Lady Harmonia's Academy for Distinguished Young Women

Chapter 19: Lolita x Princess x D&D

Tyler followed Izzy through the pristine halls of Rockefeller Center, his eyes darting nervously at the opulent shops that seemed a world away from what he was used to. Everything around him felt too polished, too perfect, and it made him feel like he didn't belong. He had grown up in Brooklyn, where the streets were gritty, and the fashion was more about what you could find at the local thrift store than what was displayed in designer windows. Here, every shop looked like it had been plucked straight from a fashion magazine, and Tyler couldn't shake the feeling that he was out of his depth.

Izzy, on the other hand, was completely in her element, her eyes practically glowing with excitement as she dragged Tyler from one rack of clothes to the next. "You're going to look amazing in this," she said, holding up a cropped leather jacket and a pair of high-waisted jeans. "Trust me, Thalia, we're going to turn some heads."

Tyler tried to smile, but the discomfort gnawing at him made it hard to get into the spirit. He didn't know how to explain it, but something about being here, in this place, just felt off. The more Izzy gushed about the clothes, the more he wanted to retreat into himself, away from all this extravagance.

Izzy paused mid-sentence, looking up from the clothes she was inspecting. She frowned slightly, her sharp eyes catching onto Tyler's mood in an instant. She stopped what she was doing and took a step closer to him, lowering her voice so only he could hear.

"Hey," she said gently, her hand resting on his arm. "I can see this isn't your vibe, and that's okay. Forget all this," she gestured to the boutique around them, "and all the stuck-up people who shop here. You and me? We're going to hit up the best spots. I know all the good ones. Trust me, it'll be fun. Who cares what anyone else thinks?"

Tyler blinked at her, surprised by her shift in tone. Izzy was always so bubbly and full of energy that he hadn't expected her to notice his discomfort. But the fact that she did... it made something inside him relax a little.

"Yeah?" he said, raising an eyebrow. "Just have fun, fuck it all?"

Izzy grinned, giving his arm a playful squeeze. "Exactly! Fuck it all! Let's just go have a blast. You know how uptight people are in places like this. Let's mess with them a little. You'll look killer, they'll stare, and we'll have the time of our lives."

Tyler chuckled despite himself. That... he could get down with. The idea of walking through these fancy stores, wearing something that made everyone uncomfortable, made the whole situation feel a little more bearable. He could picture it now—him, with his bold makeup, decked out in the most over-the-top outfits, watching the prim and proper customers sneer at him. It was enough to spark a bit of rebellious excitement in his gut.

"Alright, you've convinced me," he said, his smirk returning. "Let's go have some fun."

Izzy's grin widened, and without missing a beat, she grabbed his hand and led him out of the current boutique, heading for her favorite spots. The first stop was a quirky little shop tucked away in a corner, far less polished than the other high-end stores. The clothes here had an edge, a certain unpredictability that suited Tyler more than the pristine designer wear from before.

They spent the next hour or so darting in and out of different stores, trying on everything from leather jackets to platform boots to outrageous, high-fashion gowns. And every time Tyler caught someone staring at him—an older customer giving him a disapproving glance or a sales associate eyeing him up and down—he couldn't help but grin. It was like he could feel the tension in the room every time he strutted out in a new outfit, and instead of making him uncomfortable, it made him feel powerful.

At one point, he walked out in a black satin dress that hugged his new curves, with thigh-high boots and silver accessories, and he could almost hear the sharp intake of breath from the prim woman standing nearby. Tyler winked at her, strutting past with exaggerated confidence, and the look of horror on her face was enough to send both him and Izzy into a fit of laughter.