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sleekervae · 5 months ago

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"yes" | sid sadowskyj x fem!reader

Masterlist

Pairing: sid sadowskyj x fem!reader

Summary: Sid’s carefully planned world gets turned upside down when Maggie, his bold and unpredictable college friend, dares him to spend a day saying “yes” to everything she suggests.

Warnings: dares, impulsivity, reading aloud, erotic writing, public dancing, heights, fluff, some movie spoilers kinda??

Word Count: 8,040

The lecture hall buzzed with low murmurs and the scratch of pens on paper. Sid Sadowskyj sat near the back, head bowed over his notebook as he furiously jotted down everything the professor said. His life plan didn’t allow room for distractions, and yet, out of the corner of his eye, Maggie Andrews was exactly that.

Maggie, perched two rows ahead, was not a silent observer like the rest of the students. She leaned back in her chair, lazily twirling a pen between her fingers, occasionally interjecting with a witty comment or sharp question that made the professor stumble. It wasn’t her confidence that first caught Sid’s attention—it was the way she seemed to take up space without even trying, like she owned the room.

Sid had met Maggie on his first day of college. They were both late to orientation, rushing into the main hall at the same time and nearly colliding in the doorway. She had laughed it off, brushing her wild curls out of her face as she stuck out her hand and introduced herself. “Guess we’re both off to a strong start, huh?” she’d said, flashing him a grin. Sid, feeling awkward but polite, shook her hand and muttered his name. From then on, Maggie had seemed to pop up everywhere—grabbing coffee in the student lounge, cutting through the quad to make it to class, even occasionally showing up at the library where Sid liked to study.

They weren’t close, but Maggie had a way of weaving herself into his life. They’d spent late nights together in group study sessions, complaining about assignments and professors. She’d once shared half her sandwich with him when he forgot his lunch, casually declaring, “You’d probably starve otherwise, future CEO.” He’d helped her fix her laptop before a big paper was due, earning an uncharacteristically heartfelt “Thanks, Sid, you’re a lifesaver” in return.

Maggie was the kind of person Sid could tolerate for short bursts—witty, sharp-tongued, and full of energy that sometimes exhausted him just watching her. But there was a connection, an unspoken understanding that she saw through his carefully constructed walls. She wasn’t trying to tear them down, necessarily, but she had a way of knocking on them every now and then, just to see if he’d answer.

Now, weeks into the semester, Maggie had cemented herself as a fixture in his routine, whether he liked it or not. In class, she always managed to pull him into conversations, teasing him about his meticulous notes or his “boring” outlook on life.

Sid sat at his usual spot in the back row, head bent over his notebook as he diligently took notes. The topic of the day: “Seizing Opportunity and Building a Life of Significance.”

It wasn’t the first time the class had waded into existential territory, but today hit differently. The professor’s words about taking chances and embracing the unknown felt like a spotlight on Sid. When he announced their next assignment—a personal essay reflecting on a pivotal moment where they took a risk or stepped outside their comfort zone—Sid’s pen paused mid-sentence.

He tried not to panic. The whole class was groaning in unison, some muttering about how cheesy it sounded. Maggie Andrews, seated two rows ahead, was the only one who looked intrigued. She sat upright, her chin resting on her hand, her pen tapping thoughtfully against her notebook. Sid couldn’t help but watch her, even as unease churned in his stomach.

What was he supposed to write about? He didn’t take risks. He planned, calculated, and avoided reckless decisions at all costs. His life had always been about control, about working toward a future he could depend on. Was he supposed to fake some grand story for the sake of an essay?

As the class wrapped up and students began packing their bags, Sid remained lost in thought, his notebook open to the half-written header of the assignment: “A Time I Took a Leap.”

“Oi, future CEO!” Maggie’s voice cut through his spiraling thoughts. He looked up just in time to see her bounding over to him, her bag slung over her shoulder and her ever-present grin plastered across her face.

Sid sighed, tucking his notebook into his bag. “Hi, Maggie.”

“Walk with me,” she said simply, gesturing toward the door.

He hesitated, but she didn’t wait for his response. With a resigned shake of his head, he followed her into the crowded hallway.

“Big thinker today, eh?” Maggie teased as they navigated the throng of students. “I could practically hear your brain melting during class.”

Sid shot her a sidelong glance. “It’s just an assignment.”

“An assignment you’re stressing over already,” Maggie countered, bumping her shoulder against his. “Let me guess—you have no idea what to write.”

Sid frowned, unsure how she always seemed to read him so well. “Not everyone has some big, dramatic life experience to write about.”

“That’s your problem,” Maggie said, stopping abruptly and turning to face him. The hallway buzzed around them, but she didn’t seem to notice. “You’re too busy trying to avoid all the messy, unpredictable stuff that makes life worth writing about.”

He crossed his arms, feeling defensive. “Not everyone wants to run headfirst into chaos like you.”

“Maybe not, but that’s where the good stories are,” she said with a shrug. Her eyes sparkled with mischief as she tilted her head. “Which is why I have an idea.”

Sid raised an eyebrow. “I’m afraid to ask.”

“It’s not that scary,” she said, grinning. “Let’s make a deal. For one day, you say yes to everything I suggest. No backing out, no overthinking—just pure, unfiltered ‘yes.’”

