Note: This is filthy smut with plenty of taboo subject matter. You have been warned. For the enlightened individuals who do find yellow cartoon women attractive, please enjoy.
Sexual content tags: Ass worship, anilingus, anal sex, titfuck, incest, minor, bestiality, sleeping, voyeurism, bukkake, male-dom, facesitting, deepthroating, ahegao
Chapter 1: Depravity's Beginnings
Bart Simpson was done. What troubles he had had in the past were compounded by the onset of early puberty. All of a sudden he was no longer just a troublemaker, now he was a troublemaker with an interest in girls. He had been led to believe that women liked bad boys, but that didn't seem to ring true on his part. He had been single for so long that it wasn't even funny. All of his relationships in the past had ended before they even began. In other words, he had never gotten laid. One could argue that for a boy his age, that wasn't such a big deal, but Bart had started to feel like if he didn't lose his virginity soon he would do something drastic.
Eventually masturbating just didn't cut it anymore. All those porn stars on his computer screen with their fake breasts and exaggerated moans didn't work like they used to. Instead, Bart had started to notice the females in his own life more and more. And that wasn't limited just to the girls at school…
It all started one morning as he was drowsily entering the upstairs bathroom. He had been so sleepy that he bumped into Lisa who was there brushing her teeth. Lisa gave a cute yelp as her hand unintentionally squeezed the bottle of toothpaste and she fell on her butt.
"Ouch! Bart, what's your problem?"
"Oops, sorry Lis, I didn't see…" Bart didn't even finish that sentence. His adorable little sister was on the bathroom floor with her panties exposed and her whole face covered in liquid white stuff. Of course, that white stuff was just toothpaste, but Bart with his mind so warped by all the hardcore porn he had been watching could not help thinking dirty thoughts. The toothpaste even got in Lisa's hair and dripped down erotically on her flat chest.
For a moment Bart imagined grabbing his sister by her spiky hair and face-fucking her tiny mouth. Hell, Lisa was young enough for him to even cum inside her without getting her pregnant. How awesome would it be to pound that smooth preteen pussy on a daily basis? He could make her totally addicted to his cock if he just had the chance. The bookworm-types always turned out to be the biggest sluts after all… at least in all the porn he consumed.
The young boy still in his pajamas could feel the blood rushing to his nether regions. This was bad. This was absolutely not the time or place to think about these things! Bart covered his crotch and ran to his room.
"Hey, come back here!" Lisa yelled after him, but Bart ignored her.
"Whew, that was close. I'd dead meat if she thought I was attracted to her."
But Bart's erection wasn't going anywhere. In fact, he was more turned on than ever before in his life.
"Damn it, what's wrong with me? She's my sister. Man, I shouldn't have watched so much porn last night."
Still… when had Lisa become so hot? If she weren't so nerdy she'd probably be really popular with the guys at school. Bart wondered if she would make a similar shocked and slightly disgusted expression if she were covered in actual semen. And would all of that just be an act to keep up appearances? Maybe she secretly enjoyed being dominated like that.
"Nope, gotta stop thinking about that!" Bart slapped his own cheeks. If he didn't get his erection under control it would be difficult to run downstairs and catch the school bus.
After getting dressed Bart had finally managed to calm down. He headed downstairs and into the kitchen where his mom had made breakfast.
"Good morning, sweetie," Marge said in her usual raspy yet motherly voice. "I made some pancakes. Eat yours before your father gets downstairs. You remember what happened when you dawdled last time."
Bart sat down and started eating. Meanwhile Marge bent over the sink and started washing dishes. Maggie was playing with her food on the baby chair and Santa's Little Helper was under the table hoping for scraps of food to fall on the floor.
Soon Lisa came down the stairs. Bart avoided eye contact with her in fear of triggering the mental image from before. His eyes wandered lazily around the room until they decided to settle on something interesting; namely his mother's behind. Wait a minute! Had it always been that big and round?
The tight green skirt really hugged Marge's curves, leaving very little to the imagination. The firm apple-shape was accentuated further every time she leaned forward to grab more dishes from the bottom of the sink. Bart could even make out the outline of her panties through the thin fabric. What the hell was Homer doing sleeping on the hammock all day when he had permanent 24/7 access to this beautiful butt?
The boy's pants were getting tight.
Cheese and crackers! What the hell has happened to me? First the thing with Lisa and now this? I can't fantasize about my own mother.
