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Loving My Sister Jessica

Jessica and I had been very close growing up. Although I did torment her as big brothers often do to younger siblings, I was also very protective of her. I always ensured the guys she dated as a teenager knew their boundaries and even helped get her out of trouble with our parents a couple times.

Jessica was born in 1969 when I was almost 2 years old. My earliest recollection of her was when I was about 4 or 5 years old. Before I was in school, we used to spend time at our grandmother’s house as both our parents worked. As we grew older, we would spend the entire summer with Grandma, often in the company of our cousins. We would also fend for ourselves for a couple hours after school until our parents got home from work as we got a bit older.

Perhaps it was the fact Jessica and I relied on each other so much that brought us as close together as we were. Our relationship took on a whole new meaning of close during the summer after my 13th birthday.

While I cannot remember exactly what led to our first game, I do recall several times both Jessica and I were present with other kids in the neighborhood as we all played games such as “Spin The Bottle,” “Doctor” or “Post Office.” While I never recall anyone forcing anyone to do anything they didn’t want to do, some of the kids were hesitant to “go all the way.” Jessica never shied away from a challenge. She always seemed to enjoy putting on a show or being the first girl in the group to explore new territory.

My first orgasm involved my little sister. Someone in our group dared us to “hump” each other. At the time, neither of us knew exactly what was really involved in intercourse. My knowledge was based on a few porn magazines I’d seen and neighborhood “folk-lore.” Jessica and I eagerly accepted the challenge in the club house where most of our neighborhood games took place. Jessica and I stripped down and I remember putting my penis between her legs against her then-bald pussy and humping her. After a few seconds of this dry-humping, I remember my body quivering and a very sensitive feeling shooting through my dick. I recall something spurting from the end of my cock onto my sister’s leg and bald pussy lips. I remember some of the kids thinking I had peed on my sister. Little did I know at the moment that I had just experienced my first orgasm. Only later when I was masturbating and actually made myself cum was I able to put two-and-two together; stroking or stimulating my cock produced this incredible feeling. As with all young boys, I loved it and did it as often as possible once I figured out how good it felt.

I recall discussing this “discovery” with Jessica and her telling me she wanted to see me cum. I took Jessica to my room, got out my favorite secret Hustler magazine and proceeded to masturbate for Jessica. My little sister watched in awe as I shot a load of cum into the tissue in my hand.

As time went on, the neighborhood “games” occurred less often but I found Jessica and I playing together more and more. She was growing into a beautiful young woman in her pre-teen years. Jessica started to develop breasts at around 12 years old and it seemed like by the following summer, they were as big as their current size; very full, round, voluptuous 38C’s, 38C’s I played with as often as she’d let me.

Jessica and I grew very open with each other sexually. It seemed natural for me to perform cunnilingus on my sister or to have my sister stroke my cock for me. We honestly did not think or feel we were doing anything wrong although on some level, we must have known since we knew enough to keep it a secret.

At some point along the way, Jessica allowed me to take her virginity. The first time was awkward for both of us but we continued having sex when we could. By the time I was 15 or 16, fucking my little sister was incredible. She had developed very dark, thick pubic hair and her pussy began to resemble those in my porn magazines and not that of a young girl. Her body became very curvaceous and she had developed a sense of sensuality about her that was incredibly appealing to me.

Jessica and I were never concerned with protection nor did we fear pregnancy. She allowed me to fuck her without a condom and always insisted I cum inside her. She learned the art of fellatio as a young girl by practicing on her older brother. Having an incredibly sex-starved little sister also provided the perfect opportunity for me to learn the finer art of pleasing my women partners; sensual massages, how to properly finger-fuck, how to eat a pussy, how to slowly train a woman’s ass for anal sex. Jessica was the first girl I ever titty-fucked and she actually seemed to enjoy having me cum on her tits, chest, and neck more than I did. We went through baby oil at an alarming rate and actually prompted our mom to question her once. Jessica played it off perfectly, claiming she used it as body moisturizer to keep her skin soft.

