Mommie Annie

 “HOW DARE YOU NOT TAKE OUT THE TRASH! YOU ARE GROUNDED, MALCOLM, FOR A WEEK, NO PHONE, NO INTERNET. GET IT RIGHT FOR ONCE!” 

Margaret Longwater, or Maggie as most people called her, was a woman approaching her 50’s but her age didn’t really show that much except in eye bags. She was thick in front and behind, with fine D cup breasts wrapped in a blue dress. Her brown hair, parted in the middle, was in a loose bun. 

As the clacking of her heels disappeared downstairs, Malcolm Longwater grumbled silently at himself, and at his overbearing helicopter parent mother.

“I’m 19! 19, for fucks sake. I’m an adult, not a child…” His mother had taken away his phone and shut off the internet to his room….again. Just a small oversight, and now the bins were full for the next week. 

And mom ended up overreacting as always. He had gotten used to it…but now he was getting tired of it. Sure, he lived in her home, but at the same time he wished for a more relaxed parent now that he was an adult.  But here he was again. No phone, no internet. 

Or so his mother thought. Malcolm lay down on his bed and reached to the side of it, pulling out a secret phone that his mother didn’t know about. Given to him by who else, his “bad influence” friend Warren. 

Or as he should call him now, Auntie Annie.

Three weeks ago life had changed for Malcolm when it turned out that Warren had successfully impersonated his auntie with the massive chest. He was making a good income from selling nudes of “herself” online. She’d even shown up to his house as her, charmed his parents and then secretly banged him upstairs. 

A small smile formed on his face. Good memories…sure, it was his aunt but…eh, the advantages of the situation were too much…including his Aunt dropping by when his parents were out for some private tutoring and getting much more than pocket money from his “Aunt” as well.

[Mom grounded me again, forgot to take out the bins, one week, gonna read some books]

[Would you like Auntie to come over and help?]

Warren had this odd preference to really get referred to as his aunt. He seemed to take a sense of joy in pretending as if the fake version of his aunt was actually real. It weirded Malcolm out, but the upsides were so great as to make that minor point near irrelevant. Auntie’s holes were real enough…and within reach. Malcolm gently rubbed his own crotch bulge as his thoughts turned sexual.

[Yes, if you can use some words to unground me that would be nice. Maybe some private time afterwards, ma said that she needed to do some shopping later]

[don’t worry dear, Auntie will fix all your problems. Be there in 30 minutes. I’ll make your mom much, much better]

Malcolm put the phone away and laid on his bed. If there was anything that Warren/Auntie was good at, it was talking. 

—————————

The doorbell rang and Margaret got up from reading her advice book on how to subjugate rebellious teens. She straightened out her dress and then walked up to the front door.

“Hey hey, Maggie”

“Annie!” 

The supreme milf that entered the room was unmistakable for her giant breasts that seemed to pop out of her light green dress no matter what she tried. So big things needed to be custom made for her. Annie with her raven haired bob cut entered the hall wearing a pair of sunglasses.

“What a surprise, you hadn’t called?”

“I never do , you know me. Just had this feeling I should come by and cheer you up.”

The two women hugged in an affectionate way as Margaret closed the door behind Annie.

“Come on in, have some tea with me.”

“Gladly, Maggie!”

Patiently, Annie sat down on the couch waiting for Margaret to prepare tea for the both of them. Then, a thought struck Warren for a moment.

“Where’s’ my favourite nephew?”

“He’s grounded. Forgot to take out the bins and now they’re overflowing. What a disaster that boy is, how is he ever going to live out on his own?”

“Ah…I see. Can I visit him?”

“Sure, talk some sense into the boy while the kettle is on. But otherwise, he needs to be alone to think about his massive mistakes.”

“Yeah…don’t worry, I’ll put him right.” Annie stepped up the stairs, her breasts and thick ass moving with every step in such a way as to put a smile on her face. She walked up to Malcolm’s room and knocked on the door.

She opened it and glanced at Malcolm. This woman in her mid 40’s dressed in a green dress, a true MILF queen leaned against the doorpost and with a smug smile said.

“Sup, fucker.”

“Ssssht, she could hear you!” Malcolm responded, being sure to not be as loud.

