Blackmailed MILF Ch. 02

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A teen continues his control over the milf asst principal.
5.1k words
4.25
190.6k
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Part 2 of the 2 part series

Updated 10/21/2022
Created 12/20/2014
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henryo
henryo
162 Followers

Sheila had been having trouble sleeping for the last two weeks. Arguments with her daughter Sierra and nightmares about Jason had taken a toll on her rest. Of course having an eighteen year old daughter often causes sleep loss but most people don't have to worry about affairs with students that could put them in jail.

In reality the truth was she was as much addicted to sex with Jason as she was to booze. She only used the blackmail as an excuse to fuck him. She actually loved it and got tingles every time she saw him in the school halls, picturing his naked body as she first did weeks ago next to her pool. But the nightmares still came.

One nightmare in particular was recurrent for Sheila. It started with her walking into a crowded courtroom alongside a greasy lawyer she knew as her defense counselor. Don was a middle-aged ambulance chaser and could turn the stomach of any woman he looked at. It wasn't that he was that ugly but he had no class at all and would often stare at a woman's chest or legs with a lustful grin, uncaring of how uncomfortable he made the woman.

The Prosecutor in the dream was also a problem for Sheila. Seated at the prosecution table was an attractive blonde, Tracie Jones, an old classmate of hers who had also been a competitor in school for everything, including boys. Sheila remembered Tracie being a lawyer but thought she was practicing in a different state.

After taking her seat at the defense table Don immediately pushed his chair right up against hers and put his hand on her leg under the table. Sheila pushed his hand off her leg but he just put it back on. Even though it was distracting Sheila decided not to fight him. Don would stand up to make an objection and as soon as he sat down he put his hand back on her leg, moving it up and down her thigh.

Sheila looked around at the crowd in the courtroom and saw all kinds of people she knew, teachers, staff, students, old acquaintances, and all of them seemed to be staring at her and enjoying what they were seeing. It didn't seem to be a normal trial crowd but more like a sporting event. The people were smiling and laughing and whispering in each other's ear as if there were a joke being passed around.

When she turned back around she saw that Jason was on the stand and Tracie was examining him.

"Have you ever seen Sheila Moser, the defendant, naked?"

"Yes."

"Tell us about it."

"It was the first time we had sex. It was right after I practiced swimming in her pool."

"In order to help prove you actually were with the defendant when she was naked, could you tell us if there are any distinguishing marks on her body that cannot otherwise be seen when she is dressed? Any tattoos or birthmarks, etc?"

"No, none at all."

"And did you get a good look at her body?"

"Every inch of it."

Tracie turned to Sheila with a sly smile and then addressed the judge.

"Your honor, in order that the jury can decide if this 'very young man' is telling the court the truth we would like the defendant to show us the evidence."

The judge replied in a very 'matter of fact' way.

"Very well, of course. The defendant will now stand and reveal the evidence."

Sheila turned to Don and asked what they were talking about. He informed her that she must stand up in front of the jury and take off all her clothes. Sheila was outraged and she jumped up and yelled at the judge.

"This is ridiculous. I'm not taking off my clothes here in this courtroom!"

The judge replied. "You either take them off or I'll have the guards take them off for you and in addition I'll hold you in contempt."

Sheila looked at her old rival Tracie who was smiling, just as was about everyone else in the court. Then she looked at Don once more who was trying to hide his smile.

"How can they do this to me?"

"He's the judge. You better strip or you'll end up in jail and I don't think you'd enjoy it there."

An angry and upset Sheila stepped around the defense table and walked to the front of the jury box. The entire courtroom was watching as Sheila began unbuttoning her blouse. As Sheila undressed she glanced around the room at the smiling faces. Tracie was sitting on the edge of her table with the biggest smile of all. Even the judge had a slight grin.

Sheila tossed her white blouse onto the defense table and reached for the button and zipper on her dark blue skirt. It soon dropped to the carpeted floor revealing her panty hose that covered her lacy white panties. After tossing her skirt to the table she kicked off her dark high heels, hooked her fingers into her hose, peeled them down and tossed them on top of her skirt.

Sheila stood in the courtroom in her white satin bra and panties looking around at the leering eyes of the crowd. She was tempted to make a run for it rather than continue but there was nowhere to run for there were people standing in the aisles and the smiling courtroom guards blocked the doors.

