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40 - Love (The Rematch)

Prompt originally from AetherRoom.club
Created: 2023-09-01
No ratings yet
Description
One bored college guy's quest to kill time over the summer leads to fateful encounter with a flyer at the neighborhood clubhouse. What begins as an innocent invitation to fill the last slot on a tennis team trying to play doubles may end up rocking Jack's world in ways he never imagined...
Tags
tennis, milf, cougar, 3girls, 1boy, mature female, exercise, summer, age difference
Prompt
"Casual Tennis Team Needs a Fourth for Doubles!" the flyer read in hand-written cursive—the kind with a cramped elegance to it which suggested lessons in penmanship from several decades ago. Jack studied the piece of paper, squinting and leaning forward to try and make out the rest of the details. It wasn't much of a flyer at all; just ruled yellow paper from someone's kitchen notepad torn off and tacked on to the clubhouse cork-board. Trying to read the details scrawled beneath the header proved challenging. Outside the chicken-scratch Christmas cards written by his aunt, Jack had scant experience interpreting cursive. Another minute or two of puzzling teased out the letters. "Come see us at the tennis courts around 2pm!" A simple smiley face had been inked at the end of the line, prompting a snort of amusement from Jack. "Well, they're definitely not talent scouts for the US Open," he chuckled. "Might be fun." The activity looked to be another promising entry in Jack's summer-long quest to slay his incredible sense of boredom. Returned from college and stranded without an internship, a part time job at the nearby convenience store had gotten his parents off his ass and left the rest of the week open for a whole bunch of nothing. At first it had been liberating—multiple days off in a row to do nothing but eat junk food and play video games—but all too soon his usual wastrel hobbies lost their luster. Picking up more work would just drain his soul dry in exchange for minimum wage—so what to do with the yawning, ever-stretching weeks until the return to college? To his credit, Jack had given a long list of activities a chance. At first indoors; reading at the library, people watching at cafés, several botched attempts at origami, wandering hobby stores to sniff scented candles, et cetera. Then outdoors, since it felt like a shame to be wasting the weather; walking, hiking, running, disc golf, hammocking, and then swimming, which had brought him to the neighborhood clubhouse in the first place. Each activity held his attention for a scant few days until the beast of boredom ate it, too—and it was back to searching. Tennis struck him as a good next option. Swimming had started to become a snore anyway. Following a return home from the clubhouse and a shower to get rid of all the chlorine on his skin from the day's swim, Jack spent the remaining daylight driving out to purchase a cheap racket and some fresh tennis shoes for the hell of it. It would be nice to play in something that wasn't the pair of beaters he wore to work every day. From the store it was back home and right into dinnertime, then a videogame or two before a long bout of sleep. He greeted Wednesday right as the sun did, running through the dreary paces of his standard morning routine before it was time to clock in for a five-hour morning shift stocking shelves and working the register. In terms of raw boredom, nothing outclassed work, but at least it was boredom that resulted in pocket money. All morning long, Jack stole spare moments between tasks around the convenience store to look up the basics of tennis on his phone. He skimmed through beginner's videos, sifted through internet forum threads—anything to kill time and better-equip himself for hitting the court once his shift was over. Even if it was just casual neighborhood tennis, Jack didn't want to meet a couple of cool dudes on the court and wind up looking like a total chump. The hours passed by in a merciful blur until Jack clocked out with a pre-made sandwich in his hand for lunch and a head full of plans for the afternoon to come. By one-thirty in the afternoon he'd made it home, scarfed down his sandwich, and was shoving his new racket in a cheap drawstring bag for the journey to the courts. Once he'd laced up his fresh tennis shoes—pristine white bodies with shiny red accents—all that remained was an energetic stroll to the clubhouse. That day the weather was in Jack's favor; heavy rains earlier in the week and persistent cloud cover had driven out August's typical merciless heat in favor of a gentle warmth and mild breeze. Passing though the abundant shade provided by the neighborhood's old oak trees made it so Jack barely broke a sweat on his walk. Soon he was back in the sunshine though, traversing the cobblestone path which wandered a short distance away from the clubhouse grounds and up to where the tennis courts lay hidden behind netting and trimmed hedges. The sounds of a tennis match in progress caught Jack's ear even from afar, kicking up his excitement and drawing his footsteps to the second of four courts. Walking up to the gate, his hopes of learning the game from a group of fellow college guys marooned for the summer were dashed in spectacular