Old Ladies, Thongs, & Whiskey

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.

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Josh sat at the bar, sipping a craft beer, waiting for his wife to arrive.

This was a weekly tradition for Josh and his wife, Deborah. Every Friday, they made it a point to go to the bar after work, get some drinks, and just relax. They liked to unwind, vent about all their troubles of the week, and leave those worries behind them.

The P-Boro Pub was their favorite bar in town. Ever since moving to the area, it had been their go-to spot to get drinks. Everything inside was made out of nice, warm wood, and they had a great alcohol selection, making it a very inviting locale for the young couple. It wasn't, like, a 'bar' bar, you know? It wasn't overly loud. There were no darts or pool tables or anything like that. It was a more modern and cooler locale, and it attracted a young, hip clientele. And as they just opened, the young couple were excited to become regulars at a place from the start, and they had done so. A few years out of college, they were both professionals with good, busy, well-paying jobs. As happy as they were with their current state, they both needed their time to unwind, and the Pub was a prime spot to do just that.

Deb had just texted Josh that her meeting was running very long, so she invited him to get started without her. Which he was, sipping his beer, eyes on the TV above the bar.

He didn't used to be a big drinker, as he never found the cheap beers his friends would have at parties particularly palatable, and straight-up booze never really did it for him either. Frankly, it was kinda too strong for his tastes. But Deb was really into craft beers, the type of stuff these little breweries in the area made. IPAs, porters, ales, etc. Drinks that had far more character, richness, and flavor than the big brands you see commercials for during football games. Deb had him try these craft beers early on in their relationship, and that had been his in to developing a taste for beer. He now had a well-developed palate for the stuff. P-Boro Pub had their own in-house brew, which he was drinking now, and sipping it down after a long, exhausting week made it taste even better.

"Hey there," said a woman, sidling up next to him. For a moment, Josh's eyes went wide as he looked at the woman next to him for the first time. She was a stunner, no doubt about that. A platinum blonde dressed in a professional yet figure-hugging red top, a slim black skirt, and high heels. She had large, perky breasts which stretched the confines of her slim top. And her round, shapely ass did the same with her skirt. She glanced at Josh with a confident smirk and a mysterious glint in her eyes. Damn... she was absolutely gorgeous.

"Uh... hi," Josh said, taken aback by being confronted by such a beautiful woman. His wife was very pretty, but certainly not jaw-dropping like this woman.

"I'm Samantha. And you are?" she asked.

"Josh," he stated, a bit confused.

"You mind if I sit here?" she asked, presumptuously taking a seat next to him.

"Um... I guess it depends," he replied, causing her to smile.

"On what?" she asked.

"Depends on your intentions," Josh stated, his alarms slightly raised. Her eyes narrowed knowingly.

"Well, if you buy me a drink, we can talk all about my intentions," she said with a hinting lilt.

"Uh... yeah, I'm married," he stated, raising his hand, showing off the wedding band on his finger. "Waiting for my wife to show up actually." She winced slightly at this, but she was undeterred.

"That doesn't mean we can't have some fun first," she purred. This wasn't the first time he'd been hit on at this place. A handsome, well-built, clearly successful man alone at a bar... it was inevitable he'd attract some attention. And he had... quite a few times, actually. But by this point, he was a deft hand at shooing away this kind of unwanted interaction.

"Actually, it does," Josh replied firmly, letting her know he wasn't some guy asking to be poached by some beautiful, aggressive young seductress. Studying him for a few moments and seeing that his resolve was firm, she stood up and ordered a drink. Once the martini glass was slid into her grasp, she turned to face him again.

"Shame..." she replied, sipping her drink. "The best ones are always married, but that doesn't always stop them from playing. I guess I'll have to find someone more fun," she said, taking another sip before sauntering off, shaking her immaculate ass from side-to-side as she did so. Rolling his eyes, Josh turned to face the bar again, looking down at his phone, hoping for news from his wife as for when she'd be showing up.

