Chapter 21
by
nimt
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Present
Just as they were about to leave the store, Jenny reached under the counter with a mischievous smile and handed Glenn’s mother a small, glossy paper bag—distinct from the one carrying the swimsuit.
“A little gift bag for our brave little guy,” she said cheerfully, giving Glenn a wink. “Don’t open it here. It’s a surprise.”
Glenn froze.
His mother raised an eyebrow, curious, but tucked the bag into her purse without a word. “Well, that’s very thoughtful, Jenny. Thanks again.”
Jenny grinned. “Enjoy it! I’m sure it’ll make things… interesting.”
Glenn didn’t dare ask what was inside. He was curious, but he didn’t want to know.
The ride home was quiet.
Neither of them spoke. His mother didn’t gloat, didn’t tease. She just drove, humming faintly to the radio while Glenn stared out the window, his thoughts twisting into knots.
He felt wrung out. Not just from embarrassment, but from how little control he had. And that gift bag… whatever it was, it felt like a ticking time bomb.
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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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