“Hear what? She’s busy making tea, and if she did hear it, she misheard me obviously. I am far too much of a refined woman to use such horrid words.” Annie closed the door behind him and sat down at the far end of the bed.

“I’m here to save you Malcolm. Dont worry after today your mother will be much less of a bitch. Trust me on that.”

“What…what are you going to do? This sounds like much more than words.”

“Do you trust me?”

Malcolm sighed. “Yes…yes I do.”

“Good. Stay here until I come to pick you up.” His aunt reached for his boxer shorts and groped Malcolm.

“No time for sex, but i did get a new upgrade installed on Auntie.” Her well manicured hands reached underneath her dress and lifted it up until her fat mounds spilled from underneath. Malcolm could barely hide how excited he was and he was getting hard quickly. 

“No time for the real thing…just suck on my nipple.” Malcolm put both hands on her left breast and eagerly suckled Annies thick nipple. He could feel something wet gather in his mouth before a sudden burst of fluid got him to pull back

Annie laughed. “How do you like my milk? Cumming and squirting from my tits at the same time is fantastic, you should try it once.”

Malcolm did swallow the milk even though he looked somewhat disgusted for a short moment.

“You’ll get used to it. Besides…i’m about to make your life a lot better too.” She lowered her dress once again and checked herself in a mirror.

“God I love being a MILF. See you in a bit Malcolm. Hour or two. Cheers.” She got up and gave him a polite nod. “When i’m done you won’t be grounded any more, trust me.”

Malcolm said nothing, wiping some of Annie’s milk off his face. This was…still something that he needed to get used to. But damn if it wasn’t sexy as all hell!

——–

“So the boy is a disaster…” Margaret handed a fresh cup of Ginseng tea to Annie. “Just…where have I gone wrong? I’ve been too loose on him and HUSBAND NAME is just…too soft. He needs rigid discipline and limitations.”

Annie nodded, silently mocking the stupid idiot of a mother that had such a high opion of herself.

“Yes but I think you might be a bit too hard on him.”

“No, Annie, I’m too soft. If I’m not there looking over that boy’s shoulder he’ll end up burning the house down.”

“Ah.”

“It wasn’t my fault the state of Malcolm it’s all his!”

“Who?”

“Warren, the nasty satanic drug dealer “friend “I’ve been trying to get the bastard arrested for crimes against humanity but…justice paid off.

Annie frowned, not wanting to let her real emotions come out too much.

“Paid off how.”

“That beast of a man disappeared a month ago. Hopefully he died of a drug overdose, one less demon on earth.”

Annie dropped her teacup and it shattered in a thousand pieces splattering tea all across the floor. She reached into her wallet while Margaret immediately started cleaning it up.

Annie hit play on the small MP3 player and slipped a headset on top of Margaret’s ears who was crouching before her. 

She bolted up and looked at Annie in confusion. “What..what is this???”

“The sun is going down, and down. It has almost set…and the sun is gone. Sleep.”

To Annie’s relief Margaret suddenly froze and her eyelids fell shut. Annie immediately pulled her sister-in law onto the couch, placing her so that her neck and head lay on her knees.

“Open your eyes.” Margaret complied, looking still quite confused while Annie turned up the hypnotic beats. “Follow the light.” She pulled out the flashlight hidden in her purse and started making repeated circles over Maragaret’s face while repeating the same few words over and over. “Accept the sunset…accept the sunset….accept your orders…” 

It took him half an hour for Warren to feel confident about his hypnosis before he snapped his fingers. Margaret arose from her stupor, yet didn’t react or say anything. Annie collected the headphones and MP3 players and put them back in her purse.

“Follow me.”

Without any objection or delay Margaret followed Annie out of the house, into her car, and sat in the driver’s seat motionlessly while Annie drove to Warren’s new apartment. 

“It’s such a disappointment. I was going to ease you into it, call it, a new way to destress and such, hypnosis for relaxation, but you had to insult me to my face. Fine enough, I’ll just stop playing and get right down to business, simple as.”

There was no response, and there would be none.

When they got to the parking floor beneath the apartment complex, Annie parked her car and guided Margaret to the elevator. One short trip later, and they were in Warren’s apartment. While on the outside it was nondescript, inside it was basically a porn studio with collections of sex toys on the wall and all sorts of camera equipment in organized racks.

