Crestwood Academy for Young Ladies - Forced Fem Fantasy

Chapter Thirty-Four: Shopping

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 test—another 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 own—exhausted 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 guys—there'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 convincing—whoever really goes all in—wins 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.