"Judge isn't this enough?"

"No it isn't! And stop wasting the courts time. Get on with it! Or should I say, get off with it."

This brought a laugh from the courtroom and the judge pounded his gavel to restore order. Sheila took a deep breath and unhooked her bra. She tossed it to the pile with one hand as she used her other arm to cover her breasts. She then took her free hand and awkwardly peeled down her panties and tossed them to the pile. Sheila quickly put her free hand over her naked shaven pussy. Tracie stood up and addressed Jason who was enjoying the strip show as much as everyone else.

"Is this the way she stood when you first saw her naked?"

"Not exactly... She was still wearing her shoes and her hands were at her sides."

"The defendant will put on her shoes and stand with her hands at her sides."

Sheila looked at Don.

"Why don't you object to this?"

"I can't. You better do what they ask."

Sheila's face was red as much with anger as embarrassment. She worked her feet into the high heels that lay next to her then looked at the jury as she forced herself to drop her hands.

There were ten men and two women on the jury staring at her naked, exposed body. The women looked like lesbians to Sheila for they seemed to be getting as much joy as the men at her exposure. A few of the elderly men were enjoying themselves in particular as one of them asked the judge if it would be alright if she turned around. The judge ordered Sheila to turn around. Sheila reluctantly agreed. After she stood there for a moment the judge told Sheila to walk around the area in front of the jury in a small circle so that they all would get a good look at her entire body.

After an extended amount of time, Tracie asked the jury if they had seen any tattoos or beauty marks on Sheila's body. They all shook their heads. Then the judge said that they had seen enough. The courtroom laughed again before the judge told Sheila she could sit down. Sheila quickly covered her nudity as much as she could with her hands and returned to the table to get her clothes. But they were gone. She looked at Don and asked him where her clothes were. He told her he didn't know. Then the judge spoke up.

"The defendant will take her seat!"

"But judge...I can't find my clothes."

"The court cannot take the time to search for them presently. We must get on with the proceedings. We'll find you something to wear. Now take your seat!"

As Sheila walked around the table to her seat she noticed several of her students in the front row, right behind her seat.

"What are you kids doing here?"

"We're on our government field trip today." This came from a smiling nerdish teen whose smile was never bigger. Sheila sat down on the cold chair and once again Don moved closer and quickly put his hand back on her leg. Tracie returned to her questioning of Jason, asking him about all the sex he had with Sheila. He described over and over the acts which kept the courtroom focused and excited.

After about twenty minutes of this Tracie asked Jason to describe the blow job that Sheila gave him.

"I'm not very good at describing things. Could I act it out?"

"I think that's a great idea, if the court will allow."

The judge agreed and told Sheila to come forward. She jumped to her feet her hands still trying to cover herself.

"This is ridiculous!"

"One more outburst from you Mrs. Moser and I'll find you in contempt! Now get up here!"

Sheila walked back to the spot where she stripped as Jason got off the stand. He walked over to Sheila and stood beside her. Tracie approached them.

"Now, what position was Mrs. Moser in?"

"She was on her knees."

"Mrs. Moser, Please get on your knees."

Sheila wanted to reach out and slap Tracie. She could see how much she was enjoying humiliating her. But having no choice she sunk to her knees. Jason continued.

"She was sitting back on her heels with one hand rubbing her pussy and the other rubbing one of her tits."

"You mean her breasts. Mrs. Moser, do as he described, please."

Sheila began rubbing her nipples and pussy, her face just inches from Jason's crotch.

"Is that how you remember it, Jason?"

"Almost. Her mouth was open wide in the shape of an 'O'.

"Sheila...I mean, Mrs. Moser, do as he said."

Sheila looked up at the bitch sending daggers at her through her eyes. Then she tilted her head back and opened her mouth wide, shaping her lips as if his cock were passing through it. The court was dead silent as they imagined what had happened between Sheila and the teen. Sheila knelt there in the awkward position for several minutes as Tracie described in very erotic terms just what had happened.

Sheila listened to the words Tracie spoke as she rubbed her pussy and nipples and she couldn't help but get excited thinking back to the actual event as it was being described. Suddenly drool began to spill from her mouth as if it were the cum that had filled her mouth during the genuine act. When Tracie spotted it she chuckled and suggested it was a Pavlovian moment. The jury leaned forward imaging a cock thrusting in and out of Sheila's mouth. Tracie finally addressed the judge.