This was the reason he always wanted to meet up here with Deb at the same time, just so this kinda thing wouldn't happen. Because it seemed like whenever she was late, or if he was simply alone at the bar for an extended period of time, some enterprising tease would find her way next to him and start lightly flirting, aiming for something more. Sometimes, they persisted even beyond him mentioning his marital status, forcing him to put his foot down. Josh was a good husband, and he had never indulged in that kind of behavior in the slightest, despite having had many opportunities. He was a good man, and he cared about his vows. Nothing would ever get in the way of that. That being said, it was always nice to get some attention, even the unwanted kind. And to be hit on by someone so attractive was certainly a boost to his ego. But he tried not to get lost in this kind of thinking for too long, despite the ego-stroke it provided.

Unfortunately for him, he was a prime target for this kind of attention, more so than would have expected. But then again, he didn't quite know what a juicy target he was for these scheming teases. He was tall, fit, and handsome. Brown hair, warm eyes, and a kind smile, he could make even the most hardened slut melt without even trying. He dressed well, indicating his success, and he exuded a quiet confidence without effort, all good qualities that only increased the target on his back. Being alone at a bar made practically made him a beacon for eager sluts on the hunt for big game.

He kept his eyes down on his phone as he tried not to catch anymore unwanted attention. But alas, just as he received a quick text from his wife explaining that she was still in her meeting, he sensed a new presence next to him.

"You really missed out with that one," said an older, smoky female voice from beside him. "She seemed like she'd be worth a good roll in the hay."

"I'm married," Josh responded without even looking up, texting back with his wife.

"I mean, that girl has tits that are cum targets, my goodness..." the woman stated, undeterred. "She probably needs no help getting laid. If she's not getting it from you, she's just gonna get it from someone else. But it's probably for the best. It just means you'll be coming home with me tonight."

Finished with his text, and finally absorbing what this woman had just said, he lifted his eyes from his phone and looked up. And what he saw was not what he expected.

The woman standing in the same spot Samantha just did was about as different from her as could be. While Samantha was young and beautiful, this woman was... not. This woman was older... much older. And you could describe her as many things, but beautiful wasn't one of them. She had short, dirty blonde/light brown hair, folded on top of her head in a somewhat stylish manner. Her face looked her age, with some wrinkles and crow's feet and age lines. She was probably in her late forties or early fifties, but these things made her look a little older. Or maybe... she just was older than he originally suspected. And because of all that, it would be difficult to consider her beautiful. She wasn't like some older actress you see in movies, who could have been a model in her younger years. No, this was a real older woman. She was certainly not hideous or anything like that. She was just not exactly super-hot looks-wise. That being said, she didn't let that stop her. She was wearing make-up, dolled up for a night on the town, but she didn't seem like the type who would make time to do such a thing normally. She had eyeshadow around her sharp, angular eyes, smooth pink glossy lipstick across her full lips, and a bit more on her face to perhaps smooth things out. But what stood out most about her was her tan. While some women had that perfect level of golden tan perfected, this woman was about a notch beyond that. While she hadn't taken it to extreme levels or anything like that, she'd probably spent too much time in the sun, giving her a slightly overbaked look. Yet, she was undeterred. She struck him as a woman who wasn't gonna let her age hold her back.

Her outfit matched up to his first impression of her. On her legs were tall, knee-length leather boots. Above those, adorning her legs, were black mesh stockings, leading up to a slim, black leather skirt, clinging to her thighs. Up top, there was some color to be found to contrast against the darkness of the rest of her outfit. A slim top, made out of some sort of smooth material, colored white, purple and black, in a slightly floral pattern. The top was short-sleeved, allowing her lithe, tan arms to be left exposed.

But what really caught his attention was her chest.

This woman, despite having some meat on her bones, had a relatively fit figure, all things considered, which made the fact that she had absolutely massive breasts all the more noticeable. Enormous and round and full, they looked like tanned, overinflated balloons, stuffed into her top, bursting to get out. The top had laces from the neck down to the middle of her chest, and they were straining to contain her massive bust. The fault-line of her smooth, mature, sunbaked cleavage was visible beyond the laces.

