Chapter 3
by
nimt
What's next?
He shared his problem with his mother
It was the start of new semester, Glenn's mother had already bought him a pair of trunks without asking his opinion — some generic, loose-fitting thing from a discount store. When he tried them on, it was clear they weren’t right. The fit was awkward, baggy in the front, and loose around the legs. It made him feel even smaller, even more ridiculous.
That evening, he worked up the nerve to talk to his mother about it. She was sitting on the couch, scrolling through her phone, one leg tucked under the other.
"Mom... the swim trunks don’t fit properly," he said carefully, keeping his tone neutral.
She didn’t even glance up. "What’s wrong with them?"
"They’re too loose. The pouch is too big, and the sides don’t hold anything in place," he admitted, already regretting bringing it up.
His mother let out a sharp exhale through her nose, still focused on her phone. "Glenn, I bought the size you always wear."
"I know, but they don’t fit right. It feels like they weren’t made for—" He hesitated.
"For what?" she asked flatly, finally looking at him.
Glenn shifted uncomfortably. "For someone... my size."
His mother stared at him for a moment, then snorted. "Oh, Glenn, come on. You’re acting like you have something so enormous down there that regular swim trunks just can’t contain it."
Glenn felt his face burn. "That’s not what I meant."
She sighed dramatically and put her phone down. "Fine. Go put them on and let me see."
Glenn hesitated. "Right now?"
"Yes, right now, unless you want to keep whining about it all night."
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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