story window. There was nothing to see but the large oak tree with its leaves starting to turn. She began to unbutton her dress. Sheila often wore dresses that buttoned down the front for she would occasionally unbutton the top or bottom button to flirt with a teacher or staff member.

As she turned around she removed her dress and put it on the chair. She glanced once more at the lock on the door to make sure it was secure then she walked over to Jason who had already unzipped and taken out his rock hard cock. Dressed in just her bra, panties and hose Sheila leaned into Jason for a kiss. After a little passionate mouth action Jason put his hands on the sides of her head and pulled her face away.

"We don't have a lot of time; I've got a meeting with coach in five minutes."

With that he guided Sheila to her knees where her face was met by his throbbing cock. Sheila was hoping for a little romance in an effort to help control Jason but realizing her situation and time shortage she quickly took Jason's cock into her mouth and began sucking him off.

Sheila had gotten out of the habit of giving blow jobs for she had usually persuaded the men she dated to go down on her instead. She hadn't given regular blow jobs since high school. Even her husband had been lucky to receive them except at moments when Sheila wanted a special favor, like a new car.

But just like riding a bicycle she quickly remembered her old technique and began licking and sucking Jason's hard cock. Jason eagerly watched his pink cock disappear into the assistant principal's wet mouth, then, pulled it out only to shove it in again, deep into the hot, juicy mouth.

As he pumped away at Sheila's mouth Jason glanced out the window and thought that if someone were to climb the tree they could see what was going on in Sheila's office. It made him ponder that it might be nice to record their activity for posterity or even maybe show it to his buddies.

As Jason was considering this Sheila was busy, anxious to get Jason off as soon as possible for she didn't want someone knocking on the door and finding it locked. Her mouth was very wet and she could feel the juices running down her chin and dripping onto her chest. Sheila pulled Jason's cock out of her wet mouth to kiss and lick the head then jam it back in as far as she could.

Jason checked his watch and seeing he had little time left took hold of Sheila's head and began fucking her mouth. This didn't make Sheila happy but she relented and allowed Jason to continue for several seconds. Then he surprised Sheila and pulled his cock out. Sheila opened her eyes wide in surprise just in time to catch the first spurt from his cock. As she opened her mouth to protest another spurt entered it causing her to begin coughing while the last three giant spurts hit her face and hair.

Sheila sat back onto the floor, still coughing and recovering from the deluge as she heard Jason speak.

"See, aren't you glad you took off your dress? You better get dressed. I got to go."

Sheila wiped her eyes. She was in a bit of a shock and didn't quite know what to say. She was tempted to yell an angry word at Jason but thought she better just be quiet and quickly get dressed. She had only just a few buttons done when she heard the latch unlock.

"See you in a couple days, Mrs. Moser." Then the door opened and quickly closed leaving a half dressed assistant principal covered in cum and after pulling out a small mirror and seeing the mess on her face and hair she wondered what she had gotten herself into.

She walked over to the door and hit the lock then went to her desk and sat down. Out of a drawer she pulled a partial bottle of scotch and opened it. As she took a drink with one hand the other hand pulled up her dress and slid her fingers into her panties. She was done for the day and she needed to think and understand what had just happened and why she was so excited about being used. By the time the last bell had rung she had finished the scotch and had climaxed three times.