“That sounds ridiculous,” Sid replied flatly.

“No, it sounds like a great way to spend a boring old Thursday,” Maggie shot back, leaning in with that infuriatingly confident smirk. “Come on, Sid. You want something to write about, don’t you? Here’s your chance. One day. You and me. Let’s see where it takes you.”

He stared at her, the weight of her challenge pressing against the knot of discomfort in his chest. The logical part of him screamed to walk away, to retreat to his carefully constructed bubble of safety. But then he thought about the blank page waiting for him, about the essay he’d have to write, about the gnawing feeling that maybe—just maybe—Maggie was right.

Sid hesitated, her playful confidence both exciting and terrifying him. “What if I say no?” he asked, his tone wary.

She shrugged, stepping back and spreading her hands in mock defeat. “Then I guess you’ll write about how boring you are.”

Her words stung, but they also stirred something in him. A flicker of indignation. A spark of curiosity.

"Here, I'll even the field:" she decided, her smile mischievous as she studied Sid's expression, "If you succeed in your challenge, you can dare me to something. Something I can't refuse."

Her words hung in the air, tempting him, and Sid felt a sudden rush of heat. He wasn’t sure where this was headed, but the challenge in her eyes stirred something deep inside him, a need to prove that he could let go and embrace the unknown.

“Fine,” he said finally, his voice firmer than he expected. “One day.”

Maggie’s grin widened, and she clapped her hands together. “Jubilee Cafe at 9 tomorrow. Don't be late!”

And just like that, she was gone, weaving through the crowd with the same effortless energy that seemed to drive her every move. Sid stood there for a moment, letting the weight of what he’d just agreed to settle in.

One day. How bad could it be?

The next day, Sid arrived at Jubilee Café, his usual haunt when he needed a quiet spot to think. It wasn’t overly crowded, the perfect place for him to mentally prepare for the day ahead—or at least, that’s what he told himself as he fidgeted with his cup of coffee, waiting for Maggie. She was late, but that was to be expected. Sid didn’t mind; he could use the time to calm his nerves, or at least try to.

The door jingled as Maggie stepped in, her presence like a whirlwind. She immediately spotted him and waved, her bright smile making it impossible for him to be annoyed by her tardiness. She slid into the seat across from him, unbothered by the fact that she was clearly running behind schedule.

"Hope you didn’t get too comfortable," she teased, kicking her feet up on the chair. "You ready for your challenge, Sadowskyj?"

Sid sighed, stirring his coffee absentmindedly. "Yeah, yeah. I guess so."

Maggie studied him for a moment, her eyes glinting with amusement and a hint of something more. "Alright, so let’s talk shop, first. What do you want?"

Sid blinked at her, confused. "What do you mean, what do I want? I want... I want to be stable. I want to be able to support myself, make sure I have enough for rent, health insurance, you know, the basics."

Maggie raised an eyebrow, clearly unimpressed. "Is that all?"

Sid furrowed his brows, feeling defensive. "I don’t see the point in wanting a lot of things. Why would I dream of something unattainable? Job security, health insurance... That’s what keeps people alive. What else is there?"

She leaned in slightly, her voice softer but still probing. "But what about when you're old? When you look back on everything you’ve done—what do you want to remember? Do you want to look back and see a long list of ‘safe’ decisions? Or do you want stories? Moments where you just lived?"

Sid hesitated, a discomfort settling in his chest. "I—" He didn’t know how to explain it. The idea of looking back and not seeing anything concrete, not having something solid and dependable to show for his efforts, made him feel uneasy. He was the kind of person who liked structure, who liked knowing exactly what was coming next. "I want security, Maggie. I don’t know what else there is."

Maggie’s eyes softened, and she gently placed her hand on top of his. "I get that. But don’t you ever want more than just the basics? Don’t you ever wonder what it’d be like to really experience life? To take a chance and see where it leads? Because I think you’d be surprised at how much more you could get from saying 'yes' to the unexpected."

Sid swallowed, a strange flutter in his chest. He hadn’t realized how badly he’d needed someone to ask him that. For so long, his life had been about maintaining control, about sticking to a script. But Maggie’s question—her genuine curiosity—pulled him into a space he wasn’t sure he was ready for, but also felt strangely drawn to.

"I don’t know," he admitted quietly. "I guess I’ve never really thought about it that way."

Maggie smiled, a soft, knowing expression that made Sid feel like he was the one being seen for the first time. "That’s okay. You’re not alone. But today’s the day to start. No more overthinking, Sid. Let’s make some memories. What do you say?"

Sid looked down at his coffee cup, the swirling liquid inside reflecting the uncertainty—and excitement—he felt. Could he really do this? Could he really throw caution to the wind and say ‘yes’ to whatever Maggie had in mind?

Finally, he lifted his gaze to meet hers. "Alright," he said, his voice quieter but firmer than before. "Let’s do it."

Her smile was victorious, a sharp edge of triumph that made his heart skip a beat. “Great! Let's go.” she started out of the booth.

"Where are we going?" Sid asked.

