Rotten to the Core

Story Info
His little sister is a little shit and rotten to the core.
14.9k words
4.19
71.9k
90
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Lost Boy
Lost Boy
5,759 Followers

All characters are 18 years old or older. Another one-shot story that has languished in the ether. I hope you like it. It is a story of desire, corruption, and darkness, mainly darkness. Feel free to comment, vote, and take comfort that the things in the light are there in the shadows, or are they?

*****

Sleep Deprivation:

The sounds drifted through the walls from my sister's bedroom. It was those noises that woke me. I reached out and picked up my watch from the nightstand. I cursed when I saw what time it was. She was really going for broke. I could hear it in her voice. She rarely got this excited. That is when I heard the second male voice. Seriously, she was taking on two guys at once. I guess that is why her friends called her Sindy the Slut. My sister exalted in her sexuality and how many guys she had taken to her bed. If my parents ever learned the truth about her promiscuity they'd lose their minds.

"I'm in..." groaned the first male voice.

"Hold her still," said the second. So, she was into threesomes now.

"She keeps wiggling," replied the first.

"Damn it, I am trying to get it in her ass." Snarled the second.

"I told you I don't do anal! Now cut it the fuck out!" Sindy argued. "Hey, I am going to scream and wake up my brother. Stop now!"

I was up and grabbing my aluminum baseball bat. I pushed open her door quietly to assess the situation before I drew attention to myself. The short thin guy was beneath my sister. Sindy was on top of him facing him. The second guy was much larger than his buddy and he kept trying to press the head of his cock against Sindy's wiggling ass. The heavier set guy had an expression I didn't like at all. He wanted to violate her in the worst way.

"Um Tom," the little guy was stammering when he spotted me.

"What is it?" He growled as he looked over his shoulder. "Aw shit!"

"Out... NOW!"

They rushed to leave before I imparted some primal punishment. I set the bat down and handed my sister the robe on her bed. She ignored it and hugged me instead. She made a habit of pressing her bare tits against my chest. I was torn between her tits or her ass as her best feature. She was cute the way next door neighbor girls are supposed to be. Sis followed our mother with her jet-black hair and deep blue eyes. She also had mom's large tits, that were big, firm, and perky. Her ass was glorious. I was an ass man and I won't lie, Sindy had an epic butt on her. The shape, fullness, and firmness were perfection itself.

"You saved me, again."

"You took on two guys in the house without warning me." I snapped at her. "I ought to..."

"What? Spank my ass, do you want to spank me Sam?"

I drug her over to the bed, sat down, and put her over my lap. She pretended to fight me until the first swat landed. Sindy moaned as I spanked her. I stopped when she climaxed, and her body shook. I held her until she recovered, and I lifted my damp hand up for her inspection.

"I always gush when you spank me." She moaned. "Are you going to fuck me Sam?"

"Should I?" I asked raising an eyebrow. "That wouldn't be much of a punishment."

"If you don't you will only be punishing yourself. No one fucks my ass like you do." She purred and then gasped. "Your cock is pressing against my belly."

"Can you blame me," I told her as I eased two fingers into her snug little pussy. "Soaked like the dirty little slut you are."

"MMMMM nobody touches me the way you do," Sindy purred. "Even your fingers are longer and thicker than other guys. You stir up my insides and drive me crazy."

"You need to slow down Sindy," I told her as I took my fingers slick with her juices and worked them into her ass. What if I hadn't been here?"

"They'd have raped my ass," she said matter of factly. "I am sure they would have taken turns plowing both my holes. I love being DP'd. Ooh, your cock is getting harder! Are you going to punish me with it?" She asked as I began thrusting my fingers. "What else can I do to piss you off? I love your angry side."

"You want us to be exclusive?" I asked as I ground my digits deep in her butt.

"I promised not to let anyone, but you stick their dick in my ass. You know how much I love doing anal... so... what do you think Sherlock?"

"You are going to college soon," I frowned as I withdrew my fingers and positioned her in my lap. "As much as I would love to service you and your deliciously tight holes, it would eventually come to an end."

"I understand," she grunted as the head of my cock entered her ass. "Can I ask you a strange question Sam?"

"You better expect an odd reply." I told her. "Ask away."

"If you could have anything, or in this case give someone anything they wanted what would you be willing to do for it?" She moaned as my cock sank all the way in.

"Anything huh? There is a limit to what I would be willing to do. Answer enough?"

