Greg stood in the center of Caroline's bedroom, drowning in a cascade of emerald satin that strained across his broad shoulders. The prom dress had been designed for someone half his size—the zipper strained to close, constraining his breathing even more than the corset. The long blonde wig tickled his bare collarbones, synthetic strands catching the lamplight as he trembled.
Caroline circled him slowly, her green eyes tracing the way the satin pulled tight across his chest. "Look at you," she murmured. "Six feet of pure muscle, drowning in satin and dreams."
Natalie leaned against the dresser, her arms crossed, a thin smile playing at her lips. "The heels would've been a nice touch. Size thirteen?"
Amanda hovered near the doorway, her hazel eyes wide, one hand pressed to her mouth. She was trying not to laugh, but her shoulders shook with the effort.
Greg's face burned. The corset pressed against his ribs with every breath, the satin panties damp and sticky beneath the heavy dress. He could feel his cock stirring again, pressing against the fabric, and he tried to shift his weight to hide it.
Caroline noticed.
Her laughter softened. Her head tilted. She took a step closer, then another, her eyes fixed on the tent forming in the draped satin where his hips met the dress's waistline.
"No way," she breathed.
Greg's throat clicked. He couldn't form words. The wig shifted as he shook his head, a desperate, wordless denial.
Amy caught his eye in the mirror behind Caroline. She was sitting on the edge of the bed, legs crossed, that knowing smile spreading across her face. She raised her wine glass and took a slow sip, never breaking eye contact with him.
Caroline's hand slid up his thigh, beneath the hem of the dress. Her fingers found the damp satin of his panties and paused there. She gave a little squeeze.
"Oh," she breathed. "He's really into this."
The room went quiet. Amanda's hand dropped from her mouth. Natalie set down her wine glass with a deliberate click. Greg felt his humiliation crystallize into something electric—shame and arousal fusing into a single, unbearable need that pulsed through his body like a second heartbeat.
"Holy shit," Amanda whispered. "Greg, you're—you're actually hard."
Greg's jaw clenched. His cock throbbed against Caroline's fingers through the satin, and he couldn't stop it, couldn't hide it, couldn't deny what his body was screaming.
Caroline didn't pull her hand away. She held his gaze, her thumb tracing a slow circle against the damp fabric. "Does this turn you on, Gina? Being dressed up like a pretty girl while we all watch?"
The name hit him like a current. Gina. He felt something crack open inside his chest.
"Answer her," Amy said softly. Not unkindly. But firmly.
Greg's voice came out thin, cracked. "Yes."
Caroline's grin widened. She turned to look at Amy, who simply shrugged and took another sip of her wine, her dark eyes gleaming over the rim of the glass.
Natalie pushed off the dresser and crossed to the large oak vanity against the far wall. She pulled open the bottom drawer with a screech of old wood and started rifling through it. "Caroline, where's that—ah." She pulled out a black silicone dildo attached to a leather harness, holding it up like a trophy. A huge smile spread across her face.
Caroline's fingers curled around the damp satin of his panties and pulled them aside. The emerald dress bunched at his waist as she lifted the hem, exposing his cock straining against the pink satin, the tip already dark with a wet spot spreading through the fabric. She wrapped her hand around him through the material, a firm possessive grip.
"Look at this," Caroline said, her voice carrying through the room. "Look at the big, strong man, harder than he's ever been in his life, because his friends dressed him up like a prom queen."
Natalie stepped closer, the harness dangling from her fingers, her brown eyes fixed on the tent in the pink satin. "You have got to be kidding me. He's actually throbbing."
Greg's breath came in short, shallow gasps. The corset pressed against his lungs, the wig tickled his shoulders, and Caroline's hand held him through the damp fabric like she owned him. He couldn't look at anyone. His eyes fixed on a crack in the ceiling plaster.
"How long have you been hiding this, Greg?" Amanda's voice was soft, hesitant, from somewhere near the doorway. "The panties. The corset. The—" she gestured vaguely at his trapped cock. "All of it."
"Long enough," Amy said from the bed. She hadn't moved. She was watching him with that same knowing smile, legs crossed, wine glass balanced on her knee. "He came to me with it sophomore year. Shaking. Thought I'd break up with him."
"And you didn't?" Amanda asked.
Amy laughed, a warm, genuine sound. "I made him put on my panties that night. He came in thirty seconds."
The room erupted. Caroline cackled, her grip tightening reflexively. Natalie let out a low whistle. Amanda's face went scarlet, but she was smiling now, a nervous, curious smile.
Greg's cock jerked in Caroline's palm. He couldn't help it. The words hit him like electricity—Amy telling them, the room knowing, the shame and the relief and the unbearable heat coiling in his gut.
"Oh my god," Amanda breathed. "He just—did you feel that?"
Caroline's grin was wolfish. "Yeah. I felt it." She squeezed once, firm, then released him and let the emerald satin fall back into place. "Alright, Gina. Let's see the full package. Twirl for us."
Greg's knees went weak. The name again. Gina. It landed in his chest like a key turning a lock he didn't know existed.
"Go on," Amy said softly. "Show them what you've got."
He lifted his arms. The satin rustled as he turned, the heavy skirt flaring around his legs. The wig spun with him, synthetic blonde strands catching the lamplight. He completed the rotation and stopped, facing them, his face burning, his cock straining against the damp panties beneath the dress.
"Beautiful," Caroline said, and there was something genuine in her voice. "You make an ugly woman, but you commit to it."
Natalie was already strapping on the harness. She adjusted the black silicone dildo with a practiced hand, testing the fit, the weight of it. "Alright. Let's see how she handles a real woman's touch."
She crossed the room slowly, barefoot on the hardwood, the dildo bobbing with each step. Greg's throat went dry. She stopped in front of him, close enough that he could smell her perfume—something floral, light, at odds with the black silicone between her legs.
"Hello, Gina," she said, and her hand came up to cup his jaw. Her thumb traced his lower lip. "You're very pretty for a sissy."
Greg's breath stuttered. His hands hung at his sides, trembling.
Natalie's other hand slid down his chest, over the strained satin of the dress, across his stomach, until her fingers found the tent beneath the fabric. She pressed against him, feeling the heat of his cock through the layers, and leaned in to whisper in his ear.
"Does this make you feel like a real girl?"
He nodded. A tiny, desperate motion.
"Good," she said. "Because we're going to make you feel like one."
Amanda took a step forward, then another. Her hazel eyes were wide, fixed on Greg's face, on the full redness of his shamed cheeks. She didn't look disgusted. She looked fascinated. Hungry. Like she was seeing something she'd never known she wanted to look at.