But his imagination was already running wild. He recalled an incident last year when he had been lying on the sofa, staring at the ceiling while bored out of his mind. There was nothing good on TV and his friends were all busy. Marge had absentmindedly walked into the living room and sat on the sofa, not realizing there was someone on it. Her large rear had been suffocating her son for a good three seconds before she realized she had sat on his face and apologized profusely.
At the time Bart had thought of it as nothing other than an innocent mistake not worth dwelling on. But thinking back on it, he remembered the comforting softness of his mother's firm ass cheeks snugly resting on his face. And he wished he could experience it again.
"Bart, what are you staring at?" Lisa said with a humorless glare, snapping her brother out of his filthy thoughts.
"Oh, just spacing out! Thanks for the pancakes, mom!"
He quickly wolfed down his remaining pancakes and got up in a hurry. Grabbing his back bag from the kitchen counter where Marge had packed his lunch, he gave one last longing look at the blue-haired beauty washing the dishes. Even from the side, her motherly hips had such a seductive shape. If it wasn't for Lisa's judgmental stare, he might have even given his mother's ass a playful squeeze.
"Have a good day, my special little guy," Marge said and leaned over to give Bart a kiss on the cheek. This provided the boy a brief opportunity to see the voluptuous woman's cleavage if only for a couple seconds. The last time he had seen her bare breasts was back when she used to breastfeed Maggie. If only she still did that…
"Thanks mom, gotta go." Bart said, covering his crotch with his bag and running to the hallway. From the corner of his eye he could see Lisa's eyes following him with a doubtful expression.
Damn, I hope she didn't realize what I was thinking.
Perhaps it was just his horny brain, but Bart couldn't help feeling that he had seen a hint of jealousy on Lisa's face. As if she wanted Bart to look at her instead of Marge.
"Hmm, no way. She's too much of a goody-two-shoes to have the same kind of degenerate thoughts as me…"
Bart thought that once he got to school he wouldn't have to worry about getting horny in public anymore. And that seemed to be true for a while. None of the girls in his class made him have any weird fantasies. They were just regular brats in his eyes. Nothing worth getting worked up over. So everything seemed to go smoothly. That is, until fourth period.
The summer heat combined with the broken AC unit made the whole class sweat profusely. This also applied to Mrs. Krabappel, who had unbuttoned three buttons of her blouse. This revealed her ample cleavage, which glistened seductively as she fanned herself with a clipboard.
Bart had rarely seen Edna Krabappel as anything more than a naggy and unmotivated educator who didn't feel the slightest bit of guilt giving her students an F. Oh, how wrong he had been. Despite her tired face and apathetic attitude, Edna was a diamond in the rough. Her surprisingly huge breasts had maintained their youthful firmness and looked incredibly inviting as she lazily leaned on the podium.
Bart wondered what it would be like to get a titfuck from her. Would she be cutely embarrassed about it, or would she totally take control of the situation, confidently squeezing his cock between her soft tits and bouncing up and down while looking at him with half-closed eyes and a cheeky smile? Or perhaps she would perform the filthy act with her usual lack of energy as if it was a routine not worth getting fuzzy over. "Oh, let me guess, Bart. You want me to milk you dry with my tits again? Okay, let's get it over with".
All of these scenarios seemed equally pleasant. But there were other important things to consider as well. Like did Mrs. Krabappel prefer to get the cum on her breasts, her face or her mouth? Letting her finish him off by sucking the tip of his penis while the shaft of his penis was still sandwiched her breasts would certainly be an acceptable outcome. But a part of him also thought that it would be hotter to cum on her boobs as a way of marking those magnificent mammaries as his personal property. There would be no better way to reverse their student-teacher relationship than covering her in semen.
But those alluring mangos on his new favorite teacher's chest weren't the only thing making Bart's pants tight during that class. Whenever Mrs. Krabappel turned around to write on the black board Bart's attention was immediately directed at her tight posterior. Had Edna always been such a sex goddess and he simply didn't notice? Maybe the hottie had started doing squats in her midlife crisis, because not every woman her age had round and firm buttocks like that.
Edna's ass was not quite as big as Marge's, but it had its own special draw. Marge's butt was a certified MILF ass of a mother of three who did not exercise much, but maintained a healthy diet. As a result Marge's behind was more jiggly while maintaining its feminine shape. Edna's ass, on the other hand, still had a more youthful firmness while having grown in natural tandem with her age. The only question was, who was she trying to seduce by working out her glutes? Surely, she must have given up on Principal Skinner by now.
"Bart! Get up here and solve this problem," Mrs. Krabappel called all of a sudden. This was the worst possible time. Bart had just been in the middle of imagining what kind of naughty face Edna would be making after getting anally creampied. And now he was supposed to walk to the front of the class where he would be just inches from that slutty cocktease of a teacher.
