Cupid's Misfire - Cover

Cupid's Misfire

Copyright© 2025 by sinfantasy

Chapter 2: An Awkward Confession

Erotica Sex Story: Chapter 2: An Awkward Confession - 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 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.

Just as things seemed to be falling into place, a new adventure started for him. While he’d been too busy with work and studies to visit Vicky’s cafe lately, Jake hadn’t forgotten about his secret crush. He came up with an elaborate plan to ask her out on Valentine’s Day, complete with a backup love letter for good measure.

Unfortunately, Sam stumbled upon his first draft and mercilessly critiqued its clumsy wording. She delivered a scathing lecture about the pathetic nature of the letter.

“Man up, Jake,” she’d said. Even a love confession was a mission for her. “Tell her how you feel and then give her the letter, and, for heaven’s sake, proofread it first.”

Jake’s face was burning with embarrassment by the time she was done. While he agreed with Sam’s core message, he couldn’t shake the need for a safety net. So, he penned a more polished version of the letter.

Today was the day Jake had planned to confess his feelings to Vicky. However, Sam, with her impeccable timing, assigned him last-minute chores that dashed his hopes. Without enough time to approach Vicky, he reluctantly left the love letter behind instead. He was certain Sam knew about it, considering her visit to the cafe right after him. Maybe that’s why she was extra hard on him today.

His muscles and joints cried in agony as he felt the flicker of hope. Maybe, just maybe, Vicky would say yes. He knew she was beautiful, intelligent, and captivating. Beneath that dazzling exterior, he wondered, was there a depth he hadn’t glimpsed?

The nagging voice in his head whispered he was deluding himself. Bless his heart, he still believed there was more to her than met the eye.

Jake chuckled at the absurdity of it all. A few months ago, he would never have had such thoughts. Neither would he have mustered enough courage to write a love letter. It was pure luck that he had found a mentor like Sam. It was all thanks to Sam’s tough love.

He closed his eyes with a faint smile playing on his lips. He dreamed about his upcoming Valentine’s Day date.


While Jake surrendered to the dreamless sleep, a new battle raged on for Sam. She was pacing in her bedroom with the red envelope in her hand.

“To my love, Sam,” it read in the shaky cursive handwriting.

While she had held back her anger for the entire day, Jake had still suffered because of her grumpy mood. His confession was not the only reason that triggered her. Last week, she received another wedding invitation in the mail.

The news of her old friends and colleagues finding life partners was deeply unsettling for her. She was happy for them, but each news forced her to look at that aspect of her own life.

Major Reynold was notorious for his string of one-night stands and his dismissive comments about “domestic bliss.” Now, he had found his match in the second half of his life.

The news of Colonel Rockwell’s wedding had left her both surprised and strangely unsettled. It was a fairytale romance that had blossomed during his world tour. The man was never interested in a relationship until he met a kindred spirit in Japan.

Even Jessica, the queen of rebound relationships, had finally found lasting happiness.

Sam, the epitome of self-reliance, a woman who could bring down an entire enemy operation with a single move, felt a pang of something akin to ... wistfulness. She glanced at the ‘Love Letter.’ It invoked a sense of loneliness in her. A feeling she had diligently suppressed for years.

Sam had been in a relationship before, but she had never experienced true love. The fluttering in her heart was a novel experience for her.

She had experienced youthful connections. She was also married for a good five years. While some of her relationships had been more impactful than others, none had left a lasting impression on her. Not even her marriage. It was a comfortable cohabitation. It lacked a vibrant connection or emotional depth.

She had met Albert during one of the army training camps. He was a fellow officer. They had gotten along well. A comfortable camaraderie had developed between them. They decided to get married because, well, it seemed like the logical next step. Both being seasoned professionals, they focused on their army careers more than their married lives.

It was a practical arrangement, a partnership of equals, surprisingly devoid of passion. They were like two ships on a parallel course while they acted as the captains of their own vessels. They spent their holidays together, planned family meets every alternate year, and always kept in touch. They were committed and trusted each other, but their relationship never reached beyond a sense of comfort in each other’s arms.

They had discussed having children, but only as a next logical step. They both knew it wasn’t the life they were looking for. A devastating explosion, an IED blast, left her unable to have children. This ended any further discussions on the matter. When Albert was offered a promotion with the UN Peace Corps, they mutually agreed to divorce. Albert accepted the long-term deployment in Africa, and they lost touch since then.

She returned her attention to the letter, her heart pounding a little faster than usual. It was the first love letter she had ever received. While she might have dreamed of receiving love confessions in her teen years, no one had dared to approach the walking menace of a tomboy at that time. A blush crept up her neck, an unfamiliar sensation for a woman who had spent years suppressing such emotions.

“I want to see how bold you could be!” She spoke to herself with false bravado. As she began to read, a strange warmth spread through her chest.

“Ever since I first saw you in the cafe, my world has turned upside down.” The words seemed to echo in her mind. A stirring sense of longing she hadn’t acknowledged in years. This feeling did not last long, though.

Sam immediately felt her anger boiling to the limit. Even after her long lecture, he had not dared to confess to a person. While she could still forgive him for that, the idiot had not felt the need to address the letter to her. If he could dare to write her name on the envelope, why would he shy away from addressing her at the start of the letter?

She immediately suppressed her analytical mind and continued reading further.

“Being with you makes everything feel more exciting and special. Your laugh always makes me happy and chases away any sadness in my heart.”

At least this was much better than the dry words in his first draft. She suddenly felt shy as a shade of red bloomed on her cheeks again. His words were true, though. She had been smiling more since the day she met him. She was also aware of how sad his life had been after his parents passed. His simple words touched her heart.

She kept on reading further. “You bring colors to my mundane life. It may sound cheesy, but it’s true. You make me want to be a better version of myself—more kind, more thoughtful, more ... me.”

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