The Spanking of Widow Conway Ch. 01

The time on her Father's knee didn't do anything to quell the teenage hormones raging inside her body, but Helen knew the certainty of the stick scared her a Hell of a lot more than the unpromised joy of the carrot.

Somewhere along the way, deep in the contours of her still developing adolescent brain, the slithering and irresistible lust that swirled through her loins intertwined itself with the sizzling pain of her Father's loving wrath. The yin & yang of that complicated psychic interplay would have been great fodder for the studies of Freud and his disciples.

On one hand, for much of her early adulthood Helen was unable to allow herself to be in the company of a man without the guilt and fear of punishment hanging over her head. It had even taken a year or so after marrying her Husband for Helen to completely allow herself to enjoy his advances.

On the other hand, anytime Helen was confronted with the direct and unflinching use of discipline in her daily encounters, she found herself secretly overcome by the repressed longings of her youth. To get herself off in the early days of her marriage to an equally young and sexually naive man, Helen would frequently imagine the presence of a large and unforgiving hand repeatedly coming down on her rear end during their awkward attempts at sex.

In Helen's mind, the guilt of such a thing needed to be buried. Even though she'd had her bare ass spanked on several occasions by her Father while growing up, nothing remotely sexual ever occurred between the two. There had been several occasions during her marriage that Helen had been sorely tempted to bring that part of her fantasy life out into the open with her Husband, but she could never bare the thought of speaking such a thing to the kind and gentle man she'd swore her vows to before God.

It wasn't until she heard Jess Tuttle give his Son a spanking in her house that sunny Spring afternoon that all those long imprisoned demons suddenly burst free, and this time Helen knew they weren't going to be easy to put back in.

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Helen looked like a cat on a hot tin roof at times around Jess as the two managed the classroom. Figuring the kids most likely just assumed she was an old lady with nerve problems, Helen didn't give much concern to what they thought. When she was alone with Jess however, she did everything she could to maintain an air of composure.

It was all so stupid really. Here she was well over twice the young teacher's age, yet she was the one tip-toeing around like an anxious and befuddled school girl.

Helen looked just like lightning had struck her heels when Jess asked if she'd be interested in babysitting his two kids the following Saturday night. Jess' estranged Wife was going to be away that weekend and he had a chance to go out on a date with a woman he'd been talking to for awhile.

"I'll be glad to," Helen found herself agreeing, even though the slightest twinge of jealousy did trickle through her tissue.

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Jess Tuttle looked quite handsome dressed up for his date when Helen arrived to babysit the kids. Again the pangs of jealousy teased her senses when she caught first whiff of how good his cologne smelt.

"Don't worry about a thing," she told Jess as he gave his Son and Daughter their final marching orders.

The kids had been delightful. They'd known Helen long enough by then to trust, and like her, and Justin and Trina had actually gone to bed a little after 9 with only having Helen have to ask them twice.

With the kids safely tucked away, Helen was left with the better part of two hours to kill before Jess was slated to return home. Not a big fan of television and desperate to keep her mind occupied, Helen found a couple of hampers full of dirty clothes and decided to take them downstairs to wash for Jess.

Helen was immediately taken aback when she realized someone was living in the roughed in basement. It took her a few seconds to remind herself of Jess and his Wife's living arrangement, but it dawned on her that Jess was sleeping downstairs while his Wife kept the master bedroom.

"What a shame it had to come to this," Helen thought to herself, knowing prisoners in many cases had a better place to hang their head at night than Jess did in his own home.

Having read a couple day's worth of accumulated newspapers laying around the house as the clothes washed downstairs, even for someone as respectful as Helen was about other people's privacy, she found herself snooping around Jess' modest abode when she went back down there to put the clothes in the dryer.

It didn't take her long to notice something on the floor Jess would have just assumed she didn't see. There was a modest stack of Playboys and similar types of magazines scattered, but visible, under the nightstand beside his makeshift bed.

"Well the last thing he thought when he left you to look after the house was that you were gonna come down here and try to wash some clothes," Helen chided herself.

