Crestwood Academy for Young Ladies - Forced Fem Fantasy

Chapter Thirty-Eight: The Debutante Ball

Dylan stood just inside the ballroom, nerves twisting in his stomach as he scanned the elegant scene before him. The grand space was breathtaking, bathed in soft golden light from the chandeliers overhead, while soft classical music played in the background. Girls from Crestwood Academy floated across the room, their skirts swishing and gowns shimmering in shades of pastels and deep, luxurious tones. The students moved in small groups, laughing and chatting as they mingled.

Dylan's gown—a yellow skirt which puffed at the waist and sleeves and cinched at the bodice. He tugged at the waistline, trying to ignore the tightness and the subtle itch of the fabric against his skin. He felt out of place, but there was no turning back now.

Marcus, who stood beside him in a pastel green gown that flowed with every slight movement, looked positively thrilled. "This really isn't so bad" Marcus whispered, glancing at the room with wide eyes. "I feel like we're royalty."

Dylan smiled weakly. Marcus was loving every second of this charade. "Yeah... sure," Dylan echoed, though it felt more like a nightmare to him. His feet were already aching from the unfamiliar heels, and the idea of making small talk with strangers only added to his discomfort.

Aaron and Kyle weren't faring much better. Aaron, looked like he was barely holding it together. His lilac gown and big bow in his hair suited him, but the rigid posture and clenched jaw made it clear how uncomfortable he was. Kyle, stood close by, managing to keep his composure, though Dylan could tell he was just as nervous.

The sound of laughter drew Dylan's attention as a group of boys from the local boys' private school walked into the ballroom. Dressed in sharp tuxedos, they looked every bit the part of charming escorts, but what Dylan couldn't shake was the knowledge that these boys had no idea he and his friends weren't actually girls.

As the boys began to disperse into the crowd, mingling with the Crestwood students, Dylan felt his pulse quicken. He could feel the eyes of the teachers on him from across the room—Ms. Abbot, in particular, was watching them closely, clipboard in hand, grading everything from their posture to their conversation skills.

Dylan took a deep breath. He had to get through this without slipping up.

Just as he tried to inch back into the comfort of his group, one of the boys approached. He was tall, with neatly styled dark hair and a confident smile. Dylan's stomach flipped as the boy made eye contact and extended a hand.

"Hi there," the boy said warmly. "Mind if I join you?"

Dylan hesitated, glancing briefly at Marcus before stepping forward. "Not at all." His voice came out a bit higher than usual, a nervous attempt at staying in character. "I'm Diana."

The boy smiled, clearly not noticing anything out of place. "It is very nice to meet you, Diana. I'm Matt Schaffer."

Dylan forced a smile, nodding politely. "It is nice to meet you too." His heart was racing, but he couldn't afford to mess this up. "Are you from the local school?"

Matt nodded. "Yeah, I'm one of the volunteers. My school does this every year, but this is the first time I've been invited." He gestured to the room. "It's pretty fancy, huh?"

Dylan glanced around, trying to come up with a response that wouldn't betray how uncomfortable he felt. "Yes, it is. Crestwood really knows how to put on an event."

Marcus, eager to keep the conversation going, jumped in with a bright smile. "I'm Maya, by the way," he said, offering his hand. "What do you think of our dresses?"

Matt's gaze shifted, and he smiled politely. "You both look great. Very elegant."

Dylan nodded, trying to play along. "Thank you. It's... not something we usually wear." Understatement of the century, he thought to himself, but kept the smile on his face.