Cupid's Misfire - Cover

Cupid's Misfire

Copyright© 2025 by sinfantasy

Chapter 1: The Love Letter

Erotica Sex Story: Chapter 1: The Love Letter - A mischievous prank leads a young man to find his true love!

Caution: This Erotica Sex Story contains strong sexual content, including mt/ft   mt/Fa   Romantic   Heterosexual   Fiction   Humor   Military   Cream Pie   First   Massage   Oral Sex  

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.

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