"Umm, I don't know the answer," Bart said frantically.
"I know. Just try your best," Edna said with clear disinterest. "The new regulations force us to engage all the students in class regardless of whether or not they're academically gifted. So just shut up and get up here already."
Bart reluctantly got up from his seat while trying to cover his crotch with a notebook.
"HA-HA! Bart's got a boner!" Nelson pointed and laughed. There was a mix of laughter from the boys and the girls sounding disgusted.
"Nelson, watch your language!" Edna reprimanded, but the slight blush of her cheeks showed that she was clearly trying to move on from the subject. She was clearly fidgety as she handed Bart the chalk while avoiding looking at him.
Wow, I never thought that would get such a cute reaction out of her, Bart thought. It almost made him forget how humiliating the whole situation was. He didn't expect her to be that embarrassed about one of her own students getting an erection.
After the bell rang to signal the end of the school day, Bart rushed to the boys' restroom. He had had too much stimulation for one day and he was about to burst. He pulled out his phone and typed the name of his favorite porn site on the search bar. But as the site opened, nothing really caught his eye on the front page. It was the same old stuff. There was no way he could fap to something he had seen a million times, no matter how turned on he was. If only there existed porn stars who looked like Lisa, Marge or Edna. But that was a tall order. Natural beauties like that were hard to come by. Not to mention Lisa was underage…
Damn it! What should I do? Bart thought, the sexual frustration driving him desperate. He had a burning need to masturbate, but no material could compare to the visual bliss he had witnessed that day.
"That's it! I just need to get some material!"
Bart started typing a text message to Marge.
Hey mom, could you send me some photos of you wearing that necklace you always have? Milhouse's dad is thinking of buying a similar one to win his wife back and we wanted to help him out. Send multiple pictures from different angles so we can be sure that he gets the right one.
It was an ingenious plan. This way he could get a picture of his mother's cleavage without raising any suspicion. Marge's reply came within a couple minutes.
Here you go, sweetie. You're such a good boy for helping Kirk get back together with Luann. I am so proud of you!
Bart almost started drooling with anticipation as he pressed to open the first attached image with shaky fingers. Bingo! The very first picture was taken from a slightly downward angle, showing the beautiful canyon between Marge's perfect tits. Her innocent smile made it clear that she had no idea of the effects this angle had on her son. Bart immediately grabbed his dick and started stroking.
"¡Ay, caramba! I am the luckiest son in the world," he whispered under his breath. He had once been a little baby who had gotten all of his nutrients from that bosom. If only he could still suck on her nipples and drink her sweet milk. "Ooh, mom. Look what you've turned me into. This is your fault for being such a MILF. You wouldn't have sent me this hot picture if you didn't want me to blow my load to it."
Bart was getting close. He pinch-zoomed into the cleavage and imagined he was motorboating the breasts. That did it. "Ahh, take this, you big-titted whore!" he mumbled, biting his lip as he ejaculated. He wanted to cum on his phone screen and make it look like he had really given his mom a bukkake, but that would have been a pain to clean up, so he simply finished in the toilet bowl. He basked in the afterglow of orgasm for a couple minutes while continuing to stare the picture. "Ahh, I love you, mom. You're such a dream woman…"
After flushing the toilet and washing his hands, Bart felt a sense of shame wash over him. The realization was starting to sink in that he had just masturbated to a selfie of his own mother. Not only that, in a fit of uncontrolled lust he had even viewed her as a whore who existed for pleasuring him. This couldn't be taken back. He had broken a taboo and had no choice but to admit he really had an Oedipus Complex.
This cannot lead to anything good. At this rate I'm not going to be able to control myself at all when I'm home. Maybe I should go see a shrink.
That night Bart browsed the web for hours, looking for a cure for his mental condition. He really had to get it fixed or daily interactions with his mother and sister would become impossible. Unfortunately, none of the forums proved helpful. Surprisingly many posters were even talking about the good sides of consensual incestuous relationships.
"Ughh, these guys are even more messed up than me," Bart grumbled, but he kept reading the thread. "He seriously convinced his mom to give him a blowjob and it worked? In what reality does that happen?"
Still, the idea that incestuous feelings could be mutual and develop into a consensual sexual relationship… that planted a seed of an idea in Bart's mind.
But there's no way mom would cheat on Homer. She's such a good person that her morals wouldn't allow infidelity… especially with her own son.
