Crestwood Academy for Young Ladies - Forced Fem Fantasy

Chapter Thirty-Six: Busy Week Ahead

Monday morning came too soon for Dylan. The moment his eyes opened, the weight of the week ahead hit him like a tidal wave. Final practices for the talent show, learning to waltz for the ball, gown fittings, equestrian club—it was all crammed into his schedule. But first, he had to deal with Maggie.

He groaned quietly as he sat up, swinging his legs off the bed. The memory of the 1950s-inspired gown Maggie had shown him last week made his stomach churn. The layers of petticoats, the frills, the cinched waist—it was all too much. But there was no avoiding it. Maggie was expecting him before breakfast, and the sooner he got through this, the better.

Dylan quickly dressed and hurried to Maggie's studio, his mind buzzing with anxiety. He barely noticed the crisp morning air as he walked across campus, too focused on the impending fitting. When he arrived at the small design studio, the door was already open, and Maggie was inside, adjusting a mannequin draped in fabric.

"Good morning, Diana!" Maggie greeted him with a bright smile, her blonde ponytail bouncing as she moved. "I've been dying to see how the dress fits on you. I made a few final adjustments over the weekend. I think you're going to love it."

Dylan forced a smile, slipping into his bubbly, sweet persona. "I can't wait!" he said, trying to sound enthusiastic. "I'm sure it's perfect."

Maggie led him over to a large mirror, where the dress hung on a rack. Dylan's eyes drifted over it, and his heart sank. The design hadn't changed—if anything, it looked even more frilly than before. The white pleated skirt had layers upon layers of petticoats, and the bold red top was tailored to fit like a blazer, with exaggerated frilly shoulders. A wide white belt was the final touch, cinching in the waist to create an hourglass figure.

"Go ahead and put it on!" Maggie urged, handing him the dress. "I'll help with the zipper."

Dylan nodded, stepping into the changing area. As he slipped into the dress, he immediately felt the constriction of the fabric around his waist. The petticoats rustled as he pulled the skirt into place, and when Maggie zipped him up, the waistline tightened even further.

When he stepped out of the changing area and stood in front of the mirror, the reflection that stared back at him was surreal. The dress was perfectly fitted, hugging his frame in all the right places—if "right" meant making him look like a caricature from the 1950s. Dylan's shoulders slumped slightly under the weight of the frills, but he quickly straightened up, putting on his best "Diana" smile.

"Oh my god, you look amazing!" Maggie squealed, circling him and adjusting the skirt. "This is going to be the highlight of the show. You're going to steal the spotlight!"

Dylan twirled slowly in the mirror, pretending to admire how the dress moved, even though every swish of the petticoats made him feel more trapped. "It's... stunning," he said, forcing himself to sound excited. "I feel like I've stepped right out of a magazine."

Maggie beamed, clearly proud of her work. "You're such a natural, Diana. This dress was made for you."

He bit back the urge to roll his eyes. Instead, he nodded along, letting Maggie fuss over the fit. She adjusted a few seams, pinned the shoulders to sit just right, and tightened the belt a little more. The whole time, Dylan focused on maintaining his persona, knowing he had to sell this, not just to Maggie but to himself.

As Maggie worked, she kept up a stream of chatter about the upcoming runway show, how important it was to her, and how she couldn't have asked for a better model. Dylan kept smiling and nodding, even as the discomfort grew. Every compliment about how "stunning" and "classy" he looked in the outfit made him feel more distant from himself, more like Diana and less like Dylan.

Finally, after what felt like an eternity, Maggie stepped back and clapped her hands together. "Perfect! You're all set. We'll do one final fitting on Friday morning, just to make sure everything's flawless for the show."

Dylan nodded, relief washing over him at the thought of getting out of the dress—at least for now. "Thanks, Maggie. I'll be ready."

Maggie gave him a hug, squeezing him tightly before helping him out of the dress. As Dylan stepped back into his regular clothes, he couldn't help but feel a strange sense of loss. The contrast between the frilly gown and his plain uniform was stark, and for a brief moment, he felt like two different people.

"Don't forget," Maggie called as he headed for the door. "Friday morning."

Dylan gave her one last smile. "Don't worry girl! I'll see you then."

As he left the studio and walked toward the dining hall, the fresh air hit him like a wave of relief. He spotted Aaron, Hannah, and Marcus heading to breakfast and waved at them, ready to retreat to the comfort of his friends.

This week was going to be long—very long.