Deepest Darkest
- 2 years ago
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Note : This story is completely fictional!
It was shortly after my birthday, my grand entrance into my teenage years, that I first began my journey down the road of sexual exploration and desire by masturbating for the first time. It was an entirely new world, and a good one at that. I craved that sexual satisfaction for which I had little understanding of, but the greatest expectations.
This was the point at which I began to see my older, and only, sister, in an entirely new light. She was 3 years older than I was, and had entered high school. We were both very close siblings, and always had been. She however was beginning to truly grow up in every sense of the word. She was more mature, she wasn’t a kid anymore. She took on more responsibility, as well as an expanded social network. She was very athletic, and very smart. In a way I idolized her and looked up to her. At the same time though, I fantasized strongly about her. The body she developed as amazing. She had blond hair, blue eyes, perky breasts, and an ass to die for…and only at the modest age of 21.
Needless to say, visions of her filled my mind as I began to quite regularly masturbate. It didn’t take long before I was sorting through her panties. She had an assortment of sexy thongs and bras. I would try them on, sometimes getting off in them, while often times just sleeping in them. It was a fascination that I had, and couldn’t resist.
This continued for some time. I tried to resist most times, while other times I just gave in. Slipping on a thong and stroking my cock down in her vacant bed.
As I slowly matured myself, I began to grow out of my secret obsession, or at least for the time being. I hit my high school years, and met my first girlfriend, as well as formed a nice co-ed group of friends. My desires were now directed to the more likely candidates for my physicals desires. I’ll admit, I was, and still am I good looking guy. I was a bit on the quite side, but by my junior and senior years in high school people knew who I was, and meeting girls was the least of my problems. I lost my virginity, and the horizon was quite bright.
My sister at this time was away at college, and, in way, away from my mind. I myself was now getting ready to head off to college, and sexual conquest was once again at the forefront of my mind. I had grown up quite a bit since the first time I masturbated, but the sexual desire within my never wavered. Needless to say, my first year in college was very enjoyable, but what I didn’t expect to find was a girlfriend. I mean, why would I want a girlfriend when there are so many girls running around campus.
However, the girl was 21, and being only 18, I jumped at the chance to be with an older girl, or woman rather, who just happened to be the same age as my sister. We dated for an extended period of time…a period of time in which my sister came to know my girlfriend well, and become very displeased with her. As my relationship wore thin I began to rely more and more on my sister for advice…being that she was an older girl herself. Things ended with my girlfriend…but for the better, and it would be only a little while longer before I realized they were for the MUCH better.
Amidst my relationship woes, my sister had developed her own. Having been in what had become a difficult two year relationship with a younger guy, she was ready for change. In a similar fashion to me, she found herself single.
Having both having recently had difficulties with the opposite sex, we found it quite easy to turn to each other to bitch and moan about whatever was on our mind. She wasn’t reluctant to disclose information about her sex life either, and as a result those suppressed desires of mine were slowly creeping to the surface.
In a spur of the moment decision, knowing my housemate would be out of town for the weekend, I invited my sister down to school. I thought I would be a chance for her to get away from things, and allow us some time together. The possibilities turned in my head…but I tried keeping clear judgment.
When she said that she could only come for one night I tried to tell her it wouldn’t be worth her while driving all that way. She was insistent though, and who was I to stop her.
When she arrived she gave me such a tight hug…it was different then other times. There was a sense of relief to be with each other. She told me how long her week had been, and how excited she was to be getting out and do something exciting. I told her of my plans to start the evening with a nice dinner. It was the least I owed her for coming such a long way to hang out with her little brother. She was all for it, and only had to slip into some other clothes before leaving.
After about spending 15min in the bathroom she came out looking gorgeous. Her long blond hair curled, makeup on, a pair tight jeans, complimented with heals, and her amazing 32c’s tucked under a sexy pink blouse.
She asked how she looked…I almost stuttered…”Amazing”, she smiled, “Let’s go. I’m starved”.
The restaurant was a short walk from my apartment, and within only a few minutes we were sitting and waiting our turn to be seated. I felt proud sitting with her, and guys and girls alike glanced at her and I as they walked passed.
