Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click herePrologue
The blond sat on the edge of her bed, a shapely leg crossed over the other, her petite frame wrapped in a white, terry cloth towel. Having just had a shower, her damp locks were strewn about her pretty head. Checking her phone she hoped to see a message, and was slightly dismayed when it wasn't there. Suddenly, a familiar ring tone did sound, but not the one she had wished for.
"Fuck," she mumbled to herself before answering. "Hey."
"What's up?" The girl on the other end of the call replied.
"Not a lot, just hangin' out."
"It must be nice. I'm still stuck at work. Don't know when I'll get off."
"Sucks to be you," the blond said, gently mocking her friend.
"Nice Jess," the other answered sarcastically. "So, how are things going at Casa Watson since your parents left?"
"Same old same old," Jessica said noncommittally.
It wasn't really. Jessica Watson's parents were travelling across Europe for a month. Against their better judgement they had left the twenty year old on her own, with a couple of caveats. For one, there were to be absolutely no parties. Though disappointed, she couldn't really fault them for that. Not after what had happened back in early June. She could only vaguely remember the incident, her recollection clouded from having indulged in weed and a great deal of alcohol on that particular occasion. It had happened shortly after she had completed her sophomore year at university. Her parents had gone away for the weekend; the girl decided that was the perfect opportunity to have a bash to celebrate the end of the school year.
The little she could recall involved hordes of intoxicated college kids, several empty kegs scattered about the yard, one even afloat in the pool, music blasting throughout the neighborhood, and ultimately two police cruisers pulled up in front of the house. The following day she had suffered a brutal hangover, but with the help of a couple of friends she had managed to clean everything up, get the kegs removed, as well as any other incriminating evidence.
Her mother and father returned that evening, and for a few days afterwards were none the wiser, until her dad discovered a dozen empty beer cans and a used condom tucked away in the pool shed. The row that followed was one for the ages, but two months later all seemed to be forgiven, if not forgotten. Along with the aforementioned stipulation about gatherings being off limits, there was one additional requirement.
"And your babysitter, how is that working out?" the other girl inquired, her tone dripping with innuendo.
Jessica hesitated before continuing. Her parents had asked an old family friend, Jake Wilson, to check in on her from time to time, and help out with the upkeep of the property. He had attended high school with both of her parents; in fact he was her father's best friend. Growing up he had been much like an uncle to her, and she had referred to him as such when she was younger. He was affable and charming, with a great sense of humor.
His appearance belied his age, the forty-five year old looking closer to thirty than his actual age. He was fit and strong, the result of an active lifestyle, regular visits to the gym, and just plain old good genetics. Six feet tall, he possessed a full head of wavy, dark hair, some grey speckled across his temples. Subtly handsome, his pale blue eyes sparkled with equal parts intelligence and mischief. Kind and friendly, he and Jessica had gotten along fabulously for as long as she could remember. He had always had a soft spot for her, at least she liked to think so. In her early teens she had had a bit of a school girl's crush on the handsome older man, but then she went to high school and started dating and the school girl crush was all but forgotten...until now.
"Oh it's fine I suppose."
"Yeah, I bet Uncle Jake is taking good care of you," her friend said suggestively.
"Chrissy, that's disgusting."
"Oh gimme me a break Jess, I'm just teasing."
"Well, I don't think of Jake that way, he's really almost like a second father."
"All right I apologize. Hey, I'm off Wednesday. Mind if I come over for a swim?"
"Yeah sure, no problem."
"Awesome, thanks Jess! Anyway, I gotta get back to work."
"All right, talk to you later."
Hanging up, the blond sighed. Reaching across to her night table, her delicate fingers wrapped around a cup of tea. She brought the warm beverage to her glossy pink lips, taking a sip. Her back rested against a pillow propped up against the headboard as she contemplated the conversation she had had with her friend.
She had lied to Chrissy. It was true that for almost her entire life Jessica had never thought of Jake in a sexual way. Sure, there had been that crush, but at fourteen it was puppy love, and she had never considered actually fucking her Uncle Jake. But a discovery seven months ago had shifted her perspective a hundred and eighty degrees. Jessica could remember it like it had happened yesterday, rather than in the early hours of New Year's Day.
