The Spanking of Widow Conway Ch. 02

Half asleep himself, with a million different things roaring through his head, Jess Tuttle didn't hear Helen's light footsteps until she was literally less than three feet behind him.

"AAAHHH,' he let out a gasp when he turned and saw the petite older woman standing there.

"Everything OK, Helen?" Jess asked.

"Oh Yeah...just having a hard time falling asleep...heard you were still up...and...I thought I heard Trina crying...is she OK?" she sighed.

"Yeah...yeah," Jess nodded. "She goes through bouts like that a few times a week since things started going squirrely around here. Most of the time she falls right to sleep after I go up and tuck her back in."

"Good," Helen replied as the two made their way to the kitchen.

Standing in front of Helen, shirtless with nothing on but a pair of flannel pajama pants, Jess suddenly felt very exposed as silence hung in the air between them.

"Got some milk in the fridge ...if you think that will calm..." Jess started to offer before the blank expression on Helen's face caused his lips to go numb.

The next few seconds were such a blur for Jess, it would take years for him to truly sort everything out.

Jess could feel Helen's thin, frail arms warp around his back with surprising strength. Instinctively putting his own arms around the older woman with tentative care, Jess just stood there for several moments, not knowing quite what to think. Feeling Helen bury the side of her head against his bare chest, Jess could feel the carnal energy seeping from Helen's pores.

Part of him was frightened by her sudden and inexplicable display, but the intensity she was gripping him with made pulling away increasingly difficult. The longer he stood there allowing the primal part of his brain to take over however, the easier it was for Jess to see things had been building to this for awhile. The fact that there was so much difference between the two, from an age standpoint among other things, it couldn't negate the simple truth that there was shared need they'd somehow tapped into with each other.

Tightening his grip around Helen once he made that realization, the two stood in the center of the kitchen, sharing an extended embrace until Jess finally raised his hands to each side of Helen's head and tilted her gaze towards him. Placing his lips softly down on top of her's, Jess could feel the older woman's torso start to melt against him.

Jess' senses were instantly tweaked when Helen raised her hands and placed them on each side of his face as he kissed her. Even though he was young, Jess knew exactly what Helen had been up to before following him down the stairs from the unmistakable scent permeating her fingers. The fog of arousal now thick inside Jess' own head, he gave up trying to process the gravity of it all and simply allowed the beauty of what was happening to prevail.

Reaching up with his left hand, Jess closed it around the wrist of Helen's right. Easing the shivering woman's fingers apart, Jess pulled them towards his mouth before swirling and sucking the musky sheen of vaginal froth slowly from each digit.

"UUUHH...AAAHH," the 65 year old woman quaked and quivered, a look of stunned awe now plastered across her face as Jess seductively cleansed her fingers.

Nudging Helen slowly backwards, Jess eventually pinned the much smaller woman against the far wall of the kitchen as he kissed her relentlessly on the neck and chest.

An audible, "OOHHH", bubbled from Helen's throat the instant she collapsed flat against the wall.

Pulling away at some point to gauge Helen's reaction, Jess watched her chest rise and fall as a look of uncertainty and expectation bloomed in her sleepy eyes. Diving forward, Jess clamped his lips down on the front of Helen's neck and kissed her with reckless abandon as she squirmed between him and the wall. Feeling Helen's hands digging roughly at his shoulders for support, Jess could hear the gasps of lust leaving Helen's throat and bouncing around the room.

It didn't take long before Jess snuck his right hand under the night shirt Helen had borrowed from his Wife. Sliding his hand steadily up the smoothness of Helen's warm belly, Jess didn't hesitate at all before squeezing his grip around Helen's left breast.

"WWWAAA...WWAAAHHH," she trembled, immediately rutting her forehead against Jess' left collarbone as he fondled her small, fleshy orb.

Curling her feet around the back of Jess' calves until she was essentially sandwiched there, Helen flailed her hands up to the top of Jess' head and clawed anxiously at his scalp as he felt her up.

Jess knew he could take Helen right there in the kitchen if he wanted, but felt an overriding pull to take her up to his bedroom and make love to her on the comfort and space of his marital bed. Removing his lips from Helen's tingling flesh, Jess' eyes locked onto hers communicating his silent suggestion for the two to go upstairs.

