With his mommy holding his hand like he was still a child, Brian shuffled slowly into the classroom where their parent-teacher conference was being held. The fourteen year-old youth was wearing a striped t-shirt, shorts, and sneakers. Unfortunately, the meager cut of his shorts did little to hide the big, bulging diaper he was wearing underneath and the shiny yellow plastic panties peeking out from above the waistband. In addition, the thin fabric did little to hide the nursery print characters of the colorful waterproof panties protecting his diaper.
They sat down in chairs before his teacher’s desk, Miss Crow, who greeted his mother politely. Brian bit his lip in angst and looked the other way as his teacher seemed to stare down at his bulky hips. Having this pretty woman see him in his sissyish diapers like this was mortifying for the shy, timid boy.
“Miss Crow—” Brian’s mom began.
“--Oh—you can call me Anna,” his teacher corrected her.
“Anna—firstly…thank you for giving Brian the spanking he earned yesterday—that is exactly why I enrolled him in this school. I feel it’s very important that he gets the same kind of discipline he receives at home.”
“Not a problem,” she replied, “We have very simple rules here--when a boy wets his pants in class, he can expect to take a trip over my lap and a session with the paddle.”
Brian cringed uncomfortably in his seat.
His bottom was still sore and aching from the twin spankings he’d received—first, at the hand of his drop-dead gorgeous teacher, and then again when he’d gotten home and been forced to deliver the hand-written note she’d given him for his mommy.
“I also find that the added humiliation of getting his bottom paddled in front of all his classmates makes for a memorable lesson,” Anna added.
Brian’s mother smiled in agreement, even as he blushed a deep red. He knew the humiliation would be seared in his memory forever of the other kids giggling at his punishment.
“After some consideration, and as a result of yesterday’s incident, I’ve decided to take the precaution of putting Brian into diapers and plastic panties during the day as well,” his mother continued, as she gently patted his bulky shorts, “It will probably be a little embarrassing for him, but I figure it will also motivate him to try harder to stay dry.”
Anna nodded, “Tell me,’ she asked, “Is he also a bedwetter at home?”’
“I’m afraid so. He wears diapers to bed every night and it’s a rare morning to find he hasn’t soaked them.”
Anna looked at Brian closely as if expecting as much and the subject of their conversation slouched lower in his seat as his cheeks burned with shame.
“It seems some little boys just never outgrow their pampers,” she added sagely, as she smiled at her pupil.
“So, I brought a bag of his diapering supplies and I was wondering if you would be so kind as to change him during the day if he needs it,” his mom asked.
“I’d be happy to,” she replied as he gazed at the red-faced boy, “Brian—from now on, I want you to come to me before lunch and every recess so I can check your diapers—do you understand me?”
The boy nodded silently but stared at the ground praying it would swallow him up.
“Brian—when an adult asks you a question—you are to answer them,” his mom scolded him sternly.
“Yes, Ma’am,” he bleated.
“I think you and I are going to become much better acquainted,” Anna smiled with a smug, superior tone.
“And would you like him disciplined if I find he’s wet himself?” she asked his mommy.
“Yes—I may be willing to put up with his bedwetting, but I won’t tolerate him having accidents during the day. Please be sure to spank him and then change his wet diapers.”
Anna nodded in acknowledgement.
“You know…I have something here that may interest you. We don’t make all the boys wear these,” she said opening her desk drawer, “but we strongly suggest them for the more sissy types, like Brian here.”
The diapered youth was deeply ashamed to be called a sissy but of course, he said nothing.
Reaching into her desk, Anna pulled out a strange pink plastic contraption that she held forth for Brian’s mom to see.
“If you’ve never seen this before—it’s a male chastity device—specifically created for little sissy boys like Brian here to prevent them from having access to their wee-wees.”
The cringing boy glanced at it fearfully, even as his cheeks and chest blushed a hot red. The idea that his hot teacher thought his little pen-is should be locked up was SO humiliating for the budding teenager.
Anna slipped a long key into the side, and the device separated into two pieces, an irregular ring and a very short, pen-is-shaped tube.
“You see Brian…this ring is positioned behind your…’equipment’,” she chuckled to herself, “and the tube slides over your little shaft. Once locked into place, this will keep your pen-is locked up safe and securely, right where it belongs.”