"To get a drink," she replied simply, offering her hand to him, "A surprise drink challenge. You’re going to say ‘yes’ to everything I order for you—and then you'll order something ridiculous for me in return.”

Sid glanced at his half-empty cup of coffee. “I’ve already had coffee today, Maggie.”

“That’s your problem,” she teased, leaning forward, her eyes locking onto his with that unstoppable determination, "Do you trust me?"

Sid hesitated, his fingers tapping against the surface of the table. He had to admit that he liked the idea of something unexpected, but the rational part of his brain was still screaming at him to be cautious. But then again, this was the whole point of the challenge.

"Alright. Let's go,"

Sid stood next to Maggie in the line at the counter, his mind still lingering on the bizarre drink he'd just ordered for her. He felt a bit out of his element, still unsure how he’d ended up agreeing to this, but there was no turning back now.

Maggie, ever the picture of confidence, was chatting with the barista like they were old friends, her hands animated as she explained something about her latest photography project. Sid tried to focus on the conversation, but his gaze kept drifting back to her, and he couldn't help but notice the way her yellow jacket hugged her curves. The fabric clung to her waist, and her long, dark hair cascaded down her back, catching the light in a way that made her look like she belonged in a movie.

He shifted his weight from one foot to the other, trying to look casual, but it was hard to ignore how she looked standing there, so effortlessly cool. It was always like this with Maggie—her energy magnetic, her presence undeniable. Sid had been aware of her attractiveness since they'd met, of course, but it was becoming harder to ignore the way his body responded to her now. The way her voice carried, the sparkle in her eyes, even the way she laughed at some inside joke with the barista—it all seemed to make his chest tighten in a way he wasn’t used to.

Maggie noticed his gaze and flashed him a mischievous smile, a knowing look passing over her face. "What?" she teased, her tone playful. "You going to get lost in my eyes now, Sid?"

Sid cleared his throat, instantly feeling his face flush. "No," he said quickly, trying to play it cool, but the words came out a little too fast. "Just… wondering how you always manage to make even waiting in line look like a performance."

Maggie raised an eyebrow, clearly enjoying his discomfort. "Is that so? I think you just like the view." She leaned in slightly, her voice dropping to a mock-serious tone. "Don't worry, Sid. I’m not as distracting as I seem."

Sid opened his mouth to respond but was cut off by the sound of their drinks being ready. He quickly grabbed his own drink, mentally reminding himself to focus on the task at hand.

They made their way back to their booth, the sound of the café’s chatter almost drowned out by the pounding of Sid’s heart. He couldn’t stop his mind from wandering, trying to shake off the slightly uncomfortable feeling of being so... aware of Maggie. He could still feel the weight of her teasing gaze from earlier, like a flicker of something that he couldn’t quite place.

Maggie slid into the booth first, her eyes bright as she settled her drink in front of her. Sid hesitated for a moment before following her, sitting across from her and unwrapping the cup of his own drink. The aroma of coffee, strong but smooth, hit him first, familiar and comforting. But he couldn’t deny the slight tension in the air as Maggie waited expectantly.

“Alright,” she said, her smile practically daring him, “let’s see what you got, Sid.” She took a sip of her own drink and immediately raised an eyebrow. “I guess... it’s not terrible. A little too sweet for my taste, but not bad. What about you?”

Sid’s eyes flickered from her drink to his own. He took a cautious sip, expecting the usual taste of coffee. But what he was greeted with instead was something that tasted… off. A heavy, overbearing sweetness settled on his tongue, and he quickly swallowed, grimacing.

“What the hell is this?” Sid coughed slightly, placing the cup back on the table. “It tastes like someone dumped half a bottle of syrup in here. I thought you were going to make it fun, not kill me with sugar.”

Maggie giggled, clearly delighted by his reaction. “I told you, no turning back. You agreed to the blind drink challenge, didn’t you?”

Sid threw her an exasperated look, but he couldn’t help the small smile tugging at the corners of his lips. “You’re cruel, you know that?”

“I prefer the term adventurous,” Maggie teased, swirling her own drink and taking another sip. She leaned back in her seat, crossing her arms, eyes gleaming with amusement. “You’re not the first person to complain about the "butter beer" drink. A bit too sweet for my preference, I'll be honest.”

Sid rolled his eyes. “You’re really enjoying this, aren’t you?”

“You have no idea,” she said, her smile widening as she took another sip. “But hey, at least I didn’t make you try a weird combination like coffee and pickles. That’s a level of daring that takes real courage.”

Sid shuddered at the thought. “I don’t think I could survive that.”

Maggie’s eyes sparkled as she leaned in closer, dropping her voice to a playful whisper. “I wouldn’t be so sure. You’re not backing out, are you?”

Sid stared at her, his mind racing as he remembered the bet. There was something about the way Maggie said it, so carefree but so sure of herself. She wasn’t just challenging him in the way she always did—there was an edge to it, a challenge that made his pulse race. A challenge he couldn’t seem to resist. He sighed, running a hand through his hair, and gave her a reluctant smile.

“Fine, fine. I’ll do it. But you’re buying the next round.”

Maggie’s grin widened, and she clinked her cup against his. “Deal.”