“Welcome to your temporary home, Sierra Wayne…” Annie locked the door behind her.

“This is only day one, and there is a lot that you will need to learn. First…let’s get rid of that face of yours. Sit on that couch.” Margaret complied, sitting down on the couch while Annie walked towards her closet. In the middle of it lay a mess of red hair that when she lifted it up, turned out to be a mask of a woman. 

She was a MILF with her red hair running down to where her nipples would be, with expressive black eyeshadow around her eyes and bright red lips. A petite nose made her look rather cute, and her cheeks were naturally rosy.

Annie reached for the mask and straightened it out. From behind she walked up to Margaret and stretched the mask wide. Margaret completely ignored everything as her sister-in-law pressed the mask over her head, stretching its neck down to her own as the slightly thicker features of Sierra washed over Margaret’s. Her eye colour shifted to a light blue and the whole face readjusted itself into that of a porn star with just a bit too much makeup. 

With genuine concern Annie adjusted the long hair behind Margaret’s back and made sure the mask functioned properly with a few touches of the new face and checking the eye colour.

“Perfect.” 

“Undress.”

Margaret responded calmly, starting to take off her clothing as if she was alone. First, her blue dress followed by her underwear. When she was fully naked, she continued to sit there oblivious to the world.

“Baseline submissive…yes but no new personality…and more hooks…you will now respond to the name Sierra only.”

“Do you understand, Sierra?”

“Yes.”

“Good…” Annie put on the TV and put the mobile headphones on Sierra’s head.

“There is some food in the kitchen, and the toilet is to the right. If you need to eat or anything else you can do so. Once you are done, come back to the screen and keep these headphones on.”

Annie smiled as she started undressing herself. The oblivious Sierra sat there, silently staring at the screen as Annie freed her mounds by getting undressed. Like Margaret before she slipped out of her underwear and placed it in a neatly folded pile. Annie stood before Sierra and pressed her wet pussy lips against her face. “Oh yeah, how do you like that demon, you absolute bitch!” From within her folds, a sudden cock emerged pressing against Sierra’s face, sticking out not just with a shaft, but with balls as well. Annie however was satisfied with just rubbing her dick all over Sierra’s face, spreading a bit of cum all over before suddenly retracting her cock.

“There, you look like a good porn star already. Truth is…I was so prepared for being you, I just couldn’t wait.” Annie reached behind her head and tugged at a zipper that suddenly emerged on her back. As more and more of her skin came loose the giant chest sagged somewhat until the person underneath Annie slipped her arms out. It looked as if Annie was deflating until one of the arms reached for her face and pulled it forward. By the force of gravity itself the skin peeled off the skin of the white woman that had been hidden underneath the skin of Malcolm’s aunt. 

And underneath his aunt…was his mother. A perfect copy and recreation of Margaret Longwater smiled at the cum-coated porn star sitting lifeless on the couch.

“I will be a much better mom than you ever were, Margaret…” She began touching herself all over, cupping her breasts and starting to finger herself. “Soon, you won’t even remember who you were…only who you will be. And if I ever want…me back….you’ll just wake up and won’t remember a thing.”

“Oh, my clothes, how neat of you to leave them there.” Margaret started picking up the clothes that “she” had gotten out of just moments ago. First slipping into the fine silken underwear and hoisting her tits into the bra. Warren thought he’d want something new for a while now, to spice things up, and what could be spicier than improving his best friend’s life and at the same time getting back at the stuck up parents who seemed to care less for their son then he did.

Margaret finished by getting the lovely dress back on and fixing up her messy hair. “It’s a shame the hair never compresses well underneath the skinsuit.”

“Ah well…I’ll be back to continue your training tomorrow morning. Follow your orders, Sierra.”

“Yes…mistress.”

“Good.”

Margaret Longwater picked up her phone and wallet and checked it.

“What is Margaret’s pin code and password to her phone?”

“7599 and “butterfly” “

“Thanks, slut.”

