Chapter 15: Mother's Day

During recess Bart approached Martin at the lockers and pulled him behind the corner away from prying eyes.

"Wh-what is it, Bart? I already told you everything you wanted to know about the pills," Martin quivered.

"Don't worry buddy, I just want to talk business," the young man said coolly. He pulled out a Pheromone Pill from his pocket and placed it on Martin's palm. "I've got an infinite supply of these babies now. If you agree to work for me, I'll give you one pill every week."

"Really?!" Martin exclaimed.

Bart shushed the other boy and looked around suspiciously before continuing.

"That's right, man. You'll get to have fun with Ms. Hoover as much as you want without having to pay a fortune. All you need to do is vouch for me at the hearing."

"Hearing? You mean about your expulsion for using a taser on Jimbo?"

"That's right. You will be my star witness. Use your straight A-student street cred to really convince all the teachers and parents of my innocence."

"I'll… I'll try my best, Bart," Martin said.

Next it was time to convince Milhouse. During lunch Bart sat opposite to his former best friend who was eating his fish sticks alone.

"Bart! Why are you sitting to eat lunch with me? I thought you didn't want to be my friend anymore."

"I don't. But we can at least be allies. I need you to take my side at my expulsion hearing."

"Hmm…" Milhouse pondered for a few second. Then his face twisted into a devious smile. "I guess I could help you out if Lisa sucks on my weewee again."

Bart almost reached across the table and grabbed the four-eyed dweeb by the collar, but he managed to keep his composure, and took a deep breath.

"I can't promise that," he said sternly. "But I can give you something almost as good."

He dropped a Pheromone Pill on the table.

"Is that…?"

"Yeah, it's the stuff I made you steal from Jimbo's house back then. If you make a woman swallow this pill you can make her do anything you want. You have my permission to use it on anyone other than Lisa, Mrs. Krabappel or my mom."

Milhouse stared at the pill intensely. His mind flashed back to the night when he had broken into Jimbo's house and saw his mother naked on the floor being roughly handled by the three bullies. Blood rushed to his nether regions at the arousing memory.

"Let's say hypothetically," Milhouse started, shaking with excitement, "that I gave the pill to my mom. Would it still work?"

"Yep," Bart replied with a smile.

"I could make her do anything? Even…"

"Even the stuff we did with Lisa at the treehouse? You bet."

"I'm in!" Milhouse said and grabbed the pill off the table.

"Truce?"

"Truce."

The two boys shook hands.

After the school bell rang signaling the end of the final period Mrs. Krabappel asked Bart to stay after class. The boy was more than happy to oblige, but to his disappointment the sexy teacher looked sad.

"Well, Bart. Your hearing is coming soon. Even if I managed to convince Skinner that you weren't to blame for the incident, I don't see how we can make all the parents agree that you shouldn't be expelled. So I guess this will be our last week together."

"It'll be fine, Mrs. K."

"How can you be so calm? Oh wait… I suppose expulsion doesn't really mean anything to a troublemaker who hates school. You're getting exactly what you want, aren't you?"

"I don't hate school," Bart protested. "Well, okay, I do… but having you as my teacher at least makes it tolerable!"

"Hah, you flatterer," Edna rolled her eyes with a slight smirk forming on her lips. "It might sound crazy coming from me, but I'll really miss having you in my class."

"Tell you what, Mrs. Krabappel," Bart said. "Why don't we have another wager? If I do get expelled, I'll buy you tickets to a fancy spa. You've earned yourself some relaxation for all your hard work. But if I manage to not get expelled you'll have to give me what I want."

"Mmh, and what would that be?" the brunette woman asked, entertaining the implausible idea.

"You'll have to give me a tittyfuck!" Bart proclaimed without any hesitation, pointing at his youthful teacher's bountiful chest.

"A tittyfuck?" Edna flinched, causing her protruding chest to jiggle slightly. "Where is this country going when ten-year old boys know words like that? I'm beginning to regret letting you jerk off to my boobs that one time…"

"Are you chickening out? You seemed so sure a second ago that I would get kicked out."

"Hmpf. I'm not backing out. I look forward to those tickets to the fancy spa."

"And I look forward to sliding my cock between those gigantic melons."

"Hah! Keep dreaming."

The two smirked at each other. The wager was on.

On his way home Bart stopped by Professor Frink's house to get a refill of the Pheromone Pills. He also picked up a special vibrating buttplug he had commissioned the egghead to build for him. It was his Mother's Day gift for Marge. The flat end of the buttplug was in a heart shape and had text reading "The World's Best Mom". There was no doubt that the horny housewife would love such a thoughtful present.

