A Sick Savage Springfield

BY : JamesRyder
Category: +S through Z > Simpsons
Dragon prints: 2745
Disclaimer: I do not own The Simpsons or any of their characters. I am in no way affiliated with the copyright owners. This is a work of Fan Fiction and written solely for fun. There is no profit from this work.

Skinner’s Revenge
M/m, Oral, Anal, Punishment, Rape

Principal Skinner stood at his office window and watched the kids play outside. It was a cool fall day, and all the kids were running around. Well almost all of them. Bart Simpson his 10-year-old nemesis and perpetual troublemaker was sitting on the bench with his best friend and often used scapegoat Milhouse.

They were watching the other kids in the same way he was watching them. Waiting for something. Looking for something. He knew they were up to no good and he was determined to bust them this time.

Today he would have his revenge, after years of pranks, Bart still never got anything more than a slap on the wrist. It had emboldened him to do whatever he wanted whenever and get away with it. Bart had slashed his tires last week and the schoolboard had told Skinner that since he had no video proof, he couldn’t even give Bart a detention.

Well, the next time will be different, Skinner thought. That very same day he had bought a camcorder. It sat in his desk ready to go. If they wanted proof, he would give them proof. He would take that spiky haired menace down.

The phone on his desk rang and he rushed over to it. It was Superintendent Chalmers reminding him to tell his staff about next week’s mandatory meeting.

“Yes sir, I’ll make sure they all know.”

He hung up the phone and rushed back to the window. Crap, he noticed the two hooligans weren’t on the bench anymore. He quickly scanned the playground but didn’t see them anywhere.

“Where could they have gone,” he wondered out loud? He craned his head around and caught sight of Milhouse looking back around the corner of the school before ducking back and going to join Bart he assumed.

The part of the school they had gone to was a blind spot, no windows overlooked it, and it couldn’t be seen from the playground. They had to be up to something otherwise there was no reason to sneak to that area.

Skinner smiled to himself and quickly got the camcorder out of his desk. He rushed through the halls. He knew a barely used exit door that would let him see the area immediately but wouldn’t alert the little troublemakers that he was there.

He paused at the door and began recording. He walked through the door pointing his camera ready to rush over and bust them but instead he froze. He couldn’t believe what he was seeing. Bart was on his knees, his back up against the wall, and Milhouse was standing in front of him with his pants around his ankles. His naked ass was in plain sight and based on his motions it looked like he was face fucking his best friend.

Skinner knew he should rush over and break this up. He should haul them into his office call their parents and the school board. Instead, he ducked down a bit behind some bushes and continued to film.

The worst part of it was that he was getting hard watching them go at it. He was enjoying this. There was something about the bane of his existence getting face fucked that made him not want to look away. The longer it went on the more he knew he wouldn’t be the one to stop it and he might not even say anything at all.

As he watched Milhouse stepped back, and he briefly wondered if he had been discovered. He hoped not. It wasn’t that he was concerned about them seeing him as much as he was concerned that they would stop.

He was both relieved and shocked as he saw that instead of getting up Bart had gotten on all fours and pulled his shorts down to reveal his small yellow ass to his friend. The position he had chosen also gave Skinner a nearly perfect side view as Milhouse knelt down behind his friend, spread his ass cheeks, and pushed his dick in.

Either Milhouse wasn’t very big, or they had done this often enough to loosen Bart’s asshole because Milhouse wasted no time in grabbing Bart’s hips and fucking him hard and fast. He watched and kept recording.

The longer he watched the less he thought it was weird how much he was enjoying it and weirder that Bart would be the one getting fucked. Bart always seemed to be the dominate one in their friendship.

Maybe this is how he gets Milhouse to take the fall for him, Skinner thought bitterly.

He was uncomfortably hard and reached down with one hand to try and adjust himself. He wanted to jerk off but knew that would be impossible to explain. Besides he had the recording and could watch it latter and jerk off then.

Skinner briefly considered how much longer the kids had for recess. They had to be close to going back inside at this point. He wondered if they would stop or risk being late.

In the end it didn’t matter though. Soon Milhouse stiffened and quickly pulled out sprayed his spurts of cum all over Bart’s ass cheeks. Milhouse pulled up his shorts and pulled out some napkins from the cafeteria.

This wasn’t a spur of the moment thing, Skinner thought as he watched Milhouse wipe his seed off of Bart with the napkins.

As soon as he was cleaned off Bart pulled up his own shorts and the boys hurried off back to recess. Skinner stopped recording and got up. He used his key to get back in and headed straight for his office.

He needed to review the footage.


