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Chapter 5
by thenewagewriter
What's next?
Continued!
Back home, he locked the door, double-checked the blinds, and dumped his haul on the bed. The dress went on first, sliding over his jeans with a faint rustle. It was tight across the chest, loose around the waist, and smelled like mothballs and lavender. He wrestled the wig onto his head, strands catching in his mouth, the synthetic fibers itching like a swarm of ants.
The heels came next, and he wobbled upright, clutching the bedframe as his ankles threatened mutiny. He shuffled to the bathroom mirror, the clack of the shoes echoing in the silence.
“Holy shit,” he breathed. He looked… not awful. Ridiculous, yeah—lips too red where he’d smeared the lipstick, cheeks flaming with uneven blush, lashes clumped into spiky clumps from the mascara. But with practice? Maybe passable. He straightened, hands on hips, and tried a smile.
“Hi, I’m Diana,” he said, pitching his voice high. It cracked like a pubescent kid’s, and he groaned, rubbing his face—then cursed as he smeared makeup everywhere. “Diana” stuck, though. Quiet, nervous, the kind of girl who’d slip into a sorority sleepover unnoticed. He’d say she was a transfer student, eager to help, pizza in tow.
The thought of facing Lila like this—of her smiling at “Diana,” maybe even chatting—sent a jolt through him, equal parts dread and exhilaration.
What's next?
The Sorority Trap
Transgender Woman on Sissy Femboy
Danny’s heart stopped, but Lila waved it off. “More the merrier,” she said, grinning, and pointed to a snack table. “Make those pretty.” This is an 5000 word short story about a boy discovering himself and a girl helping him in that journey. Enjoy! Danny was a normal 20 year old boy who wanted to go and meet girls in the sorority including his crush Lila. So he decided to take on this challenge by changing himself into Diana and entering the sorority house. Now this backfired greatly on him and the girls caught him. Some of the girls in the sorority were very pretty for sure but they were also a little more of a ‘man’ than he was.
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Updated on Mar 27, 2025
by thenewagewriter
Created on Mar 27, 2025
by thenewagewriter
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