"...N...No...," Helen uncoiled her vocal chords and managed to say.

"I...MMMM...Uhh...Let's...go...downstairs... to the basement...," she added with the scant amount of breath remaining in her lungs.

Somehow understanding the implication of the older woman's plea, Jess nodded in agreement then scooped the tiny woman up in his arms and carried her down the basement steps, much the same way a groom would his young blushing bride.

_________________________

Despite the pitch black darkness of the basement, not to mention her own spotty eye sight, Helen could still see the milky white outlines of her legs spread wide as she laid backwards on the edge of Jess Tuttle's bed. What she couldn't see as she gulped for air, but could undeniably feel, was the presence of the young man's face buried against her steaming vagina.

The darkness in a way was a blessing, creating the perfect backdrop for the slivers of light that exploded inside her head each time Jess flipped and swirled his tongue across her burning labia.

It was a delicacy Helen had only experienced a precious few times in the past. Her Husband had been the only man she'd ever gone that far with, and he'd only gone down on her a handful of times over the years, mainly when they'd been much younger and willing to experiment.

That's not to say Helen hadn't used a multitude of objects and contraptions down there to compensate, but nothing on Earth compared to the sensation of another person's mouth chewing hungrily on her swollen vulva. Her hands pressed tightly against the back of Jess' bobbing head, Helen spread her pale feet high in the air, feeling her entire body quivering like Jell-o as she whimpered on Jess' makeshift mattress.

The cloak of darkness also provided Helen with enough plausible deniability that she didn't have to vividly see Jess doing what he was doing, knowing the ramifications certain to come when she had to face him during the light of day.

"How are you ever going to look at him in school?" the rational part of her brain wanted to scream but was dutifully shouted down by the synapses popping like kettle-corn inside her head.

His mouth clamped like a human leech over the buttery expanse of Helen's vagina, Jess gripped his hands tight along the insides of the her thighs until there was no way she could have eradicated herself, even if she'd wanted. All that was left now was to allow Jess to have his unfettered way with her.

The moist sounds of Jess dining between her legs filling the darkness between her intermittent gasps, Helen found herself corkscrewing to the left, then back to the right each time Jess shifted the knifing angle of his tongue across her screaming fissure.

Gently grinding all ten of her fingertips into the 28 year old's scalp, Helen suddenly found her rear-end humping off the bed, in essence fucking Jess' face with her spasming cunt as she lowered her legs and wrapped them like a vine around his back.

The decision to go downstairs instead of up to the bedroom paid immediate dividends when Helen began to cum. Two floors away from the sleeping children, behind the closed basement door, Helen's release bled forth in full throat. Her heels dug into the muscles of Jess' back, Helen franticly twisted side to side, her thighs enveloping Jess' head until it gave the appearance that his entire upper body had been swallowed up by the mouth of a shark.

"GAAWWWDDD...GGAAWWWDDDDDD...GGAAWWDDDDDD," Helen cries rose and fell for nearly 30 seconds like a runaway roller coaster until she'd saturated Jess' face with her slick feminine spray.

It took several minutes for Helen's orgasmic tremors to run their course, but Jess stayed in place the whole time, patiently perched on his knees swabbing his lips and tongue over every square inch of the older woman's vagina until her intertwined legs finally went limp and dropped with twin thuds to each side of his shoulders.

Standing up along the edge of the mattress as Helen sighed and shuddered below, Jess edged his thumbs into the waistband of his flannel pants and tugged them down to the floor, leaving him completely naked as he hovered above her.

Helen Conway's pussy was throbbing in glorious agony. Not exactly well practiced with her sexual endurance, after cumming twice in the previous hour, she felt as if she'd literally explode if so much as a gnat landed between her legs at that moment. Seeing Jess' rugged outline in the hazy darkness above, Helen couldn't miss the jutting slab of manhood that rose exquisitely from his groin.

Understanding inherently what the young man needed at that point, Helen was desperate to give it to him considering the complete and utter joy he'd just unleashed inside her. There was simply no way however, she could have ever accommodated him inside her womb with as sensitive as it was. As if on some sort of primal auto-pilot, Helen rose from the bed and leaned forward until she was eye level with Jess' hairy, well defined chest.