While some may see this as evil, twisted, disgusting, and perverse, it was normal and natural to us. I grew to truly enjoy my erotic encounters with Jessica.

After graduating from high school, I left for college. Jessica was still a junior in high school as I started my undergraduate studies. Jessica ended up getting a scholarship to a college on the east coast and after I earned my degree, I landed a job on the west coast, thousands of miles from my sister.

During those years, both of us had many other healthy intimate relationships. In all aspects, we were normal members of society who happened to share a wonderful, secret past.

Jessica and I remained close through the years. We both ended up marrying, her to a very nice gentleman she met at work and I to a girl I met in college. We’d see each other every other year or so as we traveled to our parents house for Thanksgiving or Christmas holiday reunions. We’d exchange family pictures via mail and later via e-mail and talked on the phone about once a month. Jessica and I did our best to bridge the 3,000 mile gap.

As adults, we never talked about our sexual relationship as teenagers. I often wondered if she now, as an adult, felt angry or betrayed, or considered herself a victim of molestation. I recall a thousand times wanting to discuss it with her but never found the courage to do so.

I also know there have been many times as an adult I have closed my eyes when I was alone, fantasized about my incredibly beautiful sister and stroked myself to orgasm. I often wondered if she ever did the same thing when she was alone. I found the answer to my questions last weekend.

************************

Two weeks ago, Jessica called and told me she would be passing through my town on a west coast business trip. She asked if I cared if she spent the weekend with us before she returned home. My wife and I were eager for the company since it always seemed family expected us to travel to them for visits. My wife and I readied the guest room and looked forward to Jessica’s visit.

Jess called on Tuesday from Las Vegas and told us she would be arriving in LA on Wednesday evening. We agreed to pick her up at her hotel Friday afternoon.

I hadn’t seen my little sis in a couple years and when my wife and I pulled up in front of her hotel, I almost didn’t recognize her. She looked as beautiful as ever. Her 5’ 3” frame was still incredibly sexy, especially for a woman with children. Her hair was still as dark as I remember and hung to the middle of her shoulder blades. She was dressed in a very attractive black skirt and business blazer with a white shirt underneath. She was the epitome of the sexy corporate business woman, “power-dressed” in a man’s business world. My sister definitely knew how to level the playing field. Her cleavage alone would melt most men.

After loading her bags, the three of us went to dinner to catch up on our lives. We all complained about long work hours, having too many bills, our distain for certain political views in the country and a host of other topics. After dinner, we drove to our house and helped Jessica set up in the guest room. My wife was tired and decided to turn in early. Jessica changed into shorts and a very loose-fitting over-sized sweatshirt as she joined me at the bar separating our kitchen and dining room.

“I need another shot. Whatcha got big brother?” she asked.

I ran down a list of the various alcoholic beverages my wife and I stocked. As tough as ever, Jess settled for shots of Petrone tequila.

“Damn sis, going straight for the hard stuff? I can’t drink that shit!” I said.

“I don’t drink it often but I enjoy it every once in awhile” she replied.

“So, what have you been up to Jess? Everything okay with you?” I asked.

“Yeah, things are good. John’s doing well and Danielle is growing up so fast!” Jessica answered. As she did, she leaned forward to scratch her leg. Wearing the over-sized sweatshirt, I had a perfect view of my sister’s buxom chest.

It had been 20 years since the last time Jess and I had been intimate but in that very instant, I was immediately taken back to the summer of 1986, the last time I held her beautiful breasts in my hand as we made love.

As Jessica sat upright, her eyes met mine. I was still fixated on her chest when I realized she was looking at me. My eyes met hers and I knew I had been caught with a look of lust and embarrassment on my face.

“Douglas! What are you looking at?” she asked with a cute smile on her face.

I quickly turned and grabbed a dish rag from the bar sink and began wiping down the bar, acting as if I didn’t hear her comment. As Jessica downed her shot of tequila, I heard her say under her breath, “Good thing you didn’t notice I’m not wearing panties either!”

