Cupid's Misfire

Copyright © [2024] [SinFantasy]. All rights reserved. No part of this story may be reproduced, transmitted, stored, or reused, in any form or by any means, electronic or mechanical.

All persons engaging in any sexual activity are at least eighteen years of age.

While I've diligently edited this story, some errors may persist.

This story is an entry in the Literotica Valentine Day Story Contest 2025.

Note:

This is a slow-burn story. It follows the theme of character growth, romance, and finding true love. It will take a while before we reach the steamy bits.

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~ Cupid's Misfire ~

Chapter 1 - The Love Letter

Vicky glanced up from the register to the chiming bell of the dinner entrance. A practiced smile graced her lips as she saw Jake standing awkwardly by the door, his gaze darting everywhere but at her.

It had been two months since his last embarrassing visit. Boy, oh boy, had he changed. Gone was the gawky teenager of the past. He had grown to be a man with broad shoulders and a jawline that could cut glass.

"Well, look who's finally back from wherever he's been," she murmured to Thelma with feigned surprise.

Thelma snorted, "You'd think you'd never seen him before, the way you're practically drooling."

Vicky pretended to be shocked. "What? Me? Interested in... him?" She let the question hang in the air but raised her eyebrows as she looked at him again.

Jake took his usual seat in the corner, the 'loser's corner,' as Thelma secretly called it. It was the furthest from the window, the coldest spot in the dinner. Jake was sweet and harmless. He used that spot to keep looking at Vicky standing at the counter.

"Damn, girl," Thelma muttered, squinting at Jake. "Did he go on a jungle expedition or something? Looks like he wrestled a bear."

Vicky stifled a giggle. "He does look... different. Stronger." She let her gaze linger on him. Her eyes shone with a twinkle of amusement. Jake was socially awkward, but that was two months ago. Now, there was a hint of... something. Confidence? Maybe.

Thelma saw right through her. "Don't you dare," she grabbed Vicky's hand. "He's a good guy. Almost too good for you."

Vicky feigned innocence. "Of course not, Thelma. I just... I'm curious."

Curious indeed. Vicky thrived on the attention of all the boys her age and some older. She loved the thrill of the chase but never committed. She enjoyed keeping them at arm's length and dangling them along.

Vicky collected Jake's usual order, a coffee and a blueberry muffin, and carried it to his table. He fidgeted under her gaze, still trying to look away from her. His fingers nervously ran through his hair, the habit he had picked up whenever Vicky was close.

"The usual," she drawled in her silky voice.

"No muffin today," he mumbled. His eyes stayed focused on the old wooden tabletop.

"Are you cutting on carbs or something?" she asked. Her arms reached to touch his biceps, but she stopped herself in time. It would be too forward for Jake.

"Huh, no, no, carbs are good. I... I..." he stammered as he looked at her.

"Suit yourself," she leaned closer and whispered. Jake could feel her breath fanning his cheek. "Though, I must say, a man with muscles like yours could probably afford a few extra carbs."

Jake's eyes widened. "I-I, uh..." He stumbled over his words, and his face flushed crimson.

Vicky pulled back a little with a mischievous glint in her eyes. "Just teasing," she said, but the intensity of her look said otherwise. "But seriously, what's up? Did our retired Colonel Sam put you through a boot camp routine on her farm?"

Jake shook his head "No, no, nothing like that. It's just..." He was still flustered and could not find the right words to explain.

Vicky raised an eyebrow, her eyes sparkling with amusement. "Just what? Spill the beans, Jake. I'm dying to know."

He avoided her gaze, running a hand through his hair. "I, uh, I'm trying to... impress someone."

Vicky's smile grew wider. "Oh really? Who's the lucky lady?"

Jake looked up at her, his eyes wide with a mixture of fear and hope. "Well, uh... I was hoping it might be..."

A new customer arrived to pick up their to-go order, interrupting his confession.

Thelma was busy, so Vicky had to deal with the impatient man. "I will be right back with you," she said, returning the muffin to the counter with a playful glint in her eyes. She couldn't help but steal another glance at Jake while she rang the order.

Jake sighed and murmured, "I was hoping it might be you... dammit." He stole a glance at Vicky from the corner of his eye, still avoiding direct eye contact.

He had meticulously planned this visit. Alas, his confidence evaporated at the first sight of this brunette beauty.