**********
Her parents were hosting a New Year's Eve party. Jessica for her part would ring in the new year with a group of her own friends at one of their houses, a guy friend picking her up at ten; she was still around when people began arriving for her parents' gathering. A taxi dropped off Jake and his new flame Melanie. She watched from the top of the staircase as her mom greeted them at the front foyer. After taking their coats, she called out to Jessica to bring them up to one of the spare bedrooms. Reluctantly the girl made her way downstairs.
"Hey Jess," Jake said, smiling warmly.
"Hi Jake," she answered, grinning shyly.
"Hello dear, how are you?" Melanie added, more out of politeness than anything else.
"Hey Mel," Jessica mumbled, sounding none too pleased to see the gorgeous redhead at Jake's side.
After shedding her boots Melanie had slipped on a stylish pair of high heeled sandals, so effortlessly that it barely registered she had done so. Close to six feet tall, she possessed the face of a fashion model, seemingly flawless. Her dark, scarlet tresses were radiant, cascading across sculpted shoulders exposed above a sparkling black cocktail dress clinging to her shapely body. The V neck of the dress did little to hide the woman's magnificent assets, her spectacular bosom a wonder to behold.
Collecting their coats Jessica trudged back upstairs. The girl was truly self assured in her own appearance; she knew she was the ideal combination of sweet and sexy, but in her estimation Melanie was in a whole other league, the only female that Jessica felt inadequate next to. The two had never gotten along. The older woman had endeavored to be friendly at first, understanding how close her husband was to the girl and her parents, but over time she wearied of the charade, seeing Jessica as more of a snotty little brat than the sweetheart that Jake thought she was. The younger girl for her part despised Melanie from the get go, considering her to be a stuck-up bitch. Gorgeous without doubt, but a bitch nonetheless.
Later when she left for her own get together Jessica was feeling out of sorts, somewhat melancholy. She couldn't put her finger on why. The boy taking her was a year older, and they had met back in high school. A few times during the drive she stole glances at him. He was reasonably good looking she thought. They weren't dating and she hadn't been interested in doing so, but Jessica suddenly had the urge to fuck him. At the party she blatantly flirted with him, sharing a rather hot kiss at midnight, then screwing him in his car when he brought her home at 2:00 am. As usual she had been left wanting, the young man cumming way too quickly and not bothering to finish her off. Used to being frustrated she planned on masturbating before falling asleep.
Entering her house it appeared that all the guests had departed. Yawning, Jessica walked quietly into the kitchen, removing a bottle of water from the fridge and taking a long, refreshing draught of the cold liquid. Yawning a second time she suddenly felt sleepy. Returning the half full bottle of water to the refrigerator she made her way to the staircase, planning to head up to her bedroom; a faint noise from the lowest level of her home caught her attention. Moving towards the steps leading down to the TV/Recreation Room she soon realized that what she was hearing were the unmistakable sounds of a couple fornicating.
Jesus Christ mom and dad, you couldn't wait to go to your bedroom to screw, she had thought indignantly, turning to resume her journey to her own room, when a voice froze her in her tracks.
"Yes Jake, fuck me with that fucking cock."
It was Melanie. And Jake. Not her mother and father. What had a moment ago grossed her out had now become completely engrossing. She took a step closer, continuing to listen to the quiet yet clearly discernible goings on.
"Mmmmm, your pussy's fucking tight as hell," Jake grunted gruffly.
The expletive escaping his lips sent a jolt through Jessica, her cunt tingling with the early emanations of growing arousal. She could hear the couple's bodies slapping together, their heavy breathing echoing in her ears; Melanie's high pitched moans and Jake's guttural groans worked in tandem to make her hornier by the second. The dirty talk continued, the young blond captivated.
"Goddam Jake, I love your thick cock."
"Yeah Mel, you love it filling your tight little hole?"
"Ahhhhh fuck yeah...."
"Take my fucking cock deep you gorgeous whore!"
"Oh yes Jake, fuck my cunt hard baby!"
Jessica was flabbergasted, the nasty words rolling from Jake's lips in particular making her head spin. It seemed so completely out of character for the gentle, modest man she had once called uncle. For a moment she considered leaving, but the sound of their flesh pounding in unison kept her in place, her little vagina getting wetter and wetter. Dropping her right hand between her legs, the cute girl slowly caressed herself over the tight jeans she wore. Closing her beautiful blue eyes, she imagined the scene playing out a few scant feet away.