I excused myself briefly from her side to use the bathroom. It was on my walk back that I saw what looked like her talking with two older guys that appeared to be waiting in line themselves. In an effort to not kill my sister’s game I kept my distance. It took only a few reactions from her to realize she wasn’t interested in what the guys had to say however. I hesitated for only a moment; my window of opportunity had finally arisen.
I walked over as unknowingly as possible, and sat next to my sister. I put my arm around her and my other hand on hers, which was sitting on her thigh. I kissed her on her cheek, “Is everything okay babe?” It felt so natural…like it would have with any other girl. “Mhmm”, she responded, locking her hand with mine. I looked over at the guys sitting across from us in the waiting area, “Can I help you?” They both glanced away, “Sorry Bro…didn’t know she was your girl”. “Regardless, maybe you should show her some respect next time”, I responded, pulling my sis tight with me.
I overheard the hostess telling the couple waiting in front of us that it would be another 35 minutes until they were seated. I turned to my sis, “You maybe want to try somewhere else?” Before I could finish she had stood up, taking my hand, “How about we go back to your place?” I got up, “That sounds good”.
She kept holding my hand out of the restaurant and before any sort of clarification could come up about what had just happened she got a call from a friend back home. The remainder of the walk was taken up by her telling her friend directions to somewhere. Once back at my apartment she stayed outside of my door talking to her friend, she motioned to me that she would be in in a minute. She smiled at me as I went in the apartment, her eyes still bright, and obviously unaffected from what had happened at the restaurant.
As I ruffled through my cabinets looking for dinner possibilities I heard her
come back into the apartment. I wasn’t sure what to say or do so I just kept
searching through cabinets. I heard her footsteps right behind me, and then her
rap her arms around me. “Thank you so much for sticking up for”, she said. She
hugged me briefly and then let go so I could turn around. I leaned against the
counter, facing her, as she stood only a few inches from me. I just kind of
laughed…”It was the least I could do”. She poked me in the stomach and kind of
flirtacously cocked her head, “It meant a lot”.
My heart raced, was this really it, was my sister coming on to me.
“I mean…I can’t really blame them for hitting on you when you look like that”, I
looked my sister up and down. “Yeah?” she responded, “I guess I can see why the
older girls dig you so much”. “What can I say??” I laughed, biting my lip and
blushing, feeling so warm.
There was a long pause, my sister standing practically against me, just smiling. I brushed away the hair from the side of her face, and then leaned in and kissed her on her lower lip, sucking on it gently. I was scared at first. I was about to embark on the guiltiest of pleasures.
I felt her kiss back and her hands press up against my body. I put my hands on her waist and pulled her tight against me. Nothing was said…I needed her, and she needed me. Our tongues touched as we made out. I turned her around and sat her on the counter top. Kissing her down her neck and biting her ear. She lifted my shirt up and off the top of my head. My hands slid up the side of her body, pushing her blouse up, but not removing it. I wanted to savor this moment for as long as possible.
I continued to kiss her all over her neck and cleavage…sucking on her beautiful skin. I held her face as I kissed her hard on the lips, sucking on her lower lip as she undid my belt buckle. My cock was throbbing under my jeans. It was so real, so passionate. As I kissed her again on her neck she let out deep breathes as her hand pushed into my pants and onto her little brothers long thick cock.
“Oh my god..”, she took a deep breath, “You’re so fucking big”, she managed to say. I undid her jeans, “Is your front door locked”, she managed to say again deep breathes. I rested my forehead against hers, feeling her tugging on my cock, “Mhmm”, I responded.
I let her rap her legs around my body and I carried her into my room. I could barely push the door shut as she was the one now sucking on my neck. I stumbled back, and laid on my bed, my big sister on top of me.
I sat up with her straddling my waist, and lifted her blouse off. I immediately reached around and undid her bra. Her gorgeous tits hung out. I kissed her on the lips again. Sucking on her lips, feeling her deep breathes. I then put my mouth on her nipples, sucking and flicking them with my tongue. She rain her fingers through my hair as she moaned. I slid my hands under her waist line in the back, feeling her lace thong as I grabbed her firm ass cheeks.
