Betty Pearl's Sissy Stories 20.1
Menu => Active Sissy Stories => Topic started by: Baby Bobby on July 17, 2026, 04:59:56 PM
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Brian sat nervously on the single, lonely chair situated outside the school Principal's office.
His mouth was dry and he kept wiping his sweaty palms on the legs of his shorts. Just inside the next room, he could hear one side of a conversation; the strict, firm voice of Mrs. Sterne, who's name adorned the opaque glass window on the door next to him. Brian couldn't hear the other student's voice, but it was obvious he was being scolded just before his imminent spanking. Brian could imagine all too well what he must be thinking—soon the boy would have his pants pulled down and taken over her lap. Sure enough, there was a pause in her scolding and Brian's eyes widened as he heard the first resounding swat of the paddle on the student's defenseless bottom. Almost immediately, the boy's wails could be heard as the school's disciplinarian meted out his well-deserved punishment.
Brian squirmed in his seat, knowing all too well that he was going to be next.
He tried frantically to come up with some excuse that would allow him to get off with a mere scolding but it was hard to concentrate as the harsh swats continued to rain down on the poor boy's bare bottom. He was really crying now, and Brian could imagine him kicking and futilely struggling to escape.
Brian tried to think about what had brought about his recent misfortune. In fact, it was Melissa, the hottest cheerleader at his school that had chosen to bully him again. He had had a number of run ins with her, which often resulted in her humiliating him in some way. She was much taller than Brian and she liked to tease him incessantly whenever they crossed paths. 'Sissy' was her most common epithet for him and he studiously avoided the busty teen when at all possible.
Today it was not to be. Melissa had cornered him in the hallway, along with a few of her stunning cheerleader friends. They had pushed and teased Brian until Melissa pulled the fire alarm, which, minutes later, resulted in the school doing an unnecessary evacuation. Later, when the school authorities had investigated it, she had blamed it on Brian and her friends had backed up her claim.
So now, the poor sissy was sitting on a hard wooden chair outside Mrs. Sterne's office, about to get the spanking of his lifetime.
And his troubles didn't end there, either. Somehow, in all the day's excitement, he'd managed to wet the pull-up his mom insisted he wear under his clothes to protect against accidents. The soggy cloth clung stubbornly to his cheeks and squished warmly between his legs. And while he'd been able to keep his humiliating underwear a secret so far, all that was about to change.
At last, the spanking inside ended, and Brian gulped in fear. Suddenly, the office door opened abruptly and Mrs. Sterne led the crying boy out by his arm. He was rubbing the seat of his pants with one hand and wiping away the tears on his wet face with the other.
“Let that be a lesson to you, the next time you think about pulling a girl's skirt up,” she told him.
He scampered off down the hall, deeply ashamed and wanting badly just to get away.
Turning to face Brian, who was cowering in his seat, she wagged her finger at him accusatorily.
“And what is your name, young man?” she demanded, in a stern tone of voice that could cut through hardened steel.
“B-Brian, M-Ma'am,” he stammered nervously.
“Brian what?” she snapped.
The poor frightened boy felt a warm stream of pee escape into his wet pull-up as he swallowed hard.
“B-B-Brian K-Kimble,” he bleated out.
“Well, Brian Kimble--today, you're going to be taking a trip over my lap,” she told him as she reached down and snatched his wrist, hauling him to his feet and leading him inside her office.
“Wha-wait!” he cried, “I-I didn't do it!”
“Brian,” she stated, completely ignoring his remark, “you're going to get a good, hard spanking and that will teach you not to play with fire alarms at this school,” she said tersely as she led him over to an armless chair.
Brian quaked with fear as he laid eyes on the long wooden paddle with air holes, laying on her desk. It had obviously seen a lot of use, and the varnish was mostly worn off from its surface.
“But I didn't do it!!” he squealed desperately as she took a seat and began unsnapping the catch on his shorts, “M-Melissa did it!”
He hoped frantically that she would believe him but it was not to be.
Tugging his shorts down his legs, Mrs. Sterne stopped in shock as she discovered Brian's embarrassing pull-ups. The ones he was wearing today were a cute pastel baby-blue, with playful designs of bunnies and kittens across the front. His face went beet red as he tried to look away, tears of shame brimming in his eyes.
Momentarily at a loss for words, Mrs. Sterne shook her head as she looked up into his blushing face.
“Well, well, well,” she said slowly, “I'll bet you weren't expecting anyone to see your pretty pull-ups when your mommy dressed you this morning.”
Brian's knees went weak and he felt somewhat faint. The crimson color of his cheeks went to his neck, and all the way down to his chest.
“Maybe you should have thought of that when you were causing your mischief in B hall,” she scolded him as she hooked her fingers inside the elastic waistband of his pull-up. That's when she discovered he'd soaked his 'protection', but she just shook her head again in disapproval as she snaked them down his trembling legs.