I wasn’t sure how to react. I poured myself a shot of Jack Daniels and slammed it back.

“Why so shy Doug? You never used to be so bashful” Jess quipped.

This was the opportunity I’d been waiting two decades for. I drew a deep breath before I spoke, feeling my stomach begin to churn with nervousness.

“Jessica…..um, about when we were younger. Are you…you know, mad at me about it?” I asked.

Jessica looked at me intently as she answered, “Not at all Doug. You never forced me to do anything!”

“But I was older and I’m not sure I should have done the things I did to you!” I replied.

“You regret it Doug?” Jessica asked.

“Part of me does.” I said.

Jessica paused for a moment and then asked, “What about the other part?”

“God, I don’t know hun! I’m afraid to tell you!” I countered.

“Hmmm. Betcha we probably feel the same now as we did then.” As quickly as she answered, Jess stepped around the bar, gave me a kiss on the cheek and said, “I’m off to bed. Body’s still fucked with this jet-lag!”

Puzzled, I replied, “G’night sis! It’s so good to see you! Sweet dreams!”

Before she turned to walk away, Jessica whispered, “I know what I’ll be dreaming about!” With that, I watched her disappear down the hallway to the guest bedroom.

I stood at the bar, my mind swirling with confusion. Had my sister just hinted to me she was still interested in me sexually or was it my lasting perversion reading too much into an innocent comment? Whatever it was, it stirred in my loins as I felt my cock start to swell.

I woke early Saturday morning to see my wife and kids off. My oldest daughter had a cheerleading competition in Van Nuys that would have them gone until late in the evening. As I fixed myself breakfast, I heard Jessica turning on the shower in the guest bathroom. As I ate my breakfast, I continually had to resist the urge to join my sister in the shower. Part of me knew she’d welcome me but another part of me feared she would be pissed at me for assuming we could pick up where we left off years ago.

After I ate, I decided I’d run to the gym for a quick workout. As I walked past the guest bedroom to change into my work-out clothes, I heard Jessica call my name.

From the hallway, it is not possible to see into the guest bathroom. However, Jessica had the door angled in such a manner that she could watch the hallway from the full-length mirror hanging from the door.

“What’s up Jess?” I asked. I pretended to not notice I could see her in the bathroom, wrapped in a large black robe. Her dark hair looked shiny as the light reflected off the wetness.

“You got any plans today?” she asked.

“Was just gonna hit the gym real quick. I need to work out sometime today” I answered.

As I did, Jessica stepped out of the bathroom. “Where’s T (her nickname for my wife Tina) and the kids? They gone already?”

“Yeah. They had to get on the road early. LA traffic is so unpredictable” I answered.

“Well, would you mind if I worked out with you?” Jessica asked.

“No problem hun. I can sign you into the gym as my guest” I replied.

In the next instant, my entire world seemed to move in slow motion. I saw Jessica untie the belt to her thick robe. As she did, her robe fell open exposing a narrow strip of her naked body from her neck down to her pubic region. Jessica stepped forward and let the robe fall from her shoulders.

“I’m not talking about the gym Doug. Work out on me!” Jessica said seductively.

As I stammered to answer, she slowly stepped towards me. “Are you sure hun?” I asked although the answer to my question was quite obvious. I seriously doubt my sister would approach me naked if she wasn’t sure what she was doing or saying.

“I’ve missed you so much Doug and I’ve thought about this moment for so many years” Jessica said, her voice sounding almost as if she was pleading with me.

Jessica was now standing in front of me. She was more beautiful than I remembered. Standing next to me, she seemed so tiny. I am only 5’ 6” tall and weigh a very muscular 185lbs but her tiny frame looked so much smaller than I recollected. As my sister stood naked in front of me, I could not help but notice her long, stiff nipples as they pierced the air. My mind flashed back to years earlier when I used to suckle her breasts in my mouth, teasing her sensitive nipples for as long as she’d let me. Without saying a word, I took her face in my hands and placed my lips against hers. My body trembled as we kissed passionately. Her tongue was so soft as she opened her mouth against mine. For a few seconds, I wasn’t sure if I was 18, kissing my 16 year old sister or was the grown 38 year old man kissing his now married 36 year old sister.