fashion. Two women were trading volleys on the court, with one sitting on the sidelines—but not one of them was the sort of early-twenties vixen which would have turned Jack's disappointment into a stroke of luck. All three looked to be suburban mothers who had taken up physical activity as a way of trying to shed some of the pudge on their mature forms; the one closest to him on the court had the build of a once-athletic woman fallen from the saddle, while the woman on the sidelines could have passed as a total stranger to physical exertion. The one on the far end of the court was somewhere in between. "Girls~! We have a visitor!" said the woman spectating. At once the two on the court dropped their volley to turn in his direction, and Jack was dealing with three pairs of eyes on him at once. "Are you here to play tennis with us?" the woman on the sidelines asked. Her quizzical expression spread out the freckles beneath her green eyes. "Yeah. I, uh... I saw the flyer," Jack began, trying his best to sound enthusiastic. He couldn't risk any blatant disrespect—all of them looked be different flavors of neighborhood queen-bee, and the last thing Jack needed was an earful from his parents about how his flippant behavior got them uninvited from some weekly dinner social. "If you guys are still looking for a fourth, that is." All three of the women had made their way closer now, the semi-athletic looking one shaking a few lengthy locks of black hair away from her face before she spoke. "We absolutely are, dear. But introductions first: I'm Becca." "I'm Tina," said the green-eyed one. Jack wondered if she'd taken a curling iron to her auburn hair for some other occasion earlier in the day, or just liked to feel fancy for a tennis match. "And I'm just the dumb blonde," the woman who'd been been Becca's opponent said, smiling and laughing right after. "That's Michelle," Tina added. A close-lipped smile betrayed her appreciation for the joke, but Becca had clearly heard it one too many times. "Our resident comedic relief." "Oh, come on now, Becca! Someone has to put a smile on that sour face of yours from time to time!" Tina's smile turned apologetic as her two friends began their light-hearted bickering. "What's your name, honey?" "It's Jack. Nice to meet you, ladies." At his greeting, Michelle and Becca snapped back to Jack's presence. Michelle's eyes were a gentle blue and held his gaze, while Becca's hazel eyes took a moment to rake up and down his form. Jack found himself wondering if a baggy pair of gym shorts and his trusty sweat-wicking athletic shirt was good enough to pass muster. Fashion didn't take a day off for tennis, it seemed; Tina was in a pale yellow sundress cut at the knees and patterned with lilacs, Michelle wore a cornflower blue sports polo paired with a grey tennis skirt, and Becca had chosen black yoga leggings bearing hot-pink stitches along the seams to compliment her neon-pink tank top. Each outfit had its own way of negotiating with their buxom and somewhat doughy figures—each to varying degrees of success. Jack decided the right move was to focus on faces instead of fabric. "So, Jack: can you play?" Michelle asked, breaking the momentary silence. "Never played before, no. But I did spend today looking some stuff up online!" Michelle made a sympathetic sigh, while Tina stifled a giggle and Becca rolled her eyes. Jack bit his lip, unsure whether they'd found his answer funny or pathetic. "Don't worry, we'll teach you the ropes," Becca offered, turning to her friends. "Right, girls?" "Sure thing, sweetie," Michelle said though a faint smile. Tina offered a silent thumbs-up. "Great!" Jack said, trying his best to summon fresh enthusiasm on his face. "Should I hop in and join whoever's winning?" Becca scoffed and gestured towards him with her racket. "You should warm up a little first, big boy. Don't need you pulling a hamstring and skinning your knees trying to keep up with my shots." Tina's apologetic smile returned as she piped up. "You'll play a lot better after a bit of warming up, promise." "Alright, alright," Jack conceded. His eagerness to jump in hadn't earned him any leeway, apparently—so warming up it was. "Where can I stretch out?" Becca nodded towards the bench where Tina had been. "Over there's fine. Michelle and I are gonna wrap up our set in the meantime."... [Click to expand]
"Casual Tennis Team Needs a Fourth for Doubles!" the flyer read in hand-written cursive—the kind with a cramped elegance to it which suggested lessons in penmanship from several decades ago.
Jack studied the piece of paper, squinting and leaning forward to try and make out the rest of the details. It wasn't much of a flyer at all; just ruled yellow paper from someone's kitchen notepad torn off and tacked on to the clubhouse cork-board. Trying to read the details scrawled beneath the header proved challenging. Outside the chicken-scratch Christmas cards written by his aunt, Jack had scant experience interpreting cursive.
Another minute or two of puzzling teased out the letters. "Come see us at the tennis courts around 2pm!" A simple smiley face had been inked at the end of the line, prompting a snort of amusement from Jack.
"Well, they're definitely not talent scouts for the US Open," he chuckled. "Might be fun."
