Simpson Sleepover

BY : JamesRyder
Category: +S through Z > Simpsons
Dragon prints: 4670
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.

“Okay boys you have fun tonight” Marge's voice faded out as she climbed down from the tree house. She left her son Bart and his best friend Milhouse alone with the plate of brownies she had just made. Bart and Milhouse had a lot of sleepovers and when the weather was right, they chose to have them in the tree house instead of Bart’s room.

“Oh boy, your mom makes the best brownies.” Milhouse said excitedly grabbing for one.

“Yeah, might explain how Homer got so fat.” Bart chimed in grabbing one for himself.

Bart sat back and began to eat his brownie. He glanced around the treehouse, the two sleeping bags side by side, the wooden crate they used as a table and as a place to hide comic books, a bean bag chair and the cooler he had borrowed to keep cold sodas in. Milhouse was sitting on the floor near the window that faced the house, and his crush, Bart’s sister, Lisa’s bedroom window. Knowing the boys were having a sleepover and that they often liked to prank her she had drawn the blinds shut tight.

“Come on man, unless you have x-ray vision you aren’t going to see through those curtains.” Bart lightly teased his friend.

“I know.” Milhouse responded sadly, “but I can still hope.”

Bart had something interesting planed for tonight. He had got his hands on some special magazines and had hid them in the crate under all the comics. He was excited to witness Milhouse’s reaction. Recently Bart had found himself as attracted to the guys in his class as much as the girls. He wanted to see how far he could get.

It was still evening and not nearly dark enough for him to want to try anything yet, so he got out the comics he had bought for tonight. He and Milhouse got down to reading and pigging out on brownies.

As it got darker Bart set up the battery-operated lantern. They used to use candles until the day they had almost burned the tree house down. The brownies were gone, and they were about a third of the way through their supply of soda, so they were both riding a pretty good sugar high.

“Hey Milhouse, I’ve got some special magazines for tonight.” Bart ventured.

“You got another expensive comic?” Milhouse asked with excitement.

“Better.” Bart said as he lifted the lid of the crate.

“Mad Magazine?” Milhouse was sitting up on his knees in anticipation.
“Better.” Bart repeated as he dug to the bottom of the crate and grabbed the nights delight.

“A Victoria Secret catalog.” Milhouse asked sheepishly but with genuine hope in his soft voice.

“Better.” Bart said in a low tone as he pulled out the porno mags and fanned them out so Milhouse could see most of the covers.

“Oh my god Bart, how did you get those?” Milhouse had lowered his voice realizing the trouble they could get into for having these. His mom had found his dad’s stash a few weeks ago and he was still sleeping on the couch.
Bart thought back to being on his knees while Nelson, Jimbo, Kearney, and Dolph took turns making him suck their cocks for the porno’s they had stolen but decided that might spoil his chances for fun latter. Instead he decided to lie.
“Found them in the woods… in a tree.” Bart mumble fast. “It was a good thing I found them before it rained.” He finished triumphantly.

Milhouse however was no longer paying attention. He was trying to move closer to the crate while also adjusting himself in his pajama pants to try to hide his growing erection. Bart having less shame was not only taking no steps to hide his growing boner but was openly checking out his friends growing bulge.

Laying out a few of the mags for them to paw through Bart looked up from Milhouse’s fully tented pajama pants to see his friends’ eyes glued to his ever-hardening cock straining at his pajama bottoms. Bart didn’t know it but Milhouse had been having wet dreams involving his best friend for almost a month.

Bart sat down next to Milhouse and grabbed the magazine that had his go to picture in it. The girl in the picture looked a little like an older version of a girl he had felt up from his class. She was on her knees, legs spread fingering herself, while a guy was busy fucking her mouth and pinching one of her nipples.

Bart watched as Milhouse moved his hand into his pocket and started touching himself. Bart decided to try and take this to the next level.

“Hey man we both want to jerk off to this so why try doing it in secret.” Bart said as he decided to take the initiative and pulled down his pajamas and underwear to release his rock-hard cock. He was pleased with his own cock. Circumcised and coming in at 6 inches long but over an inch thick.

Milhouse was shocked at first and tried to look anywhere but at Bart’s dick. Then he started stealing a glance here and there feeling more and more comfortable with the situation. Bart was giving himself long slow strokes and Milhouse found himself staring at the show.

“Well Milhouse it’s your turn to show off.” Bart was getting worried Milhouse would be to nervous.

Milhouse hesitated for another second before finally joining Bart in pulling down his bottoms and exposing himself. Now it was Bart’s turn to stare. Milhouse had a much bigger cock than he would have thought. It was 8 inches long and at least as thick as Bart’s. He was impressed. None of the bullies he had sucked off even came close to his size let alone as big as Milhouse.

By now they had flipped a few more pages in and were busy jerking off next to each other almost paying more attention to what the other was doing than looking at the porno mags. On the next page there was a picture of two girls fingering each other.

