Chapter Thirty-Four: Shopping
Crestwood Academy for Young Ladies - Forced Fem Fantasy
After a week that felt like it went on forever, Saturday morning finally arrived. Dylan groaned as he rubbed his eyes, barely awake as the soft light filtered through the blinds. After the chaos of the past week, a part of him hoped today would be quiet. But he knew better. Every day was another testâanother reminder of how far he'd have to bend to fit the mould.
He got dressed without much thought, throwing on a pair of ripped mom jeans and a cropped baby tee with an intricate floral pattern. His old wardrobe was almost a distant memory. He glanced in the mirror and shrugged, good enough.
When he wandered into the common room, he found Kyle and Aaron already slouched on the couches. Their expressions mirrored his ownâexhausted and resigned.
"Morning," Dylan muttered, collapsing into the seat next to them.
Kyle yawned. "Morning. Ready for another day of pretending we're not miserable?"
Aaron just grunted in agreement
Marcus tried lifting the mood. "Come on, not everything about this place sucks."
They hadn't been sitting long when the girls walked in. Sophie, Hannah, Olivia, and Emily stood before them, with looks that told Dylan they had plans for the day. Big plans.
"Alright, boys," Sophie said, flashing a grin that hinted at mischief. "We've got something special for you today. Appointments at some local boutiques. It's time to pick out your gowns for the Annual Debutante Ball!"
Dylan felt his stomach twist. He could feel Kyle tense up beside him, while Aaron's expression darkened.
"You've got to be kidding," Aaron said, irritation dripping from his voice. "When is enough enough? I just want a day of nothing!"
Sophie raised a brow, folding her arms. "I get it. You're tired, but the Ball is huge at Crestwood. Even though it's only a mid-term grade, it's basically the exam of the year. Everyone expects you to show up looking and acting the part. It's a tradition."
Kyle rolled his eyes. "Yeah, but some of us didn't exactly sign up for this."
Hannah's tone softened as she stepped forward. "We understand. Really. But you are the ones who agreed to come here. There's a reason we push you guysâthere's a lesson in all of it."
Aaron exhaled sharply, staring at the floor. "It's still ridiculous."
Dylan shifted in his seat, the tension building in the room. He wasn't thrilled either, but what was the point in arguing? They'd been through this before. Pushing back felt like slamming into a brick wall. The girls always had an answer.
Sophie glanced at her friends, her expression softening. "Okay, I get it. You're frustrated. But... I have an idea." She paused, waiting for a response, but the boys just stared back at her. She exchanged a look with the other mentors, then continued. "What if we turn it into a competition?"
Dylan frowned. "A competition?"
Sophie's face lit up. "Exactly! We'll judge you guys based on how well you embrace the experience. Whoever is the most convincingâwhoever really goes all inâwins a prize."
Aaron raised an eyebrow, clearly not buying it. "What kind of prize?"
Sophie smirked. "That's a secret. But I promise, it'll be something you'll actually want."
Dylan glanced at Kyle, who looked as unconvinced as he felt. Aaron crossed his arms, about ready to shut the whole thing down.
Before anyone could argue, Marcus, who had been sitting quietly by the window, leaned forward and looked directly at Aaron "Come on, guys. We've gotten this far. What's a little more pretending? You guys aren't gonna let me win that easily are you?" He was clearly prodding Aaron's competitive nature.
Aaron let out a long, reluctant sigh, clearly weighing his options. "Fine. I'm in. But if the prize sucks, I'm taking it out on Marcus."
Sophie grinned and clapped her hands together. "Perfect! We'll be judging all day, so make sure you bring your best game. Let's make it fun, alright?"
Dylan forced a smile, the weight of the day already pressing on him. "Whatever."
The first boutique was a sea of soft pinks and creams, with delicate floral patterns and glittering chandeliers overhead. As soon as the boys walked in, they were greeted by an overly enthusiastic saleswoman.
"Oh my, aren't you all just precious!" she chirped, clapping her hands. "We are going to find the most gorgeous gowns for you girls today!"
Dylan stifled a groan but managed a polite smile. "Can't wait," he said through gritted teeth, glancing at Kyle, who just rolled his eyes.
