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Woodstock Cuckold Pt. 02

"Emily wins two tickets to Woodstock"

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Author's Notes

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Chapter 03: Two Tickets to Woodstock

Emily was at home dressed in her favorite short jeans and a cleavage t-shirt, her long hair flowing freely around her shoulders. She had spent the morning working on an article for the local newspaper about the growing anti-war movement. As she sat on the floor, taking a break from typing, she spun a Janis Joplin record on her turntable and sang along to "Piece of My Heart."

Suddenly, the DJ's voice on the radio interrupted the music, announcing that in five minutes, they would finally be giving away two tickets to Woodstock to the first caller who could answer their trivia question. Emily's heart leaped in her chest, and she quickly turned up the volume on her portable radio, shaped like a bright red Coca-Cola can. She had been dreaming of going to Woodstock ever since she heard about it, but the tickets were sold out for long. This could be her one chance to experience the greatest rock music festival ever. This was promising to be the defining moment of her generation.

Emily's listened to the radio announcer reveal the trivia question. "What was the name of the drummer for the Velvet Underground when they first started performing in New York City?" Emily's mind immediately went to her extensive record collection, filled with albums from all the great rock bands of the era. She had always been fascinated by the Velvet Underground and their avant-garde sound, and she had read everything she could get her hands on about the band.

She remembered reading somewhere that the drummer at that time was not the same as the one that appeared in their most famous albums. After a few seconds of intense concentration, she remembered the name. "Angus MacLise!" she yelled, grabbing the phone to dial the radio station.

Emily's hands shook as she picked up the phone and dialed the radio station's number. She held the receiver to her ear with one hand and crossed her fingers with her other hand, praying that she would get through in time. The phone rang once, twice, three times, and Emily's heart raced faster with each passing second.

Finally, after what felt like an eternity, someone picked up on the other end. "You're on the air with 104.3 The Buzz, what's your name and answer?" the DJ asked in a smooth, confident voice.

"Hi, I'm Emily," she said, trying to keep her voice steady. "My answer is Angus MacLise!"

There was a pause on the other end of the line, and Emily's heart skipped a beat. Had she gotten it wrong? But then, the DJ's voice came back on the air, louder and more excited than before. "Congratulations, Emily! You've just won two tickets to Woodstock!"

Emily let out a scream of joy and jumped up from her spot on the floor, sending scattered vinyl records flying in all directions. She couldn't believe it - she was going to Woodstock!

"Thank you so much!" Emily exclaimed, still in shock.

"No, thank you for playing, Emily," the DJ replied. "Enjoy the festival and be sure to tell us all about it when you get back. But remember, you need to come down to the radio station to pick them up. We're open until 6 PM today, so make sure to swing by before then."

Emily hung up the phone and immediately sprang to her feet, letting out a high-pitched scream of excitement. She couldn't believe it - she had actually won two tickets to Woodstock! She began jumping up and down on the shag carpet, her long hair bouncing around her shoulders as she chanted, "Oh my god, oh my god!"

After a few moments of pure ecstasy, Emily's mind started to race. She needed to decide who to take with her to the festival. A few of her girlfriends came to mind, but there was one person who stood out above the rest: Jesse. She had only been seeing him for a few weeks, but his behavior was so cute and he shared her love of music. Plus, the fact that he was a guitar teacher only added to his appeal.

Emily couldn't think of anyone she'd rather share this experience with, she could barely contain her excitement as she dialed Jesse's number. She paced around her living room, her heart racing as she listened to the phone ring on the other end. After what felt like an eternity, Jesse finally picked up.

"Hey, Jesse!" Emily practically shouted into the receiver. "I've got some incredible news!"

She could hear the sound of rustling sheets on the other end of the line as Jesse groggily responded, "What's going on? Is everything okay?"

"More than okay!" Emily exclaimed. "I just won two tickets to Woodstock!"

There was a pause on Jesse's end before he responded with a mix of disbelief and excitement. "Are you serious? That's amazing, Emily!"

Emily couldn't help but grin at his reaction. "I know, right? And I want you to come with me."