I could feel her chest moving in and out with each breathe. “Mmmm” or “Oh my God” were about the only coherent thing either of us could manage out of our mouths, that is until said told me “I want to taste your cock so bad”.
She climbed off for a second and allowed for me to push my boxers and jeans off. My throbbing hard cock stood upright. She jerked briefly and then shoved it in her mouth. My body tensed. My sister’s lips rapped around the tip, and her tongue gliding all over it. I pushed the hair from her face. Her head bobbed up and down, the head of my cock hitting the back of her mouth. My eyes widened and my cock pulsed with every waking second.
I wanted to be inside of her so bad. I wanted to feel my sister.
She got off the bed and undid her heals. I wasn’t about to let her undress herself, I had waited too long for this moment. I stood up, kissing her as I pushed down her jeans first, and then rubbing her clit through her thong. Her thong was soaked. I couldn’t believe how bad she wanted it.
I almost ripped her thong off as I slid it part of the way down, and then she stepped out of it. We stood there kissing for about a minute, our tongues so far in each other’s mouths. I fingered her pussy. I couldn’t believe how good it felt. Her juices dripped from her vagina lips. I got on my bed, reaching in my desk drawer and pulling out a condom. As I put it on she straddled my stomach, kissing my chest. I threw the rapper on the floor, making sure the condom was on tight.
She inched back on my body and reached with her hand for my cock behind her. Taking it and pressing the head on her pussy. She looked up at the ceiling, her mouth wide open as she moaned, as my dick slowly slid into her.
I pulled her down close to me. I kissed her on the lips. I held her face so that her hair didn’t hang, and so that I could look into her eyes as I started thrusting in and out. My cock glided deeper and deeper into her. The only thing I could think about was making her orgasm.
“Oh my god, oh my god” was all she could say. I kept thrusting at different angles, eventually hitting her g-spot. “Ohhhh” she moaned. I knew I had her close. I thrusted in and out, in and out, as fast as possible. My cock was tingling, my body tensing. I knew I had to hold my orgasm. Her body laid on top of mine as she buried her face in the pillow next to her my head. I could feel her fingers dig into the side of my body as her body shivered on my cock. The tip of my cock slipped out of her soaked pussy, her cum collecting in between my legs.
I rolled her over onto her back, putting her legs on my shoulders. I started fucking her deeper, and faster. I knew she could cum again. I leaned in and bit her lower lip as I worked my big sisters moist pussy. My cock tensed harder, I knew I was going to cum. I gritted my teath. “Are you close?” she asked me, “Uhuhh”, I managed to get out. “Cum with me” she responded. I gripped the bed beneath us as hard as possible and fucked her all out. My cock slamming into her pussy. Her nails digging into my chest as she screamed. My cock filled with my hot cum. My dick pulsing inside of her. I kissed her with such passion. Her hands now wrapped around my head. Our body’s soaked in sweat.
I pulled out. Taking the full condom off. I kissed her all over her body, and then on her lips again. We looked at each other, our minds at a complete loss. “Promise me we will never stop this, she said. “Never”, I responded.
We fell asleep with our bodies tight together. We would fuck again once more in the morning before she had to leave. We kissed each other good-bye, exchanging “I love you’s”.
She later texted me that she had left me a secret under my pillow, and when I looked I found her thong from the night before. I laid on my bed with only her thong on, masturbating to her, just like I had 7 yrs before.
While this story comes to an end, another has only just started.
**This is my first time...wanted to try this for a awhile now. Let me know what you think. Thanks for reading**
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Book Eight: Labyrinth of Love Chapter One: The Shaman's Desires By mypenname3000 Copyright 2016 Note: Thanks to B0b for beta reading this. Knight Kevin – The Free City of Hargone The splashing, gurgling fountain cooled the inn's common room. It was an aptly named establishment, though the innkeeper was not happy we had commandeered his entire main room despite the gold we paid him. The twelve of us sat around a circular table, reclining on tasseled pillows. My fellow knights and I...