The library was quiet, save for the faint rustle of pages being turned and the occasional murmur of hushed voices. Sid had never been a huge fan of the place—he preferred a good dive bar or coffee shop for hanging out, somewhere with a little more energy—but Maggie had insisted. And, as usual, he found himself following her without question.

They wandered through the aisles, the rows of books seeming endless. Sid couldn’t help but feel a little awkward, especially when Maggie seemed so at ease among the quiet atmosphere. She wasn’t the type to be easily intimidated by anything, and he quickly learned that she had no issue with making her own fun in places like this.

After a while, Maggie led him to a corner of the library where the books were older, leather-bound, and a little more... intriguing. Sid noticed a few covers that looked like they belonged in a forgotten 80s movie collection, but there was one that caught his attention. It was an old romance novel with a faded title, but it was the cover art that made Sid raise an eyebrow—a somewhat steamy image of a woman in a rather suggestive pose.

"You're not serious," Sid muttered, trying to hide his surprise as Maggie handed him the book with a wicked grin on her face.

“Come on, Sid. This is your next challenge,” she said, her tone laced with mischief. "Flip to a random page and read it out loud. No backing out."

Sid eyed the book warily. "Wait, what exactly is this? Some kind of... trashy romance novel?"

Maggie just smirked. "You could say that..."

Sid's heart raced a little, unsure what he was getting himself into. The library was practically deserted, save for a couple of older people browsing in the back, but Sid still couldn’t shake the feeling that someone might overhear him. He glanced nervously around, then back at Maggie. Her grin was as devilish as ever, and he couldn’t help but feel both nervous and intrigued.

"Alright, here goes nothing," Sid muttered, trying to keep his cool. He opened the book to page 80, and almost immediately, his eyes widened at what he found. The writing wasn’t exactly subtle, and it was pretty clear that this was no ordinary romance novel. The paragraph began with a slow build-up, but quickly became more explicit in nature.

Sid swallowed hard, trying to calm his nerves. He knew that this was exactly what Maggie wanted—to throw him into a situation where he’d have no choice but to go along with whatever she dared him to do.

“Just read it. Don’t be shy,” Maggie whispered, leaning in slightly, her voice teasing.

With a deep breath, Sid began reading aloud, his voice hesitant at first but growing steadier as he continued.

"His hands roamed over her body, exploring every curve as if memorizing the way she felt beneath his touch. Her breath quickened, matching his as he pressed his lips to her neck, the heat between them palpable. She moaned softly, arching into him as their bodies came together, desperate and eager. Each movement was slow, deliberate, savoring the moment before they succumbed to the need building between them."

Sid paused, his face flushing a deep shade of red. He couldn’t believe he was reading something like this in a public place, and yet, there was a certain thrill in it too, like he was caught in a moment of rebellion.

Maggie, however, was enjoying every second. She sat back, her eyes glinting with mischief as she watched him try to get through the scene, her lips curling into an amused smile.

"Come on, keep going," she urged, leaning in just a little closer.

Sid exhaled sharply, his throat suddenly dry. He couldn’t back out now—not when Maggie was looking at him like that. He read on, voice shaking slightly but with more confidence now.

"She gasped as he pressed closer, the tension between them breaking as they finally gave in to the desire that had been building all night. The world around them faded away, leaving only the heat of their bodies, the desperate need to feel each other completely. There was no turning back now."

Sid quickly finished the passage, slamming the book closed and practically throwing it back into Maggie’s hands. His face was bright red, and he could feel his heart racing.

"Okay, that’s enough," he muttered, trying to hide his embarrassment behind a forced grin. "I can't believe I just did that."

Maggie looked entirely unbothered, still grinning like she’d just won some grand prize. "Oh, come on now," she teased. "A little romance doesn’t hurt anyone, Sid."

Sid took a deep breath, his mind reeling. "I hate you. You know that?"

Maggie winked at him, clearly enjoying every second of his discomfort. "You’re not the first to say that," she replied, her voice still full of that mischievous energy. "But hey, you survived. Now, let's see if you're brave enough for the next one."

Sid shook his head, trying to get the image of what he'd just read out of his mind. He was glad no one else was around to hear the passage. But still, he couldn't deny that something about the dare—about Maggie's challenge—had made his pulse spike. He wasn't sure if it was the thrill of being put on the spot, or the strange energy that always seemed to buzz when he was with her, but he couldn't shake the feeling that this was only the beginning of something far more intense.

The day had taken a turn Sid hadn’t quite anticipated. They’d made their way down to the local square after leaving the library, the afternoon sun casting a warm golden glow over the streets. Sid had almost forgotten about the next dare in the excitement of surviving the library challenge, but as they strolled, Maggie’s eyes lit up when they passed a street corner where a busker was playing a lively tune on his guitar.

Sid was just about to walk past when Maggie stopped, her fingers tapping against her chin in that familiar way.

“Oh no,” Sid muttered under his breath, already knowing what was coming.

Maggie shot him a sly smile. “You know what this is, don’t you?”

Sid groaned. “Don’t even think about it. There’s no way I’m dancing in front of all these people.”

The busker’s upbeat melody seemed to be calling to Maggie, and her gaze locked on the open space in front of them. “Come on, Sid. You have to say yes to this one. I dare you to dance.”