Vicky had a naturally seductive smile, and her dusky skin glowed under the pale yellow light near the counter. She also had the tact to disarm the picky customer, like the one she was dealing with now. Jake felt uncomfortable with her flirty talk, but he could see the man mellow down in her presence.

"When are you asking her for a date?" He heard a curious voice of Thelma, who had approached him unnoticed.

Jake nearly choked on his coffee. "Aah... umm... This Valentine's Day?" he stammered in response.

Thelma gave a hearty laugh, "Valentine's Day? You're aiming high, boy! Vicky's probably got a mile-long waiting list for the day."

He groaned, "I know, I know, but... I think she might actually say yes to me."

She raised an eyebrow. "Oh? What makes you think that?"

He shrugged, "I don't know. She looked more... umm... approachable today."

She leaned closer to him. "Approachable, huh? Or just bored with the usual suspects?"

He blushed. "Aah... I... I don't know, but I'm going to try anyway."

She grinned at him. "Good luck, soldier. Don't chicken out at the last minute, and, for heaven's sake, don't wear anything nerdy."

Jake chuckled, "I wouldn't dream of it."

Thelma winked, "Good boy. Now go get 'em, tiger!" She gave him a thumbs-up and moved to the next table.

He sighed as he thought of how he was going to approach Vicky.

Before he could calm his nerves, his phone beeped with a message tone. "Get this list from the hardware shop. I am stopping for a quick snack and will pick you up from there."

"Damn..." he cursed under his breath. It was Sam, his employer, with her never-ending list of chores. She had given him a thirty-minute break from their shopping trip, and not even ten minutes had passed before she gave him another task.

He sighed and looked at Vicky, who was still charming the customer. "It would take a while to get the hardware list packed," he mumbled. He did not have enough time to wait for Vicky. Sam would be here soon, and he would never dare to talk to Vicky in Sam's presence.

Dejected, he pulled out the love letter he had drafted carefully over the last week. It was his backup plan, a last-ditch effort to express his feelings. He kept his bills and the letter with a generous tip at the table. He took one last lingering look at Vicky and then turned to leave.

***

Vicky watched Jake leave, a flicker of irritation passing over her. After all, she had deliberately stretched out the conversation with the customer. It was her show, savoring the moment of making Jake squirm with anticipation.

Thelma had given her heads up; Jake was finally ready to make his move. Vicky wanted to prolong that moment a bit longer. She wanted to see him build up his courage, to watch the uncertainty dance in his eyes. His abrupt departure left her feeling a strange sense of anticlimax.

Vicky wrapped up her talks with the customer and sent the happy man on his way. She then walked up to the "loser's corner" to pick up the cup and bill. A small, square object caught her eye as she reached for the cup. It was a pink piece of paper, neatly folded and tied with a red lace. A love letter.

Her smile quickly faded as she unfolded the paper. The writing was as neat as it could be with a hesitant hand. It was indeed a love letter, but with no salutation. No "Dear Vicky," or even a simple "To Vicky." It was just a rambling declaration of affection that ended with a hesitant signature: "Jake."

A strong wave of disappointment washed over her. Not only had he not dared to approach her directly, but he hadn't even dared to address the letter properly. The playful teasing she'd been enjoying turned into a simmering annoyance. How dare he leave her hanging like that?

As Vicky pondered how to teach Jake a lesson, Sam entered the cafe. Samantha "Sam" Walker, a formidable woman who had recently taken over her family ranch, was a force to be reckoned with. Vicky vividly recalled a scene from two months ago when a group of hulking bullies had tried to harass Sam.

Vicky remembered Sam that day. She was wearing a full-sleeved dress that concealed her powerful physique. "She looked like a harmless housewife," Vicky thought, "a perfect target for those idiots."

Jake had stepped forward to help Sam with his hero spirit and a burst of misplaced courage. "Why are men so stupid?" Vicky had thought about the absurdity of Jake's actions.

Jake had puffed out his chest and tried to look tough. "Hey! Back off," he had warned. However, the moment the bullies turned their attention to him, his bravado crumbled.

"What's this little wuss going to do?" One of them sneered. They closed in on Jake.

"Hey! I'm warning you!" Jake stammered, his face turning crimson. The bullies just laughed.

Vicky remembered watching the exchange with a mixture of amusement and disbelief. Jake, the so-called knight in armor, was about to get his ass kicked. "Oh, this will be interesting," she had thought.

