Miracle on Slutty 4th Street

(This story is posted on the Literotica website. Do not repost anywhere else without the author's consent. For fans of my stories, they know what kinds of things to expect. This story deals with similar themes as the stories by wannabeboytoy, seducedHylas, and Dark Betrayal, namely cheating, betrayal, and heartbreak. If stuff like that isn't your cup of tea, then you probably shouldn't bother reading it. I do not condone any of these actions in real life. This is just a story. Enjoy.)

(Additional note for this series: EACH CHAPTER IN THIS SERIES CAN BE READ ON ITS OWN. Each chapter is self-contained, but if you do read the whole thing, some of the specific details will become clearer and more fleshed-out. Enjoy)

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(Chapter 4)

"You are shameless!" Polly said, grinning, to her 18-year-old grandson, Connor, as they entered her car in the church parking lot.

"What?" he said with a big smile, knowing exactly what she was talking about.

"Don't act like you don't know..." Polly said, turning on her car and backing out of the parking spot before pulling out on the road.

"You had that poor girl wrapped around your finger," she replied, referring to the cute 18-year-old daughter of the preacher.

"I was just chatting with her," he replied innocently.

"A girl like her can't handle a big city guy like you," she joked, knowing the town he was from wasn't exactly huge, but it was certainly bigger than Deerberg. "If I didn't stop you when I did, she'd be renouncing the church and God knows what else. She'd probably end up on her knees worshipping something else entirely..." she said, causing her normally confident grandson to blush slightly. "Just leave the poor girl be. Besides... YOU should know better! You're the one with the girlfriend."

"Like I said, I wasn't doing anything," he replied.

"Hon, you gotta learn to turn that charm off," Polly advised. "Trust me, it'll get you in trouble."

"Hey, you were the one twirling her hair around her finger when talking up that teacher guy..." Connor retorted.

"I was not!" she replied with a big grin, mock offended.

"Grandma, that guy was, like... Mom and Dad's age," he stated. "Robbing the cradle a bit?"

"If you think that's me robbing the cradle, you don't know me well enough," she replied with a knowing smile, her tone vague enough for Connor to be unsure if she was joking or not. "Besides, I'm a single lady about town... I can talk to whoever I want."

"And I'm a young guy who girls like to talk to..." Connor replied.

"A guy who, again, has a girlfriend, and shouldn't corrupting church-going girls with his dark, big city sorcery," she said, making him smile. After a long pause, she added, "She did have a cute butt on her, though..."

"Ha. Yeah, and that guy you were talking to had, uh... a premium dong... on him," he replied, unsure of the joke he was making as he made it. This comment made them both burst into laughter, before settling into a warm silence as they headed back to Polly's place.

After all the Calvorsons, sans Dale, had attended morning Church services, most of them made their way downtown for the big Christmas Eve parade. But two of them did not.

Polly Calvorson, the matriarch of this clan, opted to head home. Frankly, she'd been to the parade so many times it had lost all its novelty. Plus, she had plenty of cooking to take care of for the big meal tonight, and she couldn't put things off all day.

She was joined by Connor, her grandson, the oldest son of her daughter, Penelope. A handsome boy of 18, it was clear he'd aged out of such festivities like parades. He probably wouldn't have even gone to church if it was up to him, but his mother would never let that pass. She didn't want him to skip out on the parade either, but Polly stepped in and overrode her decision, assuring her daughter it would be fine, that he would be helping her out with the cooking. Penelope feared he'd just go back home and laze about, but Polly promised she'd keep him busy.

Polly and Connor always had a strong relationship, frankly much better than the one he had with his mother. One point the entire family could agree on was that Polly's daughter Penelope was a huge bitch, and a control freak, and she tried her best to keep her kids in line. Naturally, Connor pushed against this over-parenting, a point that caused some conflict between them, especially as he grew older and more independent. But Polly, she always treated him the way he preferred. Not as a rival, whose independence had to be tamped down, but as an adult. Even when he was younger, Polly always treated him like his own person.