As soon as the saleswoman turned away to start pulling gowns, Kyle leaned over to Dylan. "This is gonna be rough," he whispered, eyeing the racks of pastel dresses that seemed to stretch on forever.
"Just smile and nod," Dylan muttered back.
Marcus, however, was fully embracing the moment. He strode over to one of the mannequins and dramatically ran his fingers along a sparkling red gown. "Okay, this is the one! I mean, look at it. I need!"
Kyle smirked. "You're not even trying to fight this anymore, are you?"
"Why fight what you can slay?" Marcus shot back with a grin.
Aaron, on the other hand, looked like he was about ready to explode. "This is a nightmare," he muttered, folding his arms. "I'm not wearing anything frilly or pastel. I'll just burn it."
"Relax, princess," Dylan said, smirking.
The saleswoman soon returned with an armful of gowns, practically skipping over to them. "Here we go, ladies! I've got the perfect selections for each of you! Let's get started!"
One by one, the boys were shuffled into dressing rooms. Dylan stared down at the gown in his handsâan explosion of pink tulle with an off-the-shoulder neckline. With a resigned sigh, he slipped it on and looked at himself in the mirror. Great. I look like a rejected Barbie doll.
When he stepped out, the saleswoman gasped. "Oh, Diana, darling! You look stunning!"
Dylan gave a half-hearted twirl. "Yup. A real princess," he said flatly, eyeing Sophie from across the room, who raised an eyebrow as if daring him to sell it more.
With a dramatic sigh, Dylan tossed his hair and spun again, letting the gown flare out. "I mean, honestly," he said in an exaggerated voice, "I feel like sleeping beauty, waiting for some rich prince to wake me up. It's just... so dreamy."
Kyle, who was standing nearby in a pale yellow gown decided he was going to go all in. "Sleeping Beauty? Girl... you look like a cheap knock-off doll that no one ever plays with."
Dylan smirked. "Sounds like you're jealous."
Kyle rolled his eyes. "Girl please, look at me, it's understated elegance." He turned to the mirror, giving his gown a once-over before faking a delicate twirl. "See? Less is more."
Not to be outdone, Marcus emerged in a stunning red gown with a plunging neckline and strutted to the center of the room. "Okay, I'm just going to say itâI own this look," he said, doing a little catwalk spin. "I mean, it's a little daring, but sometimes you've just got to make a statement, right?"
"Right," Dylan said with a grin. "Except your statement says 'look at me' way too loud."
Kyle nodded in agreement with Dylan. "Less is more, honey."
Then Aaron stepped out, looking like he'd just been forced to walk the plank. His dress was a hot pink with a modest neckline and a flowy skirt. "I hate this," he said, his voice flat. "Like, really hate this."
Sophie smirked from the corner. "Come on, Aaron. Give us a little spin. It won't kill you."
Aaron's eyes narrowed. "Oh, I'm sure it will." Still, with a heavy sigh, he turned stiffly on the spot, barely moving the skirt. "There. Happy?"
"Ecstatic," Sophie teased.
As they cycled through more dresses, the banter only got louder. Dylan was now in a bright green gown with a glittering bodice, dramatically striking poses in front of the mirror. "Ma'am you've out done yourself. Honestly, this might be the one," he said, flipping his hair as he turned to the sales women.
Kyle, in a light blue number with puffed sleeves, shook his head. "You look like you belong in a Disney movie."
"Yeah, well, at least I'm not swimming in fabric like you," Dylan shot back, eyeing Kyle's overly poofy dress. "What is that, a parachute?"
Marcus joined in, now in a sleek black gown that hugged his frame perfectly. "Okay, but this," he said with a smug smile, "All of you are playing checkers while I'm out here playing chess."
Kyle snickered. "Calm down, Miss Universe."
Aaron, however, was still not playing along. He crossed his arms and grumbled as the saleswoman gushed over the bold blue gown he'd been forced into. "You look so sophisticated!" she exclaimed, clapping her hands together.
Aaron didn't even look in the mirror. "Yeah, sure. Whatever."
