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A Dreamy Nightmare

Categories Diary, BDSM, Cruelty, Incest

Author: starrynight

Published: 29 October 2018

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A Dreamy Nightmare

An original stort by Starrynight

I am trying something very different from what i usually write about.

Would be happy to get your opinion on the story.


Spring was upon us, or so I noticed as I looked out the window of my bedroom. I noticed the distant hills turned green and the flowers began to blossom in the backyard. A gentle breeze blew in through the open window, bringing with it the sweet smell of spring. It was the first day in a while that I could be in my room with the window ajar without freezing, and after taking a pause to enjoy the calming breeze, I turned back to the computer and went back to doing my homework.

I was nearing the end of twelfth grade and knew that I would be out of my mother's and stepfather's house in no time. I kept working on my homework in the silence of the empty house, enjoying the quiet that was disturbed only by the occasional car, or distant bark of a dog when the doorbell rang.

That must be her I thought to myself as I dragged myself out of the chair and headed downstairs to open my door to my stepsister Erin. It was almost a year since I saw her last, and I knew she was coming to stay with us for a while.

My stepsister Erin was twenty-eight years old and we weren’t very close. She worked as a Sommelier in a fancy restaurant and lived with her boyfriend who worked in some private security firm. Apparently, he had to go on a long business trip abroad, so Erin used the opportunity to take some time off work and come stay with us.

"Hi sis" I said with half a smile as I opened the door and saw her standing there. Damn, I forgot how hot she is, I thought to myself as I looked at her standing in the doorway.

"Jason!" she called out happily with a smile and wrapped her arms around me for a hug, pressing her impressive rack into my chest.

"How was the drive?" I asked Erin as she entered the house, pulling her large suitcase behind her.

"Long…" she said with a tired laugh "Where are dad and Karen?" she asked after putting her suitcase down.

"They went out to brunch and a movie I think," I told her and studied her beautiful body "you want something to eat or drink?" I offered politely.

"Nah, maybe later, " Erin said "right now I'm pretty beat from the drive. I think I'll just take a shower and maybe a nap" she said.

"Okay, mom already fixed the guest bedroom for you." I told her "Do you want me to help you with your bag?"

"Sure, thanks" she said, and started climbing the stair. I grabbed her bag which was heavy and followed her up the stairs, using the opportunity to look at her nice plump behind. I followed her into the guest bedroom and placed her bag down with a thud.

"I think you're all set" I said to Erin and she thanked me. "I have some school work I need to get done" I told her. "I believe you remember where everything is, so make yourself at home." I said and with that left her room and closed the door behind me.

I entered my room and closed the door behind me with a sigh. I had forgotten how hot Erin was, I realized after seeing her. When mom remarried, Erin was already in college, so we never lived under the same roof. She would come to visit a few times a year but usually it was only for a few days. I always thought she was pretty, but only when I hit puberty did I start to fantasize about her. I would often masturbate while picturing her, especially on weeks following her visits when I would be reminded of her sexy body.

I walked over to my desk and opened one of the drawers. I took out a picture of Erin and me from a few years back and studied it. I was fourteen in the picture, Erin was twenty-four and it was taken while we were on a family vacation at the beach. I looked at Erin smile at the camera, with her hand around my shoulder. Her fiery red hair was wet from swimming and her light blue bikini top was cupping her large beautiful breasts nicely, showing just a trace of her nipples beneath it.

I noted that she put on a few pounds as I looked at her long legs in the picture, but decided it suited her, remembering the way her plump bottom swayed as I followed her upstairs, her tight jeans hugging her ass and legs and emphasizing her womanly curves.

I was startled by the sound of the bathroom door closing outside my room, and quickly put the photo back in place and turned back to my homework as Erin turned the shower on. I tried to focus on my homework, but it was hard to concentrate. I kept thinking about the fact that just on the other side of the wall Erin was showering naked.

After a few minutes I finally gave up on homework and decided to take a break and grab something to eat from the kitchen. I got up, and just as I left my room I heard the bathroom door open and Erin walked out. Her long red hair was wet, and she had a white towel wrapped around her. The towel was covering her from chest to mid-thigh and showing off a nice amount of cleavage.

"I really needed that shower" Erin said and gave me a smile before walking over to her room and closing the door behind her. I started heading downstairs as I passed next to her door. I was so turned on that as I passed her door, I couldn't help myself. I crouched down on my knees and peeped through the keyhole in her door.