“Hey Bart…” Milhouse said sheepishly, “…want to try that with each other?”

Bart needed no further encouragement and reached out, wrapping his hand around Milhouse’s warm hard cock and started stroking it gently. He groaned a little as Milhouse returned the favor. Bart bit his lip and looked down at the amazing site in front of him. His friends’ cock in his hand and his cock being massaged firmly by Milhouse.

“Want to get more comfortable?” Bart asked motioning towards the sleeping bags on the floor.

Milhouse was reluctant to let go of his new toy but he did and crawled over to his sleeping bag. When he got there Bart saw him finish pulling off his pajama bottoms and underwear, so he was naked from the waist down. He also reached up and slid off his glasses before laying back and beginning to stroke himself again giving Bart a full view of his masturbation.

After taking in the scene for a few heartbeats Bart made his way to his own sleeping bag and not wanting to be outdone by Milhouse he pulled off his bottoms and top, so he lay completely naked and started stroking himself again too.

Milhouse was not going to be outdone either and tried to pull his t-shirt off but got stuck a little and started struggling. While Milhouse was using both hands trying to get unstuck so Bart reached out and began stroking his friends cock again. Milhouse was still struggling with the shirt.

“Bart, I’m seriously stuck.” Milhouse moaned with his face pressed up against the fabric so Bart could clearly see the outline. “And I’m missing the show.” He returned to his efforts.
Bart made a split-second decision. “Okay man, don’t have a cow, does this help?” Bart voice carried an air of mischief.

Milhouse relaxed his struggles expecting his friend would soon have him free. Bart instead moved his hand down to the base of Milhouse’s cock, cupping his nut sack and bent over. He guided the head of Milhouse’s cock into his waiting mouth, just managing to fit the width without his teeth scraping it. Milhouse was so shocked he flopped down onto the sleeping bag and his motion practically impaled his dick down the back of Bart’s throat. Bart gagged in surprise and backed his head off a bit, but he didn’t stop giving Milhouse a blow job.

Milhouse falling back and arching his back was just the trick he needed to get unstuck from his top. Finally, free and able to see me stared in rapture as Bart continued to bob his head up and down on his cock taking it deep in his throat at his own pace this time. He leaned over and reached out to stroke Bart’s cock while he continued sucking like an expert.

Bart moaned around the cock in his mouth when Milhouse started jacking him off again. He had decided to try for everything he could think of. He kept using his hand to cup Milhouse’s nuts and massage his sack while throating his cock deeper and deeper. He was drooling a lot and his hand was catching most of it. He realized that his fingers had become slick and decided to take this up another level.


Milhouse froze as Bart took his dick deep in his throat at the same time as he slid a slippery finger straight up his asshole. He had never felt anything like this, and he was loving the feeling. He wanted Bart to keep going so he tried showing his enjoyment by speeding up his motions on Bart’s rock-hard member.

Bart kept fingering his friend’s anus going deeper and deeper with his finger as he kept the cock deep in his throat longer and longer without gaging. He wanted in on some of the fun too and a picture from one of the magazines gave him the inspiration. He stuck a second finger in Milhouse’s ass and got a little rougher to make sure he had his attention and pulled his mouth off the cock entirely while gently jerking it with his other hand.

“Let’s try another position I’ve seen Milhouse.” Bart cooed as he looked up at Milhouse whom seemed to lose focus every time Bart’s two fingers hit the knuckle. “I want in on the fun too.”

“Sure Bart… I want… to try… anything.” Milhouse gasped back as he got fingered deeper and deeper.

“Lay on your side then.” Bart gave the direction like a command and Milhouse was quick to obey. Bart shifted around so he too was on his side in a classic 69 position. “Now just do what I do.”

Bart returned his mouth to Milhouse’s waiting cock and as he began to feed it back into his mouth, he could feel Milhouse pulling his cock toward his own mouth. The second Bart’s cock slid into Milhouse’s mouth he was in heaven. Then he felt Milhouse spread his butt cheeks and remembered Milhouse hadn’t drooled on his hand while sucking dick yet.

“Wait man, you can’t go in dry.” Bart was almost choking the words out as he ripped Milhouse’s dick from his mouth. “You got to get some spit on it like I did, or it won’t work.”

Milhouse reached his hand around to his mouth and wiped a generous amount of spit onto his fingers. He really didn’t want to screw this up again, so he decided to make sure he was doing it right. He lifted his head up and spread Bart’s ass cheeks, immediately spotting his puckered anus. He watched as he guided his now slick finger into his friends’ tight butt hole before moving his head back down and going back to sucking Bart’s cock for all he was worth.

At first Milhouse couldn’t take nearly as much cock down his throat as Bart seemed to be able to but after a few minutes he was giving it his all while sliding two fingers deep into Bart’s butt and thrusting his hips a little to help Bart really work his own pole.

