Disable your Ad Blocker! Thanks :)
Chapter 27
by nimt
What's next?
Things are shaking up!
Mr. Jacob paced the poolside, stopwatch in hand, his brow furrowed. He’d been teaching PE for years, and rarely did someone like Glenn—quiet, frail-looking, awkward—surprise him.
That kid moved in the water.
Mr. Jacob raised a hand and blew his whistle.
“Alright, listen up!” he shouted. The chatter died down. “We’re shaking things up for round two and three.”
The students groaned in unison.
“This time, five laps only per round. But here's the catch—only one swimmer per round. One of you does round two, the other does round three. Choose wisely.”
He paused, then added, “And to keep things competitive: the last three swimmers in each round will stay an extra 30 minutes after class.”
That silenced everyone.
Simon looked at Glenn nervously. “You want to go first again?”
Glenn shook his head, still towel-wrapped and breathing deep. “I need a minute. You go.”
Simon didn’t argue. He shuffled to the pool's edge and slid in.
Mr. Jacob blew the whistle.
Simon started strong—relatively. But by the end of the second lap, two boys had already finished all five.
Glenn winced from the bench, watching Simon’s arms flail, his strokes widening, his form falling apart.
By lap three, he was the only one still swimming. The rest of the class stood dry, watching in awkward silence.
Lap four crawled by. Glenn could barely watch.
Simon touched the wall to complete lap five, panting hard and gripping the edge.
Mr. Jacob checked his watch, then called out, “Simon, Peter, Bruce—you’re in for 30 extra minutes after class. Rest up.”
Simon pulled himself out of the pool and sank onto the tile beside Glenn, defeated.
“I tried,” he mumbled.
“I know,” Glenn said quietly.
Mr. Jacob glanced at Glenn from across the pool, then at his clipboard. He wasn’t saying anything—yet—but there was something in his eyes. Curiosity. Maybe even expectation.
What's next?
Disable your Ad Blocker! Thanks :)
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
- Tags
- Hypnosis, Misunderstanding, Crossdress, Halloween, Bet, Dare, Crossdressing, hormones, feminization, sissy, housewife, Stepford, Stepford wife, hucow, Maid, Fetish, Femdom, Thigh-highs, mistaken identity, mind control, manipulation, Accidental, Mr Handy, Vault, Fallout, Magical Crossdressing, Leather, Princess, Secretary, Fantasy, pokemon, Mindcontrol
Updated on Jul 4, 2025
by Mr Nice Guy
Created on Feb 1, 2018
by Dayeandknight
- 5,022 Likes
- 1,632,576 Views
- 855 Favorites
- 545 Bookmarks
- 355 Chapters
- 49 Chapters Deep
- All Comments
- Chapter Comments