My cock instantly turned hard as I made out the image of her naked bottom. It was so juicy and perfect that I couldn’t take my eyes off it. I stared at it for a few seconds as Erin supposedly looked at herself in the mirror. She stood there facing away from the door for a few seconds when suddenly I saw something white covering her up and noticed she headed for the door.

I panicked when I realized my stepsister was heading my way, and quickly ran over to the bathroom and closed the door. From inside the bathroom I heard Erin open her door and close it a second later. I was so horny from what I just saw that I masturbated wildly to the thought of her naked bottom until I came hard.

The following days I couldn't stop ogling Erin and her sexy body. Everything about her turned me on. From her bright red hair, her thick red lips, her large shapely boobs, her flat stomach, her curvy hips, her luscious ass, her smooth thighs and her long legs.

One night on her second or third day home, I went to brush my teeth before bed. I was just in a pair of boxers and as I entered the bathroom Erin was already there. She was brushing her teeth and gave me a smile as I walked in. She was wearing just a pair of black panties and a loose white shirt with no bra underneath. I could see her nipples poking under the shirt and felt my cock get hard. I started brushing my teeth and tried not to look at her fine, panty clad ass and bare legs but it didn't help. I was hard in no time and pushed my erection against the counter, so it wouldn’t be noticed.

"Good night" Erin said after she finished brushing her teeth and left the bathroom. I mumbled good night in return and as soon as I heard her door close I closed the bathroom door, pulled my less than average cock out and jerked it off until I exploded.

Most days when I woke up, I would hear Erin in the shower and wait for her to finish while getting ready for school. I would hear her turn the shower off, then I would open my door and wait for her to exit, always with a towel around her as she headed to her room and closed the door.

One morning, Erin got out of the shower when her phone started ringing. She quickly opened the bathroom door with the towel hastily wrapped around her. She bid me a quick good morning and hurried to her room where I heard her answer the phone. I was just about to go into the bathroom when I noticed her bedroom door wasn’t completely closed. I tiptoed to it and peeked in through the open crack.

To my delight, Erin had let the towel fall to the floor, and was looking out the window while talking in her phone. She was completely naked, and I could clearly see her bare backside. I watched her plump tush wiggle as she talked on the phone and I could feel my dick harden. Erin was walking around the room as she spoke into her phone, at the beginning with her back to me, but after a few seconds she faced the bed.

My cock almost burst as I got a glance at her side. While I did not have a view of her pussy, I did clearly see the side of her left boob and just the side of her large pink areola. It was so hot I had to get a better view. I knew that if I only pushed the door a little more, I could see her left nipple and maybe even her pussy. I waited for Erin to keep moving, hoping that she will face the door and I could see her complete unconcealed body. I waited for a few more seconds, and when it looked like she wasn't going to move, I pushed the door a little as gently as I could.

I only got the briefest of glances at my stepsister's nipple as I opened the door when to my horror, it creaked. Erin instantly shot her head towards the door, giving me a split-second view before I ducked out as fast I could. I quickly jumped into the bathroom and quietly closed the door behind me as my heart raced.

All that day, all I could think of was my stepsister naked. It was one of the most beautiful sights I had ever seen, and I just had to get a glimpse of her again, no matter what.

The following day, still obsessed with seeing my stepsister naked, I decided to peep on her in the shower. Just like the previous days, I woke up just as Erin walked into the shower. I heard her enter the bathroom then turn on the water. Just like every morning, Erin did not bother locking the bathroom door and I got ready and went over to the hall to wait for Erin.

I opened and closed my bedroom door very quietly and stood outside the bathroom. I stood there and waited in anticipation for Erin to finish. A few minutes later, I heard Erin turn the shower off and that's when I acted. I opened my bedroom door as loud as I could from the outside and burst into the shower trying to look as though I thought it was empty.

"Jason" Erin called in surprised as I walked in on her just as she was grabbing the towel. She had not managed to cover herself up yet and I got my first full view of her naked front, her large heavy breasts and fiery red bush looking so hot. "What the hell are you doing?" she asked in alarm as I barged in and just stood there looking at her naked body. It took her about a second to cover up with the towel.

"Sorry," I said "I didn't hear the shower running so I thought you were finished already" I continued and tried to sound as nonchalant as possible.

"Get out!" she said angrily "I am not finished."