Helen sensed an initial aura of disappointment from Jess when she eased upwards before he could get his right knee up on the bed to mount her.

"He really wants to be inside you," Helen told herself with a fair amount of pride.

Jess didn't seem to complain for long when Helen immediately lowered her head and took his ample cock into her mouth. A gasp shot from the young man's throat the instant Helen's lips closed around his straining girth.

Ingesting the bulk of Jess' manhood had been more than Helen bargained for however. A novice at best at oral sex, Helen only had her Husband's penis as a reference point. While Jess was only slightly longer than he'd been, there was a significant difference in the girth. It almost felt to Helen as if she was trying to swallow a banana whole. Jess, thankfully, had been patient with his advances despite his obvious urgency.

Helen was overcome by Jess' masculinity. Whether it was the musky scent of his arousal filling her flared nostrils, or the tender but certain strength of his hand placed on the back of her head, Helen quickly lost any sense of self control as the bulbous slab of Jess' erect phallus burrowed like a serpent over her tongue. Wrapping her right hand around the lean contours of Jess' behind to pull him even closer, Helen used her left to gently cup and fondle the young man's heavy balls.

In her mind's eye, even though she was on the verge of turning 66, Helen felt like an awestruck teenage girl there in the darkness with Jess, eager to fulfill his every demand.

The frustration on a multitude of levels had been boiling inside Jess for months, but now that burn was concentrated squarely in the sack of his sagging scrotum. His dick lodged firmly between the vacuum seal of Helen's lips, Jess hurled his hips forward with cruel grace, taking out his long deprived want on the older teacher's willing mouth. While he'd originally pictured depositing his lust deep inside Helen during an intense coital embrace, this was gonna have to do.

His cum rolling like white hot paste from the depths of his loins, Jess' gritted his teeth together and held Helen's head tight. Feeling the softness of Helen's right hand gripping his left hip, Jess shoved his dick relentlessly forward until it burst like a firehose in her overwhelmed mouth.

"GOODDDDDDDDAAAMMNNNNNN," the 28 year old groaned, the veins in his neck visibly rippling as he humped forward, looking almost demonish as he shot his warm and creamy seed down Helen's gullet.

It took a few seconds from the adrenaline that accompanied Jess' release to subside enough for him to look down through the darkness and survey the erotic carnage.

"...I'm...sor...," Jess started to stammer, wanting to apologize for cumming down Helen's throat, before the lady seated in front of him patted him gently on his belly as if to say she had no problem with the outcome.

Allowing the cylinder of Jess' rubbery, sperm and saliva laced cock to slip free from her lips, Helen then leaned forward and swirled her tongue around each of Jess' tender nipples several times.

It wasn't long before the couple found themselves huddled together on the bed, each too exhausted and incredulous for words, just simply enjoying the moment. At some point Jess stood up and told Helen he was headed upstairs to check on the kids once more before going to sleep.

Helen cringed but understood, watching with great admiration, and still a fair amount of want, as Jess disappeared up the steps. Laying there in the darkened silence, Helen had every opportunity to feel guilty about the events of the evening. She knew that things would probably be different under the harsher glow of daylight, but for the time being she stared up at the basement door, her insides twisting as she waited for his return.

_________________________________

For the first time since her Husband took ill many years earlier, Helen Conway felt safe and secure as she fell asleep beside another man. A giddiness she was completely unprepared for also fizzed in her marrow as she anticipated what lie ahead.

"Don't get too full of yourself," Helen's inner rationale tried to warn. "He's gonna wake up in the morning and wonder why the Hell he's in bed with such an Old Bag!"

Having decided a long time ago not to give too much thought to the future, Helen huddled herself closer to Jess and drifted off to sleep beside him on a bed that barely fit them both.

Helen didn't know just how long she'd been asleep, but it was well before dawn with she was awakened by a burning tingle in her loins. For a few seconds she thought with horror she might have wetted herself during the night but it didn't take long after she'd put her hand down there to realize it was an especially moist case of the sleep-induced arousal she'd long suffered with.

Jess was sleeping soundly beside her despite the awkward position the size of the bed forced him to lay in. Her left thigh placed against the crook of his groin, Helen found herself working her knee up and down until the shaft of Jess' hibernating penis gradually filled with life. It wasn't long before he too, was stirred awake.

