Chapter 8
by
nimt
Who was it
Jenny, sales assistant
A young woman, probably in her early thirties, approached them with a curious smile. She had a store badge pinned to her chest.
"Hi, my name is Jennifer Sinclair, you may call me Jennifer or Jenny for short. I prefer Jenny, that's what everyone calls me" she said cheerfully. "May I help you with anything?"
His mother didn’t hesitate. "Ah, yes! We have a little problem here." She turned to Jenny and, without warning, tugged at the fabric around Glenn’s swimsuit again.
Jenny’s eyes dropped down to inspect.
Before Glenn could step back, his mother slipped three fingers into the leg opening, feeling around as if she were testing the material. Her fingers accidentally brushed against his balls.
Glenn squirmed, his body jerking slightly from the unexpected contact.
Jenny chuckled. "Oh, I see. This is too large for our little gentleman here," she said, nodding sagely.
Glenn’s soul nearly left his body.
Jenny turned to his mother. "Would you like me to find something smaller? We might have a better size in another section."
His mother clapped her hands together. "That would be a big help!"
Then she shot Glenn a look.
"Go on. Thank Jenny for her help."
Glenn was barely holding himself together. He swallowed hard and muttered, "Thank you, Jenny."
Jenny giggled. "You're welcome! Just wait right here, I’ll find something perfect for you."
Glenn stood awkwardly in the corner, trying not to attract any more attention to himself.
What's next?
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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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