"Okay, calm down" I said like it wasn't on purpose and left. I left with image of my sister naked fresh in my mind.

That day when I got home from school, only Erin was at the house. She told me my stepdad and mom went out to dinner and won't be home until late. I made myself a sandwich and took it up to my room where I watched some TV and did my homework.

"Yeah, come in" I called when I heard a knock on my door after about an hour later. It was Erin, she was wearing a pair of tight jeans, an orange tank top that showed off a nice cleavage and was wearing her hair in a ponytail.

"Hi, can you come to my room for a sec?" she asked innocently after she entered my room.

"Sure" I said and got up without giving it a special thought. I assumed she had an issue with her computer or something and followed her over to her room. When we got to her room she turned around and looked me straight in the eyes.

"I know you were peeping on me the last few days" she said directly and gave me a stern look. I could feel my face turning red.

"No, I wasn't" I tried to deny and hoped I sounded convincing.

"Come on Jason, I saw you peeking through the crack when I was on the phone the other day, I know that you didn't really think the bathroom was empty when you barged in on me this morning, and I see the way you check me out when you think I'm not looking." She said angrily.

"Okay, so maybe I was." I said defensively.

"Are you going to stop?" she asked.

"Are you going to tell my mom?" I asked in return, a little scared she would.

"How about this, if I do something for you will you promise to stop perving on me?" she asked me without answering my question.

"Do something for me? Like what?" I asked surprised. I had no idea what she was talking about.

"Clearly you're a little obsessed with seeing me naked. Will you promise to stop peeping on me if I give you a handjob?" Erin said with a straight face.

"A what?" I asked shocked and nearly chocked.

"If you promise to stop spying on me naked. I'll give you a handjob while I'm naked." Erin said and sounded like she meant it.

"Are you serious? You are really going to give me a handjob if I stop spying on you?" I asked still uncertain she was serious.

"Yes" Erin said plainly.

"Okay, if you really do it, I promise I will stop" I said hoping not to sound too eager.

"Good, so take your clothes off" Erin said.

"Right now?" I asked her nervously.

"Yeah, let's get it over with" Erin said. I paused for a minute and kept looking at Erin. I still wasn't sure she was serious. I wasn't sure if she would let me take my clothes off just to take a picture of me or something and threaten to use it if I didn't do whatever she asked of me. "Fine, I'll take my clothes off first you wuss" Erin said annoyed and to my surprise started taking her clothes off.

I watched amazed as my stepsister started to undress in front of me. She started out by removing her top, revealing her white bra as it cupped her large round tits. She followed by unbuttoning her jeans and pulling them down along her long legs, exposing her crème colored panties. Next, she removed her bra, and finally her panties, until my gorgeous stepsister was standing completely naked in front of me.

I couldn't believe this was really happening as I gawked at my busty naked stepsister. I ran my eyes along her marvelous body, from her bright red ponytail, her green eyes, and full red lips. To her huge amazing breasts, probably around a DD, her big pink areolas and large enticing nipples. From there down her stomach to her trimmed ginger patch and her inviting pussy, all the way down her curvy thighs and long legs.

"Well, are you just going to stand there and stare like some perve or are you going to take your clothes off?" Erin asked. I was now sure this was no prank and I quickly took my clothes off. I removed me shirt, pants, and boxers in seconds until I too was naked, my 5-inch cock already hard.

"I guess I can work with that." Erin said as she eyed my hard penis and skinny upper body "One more thing, I want to tie your hands together." Erin added.

"What, why?" I asked alarmed.

"So you want get handsy," Erin said "I said I'll give you a handjob and I will, but I don't want you to start feeling me up."

"No!" I protested.

"Fine, then no handjob" Erin said coldly.

"Okay okay, but just my hands" I agreed. After seeing her naked and grasping the fact that I was going to get a handjob, there were only a few things I wouldn't have agreed to.

"Just your hands" Erin said and turned around. She walked over to the closet where she bent down to one of the bottom drawers and gave me an amazing view of her juicy ass. "This should work" she said and stepped back over with a sort of thick scarf.

I put my hands behind my back and turned around as Erin used the scarf to tie both my hands around my back tightly. This was feeling kind of kinky, but I wasn't going to complain.

"All set." Erin said after making sure my hands were secure "Go ahead and take a seat on the bed" she added, and I did. My cock was throbbing with anticipation for my first handjob ever.