Sam had watched the exchange with a hint of amusement in her eyes. She didn't intervene immediately, allowing the spectacle to unfold.

The dragged exchange ended with Jake bruised and humiliated. He did not give up, though. To the utter surprise of all the spectators, he stood up again.

Sam had seen enough. She finally stepped in. "I suggest you leave," she hissed. Her voice carried an ominous tone, spelling the doom for the bullies. "Now."

The bullies hesitated when they should have run. Sam dispatched them with a few well-placed kicks and punches delivered with chilling precision. She had left them sprawled on the pavement in a few seconds.

Jake had stood frozen in place with an expression of embarrassment and awe. "Talk about a double whammy," Vicky had thought. "First, he fails to protect someone he tried to defend, then he gets rescued by the very woman he was trying to impress."

Sam was a retired Lieutenant Colonel in the Marines, a woman who wouldn't tolerate any nonsense. Vicky would have enjoyed Jake's embarrassment more if Sam had also berated him. She later heard that Sam had hired Jake as her farmhand. A decision Vicky found oddly amusing.

A devious idea sparked in Vicky's eyes. A slow, predatory smile spread across her lips. She carefully carried the love confession to the counter. She slipped it into a red envelope, the kind used for Valentine's Day cards.

Taking a deep breath, Vicky meticulously addressed the envelope. "To my love, Sam," she wrote in elegant cursive, deliberately imitating Jake's slightly awkward handwriting. She even added a small heart at the end.

Vicky glanced around at the diner with a mischievous glint in her eyes to make sure no one was watching. Then she approached Sam's pickup truck, a gleaming silver beast with an aura of power. She carefully placed the envelope on the driver's seat.

Vicky imagined the scene: Sam reading the love letter from a boy half her age. The bewildered expression on her face and arch of eyebrows. Jake, poor, oblivious Jake at the receiving end of her fury. Vicky could almost hear his frantic apologies and stammering explanations. The awkward silence and chaos, the potential for a truly epic misunderstanding... It would be so much fun.

A triumphant smile spread across Vicky's face. She had to admit, this was the best prank she had ever pulled. With a satisfied sigh, she returned to the cafe. If only she could see the fallout of her little masterpiece in real-time.

***

Lieutenant Colonel Samantha "Sam" Walker, USMC (Ret.), was having a typically efficient day. The discipline and focus of seventeen years of service clung to her like a second skin, even out of her uniform. It had been months since she'd traded her combat boots for cowboy variety, and she was still adjusting to the civilian pace of life.

It had been a long time since she had left this town. The only reason she had returned was to sell off the family ranch. A past she thought she was ready to leave behind.

Her father had always marched to his own beat and had envisioned a post-retirement haven here. He had spent his last few years revitalizing the old ranch. However, the new glory was short-lived. The property fell into disrepair after his passing a few years ago.

Sam found it hard to sew the emotional ties. Both cherished and bittersweet memories clung to every corner of the land. In the end, she decided to repurpose the place and transform it into a thriving farm. She was not interested in farm animals and annual crops. Her goal was much more ambitious: orchards and state-of-the-art greenhouses. It was a practical business idea and a continuation of the family legacy.

The transition from the structured world of the Corps to the unpredictable rhythms of civilian life had been... challenging for her. The silence was deafening after years of constant hum of activity, camaraderie, and shared purpose. Now she was grappling with mundane tasks like fence repair and supplier negotiations. It felt like a demotion, a waste of her strategic mind and years of honed decision-making. At the same time, it gave her a sense of peace and purpose.

She ran through her mental checklist, a habit deeply ingrained. The hearty meal, a mountain of protein and veggies, barely registered as a snack for the woman built like a tank. Years of grueling physical training had sculpted her body—broad shoulders, powerful arms, a core of steel. Yet beneath that formidable exterior lay an unexpected grace.

Her long black hair was confined in a tight bun, another habit from her military life. When set loose, it framed her face with a surprising softness. Her stormy eyes held a quiet intensity. A woman capable of dismantling an enemy stronghold or fixing a leaking faucet with equal efficiency.

Even at the age of forty, duty always came first for Sam. She was raised in a household where strength and independence were paramount. Her father was a decorated Marine legend, and she had always tried to be like him—a leader and a warrior. She was deeply competitive, just like her father, and had excelled at almost everything. It took her only five minutes to clean her plates and leave the cafe.