Like two magnets, Helen and Jess' mouths found each other's in the dark, and in a flash all four of their hands were roaming greedily over every nook and cranny they could find. Stroking her left hand down the muscles of Jess' upper arm, without a hint of pretense she steadily began sliding it down his side before gliding it across his belly until she's tucked it once again between his legs. Feeling the young man's half asleep body wince to life when she clutched her fingers around his hardening cock, Helen reclined all the way on her back and watched as Jess lowered himself down on top of her.

Within a few seconds she could feel his lips tracing across the softness of her breasts, his long and angular tongue lapping and swirling across each milky white orb until he took one of her nipples, like a juicy plum between his teeth, and rolled it delicately around his mouth.

Helen clearly understood where this early morning session of impromptu foreplay was headed, and she by no means wanted to derail it. If, heaven forbid, this was going to be the only night she and Jess would share, or worse yet all this was simply the most vivid dream any human being had ever had, she was desperate to milk every last bit of deprived lust she could from it.

Feeling one of Jess' hands cupped beneath her ass as he hungrily kissed her titties, Helen contorted her body upwards until she could whisper into the young man's ear. What she asked not only caused Helen to blush, but it stopped Jess cold in his tracks.

Still fighting off the cobwebs of sleep, Jess wasn't sure if he'd heard Helen right. His cock rock hard and ready to penetrate the quivering woman beneath him, Jess couldn't deny that what she asking did intrigue him. The softness of Helen's breath cascading into his ear when she made her plea a second time, a twinkle of understanding sparkled in Jess' eyes as he rotated his body around on the bed.

Keeping his right hand wrapped firmly around Helen's asscheek, Jess kissed the widow repeatedly on the neck with a tenderness that would belie everything she was asking him to do. Putting his feet down on the floor as he sat on the edge of his bed, Jess then took the older woman's compact body over his knee and surveyed the surreally carnal sight below.

Petting the woman's back for nearly a minute, from her head all the way down to the backs of her knees as she rested perpendicular across his lap, Jess finally leaned down and asked Helen if she was ready for him to start spanking her.

"...Yes...," an eerily calm voice trickled like velvet smoke from her lips as she huddled her naked torso on top of Jess' thighs.

On one hand, Jess Tuttle felt like one of the most powerful men in the world as he sat there with Helen draped across him, having just heard her give him free reign over her entire body. There was still a twinge of apprehension however, unable to quite pull the trigger on the ultimate power she'd just given him. All it took was a couple of seconds of looking down and seeing the way Helen was squirming on top of his lap, along with the raspy pleas to spank her that continued to echo inside his head to finally push the young man to action.

Raising his right hand into the air, Jess couldn't help but imagine just how cartoonish all this would look in the right light. There he was nearly 40 years younger than his fellow teacher, preparing to smack her bare ass. Despite the absurdity of it all, Jess brought his opened palm down until it cracked against Helen's right asscheek.

A tepid gasp leapt from Helen's mouth as she slithered across Jess' knees.

"...Good...but harder Jess...a lot harder," Helen said without turning her head, her voice soft but certain.

A new wave of adrenaline shooting through his body when he heard the controlled surrender in Helen's tone, Jess traced the spot on Helen's behind he'd just smacked with his tingling fingertips before raising the hand back up and bringing it down a second time, this one much firmer than the first.

His blood raced upon contact when an ear splitting shriek immediately shot from Helen's throat, piercing the darkness surrounding them. His toes tapping with excitement as he steadied his feet on the floor, Jess once again traced the tips of his fingers around the area he's just spanked before raising his hand for a third time.

Seeing Helen coil up and hold her breath in expectation of the third impact, Jess rotated his hand a foot and a half above her ass until finally deciding to bring it down hard, this time on Helen's left asscheek.

"AAAAAHHHHHHHH," Helen moaned, pain clear in her voice, but also a trace of surprise as well that Jess had so effectively switched his pattern.

Settling comfortably down on top of Jess, both her cheeks now reddened and buzzing, Helen gripped her right hand on the bottom part of the mattress and dug her left into the cluster of pillows beside her head. Feeling the warm and stabbing presence of Jess' erection against her belly as she laid there, Helen could almost smell the sense of empowerment and control now flowing from the young man.