Her thin, bony hands were resting on her hips as she let him take her in for the first time. When he looked up into her eyes, she seemed amused by his confused gaze.

"I'm sorry?" Josh asked, confused, setting his phone down on the bar.

"Well, now that that little tease is out of the way, you've left yourself no other option but to come home with me tonight," she stated with a knowing smirk.

"Oh... I'm married," he said, confused by the attention from this older woman, holding up his hand again to show off his engagement band.

"I know," she stated confidently. "But your wife isn't here right now, and I am, and I think I'm the one you were actually waiting for..."

"I think you, uh... presume too much," Josh said, trying to be polite despite being boldly hit on by this old woman. "And besides, my wife will be here soon."

"Well, you won't be here by the time she arrives. You'll be too busy with me," she stated confidently, her smoky voice betraying no doubt in her prediction, a confidence that surprised the young married man.

"Well, you are bold, I'll give you that. But... I'm not interested," Josh said firmly, still trying to be respectful.

"Oh, nonsense," she said, waving him off. "Of course, you are! It's not often you get a babe as hot as me chatting you up." Not sure if she was joking or if she actually thought she was a total babe, he didn't say anything as she sat down next to him. Before he could speak again, she glanced back towards the tables behind them and spoke up. "But she wasn't so bad either," the older woman said. Josh looked back, only to see Samantha already seated next to a man, conversing with him. "When I saw you turn her down, I figured you had a hunger for something different than what she can offer."

"Again... I'm married," Josh pointed out. "I hunger for, uh... my wife."

"Of course," she said with a small grin, before ordering a whiskey from the clearly amused bartender. It was as if he had seen her before, like this was his regularly scheduled entertainment, watching this old woman shamelessly and futilely hit on young guys way out of her league. And now Josh was the next one in line in her little game. Once she got her drink and took a healthy swig, she turned to face him again.

"I'm Sandy, by the way," she said, holding out her hand. Not knowing what else to do, he shook it.

"Josh," he stated. As he did, he felt her slim finger rubbing into his palm, prompting him to end the grasp quickly.

"You work around here?" she asked, as if all was normal, as if she wasn't just shamelessly hitting on him moments prior.

"I work at the hospital. On the, uh, legal side," he replied. "Wait... were you joking before?" he asked, still confused about this whole thing. But she simply ignored his question and continued.

"Well, I own the porn shop a few blocks over. You know the one, right?" Sandy asked. He certainly did not, but she was undeterred. "I tell ya, we had a few lean years there, but lately, wow... business is booming! Been so busy I've barely had any time to get out and have some fun with a guy. But tonight's the night, and you're the lucky man for me! So, let's enjoy our little date..."

"Sandy, I think you have the wrong idea about me, and..." Josh began.

"No, Josh, I think it's you who's mistaken," Sandy said firmly, reaching over to put her hand on Josh's wrist. The older woman was now facing him more than she just had been, and her exposed cleavage was right in front of him again. He couldn't help but let his eyes drift downward, despite himself, if only for a moment, just to acknowledge what she was doing. Despite his best efforts, he couldn't not look at her expansive cleavage. It was just... it was just right there. She was asking him to look, quite frankly. His eyes became lodged in her cavernous cleavage for what was just a quick moment but felt like a lifetime, the smooth, dark crevasse between her mammoth, tanned, melon-sized tits seizing his gaze. But he did his best to make this stare brief, quick enough for her not to notice... hopefully. She resumed speaking. "You might not believe it quite yet, but you and me WILL be leaving together tonight. Me and you are gonna get to know each other very, VERY well. And by that, I mean we're gonna go to my place, get naked, and have a lot of sex. I mean... a LOT of sex."

"I... I... what?" Josh stammered, shaking his head. Was this a joke? Was he being pranked? How could a woman like her, so much older, and frankly, not exactly a super-babe, presume that a handsome young guy like him would actually cheat on his wife and hook up with her? It was patently ridiculous. If anything, he would hook up with someone like Samantha. At least that made sense. But this... there was no logic to it. Did she really think he was gonna cheat on his wife with a much older woman like her?