Bart sighed and was about to close his laptop when his eyes spotted an interesting word on the thread. One of the posters was talking about hypnosis. Apparently there was a device called HypnoBox, which could be bought on the backends of the internet. Supposedly it could be used to hypnotize anyone to follow your commands. This poster had used the device to convince his aunt to have sex with him and there were a dozen others vouching for the product.
Bart immediately began a search for a website where HypnoBox was being sold. It took a bit of digging, but he found it. Not hesitating for a second, Bart sneaked into his parents' bedroom. Homer and Marge were already asleep. The spiky-haired boy moved slowly toward the nightstand on his father's side of the bed. Homer usually kept his wallet in the upper drawer. Bart had 'borrowed' his credit card a couple times in the past, so he was not particularly worried about being caught. This was a simple heist for a regular hellion like him and there was little that could go wrong. Even if one of his parents happened to wake up, he could just say he had had a bad dream. Marge would comfort him and let him sleep in their bed. It worked every time.
The devious young man snatched the credit card from Homer's wallet and left the room as silently as he had entered. Perfect execution. In fact, it had been so easy that Bart craved a little something more challenging. He thought for a moment and stopped in front of Lisa's room. He put the credit card in his pocket and cracked the door to peek inside. Lisa was fast asleep.
Bart walked next to his little sister's bed. Lisa was sleeping on her side, facing away from the door. Her breathing was steady and the blanket was gently rising up and down around her chest. Bart knew he was pushing his luck, but he needed a little thrill before using the credit card to buy the hypnosis device. After all, once he had that, both Lisa and Marge would do whatever he wanted. It didn't hurt to gloat a little so close to the finish line.
"Hey Lis," Bart whispered, knowing full well that the little brainiac was out cold and couldn't hear him. "Guess what? I'm soon gonna turn you and mom into my personal cocksleeves. And I bet you're gonna love it. I know you like to act all smart and moral, but I know deep inside you just want guys to fuck you."
Bart stopped for a moment. Maybe he shouldn't go further until he actually held the hypnosis device in his hands. It was possible that Lisa was just pretending to sleep or could hear his voice in her dream. But then again, if his theory was correct, she probably didn't mind being talked to in such a degrading way…
"Come to think of it…" Bart pulled down the blanket, revealing the spiky-haired little girl's backside. She was wearing a pink one-piece pajama. "I haven't gotten a good luck at your ass since we were toddlers. That orange dress you always wear doesn't do much to show off your curves. I wonder how you compare to mom."
The boy gently pulled up the bottom his sister's pajama. Her firm butt cheeks wobbled into view with a slight bounce as the fabric pulled up on them. She was wearing panties, but they were a surprisingly bold design for a girl as serious as her, disappearing into her tight crack. Bart was mesmerized. Even in the darkness of the room he could make out the subtle shape of Lisa's developing hips. Compared to Marge's and Edna's huge asses that practically burst out of their clothing, Lisa's young preteen ass was a much humbler effort. But that was a part of the appeal. While Marge's and Edna's butts enhanced their mature appeal, Lisa's cute booty had the charm of a forbidden fruit. For a girl her age, she showed a lot of promise.
"Okay, I think that's enough screwing around," Bart said. "I'll be going now, Lis. Time for your brother to kiss you goodnight."
With that he knelt down, leaned over and kissed both of her buttocks. Lisa moaned quietly as his lips touched her warm butt cheeks. After that he took a picture of his sleeping sister for his fap collection. He didn't know how long the delivery of the hypnosis kit would take, so it was a good idea to gather as much relief material as possible in the meantime. After that, he tucked Lisa in again and left the room.
With Homer's credit card information, the horny young man was able to successfully place an order for the HypnoBox. The estimated delivery would only take a few days, since he paid for advanced shipping. After receiving the email confirmation, Bart once again questioned what he was doing. He had never been a good kid per se, but this was without a doubt the vilest thing he had ever done. He had used his dad's money to buy an illegal device to turn his mother and sister into his personal sex slaves. Was this really what he had become?
Bart looked around his room while contemplating if he should call the whole thing off before it was too late. Sure, it would totally erase all his pent up sexual frustration if he was able to make Marge and Lisa into his whores, but would he be able to live with himself being that selfish? Bart's wandering gaze fell on the label maker he had received from Patty and Selma as a birthday gift. He remembered having had fun with it for a while, labeling everything in the house as "Property of Bart Simpson." Now he was on the cusp of making his own family members his personal property to be used as he saw fit.
