Auntie Annie

(a bit of a retread from Forbidden Fruit, but it was too fun to pass up.)

“Sister!” “What a surprise!” Ian Longwater stepped from his front door to hug his sister from out of town. It’s been two months since my brother and sister had seen each other for three months. Whereas Ian couldn’t have looked more generic middle aged dad with a moustache, Annie definitely stood out.

While in her mid 40’s Annie looked spectacular. Raven hair with motherly thick hips and her imposing chest that was a massive H cup draped into a lovely black dress. A face with her light blue eyes with deep dark eyeliner all around and her bobcut of raven black hair contrasting her white t-shirt and blouse combo. She was wearing high heels and a navy blue skirt

“What a surprise Annie! You didn’t call ahead!” 

“Yeah, i was in the neighbourhood and misplaced both my phone and wallet. Could I crash at your place for a bit?”

“Of course, of course!”

“Margaret! My sister is here! Best prepare one extra for dinner! Come in, sister.”

“I’d love to.” Annie smiled widely. “Where’s Malcolm?”

“Malcolm!” The voice reverberated  through the house as Ian turned to the stairs. Malcolm, his only child walked downstairs. 

Malcolm was in many ways a redux of his father, just younger with a buzzcut and a boring t-shirt and pants combo. In fact, the best way to describe the young adult would be flat out “boring”. It was his personality that made it work, one of the nicest people that you’ve ever met.

Malcolm held out his hand but his aunt just smothered him in a hug pressing her boobs against him. “Oh, okay, good seeing you too Aunt Annie.”

“I was in the neighbourhood, so I thought I’d come just for you!”

“Dinner is ready!” Margaret Triton-Longwater turned around the corner with her red hairs running down her face and an apron as well. 

“We’ve got meatloaf tonight, Annie.”

“Great.” Annie let go of Malcolm and joined the other three in the kitchen. They spent quite some time catching up on things when the conversation halfway through turned to Malcolm. He was busy chowing down when Annie turned to him and smiled. 

“So Malcolm, how have you been? You haven’t talked much yet.”

“Been good. Grades are good and I’ve started to read more books outside of school mandated ones, and dad and I have been building a new shed.”

“His hammer strikes are a bit off, but he’s definitely got the spirit of hitting nails. But…”

Malcolm glanced at his father. “Only thing is that he needs to find better friends.”

“Excuse me?”

“Oh come on, dad, not this conversation again.”

“Warren is just a scummy guy, Malcolm. He probably deals drugs, being arrested multiple times for pulling scams. Why would you keep hanging out with someone like that?”

Malcolm increased his pace of eating, preferring to now get dinner over with then listen to another lecture.

“He has always been good to me, ma.” 

“One day he’ll be so good to you that he ends up ruining your credit score and life by taking advantage of you.”

“It’s not like that. Yes, he is shady, yes, he is…not normal, but he is a real friend, has been so for years.

“Tell me about this Warren, Malcolm.”

“He’s a guy that I’ve known since I was 10. He dropped out of school years ago and now he just gets by. But every time i meet him, it’s great!”

“Malcolm, you need to understand that he is a bad influence on you. He has no real income, no home, he’s just some…drifter you used to know. You need to look ahead, not behind.” 

Malcolm finished off his dinner and left the table.

“Okay, so this Warren is a bad influence on him. Hopefully, he sees that before he gets burned. And else…well he gets burnt and learns a lesson not to trust random vagabonds.”

Annie glanced for a second before forcing a smile on her face. “You know what, you two are pretty close to Malcolm. I’m pretty sure I, cool aunt Annie can maybe get some words in. Won’t guarantee that it will work but I can try at least.”

“Please. Malcolm is a good kid in general. I just…you hate to see a toxic influence on your kid.”

Annie got up with such speed that her breasts jiggled slightly as she moved up the stairs. A sly smile crept across her face once her back was turned. Yet as Annie opened the door and stepped in, she just had the big smile on her face.

“Hey cousin.”

“Hey aunt Annie. I don’t…I don’t need more lectures from you, please. Warren is…”

“Yes yes, I know. Don’t worry too much about it. Let’s play some games instead.”

“I thought you hated video games.” Malcolm raised a confused eyebrow.

“Yes, but one has to adapt to the times they live in. Come on, let’s play some Smashing…bruhs.” She lifted up the switch and handed it to him. “Please turn on the game, I don’t know how.”

Malcolm got to starting up the game while Annie glanced at him doing it.

“Oh, the button is there!”

“Yes, let me show you how the game works.” For the next 30 minutes, Malcolm patiently explained to his aunt how the game worked as she stumbled about.

“Okay, let’s do a practice match! I’ll take this guy, he’s a doctor!” Annie picked doctor Mario while Malcolm went for King K Rool. As the match started, his aunt started glaring differently. She looked very focussed and on point.

Malcolm went easy on her, starting to just jab at her. Awkwardly, Annie dodged a few times by jumping and then suddenly turned into a flurry of attacks that smashed Malcom’s character off the stage within 20 seconds.