But then it dawned on her: I don't have to imagine it.
Creeping ever so cautiously, the twenty year old tip toed down one step, then another. The room she was nearing was faintly illuminated by two ceiling lights, the stairs leading down blanketed in shadows. Jessica couldn't resist the lure of viewing the illicit act; she didn't dare move closer, and yet she couldn't stop. When the two lovers were finally visible, the girl spying on them was blown away.
Both were completely naked, Melanie's cocktail dress, thong panties, and high heels indiscriminately tossed across the floor. She was bent over the black leather sofa, rocking up and down on her toes. Jake was behind her, methodically cramming his straining member in and out of the redhead's pussy, his powerful buttocks thrusting back and forth, back and forth.
"You beautiful slut, shit I love fucking you," he growled.
"Ohhhhh baby..." Melanie mewled, her hips gyrating as Jake plowed her.
Jessica could feel her juices seeping from her slit, soaking her panties. Deftly unbutton her pants with her right hand while her left massaged her tits over her t-shirt, she slipped her fingers beneath her underwear, two digits strumming her clit. Transfixed by the sight in front of her she slowly masturbated as Jake continued fucking Melanie.
"Holy fucking shit, I wanna cum inside you," he moaned, his pace quickening.
"Fuck baby, not yet, not yet," Melanie cried out softly, desperately.
"Aw fuck bitch..." Jake answered, laughing but slowing down.
The statuesque woman's left hand tightly grasped the back of the sofa, her right disappearing to play with her shiny button. Jake leaned forward, his broad, chiseled chest pressed firmly against Melanie's back, his cock embedded inside her. Jessica saw his right hand reach around to join his girlfriend's, both now partnering to attack her clitoris. His lips nuzzled her slender neck, kissing his way to her earlobe, then whispering something inaudible in her ear, a tiny smile spreading across the woman's face.
What did you tell her? Jessica wondered.
She couldn't help but be jealous, wishing that she was the recipient of Jake's whispered sweet nothings. Her jeans and panties now half way down her legs, the little blond kneaded her blossoming labia, the tender petals sandwiched betwixt her index and middle fingers; she slid one inside, the creamy concoction within swirling around the digit.
Jake had straightened up, his strong hands gripping Melanie's slim waist, his lower body oscilating in and out. The woman's eyes were closed, her head now laying on the back rest of the couch. Jessica could see her massive breasts quaking beautifully as her beau fucked her. Apparently able to defy gravity, they maintained their awe inspiring firmness and shape while dangling from her body.
Jessica's t-shirt was now pulled up and her bra pulled down, the fingers of her left hand alternating from one tit to the other, cupping them, squeezing them, tweaking and twisting her swollen pink nipples. Her boobs were mere grapefruits relative to the other woman's majestic melons, but the younger hottie was quite enamored with them; they sat up proudly on her chest, shapely and soft yet firm as well, as only a twenty year old's could be.
Adding a second finger, she delved the depths of her tight, squelching hole, her thumb brushing her clit. An orgasm was fast approaching, milky ejaculate streaming down her inner thigh. Jessica saw Jake quicken his pace, hammering Melanie's pussy with his impressive tool, and based on the dewy trickle dribbling down the other woman's leg, her body language, and the vulgarities spewing from her mouth, she knew that the redhead was seconds away from cumming herself.
"Jesus Christ Jake, I'm so fucking close, go baby, go!" she exhorted, her fingers loudly slapping her clit.
Grunting wordlessly the forty-five year old stud-muffin complied, screwing her for all he was worth, like a crazed automaton run amok. His hands tore into Melanie's tits, mauling them as his pelvis pounded her ass over and over and over until they both came together at last.
"FUCK JAKE, FFFFFFUUUUUCK!!!"
"UUUUUUHHHHHHHHHHH!!!!
Jessica clamped her left palm over her lips, stifling a scream that would have surely given her away. The beautiful, perversely erotic tableau of Melanie's and Jake's climaxes had triggered her own, a paroxysm of insane pleasure rippling through her nubile body. Her legs had turned to jelly, much as the ruby haired goddess's had, both women's lower extremities trembling, the two mirroring each other as they pressed their limbs together.