The activity looked to be another promising entry in Jack's summer-long quest to slay his incredible sense of boredom. Returned from college and stranded without an internship, a part time job at the nearby convenience store had gotten his parents off his ass and left the rest of the week open for a whole bunch of nothing. At first it had been liberating—multiple days off in a row to do nothing but eat junk food and play video games—but all too soon his usual wastrel hobbies lost their luster. Picking up more work would just drain his soul dry in exchange for minimum wage—so what to do with the yawning, ever-stretching weeks until the return to college?
To his credit, Jack had given a long list of activities a chance. At first indoors; reading at the library, people watching at cafés, several botched attempts at origami, wandering hobby stores to sniff scented candles, et cetera. Then outdoors, since it felt like a shame to be wasting the weather; walking, hiking, running, disc golf, hammocking, and then swimming, which had brought him to the neighborhood clubhouse in the first place. Each activity held his attention for a scant few days until the beast of boredom ate it, too—and it was back to searching. Tennis struck him as a good next option. Swimming had started to become a snore anyway.
Following a return home from the clubhouse and a shower to get rid of all the chlorine on his skin from the day's swim, Jack spent the remaining daylight driving out to purchase a cheap racket and some fresh tennis shoes for the hell of it. It would be nice to play in something that wasn't the pair of beaters he wore to work every day.
From the store it was back home and right into dinnertime, then a videogame or two before a long bout of sleep. He greeted Wednesday right as the sun did, running through the dreary paces of his standard morning routine before it was time to clock in for a five-hour morning shift stocking shelves and working the register. In terms of raw boredom, nothing outclassed work, but at least it was boredom that resulted in pocket money. All morning long, Jack stole spare moments between tasks around the convenience store to look up the basics of tennis on his phone. He skimmed through beginner's videos, sifted through internet forum threads—anything to kill time and better-equip himself for hitting the court once his shift was over. Even if it was just casual neighborhood tennis, Jack didn't want to meet a couple of cool dudes on the court and wind up looking like a total chump.
The hours passed by in a merciful blur until Jack clocked out with a pre-made sandwich in his hand for lunch and a head full of plans for the afternoon to come. By one-thirty in the afternoon he'd made it home, scarfed down his sandwich, and was shoving his new racket in a cheap drawstring bag for the journey to the courts. Once he'd laced up his fresh tennis shoes—pristine white bodies with shiny red accents—all that remained was an energetic stroll to the clubhouse.
That day the weather was in Jack's favor; heavy rains earlier in the week and persistent cloud cover had driven out August's typical merciless heat in favor of a gentle warmth and mild breeze. Passing though the abundant shade provided by the neighborhood's old oak trees made it so Jack barely broke a sweat on his walk. Soon he was back in the sunshine though, traversing the cobblestone path which wandered a short distance away from the clubhouse grounds and up to where the tennis courts lay hidden behind netting and trimmed hedges. The sounds of a tennis match in progress caught Jack's ear even from afar, kicking up his excitement and drawing his footsteps to the second of four courts.
Walking up to the gate, his hopes of learning the game from a group of fellow college guys marooned for the summer were dashed in spectacular fashion. Two women were trading volleys on the court, with one sitting on the sidelines—but not one of them was the sort of early-twenties vixen which would have turned Jack's disappointment into a stroke of luck. All three looked to be suburban mothers who had taken up physical activity as a way of trying to shed some of the pudge on their mature forms; the one closest to him on the court had the build of a once-athletic woman fallen from the saddle, while the woman on the sidelines could have passed as a total stranger to physical exertion. The one on the far end of the court was somewhere in between.
"Girls~! We have a visitor!" said the woman spectating.
At once the two on the court dropped their volley to turn in his direction, and Jack was dealing with three pairs of eyes on him at once.
"Are you here to play tennis with us?" the woman on the sidelines asked. Her quizzical expression spread out the freckles beneath her green eyes.
"Yeah. I, uh... I saw the flyer," Jack began, trying his best to sound enthusiastic. He couldn't risk any blatant disrespect—all of them looked be different flavors of neighborhood queen-bee, and the last thing Jack needed was an earful from his parents about how his flippant behavior got them uninvited from some weekly dinner social. "If you guys are still looking for a fourth, that is."
All three of the women had made their way closer now, the semi-athletic looking one shaking a few lengthy locks of black hair away from her face before she spoke. "We absolutely are, dear. But introductions first: I'm Becca."
"I'm Tina," said the green-eyed one. Jack wondered if she'd taken a curling iron to her auburn hair for some other occasion earlier in the day, or just liked to feel fancy for a tennis match.
"And I'm just the dumb blonde," the woman who'd been been Becca's opponent said, smiling and laughing right after.
"That's Michelle," Tina added. A close-lipped smile betrayed her appreciation for the joke, but Becca had clearly heard it one too many times.
"Our resident comedic relief."