After taking a seat, I watched my sister as she stepped over to the nightstand. She opened a drawer and pulled out a small bottle. She then stepped back and got on her knees.

I watched my sexy naked stepsister as she stared at my erect cock. She opened the small bottle, placed it over the tip of my cock and squeezed it. I gasped with pleasure as the slick liquid dripped down my cock and coated it. Erin closed the bottle and put it down before closing her right hand on my erection.

I moaned with pleasure as Erin closed her hand around my cock and squeezed my shaft before using it to coat my cock with the lubricant. I groaned as she slid her hand all across my penis then grabbed it again and started stroking me.

"Oh fuck" I said with a moan as my older stepsister jerked my cock. She was going slow, and it felt amazing as she ran her hand up and down my shaft, slowly rubbing the head of my cock, then gliding it down along my shaft and caressing my balls.

She kept going slow like that for some time, sliding her hand along my slippery cock as I looked down at her magnificent tits. The whole thing felt so amazing that after two or three minutes I felt I was close. I started moaning louder, the pleasure her nibble hands afflicted on me grew, and I was seconds away from my climax when Erin let go of my cock completely.

"What are you doing?" I asked as my excited dick begged for a release. I tried to bring my hand over to finish the job myself when I remembered they were tied behind my back.

"Not so fast little bro" Erin said with an evil grin and just looked at my twitching cock without touching it.

"Keep going" I told her angry, but she just looked at me and said nothing. I waited eagerly for a minute of eternity until Erin grabbed my cock again and I let out a gasp as she continued to stroke it, going even slower this time.

"Does that feel good?" Erin ask as she kept on slowly jerking my cock.

"Yes" I said with a moan as she squeezed my cock a little harder and started stroking faster. "Oh god yes" I said and looked down at her amazing naked body. She kept stroking faster, making me moan loader, and just as I felt I was about to cum, she stopped and let go.

"Please keep going" I asked on the verge of an orgasm, but Erin just looked at me amused. My cock never throbbed like this in my life and all I could do was wait for my stepsister to keep going.

"Do you promise you will stop peeping on me you little pervert?" Erin asked after watching me squirm for a little.

"Yes, I promise" I almost screamed. She gave me a look of contempt before finally returning her hand to my cock and commencing to stroke it.

"Please, please let cum" I begged my stepsister as I felt my orgasm near for the third time. She was going so slow that it took me longer this time, but I was getting close. "Fuck, Erin, please, I'm begging" I said and moaned. I prayed that this was it, but just as I was about to orgasm, she grasped my cock and stopped stroking it.

"Will you ever peep on me again?" she asked with another evil smile.

"No, no, I promise" I pleaded but to my frustration Erin let go of my cock.

"No, please don't, please keep going" I begged. I felt like I was about to cry but held back. I wanted to scream at her, curse her. I wanted to torture her, to tie her up and plunge my cock into her snatch as hard as I can, to hear her scream as I destroy her ginger pussy, and just when she thinks I finished, to turn her around and shove my cock into her fat ass while she screams for mercy. Instead, I kept quiet and waited until she put her hand around my cock again and started stroking.

"Enjoying yourself little brother?" Erin asked with a taunting smile as she stroked my cock. She was going a little faster this time and I hoped it was a good sign.

"Are you going to let me finish now?" I asked with a moan.

"Oh, do you want me to?" she asked teasing.

"Yes" I said with a groan.

"Then I'll make you cum this time little brother" she said and looked me in the eyes.

I wasn't sure if she was telling the truth or just playing me, letting me think I was finally about to cum only to have her stop at the last second. She was still going faster, and after a minute I felt close to cumming.

"I'm close, please don't stop" I begged Erin in a pathetic voice. I felt like my balls were about to explode. "Please" I moaned as I got closer, "please!" I pleaded, and Erin started stroking me even faster. "Oh my god, yes! Fuck! FUCK!" I screamed as Erin finally made me cum.

It was the best and strongest orgasm I have ever felt. My entire body shivered with pleasure as my balls tightened and released. I shot more cum than ever before as my cock squirt load after load of thick sperm all over my legs. Erin kept stroking me fast throughout my climax until she milked my cock completely. She then slowed down, but kept stroking me slowly, making sure to stroke my entire length.

"You can stop now" I told my sister out of breath after my orgasm ended.

"I don't think so" Erin said and started stroking my cock fast.