"Me!? Really?" Jesse asked, his voice now fully awake and enthusiastic. "Hell yes, I'm in! How did you even manage to get tickets?"

"The radio station had a trivia contest," Emily explained, launching into the story of how she had known the answer to the obscure rock and roll question. As she spoke, she could hear Jesse's grin growing wider and wider through the phone.

"Wow, you really are a rock and roll encyclopedia," he said admiringly once she had finished. "I'm so lucky to be going with you."

Emily beamed at the compliment. "I'm the lucky one," she said. "I can't wait to experience Woodstock with you, Jesse!"

Jesse's excitement was now mixed with worry. "But Emily, that's a long trip, and I don't have a lot of money right now. How are we going to afford this?"

Emily could hear the concern in Jesse's voice, but she was determined to make this work. "I know it's a long trip, but I've been saving up some money for a rainy day. Also, I have an idea," she said. "We can take my Ford Galaxie instead of buying expensive plane tickets. It might take longer to get there, but we'll save a lot of money."

Jesse rubbed his temples, still looking worried. "I don't know, Emily. It's a three-day festival, and we'll need to take time off work too. Are we really ready for this?"

Emily took a deep breath before responding. "Jesse, this is a once-in-a-lifetime opportunity. We can't let fear hold us back. We'll figure it out together. I promise." She could hear Jesse's breathing slow down as he considered her words.

Finally, he spoke up. "Okay, you're absolutely right. Let's do it! But we need to plan everything carefully to make sure we have enough money and time."

Emily let out a squeal of excitement. "Yes! Thank you, Jesse. I promise we'll make this an unforgettable trip." She already started to think about the road trip playlist, the camping under the stars, and all the amazing bands they were going to see.

Chapter 04: Pit-Stop at Emily's Ex-Boyfriend's House

Four days before the trip, Emily and Jesse were on the phone, finalizing their plans for their upcoming trip to Woodstock.

Emily and Jesse were both excited and nervous about their upcoming trip to Woodstock. They knew they had to plan everything out carefully to ensure a smooth journey. Four days before the trip, they were on the phone, discussing all the details.

"We need to make sure we have enough money for gas to get us there and back," Jesse said, sounding concerned.

Emily grabbed a pen and paper and started making calculations. "According to my map, it's about 3,000 miles from Los Angeles to Bethel, New York. My Ford Galaxie has a gas tank that holds 20 gallons, so we'll need to stop for gas multiple times along the way."

Jesse took a deep breath. "That's going to cost a pretty penny, but I guess it's worth it for Woodstock."

"Definitely," Emily agreed. "As for accommodation, I think we should plan on camping some days. It'll be cheaper than staying in hotels, and it's part of the festival experience."

"I've never been camping before," Jesse admitted.

"Don't worry, I have, it's not a big deal," Emily reassured him. Just then, Emily remembered something. "Oh, and I almost forgot. I guess I can get a tent for us to use for free from my ex-boyfriend. "

Jesse's face immediately fell at the mention of Emily's ex. He didn't want to be rude or jealous, but the thought of Emily getting anything from him made Jesse uncomfortable. He tried to hide his feelings and replied weirdly, "Oh, that's great, Em. Thank you."

Emily noticed the sudden change in Jesse's tone, and it made her feel a little bit hot. She couldn't help but smile to herself, feeling a sense of satisfaction that Jesse was showing some jealousy and insecurity. She knew it was wrong to feel that way, but it was a strange mix of emotions that she couldn't help but feel.

She tried to push the thoughts of her ex-boyfriend out of her mind. She knew it was wrong to feel that way, especially since she had no intention of getting back together with him, but she couldn't help the slight tingle of excitement that coursed through her at the sight of Jesse's jealousy.

After a couple of silent seconds, Emily finally spoke: "Great. I'm gonna schedule with him to pick up the tent tomorrow, what do you think?" trying to pretend she didn't notice anything different in his tone. "Sure Em, no problem. Just let me know. We can go there together." said Jesse, also trying to pretend everything was perfectly fine.

"Great, I'll let you know!" said Emily, finishing the call.