Bart’s moans got louder and louder and the vibration finally pushed Milhouse over the edge. He felt his balls begin to tighten and tried to pull his head back to warn Bart, but Bart was thrusting his hips too and all that came out was a mumble. Although he was caught off guard Bart swallowed Milhouse’s cum like an expert. They both backed off panting heavily with a tiny amount of semen dripping down Bart’s chin.

“Wow Bart, that was incredible.” Milhouse could barely catch his breath.

“Hey man, what makes you think this is over?” Bart asked motioning down towards his still had dick. “I haven’t gotten my rocks off yet.”

“Alright, fair is fair just let me catch my breath and I’ll finish sucking you off.” Milhouse panted flopping on his back.

“What makes you think I want your mouth?” Bart’s voice had a harder edge Milhouse recognized from anytime they were going to do something no matter what arguments were made.

Bart crawled over to the wooden crate and cleared it off. He motioned for Milhouse to lean over it. Milhouse decided not to argue, not just because he didn’t want to upset Bart, but deep down because he wanted to try this. Milhouse leaned down so his chest rested on the crate and his already loosened ass hole was facing Bart.

“Hey, want to make a bet?” Bart asked playfully, his earlier edge gone with Milhouse’s submission.

“What’s the bet Bart?” Milhouse remember too many times agreeing to bets he didn’t fully comprehend yet.

Bart was spitting on the head of his cock and massaging it slowly as he got on his knees behind his friend. He was the perfect height for this to work without either of them having to stretch.

“While I use your ass to finish, I’ll also jerk you off.” Bart began to explain, placing the head of his cock to Milhouse’s anus and reaching around to fondle Milhouse to emphasize the arrangement.

“If I cum before you then next week we’ll do whatever you want during our sleepover, but if you cum first then I’m in charge next week.” Bart pushed himself deeper and deeper into Milhouse marveling at how tight his asshole really was. At the same time, he really started to pick up speed jerking on Milhouse’s cock that was once again rock hard from the double stimulation.

“Deal.” Was about all Milhouse could grunt out as Bart bottomed out in him. He knew that if he won the first thing that was happening next week was him fucking Bart’s asshole.

Bart was buried in his friend’s ass and began to pump in and out. Nice and slow so he wouldn’t cum to fast and loose the bet he was also vigorously jerking off Milhouse. It was hard to concentrate on keeping the unfair rhythm as Bart was in heaven. He had never thought anything could feel as good as this. He briefly wondered how Milhouse felt.

Milhouse could feel every inch of Bart as he pushed himself in and out and to his surprise, he loved every second of it. This feeling of being fucked was new but he could already tell this was going to be his new favorite activity. Maybe he would steal his mom’s dildo when he was left home alone and fuck himself with it. He slowly realized how Bart wasn’t playing fair in the speeds and decided to try to even the odds.

Bart almost exploded as he was slowly pushing himself back in after pulling out everything but the tip of his dick and Milhouse pushed his hips back impaling his ass on Bart’s dick. Bart was worried about how this sudden switch of fate would turn out for him when he discovered Milhouse had played himself. Taking Bart’s dick that hard and fast had been all Milhouse could take and he came for the second time that night all over Bart’s hand and the side of the crate.

“I win.” Hissed Bart bending down, so he was right next to Milhouse’s ear. After a brief second to gloat he decided to wrap this up.

Bart put both his hands on Milhouse’s hips and began to fuck him hard and relentlessly. Pushing harder and faster, riding his friend’s tight ass as much as he pleased. Bart had won the bet and that feeling of control and supremacy was a major turn on for him. He sat back on his own legs pulling Milhouse back with him and used his grip on his hips to keep fucking him harder and harder. He was so close but just couldn’t get over the edge. He looked up at Milhouse’s face to see him panting hard.

“Please.” The word was the quietest whisper from Milhouse’s lips but that was the key.

Bart pulled Milhouse down hard and emptied his balls as deep in his friend as he could. He held them both there for a minute while he gushed out then they slowly sunk to the floor. Both boys were spent and exhausted. As Bart’s cock softened it eventually slid out of Milhouse’s abused hole.

“Wow Bart, that felt amazing.” Milhouse looked Bart in the face then kissed his friend tenderly.

Bart was surprised at first, but he returned the passionate kiss. It felt right to him and he decided that this would not be the last fun they would have tonight. They broke the kiss and moved back towards their sleeping bags. Bart grabbed the stack of porn magazines so they could keep looking through them and maybe try some other things.

Maybe if Bart had been focused on his surroundings instead of focusing on continuing his and Milhouse’s ecstasy filled night he would have noticed the movement in Lisa’s curtains as she quickly shut them after having watched her brother fuck his best friend. She pulled her hand out of her drenched panties and decided she would find a way to get in on the action.



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