Cupid's Misfire - Cover

Cupid's Misfire

Copyright© 2025 by sinfantasy

Chapter 4: Truth and Courage

Erotica Sex Story: Chapter 4: Truth and Courage - 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  

Jake jolted awake the next day. The memory of Sam’s kiss still lingered on his lips. The scene replayed in his head like a broken record. The feel of her breath on his skin was still fresh, and he recalled the way her eyes crinkled at the corners as she smiled. He had kissed Sam. Sam! She was his mentor and a friend. She was the only anchor in the chaotic storm of his life since his parents’ passing. He had crossed a line with her and never wanted to go back.

“What have I done?” He groaned and buried his face in the pillow in shame.

What if she saw me as a kid, a project? I’m still in college, and she’s ... well, Sam is Sam. Strong, independent, and probably old enough to be my mother.” He shuddered at the thought. “But then again,” that playful glint in her eyes was unmistakable.

“I have never felt this way about anyone before. I’m sure she felt it too. It wasn’t a pity in her eyes when she kissed me back. It was something else entirely.”

He tried to swing his legs, but they stayed rooted to the mattress like lead. His body felt heavy and unresponsive, and it ached all over as if a herd of grumpy cattle had trampled him. Damn his competitive spirit. The hike had been brutal, but he also felt a different kind of exhaustion. A soul-deep weariness that had nothing to do with sore muscles. A sinking feeling rose in his stomach as he realized he had started with a lie. It followed with a potent mix of fear and longing.

“To think,” he muttered. “I was going to impress her with honesty. What a joke.”

Rather than losing himself amid his own confusion, he needed to get out. He stumbled out of bed with effort. He walked like a zombie on his way to the kitchen. A steaming cup of coffee did not help to cheer him up. An overwhelming feeling of guilt washed over him as he thought of facing Sam again.

“This is all my fault,” he declared to the empty kitchen. “I should have just told her the truth from the beginning.”

The rest of the morning was a daze of agonizing introspection. He replayed every stolen glance, every fleeting touch. He even dissected every word that had passed Sam’s lips to figure out their meeting. Was it just a mad moment? A single slip of judgment? He desperately wanted to believe so, but memories of Sam’s laughter said otherwise. The way her eyes sparkled with that mischievous glint refused to be silenced. He should have given it a deeper thought before playing along with the mistaken confession with Sam.

“Oh, Jake,” he groaned. “You’re way over your head.”

The familiar rumble of Sam’s truck broke the silence at that moment. He should go out and greet her and offer an apology for his lie about the love letter. The thought of facing her was utterly overwhelming.

Now that things had progressed beyond his wildest imagination, could he pretend nothing had happened? He wanted to bury his head in the pillows and pretend he was dead.

“Run away, Jake, run away!” He urged himself, but his feet felt glued to the floor.

Sam knew he needed recovery time after the ordeal she had pushed him through. She looked at him standing in the kitchen with a gloomy face. She wondered what was going through his mind now. One thing was clear though: he needed space.

Sam had a list of supplies to pick up in town. She left him to his thoughts and drove away. Suddenly, a thought occurred to her. She knew what was bothering him. She decided to visit the cafe on the way and address that problem.

The events of the previous day continued to play on a loop in her mind. That kiss ... it had shaken her to her core. She had pushed him and tested his limits. She had enjoyed watching him rise to the challenge, but she hadn’t expected that. The sudden wave of emotions, her body’s reaction to his touch ... It was both exhilarating and terrifying.


Sam stopped by Vicky’s cafe to pick up her caffeine fix and a slice of blueberry pie. She sat down by the window and spent a good amount of time chatting with Thelma.

Vicky was dying to know what had happened after her “Love Letter” prank. Jake hadn’t been back since that day. She decided to ask Sam if he was being punished.

“Colonel Walker,” Vicky greeted Sam with a usual charming smile. “Enjoying the view?”

“It’s Lieutenant Colonel, but you can call me Sam,” Sam replied dryly.

Vicky blinked in confusion but continued with a smile. “How is Jake doing as your assistant? It must be fun keeping him on his toes, right?”

“Oh, it is,” Sam replied with a playful glint in her eyes.

Vicky leaned in closer and whispered, “I hear you’ve been making a real man out of him.”

Sam raised an eyebrow with interest. “Oh? That’s an interesting choice of words, young lady.”

Vicky’s smile faltered. “I mean, he has gained some muscle since he started working for you. He also looked more confident. It’s impressive.” She tried to clarify her words.

Sam chuckled in a low rumble that made Vicky shift uncomfortably. “He’s a good chap as he is,” she said. “I wouldn’t try to change anything in him.”

“Oh, I heard quite the opposite, you know.” Vicky bluffed with a mischievous glint in her eye. “He’s practically living in fear of your next challenge.”

Sam laughed. “He’s a bit too eager to please, but I don’t see even a hint of fear in him.”

Vicky rolled her eyes. “He is quite infatuated with you, Sam.”

The smile on Sam’s face faltered slightly. “Why do you say that?”

Vicky leaned forward and whispered, “Let’s just say I have my sources.”

She chuckled at Vicky’s attempt to be mysterious. “And what do your sources say?”

Vicky’s voice sank to a conspiratorial whisper. “I heard he was going to propose to you.”

Sam chuckled low and in amusement. “What does this have to do with you, Vicky?”

Vicky stuttered over Sam’s blunt words. Her usual tactics were not working. “Oh, nothing! Just. observations. I’m a keen observer of human behavior.”

Sam gave a slow, predatory smile. She had guessed it already, but it was good to hear her confession. “Indeed, you are. Now, about that love letter.”

Vicky froze as her smile vanished. “Love letter?”