————————————————————————————————

Margaret Longwater walked into her house, and stored her keys in the right place. She was carrying her purse and two shopping bags on both arms. Walking up the stairs, she moved past Malcolm’s room without opening his door. She walked into the master bedroom and opened the closet, digging deep into the back where she found some extra place that was quite out of sight. She placed both of the shopping bags in the back, covered with a few clothes. A quick peek inside revealed a wide array of sex toys and bondage things as well as plenty of lubricant and other kinky implements. But most notable on top was a big black strapon that appeared to be fully hollow on the inside. It even looked custom made to look like a regular strap on the outside. 

She checked the time. Not much more than an hour had passed since she had replaced Malcolm’s mother. A smile crept across her face.

“Time to mess with my mess-up of a son.”

She knocked on the door of Malcolm’s room and let herself in. Malcolm was lying down on his bed, reading some history book out of boredom.

‘Malcolm…we need to talk.”

Malcolm looked up at his mother, expecting his aunt to show up instead. 

“Yeah, where is Auntie Annie?”

“She left. But she’s been talking some sense into me and I want to put things right.”

“Malcolm…can I sit on the bed?”

“Yeah…yeah mom.” Malcolm sat on the edge of the bed while Margaret sat next to him.

“I just am very disappointed in you. Forgetting to take the bins out, it’s the start of something serious you know.”

“Look, Mom, I’m sorry for forgetting, I won’t do it again. But I’m 19 years old now, I can handle myself much more than you think I can.”

Margaret shook her head. “Annie argued as much, but she’s wrong. You’re just not ready for the world, son. Don’t worry, I’ll protect you.” She hugged him, well aware of the mixed feelings and frustration Malcolm was feeling but he didn’t want to set his mother off.

She held the hug for a moment before letting go.

“Please, mom, can you unground me, it was just the bins.”

“Yeah, look Malcolm…you need to learn your place. You are below me. I want you…below me.” Margaret leaned in with a smirk on her face . “I want you inside me.” 

Malcolm glanced in short confusion before his mother leaned in, wrapped both hands around his ass and leaned in for a passionate tongue kiss.

Malcolm was too stunned to respond, letting it happen as his mother plummeted onto him letting her breasts press against his body. 

He pulled away from the tongue kiss for a moment.

“WARREN! WHAT THE! HOW THE! MOM IS DOWNSTAIRS”

“No she’s not, I’m right here, idiot.” Margaret got off him and pulled her son upright.

“What…what did you do to my mother? How…how did you replace her.”

“First, you need to know something about your mother. She’s hot….and stupid” Margaret groped her own breasts.

“She was going on and on about how you were still a child and that she needed to go even further in tracing your steps and being an even worse helicopter parent. And she was going to if I had not stepped in.”

“First my aunt, then my mom.” 

“Malcolm.” She put her hands on her sides. “I’m being serious here, mate.”

“While being my mom.”

“Mmhm.”

“Okay, sure, Warren. She was going to make my life worse, you say.”

“Yeah. That bitch…me was going off the deep end. It’s just bins, mate, not the end of the world but she sure acted like it.”

“So…how did you become her? Where’s mom now?”

Margaret reached in her pocket and pulled out Warren’s phone. She pulled up a picture of a thicc redhead woman with cum on her face sitting lifelessly on a couch.

“Look at her proportions. That’s your man, being brainwashed into an obedient little porn star.”

“WHAT!”

“Oh, come on, I’ll pass any cash she makes directly to you. And, I’ll be a much better mother to you then she ever was.”

“What, but…she…her…mom…”

“Buddy, you know me. I’ve got your back, always have. Plus…i’ve been meaning to get back at your parents for shittalking me and mistreating you. Your mom is a bitch, and your dad is away so often it’s a joke. “

“But you can’t be my mother…”

“Yeah I can. Not forever, mind you, but hey, it’s going to be fun playing the housewife that fucks her son when her husband is away.”

“I…”

“Malcolm..come on. Free cash, free sex, and your best friend within arms reach. What more could a guy want?” Margaret, the stuck-up housewife, started to pull off her dress. With a quick slip of her hands behind her back, she liberated her tits from her bra. Malcolm continued to sit there pretty much motionless.

Margaret saw it, and immediately reversed course, covering himself up again, and then getting back in her dress. It was clear that her son was in no mood for sex with his mom..so far.