When the boy arrived home his whores were already hard at work training their holes for him. Marge was deepthroating a huge wall-mounted dildo, her drool dripping to the floor and making a puddle. Whenever the blue-haired woman started to gag, Lisa gave her instructions on how to take the dildo deeper inside her throat. The spiky haired girl for her part was behind her mother, her hands firmly pulling apart her mother's fleshy butt cheeks and rimming her rapidly winking asshole.

Behind Lisa was an automated sex toy that was robotically thrusting two heavily lubricated medium-size dildos in and out of her developing holes.

Bart immediately dropped down his shorts and joined his family in the living room.

"Move aside, sis," he said, tapping Lisa's shoulder gently. "Let me have a taste."

Lisa pressed a remote to turn off the machine fucking her, pulled herself off the dildos and stepped aside like a well-trained sex slave.

"Give it to her, Bart. I got her all warmed up for you."

"Bon appetit," the boy said before running his tongue from Marge's soaked pussy all the way up to the top of her ass crack as if it was a melting popsicle. He could taste the sweetness of his sister's saliva in every inch of his mother's ass. While he was lost in the caverns of his mother's voluminous buttocks, Marge pulled her face back and let the giant dildo flop out of her mouth like a huge slimy fish.

"Oh Bart, I've been going crazy waiting for you all day. Stop teasing mommy and stick it in already."

"Not today, mom," Bart said. "I wanna try fucking your mouth today and see how far you've come in your deepthroat training."

"She's getting pretty good," Lisa said while licking the dildos that had been penetrating her holes a moment ago. "I've taught her pretty much all I know. Now all that she needs is more experience with the real thing."

"Interesting," Bart mumbled. He then returned his attention to the huge housewife-ass in front of his face and started licking and sucking on Marge's lewdly inviting asshole. "But don't worry, mom. I won't neglect your favorite hole either."

The boy licked circles around the edges of Marge's intoxicatingly delicious rectum that was still slightly dilated from some earlier dildo fucking. Every now and then he thrusted his tongue inside her as deep as it would go and wiggled it around. The blue-haired woman howled with mad pleasure and reached her hands behind her to pull her son's face to press even more tightly against her fat behind.

"Oh my god, Bart! Your tongue feels so good! It's almost as good as your dick!"

"I could eat your ass all day, mom! But I can't hold back anymore. I want to make you gargle with my cum like the cockloving gutter whore you are."

"Give it to me, big boy. I'm ready."

"But first…" Bart interrupted Marge by slapping her ass just as she was about to turn around and present her mouth. "I've got a little present for you. Happy Mother's Day!"

The young man pulled out the custom buttplug.

"Bart, don't you think Mom already has enough sex toys?" Lisa said dryly.

"I can guarantee she doesn't have one like this," Bart said. "It was custom made to have the exact circumference of my cock. Also, it has a remote vibration function and a cumshot option. I filled the tank with my own semen, so whenever mom gets horny while I'm at school, she can use this to get her fill of me."

"Oh Bart, that is so thoughtful of you," Marge said. "May I try it right away?"

"Of course! Spread your ass for me and I'll slide it in."

With her read up, Marge lay her upper body forward and spread her ass cheeks as far apart as they would go. Strands of sticky saliva were forming bridges between the two hemispheres of her yellow booty. Using her vast anal sex experience she relaxed her muscles to allow her rectum to open up for the insertion.

The buttplug slid in with relative ease thanks to the lubrication. Marge's well-trained asshole closed snugly around the toy until all that was visible was the heart-shaped end part that said "World's Best Mother".

"Oooh, I love it, Bart! This is the best present a mother could ask for."

"I'm glad you like it. Promise to wear it every day while I'm not available."

"I promise!"

"Even at church or a fancy restaurant?"

"Yes!"

"And what will you be thinking the whole time?"

"About my son's huge monster cock inside my slutty asshole!"

"That's a good bitch. Now let's test drive that mouthpussy of yours."

"Hurry up with mom so I can get a turn too," Lisa complained while fingering her pussy on the floor with a jealous look. She then addressed her mother. "Mom, remember what I taught you. Open up wide and focus on the front of your mouth. Breathe through your nose. Keep eye contact. Remember to move your tongue up and down the shaft. Remember the vacuum sucking technique. If you do all that, Bart will cum in thirty seconds flat."