Skinner was hurrying out of his office and headed for the bushes again. He had watched and filmed the two boys participate in the same basic scene for the past three days. He didn’t even pretend like he was gathering evidence anymore. He had given up that flimsy excuse the first time he had jerked off in his office watching what he had recorded.

He would watch and wait for them to sneak off then hurry to his hiding spot. Just like he was doing now. The camera would start filming right as he snuck out and he would add another episode to his growing collection.

As he snuck out of the door and looked over, he noticed the two boys were just standing there having what looked like a heated argument.

Crap, he thought, I hope this doesn’t mean I won’t get my show.

As he watched the argument began to escalate and became physical. Bart grabbed Milhouse and pushed him hard face forward against the wall. Bart reached down and pulled down Milhouse’s shorts and underwear quickly. The little blue haired boy continued to struggle but was physically outmatched.

“No,” Milhouse shouted as Bart pushed him even harder against the wall.

Skinner wished his next action was heroic or well-meaning, but he knew as he stood up from his hiding place and started towards them that his intentions were purely selfish and wrong. He just didn’t care. He saw a perfect opening and went for it.

“No,” Milhouse repeated perfectly timed with Skinner running forward, “please Bart don’t rape me.”

“Hey,” Skinner shouted as he grabbed Bart by the shoulder. “What’s going on here?”

Both boys turned quickly. Milhouse had a look of relief plastered all over his face. He knew what Principal Skinner had saved him from and how much he owed him. Bart looked almost smug until he saw the camcorder and realized what his nemesis had gotten on film. His expression turned to one of fear and Skinner prayed neither boy would notice his raging hardon in his pants.

“Uh…” Bart stared open mouthed trying to find a lie that would work.

“Shut up,” Skinner snapped in his best drill sergeant voice. He wanted Bart to know this wasn’t some easy way-out offense. He also didn’t need a lot of eyes on him for what he was planning or for anyone else to notice the commotion.

“Milhouse,” Skinner said looking right at the boy, he still hadn’t pulled up his shorts. “Maybe you should pull up your shorts and rejoin your classmates at recess. I’m going to have a long and extensive discussion with Bart about his behavior.”

Milhouse pulled up his shorts as he ran off. He was all too happy to be out of an embarrassing situation and Skinner’s assurance of him dealing with the issue meant he wouldn’t bother to mention it to anyone else. As his only possible scapegoat ran off Bart watched him go and then hung his head.

I have him, Skinner thought as his dick got hard. I’ve won.

Bart said nothing as Skinner lead him back through the door and too his office. He closed the blinds so no one could see into his office from outside and so Bart couldn’t see Milhouse. Skinner didn’t need Milhouse having a change of heart. After he closed the blinds, he also walked over and locked the door.

“So, you were going to rape Milhouse?” Skinner just let fly with that but didn’t wait for a response. “Your best friend, your closest ally, and you were going to rape him? Sit down Bart.” As he finished, he sat in his chair and pointed to one of the chairs in front of his desk. He ran his hand over the phone almost daring Bart to defy him and see who he called first. The police, his parents, who would be worse.

“Listen man,” Bart was almost pleading, “he’s been rapping me, and I was just trying to get some payback.” He lied with the confidence that he had a fool proof way out. “I know it’s not right, but you can’t blame me.”

“Is that so,” Skinner asked? His face took on a truly heartless look as he pulled one of the other tapes he had in his desk. He popped it into the camcorder and hit play. On the screen was Bart taking it in the ass and begging for it to be harder. “Doesn’t look like rape to me.”

“What the hell man?” Bart was in shock. He had thought this was the first time Skinner had caught them. “How many times have you watched us?”

“Enough to know you’re not lying your way out of this one.” Skinner sat back in his chair and folded his arms. He was savoring this feeling.

“So, what are you going to do?” Bart was caught red handed and had to resort to making some sort of deal.

“Well,” Skinner began with a vicious smile, “that depends entirely on you. Either I could take all of this to the school board and your parents. That will result in your expulsion at the very least. Not to mention how your parents will react.” He paused to let that sink in and salivated at the terrified look in Bart’s face. “Or you and I can work out a proper punishment.”

“What’s the punishment?” Bart was defeated and at Skinners mercy.

Skinner stood up and pulled his hard cock out of his pants. It was six inches long and easily an inch thick. Bart’s look of defeat turned into one of terror and that only made Skinner harder. He stared at Bart and Bart looked away.

“Since you like to fuck and suck that seems like the perfect punishment.” Skinner’s voice took on a commanding tone. “Now get over here and get to it.”

