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Chapter 14
by
cutiepie183
Where to next?
Home
Glenn’s heart pounded as he pushed open the door to his dorm room. Maybe, just maybe, he could shove the bags under his bed before—
“Oh. You’re back.”
Glenn froze. His roommate, Aaron, was sitting on his bed, arms crossed, a knowing smirk on his face.
Then Glenn noticed the boxes.
His dresser drawers were empty. His side of the closet was bare. All his old clothes—his jeans, his t-shirts, even his sneakers—were packed away in cardboard boxes stacked neatly by the door.
“W-What did you do?” Glenn stammered.
Aaron shrugged. “Figured you wouldn’t be needing them anymore.”
Glenn’s stomach twisted. “You can’t just throw out my stuff!”
“I didn’t. I’m donating it. Making room for all your new clothes.” Aaron’s smirk widened as his eyes flicked to the shopping bags in Glenn’s hands. “The girls have been sending lots of pics from your little shopping spree. I particularly like that little black dress with the thigh slit you tried on.”
Glenn swallowed hard. He had no idea his little shopping exploration had been made so public but there was nothing he could do now.
Glenn’s grip tightened on the shopping bags, his heart hammering in his chest. His eyes darted between Aaron, the neatly packed boxes, and the empty space where his old wardrobe used to be.
“This… this isn’t funny,” Glenn said, his voice shaky.
Aaron leaned back on his bed, arms behind his head. “Didn’t say it was.”
Glenn’s mind raced. He could unpack the boxes, reclaim his old clothes, and pretend today had never happened. But that smirk on Aaron’s face told him something—his roommate wasn’t just messing with him.
He was testing him.
Glenn looked down at the bags, at the pastel colors and delicate fabrics peeking out. His face burned.
“…Where did you even plan on donating them?” he asked quietly.
Aaron raised an eyebrow, then let out a short laugh. “What’s it matter to you? Not like you’ll be needing them anymore sissy.”
Glenn swallowed hard. “I—” He hesitated, then let out a breath. “Don’t call me that.”
Aaron studied him for a long moment, then shrugged. “Isn’t that what they call little losers like you who wear pretty dresses and shit but still pretend to be boys.”
Glenn didn’t argue. He couldn’t.
Instead, he crossed the room, setting his shopping bags down on his bed. His body moved on autopilot as he pulled out the first piece of clothing—a simple pink sweater—and ran his fingers over the soft knit.
Aaron watched him, but didn’t say a word.
Finally, Glenn turned to face him. “…You’re really not giving my stuff back, are you?”
Aaron smirked. “Nope.”
Glenn let out a defeated sigh and sat on the edge of his bed. “Guess I really don’t have anything else to wear.”
Aaron’s smirk deepened. “Guess not.”
Silence stretched between them.
Then, finally, Aaron stood up, stretching lazily. “Well, I’m gonna go grab dinner. You coming?”
Glenn hesitated. If he went, he’d have to walk through the dorms, the cafeteria, maybe even run into some of the guys from swim class dressed like this.
His fingers curled around the fabric of his dress.
“…Yeah,” he said quietly. “I’ll come.”
Aaron glanced at him, as if sizing him up one last time, then smiled “Good girl.”
As Aaron grabbed his keys and walked out the door, Glenn stood up, took a deep breath, and followed.
There really was no going back now.
Dinner time
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Crossdressing Stories
A collection of separate stories that all involve guys ending up in dresses
A collection of separate stories that all involve guys ending up in a dresses
Updated on Feb 22, 2026
by Dayeandknight
Created on Feb 1, 2018
by Dayeandknight
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