On the next day, Emily pulled up to the curb in front of a house with faded red paint and a well-manicured lawn. She put her Ford Galaxie into the park and turned to Jesse, who was looking a bit anxious. "We're here," she said, trying to sound as calm and confident as possible. "This is Alex's place".

Jesse took a deep breath and ran a hand through his hair, looking unconvinced. "I don't know, Em. What if he's still into you or something?"

Emily rolled her eyes. "Trust me, he's not. We broke up ages ago and we've both moved on. We're cool now. He's just doing me a favor, that's all. There's nothing to worry about." She gave Jesse's hand a reassuring squeeze before opening the car door and stepping out onto the sidewalk.

The sun was shining brightly overhead, casting dappled shadows through the leaves of the nearby trees. Emily walked up the concrete path leading to the front door, Jesse following closely behind. She could feel his tension radiating off of him.

"Come on, let's go", together, they walked up the concrete path to the front door, hand in hand. Emily could feel Jesse's hand trembling slightly, and she gave it another squeeze before knocking on the door.

As they waited, Emily couldn't help but think about Alex and how she would react to seeing him again. She had dated him for over a year before they decided to go their separate ways. He was a tall and muscular man, with broad shoulders and a chiseled jawline that made him look like he belonged on the cover of a men's fitness magazine. His thick, dark hair was always perfectly styled, and he had an easy confidence that could be both charming and intimidating.

Even she had been the one to suggest they borrow a tent from him, knowing that he had an expensive one that they had used for camping trips in the past. But now that she was actually standing outside his house, she couldn't help but feel a little nervous.

When Alex finally opened the door, Emily's heart skipped a beat. He was standing there shirtless, wearing only a pair of low-slung jeans that hugged his hips perfectly. His muscular chest and abs glistened with sweat, and Emily couldn't help but think "Oh god!" as she took in his impressive physique. She had known Alex was in good shape when they were dating, but she had forgotten just how good.

Next to her, Jesse shifted uncomfortably, his eyes narrowing as he took in the sight of Alex. "C'mon! You must be kidding me," he thought to himself, feeling suddenly self-conscious about his own body. He was fit, but he didn't have the kind of muscle definition that Alex did.

Alex took his time looking her up and down, his eyes lingering on her cleavage before finally meeting her gaze.

"Hi Emily," he said slowly, a smirk playing at the corners of his mouth. "I totally forgot you were coming over today."

"Hey, Alex," she managed to say, her voice barely above a whisper. She couldn't help but feel a rush of heat as memories of their past together flooded her mind, remembering the way his strong arms used to hold her tightly. She tried to keep her cool, reminding herself that she was with Jesse now, but her body seemed to have a mind of its own.

"By the way, you still look amazing," he said, a smirk playing on his lips.

Emily's heart skipped a beat as Alex's eyes lingered on her body, and she felt a flush creep up her neck. She stuttered out a response, trying to keep her voice steady. "I-I just came to pick up the camping gear... as we talked about on the phone," she managed to say, hoping he couldn't hear the nervousness in her voice.

Alex grinned, his white teeth contrasting against his tanned skin, and leaned against the doorframe in a way that made his muscles flex. "Of course, come on in," he said, his voice low and seductive. Emily felt a shiver run down her spine, acutely aware of the way his eyes lingered on her curves.

Emily hesitated for a moment before biting her lower lip, a nervous habit she hadn't done in years. She felt like a teenager again, with butterflies in her stomach and a blush spreading across her cheeks. Finally, she mustered up a shy smile and said, "Okay..." as she walked past Alex and into his house.

Alex's gaze lingered on Emily's body as she walked in front of him, taking in the way her jeans hugged her bubble ass. He smirked and followed her inside, completely ignoring Jesse who was still standing awkwardly by the door.

Jesse watched as Emily and Alex disappeared inside, feeling a pang of jealousy and emasculation wash over him. He hesitated for a moment before reluctantly following them inside, feeling like an unwelcome third wheel.

She could sense Alex watching her every move, and it made her heart race. She tried to focus on the task at hand, reminding herself that she was only there to pick up the camping gear.