“What’s to stop me from telling my parents about you wanting to rape me?” Bart had a little confidence back in his voice thinking he found a loophole. “I bet this could cost you your job or even get you arrested.”

“I thought of that already,” Skinner told him relishing the look of his hopes fading. “If anything happens to me copies of you letting Milhouse fuck you will be delivered to Nelson, Dolph, Kearney, and Jimbo. I wonder what they would do to you?”

He briefly considered bringing up that it wouldn’t just be Bart who would fall victim to the gang of bullies but Milhouse as well. He decided against it knowing Bart was unlikely to care but likely to use that as a way out. Bart started to sob and hung his head.

“Really? You’re going to cry?” Skinner raged and moved to stand right next to Bart with his raging hard on almost eye level with the crying boy. “You finally have to face some consequences to your actions, and this is your response?”

He grabbed Bart’s spikey hair in one hand and lifted his head. With his free hand he slapped Bart in the cheeks with his cock.

“Pathetic,” Skinner sneered, “now open up.”

Bart opened his mouth a little but not enough for skinner to get the head of his cock in. All he could manage was the tip and Bart seemed reluctant to open any wider. Skinner gripped Bart’s hair harder and really yanked. Bart opened his mouth in shock and pain.

Skinner didn’t wait. He shoved his cock as deep into Bart’s mouth and throat as he could before he feared he might kill him. Skinner didn’t care about hurting and using the boy, but he wouldn’t be able to explain it away if he died. Bart didn’t fight back but also kept crying even with the cock buried deep in his throat.

“Now show me all the skill you’ve shown Milhouse,” Skinner hissed. He put his hands on either side of Bart’s head and started moving his Bart’s head in time with Skinner pushing his hips forward. “That’s better. I guess it’s good you learned something in school.”

Skinner continued to work Bart’s mouth and looked down to lock eyes with him. He expected to see sorrow or hatred, but Bart’s stare was blank and hollow. He had broken the boy’s spirit. There was no more mischief or spite in him.

Maybe this was the discipline that will turn him around, Skinner thought although he really didn’t care if it saved the boy or not. This wasn’t about him. This was about Skinner repaying the boy for years of misery and frustration.

He pulled Bart’s head away and pushed him back into his seat. His cock was glistening with Bart’s spit. Skinner felt annoyed that Bart wasn’t crying or begging. It was like the boy had just switched himself off.

Well, I’ll snap him back to reality, Skinner thought with a wicked grin. He grabbed Bart and lifted the boy easily.

Bart was basically dead weight as Skinner bent him over the desk. He still didn’t respond as Skinner pulled off his shorts and underwear. He put his forearm down on Bart’s back to hold him in place. Not because Bart was fighting back but because his feet didn’t touch the ground and Skinner didn’t want him falling off.

He got right up behind Bart and spit on his bare asshole. Skinner pressed the head of his cock to the puckered little hole and shoved. He was not gentle or slow and that finally got him the reaction he had wanted.

Bart screamed at the rough invasion of his tight hole. He still didn’t struggle but with every thrust he let loose with an ear-piercing scream. Skinner couldn’t be discovered now, and he got another wicked thought.

“Hey Bart,” He hissed at the screaming boy as he reached for what he wanted. “Eat your shorts.” Skinner chuckled at his own joke as he shoved Bart’s wadded up shorts into his open mouth.

He continued to pump away listening to Bart’s muffled screams as he raped his asshole. He didn’t care anymore. He just wanted to finally get off and finish breaking this little bastard mind body and soul.

Skinner felt his orgasm building and he put his all into every thrust. He grunted and buried himself into Bart as he let loose with a torrent of hot cum. As Skinner finished, he kept himself inside determined to go soft before he pulled out.

“That was great. We may have to do this more often.” Skinner wasn’t making an empty threat. He was going to do this as often as he could.

He finally went soft and pulled out with a wet pop. He lifted Bart off his desk and put him on his feet. “Now clean yourself up and I’ll write you a pass to go back to class.”


The next morning Principal Skinner walked into the school walking a little taller with a genuine smile on his face. All of that died as he was met with Super Intendant Chalmers and Police Chief Wiggum. Bart had told his parents and Skinner was arrested. They had the tapes, Bart’s statement, and Milhouse’s backing of that statement.

Skinner had plead guilty and was sentenced to thirty years in Springfield Maximum Security Prison. Now his new life consisted of retelling this story as his cellmate used his asshole for his own pleasure.

“Tell me again all about the broken look on his face,” his cellmate said as he pushed deeper into Skinner.

“I really love that part,” grunted Sideshow Bob.



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