My heart pounded as we kissed. Twenty years of lust, desire, and fantasies of renewed incest with my sister were coming to fruition and my mind raced through memories of her as a young girl.

Jessica pressed her body against mine as we embraced. My hands slowly began caressing her, each hand moving down her beautifully toned arms. As I reached her forearm, Jessica slowly guided my hand across her stomach.

Taking her cue, I ran my hand across her flat stomach. Her skin felt so soft, as soft as it did the first time we had sinned together. Jessica breathed hard as my hand slowly inched downward. Unable to speak as our mouths were still engaged in a passionate dance, Jessica mumbled, “Mmmm hmmm!”

My hand inched down farther until I came in contact with her thick dark mound. It was evident Jessica still took pride in her body as her patch was nicely trimmed in a sexy triangle of closely sheared pubic hair. Jessica pressed her hips against my hand as I gently squeezed her mound, teasing her womanhood. Jessica removed her lips from mine, “We need to get you out of these” she said as she already pulling my shorts down. As my sister worked my shorts over my fully erect cock and down my hips, I pulled my t-shirt over my head and dropped it on the floor next to us.

“That’s better!” Jessica said smiling. “I’ve missed feeling you touch me Doug. Nobody touches me the way you used to!” I opened my mouth to speak but Jessica put her index finger over my lips before I spoke. “Shhh. Let me finish.” I paused, my hand still delicately massaging my sisters beautiful cunt, feeling her full lips between my thick fingers as her tiny hairs tickled the palm of my hand.

“Doug, nobody has ever made me feel like you used to. You made me feel so loved, so sexy, so dirty, so erotic….just, you made me feel incredible! I’ve missed that and want it one more time.” Jessica said. She continued, “If this is the last time we ever do anything, that’s fine but I need it!”

“Me too hunni. I’ve dreamed about this for so long!” I assured my sister.

“In that case…” she said as she slowly dropped to her knees, “let me show you how much I missed you.”

As the last word parted her lips, Jessica placed the tip of my throbbing cock against her tongue and licked the head of my cock, pulling a large drop of pre-cum into her mouth. I watched her swallow my moisture as she looked up at me and said, “Fuck, you still taste so good Doug!”

My cock twitched hard hearing my sister say my name while grasping my shaft with her slender fingers. As Jessica knelt before me, I cupped her left breast in my hand and began playing with her, teasing her sensitive nipple like I did when we were kids. My touch still caused the same reaction as I saw tiny goose bumps appear on her chest and arms.

Jessica opened her mouth as she leaned forward, allowing my cock to enter her mouth. I felt her warm tongue caress the bottom of my cock before she closed her mouth around me. I had forgotten how warm and wonderful the haven of my little sisters mouth felt around my shaft. I felt my legs weaken as Jessica sucked my cock. As a kid, she wasn’t able to take my full 8” into her mouth. It was obvious she’d been practicing over the years as she easily took me deep inside, her lips pressed against the base of my shaft.

As Jessica pulled her head back, our mixture of saliva and pre-cum coated my cock. My hips began to rock back and forth as my little sister devoured my length. As I did, Jessica placed her hands around my hips and gripped my ass, her long fingernails pressed against my skin just inside the crack of my ass. Using her grip, Jessica began to push and pull on me as her head bobbed back and forth. The feeling was overwhelming and I wanted to explode in her mouth.

Not wanting to embarrass myself in front of my sister by shooting my load within five minutes, I pulled away. Jessica let out a cute whimper and pretended to pout as I pulled away from her lips.

“My turn…gimme that sweet pussy hun!” I said.