Sid couldn’t believe what he was hearing. He glanced around, noticing a couple of people watching the performer, and it made him feel like his palms were starting to sweat. Dancing wasn’t his thing—not in front of anyone, anyway. But there was something about Maggie’s challenge that had him feeling like he couldn’t back down.

“You’ve gotta be kidding,” he said, running a hand through his hair. “This is—this is just... ridiculous.”

Maggie’s eyes twinkled with amusement. “What’s the matter, Sid? Afraid to show off those moves? You said yes to everything so far, and this is your next one. It’s not that bad.”

"Yeah, but --"

"Unless you want to go read some more saucy novels?"

Sid knew that look too well. She was going to keep pushing until he gave in, and he wasn’t sure how much longer he could keep his stubbornness in check. He exhaled sharply, glancing back at the busker, then back to Maggie.

“Alright, alright,” he muttered, throwing his hands up in mock defeat. “I’ll do it. But don’t expect me to be good at it.”

Maggie grinned and stepped back, allowing Sid to step into the space in front of the busker. The man played on, oblivious to the scene he was about to inspire, his fingers strumming the strings with ease. Sid shifted uneasily on his feet, his body tense as he tried to find a rhythm.

He swayed awkwardly at first, a little unsure, but as the music flowed, something in him loosened. He felt ridiculous, but as the beat caught him, he couldn’t deny that there was something kind of freeing about it, something thrilling in just letting go.

Maggie watched, her arms crossed, clearly amused at his hesitation, but also impressed that he was going through with it. But then, Sid took a deep breath and—maybe to his own surprise—he started moving with the music more confidently. His feet followed the beat, his shoulders loosened up, and for a brief moment, he wasn’t the nervous guy who hated being the center of attention.

As the song picked up, Sid couldn’t help but laugh at himself, his earlier embarrassment starting to fade. He threw a glance toward Maggie, who stood just off to the side, still watching with a grin on her face. She raised an eyebrow at him, clearly entertained by his progress.

“You know what?” he said, catching his breath, a mischievous spark in his eyes. “You’re right. This isn’t so bad."

"See?" Maggie beamed, "You're so good at it!"

Sid scoffed back, "Maybe I am. But you know what would make it even better?"

"What?"

"You joining me.”

Maggie’s smile faltered for only a moment. She looked at him with wide eyes, as if she hadn’t expected him to turn the tables on her. “Me? You want me to dance with you?” she asked, her voice tinged with mock surprise.

“Yeah. Come on, Maggie. I’ve been dancing alone like a fool. If I have to suffer, you do too.”

Maggie couldn’t help but laugh. She rolled her eyes dramatically, then stepped forward with a shrug. “Fine. Shove over.”

Sid grinned, watching as she shifted into the open space in front of him. She looked far more confident than he had ever been, her movements sharp and full of energy. As the beat picked up again, Maggie started to move, her feet tapping against the pavement in sync with the rhythm.

Sid took a step back, watching her intently, feeling that rush of adrenaline. He couldn’t help but admire the way she seemed to own the space, the way her confidence was infectious. The crowd that had gathered around the busker started to take notice, some even applauding as they picked up on the little impromptu dance performance.

Maggie, seeing Sid in the background trying to keep up with her, turned around, extending a hand toward him. “Come on, Sid. You said you’d do it.”

Sid smirked, unable to resist. He took her hand and pulled her closer, the two of them now dancing together in the middle of the crowd. The music carried them both, and despite the nervousness still lingering in the pit of his stomach, Sid couldn’t help but feel alive in a way he hadn’t expected.

For a moment, there was no one else but them, moving together to the beat in perfect sync. The crowd cheered louder as they spun and laughed, and Sid realized that this was the kind of fun he didn’t get to have often. He was so used to being cautious, always overthinking everything—but here, with Maggie, he felt something new. Something wild.

They finished the song in a flurry of laughter, Sid pulling Maggie into a spin before they both stumbled back, breathless. He had to admit it—this dare, ridiculous as it had been, turned out to be one of the best moments he’d had in a long time.

“That wasn’t so bad, huh?” Maggie teased, her chest rising and falling with her rapid breathing.

Sid grinned, wiping his brow. “Yeah, yeah. Maybe I’ll even do it again... if you’re lucky.”

Maggie smiled back at him, clearly pleased by his response. “Well, come on, Sid,” she said, her voice low and playful. “You’ve got two more dares left for the day.”

Later that day, after they’d shaken off the adrenaline from their impromptu dance performance, Sid and Maggie wandered through the city, enjoying the cool evening breeze and the sense of mischief that lingered in the air. Sid felt strangely empowered by his earlier performance, his confidence bolstered by Maggie’s carefree spirit.

They passed the quiet streets, their footsteps echoing in the stillness, until Maggie suddenly stopped in her tracks, her eyes glinting with a fresh idea. Sid raised an eyebrow, sensing another dare on the horizon.

“Alright,” she said, her lips curling into a grin. “I’ve got another one.”

Sid groaned dramatically. “Not another one. Come on, give me a break.”

But Maggie wasn’t listening. She grabbed his arm and tugged him toward a narrow alleyway between two buildings, where an old fire escape ladder stretched upward, disappearing out of sight.