Dylan couldn't help but laugh. "Come on, Aaron. Give us something."
Aaron sighed and gave the smallest spin possible. "There. I spun. Are we done?"
Dylan grinned. "Not even close."
After what felt like an eternity of trying on gowns, the saleswoman beamed as she led the boys back toward the front of the store. "You ladies were such a joy! I'll make sure everything is ordered and delivered on time!"
Sophie stepped forward with a grin. "Actually, we need to head back to finalize the orders. You girls can hang out at the park down the street while we finish up."
"Wait, what?" Kyle asked, looking surprised. "We don't get to pick our own dress?"
Hannah smiled sweetly. "Nope. You'll find out later."
Dylan groaned. "Great. So, we're just going to be surprised?"
Sophie gave him a wink. "Exactly."
With that, the boys left the mentors behind while they waited at a small park nearby. The boys sat on the benches, waiting for the inevitableâand wondering which of those ridiculous dresses they'd be stuck wearing at the ball.
"Dammit man, I was planning on picking the most basic one." Kyle expressed, rubbing his forehead.
Dylan shook his head. "Same dude. I hope they don't pick the big poofy one I was pretending to like so much. I was just trying to win the prize."
As the boys lounged around the park, stretched out on the benches, their conversation had died down to a comfortable silence. They had spent the time joking about their absurd dress-up experience, but now the novelty had worn off. Dylan leaned back, staring up at the sky, trying to forget how ridiculous he felt earlier, parading around in gowns.
Suddenly, the sound of footsteps brought them all back to reality. Sophie, Hannah, and the rest of the mentors approached with knowing smiles on their faces, clearly pleased with themselves.
"Well, well, well," Sophie began, arms crossed as she eyed the group. "I have to say, we're surprised. You boys really outdid yourselves."
Kyle sat up straighter, blinking. "Wait, really?"
Hannah nodded, grinning. "Totally. We expected at least one of you to crack, but you all played along way better than we thought, apart from Aaron."
"Marcus especially," Olivia chimed in, giving him a teasing look. "You were really into it."
Marcus shrugged with a sly smile. "Hey, if I'm going to do something, I might as well commit, right?"
Dylan glanced at Sophie, narrowing his eyes. "So, are you going to tell us which one of those hideous gowns we're getting?"
Sophie laughed. "Not yet. But you'll find out soon enough. For now, we thought you might want to know how much each gown costs."
Aaron groaned immediately. "Oh no. Here we go."
Emily pulled out a small notepad and flipped through it, her expression almost too delighted. "Okay, so... Dylan, your gown? A cool $800."
Dylan's jaw dropped. "What?"
Sophie grinned. "Yup. Worth every penny."
"Not from my wallet," Dylan muttered, shaking his head.
Hannah moved on. "Kyle, yours was $520."
Kyle practically choked.
Hannah, still smiling, "Marcus, your gown was the most expensive, coming in at $980."
Marcus raised his eyebrows, but he didn't seem all that fazed.
Aaron shifted uncomfortably, clearly dreading what was coming. Olivia gave him a mischievous smile before revealing the final number. "Aaron, yours was the cheapest. Only $320."
Aaron rubbed his face, groaning again. "I hate this so much."
Hannah waved her hand dismissively. "Oh, relax. You'll just need to get the money from your parents before the final fitting. Simple, right?"
"Simple?" Dylan echoed. "Have you met my parents?"
Sophie rolled her eyes playfully. "Come on, it's Crestwood. I'm sure your parents will be fine with it once they hear it's for the famous Crestwood Debutante Ball. You'll all come back later this week for the final fitting, and then we'll have everything tailored perfectly in time for the big night."
Aaron slouched further down in his seat. "Great. Can't wait."
As the group gathered their things and began walking back toward Crestwood, the boys exchanged glances, all clearly sharing the same reluctant feeling about having to wear those gowns again. The lighthearted banter from earlier had faded, replaced by the weight of knowing they had to convince their parents to shell out thousands for dresses.
As they neared the gates of Crestwood, the boys shared a look, already bracing themselves for the rest of the week and whatever else it was going to throw at them.