“I…how..did you.”  Annie smiled. “I didn’t know you played smash brothers.”

“Been practicing with you for years.” Malcolm glanced at her as his eyes went wide in absurd shock. His cool aunt had put down the controller and reached for her blouse, unbuttoning it and showing her massive mounds to him. “Not bad, these tits, for the guy who’s been supplying you with beer since you were 16.”

“w….w…Warren! What, what, only Warren knows about that.” Annie reached under her chin and stretched the skin.

“I’m your sexy aunt now, buddy.” Warren’s voice spoke before Annie let the skin snap back.

“What? How? How?”  

“Do you like your aunt’s tits? I do, been groping them all day.” She groped her breasts with a perverted smile. 

“H….-how?”

Annie could hear someone walking on the stairs and quickly fixed up her blouse. Malcolm was frozen in place, his jaw agape.

Ian entered the room.

“D-dad. She…he…”

“Malcolm, I get that you don’t want to hear our lectures but I don’t want you storming off from the table again. Okay, son? You want to watch a movie later by the way. Killer Nights 2 is on in an hour.”

“I’m making progress with him. Might take all night, but it looks like you don’t have to hear about Warren again. Just give us some time.”

“Ah, okay. The bed in the guest room is ready for you.”

“Thank you brother, i’ll see you later. After i’m done here I’m heading to bed.”

“Night!” Ian turned around and left the two of them alone.

“What have you done with my aunt, Warren?”

“A new kind of identity theft.” Annie quipped. 

“No, you are totally her. Voice and body.”

“Mmhm. I’m fully functional, from top to…bottom.”

“But why my aunt? Why pretend to be her, hold on, what did you do to her?”

“The real Annie is back home where she belongs. It took me some time to get visual and vocal references and of course pool my cash to get this. More specifically, these.”

Annie looked at him with a motherly glance which quickly turned into a perverted smile as she liberated her breasts once again.  It was…very wrong to Malcolm but at the same time incredibly hot. 

“You didn’t answer me. Why my aunt?”

Annie turned to face him.

“Women have it easy nowadays. Need cash? Just open up an Just.” Annie pulled up a webpage showing her page of his aunt doing lewd pictures. On the side there was a message with 4000 dollars per month next to the picture of his aunt

“Of all the people I know your aunt is the hottest yet least protected. Especially these megatits are hard to come by. Naturally grown even…but I digress. Being your super sexy milfy aunt gives me more cash than anyone could ever imagine. And it was in the end, not hard to do this.

“You made porn of my aunt?!?”

“Am still making it, but it’s under an alias “Milfstress Milk” “

“Oh God, what if it gets found out?”

“Meh, so she makes porn who cares.” Annie smiled at the view of Malcolm glancing at her tits before turning away.

“It will ruin her reputation! Do you not realize how this affects her life?”

“It won’t ruin Annie. She’s a lone housewife collecting alimony and raising her kids. Who cares she makes some fat stacks with her fat breasts?”

“It will! Just…man, this is messed up.”

“Allright, okay. You know, I can just get myself a new face. Will take me some time to do. But once I look different face wise, no one’s affected.”

“That’s good, thank you.”

“You’re welcome. Just need to get myself a new ID then, I guess.”

“What do you mean ID?”

Annie reached in her purse and reached out her wallet. She handed him an ID card of one “Nikki Waterlong” with Annie’s face attached. “Go check it, it’s real. I even pay taxes on my porn.”

“Damn…damn…that’s…impressive.”

“You won’t be seeing Warren ever again…but you will be seeing a lot of your aunt.” She slipped out of her blouse and lowered out of her skirt, revealing her soaked panties.

“Warren…what are you doing?”

“At first…I thought it was just the suit. But now I realize, I just get off on the whole pretense. Downstairs, your dad thinks his sister is helping you come to terms about the evil influence of Warren. And surely enough it worked. But in the mean time, you and me are actually fucking like rabbits, right under his nose. God, that makes me wet.” 

Annie’s perky nipples were hard now, pushing forward quite a bit.

“What makes you think I want to have sex with my own fake aunt?”

“You’re hard right now, cousin. Your body doesn’t lie.” Malcolm grumbled for a moment, before nodding.

“Okay, I’m in.”

“Undress.”

Faster then he’d ever done so in his entire life, Malcolm got naked. He tossed off his shirt and freed his hard erection.

“I shouldn’t do this…” 

“But you want to.”

Standing before Malcolm was his aunt like he’d never seen her before. Sexy, teasing, and completely naked with her extreme cleavage right in front of him. She was dripping quite a bit, her bush being extremely hairy. 

“Go on, you can touch it all.”

Malcolm walked forward and pressed his head in between her cleavage. Instantly Annie wrapped her arms around him and pulled him close.

“Now we can be friends with benefits. Oh, I mean, family with benefits.”

“Damn..this is amazing how soft they are.”