"Uh huh," she replied as she began shoving her hips backward.

"Besides, you adore being DP'd and I hate sharing you..." I moaned as the shaft of my cock sank deep into her backside. "I never get tired of your ass."

"You spoil me so much," Sindy groaned. "It is about time I spoiled you."

"You do," I cried out as she began riding me. "It isn't like I can be in two places at the same time."

"UNNN... UNNNNNN... UNNNNNNNNNNN... so good..." Sis grunted as she fucked me. "But what if you could?"

"Wait... what?"

Flashback: Six Months Ago

"...Happy Birthday to you!" We all sang to her.

Sindy blushed furiously. We had surprised her when she came home from school. My dad, the world class lawyer, was here for once. But then again how often does your daughter turn eighteen? Mom, the homicide detective, was also home for once. She worked so many strange hours especially when she was on call. My sister and I were both very independent by nature and nurture. I had practically raised my sister on my own. The last ten years since mom made the rank of detective had been rough on me but I didn't mind. Sindy and I had grown up close, too close. I had bought her first tampons for her. I had helped her shop for her first bra and all those that followed. I knew her breasts as well as she did. I had even gone to her doctor's appointment recently to get her birth control. I had driven her there. Mom had begged me to get her on it before she was legal. Mom had seen certain signs in her daughter that she recognized. I had even asked her about it.

"Why are you so determined to get Sindy on birth control?"

"I... damn it Sam just do it!" Mom growled back.

"I understand." I replied grinning.

"Why the hell are you smiling?"

"You were a dirty little slut and you see that she is just like you." I said waiting for the slap to follow but it didn't.

"I won't argue with you." She murmured looking at her feet. "I liked sex a lot. Your sister masturbates like a fiend. If she gets a whiff of a guy she gets wet."

"I'll take care of it, the birth control I mean." I said surrendering. "What was that look?"

"Nothing." She growled and walked away.

That was weeks ago, and I was still pondering Mom's strange behavior. I ate my cake and watched my family. Dad ate his cake, but it was clear his mind was elsewhere. He was working on yet another high profile legal case. Mom on the other hand looked oddly distracted. Her left hand was trembling as it lifted the forkful of cake to her mouth. She moaned as she chewed. Sindy was oblivious and looking at her gifts as she munched on chocolate cake. What was going on? Her cake half eaten she muttered something and fled the kitchen. Dad hardly even noticed. Sindy turned on the television while I followed my mom. She went upstairs to the bedroom she and my dad shared. I could tell she was in the master bathroom by the echo of her voice.

"So good..." she moaned. "You are a dirty little slut."

I peered into the bathroom and clamped a hand over my mouth. Mom was withdrawing a vibrator from her pussy. She was bent over, and the toy was soaked. She licked the suction cup of a second toy and slapped it onto the lid of the toilet. I watched as she took off her skirt and I saw her pussy for the first time. Mom shaved her pussy! She used one hand to aim the bright blue toy as she lowered her body onto it. It sank inside of her easily. I took out my cock and began stroking it as she rode the toy.

"Fuck me..." she murmured. "I am your dirty little slut..." She whimpered but I missed the name she had whispered.

It wasn't my dad's name. Was she having an affair? It was wrong but damn my cock was so hard I had to do something. My hand moved at the same pace as her hips. I imagined that it was me sitting on the toilet and her soaked pussy wrapped around me. A part of me wanted to walk in. Mom's voice got louder, and I almost caught the name of her lover as she climaxed. Her shout drowned out my own. My load blasted the threshold of the open doorway. Aw shit, it wasn't until I had come to my senses that I realized I had left an obvious sign of my spying. I tucked my cock away and zipped up. She was already standing up and reaching for her skirt. I left her there.

I returned to the kitchen. Dad was sitting next to Sindy on the couch. I grabbed the gifts and carried them over. I set them on the coffee table and sat on the floor next to it. Mom appeared a minute or so later. She was smiling and plopped down next to sis on the couch. Mom apologized about the delay. She had a small mess in the bathroom she had, had to clean up. My heart sank, and I couldn't maintain eye contact.

"Can I open my gifts now?" Sindy asked.

"Of course, you can," Dad said his attention in the here and now for the moment.

"Let's see what you got." Mom purred.

