Chapter 7: Date Night

Bart spent the rest of his Saturday studying at the library. He had told Lisa about his plan to get his grades up and she was very proud of him. They both agreed that it would be best if he studied outside the house to avoid distractions. If the boy studied at home he would probably just end up fooling around with his sister all day. He wasn't the least bit happy to spend his weekend with his nose buried in books, but he had a test coming up on Monday and it was his chance to make Mrs. Krabappel proud.

Mom, too, will be beyond happy too if she sees my next report card showing A's and B's instead of C's and D's, the boy thought optimistically. As much as he hated studying, it seemed like a possible path to making the two mature women in his sights finally open their legs for him. Lisa, for her part, had her own school projects to catch up on. She seemed less interested in school work lately, but Bart would feel bad if she actually started falling behind because of him, so they both decided to do their best.

After finishing another chapter of the tedious history textbook, Bart looked at the clock. He had already spent four hours studying. If he was home with his sister, Lisa would have probably made him cum at least three times in that time. It was definitely a good call to get into a distraction-free environment. Bart packed up his studying materials, since the library was closing in a few minutes. He dreaded having to come back for another study session tomorrow, but it had to be done if he wished to win his bet with Mrs. Krabappel.

The boy stepped out of the library and grabbed his skateboard leaning against the bike rack. He was so exhausted that he could barely stay awake for the ride home.

When Bart arrived back at his house, he found Marge sitting alone at the dinner table with a glass of wine. The blue-haired woman was wearing a fancy red dress that showed a lot of cleavage. She also had put on blue eyeliner and lipstick. Her expression was sour and her eyes were slightly unfocused due to the alcohol.

"Hey, mom. Is Lisa home yet? She told me she was going to a museum today for a research project."

"Lisa won't be home until Sunday evening," Marge said absentmindedly. "She said she wanted to stay out of your way while you studied for your test, so she's at a Buddhist retreat."

"Oh. Guess I gotta really do my all and study while she's gone then. Anyway, how was your date night with dad?"

"It was great," Marge replied bitterly while sipping her wine. "He took me to an expensive restaurant and we had a great time."

"Then why do you look so mad?" Bart asked, although he could guess the reason.

"Your father… he's been acting so distant lately," the woman confessed, leaning her chin on her palm. "I mean, he's great in almost every way. He got promoted to a managerial role at work and was even nominated as the employee of the month. He does all the household chores without complaints and babysits Maggie when I'm busy. He just put Maggie to bed before going to celebrate his promotion with his coworkers. He's a really good father now… But whenever I ask him to… ahem… snuggle, he always has an excuse not to do it. He's got a headache, he's too tired, he's got to file employee review reports… I've heard it all. He's always busy and has time for anything except me."

"Sounds rough," Bart said, feeling a little guilty. He had brainwashed Homer to reject Marge's advances, so all of this was his fault.

"It makes me wonder…" Marge continued, swirling her finger around the top of the wine glass bitterly. "Am I just at that age where men don't find me attractive anymore?"

"No, mom!" Bart said. "Don't think for a second that you're not a total catch! You're one sexy mama! If I were your husband, I'd snuggle with you every single night!"

The boy realized that he had used the word 'sexy' in the heat of the moment. He half-expected to get another lecture from his mom, but instead the mature woman smiled happily.

"Thanks, honey. If I were your wife, I know you would take care of all of my needs."

Bart's dick twitched in his shorts. Even if they were speaking in hypotheticals and he was just trying to comfort his mother, it sounded like she had actually imagined being in a sexually intimate relationship with her own son! Perhaps the alcohol compounded the effects of the Pheromone Pill, making her easier to manipulate than usual.

"Bart?"

"Yeah?"

"Could you… take me to my bedroom?" Marge slurred and hiccupped. "I'm a little tipsy and I don't want to stumble going up the stairs."

"Sure thing, mom!"

The young boy gave support to his mother as she stood up shakily. She leaned lightly on his shoulder with her left hand as they walked. Bart reached his right hand over and rested it on Marge's right buttock.

"Where do you think you're touching, young man?" the woman asked, but she sounded quite playful about it. There was a subtle smile on her tired face.

"Where else do you expect me to support you? I'm half your size."

"Hmm, I guess you're right."

The two arrived at the bottom of the stairs.

"This is the hard part. You better hold on to me tight, Bart."

"Yes maam!" Bart said and proceeded to squeeze Marge's butt.

She gave him a mischievous look. "Ooh, you dirty boy. You've had your eyes on that for a while, haven't you?"

"Oh, you noticed?" Bart said cockily. Things seemed to go very smoothly. "Homer is an idiot who doesn't know what he's missing out on. I say you forget about him for tonight and let me take care of your needs."

"Bart… I'm your mother, you know."

"You don't have to be tonight. Tonight you can be my whore. And I'll be your stud. Let's make Homer jealous together."