But it might just come down to the difference in personalities between mother and daughter. On paper, just looking at them, they had a lot in common. Being mother and daughter, they shared many qualities. Similar blonde hair. Similar good looks. Similar bodies. Similarly large breasts. But that's pretty much where the comparisons ended. Penelope was bitchy, unpleasant, and very controlling. While Penelope was tightly wound and not always the most fun to be around, Polly was a blast. A real spitfire. And the fun thing was, she wasn't some doddering old lady. If anything, she was more keyed in and with it than her daughter was. Even though she was his grandmother, he always felt like he could talk to her like someone his own age, and not an authority figure like his mother. He could have conversations with his grandmother that he couldn't with his own mom. Things that would cause his mother to freak out if she knew he was talking about it, let alone doing. And the main subject of these conversations was girls.

Now, it wasn't that Connor was a delicate, shy young man who needed the sage wisdom of his grandmother. Quite the opposite. To put it bluntly, Connor slayed it with girls. A devilishly handsome young man with soulful yet playful eyes, a perfect shock of dark hair, a good tan, and a fit, cut Lacrosse player's body. Looks alone would be enough for him, but he had that certain, special something that all but insured he'd have zero issue getting laid.

Which he didn't.

Whether it be his unflappable confidence or his smooth way with words, he had talked his way into some pretty serious stuff in his 18 years. His high school career was a trail of girls who'd spread their legs for him, and it was a long trail. So, by the time most of his peers were first experimenting, he was on to the advanced stuff. By the point that some of the less experienced guys were letting a furtive hand slide between their girlfriends' legs for the first time, he was going balls deep in the prom queen's ass. And by the time he reached senior year, his gaze began looking outwards, beyond the realm of his high school.

A month into his senior year, he had ended up at college party, and had given this smoke show 21-year-old the night of her life. And around Halloween, after running into his young, fresh-out-of-college calculus teacher at the store, all it took was a small bit of chatting her up before she was vigorously inhaling his cock in the backseat of his car. She still blushed whenever she looked at him in class.

That all being said, he actually did have a girlfriend. He started dating Lucia after coming together at a Halloween party. They ran in different social circles, and they'd been circling each other for a while with teasing comments and light flirtation, but nothing was made official until they hooked up at this party. That was when they became official. And even though they'd only been dating for about two months, it'd been going really well.

Now, Lucia was not some sweetheart that was guiding Connor along the right path. No, she was as dirty and freaky as he was. Stunningly beautiful, with a great body, with a healthy pinch of wicked that made her irresistible. Every desire he had, she more than met. And while you might think otherwise, with all his history as a player, he was actually a really good boyfriend. All his charm and energy, focused on one girl... he could make any girl he dated feel like a princess. And honestly, he was truly content. It wasn't like he hadn't sowed his wild oats. He'd experienced just about all the things sexually, so the idea of settling down with a girl he really liked didn't seem like the worst thing in the world. He could get used to it. However, he was still a shameless flirt, hence the little incident with the preacher's daughter.

And no matter how much he settled down, he would always be a flirt.

That was a quality he shared with his grandmother.

It was a skill Polly picked up in her younger days when she did beauty pageants. She never took her flirting to an obscene level, but turning on the charm with some light flirting was imperative to winning over the judges, and as time went on and her skills developed, her flirt game was second to none. She had always been quick on her feet, and that skill, combined with her charm and her intense beauty, allowed Polly Calvorson to be named Miss Deerburg back when she was 18.

Despite this seemingly great award, it didn't make her many friends. Sure, the male population certainly appreciated her, but her female peers weren't impressed. Many nasty, untrue rumors were started about her, with her competitors attributing her victory to acts of impropriety she took part in, or the fact that Polly had the biggest chest and a perfect rear end, attributes that they thought she shamelessly displayed. None of this was true, well... at least the first part wasn't true. She didn't have to do anything improper to convince the judges she was the best. They came to that conclusion themselves.