“Aight, if you don’t want to that’s fine. I just am going to play your mom for a bit nevertheles..”

“This is…pretty intense.”

“Oh, heres your phone back.” Mom handed him his phone. “Already reconnected your internet. So i wanted to say, how about I get you a beer and we play some Street Fighter?”

“A beer…but I’m…”

“With a much better mother. Do you want a beer or not?”

“Yeah, please Warren.”

“Call me mom, please.”

“Warren, this is…”

“Call me mom. Or mother. Or ma. Please.”

Malcolm shook his head.

“Okay. Just don’t call me Warren in front of your dad, that will be on you. Let me get us a fresh sixpack, my husband isn’t due to be home for a few hours.”

“Is…is it really you? Is this…really happening?”

“Would your mother, your actual mother, actually be this kind to you? And offer you a “very dangerous” beer and play street fighter with you? And by the way, the offer to fuck me, dude, is still on the table whenever you’re ready for it.”

Malcolm sat ther, silently and started up his PS4. His mind was absent, lost in thought until his mother came in with a pack of beer and a few bags of chips.

“Here man.” She touched her son on the shoulder. “Are you okay?”

“You…you replaced my mom and turned her into a porn star.”

“Yep. You know why I did that?”

“Cuz you wanted to get back at my parents for constantly shittalking you.”

“Partially. Partially cuz your mom is very fuckable…and hot.” Margaret opened a beer can and chugged it down just like warren would in one go.

“But mainly because i was sick of your mother being such a bitch to you. And I thought it would be fun…and kinky.”

“Aha.” There was not much of a response and Warren didn’t want to push it

 so in fact the both of them focussed on the game.

“Just because I’m your mom doesn’t mean I’ll go easy on you.”

“Best out of five?”

“As always, bro.”

——–

“Oh come on!” Margaret put the controller down. She’d lost, 4-1. “These fucking tits dont help me when they bounce around when im gaming.”

“Sure blame your poor air control on your titties.”

“Oh shut up Malcolm I’ll kick your ass next time.” His mother bantered back.

with him as she dug her fingers in the bag of chips to grab the last few out of it. 

Malcolm put the controller away and switched off the TV. He glanced at his mother, doing things his mother would never do…and berate him for if he did it.

There were upsides to this madness. 

“So…tell me about hypnosis.”

“It’s a process that requires a simple setup of relaxation before slowly reaffirming them into a submissive stance where they can be slowly molded into believing different things. Your mom right now is being bombarded with sounds and images of her being a successful solo porn star, and tomorrow I’ll release Sierra Wayne onto the internet. “

“Please don’t do that to me.”

His mother looked pissed and glared at him. “Bruh” Margaret shook her head. “This whole thing…well, most of it has been about helping you, man. Yes, I could in a moment of weakness hypnotize you and brainwash you into anything I’d like, but what would be the point. I like you, man.”

“So…how long are you going to be like this for?”

“Dunno. I can bring your mom back from Sierra any time I want and just place her back without even knowing she ever left. But…well, first I’d want to get at your dad.”

“Are you going to…brainwash dad too?’

“Nah, nah. That’d be too easy. What I want to do is have him suck my cock and then get pegged by his wife instead. I got this strap-on that slides over my own.”

“Ah…I see.” Malcolm was quiet for a bit, reevaluating things. His parents had been fine before but now that he was getting older he could see that both of them weren’t as great as he thought they were. For now, he’d let it all slide and just enjoy the perks of his new mother, while keeping Warren on a positive track hopefully. And then…you know while Malcolm was never that much into his mother at all, this…was not his mother. 

And Warren as Annie was one hell of an amazing fuck as well…so what about his mother?

“Okay, I’ll go with this, Warren. I mean, mom.”

“Thanks. If you really were opposed to this all I would’ve just undone it i guess.”

“So…you’re mom now, and annie…is there any other family member I need to know about?”

“These suits are pricey, custom made. It takes me time to get new forms. Sierra Wayne was just the mask of a redheaded MILF which cut it in price, but all i’ve got is Annie, your mom, and there was this male costume I’d bought on a giggle.”

“A male costume?”

‘Yeah, of this burly bearded guy, the kind of alpha male they make jokes on the internet about. It’s quite fun having big muscles and a bigger dick, gets you a lot of looks.”