"I know it's exciting to think that you're gonna see all of this in the buff," she said, gesturing to her body. "It probably doesn't feel real. But believe it. Your face is going to end up between these..." she said, pointing at her enormous breasts. "Your hands are gonna end up sliding across my hot naked body. Your body and mine will become one. Face it, Josh... me and you are about to become lovers..." At this, Josh had to interrupt.

"NO! I'm married! I love my wife! I'm not gonna cheat... period!" Josh stated, as plainly as possible, trying to dissuade this aggressive older woman. She seemed mildly confused by this, as if this didn't make sense to her.

"Oh! If you're worried about me not knowing what guys like you want... trust me. I know things," Sandy began. "I'm VERY experienced, if you know what I mean," she added, but he still looked at her, baffled. "I mean I've fucked a lot of guys!"

"Yeah, I got that!" Josh stated angrily. "I think you're missing the point, though."

"Here's the thing I want you to understand... I'm not exactly shy," she stated shamelessly, but based on this whole conversation, this wasn't exactly a surprise. "I don't mind ripping my clothes off at the drop of a hat. I mean, I've posed completely naked for the art class at the college, just because I know everyone there will get turned on looking at me. And honestly... it just turns me on to get naked. I mean, I've been sending pictures to porn studios for years trying to get myself out there for the world to see. I just LOVE the idea of men and women getting off thinking about me and my hot body."

"Uh... I..." Josh began, completely flabbergasted. What was going on here? Was he actually being pranked? This was ridiculous.

"And like I said, I work at a porn store. Business is booming, and I'm on the front line, facing down all kinds of horny men. And even though I've been so busy lately, I still get the chance to have my fun," Sandy continued, undeterred. "This drunk college kid came into my store, laughing it up at all the stuff on the shelves, making a joke of my livelihood. So yeah, I rode his dick hard, better than he'd ever had with any college slut, and honey, that boy sobered up fast, haha! He came back a few weeks later, desperate for more of the good stuff from me. But no... he didn't lay another finger on me... that's what he gets for not taking me seriously." She paused and laughed to herself before continuing. "Then there was the time I met with this guy from a parent's council, protesting my store and vowing to shut me down. Well... he wasn't protesting when he came on my tits. And... let's see... these two studly high school guys came in my store as soon as they turned 18, and I let them double-team me in exchange for some free movies. I got a guy to sell me some premium weed in exchange for sucking on my big tits for a few hours. Oh, and one of my employees traded me her ass-slave, who was the wife of the hunky married guy she was hooking up with. So yeah, I had this young, married woman as my ass-slave for a little while, until I got bored with her, which was pretty convenient for whenever I needed a tongue up my asshole..."

"I... I..." Josh stammered at the brazen older woman. Was all this true? This sounded like something out of the porn movies she claimed to sell. Couldn't be... could a woman like her be so active sexually? But he didn't have much time to think on it, because she wasn't done yet.

"And working in a porno shop... trust me, I know things you've never heard of," Sandy began. "Things that'll make your head spin. And I know what men like you like. I tell you, since that whole MILF thing really caught on like crazy a couple years back, we've had those DVDs playing on loop in the store," she stated, seemingly referencing some event or thing that he had no reference point to. What MILF thing? What was she talking about? "I don't know why young men like you have suddenly become so obsessed with fucking women twice their age. Or even older! Like... we have stacks of movies about young bucks like you fucking these smoking hot older women that are old enough to be their mom... or even their grandmother! And you can just tell the guys in the movies are way more excited to be with those women than they are with regular porn stars. And people just love it! It sounds crazy, but that's the shit that flies off the shelves these days. That's why we play them damn near all the time... but I'm not complaining. It pays the bills. And besides... with those playing for me every day, even an old bat like me was able to pick up some new tricks. Trust me, babe... me and you are gonna be porno-fucking, ha ha!"