Sis grabbed my gift and tore off the wrapping paper. She stared at the monochromatically painted box beneath. She turned it over in her hands and examined it. Sindy pushed down on the lid and applied sideward pressure sliding the panel out of its slotted channel. She cried out as she reached in and removed the hand carved penguin. Sindy loved penguins. I had made the box as well as carved the penguin. It was a hobby of mine.

"It is gorgeous!" Sindy screeched in joy.

"That is your best one yet son," Dad remarked. "You really have a talent."

"I agree, he is great with his hands." Mom commented as she uncrossed her legs giving me a glimpse under her skirt.

"I do my best." I said swallowing hard after seeing her pussy for the second time.

Sindy opened mom's gift next. It was a certificate for a yoga class that sis had been wanting to take for a while now. Dad handed Sindy the small box and we all knew what was inside of it. Sindy made a show of slowly tugging the ribbon from the box and opening it. The car keys inside rattled as sis plucked them from their velvet base. She hugged dad and then mom. We went out to the garage where dad had stealthily parked the convertible. It was six years old, but sis understood it was her first car and he wanted her to work her way up to a nicer one. She was bound to put a few dents and dings into it within a year.

We retired to the kitchen and the booze was broken out. Dad had a single glass before he kissed sis on the forehead and headed off to bed. Sindy was allowed a few sips of wine. The awkward energy in the air between mom and me was growing as the evening went on. To my surprise mom hugged me and sis and went off to bed an hour after dad had. I finished the bottle of wine that mom had opened. I helped Sindy finish her homework.

"Sam." Sis uttered my name and I knew by the way she said it that I was going to regret what followed. "What's a swinger?"

"Where the hell did you hear that?" I blurted out.

"I overheard dad on the phone talking to someone. He said that he and mom were swingers."

"Really? Well um... it means they have an open marriage." I began, and sis leaned closer. "Normally husbands only sleep with their wives. Swingers go to parties and they swap partners."

"Whoa, dad is okay with other guys fucking mom!" She giggled. "I can see why. She is like smoking hot. I want to grow up and look like her."

"Sweetie, you already have." I said before I could think that through.

"You think I'm fuckable?" She asked, and I stammered into silence. "Oh my god, you do, you want to fuck me! My brother is a total perv."

"Wait. Hold on! Jeez Sindy! Yes, you are attractive, but... but we are siblings. We can't and will not do the nasty. Got it?"

"I'll suck your dick." She purred and then busted out laughing. "Guys are all the same, always thinking with their dicks."

"You are going to grow up and make a fine sadist." I growled, and she laughed harder until she asked me what a sadist was.

"What is the opposite? I mean, what kind of girl likes being told what to do? I mean, she doesn't like being hurt but ordered around. You know what I mean?"

"A Sub or submissive," I growled as I got up and grabbed a beer from the fridge.

"You got a total boner," Sindy said pointing at my crotch. "I got you hard? You really are a perv."

"We are talking about sex, of course I got an erection. Are you a Sub?" I asked the volume leaving my voice.

"I think so. I am still a virgin. But, since you are hard as steel I can admit I am soaked. We are both pervs I guess. The thought of being told what to do gets me all tingly, even my nipples are poking out. Wanna see?"

"NO... I mean no. That is a slippery slope."

"Oh, you are worried that if I flashed my tits we'd end up fucking. Mom would kill us if we got caught doing the nasty."

"Sindy, it is wrong for brothers and sisters to fuck." I said the word fuck with way too much emphasis. "How much work do you have left?"

"Two more math problems and I am done."

"Let's knock them out and you go to your room. You are dangerous."

Sis laughed and a few minutes later she was putting her books away and heading off to bed. I was alone on the couch opening my second beer. I was drunk. The wine had done its work and the beer kept my buzz going. I heard the distant clunk as sis' door closed. I let out a sigh and turned on the television. I flipped through the channels and came across the new station my friends had been talking about. I turned down the volume as the music video began playing. I liked MTV and enjoyed the girls and their sexy outfits. The urge grew and soon I was ignoring the music. My erection needed attention. I slipped off my tennis shoes and crept silently upstairs. My parent's bedroom door was cracked open. That was odd, it was usually closed. I moved down the hall to sis' room and listened in at her door. There was no light coming from beneath the door and it was silent as the grave as well. I returned to my parent's room and pushed open the door.