Sid stared up at it. His stomach dropped a little. “No. Absolutely not.”

“Yes,” Maggie replied, unbothered by his protests. “Climb it. All the way to the top.”

Sid’s heart skipped a beat. The fire escape was a good 30 feet off the ground, rusted and old, with the steps barely wide enough for his feet. He wasn’t exactly a fan of heights, and the idea of climbing up to an exposed rooftop made him feel uneasy in the pit of his stomach.

“Are you serious?” he asked, looking over at her like she had lost her mind.

Maggie just smirked, clearly enjoying his discomfort. “You’re supposed to say yes to everything, remember? Besides, it’s not like you have to jump off the roof afterward or anything. Just climb up.”

Sid hesitated, looking back at the ladder and then at Maggie’s face, which was full of expectation. He knew she wouldn’t let him get away with backing down, and honestly, he wasn’t sure if he could stand the humiliation of saying no.

“Alright, alright,” Sid muttered, taking a deep breath. “But if I die, it’s on you.”

Maggie laughed, all too pleased by his reluctant compliance. “You’ll be fine. Look -- I’ll even go first. It's not that bad.”

Before Sid could protest, she grabbed the rungs of the ladder and began climbing, her movements fluid and confident. Sid watched, a knot forming in his stomach, as she quickly made her way up, disappearing over the ledge and out of sight.

He felt like a fool standing there, staring up at the fire escape, but he couldn’t bring himself to back out. After a long moment of hesitation, Sid reached up and grabbed the first rung, the cool metal sending a shiver through his body. His hands were clammy, but he forced himself to focus. One step at a time.

The first few rungs felt steady, but as he climbed higher, his grip tightened, and his head began to swim. He tried not to look down, but the urge to check his progress was overwhelming. When he did glance down, the ground felt impossibly far below, and the city stretched out in all directions. Sid’s pulse quickened, but he kept climbing, trying to ignore the way his heart thudded in his chest.

Finally, after what felt like an eternity, Sid pulled himself over the edge and onto the roof, his knees weak and his breath coming in ragged gasps. He looked up to find Maggie standing there, hands on her hips, watching him with an amused smile.

“See? Was that so bad?” she teased, clearly pleased with the result.

Sid took a moment to steady himself, wiping his hands on his jeans as his heartbeat slowly returned to normal. “You’re nuts,” he muttered, looking out at the city skyline. The view was stunning, though the reality of how high up they were still had his stomach fluttering.

“Maybe,” Maggie replied, crossing the roof to stand next to him. “But I knew you’d make it. You’re braver than you think.”

Sid glanced at her, a little surprised. “Brave? I just don’t like losing bets.”

Maggie laughed softly, her eyes warm as she regarded him. “Fair enough. But I’m still impressed. I know how you feel about heights.”

Sid smiled back, though he felt a strange sense of intrigue overcome him, “How did you know I didn't like heights?”

Maggie raised an eyebrow, leaning her elbows on the ledge of the roof as the wind tousled her hair. “Oh, please, Sid. You practically turned green when we passed the Ferris wheel at the fall fair last month. You couldn’t get out of there fast enough.”

Sid blinked, caught off guard. “You noticed that?”

“Of course I noticed,” she said with a playful shrug. “You’re not exactly subtle when you’re uncomfortable.”

Sid scratched the back of his neck, feeling a mix of embarrassment and something warmer, something he couldn’t quite place. “Well, thanks for dragging me up here anyway,” he muttered, glancing at the horizon to avoid her gaze. “Facing my fears and all that.”

Maggie smiled, a teasing glint in her eye. “That’s what I’m here for. It's important to step out of your comfort zone, now and again. Otherwise, you’ll never know what you’re capable of.”

Sid chuckled under his breath. “You make it sound so noble, but I’m pretty sure you just enjoy watching me squirm.”

“Maybe a little,” Maggie admitted, her grin widening. “But I also think you sell yourself short. You’re braver than you think. You climbed up here, didn’t you?”

He gave a small shrug. “Only because you dared me.”

“And yet, here you are.” She nudged his shoulder with hers, the small gesture oddly reassuring. “That counts for something.”

Sid finally allowed himself to smile, though it was faint. “I guess.”

They stood there for a moment, the city stretching out beneath them, bathed in the golden hues of the setting sun. The view was breathtaking, and Sid couldn’t deny that there was something exhilarating about being up so high, even if his legs still felt a little wobbly.

“So, what’s next on this little adventure of yours?” he asked, half-expecting her to suggest something even more outrageous.

Maggie tapped her chin, pretending to think. “Hmm. I could always make you do something really crazy, like climb back down and do it all over again.”

Sid gave her a look. “Not a chance.”

She laughed, the sound light and infectious. “Relax, I’m not that cruel. I think you’ve earned a bit of a break for now.”

Sid let out a mock sigh of relief, but he couldn’t help but notice the way Maggie’s eyes sparkled when she laughed, or the way her hair caught the light as the breeze played with it. There was something about her—something he couldn’t quite put into words but found himself drawn to nonetheless.

As if sensing his thoughts, Maggie turned to him, her expression softening. “You know,” she said, her voice quieter now, “I’m really glad you said yes to this. To today.”