Meanwhile, Jesse was unsure of what to do or say. He watched as Alex leaned against the kitchen counter, his muscles still on full display, and couldn't help but feel intimidated. He had never been the most confident guy, and being around someone like Alex only made him feel smaller.

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Emily finally turned to face Alex, trying to keep her cool. "So, where's the gear?" she asked, hoping to break the tension in the room.

As Emily asked Alex, he finally turned his attention to Jesse, who had been feeling more and more emasculated by the second. "Oh, sure. By the way, Jimmy right?" Alex said, purposefully mispronouncing Jesse's name. "The gear is probably in the attic. Somebody's gonna have to go up there and get it." He looked directly at Jesse as if challenging him to volunteer.

Jesse hesitated for a moment, looking to Emily for guidance. He felt like he was trapped in some sort of macho power play between Alex and himself. Emily gave him an understanding nod, and he reluctantly agreed to go up to the attic to retrieve the gear.

As Jesse climbed up the narrow stairs to the attic, he couldn't help but feel frustrated and emasculated. "So, where exactly is the gear?" Jesse asked, trying to keep his voice steady.

Alex shrugged, leaning against the doorway with a smirk on his face. "No idea, man. I haven't been up there in ages. But it's definitely in there somewhere. You'll just have to do some digging, pal."

Jesse resisted the urge to roll his eyes. This was just what he needed - a wild goose chase in a dusty attic. He took a deep breath and started to search through the piles of boxes and old furniture, hoping against hope that he would find the camping gear quickly.

As Jesse rummaged through the boxes in the attic, Alex turned his attention back to Emily, leaning against the doorway with a smirk on his face. "You remember that time we took that tent to the beach?" he asked, his voice low and suggestive.

Emily felt a flush of heat rise to her cheeks as she remembered that weekend all too well. It had been one of their first trips away together, and they had spent most of their time in the tent, only emerging for quick dips in the ocean to cool off. She bit her lip, trying to suppress the memory, but Alex's smirk only grew wider.

"I bet you and Jimmy-boy over there haven't had a chance to do something like that yet," he said, nodding towards the attic where Jesse was still searching for the gear.

Emily gave a nervous laugh, glancing up towards the ceiling as if Jesse might be able to hear them. "Shh," she hissed, half-heartedly slapping Alex's arm. "He'll hear you."

But Alex just leaned in closer, his muscular arm brushing against hers. "Relax, Em. But c'mon, you can't tell me you don't miss it. The way we used to be together... the things we did in that tent."

Emily's heart pounded in her chest as she felt Alex's warm breath on her neck. She knew she should push him away, remind him that she was with Jesse now, but there was something about his confident, alpha-male demeanor that made her feel weak in the knees. It was like she was transported back to high school when she had first fallen for Alex's charms, and all her senses were heightened.

She could feel the heat radiating off of Alex's body, see the way his muscles tensed and relaxed as he moved, and hear the low rumble of his voice as he spoke. And when he reached out to tuck a stray lock of hair behind her ear, she couldn't help but lean into his touch, just for a moment.

As Emily snapped out of her momentary trance, she glared at Alex and pointed a finger at him, her voice low so Jesse wouldn't hear. "Cut the crap, Alex. You know very well why we broke up. You cheated on me with that busty blondie."

Alex shrugged nonchalantly, leaning against the wall with a smirk on his face. "Come on, Em. It was just one night and I already said I'm sorry. Besides, have you seen Trisha lately? She's kinda fat right now. You always were more sexy than her anyway."

Despite herself, Emily felt a spark of satisfaction at Alex's words. "Really? Is she?" she asked, raising an eyebrow and smiling a little.

Alex chuckled and took a step closer to Emily, lowering his voice even further. "And let's not forget about your movements in bed. Your pussy was always so good to fuck. You know that, right?"

Emily's cheeks flushed at the memory, but she tried to keep her composure. "That's ancient history, Alex. I'm dating Jesse now and I'm happy with him."

"I know that, I'm just saying that you were awesome and still are. You probably are in my Top 3 of girls I hooked up with," said Alex like it was the best compliment ever.

Emily's eyes widened as Alex told her she was in his top 3 of best girls he ever dated. "Only top 3?" she asked, trying to hide the offense in her voice.

