My Sisters Best Friend. [FM]

This is the story of Jessica, or rather Jess, as she preferred to be called.

To the best of my ability, I’ve attempted to ensure that this story is accurate, however it occurred years ago, and my memory is somewhat rusty.

Jess was a long-time childhood friend, although more accurately she was initially my sisters childhood friend. She was two years older than me, the same age as my sister, and together they attended the same highschool.

Jess was always particularly free spirited, playful, and seemingly always full of light and life. From the moment my sister first befriended Jess (or perhaps it was the other way around), and when I first met her, I found myself enthralled by her whenever I was in her presence. There was something simultaneously intense, and carefree about her. I think it was her eyes, and her boldness that fed the impression of intensity – her eyes were striking, large, and animated. I often found myself getting lost in them, staring, even. But her attitude to life was refreshing, and invigorating. She had such a thirst for life, for knowledge, for experiences. It was irresistible to me.

As I cannot find words to correctly express how I felt about her eyes, I can only compare them to a particularly famous pair – those of Liesl in “The Sound of Music” (actress Charmain Carr), who altogether looked rather a lot like Jess.

I often tagged along with my sister and her friends when they went to the beach (which was fairly a frequent occurrence, as we lived only 20 minutes away) – I think my mother liked having an excuse to get her recluse of a son out into the sun. I have many fond memories taking the two-seater kayak out with Jess, enjoying the way the Australian sun heated her almost translucent, alabaster skin, which was always well coated in sunblock (applied lovingly by me, when possible). She would arch her head back, soaking up the warming rays, and relax whilst I paddled us down the local lagoon. Her hair was a lovely, luscious brown, her figure tall, lithe and slender. Even when I was young, I adored her. I can’t say when that adoration changed into attraction, but at some point, I stopped seeing her as my sisters friend, and started seeing her very clearly as “my crush”.

Over the years, most likely due to her flirtatious, free-spirited nature, that attraction grew, and to my great surprise she was reciprocating. The attraction, to my astonishment, was mutual. We’d message on MSN endlessly, staying up til ungodly hours, early in the morning, discussing everything we could think of, philosophy, religion, the future. That last one was a popular topic, it came up often. And eventually, we added a new topic, that would soon eclipse all the others:

Sex.

We started to trade stories – what we wanted to do to each other. They were clumsy stories, the stories of two inexperienced teens infatuated with one another, and incapable of doing anything about it. No matter how many colourful ways I described how I’d bend her over and ravage her, or sweetly meld our bodies into one, entangling our limbs in silken sheets, we knew we’d never get a chance. My sister was a looming spectre, and ever-present reminder that she was off-limits.

Back then, at the peak of my hormonal rages, sex was all that was on my mind, and as a result, Jess was constantly on my mind too. I’d imagine her silky smooth, milk pale skin, her rosy nipples, her piercing, hypnotic eyes. I’d imagine her curves, her wetness. She consumed me, and my thoughts. And so every night, we’d write new stories for one another, and then she’d call me over skype so I could hear her moan and writhe in her sheets as she read my latest instalment in our imaginary romance. We continued like this for a year, at least.

Jess had always known what she wanted, always known how to get it. Her sexuality, even when we were young, was just as intimidatingly intense as those eyes of hers, and she was always wanting more.

During that year, every time we met up, my sister and the rest of her group of friends was there, watching every move, noticing nothing of our secretive glances, our hidden smiles, our inside jokes and our endless excuses to be alone. But nothing really happened, with so many witnesses. Sometimes at the beach I’d find an excuse to run a hand along her bodice, whilst being batted around by the waves, or I’d get a chance to kiss her on the kayak, far from prying eyes.

Then one day, my sister decided to have a movie night, a sleepover, with her whole group. All in all, I think there were 5, with my sister included. And as they all knew me, and I was friendly with all of them, I comfortably sat down and joined in. Jess sat beside me on the lounge, and I drew a blanket over us. Everyone else was doing the same, as we always did on movie nights. She placed a pillow over my lap, and laid down across it, her head above the blankets, her body concealed below. For reasons I cannot fathom, no one found this strange. I suppose either they had learnt to accept that Jess was comfortable with me, or otherwise were simply oblivious to the benefits of our positioning.