For the most part, the presence of stuff like that didn't bother Helen all that much. Despite her staunch Christian upbringing, she knew stuff like that existed from a pretty young age and there were even times she found a couple of issues that her deceased Husband had snuck into the house over the years. Unlike those however, Helen wasn't going to throw Justin's reading material in the trash.

In a strange way seeing those things on the floor and picturing the young man laying there in bed seemed to only increase the awkward feelings she was having for Jess. Once again she found herself rolling her tongue around her mouth, wondering how his date was going.

She got her surprisingly quick answer less than 15 minutes later.

Helen could immediately tell from Jess' body language things hadn't gone as well as he'd hoped.

"She didn't believe me when I told her I was separated since we're still technically living together," he shook his head and told Helen with a definite tone of befuddlement.

"Well...it is a unique living arrangement," Helen smiled soothingly, internally thankful she wasn't out in the dating world with as complicated as it had become over the years.

"Kids' mind OK?" Jess asked, desperate to take his mind off the events of the past few hours.

"They couldn't have been better...put them to bed around 9," Helen replied proudly.

"Good..," Jess sighed. "I'll run up and look in on them real quick."

"While you're up there...I'll get the clothes I washed out of the dryer," Helen added nonchalantly.

Jess started up the steps to the kids' rooms before Helen's previous statement finally sunk in.

"You didn't have to wash any clothes, Helen?" he said after turning around.

"No big deal...I got bored and was looking for something to keep me busy after putting the kids to sleep," she fidgeted and said.

"Well...thank you," Jess offered his heartfelt appreciation until the blood in his body nearly froze when it dawned on him what the older woman might have seen while down in the basement.

The air between the two quickly filled with an unspoken understanding.

"I'll get the clothes while you check on the kids," Helen once again did her best to diffuse the awkward moment.

Helen was still stuffing the dried clothes into the basket when she heard Jess' footsteps descending the stairs behind her.

"Let me help you with those," he offered as he made the landing.

"Oh...I got it," Helen turned around with the full basket and smiled, noting the slight blush of embarrassment on the young man's face as he visibly tried standing between Helen and the stuff beside his bed, just in case she'd somehow missed it's tawdry presence.

The playful dance ended when Helen finally handed the clothes basket to Jess and started to walk up the steps in front of him.

"I can't believe she's making you sleep down here," Helen said with clear bitterness.

"My choice," Jess took a deep breath and sighed. "The sofa in the living room is way too small and messes with my back...I wanted to make sure both kids had a room of their own so going downstairs was the best option."

"Can I get you a beer?" Jess asked once he'd sat the clothes down in the kitchen and made his way to the fridge.

Helen politely shook her head, 'no', but took a seat at the dinner table and made conversation with Jess as he wound down from a trying evening.

The quick bit of small talk at the table evolved into an hour and a half conversation. Between discussing the kids and Jess' situation, to the things going on at school long with several other topics of the day, Jess and Helen suddenly found themselves staring at the clock.

"I better get out of here before my carriage turns into a pumpkin, "Helen laughed, hiding the fact that she didn't trust her eyes much anymore to drive at night.

"It's a Saturday night...why don't you just spend the night?" Jess offered.

"You can sleep up in Michelle's bed...its not like she's gonna be home tonight," he added with somewhat bitter sarcasm.

"Oh...I couldn't," Helen found herself replying even though Jess' idea had some merit.

It took the younger man having to ask several more times but Helen finally gave in.

"I'm gonna warn you...I'm an early riser," Helen joked.

"Not if you stay up much longer, you wont," Jess chuckled back.

"Oh God...I just remembered I don't have anything to wear," Helen cringed.

"You and Michelle are about the same size...I'm sure she has plenty of nightshirts laying around...just grab one of those," Jess suggested.

"That'll be weird," Helen laughed again, privately thankful she wasn't going to have to make the 20 minute drive home in the dark.

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Helen Conway could have counted the nights she hadn't spent in her own bed on two hands since getting married over four decades earlier. It made for a very surreal feeling laying there trying to fall asleep with so many different noises and patterns of light coming through the window.

Sleep was long in coming and not very sound.