"That's about it unless the court would like to see..."

"I think we've seen enough. The defendant can return to her seat."

Sheila stood up and returned to her seat, glancing at the crowd which seemed larger and populated with even more of the people she knew, neighbors and old classmates. The judge suggested that unless there was an objection they would adjourn for the day. Sheila Jumped up.

"Your honor, what about my clothes? I haven't any clothes to wear home."

The judge turned to the bailiff who brought Sheila a small towel. Sheila stretched the towel around her. It barely reached and it only went down to the bottom of her ass. Don led her through the crowd, making their way to the door. Hands reached out and groped her, some trying to pull the towel free. When they got outside Sheila saw a huge crowd staring at her, cheering, whistling and making cat calls. Many of the women called her a pervert and slut. Just as they started down the stairs a hand reached out and grabbed at the towel trying to pull it free. Sheila grasped it in terror holding on for life and calling for help as the crowd just cheered.

Sheila screamed and suddenly woke up in her bed covered in sweat soaked sheets. She thought to herself, 'A nightmare'. She reached over for the scotch bottle sitting on the nightstand. It was almost empty. She would need to restock her bar.

That evening Sheila asked her daughter Sierra if she needed anything for she was going out for some things. Sierra answered no. So Sheila drove directly to the liquor store that sat at the end of a strip mall next to the park.

Sheila had just put a grocery bag full of liquor into the trunk of her car. It was in the darkened, near vacant parking lot that Sheila heard her name called out. She turned to see Jason walking to her from the shadows. Sheila wanted dearly to run but she just smiled instead. She was still hoping to get some kind of friendly control over him.

"I thought that was your car. How are you doing Mrs. Moser?"

"Hello Jason. I was just on my way home."

"Could you do me a favor?"

"That all depends on what it is. You see, I'm in a bit of a hurry. Sierra's at home waiting for me."

"This won't take long, Mrs. Moser. I need a bottle of Jack Daniels."

"Now Jason, You know I could get in trouble for giving you liquor."

"You could get in trouble for giving me a blow job too."

Sheila forced a laugh and smile.

"Very funny, Jason. I just can't take the chance."

"Okay then. I'll go talk to Mr. Morgan."

Sheila's smile instantly disappeared when he mentioned the principal.

"Why are you going to him? He's not going to buy it for you?"

"He might. He once told me I could talk to him about anything. You know, sports, school work, girls..."

Sheila wasn't sure if he was making a threat but she couldn't take the chance that he might inadvertently say something about her. She looked around.

"Okay, I'll get you a bottle of Jack Daniels, but you can't tell anyone about this. And go behind the store. I'll drive around when I get it."

Jason took off in the dark toward the rear of the store. Sheila's plan was to pull around to the back, hand the bottle out the window and take off before anyone could see her. As she came out of the store with the bottle of Jack she looked around once more to see if anyone was near. With no one in sight she jumped into her car and quickly drove behind the store. It was dark with only a single light on a pole above her. But she didn't see Jason.

Suddenly he came out of the wooded area and jumped into the passenger side of the car and slammed the door.

"I had to take a piss."

"Here's your bottle. Now get out because I got to go."

Jason ignored her statement and opened the bottle and took a deep swig. He took a breath and then took another swig.

"Here Mrs. Moser, have a drink with me."

He held out the bottle but Sheila quickly turned her head and began looking around to see if anyone saw him get into the car.

"Jason-"

"Don't worry Mrs. Moser, hardly anyone comes back here. I know cause I've been hanging around back here for the last two years. I fucked Melissa Martin right over there one night last summer for a half an hour and no one saw us."

Sheila was surprised how easily he mentioned his session with one of the elite girls from the school, who was also a friend of her daughter. She wondered if he made any references to her around his friends. It made her so nervous that she grabbed the bottle from his hands and took a long swallow of the whiskey.

Jason then took the bottle back and had another drink before handing it back to her. She took another swallow and began to relax a bit.

"Jason, you better go."

"I will in a minute. You know Mrs. Moser, watching the end of that bottled touch your mouth has got me a little excited. The way your lips wrap around it-"

"No Jason..."

