Cupid's Misfire - Cover

Cupid's Misfire

Copyright© 2025 by sinfantasy

Chapter 5: Perils of Love

Erotica Sex Story: Chapter 5: Perils of Love - 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  

Today, Jake woke up bursting with energy. His body still ached, but his movements were fluid. He could still feel Sam’s lingering touch all over his skin. He started with the coffee while waiting for her.

Sam walked in as the coffee aroma waffled the kitchen. Rather than the usual ponytail, her hair flowed freely over her shoulders. This new look gave a tender touch to her dazzling beauty. There was a new spark in her eyes, something he had never noticed before.

“Morning, rookie,” she purred. Her voice sounded like a low rumble that sent a jolt of anticipation through him. “Did you have any pleasant dreams last night?”

Jake blushed at her direct attack. His voice was still raspy from sleep. “Y-yeah. I did.”

Sam strolled over to the table, her eyes drifting to his bare legs. A playful smile played on her lips. “You were quite a handful last night,” she teased.

Jake’s cheeks reddened with embarrassment as he recalled Sam’s hands tracing across his length. “Sorry if I was too much,” he murmured. His eyes focused on the swirly coffee in his mug.

Sam gave a hearty laugh. “Don’t be silly. I liked the fact that you were too much.”

She did not give him a chance to hide anymore. She stretched across the table to hold his hand. A jolt of static electricity coursed through him. He met her gaze. There was not a hint of regret on her face. Instead, he could see a playful spark that ignited a fire in his belly.

“I haven’t felt that turned on in a long time,” she confessed in a husky voice. “You’re a real fire starter, Jake.”

His chest puffed out with pride. So much self-doubt had consumed much of his life, and Sam’s playful words busted his ego. For the first-timer, it was praise he’d never anticipated receiving.

“I am glad you liked it,” he whispered over the faint hum of conversation.

Sam squeezed his hand. “Oh, more than you know.”

She leaned across the table to whisper in his ear. “Let’s just keep that little secret between us, shall we?”

Jake nodded eagerly. He could feel the residual effects of her touch that ignited his senses again.

Sam backed away before he could get any ideas. “I’ll be out of town for the next two days. One of my old friends, Reynold, is getting married. I simply can’t miss the opportunity to meet my friends at the gathering.”

Jake’s face fell a little. “Oh, I see.”

“Don’t worry,” she comforted him with a quick hug. “It’s only for a few days.” She winked at him, “Besides, it’s a perfect opportunity for you to test the new confidence you have acquired.”

She slid her truck keys across the table to him. “Take Vicky out on a date. Prove to her what you’re capable of.”

He took the keys with determination. “I won’t let you down.”

Sam looked at him suggestively. “I know you won’t.”

Jake took Sam to the airport later that afternoon. She pulled him in for a long, smoldering kiss. Long enough to make him understand what to expect on her return. “Be good, and remember. You need to be assertive with Vicky.” She whispered against his lips.

“I will,” he promised. His voice had turned hoarse with arousal.

Sam pushed off from him with a playful smirk. “I am counting on that.”

With another wave, Sam disappeared through the gate. Jake stood there with a fire burning inside, already anticipating her return. He had to focus, though. After all, he had a date to attend.


Jake exited the airport and went straight into the cafe. He wanted to ask Vicky out today. It was not because Sam had asked him. He was doing this for himself.

He stepped inside the coffee shop with confident steps. He looked around before taking a seat near the door. This seat directly faced the counter. Unlike his usually shy demeanor, he was looking straight at Vicky.

Thelma was surprised when he did not take his usual ‘looser’s corner’ as she called the place. “Someone’s got spring in their step today,” she shared her keen observation with Vicky.

Vicky nodded at her and walked over to his table. “Hi Jake, you seem happy today.” She tried to shake him a bit.

He took a deep breath to bring forth all the confidence he had been building since morning. “Vicky,” he spoke in a steady voice. “Let’s hang out at your favorite burger joint tonight. I will pick you up at seven.”

Vicky blinked at him. She wasn’t ready for this confident version of Jake. “Tonight? I don’t know ... It’s too sudden.”

“It’s kind of a spur-of-the-moment idea,” he tried to reason with little conviction. “I would like to know you better.”

Vicky hesitated, trying to come up with an excuse. “I ... well...”