"Bart…"

Her son only answered by massaging her ass, which the older woman allowed.

Since Lisa wasn't home and Marge was acting surprisingly horny due to the combined effects of alcohol and the Pheromone Pill, this was the ideal opportunity to take things all the way. When the mother and son got to the bedroom, Marge immediately took off her dress. She was wearing a sensual white corset and g-string combination under it. She had clearly prepared for a romantic evening of lovemaking with her husband. She threw herself forward onto the bed and presented her amazing ass to the boy who still stood at the doorway with his jaw dropped. He had never seen this sexually assertive side of his mother. She was wiggling her hips like a stripper while giving him the 'fuck me' eyes. Bart took a single Pheromone Pill from the can in his pocket before stripping his clothes and getting behind Marge on the bed.

"Bart, what's that thing in your hand?"

"I'm gonna put this in your ass. Trust me, it feels really good."

"In my ass? Uh, okay then," the mature woman said and obediently opened her butt cheeks for him while biting her bottom lip.

"That's a good girl."

Bart pushed in the Pheromone Pill while Marge moaned. Her pussy was already overflowing from just this. She had really looked forward to some sex with Homer tonight, so it was no wonder that her body was so sensitive. Bart took his finger out of Marge's ass and slid it into her pussy.

"Ahh, yes!" Marge screamed. Given how turned on and wet she was already, there was no need to take it slow. Bart started fingerfucking his mother's dripping cunt so fast that his hand was just a blur. Marge was rocking in rhythm like she was possessed. She was making the sort of pornstar-level moans that Bart could never have imagined coming from his own mother. She was normally such a morally upstanding and dorky yet loving housewife. Yet here she was drooling with her tongue hanging out while getting fingerbanged by her underage son. The vulgar sounds of her flooding vagina reminded Bart of the sounds of a bunch of small kids jumping around in a puddle of water.

"Ooooohhhh!" Marge gave her loudest scream yet while she squirted. She arched her back as if she was being puppeted by invisible strings and her whole body trembled in place for a few second. When Bart withdrew his finger, the woman collapsed forward, still twitching from the orgasm. She was panting like she had just ran a marathon.

"I'm not done with you yet, whore," Bart said. "That was just the appetizer. Now it's time for the main course."

Bart lined his cock up with Marge's plump pussy lips that were moist with her juices. "I bet you never thought when you pushed me out of that vagina that you would see me grow up to fuck that same hole."

"No, Bart," Marge said apologetically and covered her pussy with one of her hands. "You can't put it there. I might get pregnant."

It looked like Marge still had some of her motherly sense of responsibility left. Even at her most horniest she still could not justify inbreeding.

The heavily breathing woman put her hands on her butt cheeks again and spread them apart. "You can fuck me here, sweetie. It would be selfish of me not to make you feel good after you got me off."

Bart smiled to himself. "Oh, wow, anal sex? I don't know, mom. I feel bad for you having to take my cock in your ass. I hear most women don't really enjoy it and only do it to make their boyfriends happy. I'll just go to my room and jerk off."

Bart got off the bed. Naturally he wasn't actually turning down Marge's proposal, but he wanted to see if a little bit of reverse psychology would make the drunk woman more honest with herself.

"Wait, Bart!" she stopped him right on cue. "I'm not doing this just for you. It… feels really good for me too. I might even… prefer it..."

In a matter of seconds Bart was back on the bed, grabbing his mother by the hips and poking the tip of her penis against her asshole.

"Hurry up and put it inside," Marge pleaded.

"Well, well. Someone's eager," Bart teased. "Admit it, mom. You've been teasing me with your big butt for weeks because you were secretly hoping this would happen."

"It's true," Marge said with tears of shame falling down her cheeks. It seemed that even in this state she realized that what she was doing was beyond wrong. "All those times I caught you looking at my ass and scolded you… I was secretly enjoying the attention. You're the only man in my life who actually sees me as an attractive woman. I was hoping that if I teased you enough, you would give in to your lust. I wanted you to overpower me, bend me over and fuck my big ass!"

"You should've just been honest from the start," Bart said. "But better late than never. Because your wish will come true tonight."

He pushed his hard cock in Marge's ass all the way. The horny mother's asshole accepted her son's dick with ease. Although Bart had anally penetrated her before, this time she was fully awake and giving him permission to do it, which made the taboo act all the more hotter.

"Ooohh, so deep!" Marge slurred with her eyes rolling upward in pleasure.

"You think that's good? We're just getting started!"

Bart started humping the blue-haired beauty like a dog in heat. Every now and then he pulled his cock out and admired the gape of Marge's winking asshole. But he couldn't keep his dick out of there for long. His mother's gigantic yellow ass drew his cock back in like a magnet every time. The young man made her face the mirror on the side of the room so that he could see her sexy expressions while he slammed her bouncing booty. The woman was completely lost in pleasure. Her eyes were crossed and her tongue was hanging like a panting dog. The words escaping her mouth weren't even intelligible anymore. The tears of shame running down her face had turned into tears of mad ecstasy.