Sid met her gaze, caught off guard by the sincerity in her tone. “Yeah?”

“Yeah,” she said with a small nod. “It’s been... fun. More fun than I’ve had in a while.”

Sid felt his chest tighten slightly, a warmth spreading through him that had nothing to do with the setting sun. “Yeah,” he said softly. “It has.”

The sun had dipped lower into the horizon by the time they settled back down on the rooftop ledge. The orange and pink hues painted the skyline, and the chatter of distant city life had faded into a quiet hum. Sid stretched his legs out, leaning back on his palms as Maggie sat cross-legged beside him, the breeze gently tousling her hair.

"Alright," Maggie began, her tone casual but her eyes alight with something thoughtful. "Final dare of the day."

Sid groaned dramatically. “Should I be worried?”

Maggie smirked but softened it with a nudge of her shoulder. “Don’t worry, it’s not dangerous or humiliating this time. I promise.”

“That’s a relief,” he muttered, though he couldn’t help the small smile tugging at his lips. “Alright, what is it?”

Maggie turned to face him fully, her expression serious but kind. “I dare you to tell me something you’ve never told anyone else. Something you keep to yourself.”

Sid blinked, his stomach tightening at her words. “That’s… pretty intense for a dare.”

She tilted her head, her voice softening. “It doesn’t have to be your deepest, darkest secret. Just something real. Something you’ve been holding onto.”

Sid looked away, his gaze falling to the edge of the roof as his hands fidgeted in his lap. He wasn’t sure why this dare felt heavier than the rest—why her words seemed to linger in the air, coaxing him to drop his guard.

After a long pause, he sighed. “Alright,” he said quietly, his voice barely audible above the wind. “You want real? Here it is.”

Maggie waited patiently, her gaze steady and unwavering.

“There’s this friend of mine,” Sid began, his throat tightening. “Scott. We’ve been friends since high school. He’s the kind of guy who just... charges through life, you know? No hesitation, no fear. He’s always had these huge dreams, and somehow, he made me believe in mine too.”

He paused, his fingers curling against his palms. “When I got into college, I thought I was doing the right thing. Like, finally taking a step forward, making something of myself. But when I came here… I don’t know. I felt like I was leaving him behind. Like I let him down.”

Maggie’s brows knit together as she leaned closer, her voice soft. “Why would you think that?”

Sid swallowed hard, his jaw tightening. “Because we made all these plans together. To stick it out, to build something. And then I just... left. He’s still back home, fighting for what we talked about, and I’m here, trying to figure out if this was even worth it.”

The weight of his confession hung between them, the vulnerability raw and unfamiliar. Maggie didn’t say anything for a moment, letting his words settle.

When she finally spoke, her voice was gentle, almost a whisper. “It sounds like you care about him a lot.”

“I do,” Sid admitted, his voice hoarse. “He’s my best friend. But sometimes, I feel like I’m just... watching him from a distance, you know? Like I’m not part of his life anymore. And that kills me.”

Maggie reached out, placing her hand over his. The gesture was simple, but it grounded him in a way he didn’t expect.

“You’re being too hard on yourself, Sid,” she said softly. “You didn’t abandon him. You’re just... finding your own way. And maybe he knows that. Maybe he’s proud of you for it.”

Sid glanced at her, his chest tightening at the sincerity in her gaze. “You think so?”

“I do,” she said with a small smile. “And if he’s anything like the way you talk about him, I’m pretty sure he knows how much he means to you.”

For a moment, Sid didn’t know what to say. The vulnerability he’d just laid bare felt less daunting now, less like a weakness and more like a part of him he didn’t have to carry alone.

“Thanks, Maggie,” he said quietly, his voice earnest.

She smiled wider, squeezing his hand before letting go. “Anytime. That’s what friends are for, right?”

Sid laughed softly, the tension in his chest easing. “Yeah. Friends...”

The quiet that followed felt comfortable, the kind that only came after laying your heart bare and finding that the person sitting beside you hadn’t run away. Sid let out a breath he didn’t know he’d been holding, his fingers drumming idly on his knee.

“So,” he began, breaking the silence, “that’s gotta fulfill your dare quota, right? Pretty sure I’ve bared my soul enough for one day.”

Maggie’s lips curved into a mischievous smile, and she gave a small shrug. “I guess you have earned a breather. But since you’re keeping track… yeah, I’d say you’re good.”

Sid raised an eyebrow, sensing a catch. “Just like that? No follow-up challenge? No loopholes?”

She shook her head, her grin widening. “Nope. So…” Maggie tilted her head, studying him with that glint of curiosity that always kept him on edge. “You get your prize. One dare, from you to me. Fair’s fair, right?”

Sid blinked, caught off guard. “Wait, really? You’re just… handing me the reins?”

“Why not?” Maggie said, leaning back on her palms. “Think of it as my way of saying thanks for humoring me all day.”

He hesitated, glancing out at the skyline as he mulled over the idea. He wasn’t exactly the creative type when it came to these things—Maggie had already proven she was the master of dares. Still, he wasn’t about to pass up the opportunity to turn the tables.