"Oh, come on now, Becca! Someone has to put a smile on that sour face of yours from time to time!"
Tina's smile turned apologetic as her two friends began their light-hearted bickering. "What's your name, honey?"
"It's Jack. Nice to meet you, ladies."
At his greeting, Michelle and Becca snapped back to Jack's presence. Michelle's eyes were a gentle blue and held his gaze, while Becca's hazel eyes took a moment to rake up and down his form. Jack found himself wondering if a baggy pair of gym shorts and his trusty sweat-wicking athletic shirt was good enough to pass muster. Fashion didn't take a day off for tennis, it seemed; Tina was in a pale yellow sundress cut at the knees and patterned with lilacs, Michelle wore a cornflower blue sports polo paired with a grey tennis skirt, and Becca had chosen black yoga leggings bearing hot-pink stitches along the seams to compliment her neon-pink tank top. Each outfit had its own way of negotiating with their buxom and somewhat doughy figures—each to varying degrees of success. Jack decided the right move was to focus on faces instead of fabric.
"So, Jack: can you play?" Michelle asked, breaking the momentary silence.
"Never played before, no. But I did spend today looking some stuff up online!"
Michelle made a sympathetic sigh, while Tina stifled a giggle and Becca rolled her eyes. Jack bit his lip, unsure whether they'd found his answer funny or pathetic.
"Don't worry, we'll teach you the ropes," Becca offered, turning to her friends. "Right, girls?"
"Sure thing, sweetie," Michelle said though a faint smile.
Tina offered a silent thumbs-up.
"Great!" Jack said, trying his best to summon fresh enthusiasm on his face. "Should I hop in and join whoever's winning?"
Becca scoffed and gestured towards him with her racket. "You should warm up a little first, big boy. Don't need you pulling a hamstring and skinning your knees trying to keep up with my shots."
Tina's apologetic smile returned as she piped up. "You'll play a lot better after a bit of warming up, promise."
"Alright, alright," Jack conceded. His eagerness to jump in hadn't earned him any leeway, apparently—so warming up it was. "Where can I stretch out?"
Becca nodded towards the bench where Tina had been. "Over there's fine. Michelle and I are gonna wrap up our set in the meantime."
Author Notes
The longer Jack remained around Becca, Michelle, and Tina, the stronger their lecherous interest in the young man would become. Between all three of the lonely and horny moms, a silent agreement arose to share Jack's toned, youthful body in a soon-to-be sweaty foursome. Before that happened, though, they were determined to tease Jack into making the first move and forcing him to admit his attraction to older women.
Memory
Jack was an industrious and semi-athletic young man who had returned back to his parent's house for the summer in between semesters at university. A part-time convenience store job filled half of his weeks, but for the other half Jack was engaged in a constant battle with boredom. To fill his time he'd undertaken a litany of different hobbies both indoor and outdoor—none occupying his attention for more than a few days at a time. Starting the cycle anew, Jack had come across a handwritten flyer advertising at his neighborhood clubhouse advertising the need for a fourth person to join a tennis group so they could play doubles. After a day of excited preparation, Jack had appeared at the tennis courts by the clubhouse—only to be greeted by a group of three women who were all twice his age.
Becca, Michelle, and Tina were a tight-knit band of suburban moms who liked to spend their free time playing tennis and trading gossip in a bid to shed some of the weight from their comfortably pudgy bodies. Becca had been an athlete in her college years and retained some of the figure beneath her now-doughier frame, intense hazel eyes pairing well with sharp eyebrows and a back-length waterfall of jet black hair. Michelle had done her best to keep herself fetching through the decades, but the start of menopause had added a decent cushion to her stomach and hips all the same. Michelle had her hair dyed blond on a regular basis to compliment her baby blue eyes, paying top dollar to have it kept in a fashionable bob cut style. Tina had developed a sweet tooth in response to the stresses of motherhood—a fact which her heavy, chubby body put on full display. Tina's auburn hair could always be found kept in ironed curls, a tone or two darker than the freckles which covered her pale face and framed a pair of bright green eyes.
In terms of personalities, Becca had ended up as the classic 'tiger mom'; Michelle had a lackadaisical and humorous approach to just about everything in her life; while Tina was empathetic and care-giving to a fault. For all their differences, the three suburban mothers shared three important commonalities: they were divorced, empty-nesters, and starved for quality sex. In the bedroom, Becca was a dominant with degenerate kinks beyond compare, Michelle was an enthusiastic switch open to anything that promised to be a good time, and Tina became a saccharine submissive liable to smother her lover in affection. All told, it was a bundle of pent-up maternal lust with no foreseeable outlet—until Jack came to play tennis.
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