“Look,” he interrupted gently. “I know your shift ends at six thirty. I could make this a standing invite for tomorrow, but where’s the fun in that?”

Vicky looked at him. A slow smile spread across her face. “All right then,” she said. “See you at seven.”

Jake nearly leaped out of the booth. He actually did it! It was a small victory, but it held a monumental achievement for him.

Jake reached the cafe in time to pick her up for the date. His nerves were on edge in anticipation of the evening. Feeling self-conscious, he checked himself in the rear-view mirror once. He ruffled his hair and smoothed his shirt before entering the cafe.

Vicky was ready for their date. Dressed in a simple pair of jeans and a t-shirt, she had light makeup on. She looked far too elegant for someone who had just completed her shift.

“You look amazing,” he stuttered. His attempt to sound cool had failed miserably.

Dinner was surprisingly fun. Vicky was witty, and her laughter was contagious. He liked her company. He tried to be funny but struggled to keep up with her enthusiasm.

Everything was going great until a towering figure walked in. He had an arrogant grin plastered on his face. He walked toward their table, his eyes lingering on Vicky.

“Oh, hey Mike,” Vicky greeted her ex-boyfriend. She did not bother to introduce him to Jake and engaged in conversation with him.

Mike took a seat beside her as he launched into a series of self-deprecation jokes. Vicky also joined in his laughter while completely ignoring Jake’s presence.

Jake could tell this was a well-planned setup. It only made Jake squirm inside. He wanted to leave right now. He stood up. “Vicky,” he said. “I think I’ll get some fresh air.”

Vicky did not bother to respond. Then he remembered Sam’s words: “Be assertive.” Suddenly, he did not want to let this prank slide.

He leaned towards her. “This was ... this was fun,” he whispered while his heart was racing. He then grabbed the back of Vicky’s head to turn her face and kissed her. What he lacked in experience, he backed with passion. Vicky’s eyes went wide with shock as she felt Jake’s tongue breaching her lips.

“Thank you for the wonderful evening,” he said with a bit of ire as he walked out of the restaurant. He felt shivers run down his body as the adrenaline rush subsided. Ha! He did it! While his actions were impulsive, he had stood up for himself.

He had just gotten in his truck when Vicky ran out of the restaurant. She was out of breath, and her face carried the same shocked expression. “Jake! Wait!”

He pulled over with a curious smile.

“I ... I’m sorry,” she stammered. “I didn’t mean to. He just walked in ... I don’t know.”

He opened the truck door. “Get in.”

Vicky climbed in. Her face showed her panic as Jake drove straight to her home. While the prank was not intentional this time, she could not pass the opportunity when Mark had shown up. She knew she had screwed up big time.

“When will I see you again?” She asked while trying to sound cheerful.

“I will let you know,” he said dismissively.

Vicky looked as though she could cry. He hesitated. “Look,” he said, “I really like you. A lot. It’s fine if you do not feel the same way, but I don’t like mind games.”

Vicky’s smile returned in an instant. A mischievous glint came into her eyes. “Pick me up tomorrow at seven,” she said playfully. “I will make it worth your while.”

Jake thought for a moment before nodding. “We’ll see about that.”

Vicky’s eyes sparkled. “Trust me. You won’t regret it.”

Jake drove away after dropping her off. He had taken the leap of faith with Vicky. Only time would tell if tomorrow would be the beginning or the end of their story.


Reynolds’ wedding was a grand affair. He had opted for an exotic destination wedding near a serene lake. The place had a vibe of lasting romance from fairy tales. The drinks flowed freely, and the unrestrained laughter bloomed in the company of old friends. It suited perfectly for the reunion of old army friends.

“Sam! You made it!” roared a voice. She turned to see a group of her old buddies. While age may have affected their physique, their spirit was still young.

“I wouldn’t miss it for the world,” she grinned. The group welcomed her with warm hugs. This was her jam, the small group that trusted each other with life. Sam felt a sense of belonging she hadn’t experienced in a long time. She felt a lightness she hadn’t known since ... No, that’s not right. She suddenly realized she felt the same way about Jake.

The thought of Jake brought a smile to her lips. She imagined him at home, busy with his chores. Maybe even thinking about her. The image warmed her from the inside out. She wondered about his date with Vicky.

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