At long last, I had a chance to explore every delectable, delicious inch of her body. We had to move slowly, to avoid being noticed by any wandering eyes. Even with all the lights in the house turned off, the light from the television illuminated just enough so that any large movements would be noticed. I was gentle and cautious in my explorations, slow and delicate were my fingertips as they glided over the mountain and valleys of her skin. I traced her collar bones, the contours of her breasts, small but firm, and down all the way to her waistband. I didn’t hesitate, I had no need. I knew she wanted this, craved it just as much as me by the craziness in those intense, brilliant eyes of hers as she turned her head sightly to look up at me. I felt as though her eyes were glowing with internal illumination, little lighthouses of startling brightness, and that everyone could see the way she was looking at me. But no one saw a thing.

I let my hands run free over her ivory silken body, drawing imperceptible ripples of pleasure from her as I teased at her rose pink nipples, turning her breathing heavier, raspier as she struggled to maintain her composure, til I found the hem of her panties, and dove my fingertips under them, onto her trimmed pubic mound, before settling my index finger on her clit, where it remained, moving nearly imperceptibly, in slow, lazy arcs, steadily building pressure for the rest of the movie, and the one after that.

That night, I could not sleep. What man could, after such an experience? Every noise was amplified a million times, every noise was oppressive and extreme, as I willed her to walk down the corridor from my sisters’ room and enter my room. But alas, she didn’t. I woke to find a message on my phone, that one of the girls had only fallen asleep at 3am, and she’d had no chance to make her escape. Her disappointment was palpable as we had breakfast, though only I perceived it.

The frequency and intensity of our messaging reached a peak, after that. Many nights we’d stay up talking til the fiery dawn light broke over the hills, and sifted through the rustling gumtrees, and the lorikeets and galahs greeted us with their songs and screeches. If I was an eager, horny teen, then Jess took it to a whole new level. Morning would come and still she would beg for me to write another page, another story, and her fingers worked away between her legs, and she would divulge her deepest desires and fantasies, asking me to fulfil them with flowery words. I have many fond memories of watching day break as I heard her sweet voice, her ragged moans.

Then, for a period, for whatever reason, we each went our own ways, finding ourselves in a series of short-lived relationships. But like all good things, they came to an end, but not without a silver lining. Both of us gained valuable experience, which I intended to put to good use.

By the time I was late in my 18th year, and she was 20, Jess was an absolute picture of perfection. Her curves had filled since the last time I’d seen her, her hips were wide, her waist narrow, her form was more womanly than girlish. Her eyes remained as indescribable as ever, startling in their intensity and beauty. I was intoxicated by her, and when she walked through the door, I was struck by how strongly I felt for her, reliving every memory of our past as I saw her. In the time that had passed since our last sleepover, I’d been so distracted with other girls, lesser girls, that I’d all but forgotten of Jess, until I opened the door to greet her and felt the gears turn in my mind, the old memories resurface.

Everyone settled back into old routines, and once again I found myself with Jess’s warm, slender form sprawled over me, her legs curled up on the lounge, her body tucked under the blanket, her head on a pillow in my lap, her back against my side. And once again my hands found their way into her clothing, where they explored her hungrily. I discovered she was wearing a bra which zipped at the front, which both fascinated and frustrated me, as I could not silently undo it, and had to be satisfied with simply exploring under the cups of her bra. Her breasts were smooth, soft mounds, not too small nor too large, probably a C cup. Her nipples, so perfectly sized, hardening under my fingertips, drove me wild. I probably spent the whole first movie just enjoying her lovely breasts, circling her nipples with my fingertips, gently twisting them, hardening them, sometimes running my fingers as light as I could over them just to enjoy the reaction. She was incredibly sensitive, and oh so lovely.

Eventually, I traced down along her sternum, to her belly, which was flat and smooth and lovely, and down to her pants, which she had already unbuttoned – without me noticing, or asking. My hand found its favourite place again, this time encountering very little hair – what remained was only a small, trimmed triangle. Her wetness was encouraging, and her slick, hot slit begged to be touched. I extended a finger down to her opening, and inserted just the tip – extracting a low, rumbling moan from her, but more importantly, covering my finger with her slick, sweet juices. I returned to her clit, circling it, teasing it, until every contact no matter how miniscule had her squirming, and I ceased my torturous ministrations, as I was afraid we’d be caught.