Bart's thoughts returned to Lisa's succulent ass. And then Marge's. Then Lisa's again. Then he imagined them side by side, presenting their hindquarters for him as he labeled them both with the "Property of Bart Simpson" sticker. How empowering and erotic it would be to have them walk around town with those labels on the lower backs of their skirts. They would let everyone know that their asses belonged to him and him alone.
"What am I having a cow for? Screw hesitating after having come this far!" Bart declared to himself. If he was already so depraved that he was sexualizing his own mother and little sister, he might as well go all the way with it. You only live once after all. If he was meant to be a bad boy he would be the baddest boy of them all and follow his desires wherever they took him.
With renewed determination, Bart started sneaking back into his parents' bedroom to return the credit card. He entered the room with silent footsteps and walked up to the drawer. Soon the credit card was back in Homer's wallet and the operation was officially complete. Now he just had to return to his own…
"MEOWWW!"
"Crap!"
In the darkness Bart had not seen Snowball's tail peeking from under the bed and he had stepped on it. Miraculously, Homer kept sleeping, but Marge turned on the reading light and rubbed her eyes.
"Bart? Honey, what are you doing? Did you have a bad dream again."
"Uhh, yeah, mom. It was really scary."
"Come here, sweetie," she yawned. "Just don't wake up your father."
Now that it had come to this, Bart had no choice but to crawl on the bed between his parents. It didn't matter, he had already completed his mission, so the room where he spent the night really didn't make a difference. Except for Homer's loud snoring, of course…
"Good night, my special little guy," Marge said before turning off the lights. She normally slept on her back, but she rolled on her side away from Bart to make more room for him.
On any other night, Bart could have just gone to sleep right there (after burying his head under a pillow to muffle the sound of Homer's snoring). But now that he had awakened to the sexual feelings he had for his mother, it was impossible. He quietly looked at his mom's back as her breathing became steady. He called her name to confirm that she had already fallen asleep again. There was no reply. Although Bart couldn't see under the blanket, he knew that if he moved just a little, he could touch Marge's ass.
I kind of pushed my luck with Lisa. But mom's a much lighter sleeper, so I really shouldn't…
But then again, he had already decided what he was going to become. A true incestuous sleaze wouldn't back down from a golden opportunity like this. He could just pretend he was fumbling around in his sleep. That was a plausible story if she managed to wake up. She wouldn't suspect a thing.
Once again having justified his lusty intentions, he reached his hands forward and grabbed the mounds of her flesh. The warm softness was so inviting that he immediately started kneading his mother's plump derriere as if he was mixing dough.
"Ooh, Homie… not here…" she muttered half-asleep. Bart's heart stopped for a second, thinking he might get caught. But when Marge's steady breathing resumed, so did he. The curious son played with his mother's ass, pulling her cheeks apart and letting them fall back into place with a quiet clapping noise.
"Mom, this is your fault," Bart whispered in Marge's ear. "You made me this way. That day when you sat on my face I realized that you have the most perfect ass in the world. You used your sexy body to seduce your own son, and now I'm going make you into my bitch."
"Unnnf…"
Marge moved in her sleep, pushing her hips backward, grazing Bart's hard penis.
"Oh, you're ready to take responsibility? Good." Bart said cockily. He spread Marge's butt cheeks apart and pushed his dick between them. "You've already made me cum with your tits, mom. Now it's time for me to cum with your ass."
Plausible deniability was on his side once more. Marge had cleaned his bedsheets enough times to know that nocturnal emissions were normal for a boy his age. For all Marge knew, her son had simply experienced an erotic dream when she would wake up with his slimy love juices on her bottom.
Bart moved his hips up and down, sliding his throbbing member up and down Marge's ass cheeks. His only regrets was missing the visual spectacle because the blanket was blocking the view. He could feel the enormous mounds completely swallow his dick as if to tuck it in with her motherly warmth. The inner curves had a layer of sweat that helped lubricate the motion, allowing Bart to move effortlessly. The flowing precum made the back and forth motion sound like someone was squeezing a wet sponge over and over again. The bed was creaking gently as he picked up the pace.
"Ahh, take it all over your big yellow ass," Bart whispered as he ejaculated. Although the blanket was covering the view, he knew he had made a big mess. Marge groaned in her sleep and adjusted her pose, causing Bart's cock to plop free with a wet sound. She would be in for a surprise when she woke up in the morning. But naturally she wouldn't blame Bart for it. He was just a healthy hormonal boy who occasionally had wet dreams. There was nothing particularly strange about the whole situation even if it was pretty awkward. She probably wouldn't even bring it up.
Man, I can't wait to be able to do this stuff without having to hide it. It's gonna be great.