“I know. First day I got her I did nothing but grope myself…while taking photos of course! Come to your auntie Annie.” She reached down to readjust his cock and press the tip against her pussy.

‘Oh..wow…yeah.”

“Stick it in me, nephew. Time for some of Auntie’s sex ed.” Malcolm did one thrust into his aunt’s nethers and let out a sight of deep satisfaction. 

“God your pussy is so tight Warren!”

“Warren? Please don’t mention that criminal again, he is a bad influence on you! Call me auntie, as you do normally.”

“Okay, sure. I guess.”

Malcolm had both hands wrapped around her as he pounded his aunt with a big smile on his face buried in between her chest.

Annie let out a giggle. “Okay, nephew, now let’s switch holes.” She pushed him back and crawled onto his bed giving him a good lookass. He could see something stuck in another sphincter, something black. She reached behind and slowly pulled out a thick dildo from her ass. 

“Now let’s try to prevent me from making more noise eh?” She held the dildo above her mouth as if it was a vine of grapes, then slid it inside, effortlessly deepthroating it till only the black latex balls were outside. She used one finger to pull her lips wider and pressed even those inside. Then she closed her lips and smiled at him. Malcolm could see that her face looked bloated and the dick shaped bulge going down her neck was clearly visible. Yet Annie breathed normally and with a big smile on her face motioned Malcolm to enter her.

She lay on her back, spread her legs wide and with one hand motioned towards her gaping anus.

Malcolm climbed up on the bed and positioned himself in between her legs. She suddenly swung both legs up and on top of his shoulders so that her anus was pressing against Malcolm’s rock hard erection. As he slid into his fake aunt,  a muffled moan could be heard. Annie’s fat mounds shifted with every wet, deep thrust of her nephew. She started groping herself and playing with her own perky nipples. 

Malcolm thrusted harder and harder wrapping right hand around Annies right leg while the other had free access to start to finger her.

His aunt looked him right in the eye. One of her hands formed a circle while the other pushed a fist through it.

“What? You serious? You want me to fist you?”

She nodded and made the same motion again.

“Okay…okay sure. Tell me if it is too much, please.”

Annie nodded. A bit unsure, Malcolm formed one fist and pressed it against his aunt’s dripping wet pussy. As he pushed gently the extreme self lubrication let his first slip in easily. It was a bit awkward at first  but eventually Malcolm found a decent pace alternating between fucking her ass and fisting her pussy alternatively. 

Not more than a minute in, Annie’s eyes rolled around wildly as Malcolm could feel her inner folds contract around his submerged arm as she leaked all over. Annie herself went fully limp, an extremely loud moan of sexual release becoming merely a whimper because of her mouthful of dildo.

She just lay there as Malcolm increased his pace, not wanting to be left behind. His aunts sphincter was even tighter than before as Maxwell shot his load up her ass, eliciting another moan from his aunt. He was sweating, panting, and moaning as quietly as possible as he continued to fill her up. Finally, he pulled out, his cock (and her ass) dripping with his cum. 

Annie slowly got up, pushing under her chin as she got the dildo to exit her mouth with a comical flop on her belly. She lifted it up and plugged her ass once again.

“Wouldn’t you want to clean it up?”

“No, no. Having a big dildo in my ass with your cum sloshing around in it is super hot, nephew. At least, while I’m pretending to be your aunt. ” Annie got up and started to get dressed. Before she put her blouse back on she turned around and offered her breasts to him.

“Go on, grope them before we go back to pretending. This is a thank you for the amazing sex.”

Malcolm walked forward and groped his aunt’s tits. 

“Is this even real?”

“Hold on.” Annie reached for her face and tugged her lips in both directions. They gave way, suddenly revealing the iconic 5 o’clock shadow that warren had. Malcolm could only see his chin and lips, while otherwise Warren was 100 percent his hot MILF aunt Annie. As Annie let go, her lips moved back in place.

“Besides, unlike all of my internet fans, you’re the only one whom gets to be with me for free.”

“Why am I the exception?”

“Because you’re my friend. Always have been.”

“Yeah, thanks.” 

‘Come on, go touch my boobs before we go downstairs.” Malcolm leaned in and rather than touch her nipples he sucked on one of them. He suddenly noticed milk streaming into his mouth, sucking it up. He looked up in confusion.

“Oh yeah, I can milk on command. Helps me with my mommy milkers roleplay vids. Aight, get dressed nephew. Now let’s slip back into our characters, and make sure that you never hang out with Warren again. She covered herself up, checking in the mirror. Once Malcolm was dressed, they both headed downstairs.

“So how long are you staying over, aunt Annie?”

“I won’t stay long, I don’t want to get found out, but you can visit your aunt any time at Warren’s place. For some…sex ed.” She giggled as she groped his crotch slightly. 

Malcolm looked up with an uncomfortable smile at his super sexy aunt and his best friend hidden inside her. It’d take some getting used to, but the positives outweigh the negatives by far. He couldn’t stop Warren, but perhaps, as usual, he could at least steer his best friend, now with benefits