My heart was pounding in my ears as I slipped into their room. Dad slept on the far side of the bed. Mom was on her side facing the door. She had stripped down to a translucent aquamarine negligee. I could see her dark areolae pressing against the material. My hand moved on its own and freed my cock. Precum was oozing from the tip and I walked over and took it in hand and painted her lips with the milky fluid. She moaned in her sleep and licked her lips. I almost busted a nut right then and there. I pressed the tip against her mouth a second time. This time the entire tip slid between her lips.

"Oh shit." I whispered.

I was pulling it out when her tongue ran across the sensitive flesh. I moaned as the tip left her mouth. I should leave. I stared at her tits and didn't see her eyes open. Her mouth enveloped me, and I gasped in surprise. I looked down and her eyes met mine. Her hand came up and wrapped around the shaft. I clamped both hands over my mouth as we began sucking me off. My hips moved on their own and I began fucking her face.

"So good," I moaned barely audible.

Mom pushed her head forward taking more of my cock between her lips. She withdrew suddenly, and I thought it was over. Boy was I wrong. She slowly sat up watching my dad intently. Sure, that she hadn't woke him up she grabbed my cock and led me to my bedroom. I felt like a dog on a leash. She closed the door behind us and spun on me.

"Finally. I fell asleep waiting for you." She admitted as she began stroking me.

"Sindy had homework that needed finishing." I moaned. "Damn that feels good."

"I know. It always feels better when someone else does it for you. I almost came a second time when I found your spunk on the bathroom floor. It took everything not to pounce you downstairs. I knew you took after your dad. It's not quite as long as his, but damn you are thick. I can't wait to feel this deep inside of me."

She kissed me to silence my arguments. Her tits pressed against my chest. I grabbed the negligee and lifted it up and over her head. It interrupted our kiss but not for long. Mom tugged my shirt off and pressed her tits against my naked chest. She moaned in my ear as she began squeezing my cock as she stroked me.

"So hard," she whispered. "I am so wet. You are going to slide into me no problem. I am going to make you come so damn hard."

"I am..." I said and fell silent. "God damn it, I am going to fuck you rotten!"

I was moving suddenly, and my back hit the mattress of my bed. We worked together to get my jeans off. A little while later I was looking up at the ceiling as she straddled me. She kissed me again as her hand took hold, aimed me, and lowered her pussy. I moaned into her mouth as her slit wrapped around me. She was right. I slid into her easily. I was balls deep in her snug cunt. She began moving slowly.

"So good," she gasped breaking our kiss. "How is it baby? How does mommy's pussy feel?"

"Tight... feels so damn good!"

"I am going to rock your world." She moaned. "I shaved my pussy for the first time today. I hear it is all the rage in Hollywood. Your dad hasn't even seen it yet."

"You and dad are swingers?" I asked as she ground against me as her hips made a circular motion.

"Yeah. Things got boring in the bedroom, so we decided to spice things up. Ask. I can see it in your eyes."

"What is it like? What happens?"

"It is so fucking hot! Like, well it depends how many guys are involved." She moaned as she leaned back letting me watch my cock slide in and out of her. "Men loving watching their cocks move in and out of me. Like the view champ?"

"Yeah. You said guys as in plural. What did you mean by that?"

"Your mom is a slut. I meant that I've been with up to three guys at one time. One in my mouth." She said opening her mouth wide. "One in my pussy just like you are now. And then one in my ass..." She growled as she turned around with my dick still buried in her pussy. "...see my puckered chocolate starfish? I always prep if I know that is going to happen. I clean it out like a good little whore. Your dick just got harder. Do you want to fuck my ass Sam? Do you want to slam your thick cock up my backdoor?"

"Are you serious?" I whimpered as she lifted her hips. "Wait... now?" I asked as she took me in hand and aimed it. "No way... oh shit mom!"

"Quiet, you'll wake your dad!" She urged as the head of my dick opened her up slowly. "Don't fret, I've already take care of it. My ass is ready for you. I was expecting your dad, but you'll do. Shit baby... you're going to split me in two!"

I watched as the head of my dick popped into her ass. Mom was panting and gasping as she stopped. A few minutes later she pushed her hips downward and the rest of my cock disappeared into her backdoor. I thought her pussy was snug, but her ass was a whole lot tighter. I warned her I wasn't going to last long but she just ignored me. I grabbed her ass cheeks and began thrusting upward. That drove her crazy. We set up a great rhythm until I warned her that I was going to cum. She began slamming her body against mine. I grabbed a pillow and howled into it as I came. Mom clung to me like a lover.

Lost Boy
Lost Boy
5,759 Followers