In lieu of her sensitive clit, I lowered my hand, and my fingers found their way inside of her. The soft, hot folds of her wetness enveloped me, as I made small circular motions with the pads of my fingertips inside her. We were both in heaven, our smiles totally inappropriate to the horror movies selected for Halloween movie night. Hey eyes were glazed over, their intensity veiled behind contentment, edged with desire. Her pale skin glowed in the moonlight, and her dark hair was strewn over her face, which was coated in a thin film of sweat. I worked my fingers inside of her like the piston of a steam engine, whilst she struggled to maintain steady breathing and composure, keen to avoid the notice of the other girls in the room.

We were the last to leave the living room and head to our respective rooms after the movie ended. I stole a risky kiss from her as we mounted the stairs and headed to bed.

Once again, sleep escaped me. I was full of nervous energy, and bubbling with expectation. This time, everything went according to plan. The girls were asleep soundly, all except one, who at 1am snuck away “to the bathroom”, which was adjacent to my room, all the way down the hallway. She took the wrong door – and entered my room. With the delicate motions of a flower bending to the wind, she closed the door behind her silently and smoothly, then sauntered over to my bed in the moonlit dark, a lithe, elegant feline walk, full of grace and confidence.

Her first words as she approached me were complaints of how loudly the wooden hallway had creaked as she had made her escape, though to me they were a blessing, each step echoed through the silence and with each gentle tiptoe my anticipation mounted.
I knew she was on birth control, we’d messaged each other ever since finding out she was coming over for another sleepover, and somehow it had seemed like a relevant detail to her. Whilst I’d been distracted with other girls, she’d been doing her own romantic exploration, and had already two notches carved onto her proverbial rifle stock, so I knew I had no need to be overly gentle. Sad as I was that I would not be her first, I was eager to see what she had learned.

She sat on the edge of my bed, and I rose to kiss her, properly this time. I took her face into my hands, running one behind her neck and into her hair, my fingertips massaging her gently as they wove their way into her luscious, dark hair. The kiss started slowly, passionately, as we each tried to weld our faces together, to meld into one being of lust and wetness and desire. I withdrew a hand from the side of her face, and down onto her chest – disappointed to find she was without her zippered bra, which I had been looking forward to undoing. She giggled slightly at my silliness as I pushed her onto the bed, and withdrew my face from hers, and, lifting her shirt off her, planted my lips first on the side of her neck, then down to her lovely rose pink nipples, enjoying the sensation as they hardened in response to my touch.
I gently sucked, nibbled and licked my way around her breasts, each of them left with a film of saliva as I lowered my head further, pulling off her pyjama pants and her panties, determined to use what meagre experience I had to make this a memorable experience for her and so set about burying my face in her hot, sweet pussy, enveloping her clit with my mouth and running circles around it with my tongue. I licked up the entirely of her slit, tasting her exquisite, complex taste, feeling the soft smoothness of her skin on my tongue.

My fingers joined my mouth in their pursuit, and found their way inside of her hot wetness, as I suckled on her clit. I massaged the delicate folds of her tightness, and she arched her back and writhed under my touch, the combined assault of tongue and fingertips driving her to ecstasy.

I pulled myself away from her perfection and began to kiss her again as I lined my manhood up with her slick, searing hot pussy, kissing her eagerly and hungrily. I pushed myself into her, her legs up around my waist, ankles crossed over the small of my back, as I plunged into heaven itself. Now, I’m not the largest man in the world, being only slightly above average in length and girth, but the walls of her lovely pink pussy were tight and accepted me with only the smallest need for persuasion in the form of pulling her hips against me, and I found myself fully encased in her exquisite, wet perfection. I ran a hand up to her perky, picturesque chest, and groped at her soft mounds, using my thumb and forefinger to tease her nipple into a hard spire, as the other hand controlled her hips as we collided in waves of unbridled passion and desire.

After some time had passed with her legs crossed over my back and my cock impaling her deeply and greedily, I flipped her around til she was on all fours, and I could admire her shapely figure from behind. Her ass was round, and as I reached my hands down to her waist, I felt her skin, smooth as silk. Her skin was milky white, and her pink pussy bright and soaking wet as I plunged myself back inside of her, slamming against her ceaselessly as we tried our very best to stifle our moans and control our breathing. I fucked her like a man possessed, drawing on years of unfulfilled desires and secretive, furtive romance for energy as I pushed myself into her sweetness again and again, the encompassing warmth of her tightness filling me with more desire every time I thrust into her.