"Wow, you've really got this down to a science," Bart commented. "Well, mom, are you ready to show me what you've got?"

"Give it to me, stud," the youthful housewife said with half-closed eyes. "No need to go easy on me. Mess me up."

"Are you sure?" Bart asked, barely containing his urge to start thrusting. "I know you're still a beginner. I don't expect you to be as good as Lisa quite yet."

"I'm sure. I can't let my eight-year old daughter beat me. Go all out. Fuck my mouth as if it was Lisa's."

"Well, if you insist…" Bart shrugged and grabbed the sides of Marge's head. "Open up."

"Ahhh…"

"Oh, you're gonna get it now, you horny bitch!"

Bart pushed his hips forward with force. His penis quickly penetrated the inside of his mother's wet and hot mouth to the point it was hitting the back of her throat and only his balls were left hanging in front of her bottom lip.

"Hmm, pretty good so far," Bart said, observing that Marge was not gagging. "But you can't just leave my balls hanging outside. Surely there's enough room inside your mouth for them."

The blue-haired woman's eyes opened wider. She had not expected this. She tried to open her mouth wider and push her mouth deeper to get to the testicles, but it proved difficult. The penis was already as far as it could go, so the only way forward was to make it bend down her esophagus, which was beyond her current skill level.

"Hffflbbp, mmmphffll, glgllgl".

She was desperately trying to maneuver closer to her son's crotch, but every slight push made it slightly harder to proceed.

"You need to do better than that if you want to get to Lisa's level," Bart teased. This seemed to motivate the whore as she forcefully pushed her face forward with renewed vigor while glaring at her son. Her eyes teared up a little, but with some effort she was able to get both of Bart's testicles in her mouth. She looked like a chipmunk that had stuffed its cheeks full of nuts.

"Oh god, mom! You look so hot glaring at me like that while choking on my dick. It makes me want to fuck your mouth even harder."

Now that he was convinced of Marge's skills, Bart started moving his hips back and forth at a rapid pace. As a reward to Marge for doing such a good job, he clicked on the buttplug's remote to cause it to vibrate in her ass. He had his thumb ready on the other button that would release the semen that was stored inside the toy. His plan was to activate it at the same time when he came in her mouth.

"Glug! Glug! Glug! Glug!"

The blue-haired woman made rhythmic guttural sounds in pace with her young stud's thrusting. Even as her teary eyes rolled up, she managed to keep from gagging.

Bart was ashamed to admit it, but he felt that Lisa's estimates had been generous. There was no way he could last even thirty seconds of this blowjob. While Marge's fellatio technique was still not quite on Lisa's level, the power dynamic of roughly fucking the mouth of his strict yet dorky mother made this experience that much more erotic. It was like he was punishing her for all the times she had been too overbearing with him. The mother who had always nagged at him to clean his room and stay out of trouble was now nothing but his personal cumdumpster. She had trained so hard just to please him with her mouth and he was going to take full advantage of that earnestness.

"Ahh, big bro," Lisa moaned while pleasuring herself. "You better save some of that energy for me. I've never seen you get that intense."

"Sorry, Lis. This bitch is gonna drain me for at least the next thirty minutes." Bart said. "I'M CUMMING!"

It felt so good that Bart almost forgot to press the button on the remote.

Splurt splurt splurt. Click. Splurt splurt splurt.

His load was so enormous that Marge couldn't possibly store it all in her cheeks or drink it in one big gulp. The semen burst through her nose in irregular intervals like a defective sprinkler. Bart pulled his cock out of her overflowing semen hall and rested it on her face while the last couple ejaculations rained the remaining splooge all over her face. She collapsed with a vacant expression, her face sideways on the floor, rivers of hot jizz flowing out of her mouth and nostrils.

Bart walked behind his mother and pulled out the buttplug. It popped out with a sound that was like a suction cup being pulled off a surface. Her asshole was now big enough to fit a fist, and a huge amount of thick semen came pouring out.

"Dinner is served, Lis. Enjoy your meal."

"Thanks, Bart."

The small girl moved on all fours behind her mother and started to suck out her brother's stored jizz from Marge's butt.

Bart walked back to the other side and pressed his mother's face against the pool of cum on the floor that had fallen out of her mouth.

"Drink it all up, whore. It's bad to waste good food, you know."

"Yes… sorry, master," the dizzy woman replied, still in a taste of stupor from the asphyxiation and multiple orgasms.

"That's a good girl. Happy Mother's Day."