Nancy Conners was basking in the warm afterglow of a wonderful fuck. Her fingers trailed down her tight stomach, over her bare pussy mound to run gently over her still engorged clit. She could feel Jim’s cum beginning to leak from her well-fucked pussy and Jim’s eyes as they drank in the beauty of her dancer’s body. Jim loved Nancy’s small tight frame, her pale skin, entrancing green eyes, fiery red hair. Her small hard tits had the most responsive of nipples and Jim loved to see the...
FetishHey, Fellas, Hope all are well, and enjoying the world of sex n relationships. So, today again I am here to share one of my experience which happened in Pune in this sex story. I’ll wait for your valuable feedbacks. Please take out a minute from your precious time to write me on So, here we go: This happened in January 2017, one fine morning, I woke up and saw my mobile screen which displayed a notification sent you an email. I opened the email and it says “Hi Vicky, I like your sex story on...
Hi I am Shankar, ma aunties name is Vanitha. she has big boobs and a big ass, I always use to wait to see her beautiful thoppul(navel) and her cleavage whenever she exhibits it without her knowledge. I always use to think of her and masturbate and I even use to sniff her used panties in her absence. I have noticed many times her panties lying around her room it would be very wet often, and of course it’s her moothiram (pee). I use to lick her panty in the area where her pussy and shit hole...
IncestAs I looked into her eyes, I knew it was true, and there was nothing I could do about it. Her eyes locked onto mine, conveying everything. But still i stood there, my cool brown locks wafting in the slight breeze and my rosy glare locked on to hers, the connection still there. Both she and I had waited so long for this moment, and both of us were hesitant. Neither of us wanted to take this step. Neither of us wanted to do this now, and maybe not ever, yet both of us needed to. Not by...
Dillon turned the shower on and started to strip angrily, pitching his clothes at the floor as if attacking the wayward wonton desires that had started to surface. Ripping his pants off, his painfully hard erection sprung forth. Scowling down at it, he was furious that he was feeling so aroused by this whole thing. “This isn’t me! I’ve never been so immediately turned on by a chick I barely know. Sure if it’d been any of the other chicks in my class I’d probably have been curious but I...
KAYEI love people, but I don’t enjoy being treated like some naïve teen who doesn’t know what’s best for her.I’m a card-carrying adult, fully allowed by law and motivated by disposition to engage in any ethical activity of my choosing. Yeah, my short stature, girlish face, and medium-small breasts might freak you out at first sight. However, if you were ever lucky enough to sample my surprisingly curvaceous ass on your face while I begged you, husky voiced, to taste my cunt, you’d know...
BisexualMy name is Jona, age 24, short person with big and hard cock from Andhra. This is my second real story posted to ISS. This story shares my erotic experience with a young neighbor aunt. This incident took place before 2 months back. I attended one program where this aunt also came. We had good photo session. I uploaded the pic in Facebook. One evening my neighbor aunt told me to tag her in the pic. I told her that I don’t have her mail id. She gave her id. Through fb we became close friends. She...
Hiiiiii. My name is Krishna. I come from a family that comprised of my father, mother and me. My father was working as a manager in a private firm and my mother was a housewife. We were a typical middle class family and live in Hyderabad. We were a happy lot. This story is a mere fantasy. Tell me how you liked this story. Mail your comments to “”. I completed my B-Tech examinations and in the summer vacations decided to make a trip to Vizag to meet aunt and my two cousins, Vineetha and Nitya....
Wanna be my friend? Then save me the embarrassment of denying your request for simple things. Besides.. some of these guidelines are kinda standard around here... so consider it friendly advice if you don't happen to meet my personal criteria.These conditions are obviously subject to change and / or be enforced at any time - exceptions MAY be made. Reasons i might ignore these self-imposed rules? If you are close, willing, eager, and friendly, if you have read my profile, and examined my...
