Woodstock Cuckold (Pt. 1) - Cover

Woodstock Cuckold (Pt. 1)

Copyright© 2024 by Ana Hanz

Chapter 2: The First Date

Erotica Sex Story: Chapter 2: The First Date - In 1969, Emily gets her hands on two tickets to Woodstock, and invites her new and innocent boyfriend, Jesse, to join her on a steamy road trip across the country. Jesse struggles with his submissive feelings when Emily is attracting attention from many other men. While Emily, on the other hand, is a free soul who is drawn to the excitement of the festival.

Caution: This Erotica Sex Story contains strong sexual content, including Cheating   Cuckold   Slut Wife   Wife Watching   DomSub   FemaleDom   Humiliation  

Sitting in his small and messy apartment decorated with lava lamps and Hendrix posters spread across all the walls, Jesse is a total nervous wreck, playing with the rotary phone cord like it’s some kind of life-or-death decision. He finally gets the courage necessary to dial Emily’s number.

“Hello?” Her voice is sugary sweet, and Jesse can practically hear her smirking on the other end of the phone.

“H-hey Emily, it’s Jesse,” he stutters, sounding like a total dweeb.

“Oh, hey Jesse! I wasn’t sure you’d actually call,” she teases, leaving Jesse to wonder if she doubts his interest or courage.

“W-well, I am calling,” he says, trying to keep his cool. “How are you?”

“I’m groovy, babe! What’s up with you?” Emily purrs, making Jesse blush.

“Yeah, yeah ... me too! Um, I’m wondering if maybe you’re free this weekend. Maybe we could, like, hang out or something ... maybe?” Jesse asks, his voice shaking like a leaf.

“Ooh, I’d love that! What’d you have in mind?” Emily can tell she’s in control, but she doesn’t mind one bit.

“I-I was thinking maybe a concert?” Jesse suggests weakly, knowing he isn’t great at making decisions.

“Eh, that’s cute, but I was thinking we could go to the drive-in and watch ‘Hello, Dolly!’” Emily says, her tone leaving no room for argument.

“Oh, sure! I didn’t know you liked musicals,” Jesse says, surprised but willing to go along with her plan.

Emily giggles. “Yeah, I love them! And there’s something so magical about watching a movie under the stars, with those far-out car speakers and a cooler full of soda pop.”

Jesse hesitates before admitting, “That sounds amazing, but actually, um ... I don’t have a car...”

“No biggie! We can take mine,” Emily says, taking charge without missing a beat. “My Ford Galaxie will do just fine.”

“Are you sure? I don’t wanna be a burden,” Jesse asks, feeling like a total wimp.

“Not at all! I’ll pick you up at 7, what do you think?” Emily says, her confidence unshakeable. “Wear your grooviest shirt!”

“Awesome, I can’t wait! Thanks, Emily” Jesse says, genuinely excited.

“Me neither, Jesse. See you then.” Emily says confidently, twirling a lock of her long, flowing hair around her finger. She hangs up the phone, leaving Jesse feeling both thrilled and anxious about their upcoming drive-in date, all while surrounded by the groovy tunes of his record player spinning the latest Beatles album.

Saturday at seven o’clock, Emily cruises down the street in her brand new 1968 Ford Galaxie convertible, looking like a groovy goddess in her white go-go boots, high-waisted blue jeans, and light brown suede jacket with a basic white top. Jesse awaits her outside of his apartment building, dressed in a black turtleneck, brown corduroy pants, and a denim jacket adorned with a couple of tiny peace signs. He appears a bit anxious but also excited about the idea of spending the night with a hot and interesting girl like Emily.

As Emily pulls up, she honks the horn, and Jesse hurries over to the car. Without hesitation, Emily leans over and greets him with a passionate kiss, catching Jesse off guard. “Hey there, Jesse. You ready for a far-out night?” Jesse, still in shock but pleasantly surprised, returns her smile. “Yeah, I am. Thanks for picking me up, Emily.”

Emily laughs, her long hair flowing in the breeze. “No problem, sweetheart. My parents gifted me this sweet ride, so I gotta flaunt it, you know? Haha.” Jesse is impressed. “Wow, this is one snazzy set of wheels. You’re lucky to have it.” Emily smiles and says, “Thanks, I know. Hop in, let’s boogie.”

Emily confidently steers her cherry red 1968 Ford Galaxie convertible while Jesse sneaks a glance at her outfit, checking her out. Emily catches him looking and playfully says, “Hey, are you gonna be staring at my boobs every date, drooling boy? Haha. I might need to invest in a bib for you or something!” She giggles out loud, her eyes sparkling with amusement.

Jesse blushes and stammers out an apology, looking embarrassed. After some seconds of silence while Jesse thought about how to answer properly, Emily, still grinning, asks, “So, do you dig it?” Jesse hesitates, looking uncomfortable, but eventually admits in a low tone, “Well, yeah, your boobs look fantastic.”

Emily throws her head back and laughs out loud, slapping the steering wheel. “Oh my god, Jesse! I meant the outfit, not my BOOBS!!” Jesse’s face turns a deeper shade of red, but he can’t help but chuckle along with her. “I’m sorry...” says Jesse, still red.

She smirks and says, “You know, every girl is used to men staring. But what really sucks is when they think they can say something gross about it too.”

Jesse quickly responds, “I would never do that, Emily. You deserve so much better than that.”

Emily flashes him a confident smile and says, “I know you wouldn’t. And that’s why I like you, Jesse. You’re different from other guys. You’re not just some gross dude trying to get in my pants.”

She fiddles with the retro radio, finding a classic 60s tune to jam out to. As they drive past a group of boys catcalling a girl on the sidewalk, Emily rolls her eyes and mutters, “See, that’s exactly what I’m talking about. It’s like, hello, we’re not objects for you to ogle at.”