Sam spoke in a silken whisper. “The one addressed to ‘My Love, Sam.’ The same one you so graciously left for me.”

Vicky was caught, but she tried to play innocent. “I did no such thing.”

Sam continued. “Don’t play games with me, Vicky. That letter was meant for you, wasn’t it?”

Vicky was cornered and had no choice but to confess. She explained how it irritated her that Jake hadn’t even put her name on the letter and her subsequent prank to teach him a lesson. Sam listened to her confession patiently with a smile.

“You know,” Sam said with amusement, “I always suspected you had a mischievous streak. Though I must admit, I’m starting to think your methods are a bit. drastic.”

Sam watched Vicky with keen eyes. There was no remorse or sadness on her face. At best, she was simply disappointed that her prank had failed.

“Don’t you think you might have been a bit too hard on him, Vicky?” Sam asked.

Vicky fidgeted in her chair. “Of course not! I was just trying to teach him a lesson.”

“Pitting him against me?” Sam raised an eyebrow. “Jake is a kind and capable young man. He deserves someone who understands his feelings and appreciates him for who he is. It would have been much better if you had refused him outright.”

Vicky’s face fell at the realization that she might have overstepped.

Sam relaxed back in the chair. “Since you included me in this prank, I might as well return the favor. Look behind you. Thelma has a nice surprise waiting for you on the display board.”

Vicky’s eyes widened in horror as she turned her head. Thelma had removed the daily specials from the board. Now it showcased a collection of Vicky’s most embarrassing moments. Right in the center was her picture with her face planted in a slice of blueberry pie. The next photo showed her hilariously disastrous attempt to ride the mechanical bull at the county fair. Even more embarrassing were the pictures of her making faces. It even featured her in the Halloween Snow White costume, a disastrous failure she wanted to erase from her memory. The board was topped with a neatly lettered caption: “Our dear, Vicky.”

“How. How did you get these?” Vicky stammered, speechless.

Sam shrugged with a mischievous glint in her eyes. “Let’s just say I have my ways.”

Vicky stared, mouth open, at the board. She realized Sam had turned the tables and given her a taste of her own medicine. The joke may have been laughable, but Vicky was totally rattled. She stole a glance at Thelma, who was desperately holding back laughter. The crowd near the display board was getting thicker now, eyes scanning with amazement.

She couldn’t take it anymore, even with her usual bravado. Vicky turned and ran towards the kitchen, a blush burning her cheeks. The laughter of the patrons followed her retreat.

A flicker of pity replaced the amusement in Sam’s eyes as she watched Vicky retreat. Under the playful teasing, Vicky was a lonely girl crying out for attention. Her schemes were a cry for connection, a misguided attempt to break through the barriers she had erected around herself.

Sam exchanged a knowing look with Thelma. They shared a genuine laugh at the prank they had pulled off. Her mission was done, and she had a newfound understanding of the girl behind the facade. She left the cafe with a lingering smile playing on her lips.

Unknowingly, Vicky had handed her something unexpected, something real. Now Sam had to verify Jake’s feelings on this matter.


Sam thought over the events since yesterday as she drove back to the farm. Were his feelings for her true, or was it just a fleeting infatuation? A defensive response to Vicky’s prank? A tremor ran through her as she remembered the kiss. Its intensity still echoed in her senses. She chuckled as she recalled his scared expression after his impulsive kiss.

She had always liked his open-minded, honest approach. It wasn’t just a physical attraction for her. She felt a deeper stirring within her that she hadn’t felt in years. Could this be real? He was just a young man, still finding his way in the world. Could he be attracted to her, a woman twice his age? The thought both thrilled and terrified her.

Self-doubt crept in. Was she being selfish? Was she leading him on? Could this be anything more than a fleeting summer romance? What if she hurt him? What if she stifled his growth? These thoughts swirled in her mind to dampen the joy she felt.

She remembered the way he looked at her. The raw vulnerability in his eyes, the way he seemed to hang on to her every word. She knew, deep inside, she was right. She had read it in his eyes. The way his hand shook when he reached out to touch her. He didn’t know it yet, but he was falling for her. The realization was shocking enough, and she felt weirdly hopeful.

She had always led the charge and had always been the one in control. Her past relationships had often felt more like partnerships than passionate affairs. A comfortable companionship, a sense of duty, a shared life built on mutual respect and admiration. What she felt about Jake was different.

An odd feeling of vulnerability and this thrilling feeling of being out of balance had led her astray. Jake was teaching her to let go. She hadn’t allowed herself to be vulnerable in years, but it was time for her to trust again.

She found herself wanting to protect him, shielding him from the world. While she could do all that, it wasn’t the right thing to do. This was his journey to navigate. He needed to find his own words, to express his feelings in his own way.

As she pulled into the driveway, a slow smile crossed her lips. This time, the smile held a touch of tenderness, a hint of excitement for the unknown future, and a mischievous glint of anticipation. She wouldn’t tell him she knew about the letter. Let him come to her and confess in his own time. She would wait for him, patient and understanding. She was ready to embrace whatever came next.

Besides, she was quite curious to see how long it would take him to figure it out.


The sun cast long shadows across the farm as Jake stood near the old barn. His muscles were still sore and cramped up. What made this rest day was the overwhelming guilt he had been feeling since morning.

Living a lie was so not like Jake. He couldn’t continue this charade any longer. While Vicky may have set this ball rolling with her prank, he was the one leading it now. When Sam had agreed to go on a date, he had only considered it as a challenge to make her happy. This budding relationship and spark of something more was beyond his expectations.

He couldn’t build this relationship based on lies. If Sam ever finds out the truth on her own ... No, he was not willing to risk it. He had to come clean and confess.

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