Disclaimer: Strong gay BDSM themes,if either of these offend you please do not read any further. This is a story,remember in real life the importance that everything is safe, sane, and consentual.Please do not reproduce or republish this story without consent of the author. Chapter 1 Charlie went about His studio double checking all His equipment His heartslightly racing within His chest. He always got nervous before the big moment,but Charlie's dark eyes never showed the smallest trace of...
My name is Sam Davies. I'm a rich, influential Hollywood agent. My life is quite standard for my job, although I have always found it quite hard to stay professional with so many hot women around me. I could fuck ordinary women, but they weren't enough for me, I wanted the "elite" ones. But, on the other hand, I didn't want a sexual harassment charge, so I've always been forced to stay professional. That is, until today. Today, I woke up and saw that I'd got a letter. It read: Dear Mr....
Mind ControlChapter 1 Monica was 21-years old and she was already a very mature young woman physically. Maybe she wasn't really that mature mentally at that age, but that maturity would come and come in a big hurry. Monica had some sexual experience by that point in her life -- she certainly wasn't a virgin, and she'd gain much more sexual experience in the days ahead. Monica had boyfriends and even a married lover before she moved to Washington DC and there was one thing for sure about Monica, when...
Kate’s finger hovered hesitantly over the mousepad of her dated laptop. As she closed her eyes and sucked in a deep breath, she swiftly clicked down on the button. Just like that, her tantalising order of erotic goodies disappeared from her screen, shot though the invisible depths of the internet and promptly delivered to the “Enchanting Desires” warehouse.As Kate looked back over the items she had just purchased for her upcoming anniversary with her boyfriend Cameron, she couldn’t help but...
Straight SexI met my wife Viki in 2007 when she was twenty-two and I was twenty-five. I am half-Thai and half-Indonesian while Viki was pure Thai, from a traditional Thai family in Chiangmai. She had just graduated and had come to work at the travel agency where I was the manager. It was love at first sight for me. She was small, only five feet tall, but very pretty, with a great smile and a slim but curvy figure. I'm about five-feet, four inches, and about seventy kilograms, so not the best built, but she...
CuckoldSurrendering to Our DesiresMy name is Jessica. I'm 29, work in publishing, and have been completely faithful to my boyfriend for the past six years. Until today. Today I'm on my knees in the Denver hotel room of a coworker. My lipstick is smeared. My top and panties are both gone, leaving me in only my black skirt. My nipples are hard as rocks and my pussy is swollen with desire as I slowly pull down the zipper in front of me and reach into Jamal's pants. I'm not disappointed.It takes some work...
1. A BIG SurpriseIt's funny how you never really see things coming until they hit you right in the face.My life was about as normal as possible. I am thirty-two, still in great physical shape, and a basketball coach at one of the top ten high school basketball programs in Texas. I have a younger girlfriend who keeps me on my toes and in great shape from all the sex. She is a nymphomaniac and very adventurous. My first sexual encounter in public, my first blow job while driving, and my first...
I have adapted this story from another and enlarged it by over 75% The beginning was a good example of a scenario I had wished to start a story from and I was encouraged to adapt, enhance and take the story on from there. I hope you enjoy my most recent offering. NEW DESIRES. The neon sign proclaimed that good food, drink and fun could be found inside. Just fun? Or something more? Inside, fun gave way to passion, which then gave way to… sex, or at least the yearning for it. The...
Wife Lovers"That's a good girl, Lorelie. Show our visitor a bit more of your delightful wiles." Master Don lifted the angelic face of his favorite charge. His ice blue eyes burned into the smoldering depths of her lush green stare. A corner of his mouth lifted in a slight smile as her eyes favored him with devotion. "As you wish." Lorelie lifted up on her tiptoes and placed a kiss on her master's smiling lips. Her raised posture inspired an appreciative display of milky-white skin, legs molded in...
Katie Jackson sat at home on her couch with her sexy toned legs curled underneath her as she stared at the television. The commercial came on as scheduled in the middle of the evening news as she lifted her phone to record it for her husband. It was for a fundraiser for the City Union Mission. Since her announcement of winning the beauty pageant the local chapter of City Union Mission had used her talents to promote their charity. The commercial had been playing all week on the local channels...