"It won't take long. Just suck on it for a bit."

Sheila looked at his lap and suddenly realized his cock was out and rock hard. He hadn't even zipped up after relieving himself in the woods. Sheila hesitated, took the bottle from his hands, looked around the area, took another swallow of the whiskey then went down on Jason's cock.

"Owww!"

Jason yelled as Sheila pulled away from his cock and innocently asked, "Did that burn?"

Sheila acted innocent enough that Jason didn't catch on that she did it on purpose. He sat there rubbing his cock as it began to deflate from the burning pain.

"You still want me to...continue?"

"Yeah. Just don't drink anymore till you're done."

As Sheila started to lean over again, Jason grabbed her head and pulled her into a deep kiss. The combination of the whiskey, the danger and the kiss began to arouse Sheila. But just as the kissing began to really get her going, Jason pulled her head away and guided her mouth to his cock which was now hardening once more. Jason grinned.

"That's better."

Sheila lifted her head slightly.

"Keep looking around and make sure no one is there."

"Sure thing, Mrs. Moser."

Jason pushed her head back down on his cock as he occasionally glanced out the windows. He played with her hair-sprayed hair as she sucked him, making her stylish hair-do into a ratted mess. Jason was enjoying himself. With his right hand on her bobbing head Jason began to unbutton the back of Sheila's baby blue blouse but before he could get half way done Sheila took her mouth off his cock.

"Don't Jason. We haven't got enough time. Just let me finish you."

Jason was slightly disturbed that Sheila stopped him but he quit, leaving her blouse half undone and took another gulp of whiskey. He showed his feelings by increasing the speed of the blowjob by working Sheila's head on his cock even faster. Jason was in no hurry but there was a chance that someone might come out the back door of the liquor store and interrupt his fun so he work his way toward an orgasm.

As much as Sheila was enjoying the feel of Jason's gorgeous cock in her mouth she hated the idea of blowing someone in a car which is something she hadn't done in years. She also hated having him mess with her hair and pound her head up and down on his cock. The whiskey helped her deal with the humiliating action but she just worked at getting him off as quick as possible. Her wet lips and swirling tongue finally did the job and she heard Jason begin to moan.

Jason held Sheila by the hair and pushed her head down on his cock as the first spurt shot out. Sheila was still not used to swallowing large amounts of sperm and she fought Jason and pulled her mouth off his erupting cock. The second spurt hit her eye and the final two spurts hit her chin and dripped down onto her blue blouse.

Sheila coughed and rubbed her burning eye as Jason jerked his cock empty. Finally with Jason chuckling Sheila spoke up.

"Jason! Why did you do that? You know I don't like it when you force my head down when you cum."

"I'm sorry, Mrs. Moser. I guess I just got over excited."

"Yeah? Well..." She quickly composed herself. "Just don't let it happen again. Okay? Now take your whiskey and go."

"Can you give me a ride home?"

"Jason, now what would your parents say if I pulled up-"

"They're not home. This is their country club night and they're always out till after midnight. And you can drop me off behind the house. There's a road back there without any houses on it."

Sheila had learned by now that it was pointless to argue with him. So she agreed. As they pulled out into the street Jason told Sheila about the large cum stain on the front of her blouse. Sheila looked down at it and cursed while almost driving off the road. If Sierra saw her walk through the door with a stain on her blouse and her hair messed it would be obvious what had happened. Sheila kept looking at the stain and then into the mirror to get an idea of her messy hair when suddenly she heard a siren.

"I think you were speeding, Mrs. Moser."

Sheila bit her lip rather than swear at Jason's teasing remark. She pulled over, grabbed her purse and rolled down the window. What could be worse she thought. The police officer approached her door.

"Aren't you Mrs. Moser?"

Sheila looked up and immediately recognized Rick Hart, a student she had often punished at school about ten years ago. She wondered how a goof like him ever got to be a cop. She quickly put on the charm hoping he was holding no grudge from the many detentions she had given him.

"Why Rick...isn't it?"

"It's officer Hart now."

"Yes... of course."

"License, registration and proof of insurance please."

Rick went through his official routine and then recognized Jason.

"Aren't you the football player?"

henryo
henryo
162 Followers
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