(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 10)
Janet Winston's best years were probably behind her. But you couldn't say she hadn't lived.
The older woman had just about seen it all in her time. Spending most of her life seeking every form of pleasure out there, she took every opportunity to enjoy herself and be taken to her limits. From a young age, she'd been a bit of a party animal. Partying hard. Drinking hard. And, of course, lots and lots of fucking.
Now keep in mind, when she was younger, her rampant promiscuity was a thing society said she should be ashamed of. That was just the attitude of the time, with them looking down on anyone who had such loose morals. But it was those people who were left in the dust as time moved past them. A couple decades went by there where various acts of hedonism, such as partying and drugs and rough sex, were commonplace. And in this era, Janet fit right in. And, in truth, as society moved beyond this, she never really left that era behind.
As that insane level of partying became a thing of the past, and people became more aware of the dangers of this lifestyle, Janet never stopped. She couldn't. She loved it all so much. She couldn't let go. It was all she knew. More than anything, this time period shaped the person she'd be for her entire life in a fundamental way, and she could never truly evolve beyond this. While her peers had long married and started families, she was still going to the bar. She was throwing herself at men. She was trying to keep that party going even when most everyone else had left those days behind.
She'd been called all sorts of names. A spinster. A slut. A whore. And, to be fair, these descriptors were pretty much true. She was a slut. She'd been one for pretty much her entire life, and that had never once changed. When she was younger, she'd hook up with pretty much any good looking guy that crossed her path. And as time went on, she didn't really discriminate. If they were handsome and up for the job, she'd try them out. But as she got older, she really began to prefer younger men. Young, handsome studs, full of lust and vigor and so much cum. This was at the time when MILFs were first becoming a thing, so she cleaned up with guys looking to live out the newest, hottest fetish.
She kept at it for well beyond what would be considered decent or proper for a woman her age. Even though she was by all accounts an old lady at this point, it wasn't that long ago where her and a friend near the same age flew down to Mexico around spring break, threw on filthy bikinis, and joined the partying masses, looking to poach super-hot drunk college guys for some wickedness. She showed plenty of guys what it was like fucking a real woman, and she had no doubt that she left a permanent mark on all of them.
Even though she had maintained her good looks and hot body for so long, well beyond most others, age eventually began to take its toll. Her brown hair began to grey. The wrinkles on her face couldn't be hidden with makeup anymore. The weight of her large, zeppelin-sized boobs became too much to bear as they began to finally sag. The engines inside of her began slowing down. And fighting off weight gain was a losing battle. Her mind was still as sharp as ever, and you could recognize that she used to be a true looker. But it had become harder for her to reel in younger guys these days. Sure, guys had a thing for older women, but even they had limits, and she was beyond those limits for most. Sure, she still was able to pull in a few, but that was mostly when they were extremely drunk. She was still able to hook up with men closer to her age, but that was never as fun for her. Even though her mind still missed the thrill of the hunt, and she was still the firecracker she'd always been, she couldn't truly deny that her life of endless leisure and hedonism was probably over. Not many women that partied as hard as she did make it to her age, so they never had to experience the slow infuriating decline. The best she could hope for these days was probably the pleasure that came from her big pink dildo and whatever wicked fantasies her mind could come up with. And as she got older, those fantasies only got filthier.
Janet had lived on Fourth Street for a long time now. Of the houses along the street, hers was among the smallest, but it was far from small. It more than met her needs. She'd never been married. She'd never had kids, or ever really wanted any. She was not the motherly type, although she had made a few handsome young men call her 'Mommy' in the heat of passion, but that was beside the point. It had been a long time since she'd had to work, as she had amassed her savings in other ways, mainly through various inheritances and the ability to squeeze money out of deep-pocketed men. So, for the longest time, she had nothing to distract her from the fun stuff.
Janet never really fit in with the image of Fourth Street and Deerberg and the image they both tried to give off. This was supposed to be an area that lives by the code of Christmas. Good behavior, charity, and living up to the tenets of the Church. And yeah, Janet wasn't about that shit. She'd never gone to church as she knew she'd stick out there. She'd never felt bound by rules and codes of ethics. If she wanted something, she went after it. She had been a greedy, self-centered slut, and that had never changed. The Church? The church she knew feared women like her.
Clearly, some people didn't want a woman like her around them. Old Doris Carroll had never wanted Janet in her pristine, perfect neighborhood, sullying it with her slutty manners. Doris had never liked her, even when they were younger. Sure, that might not have been helped that Janet would constantly flirt with Doris's ex-husband. Janet knew men, and she could tell which men, despite all claims to the contrary, were available for some fun. And that one, Doris's husband... he had a wondering eye. She just knew it. And she'd been proven right, as he eventually ran off with the preacher's daughter. Janet could never fully hide the smug sense of satisfaction she got about being right about Doris's hubby, and that further cemented Doris's dislike of her. Janet never went out of her way to endear herself to Doris, never changing her ways in the slightest. In fact, she only turned it up When her boys got old enough, Janet flirted with them nonstop, curious if they were cheaters like their father. But none of them ever bit, which was a shame, as they had all grown up and became handsome men. What Janet would give to have landed just one of that Carroll clan. Dan and Frank were probably too shrewd for her tricks, but she could have definitely landed that Tim. What a victory that would be in their cold war, seducing one of Doris's sons. Doris wanted her family to be everything right in the world, and Janet was the antithesis of that. Janet conquering the Carrolls, and proving herself right... it just sounded mouthwatering. But alas, it never happened.
Early on in Janet's time on Fourth Street, it seemed like more people veered to the Doris side of the scale, the neighborhood being very religious and chaste and frankly boring. But as time went on, it seemed like the scales had tipped the other way. Slowly but surely, Janet was gaining more and more friends in the neighborhood, and Doris and her boring, religious ways seemed to stick out and seem old-fashioned. Janet seemed far more in touch with the ways of the modern world more than Doris did.
In many ways, Janet was born at the wrong time. If she was a little younger, she would absolutely SLAY with men. After a couple decade moratorium on the partying and pleasure-seeking lifestyle throughout the world, it had come back even stronger than before. People these days were up for ANYTHING! Adding on to that the rise of the worldwide fetishization of older women... needless to say, Janet could cut a wide swath of destruction if she were only slightly younger.