Marge gave a similar extremely high-pitched yelp as before when Bart had been fingering her. Transparent liquid squirted out of her pussy. It looked like she had orgasmed again.

"Wow, you really came from me fucking your ass?" Bart said, giving his mother a few spanks while he kept humping her body that had gone limp. "That's your weak spot, isn't it? You really are an anal whore."

"Yesshh… I lovhe ith… mah spechial lithle ghuy… doingh mah butth…" Marge talked like a little child with her drooling tongue still out. Her eyes were wide open and staring mindlessly upward as if she was drugged. She bit her bottom lip as her son kept mercilessly poking the g-spot in her anus with his cock.

Bart himself was getting very close. "I'm gonna cum, mom. I'm gonna shoot my jizz so far up your ass that it'll come out of your mouth, so get ready!"

"Yeeesh! Yeesh, chum inshide mah assh!" the incestuous slut begged.

"Here it comes! Take this, whore!" the boy put his whole weight behind the last thrust and started ejaculating. "Aaaah, fuck! I'm using your body for its intended purpose, mom. Your asshole was made to be my personal semen tank." Marge trembled and gave a quiet squeal. She had already used up all of her voice moaning so much, but Bart could tell from her erratic twitching that the woman had orgasmed for a third time as his semen splattered its way up the walls of her anal cavity. Marge's well-trained anus tightened around Bart's dick, refusing to let go until he had finished emptying his balls inside her.

When the spiky-haired boy pulled out his cock, a waterfall of thick semen came pouring out of Marge's stretched butthole.

"We're still not done, whore," Bart said. "Turn around. It's time for you to clean up your master's penis."

Marge obeyed wordlessly. She turned around on the bed, bent down toward the boy's crotch and started sucking him off. Bart grabbed the back of her head with both hands and started to roughly facefuck her. Although his penis was limp because he had just ejaculated, the feeling of dominating his own mother like this was just too exciting to pass up.

"Gluggluglug…" was all Marge could say with her son's member forced back and forth inside her drooling mouth.

"Yeaah! You like the taste of my penis mixed with the taste of your own asshole?" Bart said victoriously. He couldn't believe that on that same morning his strict mother had been scolding him for looking at her butt. Yet here she was deepthroating him after he had creampied her ass.

"Mmflghl!" Marge could only make sloppy guttural noises with her mouth stuffed. She was looking up at her son submissively while he kept violating her throat. The depravity of the situation made the boy get hard again. Marge could feel his limp dick growing big again until it was poking the back of her throat. Marge's eyes filled with tears and she started choking a little. Bart pulled his cock out to let her breathe.

And enormous amount of saliva streamed out of the woman's mouth as she caught her breath. She proceeded to lick the length of Bart's shaft. Even when she was given a break, she wanted to keep tasting it. Mascara was running down her cheeks, making her look like a total whore. Marge didn't usually wear heavy makeup, so Bart had never seen her face be such a mess.

"Okay, break time's over," Bart announced. "I'm gonna enjoy your mouthpussy some more!"

"Ahh!" Marge opened her mouth wide open like a well-trained prostitute. Bart rammed his cock in and started facefucking her once more. He was using his mother's head like a masturbatory toy, pulling her back and forth at his own pace with little regard to how she was struggling to keep up.

"Gluggluglug! Mmmfh! Ooplmmp!" Marge's eyes crossed again as she was starting to adapt to the pace. Her lips wrapped even more tightly around the penis that was mercilessly assaulting her mouth. Whenever Bart was pulling outward, the suction of her lips caused them to extend along the length of the penis. She was making a blowjob duckface. This combined with her crossed eyes made her look quite silly. But for Bart it was the hottest expression in the world. She was so lost in pleasure that she had completely lost her mind in that moment.

"I'm cumming in your mouth, mom! Drink it all!"

He pushed his dick so far down Marge's throat that his balls were resting on her lips. He had already ejaculated just a few minutes before, but his load was still quite substantial. Marge gulped it all down obediently. Not that she had any choice with Bart forcing her mouth all the way to the base of his ejaculating cock by pulling on her head.

Both mother and son collapsed down on the bed. They had gone all out and were beyond tired now.

"Haaah… I love you, mom." The boy said with an exhausted sigh of relief.

"I love you too, honey," Marge replied with an intoxicated smile and half-closed eyes. "But you should go back to your room before your father gets home. If he catches us like this, he'll be furious."

"Good call."

Bart knew that Homer most certainly would not get furious on account of being brainwashed. But he didn't feel like explaining that to his mother. If she still had any sense of parental responsibility left, she wouldn't be happy that he had hypnotized Homer.

"Good night, my anal queen."

"Good night, my sweet little stud."