Crestwood Academy for Young Ladies - Forced Fem Fantasy

Chapter Five: Dressing the Part

Dylan stood in front of the closet, staring at the uniform like it was some foreign object. The blazer, skirt, and blouse hung there innocently enough, as if they were meant to be worn without a second thought. He could still hear Sophie's words in his head—just follow the rules.

A wave of disbelief washed over him again. Was this really happening? Were they actually supposed to wear this?

He heard a knock on the door, followed by Aaron's voice. "Dude, you ready?"

Dylan sighed and turned toward the door, opening it to find Aaron standing there, looking just as unsure as he felt. "Ready for what? To wear this?" Dylan gestured to the uniform, shaking his head.

Aaron grimaced. "I don't know, man. This is messed up. But what choice do we have? The girls made it clear we'll get in trouble if we don't."

Dylan nodded. The thought of facing Headmistress Beaumont after what happened earlier was enough to make him pause. There wasn't much wiggle room when it came to her rules.

"I guess we just get it over with," Dylan said, more to convince himself than Aaron.

The two boys exchanged a glance before they slowly moved toward their closets. Aaron unbuttoned his shirt, tossing it on the bed with an exasperated groan. Dylan followed suit, pulling off his jeans and feeling the strange weight of the situation settle in.

"I feel like this is some weird dream," Aaron muttered, unfolding the pleated skirt.

Dylan couldn't disagree. Everything about Crestwood Academy seemed like it was operating in a world with different rules. With a heavy sigh, he grabbed the blouse and slipped it on, buttoning it up one button at a time.

The fabric was soft, far softer than any shirt he had ever worn before. It felt...different. Not necessarily bad, but different. He glanced over at Aaron, who was struggling with the skirt.

"I don't even know how to put this thing on," Aaron said, his face a mix of frustration and confusion.

Dylan chuckled despite himself. "There's a zipper on the side."

Aaron found the zipper and slipped the skirt on, grumbling under his breath. Dylan grabbed his own skirt and zipped it up, the waistband sitting surprisingly comfortably at his hips.

Standing there, fully dressed in the Crestwood uniform, Dylan looked at himself in the mirror. The reflection staring back at him felt alien—a version of himself that shouldn't exist. Yet here he was, in a skirt, blouse, and blazer, the same as any other student at the school.

Aaron finished adjusting his uniform and glanced at Dylan. "We look ridiculous."

"Tell me about it," Dylan muttered.

Just as they were about to step out of the room, Marcus and Kyle appeared in the hallway, both dressed in the same uniforms, looking just as uncomfortable.

"This is so messed up," Marcus said, tugging at the hem of his skirt like it might magically grow longer if he pulled hard enough.

Kyle let out a frustrated sigh. "I don't even know how we ended up here, man. This was supposed to be an easy semester."

Aaron shook his head. "Yeah, easy. Right."

A tense silence fell over the group, each of them fidgeting awkwardly in their new attire. After a few moments, Marcus spoke up. "So...what now?"

Dylan shrugged. "I guess we find the girls and let them know we did it."

The group reluctantly made their way down the hall, the sound of their unfamiliar shoes echoing off the polished floors. The girls' dorm wasn't far, and they found themselves knocking on Sophie's door again sooner than they'd hoped.

Sophie opened the door, her eyes widening for a split second before a knowing smile crept onto her face. Olivia and Hannah appeared behind her, taking in the sight of the boys in their uniforms.

"Well," Sophie said, folding her arms, "I have to say, you all clean up nicely."

Dylan felt a flush of embarrassment creeping up his neck. He could tell from the looks on the girls' faces that they were enjoying this far more than he and the others were.

"Yeah, yeah, we're wearing the uniforms," Marcus said, crossing his arms. "Now what? You said we had to wear them, and we did."

Olivia stepped forward, eyeing them critically. "Almost, but not quite. You're missing something."

Aaron frowned. "What do you mean?"

Sophie raised an eyebrow and motioned toward their legs. "The socks and shoes. You're supposed to be in full uniform, and that includes the proper socks. You've got three options: ankle socks, over-the-calf socks, or pantyhose. You'll find them in the top left drawer of your chest of drawers."

Olivia smirked as she looked them over. "It's a bit chilly today. I'd suggest the pantyhose."

Dylan's stomach dropped. Pantyhose? The thought made his skin crawl.

"I'm not wearing pantyhose," Aaron said firmly. "I'll stick with the ankle socks, thanks."

The other boys murmured in agreement, though Dylan hesitated. He didn't like the idea of pantyhose either, but the over-the-calf socks sounded like a reasonable compromise. His legs were cold enough already.

"Shoes are in the closet," Sophie added, nodding toward their rooms. "Mary Jane heels, standard Crestwood uniform."

"Great," Marcus muttered under his breath. "Just great."

With that, the boys turned and trudged back to their rooms. Dylan opened the top drawer of his chest of drawers and, sure enough, found neatly folded pairs of ankle socks, over-the-calf socks, and pantyhose. He grabbed the over-the-calf socks and quickly pulled them on, feeling somewhat relieved that he didn't have to deal with the pantyhose. He then grabbed the Mary Janes from the closet and slipped them on.

When he headed to Aaron's room to regroup with the others, he found Aaron, Kyle, and Marcus already there, all in their full uniforms, including the socks and shoes. Dylan immediately noticed that Marcus had opted for the pantyhose.

Aaron, apparently noticing as well, grinned. "Seriously, Marcus? You went with the pantyhose?"

Marcus shrugged, trying to play it cool, but a hint of embarrassment showed on his face. "It's cold, okay? And Olivia said they were better for today."

Aaron snickered. "Sure, man, whatever you say."

Dylan exchanged a glance with Kyle, who was also trying to suppress a laugh. The tension of the situation seemed to ease just slightly, even if it was only for a moment.

Just then, Sophie, Olivia, and Hannah peeked their heads into the room, their eyes sweeping over the boys. Sophie smiled approvingly. "Well, now you're in full uniform. Much better."

Olivia nodded. "You'll fit right in now. Lunch is in the dining hall in an hour. We expect to see you there, fully dressed, of course."

Hannah added, "You'll have the rest of the day to yourselves after that. Your typical routine will begin tomorrow."

Dylan's stomach churned at the thought of their "routine," but he pushed the feeling aside. For now, lunch was the next step, and at least they wouldn't be forced into more unfamiliar situations—at least not for a few more hours.

The girls left the room, leaving the boys standing there in silence.

Marcus looked down at his legs, shifting uncomfortably. "I'm never going to get used to this."

Aaron sighed. "None of us are, man. But we've got no choice. We just have to get through this semester."

Dylan nodded in agreement, feeling the weight of the situation sink in again. One semester. Just one semester.

And then, it would all be over.

Or at least, that's what they hoped.