A flash of red caught her eye as she approached her pickup truck—an envelope addressed to her. "What in the...?" she growled. A reflex honed during countless security drills almost had her discard it until she saw the writing. Something about the familiar chicken scratch of the handwriting stopped her cold. It was from Jake.

A tremor ran through her, a jarring reminder of vulnerability she'd thought buried a long time ago. A cold and furious anger flared within her shortly after. "Damn that kid," she muttered.

She wasn't ready to deal with past emotional baggage, especially not now. Yet Jake had managed to stir something deep inside her. A dormant emotion threatening to disrupt her carefully constructed order. As she looked at the envelope, a fleeting image of the young man flashed through her mind.

He was always eager to please and tried his best at everything. He was driven by an insatiable desire to prove himself, just like a younger version of herself. A faint smile touched her lips. She couldn't deny watching him adapt over these past months had been... interesting.

She tucked the envelope under the seat, determined to deal with it later. First, she had to pick up Jake and make him work extra hard for his audacity.

Sam slid behind the wheel of her pickup truck and started the engine. She caught the sight of Vicky, perched behind the counter, waving at her playfully. Sam acknowledged her with a curt nod.

"That little minx is up to no good," she whispered as she pulled away from the parking lot.

Jake was waiting for Sam by the hardware store. He had all the supplies packed and ready. He looked like a kicked puppy.

Sam felt a surge of amusement. She was aware of his confession plans, but she had never expected the woman of his dreams would be herself.

"Are you ready to work?" she asked with a voice devoid of emotion.

Jake jumped, startled. "Y-yes, Sam," he stammered and scrambled to his feet. "Just waiting for you."

Sam raised an eyebrow. "Waiting or daydreaming?"

Jake flushed. "No, Sam. Just... thinking."

"Thinking about what?" Sam pressed.

Jake squirmed under her sharp gaze. He hesitated and blurted out, "About... about... things."

Sam chuckled. "Things, huh? Well, let's get those things done. We've got a lot of work to do."

She turned and walked towards the hardware store to make the payment while Jake started loading the supplies into the truck.

Sam couldn't shake off the feeling that something was amiss. There was an unspoken undercurrent around the letter that she couldn't quite pinpoint. The image of Vicky's playful smile kept intruding on her thoughts. Along came the unsettling tremor that had run through her upon seeing Jake's handwriting.

Her carefully constructed order was about to be disrupted.

*****

Chapter 2 - An Awkward Confession

Jake sprawled across his bed, utterly spent. Another grueling day at the farm, "From the Field to You," had left him aching in places he never knew existed. The past two months had been full of surprises for the young man. To the point, he had questioned every life choice that had led him here.

"Two months ago," he muttered, "I thought life was all about... well, life." His chuckle sounded a bit strained.

"Now it's just about surviving Sam's farm." He could almost hear her voice booming in his ears. "No excuses, Jake. Efficiency is key, and don't forget to hydrate!" He imagined her raising an eyebrow—that amused disapproval she gave him whenever he slacked off. He was getting the killer workouts and top-notch life skills training from Sam, and she was even paying him for it.

It all began at Vicky's cafe, a place he frequented to meet the captivating beauty who stole his heart. However, fate had something else in store for him. He had met Sam, a formidable ex-Marine turned farmer. His attempt to help her had been less than stellar, leaving him more embarrassed than ever before.

To his surprise, Sam sought him out the very next day and offered him a job at the ranch. Despite having no real financial need, Jake eagerly accepted. He had been isolating himself in his house after losing his parents, and this was a welcome change. So began his new life under Sam's demanding tutelage.

The first week on the farm was pure torture. His muscles screamed in protest under Sam's relentless training regimen, disguised as work. By week two, he was ready to show the proverbial white flag of surrender. "No excuses, Jake," Sam's voice echoed in his mind again. Then something remarkable happened. His body adapted, his stamina increased, and he learned to follow Sam's orders without question.

The benefits went beyond just physical fitness. He also thrived in his studies at college. All thanks to Sam's support and guidance. A friendship blossomed between them as they spent countless hours working the farm together. He even saw glimpses of a softer side to Sam, like the times she ensured he ate properly or offered him a massage after particularly grueling days. "You need to fuel your body," she'd said as she handed him a plate of sauteed vegetables. "Don't forget to stretch," she'd added. Her voice was surprisingly gentle during those times. He'd felt a strange warmth spread through him.