Crestwood Academy for Young Ladies - Forced Fem Fantasy

Chapter Twenty-Four: Personal Stylist

A soft knock on the door pulled Dylan from his sleep. Still groggy, he rubbed his eyes and called out, "Come in."

The door creaked open, and to his surprise, Sophie stepped inside, a playful grin on her face. "Your personal stylist is here for your appointment," she teased.

Suddenly, the events of last night rushed back to Dylan, and he chuckled, sitting up in bed. "Right... I forgot about that."

Sophie waved him toward the bathroom. "Go ahead, take your time. I'll sort through your closet."

Dylan stood and stretched, still feeling the lingering haze of last night's laughter. As he walked to the bathroom, he glanced down at his nails, the green polish still there, complete with the tiny 'S' Sophie had painted on his thumbnail. A smile crept across his face. He couldn't help but laugh at the absurdity of it all.

In the bathroom, he brushed his teeth, washed his face, and carefully applied the moisturizer they'd been instructed to use. When he returned to his room, Sophie had two outfits laid out on his bed, her hands on her hips as if she were presenting her proudest creation.

"Okay," Sophie said, "I've got two options for you. Both very autumnal."

Dylan surveyed the choices. The first outfit was a t-shirt dress paired with a chunky knit sweater. The second option featured black flare leggings, a white turtleneck, and an oversized sweater.

He felt a pang of regret for asking Sophie to help. "Autumnal," he repeated with a weak grin, avoiding the leggings altogether. "I guess I'll go with the dress and sweater."

Sophie nodded approvingly. "Good choice. Just remember, you've got to wear the belt over the dress and tuck the sweater into it to get that cropped look. Trust me, it'll be cute."

Dylan gave her a look, but before he could say anything, Sophie was already heading for the door. "Oh, and don't forget—put on a pair of pantyhose and those knee-high boots from your closet. You'll thank me later."

After she left, Dylan sighed and rummaged through his dresser, reaching for his usual underwear. But to his dismay, the only pairs left were bright pink. Great. Whatever, he thought, grabbing them and slipping them on.

He finished dressing, following Sophie's instructions to the letter. To be fair, the outfit looked good. It was just... a lot more girly than he was used to.

He headed to the common area, where Marcus and Emily were already waiting. Marcus was dressed in a red leather skirt, a cream-colored sweatshirt, and matching red flats. Emily was chatting with him, her eyes lighting up when she saw Dylan approach.

"Dylan! Looking very chic," she said, clearly impressed.

Marcus turned to look at him and smiled. "See? Told you Sophie knew what she was doing."

Dylan rolled his eyes but couldn't help but admit they were right. Before he could respond, Hannah entered the room, her eyes widening as she took in Marcus and Dylan's outfits.

"Well, don't you two look fashionable," Hannah said, a little surprised. She gave Emily a knowing look. "Should I start styling Kyle too?"

As if on cue, Kyle walked in, overhearing the end of the conversation. "Start doing what for me?" he asked, clearly puzzled.

Hannah pointed to Dylan and Marcus. "That."

Kyle glanced at them and raised an eyebrow. "Yeah, I'm good. Oversized band tees and jeans are more my style."

Everyone laughed, and Dylan found himself smiling too, the nerves about his outfit fading away as they settled into their usual banter.

Though he hadn't expected the day to start like this, he had to admit—it wasn't half bad.