“Alright,” Sid said finally, sitting up straighter. “I dare you to… I don’t know, do something you wouldn’t expect to do in your everyday life.”

Maggie raised an eyebrow, her expression somewhere between amused and intrigued. “That’s pretty vague, Sadowskyj.”

“Well, sorry if I’m not as good at this as you,” Sid shot back, his tone light. “Just… you know, something maybe you think about, but you're not sure you should do. Surprise yourself. Do it.”

For a moment, Maggie didn’t respond. Her gaze flickered over him, her eyes narrowing slightly as if she were weighing her options. Then, to Sid’s utter disbelief, she shifted closer.

Sid’s breath hitched as the space between them shrank. Her expression was unreadable, a mix of determination and curiosity, and he wasn’t sure if he should brace himself or run.

“Maggie, what are you—”

Before he could finish, she leaned in and kissed him.

It wasn’t hesitant or tentative. It was bold, confident, and completely unexpected. Her lips were warm, soft, and lingered just enough to send a jolt through him. For a second, Sid froze, his mind racing to catch up with what was happening.

Then, just as quickly as it started, Maggie pulled back, her cheeks flushed but her grin undeniably smug. “Surprised?”

“Uh…” Sid blinked, still processing. “Yeah. Yeah, I’d say that’s one way to put it.”

Maggie laughed, sitting back with an air of satisfaction. “You told me to surprise myself, right? Well, I figured… why not? It's something I’ve thought about.”

Sid stared at her, his heart still racing. “You’ve thought about… kissing me?”

She shrugged, trying to play it cool, but her pink cheeks betrayed her. “Yeah. Sometimes. Don’t get too cocky about it, though. It’s not like I was planning to tell you.”

Sid let out a shaky laugh, rubbing the back of his neck. “Well, that's me flattered.”

Maggie tilted her head, studying him with a playful glint in her eyes. “You didn’t... hate it, though. Right?”

Sid hesitated, not because he was unsure of his answer, but because he wasn’t entirely sure how to say it without embarrassing himself. Finally, he settled on honesty. “No. I didn’t hate it.”

“Good,” Maggie said simply, as if that settled it. “Now it’s your turn.”

“What?” Sid blinked. “My turn to what?”

“To do something unexpected,” she said, her grin widening. “Come on, you can’t just let me outdo you. That’s no fun.”

Sid groaned, running a hand through his hair. “You’re impossible, you know that?”

“And yet, here you are,” Maggie teased, leaning her chin on her hand. “So? What’s it gonna be?”

Sid hesitated for just a moment, his gaze flicking to Maggie's lips, then back to her eyes. Her smirk softened, the usual teasing in her expression replaced by something more open, almost vulnerable. He felt his pulse quicken, the weight of her challenge lingering in the air between them.

He closed the gap slowly, giving her just enough time to anticipate it, to feel the electricity building between them. When their lips finally met, it wasn’t tentative like hers had been. It was deliberate, heated, and full of the intensity he’d been holding back for far too long.

Maggie responded immediately, her hand instinctively reaching up to his shoulder, clutching at the fabric of his shirt as if to ground herself. His kiss deepened, his hand sliding to the back of her neck, fingers threading through her hair. She tilted her head, giving in to the moment, and Sid felt a surge of confidence as she leaned into him.

The world around them blurred, the faint hum of the street below and the distant chatter of passersby fading into nothing. All Sid could focus on was the warmth of her lips, the way she tasted faintly of coffee, and the intoxicating pull of her body against his.

Maggie broke away first, gasping softly for air, her cheeks flushed and her lips slightly swollen. For a moment, they just stared at each other, the weight of what had just happened settling between them.

“Alright,” Maggie said breathlessly, her voice shaky but laced with humor. “You win.”

Sid chuckled, his forehead resting lightly against hers. “I wasn’t trying to win. Just trying to… I don’t know, meet you halfway.”

She laughed softly, her hand still clutching his shirt. “Halfway, huh? Felt more like you went all in.”

Sid grinned, his fingers trailing lightly down her arm. “Couldn’t let you think I wasn’t up for the challenge.”

Maggie pulled back slightly, her eyes sparkling with amusement and something deeper. “You’re full of surprises, Sadowskyj. I’ll give you that.”

“And you,” Sid replied, his voice quieter now, “are a bad influence. But I guess I can’t say I mind.”

Maggie smiled, her fingers brushing lightly against his chest before she finally let go. “You’ll survive. So, what’s next?”

Sid raised an eyebrow, a smirk tugging at his lips. “You’re already thinking about the next dare?”

“Always,” she teased, standing up and straightening her jacket. “But I’ll give you a break… for now. You’ve earned it.”

Sid laughed, shaking his head as he stood to follow her. “I don’t know if I should be relieved or scared.”

“Probably both,” Maggie quipped, glancing back at him with a wink.

And as they made their way back down the fire escape, Sid couldn’t help but smile, his mind still reeling from what had just happened. One thing was for sure—Maggie was nothing like anyone he’d ever met, and he wasn’t sure if that was terrifying or exhilarating. Maybe it was both.

#tom blyth #scott and sid #sid sadowskyj #tom blyth x reader #tom blyth x fem!reader #original character #sid sadowskyj x reader

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