Crestwood Academy for Young Ladies - Forced Fem Fantasy

Chapter Eight: The Real Day One

Dylan woke up the next morning, the events of the previous day replaying in his mind. He stared at the ceiling for a moment, wondering if it had all been a strange dream. But the soft fabric of the camisole and shorts brushing against his skin quickly reminded him that it was all real.

He sighed and sat up, swinging his legs over the side of the bed. It was still early, but he wanted to get dressed before the others started moving around. The thought of facing the day in his new uniform wasn't exactly exciting, but at least he could get it over with.

Heading to his dresser, Dylan immediately noticed something odd. His boxers, the ones he'd worn yesterday, were nowhere to be found. Panic crept up as he remembered—he'd left them in the bathroom last night, along with his uniform in the laundry hamper.

"Great," he muttered to himself.

Without wasting any more time, he slipped out of his room and headed down the hall toward the communal bathroom. The hallway was quiet, and as he pushed open the door to the washroom, he quickly scanned the room for his clothes. The hamper was empty. There was no sign of his uniform, and more importantly, no sign of his boxers.

Defeated, Dylan brushed his teeth and splashed some water on his face, trying to figure out what to do next. He couldn't very well go without underwear, could he? He quickly made his way back to his room, hoping maybe he'd find something else in his dresser.

Opening the drawers, his heart sank further. One drawer was filled with panties—white, pink, and white with pink stripes. He stared at them, unsure of what other options he had. After a moment of hesitation, he grabbed a white pair, figuring they were the least feminine. He closed his eyes, slipped them on, and then quickly dressed in the rest of his uniform, opting for the over-the-calf socks again.

As soon as he was ready, he headed to the common space where the girls had told them to meet. The morning sun was starting to filter through the windows, casting a soft glow over the room. When he arrived, he saw Kyle already sitting there, his legs crossed, looking oddly calm.

Dylan took a seat beside him. "You're up early."

Kyle nodded, glancing down at his legs. "Yeah. Couldn't really sleep."

Dylan noticed something. "You went with the pantyhose today, eh?"

Kyle shrugged. "I was too cold yesterday with just the socks. They said this would be warmer." He seemed surprisingly comfortable with it, and Dylan couldn't help but feel a little less embarrassed about his own situation.

Before they could say anything else, Marcus walked in, wearing pantyhose again today. He plopped down next to them, looking a little flustered, and immediately whispered, "Hey, uh, you guys didn't happen to see my boxers, did you?"

Kyle and Dylan exchanged glances, and then Dylan shook his head. "Yeah... we lost ours too."

Marcus's face fell. "What? What did you guys do for underwear then?"

Kyle shrugged again, adjusting his pantyhose. "I'm not wearing any under these. It's fine."

Dylan felt his cheeks heat up. "I, uh... I found some panties in the dresser. Just wore those."

Marcus's eyes widened slightly, but then he let out a breath. "Okay. Good. I thought I was the only one." He leaned in closer. "I did the same thing. Pink stripes."

Dylan nodded, relieved that he wasn't the only one in this awkward predicament. "Yeah, let's not mention this to Aaron, though."

"Agreed," Kyle said with a grin.

Just as they were settling into their conversation, the door opened again, and the four mentors walked in together, their usual composed, confident air about them. They looked around, noticing that Aaron was still missing, but for now, they ignored it.

Sophie smiled warmly at the group. "Morning, boys."

"Morning," they mumbled in unison.

"Alright," Sophie continued, "while we wait for Aaron, let's go over your daily schedules. Marcus, Dylan, you'll be with me and Emily for most of the day. Kyle, you'll be with Aaron, Olivia, and Hannah."

Dylan nodded, though he felt a bit nervous about what was to come. "So... what's on the agenda?"

Sophie beamed. "Our first class this morning is 19th-century Literature. After that, we have Finance, then a lunch break, followed by European History, Geography of the Americas, and then you guys have Etiquette Basics."

Hannah chimed in for Kyle. "And for us, it's Calculus, Baking 101, then lunch, Women in Film, Ancient History, and then you also have Etiquette Basics."

As she finished speaking, the door swung open, and Aaron walked in, looking slightly disheveled and clearly annoyed.

"Nice of you to join us," Emily said with a raised eyebrow. "You're late."

Aaron shrugged, clearly not bothered. "Yeah, well, I couldn't find my underwear."

Sophie exchanged a glance with Emily before replying, "They were in the top right drawer of your dresser, just like everyone else's."

Aaron shot her a sarcastic look. "Thanks. I figured that out on my own."

Emily didn't seem amused. "You do realize tardiness gets reported to Headmistress Beaumont, right?"

"Go ahead," Aaron muttered, rolling his eyes. "I don't care."

Olivia placed a hand on Emily's arm, stopping her from arguing further. "Let's just move on."

With that, Sophie continued. "Your textbooks and notebooks are on the table behind you. Make sure to grab them before heading to class. Oh, and there's one more thing."

The boys exchanged confused looks.

Sophie smiled again, this time a little softer. "Headmistress Beaumont has requested that, to make the other students comfortable, you boys will be going by female names during class."

Dylan blinked. "Wait... what?"

Emily stepped forward, her tone gentle but firm. "It's Beaumont's rules. We know it might feel strange at first, but it's all about helping you blend in with the rest of the students."

Before Dylan could ask any more questions, Sophie nodded toward him. "Your name will be 'Diana' in class."

Dylan's stomach dropped slightly, but he nodded, not wanting to cause a scene. "Okay."

Emily turned to Marcus. "You'll be 'Maya.'"

Marcus grimaced slightly but accepted it. "Got it."

Hannah smiled at Kyle. "You'll be 'Katie.'"

And finally, Olivia looked at Aaron. "Your name will be 'Alana.'"

Aaron's face darkened, but he didn't argue. He simply muttered something under his breath and grabbed his notebook from the table.

As the group gathered their materials and prepared to leave for class, Sophie gave them one final encouraging smile. "Remember, it's all about adjusting. You'll get used to it."

Dylan wasn't so sure. As he followed the others out of the common area, the unfamiliar feeling of the panties under his skirt made every step feel strange, but there was no turning back now.

Their new lives at Crestwood Academy had truly begun.