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Chapter 16
by
cutiepie183
After dinner excitement
A big night out
Glenn stood in front of his open wardrobe, carefully folding and hanging the new clothes he’d bought earlier. His hands moved methodically—smoothing out the soft fabrics, aligning the skirts on hangers, arranging his lingerie in neat little stacks. It was almost meditative, a way to keep his mind from spiralling, because if he let himself think too much, he’d have to acknowledge what he was doing - Organising a wardrobe full of skirts, dresses, and lingerie that belonged to him.His old clothes were gone. This was all he had now.
The thought sent a shiver down his spine. He didn’t know if it was fear or something else. A sudden knock at the door broke his focus. Before he could even react, the door swung open, and Olivia, Mia, Sophie, and a few other girls burst in.
“There’s our girl!” Olivia grinned, throwing herself onto Glenn’s bed.
Glenn stiffened. “I—”
“Oh my God, look at this.” Sophie peeked over his shoulder into the wardrobe. “You actually organized everything already? You’re such a natural sissy.”
Mia giggled. “Of course he is! Or should I say she?”
Glenn flushed. “I—um—”
“Anyway!” Olivia clapped her hands together. “We were thinking—since our new little bestie has such fabulous new clothes, it’s only fair we take her out for a proper test run.”
Glenn blinked. “Test run?”
“We’re going clubbing, baby!” Mia beamed. “And you’re coming with us.”
Glenn took a step back. “Oh, I—I don’t think—”
“Oh, come on,” Sophie cooed, looping her arm around his. “You can’t waste a perfectly good makeover by sitting in your room all night.”
Glenn’s mind raced. Going out dressed like this? In public? Where everyone could see him?
His hesitation only seemed to encourage them.
“Don’t worry, we’ll take care of everything,” Olivia promised. “You’ll be the hottest girl at the club by the time we’re done with you.”
Before Glenn could protest, he was being pulled toward the bed, the girls already chattering about what he should wear.
The next hour was a blur of giggles, fabric, and excitement as the girls worked on transforming Glenn.
First came the outfit. “Something sexy, but not too over-the-top,” Olivia mused, rummaging through the wardrobe. “Ah-ha! This is perfect.”
She held up a sleek, form-fitting black mini dress with thin spaghetti straps. It was short—way shorter than anything Glenn had ever worn before. His face burned.
“I—I don’t think—”
“Nonsense,” Sophie said, shoving it into his arms. “Go try it on.”
Glenn swallowed hard but obeyed, stepping into the bathroom and slipping into the dress. The silky fabric clung to his body, accentuating every curve he didn’t know he had. When he finally stepped out, the girls lost it.
“Holy shit.”
“Oh my God, Glenn.”
“You’re actually hot.”
He shifted uncomfortably as their gazes raked over him.
Then came the shoes—a pair of black strappy heels that Olivia insisted “completed the look.” Walking in them was a struggle at first, but with some practice (and a lot of teasing), Glenn managed to find his balance.
Finally, the makeup.
Mia took charge, sitting him down and working her magic. A smoky eye, winged liner, soft pink lips—by the time she was finished, Glenn barely recognized himself.
His heart pounded as he stared at his reflection.
Was this really him?
The girls gathered behind him, admiring their work.
“You are gorgeous,” Sophie breathed.
“Ready for your big night out, princess?” Olivia smirked.
Glenn swallowed. He wasn’t sure.
But it was too late to back out now.
As they made their way down the dorm hall, laughter and excitement buzzing between them, they almost walked straight past Aaron—who had been leaning casually against the wall near their door.
“Damn,” he said, pushing off the wall. His gaze flickered over Glenn, a slow smirk spreading across his face. “Didn’t think you’d actually go through with it.”
Glenn stiffened. “I—”
“We’re taking her out for her first night on the town,” Olivia announced proudly, throwing an arm around Glenn’s shoulders.
Aaron raised an eyebrow. “Her, huh?”
Glenn’s face burned, but he didn’t correct her.
Aaron’s smirk deepened. “Sounds fun. Guess I’ll tag along.”
Olivia scoffed. “This is a girls’ night.”
Aaron shrugged. “I don’t mind being the exception.”
The girls exchanged glances. Then Mia smirked. “Actually… it could be fun having a chaperone.”
Glenn’s stomach twisted. He wasn’t sure if he wanted Aaron to come or if that made things worse.
But once again, he didn’t get a choice.
With Aaron joining the group, they headed out, excitement bubbling around them.
And as they stepped out into the night, Glenn had a sinking feeling that this was going to be a night he’d never forget.
Clubbing
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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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