She looked back at me, hunger in her eyes, pulled me out of herself, then pushed me to the bed, mounting me. She lined up her tight, warm wetness with my engorged cock and began to gyrate her hips, rolling her clit over my skin as the rode me. Her back was arched, her perfect, perky breasts bounces ever so slightly as she moved. The sight was enthralling, intoxicating. I ran mind hands up from her waist, along her taut belly, to those perfect mounds of soft flesh, as she increased in intensity and her breathing became ragged and laboured. I began to thrust back into her thrusts, meeting her with enthusiasm as she worked her body in perfect unison with mine, until I felt that familiar feeling building within me.

I leant upwards, taking a nipple into my mouth and nibbling on it before disengaging with her perfect breast and whispering soft to her that I was about to cum – and asking where she wanted it. In between her ragged, heavy breathing all she said was “cum in me”. Never have I heard sweeter words, nor more eloquently delivered, than those three words gasped between rasping breaths.

I allowed the waves of pleasure to roll over me as I laid back, and resumed thrusting eagerly into her as she rode, my hands on her hips rolling with her motions. As I came, the sensations overwhelmed me like an avalanche, a wave of powerful feelings, both physical and emotional draining me entirely as I filled her with hot cum, and she slowed her riding down, increasing the exaggerated rolling motion of her hips as she wound down, my cum settling inside of her, my dick slowly loosing stiffness.

I rolled her onto her back, and kissed her deeply, my cock still ensconced within her, trying to make the moment last as long as I could. I glanced to the side, and saw it was 3.30am. We had been going for over two hours, and all I wanted was more. I kissed from her sweet lips to the neck, down her collar bone, and finally extracting my spent, soaked manhood, shifted back on the bed, and leant down and took her nipple into my mouth. I ran my tongue in circuitous motions over it, looking up at her gorgeous face, then lowered myself once more.

I could not care less that I had just cum in her, I needed to take her clit into my mouth one last time, and sucked greedily and eagerly on that sensitive nub, enjoying the way she writhed. But soon, she began to push at my shoulder with her hand, and gestured to the clock, and said she had to get back to her room. She seemed flustered, her sense of urgency returning. I dressed her, cum dripping from her pussy into her panties, and she left with a kiss goodbye, back to my sisters’ room.

The next morning, I woke to find the gaggle of girls at breakfast, and Jess too cautious to make eye contact with me, lest a glance would betray her. She messaged me later that week to tell me that she’d just come out of a serious relationship, and that I had made for a good rebound. Regardless, with my sister in the picture, we had no chance at a future together.

My sister never found out, and none of her friends suspected a thing. Our secret was safe, and became a cherished memory I will never allow myself to forget. When I am old, weak, and fragile,
I shall still look back on that night and imagine her perfect form bathed in the blue moonlight, her brilliant eyes staring deep into mine, and those sweet moments we shared.

After that, my sister and Jess drifted apart, as Jess moved and her social circle changed. She explored her sexuality with new people, eager to try new things and live her life to its fullest, and not long after my night with Jess, I started on a series of short-lived, and ultimately unsatisfying relationships, which ended our contact. None the less, she had a profound impact on my life, and started a pattern of older women that persists to this day.

I’ve only seen her once since then, years later, at the wedding of a mutual friend, with her partner of several years. It was a bittersweet reunion, but she seems much the same, as gorgeous and lively as ever.

There are a great many things I regret having done in my life – a great many failures, and many missed opportunities, but few hurt as much or as deeply as having lost enthusiastic, lively, spirited Jess.

That I never attempted to rekindle the dying embers of our past into a relationship as an adult is a great shame, and now she’s been with the same man for upwards of four years, and I doubt I shall ever get that chance.

So as we come to the end of this story, I warn you, dear reader, of the consequences of letting an opportunity pass you by. When the moment comes, grasp it, and do not let it go. You never know what will come of it. Do not squander opportunities due to fear, and anxiety. Life is here to be lived, fully. Do not let those who matter to you fade into mere memories, when they deserve to be so much more.

With much love, and fond memories, S.

Source: reddit.com/r/gonewildstories/comments/87zzio/my_sisters_best_friend_fm