Jessica rose and stepped back, laying herself back onto the bed. As she did, she bent her legs with her knees in the air, her feet only inches from the back of her thighs. As she had done so many times as a child, Jessica opened her luscious legs, exposing her delicious cunt to me.

“C’mon big brother!” Jessica said as she teasingly rubbed her clit back and forth.

I stepped forward and knelt in front of Jessica. I felt my hands shake as I anticipated the reunion with the first pussy I’d ever tasted. I leaned forward, gently kissing my sisters thighs as I worked myself inward.

Her legs were firm and muscular, yet they retained a feminine allure and shape. I could smell the aroma of her body wash and sweet pussy as I drew closer. I placed my hands inside Jessica’s thighs and moved up towards her sweet cunt. Using my fingers, I spread my sister’s pussy wide and slowly traced my tongue along the shiny pink skin of her full pussy lips. Jess shuddered as I teased her. Her taste was enthralling; sweet, warm, and sinful.

As I ran my tongue around Jessica’s cunt, I began to rub her swollen clit with my finger. As a teenager, Jessica used to squirm back and forth as I pressed her clit down and rubbed back and forth. Twenty years later, it had the same effect. Pushing my tongue inside her tight pussy ring, Jessica wiggled her hips back and forth. As I assaulted her pussy, my mind raced, wondering how many cocks had been inside my sister since I last tasted her. I felt a pang of jealousy as I imagined various men pounding her tight cunt but also found the visions intensely arousing. Those men learned what I already knew; my sister had a hot little cunt.

Opening my mouth, I did my best to cover Jessica’s pussy. Alternating between her clit and tight hole, I did my best to make love to my sister with my wanting mouth. My cock throbbed as I performed this taboo act.

Jessica began to rock back and forth. I knew she was working herself to an intense orgasm. I moved my hands under her legs and placed them on her butt. As I continued to fuck her cunt with my tongue, I lifted Jessica’s hips off the bed, improving my access to her. Seizing the opportunity, I shoved my tongue as deep as I could inside her.

Her pussy was warm and soft. Her hips bucked wildly as my tongue darted in and out. I resumed my assault of her swollen clit. My tongue was becoming numb as I tasted as much of her sweetness as I could. Jessica’s body shook violently as she came. She squealed with excitement as a wave of erotic pleasure and sin-filled ecsatcy flooded her entire body. As she did, I plunged two fingers inside her tight cunt and began to finger-fuck my little sister.

“Fuck, yes Doug! Deeper, deeper, yes, yes, yes, YES!” she screamed. My fingers were soaked as they dove in and out of my sister. I could hear the erotic sound of her pussy juices swishing as my hand continued to work.

Jessica was now moving her hips up and down as my fingers teased her cunt. As her hips rose, I could see her stomach muscles stretch and tighten and her full breasts sway gently as her body moved. Her nipples continued to stand firm, burning a sensually erotic memory into my mind.

“Doug, fuck me please” she begged. “Gimme your cock, please.”

“You want your big brother to fuck you Jessica?” I asked teasingly.

“Yes” she answered with a voice that made her sound like she was 13 years old again.

“Roll over hunni.” I commanded.

Jessica complied, rolling onto her stomach. As she did, she let her feet settle to the floor. Her body flat against the mattress. Jessica looked so beautiful as her legs flexed supporting her weight. Her perfectly round ass stood invitingly in the air as she turned her head and looked back at me.

I stepped forward and placed my cock into her tiny slit. As my cock touched her, I almost came. As I looked at her beautiful cunt, I remembered the first time I saw her naked. Her pussy was completely bald and smooth, with just two wide lips and a deep slit down the middle. As she grew, I watched it grow from a little girl’s vagina to a sexy teenaged pussy and now, a beautiful woman’s cunt!

I pressed the tip of my prick farther between her slit and watched as her pussy lips began to spread around my cock. “Mmmmm, ram it in me Doug” she begged. “I like it rough and hard now! Don’t be gentle with me big brother” she continued.