Those skills, her charm and flirtatious nature, served her well in her life, even if it did come with some drawbacks. Yes, she did land a successful husband, a handsome man, 19 years her senior who took a great shine to the young beauty. That led to many years of happiness and a great big family. But, many years down the line, it led to strife in her marriage, as her husband's jealousy of her active social life, and his lack of patience with her still flirtatious nature, led to an irreconcilable rift between them which lasted till the day of his passing. But she was never starved for male attention, even up to present day. But because she was so charming and flirtatious, she could never fully escape the promiscuous label, one which wasn't always true. When she was married, she never once cheated on her husband, despite what some of her peers or even her husband might have said. Maybe at other times in her life she slept around, but certainly not then.

She had always had a healthy appetite for sex, and yes, at times it had verged on the unhealthy. In her younger years, she didn't have any scruples about sleeping around, and slaking her wicked desires. And she had always had a great time doing it. And when she got married, she put her focus on her husband entirely, never once cheating on him, despite plenty of opportunities. Even as he got older, and his jealousy grew, and the rift between them grew beyond repair, they always had an active sex life. Too active, it turns out. With him being so much older than her, he couldn't quite keep up with Polly as well as he used to. She could still give him a thorough seeing to, but things had reached the point where he had to lie there and hold on for the ride. And one night, after one of these vigorous sex sessions, he had stumbled up from the bed, coated with sweat, stumbling to the bathroom to get some water and catch his breath. The next thing Polly heard was a dull thud as he collapsed onto the floor.

Her kids never knew the circumstances of their father's death. They just thought it was a heart attack, never fully knowing what had incited it. This was a bit of a wakeup call for her, making her realize she probably had to tamp down her wicked desires and maybe start acting her age. So, she did so, devoting herself to her family, doing her best to raise them in such trying circumstances. It wasn't always easy, especially after her husband passed, but she took pride in the way her family came together afterwards, and that let her know she had done a good job with them. And now she was the grandmother of this big bustling family. She certainly didn't feel like a grandma, that's for sure.

She didn't look like one either.

Sure, she was many years past her beauty queen days, so she had some wrinkles. And she'd had three children, so her hips were a bit wider, but she looked damn good. A dedicated fitness hound since her youth, she was more active than most women twenty or thirty years younger. Her belly was flat, her legs were long and firm, and her arms were slim and toned. While she had some natural weight gain with aging, it all went to the right places. Her ass was absolutely mouth-watering, firm and perky and heart-shaped, each cheek round and full and perfectly formed, with an immaculate cleft in between. She took great pride whenever she noticed some young guy at the gym with his eyes glued to her perfect, mature rear end.

But none of this compared to her breasts.

They had been huge in her younger years, but after having three kids, they had sized-up to the point where they could only be described as absolutely mammoth. Full, round, jiggling GG-cups, they drew attention wherever she went. And somehow, she hadn't succumbed to the dreaded sag, her massive tits still firm and perky, bursting out from her chest, bouncing with every step she took.

On top of that, she worked hard to maintain her beauty queen looks. Sure, she had some signs of aging, but her makeup was always immaculate, her eyes looking smoky and sexy, and her lips smooth and glossy. Her hair was always well styled, her dirty blonde hair cascading past her shoulders, with only a hint of gray. She always dressed well to flatter her body while also keeping up with current trends. And on top of this, she always made sure to maintain a good tan, her skin golden and smooth even in an area not ideal for keeping one. So many of her peers had just taken the effects of aging and done nothing. Her neighbor Doris, God bless her, had become an old biddy, and someone like her other neighbor Janet was unwilling to put in the time to keep herself in tip-top shape.

But Polly... Polly was a hot grandma.

And she still had that charm and that way with words. Combining that with her hot body, and the ever growing sexualization and fetishization of older women, meant that despite her best efforts, she was getting more and more male attention. And that appetite for sex had never left her. She was on her own, and had no one to answer to, so she figured... why not have a little fun? Why not indulge in some fun? And yeah... she'd indulged herself, quite a few times, but never anything too serious. She was hot, she was horny, and she was very good at sex. It'd be a waste not to use these talents for fun.

So, in that sense, her and Connor had a lot in common. Both hot, both charmers, both very, uh... experienced... at hot, nasty sex. They'd forged their way through life in much the same way, having similar experiences and similar outlooks. Despite their obvious differences, her and Connor were two peas in a pod, able to bounce back and forth with jokes and comments behind everyone else's back. These two were on the same level, with Connor being at the forefront of things thanks to his youth, and Polly being wise to the ways of world.