"Uuugghh" I groaned as a wave of sexual pain ran through my cock and made me wince. "What the fuck are you doing?" I snapped at her as another wave of pain shot through me.

"Making sure you don't forget your promise" Erin said, then brought her other hand and started stroking my cock with both hands.

"Oh fuck, stop!" I called, and my legs shivered. Erin kept stroking my shaft to her sadistic pleasure as she used her other hand to rub the head of my cock hard, placing her palm on it and scrubbing the sensitive skin as I groaned. "Fuck Erin, please stop!" I whimpered as she squeezed the head of penis between her thumb and index finger.

My penis refused to go soft as Erin kept torturing it. She seemed to enjoy herself while I grimaced in pain. She rotated between slowly stroking my shaft with both her hands and squeezing hard, to grabbing my cock in one hand while using her palm to rub the sensitive head.

"Fuck Erin, Stop, I can't take it anymore!" I cried out in sexual pain. "I promise I'll never spy on you again" I said in a hoarse voice as I continued to groan and whimper. My body kept on shivering and I felt like she was rubbing the skin of my cock as she scrubbed the head hard for a final second and then let go.

I grunted as Erin finally released my cock, sending a final shiver down my spine. I panted and looked down at my red cock, it was still rock hard.

"We're not done yet little brother" Erin said to my horror after giving me a full minute of mercy.

"No Erin, please!" I begged and nearly started crying. In return, Erin looked at me with contempt then pushed me on my back onto the bed.

"I want to have a little fun too" Erin said and got to her feet. I watched her as she climbed on top of me and pressed her pussy onto my erect cock, her red pubic hair feeling coarse as my dick pressed into it.

"Erin, what are you doing?" I asked surprised, thinking she was about to fuck me, but instead, she pushed my cock into my stomach, moved over to it and started grinding her pussy along my never-ending erection.

"Oh yes, that feels good" Erin whispered and closed her eyes as she kept pleasuring herself upon my raw cock. It felt better than her hand, but my tortured member was still not enjoying it.

I watched Erin as she placed her hands on my chest and continued to grind her ginger cunt onto my meat. Any other time, my stepsister grinding her snatch on my cock would have been a dream come true, but after a while of her molesting my poor cock, I just wanted her to stop.

"Fuck you, you bitch!" I screamed out as another spasm of pain shot through me, but Erin just kept going as she moaned in pleasure.

I don't know for how long Erin kept this up. I closed my eyes and clenched my teeth, letting out grunts as Erin continued to moan in pleasure. I could feel every nerve scream with searing sexual pain until I felt another orgasm coming on.

"Oh fuck!" I yelled and opened my eyes as I started to cum. I saw Erin's amazing jugs sway from side to side as she kept grinding herself onto me. It was the worst and yet one of the best orgasms of my life. I felt searing pain mixed with electrifying pleasure as I started shooting my load onto my stomach and chest. My body shuddered, and I groaned like an animal as I kept ejaculating while my stepsister kept grinding into my cock.

"That was hot" Erin said after I finished cumming and kept grinding herself into me in perverse delight. I kept shivering in pain for a few seconds as she continued and then finally stopped and got off me.

Erin went over and sat down on a chair near the window. She spread her legs, showing me her pink pussy and started rubbing it while looking at me laying there. I tried to sit up, but my body was so weak, all I could do was lay there and look at my sister as she started to masturbate.

"Get a good look bro, because that's the last time you're ever gonna see it" she said and moaned as she pushed her middle finger into her snatch. She then moved her other hand down along her body, pinching her hard nipples before brushing along her red bush and starting to rub her clit in circular motion. "Oh yes, yes!" she called out in a high-pitched voice and closed her eyes as her body shuddered gently.

Erin sat at the chair without moving for a few minutes and only then did she get to her feet. I tried to sit up and succeeded. Erin moved closer to me, went around my back and untied me. My cock was limp by now but was still burning. It felt like someone poured hot sauce on it.

"You’re crazy" I said to Erin after I got to my feet and looked at her naked body.

"Maybe," she said innocently "but I bet you will think twice before spying on me. And anyway, I don't think you will want to jerk off in the next few days." She added. I brought my hand to my cock and felt a wave of pain as I grasped it. It was so raw I knew it would hurt like hell if I try to masturbate in the next few days.

I gave Erin's smoking hot body a final glance, then turned around, grabbed my clothes, and got the hell out of there.

The End

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