“I-I, d-don’t need that,” he suddenly blurted out nervously, his voice edged with fear.
“What do you think, Mrs. Evans? Would you like Brian to have his very own chastity device?”
His mother was already nodding her head enthusiastically.
“Oh yes—I think that’s exactly what he needs. Come on Brian—stand up so we can get you fitted for this,” she told him.
Brian whimpered and whined, muttering ineffectual protests under his breath but he meekly complied, standing before them as his mother tugged his clinging shorts down off of his embarrassing diaper. Fidgeting before his teacher looking like an errant toddler in his t-shirt and pampers made his cheeks flush repeatedly.
“Mom—do I hafta?” he pleaded desperately.
“Yes—this is just what you need,” she repeated, “What—you didn’t think I knew you were rubbing your fluffy soft diapers at home every time my back was turned?”
Brian cheeks and chest blushed hotly and he bit his lip anxiously without answering. The sissy’s chronic masturbating habit had finally caught up to him.
She peeled his playful-patterned plastic panties off his diaper, pulling them past his knees and began unpinning the cloth on either side of his hips.
“A boy your age, still wearing diapers, has no need for erections and this device will put a stop to yours, once and for all.”
In no time, the boy’s hairless little package was exposed, and he quickly tried to cover it with his hands.
“No need for that, honey,” his mom chided him as she pushed his hands aside and Anna came around from the other side of the desk.
“Wow—that’s really a small one,” she remarked with amusement, “Luckily, I have the size Nano with me.”
Bending down, she grasped his quivering sack in her creamy smooth hands and carefully fed it through the small, pink plastic ring.
Brian knew he was mere moments away from losing the ability to play with his little wiener, but he was helpless to stop his domineering teacher.
“N-no,” he quaked in weak protest. Clearly, he was terrified at seeing his only avenue for masturbation taken away from him.
With a small dab of lotion applied to his shy little nub, Anna fed it into the short plastic tube and then joined the two pieces, further compressing his tiny shaft inside. Brian whimpered and squirmed as Anna inserted a long key and twisted it, irrevocably locking the restrictive device in place.
“There you are, sweetie—all safe and secure,” Anna said with a broad smile as she stood up and looked down on the hapless sissy.
Standing before them, Brian’s little equipment looked even more tiny and helpless in its new pink plastic cage.
“Okay, honey—let’s get your diapers back on before you have another accident,” his mom said as she began pulling the thick cotton cloth up and around his hips. Brian pouted and stamped his feet in frustration as the bunny-headed safety pins were inserted and his diaper snugged tight on either side. His yellow plastic panties came up next, his mom tugging them up to surround the fluffy-soft Birdseye cloth.
Just then, Anna’s teacher assistant, Megan, barged into the room unannounced. She was an attractive, young brunette in her early twenties that worked closely with many of the teachers on staff.
Not realizing they were in the middle of a private conference, the pretty girl stopped dead in her tracks in shock.
“—Oh, I didn’t know you were still in meetings,” she said, although her eyes were now glued to Brian’s big, fat, diapered bottom, his babyish, shiny plastic panties reflecting the ambient light.
The latter squealed in distress and quickly bent over to grab his shorts in a belated attempt to cover his shameful diapers. Thinking quickly, Anna stepped forward and put her high-heeled toe on the garment around Brian’s ankles, preventing him from drawing them up his legs.
“No problem—what can I do for you, Megan?” she asked nonchalantly.
Walking further into the room, she suppressed a smile on her face as she looked over the sissy scrambling unsuccessfully to try and pull up his shorts. In a wild panic, Brian felt a strong, hot stream of panic-induced pee flooding into his diapers, quickly soaking the front in a humiliating display of his lack of control.
“I just have some papers for you to sign,” Megan said as she handed them over to Anna.
The latter stepped back, allowing Brian to finally pull up his shorts although the damage was already done. With a sob of shame, he tugged them up, working them over his bulky diapers in a futile attempt to hide them. Megan smirked, making no attempt to hide her amusement as she turned to leave.
As the warm pee started to seep back into the thick seat of his diapers, Brian nervously pondered how his tender bottom was going to handle another painful session with his mommy’s paddle. To be sure, his chastity was the least of his problems now.
THE END
Betty Pearl's Sissy Stories 20.1
Topic: The Parent-Teacher Conference (Read 12005 times)