“Burly bearded guy…” Malcolm touched his chin, thinking.

“Wait…that sounds like that guy that hit on me aggressively while I was shopping last week!”

Malcolm glared, and Margaret turned away while giggling.

“Warren”

“God, look on your face! The look!” Margaret doubled over in laughter. “You got so shy and red, it was hilarious.”

“You motherfucker!”

“Oh no, not me, soon that’ll be you. You fucked your aunt first, and I don’t think you’ll be able to resist mommys charms for long.” Margaret groped herself and let out an erotic moan to which Malcolm blushed.

“But, man, I can wait. No need to hurry, I can take my time. Is your dad coming home tonight?”

“No, he said he was out today for work.”

“You think he’s cheating on her? I mean, me?”

“I don’t know.”

“…want to find out?”

Malcolm shook his head. “That would just…split our family apart.”

“To be fair, I could also be your mommy forever….”

Malcolm glanced at her. “That’s insane.”

“Mmhm. But no one will go looking for Maragaret if she’s never gone missing.” His mother leaned over to him pressing her tits against her son. “And, most importantly, we can have time for lots of family bonding as well.” Malcolm was blushing as well and getting hard.

“I…eh…oh god please help me im so hard.”

“Let your mother take care of that.” Margaret freed her son’s rock hard cock from his pants and let her tongue run beside it with a smile on her face.

“So…so…Warren, how long have you been into me?”

“First of all, I don’t ever want you mentioning that evil satanist in my house again!” The tone was the exact same as when his mother was ranting over whatever had slighted her but the look in her eyes was filled with love.

“Secondly, mommy has been wanting you for three years. But it was a shame that you’re not into guys so I had to find a different way.”

“By being my family members?”

“That is just how it happened.” Margaret deepthroated her son in one go. “Had to get rid of the real me to make your life better. Plus…it’s so hot to be secretly super kinky while being the perfect housewife on the outside. Your father will never even know, it will be our secret.”

“I…eh…oh…” Malcolm fell back into his bed and just let it happen to him while his mother worked his cock like her life depended on it. 

“Nothing gets me worked on then this kind of crazy taboo. I want to fuck you when your father his home and then turn around and be his perfect wife, never knowing his wife isn’t real at all!” With like a maddened forceful rip she pulled off her dress, ruining it in the process. She got completely naked after ripping off her panties and bra as well, towering over Malcolm.

“What are you doing, mom?’’

She leaned over him and rubbed her dripping wet pussy against his rock hard dick, sliding onto his dick.

“Oh..ff..f.f..fUCK! Mom!” 

“Yes, that’s what you’re doing right now.” Her F cup breasts bounced all over the place while the look on her face was one of great excitement and joy. Malcolm was pinned in place while his mother continued to slide up and down his length without even a second of pausing.

“Warren…mom…warren…”

“Just call me mom, or mommy, or Margaret…I’ll be your mother until lI get bored, and who knows when that will be.” Her hair was going all over the place, wild as the fake mother rode her son.

“You can’t…you can’t just be…her forever!”

“And I won’t, trust me. Just…in the meantime.” Margaret was relentless, never once stopping the pace before Malcolm began twitching slightly.

“Mom…I…” 

“Breed me, give yourself another sibling! Do it, love!”

He couldn’t hold it in, and blasted his load right in his mothers pussy. Both of them screamed, sweat pouring all over as Malcolm unleashed into his mother load after load of cum. Margaret toppled over, falling onto him, laughing and shouting “YES! YES! YES!” over and over. She immediately began kissing and hugging Maclolm as they became entwined together in his bed.

Slowly but surely the two of them calmed down, Margaret’s hair and makeup in ruins while Malcolm looked exhausted.

“I need…I need to take a rest now…this is so much, i need to process this.”

His mother smiled warmly at him and kissed him on the cheek. “Get some rest…I’ll keep you close…” 

Margaret started to hum a subtle tune and kissed him on the cheek. “See you in the morning, bro.”

Malcolm didn’t respond, overwhelmed by everything as he closed his eyes and drifted off in the warmth radiating from the presence of his mother. His dick was still packed inside her, and she wouldn’t want it any other way