Which is why, as they headed home, Polly knew exactly why Connor wanted to head home. It wasn't just because he was too cool for school and didn't want to attend the parade. No. Connor was an 18-year-old away from his girlfriend, cooped up with family. For the first time in days, he'd have a few moments of privacy without being in the same room as someone or having someone pounding at the door. Polly knew exactly what Connor wanted to do with this moment of privacy. He wanted to do what all 18-year-old guys did with every spare moment of time they had.

Furiously and vigorously masturbate.

Polly knew what made guys like him tick. And while she never invested much thought into her grandson in this way, she knew what type of guy he was. She knew he was a bit of a player, from his stories and his demeanor. She couldn't avoid coming to this pretty obvious conclusion, and everything she saw supported this.

Glancing over at him from the driver's seat as they chatted, she saw all the telltale signs of a young man dying to jack off. He was antsy. Anxious. Strumming his fingers along the armrest, eager to get some privacy so he could wrap those same fingers around his dick and just go to town. So, as they reached her house and made their way inside, an idea began to form in her mind.

Stepping through the door, they were met by a strangely anxious Dale, barely meeting her eyeline.

"I, uh... I still need get the stuff done outside..." he said quickly, passing them.

"You're not done yet?" Polly asked.

"Uh... no," Dale said simply, closing the door behind him. Giving him a curious look, she set down her purse and pulled off her coat, before looking up as Connor began making his way upstairs.

"I'm just gonna take a quick nap," he stated.

"No, no, no..." Polly said, shaking her head, barely containing her grin. "You're gonna be helping me out with the food. I promised your mother I wouldn't let you laze about, so you'll be helping me." The annoyance was clear on his face as he looked at his grandmother. The problem was he couldn't say the reason why, and Polly knew this. She held his gaze, her eyes twinkling in amusement at his predicament.

She didn't know why she was doing this. It didn't particularly bother her if he was gonna be lazy, and she had never felt any compulsion to help Penelope enforce her draconian parenting rules. Maybe it was something in the air, but she took great delight knowing she was mildly torturing her grandson by withholding him the pleasure of draining his swollen nuts.

Or maybe she felt like it was only fair for him to be as horny as she was. Polly had always been a woman with a ravenous sexual appetite, an appetite which had never been properly taken care of. And with her house so busy, she wasn't able to slake her own desires any more than Connor could. So... fair is fair.

For a moment, Connor wondered if his grandmother knew exactly what she was doing. She had a wicked sense of humor, and sometimes her joking pushed some barriers. But rarely was it this wicked, especially when involving her grandson. Not knowing what else to do, he exhaled, shrugged his shoulders, and accepted his fate.

"Well, can I at least change first?" he asked.

"Yeah," she said, eyeing his church clothes. "Probably should. But be quick about it. We have a lot to do." Moving quickly and heading to the room he was staying in, he took off his button-up shirt and pulled down his slacks. He always found this kind of outfit uncomfortable, so he was glad to be rid of it. As he stood in his underwear for a moment, his fit tanned body exposed to exactly no one, he couldn't help but notice his swollen, hefty teenage dick straining against his tight dark boxer-briefs. Looking more like a salami stuffed in his underwear, pointed towards his hip, he wished he had a fifteen minute or so respite just so he could take care of business. He could try to do it quickly, but he wanted to savor the moment, you know? It would be unsatisfying to take care of things with a countdown clock, and it would be even worse if he got interrupted halfway through.

If it wasn't clear, he REALLY missed his girlfriend. He and Lucia had a very active sex life, and he was an 18-year-old bursting with desires and needs, so he was used to having his balls drained regularly. Being cooped up with family, having a minimal amount of privacy, his balls were understandably boiling. He was dying to cum but there was no relief in sight. Exhaling again and pulling on a comfortable t-shirt and some basketball shorts, he headed back downstairs, trying to ignore the straining pressure coming from his hard dick and giving one last check to make sure his erection wasn't visible.