As she laid there, teetering between sleep and consciousness, Helen couldn't keep her mind from wandering. For someone as self conscious and polite, Helen felt guilty sleeping on the plush and comfortable king sized mattress of Jess' marital bed while he was downstairs in the musty basement, tossing and turning on a second hand twin.

She also couldn't help but develop a bitter taste in her mouth knowing what Jess' Wife was off doing while he was two floors below, stewing in the disappointment of a disastrous date.

"Is he down there flipping through those magazines beside his bed?" a scandalous and blush inducing voice rose from the catacombs of Helen's mind.

She laid there, 90% asleep, shimmying somewhat under the covers as she contemplated that very question.

From the images sprouting inside Helen's head, she knew she had to be dreaming, despite the overwhelming visceral feel that it was all real. That ability to dream so vividly had always been a blessing and a curse. Imagining she was downstairs in the foyer of Jess' house, standing in stone silence in front of the much younger man, Helen sheepishly bowed her eyes when she felt Jess approach.

Within a few seconds she could feel both his arms wrap around her, as if hugging her appreciatively for coming over that night to babysit the kids. When he tried to release his grip however, Helen could feel her own hands scrunching into the sides of Jess' half unbuttoned dress shirt, as if to say, 'please don't let go'.

Her hands gripped into the sheet covering her as she slept, Helen imagined holding that pose with Jess for several minutes until she did something she knew she could have never done while awake.

Suddenly Helen found herself on her knees in front of the young teacher, her breath shallow and her eyes glazed over as she stared at the bulge tenting out the front of his slacks.

Helen's inner core turned to molten rock as her brain attempted to grasp what she was seeing herself do in her dream. She could almost feel the imaginary zipper of Jess' pants between her fingers as she tugged it down. A rush of adrenaline shot through Helen's body as she shivered in bed, seeing the shaft of Jess' erect penis swing like a switchblade from his unzipped fly.

The side of Jess fully aroused manhood smacked Helen square on the right cheek, causing her to reach out with her hands and grab Jess by the knees to keep herself from toppling forward. Swearing she could feel the pressure of his 10 fingertips bracketed around the top of her short, salt and peppered hair, Helen opened her mouth as wide as she could and ingested the younger man's throbbing prick.

Her knees teetering as she knelt at Jess' feet, Helen visualized wrapping her left arm around the back of Jess' legs as she grabbed the base of his cock with her right. For several seconds afterwards, Helen fantasized about giving the 28 year old man a blowjob in the main hallway of his house, the entire time feeling the luscious weight of Jess' smirking stare as he rotated his hips forward, shoving every inch of his glorious cock over her swirling tongue.

Her right hand now wedged tightly between her thighs under the covers, Helen masturbated herself for several minutes in the strange bed, imagining the friction of Jess' blunt erection see-sawing between her stretched lips until the rich and salty report of his cum splashed down her churning throat.

Sleepily frigging herself off as she pictured herself on her knees servicing Jess, the sudden sound of far away cries stirred Helen awake. Pulling her greasy hand from her crotch, it took a few seconds for Helen to wake up and re-acclimate herself with her surroundings. Scolding herself for exhibiting such moral weakness, Helen held her breath trying to listen for the sobs that had woke her up.

Hearing the echo of a man's footsteps coming up the stairs, it dawned on Helen that Jess had heard his three year old Daughter crying in her room. Slowly unfolding herself out of bed and gliding her bare feet across the floor, Helen stopped just inside the cracked bedroom door and watched as Jess entered Trina's room.

A few seconds later Jess emerged, holding the young girl in his arms. For nearly a minute Helen watched from the shadows as Jess paced back and forth down the upstairs hallway, patting his Daughter tenderly on the back as he whispered a lullaby into her ear. Helen could feel her heart melt as she watched the tenderness and patience Jess exhibited, especially considering how frustrating his night, not to mention the last few months, had been for him.

Once he seemed to have settled Trina down, Helen watched from her hidden perch as Jess put her back to bed before heading back downstairs himself. Gripping the inner knob of the door tightly with her right hand as she watched a shirtless Jess disappear from sight, almost like a small bird that had been swept up in the contrails of a large jet, Helen found herself seemingly gliding on air as she squeezed through the bedroom door and followed Jess down the steps...

Part 2 to come...