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Mr. Jacob noticed
by nimt
Chapter 32 in Crossdressing Stories
The coach tilted his head slightly. “And I couldn’t help but notice you were wearing a… violet swimsuit. Not exactly the usual choice.” Glenn’s heart skipped. Please don’t go further. Please. “It looked,” Mr. Jacob continued, “like a women’s bikini bottom.” Glenn’s stomach tur...
1 year ago 248 Words 7 Likes 1,976 Views -
At the detention Room
by nimt
Chapter 31 in Crossdressing Stories
Simon sat in the corner, scribbling in a notebook. Peter, Bruce, Alan, Paul, and Joe were scattered across the room, half-asleep or looking at their phones. At the far end, near the window, sat Mr. Jacob. Not at the desk, but leaning back in a chair, one leg crossed, arms folded...
1 year ago 294 Words 6 Likes 1,945 Views -
Changing to normal clothes
by nimt
Chapter 30 in Crossdressing Stories
The hazing ended as suddenly as it had started, like a cheap prank losing steam. Good. Glenn stood there for a few seconds, just breathing. His hands still trembled slightly as he peeled off the violet bikini bottom. He folded it carefully and tucked it into the Ziploc bag his...
1 year ago 233 Words 5 Likes 1,961 Views -
Confrontation with Mark
by nimt
Chapter 29 in Crossdressing Stories
The class was dismissed, and Glenn moved quickly. He picked up his gym bag from the locker, clutching it tight to his chest. The violet bikini bottom still clung to him, and all he wanted was to change back into his clothes and disappear. He slipped into the changing room, tryin...
1 year ago 365 Words 5 Likes 1,937 Views -
Round 3
by nimt
Chapter 28 in Crossdressing Stories
And Glenn knew… round three was coming. Glenn stood quietly at the edge of the pool, the faint chatter of the class behind him a low buzz. The violet swimsuit still clung tightly to his skin, but now, he barely noticed it. He rolled his shoulders, stretched out his arms, shook...
1 year ago 299 Words 6 Likes 1,952 Views -
Things are shaking up!
by nimt
Chapter 27 in Crossdressing Stories
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!” h...
1 year ago 317 Words 6 Likes 1,949 Views -
Glenn and Simon lost
by nimt
Chapter 26 in Crossdressing Stories
Simon climbed back in for his second turn. Glenn offered him a quick, “Take it easy,” but it didn’t matter. Two strokes in and Simon was flailing again. Lap six. Slow. Lap seven. Slower. By the time he tagged Glenn back in, they had slipped to second-last place. Glenn didn’t...
1 year ago 191 Words 7 Likes 1,952 Views -
Start of class - Laps
by nimt
Chapter 24 in Crossdressing Stories
His legs were tense. His throat dry. He wasn’t sure if anyone had seen. Or if anyone would. Twenty boys gathered around Mr. Jacob, standing on the slick tiles in a loose, restless huddle. Chlorine hung in the air. The water behind them rippled with faint waves from the last cla...
1 year ago 353 Words 5 Likes 2,138 Views -
A close race
by nimt
Chapter 25 in Crossdressing Stories
The whistle blew, and Simon splashed into the pool with all the and coordination of a falling lawn chair. Glenn winced. One lap in, Simon was already winded. His strokes were wide, inefficient, and by the time he reached the other end, he was gasping. He dragged himself u...
1 year ago 156 Words 5 Likes 2,085 Views -
Monday
by nimt
Chapter 23 in Crossdressing Stories
Monday came too fast. Glenn had barely slept the night before, replaying everything in his head—the store, the swimsuit, Jenny’s smirk, the mysterious gift bag. But in the morning, everything was oddly quiet. He came down to find his gym bag already packed and sitting on the ki...
1 year ago 406 Words 12 Likes 2,153 Views -
Going home
by nimt
Chapter 22 in Crossdressing Stories
They got home, and his mother went straight to the kitchen, leaving the bags by the table. Glenn slipped past her, climbed to his room, and shut the door. He didn’t touch the bags. Didn’t ask. Didn’t want to. He didn’t even bring up the swim class again that weekend. His mot...
1 year ago 108 Words 9 Likes 2,059 Views -
Present
by nimt
Chapter 21 in Crossdressing Stories
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...
1 year ago 171 Words 12 Likes 2,306 Views -
We'll take this one.
by nimt
Chapter 20 in Crossdressing Stories
The laughter from the salesladies echoed in Glenn’s ears, but his mother seemed unfazed. She tapped her fingers against the counter, making her final decision. "We’ll take this one," she said, holding up the white thong with red polka dots—the one Glenn had just tried on. Glenn...
1 year ago 218 Words 12 Likes 2,205 Views -
Jenny spotted something
by nimt
Chapter 19 in Crossdressing Stories
Jenny was laughing with a few other sales ladies, while his mother was still browsing. His mother turned as he approached. “Well?” Glenn bit his lip. “…It’s okay, I guess.” Jenny suddenly appeared beside his mother, grinning. She leaned in slightly, her eyes dropping to his cr...
1 year ago 100 Words 12 Likes 2,429 Views -
Trying On
by nimt
Chapter 18 in Crossdressing Stories
Jenny appeared beside him almost instantly, flashing a wide smile. “Oh, don’t worry! He’s special. He is trying on a swimsuit.” The saleslady raised an eyebrow before sighing. “Fine. He can use the corner cubicle.” Glenn barely managed a nod before slipping inside the stall and...
1 year ago 176 Words 11 Likes 2,356 Views -
and Glenn said "No"
by nimt
Chapter 17 in Crossdressing Stories
“…Can I say no?” he tried. His mother smiled sweetly. “Of course.” Relief barely had time to register before she added, “We’ll take both.” Glenn’s stomach twisted. He had walked straight into that one. Jenny giggled and walked over to the rack, plucking out the two swim thong...
1 year ago 202 Words 11 Likes 2,344 Views -
A Swimming Thong
by nimt
Chapter 16 in Crossdressing Stories
Glenn wanted to die. The rack wasn’t filled with swimsuits—it was bikinis. A colorful assortment of bikini tops and bottoms, some in pastel colors, others in bright, playful patterns. His mother smiled at Jenny. “Thank you for your service.” Jenny grinned. “Want to try a top, t...
1 year ago 164 Words 15 Likes 2,382 Views -
Off to the women swimsuit section!
by nimt
Chapter 15 in Crossdressing Stories
Glenn’s heart pounded as he tried to retreat into himself, but his mother wasn’t done. “Not yet,” she said flatly. His stomach dropped. He had been so close to escaping. He desperately hoped the other salesladies wouldn’t come over and make things worse, but luck had never bee...
1 year ago 219 Words 14 Likes 2,394 Views -
It wasn't what he think it is
by nimt
Chapter 14 in Crossdressing Stories
But then Jenny’s eyes lit up with something mischievous. "Oh, there’s just one slight problem." Glenn tensed. "...What?" Jenny hesitated, putting on a sheepish expression. "Well… there’s just one more thing." A sense of pure dread crept over him. "...What?" His voice wavered....
1 year ago 258 Words 12 Likes 2,488 Views -
Glenn's Mom is satisfied
by nimt
Chapter 13 in Crossdressing Stories
Without a moment's hesitation, his mother reached out, grabbing the front of the swimsuit. She gave the pouch a firm tug, but the fabric wouldn’t budge. It was that tight. Jenny smirked. "Oh, that’s perfect," she cooed, tilting her head as she examined him. "You can hardly even...
1 year ago 198 Words 12 Likes 2,520 Views
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