Alex smirked at her, his eyes gleaming with amusement. "Well, you know very well why you're not number one, Em," he said, his voice low and dominant.

Emily felt a familiar pang of submission wash over her as she looked up at Alex. She knew exactly what he was talking about. "What? You mean... Oh c'mon! We did anal a bunch of times, Alex!" she said, her voice barely above a whisper.

Alex's smirk grew wider. "Three or four times in a whole year, and I always had to beg for it," he said, taking a step closer to Emily. "You never offered to do it for me."

Emily could feel her heart racing as Alex's words washed over her. She had always been attracted to his dominant personality, the way he took control in the bedroom. But now, as she stood in his living room with her current boyfriend just feet away, she felt a mix of shame and desire.

"I-I didn't even know you wanted this that much!" she stammered, looking up at Alex with wide eyes.

He chuckled softly, reaching out to tuck a stray lock of hair behind her ear. "You knew, Em. You just didn't want to give me that kind of power over you."

Emily swallowed hard, feeling her body respond to Alex's touch despite her best efforts. She knew he was right - she had always been hesitant to fully submit to him, even though part of her craved it.

Alex smirked as he saw Emily getting more and more involved in the conversation. He knew he had her right where he wanted her. "Anyway, you also know that wasn't the only reason you're not number one," he said, his voice dripping with dominance.

Emily raised her eyebrows, her mind racing as she tried to think of what he could possibly mean. "The menage thing? Seriously?" she asked, almost incredulous.

Alex nodded, a sly grin spreading across his face. "You refused," he said, his tone matter-of-fact.

Emily's cheeks flushed with anger. "She's my sister, Alex! That's gross!" she exclaimed, her voice low but still heated.

Alex just shrugged, his muscles rippling with the movement. "You still refused," he repeated, his eyes locked onto Emily's.

Emily let out a frustrated sigh. "We did it with Lisa," she said, defensively. "And she was cute."

Alex nodded in agreement. "Yes, she was. But Lisa wasn't your sister," he said, emphasizing the last word.

"I-I just couldn't do that to Rachel," she stammered, her voice barely above a whisper.

Alex leaned in closer, his voice low and seductive. "But you would do it for me, wouldn't you, Emily?" he said, his question hanging heavy in the air.

Emily felt her heart race as she looked up at Alex, feeling completely under his control. She knew she should be angry, should be standing up for herself, but all she could do was nod silently, her body aching for his touch.

Emily was the kind of girl who had it all - brains, beauty, and fiery independence that made her irresistible. She was a proud feminist, always fighting for what she believed in and never backing down from a challenge. But even the strongest of women had their weaknesses, and for Emily, it was a man who knew how to take control.

Despite her empowered and independent nature, Emily couldn't help but feel a rush of heat between her legs when she was around a man who exuded dominance and power. The way they commanded a room, the confident smirk on their lips, and the muscular build that screamed strength and protection - it all made her wet with desire.

She loved the feeling of submitting to a man who knew what he wanted and wasn't afraid to take it. The way he would pin her down, his hands roaming over her body, his mouth claiming hers in a hungry kiss. It was a complete surrender of power, and it drove her wild with lust.

Meanwhile, Jesse was up in the attic, surrounded by boxes and cobwebs, feeling like a total loser. He could barely hear Emily and Alex talking downstairs, but for sure their voices were in a low and seductive tone, and he couldn't help but feel like he was missing out on something. He had always been the submissive type, the one who got pushed around and overlooked, and it seemed like that was never going to change.

As he searched through the dusty boxes, his mind wandered to thoughts of Emily and Alex together. He imagined them in some kind of dom/sub relationship, with Alex taking control and Emily submitting to his every desire.

Jesse let out a frustrated sigh as he continued to search for the camping gear. "Why did everything always have to be so hard for me? Why couldn't I just be confident and assertive like Alex?" He felt like he was always going to be stuck in this loser role.

As he finally found the gear and made his way back downstairs, he couldn't help but feel like he was walking into a lion's den. Emily and Alex were still talking, their voices hushed and intimate, and Jesse felt like an intruder. He knew he had to step up his game if he wanted to keep Emily interested, but he had no idea how to do it.