“Good, me too. I’m sick of fucking women who want it soft and slow!” I answered. As I did, I grabbed my sister’s hips and slammed my cock deep inside. Jessica screamed loudly. If someone had heard it, they might have thought someone was in danger but I knew my sister; that was a scream of lust and pleasure.

“Fuck Doug! I’ve missed you inside me. OH GOD! FUCK ME DOUG, FUCK ME!” Jessica screamed.

Our bodies began to move in perfect rhythm. Perhaps that is what I loved so much about fucking my sister; we shared a bond and knew how to please each other without having to ask. I slammed into Jessica harder and harder. My skin smacked loudly against hers, almost as if making a cracking sound like the snap of a bull-whip.

Each time I buried my cock to the hilt, Jessica would scream “Uhn,” “Uhn,” Uhn.” Her tight pussy was drenched and I could feel her wetness soaking my balls as they smacked her clit with each stroke. Sensing she wanted it harder, I pushed Jessica flat against the bed and used my feet to push her legs together. Once they were closed, I put my legs outside hers and grabbed Jessica by the wrists. Pulling her arms behind her, I maintained my grip on her wrists as I violently slammed my cock into her tight cunt.

Tracy was screaming in ecstasy as I punished her pussy. “FUCK DOUG, YES, YES, YES….GEEEZUS, YES, UHN, UHN, UHHHHHNNN, OOOOOOOOOH, YES” she screamed as she exploded in another earth-shattering orgasm.

Twenty years of fantasy, memories, desire, lust, love, and passion were built up inside and in an instant, my cock was exploding inside my sister. Wave after wave of my hot cum streamed against her cervix and coated her insides. Jessica felt my cock expanding as I filled her with the results of our incest. Once again, my seed was filling my baby sister. Jessica continued to scream, her voice now becoming hoarse. My cock continued to throb inside her as I stood motionless, my dick ultra-sensitive to the slightest movement.

“Guess what time it is baby?” I said. Jessica knew. As I withdrew my still pulsing cock from her tight twat and laid flat on the bed beside her, Jessica began to move herself into position.

Crawling on top of me, she slowly worked her way forward until her gaping cunt was directly over my face. I could smell the scent of our activities, our wonderful juices and sweat mixed together.

Jessica lowered her hips down and pressed her pussy against my mouth. As she did, I opened my mouth and covered her entire cunt. Sliding my tongue inside my sister, I sucked on her as hard as I could. Jessica rotated and ground her hips into my face as I felt my cum and her juices dripping into my mouth.

Satisfied she had let as much of my salty cum drip into my mouth, Jessica bent down and kissed me. As she did, we slowly transferred my cum from my tongue to hers. Jessica smiled as she swallowed. Lovingly, she licked my mouth clean before kissing me passionately.
I put my arms around her and held her close to me as she spoke, “I love you so much Doug. Thank you so much for that. Twenty-fucking-years I waited for that!”

“Mmmmm….no! Thank you hun. God, you’re more incredible now sis!” I answered.

Jessica lowered her head against my chest and we both lay still for a few moments.

My eyes were closed when I felt Jessica stir. As I opened my eyes, I could see a familiar devilish look on her face. As she spoke, Jessica held a bottle of KY Lubricant in front of my face. “Ummm….big brother” she said devilishly, “my ass needs a good pounding!”

This was going to be an awesome weekend!
92 comments

Anonymous readerReport

2014-08-09 22:25:56
ruined by the cheating if they both were single it would have been good but as is it is a piece of shit.

anonymous readerReport

2013-03-03 11:26:07
Short, sweet, to the point, FREE-exactly as ifnomatrion should be!

anonymous readerReport

2012-08-23 13:22:43
if he had any love at all for his wife he would not cheat on her. you totally ruined the story and need to delete the trash NOW!!!

anonymous readerReport

2011-08-28 17:20:37
earlds@earthlink.net

anonymous readerReport

2011-06-27 22:33:10
Wow, this is in every repscet what I needed to know.

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