Jake for his part had made a final frantic push forward as his dick exploded, moaning for several moments as his genitals pumped a deluge of spunk inside his lover's womb. The two then slowly collapsed to the carpeted floor, the older man lovingly cradling his thirty-eight year old partner's exhausted body, his lips tenderly kissing her neck, his right hand gently stroking her hip.
Jessica surreptitiously straightened up, having no desire to observe this post coital cuddling. She carefully and quietly pulled up her pants and lowered her shirt, then silently padded back up to the main floor. Arriving at the staircase she took her time climbing the steps, cautiously making her way to her bedroom. Slumping onto her mattress she soon lost consciousness, so overwhelmed by what had transpired that she failed to even undress before falling asleep.
*********
The mental image of the tryst burned into her psyche, Jessica found herself constantly thinking about it, replaying the sordid scene over and over again over the following months. The shock of discovering that her dad's best friend was a goddam fuck machine caused her to change her behavior around him. Initially following the revelation she had difficulty looking him in the eye and would get flustered if he just said hello, but that eventually was replaced by something else: the express desire to experience the carnal delights of her Uncle Jake for herself.
Abandoning her shy ways around him, she had started flirting whenever she got the chance. It wasn't over the top, and could easily be mistaken for friendly banter, but she made a point of hinting ever so subtly at what she desired. And over the last few weeks she had come on even stronger. Jake had been oblivious at first; slowly but surely however she had gotten her message across, his resolve close to crumbling. A vid she sent him, well that had to finally push him over the edge she thought. Sweet little Jessica hoped she would soon enjoy what her Uncle Jake had to offer.
Chapter 1
Jake Wilson ran his hands across his face, rubbing his eyes, then his stubbled chin. Stretching his arms languorously above his head then out to his sides, his left fell flat against the cool silk sheet covering the king sized mattress on which he lay. It felt odd, almost disconcerting to have the entire bed to himself. It was a rare occurrence, especially over the last ten months or so. Turning onto his side he gazed briefly at the empty space beside him, unoccupied for the last twenty-one nights.
Never one to linger too long in bed, Jake pivoted his legs off the side of the mattress, the silk bedsheet flowing from his body. Dropping to the floor he pumped out forty pushups, then continued with light calisthenics for another twenty minutes. This or yoga were a regular feature of his morning routine. His girlfriend had gotten him into the latter, the older man initially skeptical but soon realizing the tangible benefits.
Following the exercise he sauntered into the bathroom, first standing over the toilet, fishing out his cock from the black cotton boxers he wore. In short order a strong stream of golden piss flowed from his bladder, Jake reveling in the release. After a few cursory jiggles his long dick was back inside his underwear. Moving to the basin he washed his hands, the scented hand soap reminding him of Melanie.
Peering into the mirror, for a moment Jake fancied that his reflection stared back at him accusingly, as if his subconscious knew something he didn't. He blinked and the expression changed, a sardonic smirk now on his face. Reaching into a drawer he withdrew a razor and shave gel. Splashing his face with hot water he lathered up, then quickly shaved. Next he brushed his teeth and flossed, concluding with a thorough rinse of minty mouthwash.
Before entering the walk-in shower he reached for the faucet. Preferring quick showers he would usually keep the water cool, a bracing blast of cold liquid pelting against his skin helped motivate him to that end. This morning however he had set the temperature to hot. Lowering his boxers he stepped out of them, kicking them aside, then slipped his muscular, nude form into the steaming enclave, closing the glass door behind him.
At first the heat of the water caught him off guard, being so accustomed to the opposite, but he quickly adapted to the change, the cascading spray soothing and sensual. For several seconds he let it inundate his face, his eyes closed, his mind drifting. Jake hadn't had sex now for the longest stretch he could remember, three weeks that felt like an eternity.
On the surface one would never guess the extent of the unassuming man's promiscuity. Though attractive, his looks alone wouldn't lead one to surmise his secret. Kind and modest, at times even striking some as shy, he certainly didn't come across as any kind of Don Juan. Nevertheless, he had a quiet charm and confidence that was often irresistible. An erotic enigma, once he got a woman into the sack it was game over, the humble man morphing into a sexual titan. Over the course of his lifetime he had honed his skills to the extent that the females he bedded were always left completely satisfied and craving more.