As Jesse's footsteps echoed down the stairs, Emily and Alex shared a knowing glance.

"Did you find everything okay, Jesse?" Emily asked, her voice sweet and innocent. Before Jesse could even open his mouth to respond, Alex cut in.

"Put the gear in the car and wait there, Jesse. We're not done talking yet." Alex's tone was firm and commanding, leaving no room for argument. "And make sure to close the door behind you."

Emily felt a shiver run down her spine at the way Alex had taken charge. She knew she should be standing up for Jesse, but something about the way Alex was acting made her feel weak in the knees.

Jesse looked between Emily and Alex, his eyes wide with shock. He stuttered out an "okay" before turning to leave, his shoulders slumped in defeat.

As the front door closed behind Jesse, Emily couldn't help but feel a twinge of guilt. She knew she should be more assertive, stand up for Jesse, and put Alex in his place. But something about the way Alex had taken control made her feel submissive and powerless. It was like he had a hold on her, and she couldn't resist.

Alex moved closer to her, his index finger pressing gently against her lips, blocking her from speaking. Then, her pulse quickened as he lightly touched her pussy over her jeans.

"After you come back from Woodstock, you're going to bring the camping gear back to me. Alone," Alex said, his voice low and commanding. "And when you do, I'm going to fuck you. No discussion."

Emily's cheeks flushed with shame and desire as he spoke, and she couldn't help but feel a twinge of excitement at the thought of being used by him. She nodded slightly, unable to speak with his finger still pressed against her lips.

"Now, I want you to walk to the door and shake your ass for me," Alex said, his hand still resting on her pussy. "Like the good little whore you are."

"But first..." Alex pulled her back towards him, pressing his lips against hers in a quick but intense kiss. Emily felt her body melt into his. She knew she should be angry with him for talking to her like this, for treating her like a sex object, but she couldn't deny the fact that it turned her on.

"Now, go," said Alex. Emily hesitated for a moment, feeling embarrassed and degraded, but the look in Alex's eyes told her that she had no choice. She took a deep breath and began to walk towards the door, swaying her hips exaggeratedly as she went. She could feel Alex's eyes on her, and the thought of him watching her like this made her feel even more turned on.

"Good girl," he said, his voice low and seductive. "I'll see you after Woodstock."

Emily finally left Alex's house, taking a deep breath before walking towards the car. She could see Jesse sitting in the passenger seat, looking at her with a mixture of confusion and disappointment. Emily knew she needed to act fast and think on her feet if she wanted to salvage this situation.

As she approached the car, she took a moment to compose herself, putting on her best seductive smile. She opened the driver's door and slid into the seat, turning to look at Jesse with a gleam in her eye.

"Thanks for being the man of the situation, Jesse," she said, her voice low and sultry. "I know Alex can be intimidating, but you didn't let him get to you. You just went up to the attic and got the camping gear. Like a boss!"

Jesse looked at her, his confusion deepening. "What are you talking about, Em?"

Emily leaned closer to him, her hand resting on his thigh. "Alex was just trying to provoke you, but you didn't even bother to respond. That's the kind of confidence I find sexy."

She could see the hesitation in Jesse's eyes, but she continued to press on, her fingers tracing small circles on his leg. "You know how much I love it when you take control, Jesse. It drives me wild."

Jesse swallowed hard, his body responding to Emily's touch despite his confusion. "Um...thanks?" he managed to say, his voice shaky.

Emily smiled, pleased with herself for turning the situation around. She leaned in closer, her lips brushing against Jesse's ear. "I can't wait to get to Woodstock and show you just how much I appreciate your confidence," she whispered, her breath hot against his skin.

Jesse shivered, feeling his body respond to Emily's words. He knew he should be upset about what happened with Alex, but he couldn't deny the way Emily's touch was making him feel.

Emily pulled back, her fingers still tracing circles on Jesse's thigh. "What do you think about going to my place right now? I don't know why, but I'm feeling horny today..."

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Written by AnaHanz
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