Crestwood Academy for Young Ladies - Forced Fem Fantasy

Chapter Thirty-Three: Inspired by the 50s

Friday morning arrived, and Dylan pulled himself out of bed, stretching before getting ready for the day. The past two days had been a blur of classes and practice sessions. In some ways, everything was going well—he was nailing the talent show routine, even if every hip sway and arm wave made him cringe on the inside. Still, no one could tell it bothered him. He was good at pretending now, a necessary skill in this strange new world of femininity.

Today, though, was a different kind of test. Today, he had to meet Maggie, his student designer, for the modeling assignment that Beaumont had forced on him. He wasn't looking forward to it, but, as usual, he'd act like he was enjoying it.

Dylan got dressed, pulling on his school uniform, and made his way down to meet Kyle, Sophie, and Hannah. "You ready?" Sophie asked, smiling at him.

"I guess so!" Dylan replied with mock enthusiasm, his voice bright.

The four of them headed to the Garment and Apparel classroom. Once there, Sophie and Hannah quickly found out they were in luck. Two models had dropped out last minute, so each of them was paired up with a student designer. Dylan watched as Kyle walked off to meet his designer, leaving him standing awkwardly for a moment until a tall girl with long, silky blonde hair, pulled into a tight ponytail, approached.

"Diana, right?" Maggie greeted with a smile, exuding a confidence that reminded Dylan of a classic popular mean girl from high school. Despite her intimidating aura, her friendliness surprised him.

"That's me!" Dylan replied, his voice cheerful as he slipped into his now well-practiced girly persona. "I'm guessing you're Maggie! So excited to see what you've got planned!"

Maggie beamed, clearly pleased with his enthusiasm. "Oh my god! I'm so glad you're my model. You have literally the perfect body for my design. Thanks again for volunteering."

Dylan internally winced but kept up the act, smiling as if he were genuinely thrilled. "Girl, of course! I mean, who wouldn't want to model in a fashion show?"

Maggie led him over to her workstation, where a drawing of her design lay spread out. "The theme for this show is 'Inspired by the 50s,'" she explained, her tone filled with pride. "I've gone for a look that blends the traditional housewife aesthetic with women's liberation. It's the perfect mix of vintage and modern."

Dylan nodded along, trying to look fascinated. "Woah! That sounds amazing!"

Maggie smiled and pointed to the drawing. The outfit consisted of a white pleated skirt that sat neatly around the knees, layers of petticoat peeking out beneath. The top, a striking red blouse that had a blazer-like structure, complete with large frilly shoulders and a deep V-neckline that immediately caught the eye. A white belt cinched the waist, completing the look.

"What do you think?" Maggie asked, glancing at him for a reaction.

Dylan's heart sank at the sight of the ultra-feminine outfit, but he plastered on his best smile. "Oh my god, it's gorgeous! I love the way the shoulders pop. And that skirt! So... elegant!"

Maggie beamed. "Right? I thought it would complement your frame perfectly."

No it totally will! I can definitely see that," Dylan replied, his voice laced with forced excitement. "Ugh, this is going to be so cute!"

Maggie continued, clearly enjoying his apparent enthusiasm. "We'll take your measurements today, and I'll tailor the dress to fit you exactly. We'll do the first fitting on Sunday or Monday, depending on your schedule."

Dylan nodded, remembering the conversation from last night. "I can't do Sunday. I'm getting manicures with some of the other girls for the talent show." He rolled his eyes playfully, like it was a big deal. "You know how it is, right?"

Maggie grinned. "Of course! Well, we can do Monday then. No rush. Also, don't worry about the nails clashing with the look, you'll be wearing gloves so it doesn't even matter."

Dylan let out a mock sigh of relief. "Oh my god! I hadn't even thought of that."

Maggie laughed softly and looked him over again. "I'm actually so excited for this, Diana. You're going to look stunning."

Dylan smiled, channeling as much energy as he could into his response. "No! It's your dress that's going to look stunning! I'll just be having fun showing it off."

As much as Dylan dreaded the upcoming runway show, he was quickly becoming an expert at hiding his true feelings. The key, he figured, was to act like everything was the best thing ever.

After they finished the measurements, Dylan rejoined Sophie, Hannah, and Kyle, who were also wrapping up with their designers. Sophie practically bounced over, excitement in her eyes. "How did it go?"

Dylan smirked, dropping the bubbly act. "Oh, it was just a dream come true," he said, his voice dripping with sarcasm. "Maggie's design is just incredible. A real masterpiece of retro glamour. I can't wait to wear it."

Hannah grinned, missing the sarcasm. "Isn't this theme the cutest? I love how retro!"

Dylan shot her a deadpan look. "Yeah, 'cute' is definitely the word I was going for."

Kyle, overhearing the exchange, gave Dylan a knowing smirk. They were both in the same boat—playing along just to get through it.

With the measurements done, they all headed to the dining hall for breakfast. Sophie chattered on excitedly about her designer's ideas, while Hannah enthusiastically joined in with her thoughts on the 50s theme. Kyle and Dylan stayed mostly quiet, sharing the occasional sarcastic smile as they endured the conversation.

One thing was certain—Dylan was becoming very good at pretending.