Jesse nods in agreement, looking a bit uncomfortable. “Yeah, that’s not cool at all.”

Emily confidently steers the car down the road, her eyes fixed on the horizon. “I mean, let’s be real, I’ve dated my fair share of hot jocks and popular quarterbacks since high school. But after a while, it just gets old being treated like arm candy, you know? They might have the muscles and the status, but they don’t know how to treat a girl right. That’s the true!” She glances over at Jesse, who’s listening intently.

Emily smirks and continues, “But you, Jesse, you’re different. You’re not like those other guys, are you? I know we barely know each other yet, but I bet you actually listen to me and respect me. And let’s be real, it’s kinda refreshing to be with a guy who’s not afraid to show his softer side. It’s kinda hot, actually...”

She playfully nudges Jesse’s arm, making him blush one more time.

Jesse nods in agreement, a small smile playing on his lips. “Yeah, I guess I’m not the typical ‘alpha’ guy, but I don’t really care. I’d rather be myself and treat you right than act like some tough guy just to impress you.” He can’t believe his luck in being with such a hot girl, and he’s determined not to mess it up. So, despite feeling a bit emasculated by his beta nature, Jesse eagerly agrees with her.

Emily grins and replies, “And that’s exactly why I like you, Jesse. You’re real and genuine. And in a world full of posers and players, that’s worth more than any beefy muscles or letterman jacket.”

When they arrive at their destination, she quickly maneuvers her Ford Galaxie into an empty spot at the drive-in cinema, parking the car at the perfect angle to watch the movie. She turns to Jesse with a satisfied smile and says, “Damn, even being a little bit late for the session, we got lucky! This spot is awesome, don’t you think?”

Jesse nods in agreement, still in awe of Emily’s confidence and skill behind the wheel. “Yeah, it is great,” he moans in a more effortful way than he actually feels.

Emily’s smile widens as she turns to face him. “So, what do you say we go grab some snacks? I’m craving some popcorn, coke, and maybe some candies.”

Jesse quickly jumps at the opportunity to prove his worth, based on everything he heard on the way to the cinema. “Oh, wait! Let me pay for it,” he says, interrupting her mid-sentence. “It’s the least I can do for you after everything you’ve done for me.”

Emily raises an eyebrow at him, amused by his sudden eagerness to assert his masculinity. “Well Jesse, aren’t you such a gentleman,” she teases, her eyes sparkling with mischief.

Jesse blushes at her words, feeling both embarrassed and proud at the same time. “I just want to make sure you have a good time tonight,” he mumbles, stopping looking into her eyes and now looking down at his own hands.

Emily’s smile softens as she reaches out to touch his arm. “I’m already having a great time, Jesse. But thank you for offering to pay. It’s really sweet of you, okay?” She pauses for a moment before adding, “Why don’t you stay here and get us settled in while I go grab the snacks? That way you can still feel like you’re taking care of me.”

“Yeah, okay. That sounds good,” he says, opening a small smile, and nodding while looking at her eyes

She pauses briefly and puts her hand on his arm before getting out of the car. “I’ll be back in a couple of minutes.” Then, she opens the door of the Galaxie and heads toward a concession stand with a $10 bill given by Jesse.

As the movie begins, Jesse settles into the car, reclining the seat and tuning the radio to the correct station for the film’s audio. He takes off his shoes, wiggling his toes in the plush carpet of Emily’s Galaxie. He lets out a content sigh, watching the opening credits roll on the giant screen in front of him.

After a few minutes, Jesse starts to realize that Emily has been gone for longer than he expected. He checks the clock on the dashboard and sees that it’s been almost ten minutes since she left to get snacks. He starts to feel a twinge of anxiety, wondering what’s taking her so long.

Five minutes more pass and he decides to take a look around. He twists his neck in the direction of the concession stand and finally sees her, but she’s still not carrying the popcorn or the rest of the snacks. Instead, she is talking to a guy ironically wearing a letterman jacket, completely engrossed in their conversation.

The guy who’s with Emily is tall with broad shoulders, his clothes emphasizing his muscular build. His hair is perfectly combed back, and his smile is charming and confident. He exudes an aura of popularity, especially when it comes to girls.

Jesse can’t help but be jealous when he sees the guy next to Emily, laughing at whatever she just said. He wonders if he should march over there and mark his territory, but he decides he doesn’t want to come off as some possessive boyfriend on their first date. Plus, he remembers what Emily said about wanting a guy who respects her and treats her as an equal. However, it doesn’t stop him from watching the entire event from afar.

As Jesse watches Emily and the jock, he can’t help but feel like a complete loser. There he is, sitting alone in his car while his date is off flirting with some muscular meathead. “What does she even see in a guy like me?” Jesse thinks to himself, feeling smaller and smaller by the second.

In this while, Emily tosses her hair back and laughs at something the jock says, her fingers brushing against his arm. “She doesn’t seem to care at all about the fact that she’s leaving me all alone, and why would she? I’m just some scrawny, boring guy who couldn’t possibly compare to the powerful jock standing in front of her.” Jesse overthinks as usual.

Jesse feels a pang of jealousy as he watches the jock’s fingers slightly touching Emily’s, clearly happening something between them. “He probably slept with half the cheerleading squad,” Jesse thinks bitterly, feeling like he doesn’t stand a chance against someone like that. He sinks further into his seat, feeling like a complete loser.

Jesse’s heart races as Emily and the jock are talking and laughing together. He can’t believe how physically close they seem to be getting. He’s so focused on them that he doesn’t even realize he’s holding his breath.

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