The Descent

[sissy29000]

Chapter 21: A New Restriction

It was a warm, sunny day, perfect for a visit to Johanna and Mauranne’s swimming pool. Johanna, Mauranne, and Don prepared for a relaxing day by the pool, while Ludo, was getting ready for the water.
He wore a bright purple, frilly swimsuit adorned with pastel-colored polka dots and ruffles around the edges. On his arms were inflatable princess armbands, secured tightly.

Johanna and Mauranne helped him to the poolside, where they held his hands to ensure he could safely enter the water. “Remember, Ludo, you can only go into the water when we’re holding your hand,” Johanna instructed. “You can’t swim on your own.”
Ludo nodded and carefully stepped into the shallow end of the pool, feeling the cool water against his legs. Once he was in, he played in the water, clutching his doll tightly, splashing around gently and making sure to stay close to Johanna and Mauranne.

When he wasn’t in the water, he sat by the poolside, playing with his doll and making small splashes with his feet. The grown-ups, meanwhile settled onto lounge chairs around the pool, chatting and taking naps.
Ludo listened attentively to the teenage conversation, his curiosity piqued by their topics. He wanted to join in and share his thoughts but knew he was expected to remain silent.
Johanna noticed Ludo’s attempts to participate and approached him with a firm tone. “Ludo, remember, this is not your age group. You should only speak when spoken to,” she reminded him. “This is our time to talk and relax.”
He nodded understandingly. “Yes, Miss Johanna. I’m sorry,” he said softly, lowering his gaze and focusing on his doll.

After a while, he felt the urge to use the toilet. He waddled over to where the adults were lounging, his doll still in hand, and hesitated before approaching Johanna. “Miss Johanna, Miss Mauranne, Mr. Don...” he began, but the teenagers silenced him.
Finally, he began, heading towards the house. He approached the fence surrounding the pool.
“Ludo, where are you going?” Don asked.
Ludo turned, startled. “I’m sorry, Mr. Don. I need to use the bathroom.”
Don’s tone was firm. “You need to ask for permission before going anywhere. And now, because you didn’t, there will be a consequence.”
Don guided him back to a corner of the fense. “Stand there and think about why it’s important to ask before leaving.”
Ludo stood in the corner, feeling embarrassment and regret. “I’m sorry, Mr. Don,” he said, his voice soft. “I’ll remember next time.”
After an hour Don told him he could now put his clothes back on and go home. He would pee there.

“And from now on,” Mauranne told him, “you will always ask permission to one of us before using the restroom. No matter where you are or with who you are with, pottys are no longer open access for you!”
Ludo thanked her with a curtsey and said goodbye to his master and mistresses before leaving the house.
Once home, he texted Mauranne asking for permission to go pee. She responded positively after half an hour.

[sissy29000]

Chapter 22: Bathroom Challenges

In the evening, Ludo sent a text message to Don. His hands trembled slightly as he typed.
“Good evening, Mr. Don. May I please have permission to use the bathroom?”
After a few minutes, Ludo’s phone buzzed with a reply from Don. He opened the message with anxiety.
“Permission granted only after you complete a challenge. Put on your pink leotard and send me a video of you doing five minutes of ballet moves. Make sure you curtsy at the beginning and end, and thank me for the privilege.”
Ludo hurried to his room, changed into the shiny pink leotard and positioned his phone to record the video.
He started the recording and began with a deep curtsy, addressing the camera. “Thank you, Mr. Don, for giving me this opportunity.”
He then launched into a series of basic ballet moves. Despite his discomfort and urgent need to use the bathroom, he tried his best to perform gracefully. His movements were awkward, and his face flushed with embarrassment, but he persevered, knowing that failing the challenge would only prolong his discomfort.
After five long minutes, he ended with another curtsy. “Thank you, Mr. Don, for allowing me to complete this challenge.”
Ludo stopped the recording and quickly sent the video to Don. He waited nervously for the response, hoping that his performance would be deemed acceptable.
After what felt like an eternity, he received a reply.
“You have permission to use the bathroom now. Remember to always be prompt and diligent in completing your tasks.”
As he he was sitting on the toilet bowl, Ludo couldn’t help but think about how much his life had changed. The simple act of using the bathroom had become a task fraught with challenges and humiliations, all designed to remind him of his place.

It was an ordinary school day, and Ludo was feeling the familiar pressure in his bladder. He spotted Johanna her near the lockers, chatting with her friends.
Gathering his courage, he approached her with a submissive demeanor. He waited for a moment until she noticed him.
He wanted to talk to her discreetly, she realized that, so she decided to make fun of it. She said to him, “Hi Ludo!” and she continued talking with her friends. Eventually, everyone dispersed.
Ludo took a deep breath and spoke softly.
“Miss Johanna, may I please have permission to use the bathroom?“
She looked at him with a knowing smile. She loved these moments of control and was eager to devise a challenge for him.
“Hmm, let me think,” she said, tapping her chin thoughtfully. “Alright, Ludo. Here’s your challenge: I want you to go to the school library and fetch me a book. You must carry it on your head all the way back here without dropping it. If you drop it, you have to start over. Understood?”
Ludo nodded. He knew this would be difficult, especially with his urgent need to use the bathroom. “Yes, Miss Johanna. I understand. Thank you.”
He hurried to the library, feeling the pressure mounting. He found the book Johanna had specified and carefully placed it on his head. With slow, deliberate steps, he began his journey back to the lockers, trying his best to keep the book balanced.
Each step was a struggle, and a few students gave him odd looks, but he kept his focus. He knew that dropping the book would mean starting over, which he desperately wanted to avoid.
He finally made it back to Johanna without dropping the book. He carefully removed it from his head and handed it to her, relief washing over him.
“I’ve brought the book, Miss Johanna,” he said, his voice tinged with urgency.
Johanna took the book and inspected it, her smile widening. “Good job, Ludo. You’ve earned your bathroom break.”
Ludo curtsied. “Thank you, Miss Johanna. I appreciate your permission.“

It was another challenging day for Ludo. During his third period class, he felt the familiar pressure in his bladder. He discreetly sent a text message to Mauranne, hoping for quick permission.
“Miss Mauranne, may I please have permission to use the bathroom?”
After a few minutes, Ludo’s phone buzzed with Mauranne's reply. He opened it anxiously.
“No, you may not. You can wait.”
Ludo's heart sank, but he quickly responded with the required deference.
“Thank you for your response, Miss Mauranne.”
Time dragged on painfully as he tried to concentrate on his lessons. Each passing minute intensified his discomfort. He sent another message between classes, hoping Mauranne would change her mind.
“Miss Mauranne, may I please have permission to use the bathroom now? It's becoming very urgent.”
She replied almost immediately.
“No, Ludo. You will wait.”
He sighed, his discomfort growing. He responded again, as required.
“Thank you for your response, Miss Mauranne.”
The day continued to crawl by. Ludo’s need became almost unbearable by lunchtime. He sent another pleading message to Mauranne.
“Miss Mauranne, may I please use the bathroom now? It's extremely urgent.”
Finally, she responded.
“Fine, but there's a challenge you must complete first.”
He responded gratefully, despite his anxiety.
“Thank you for your response, Miss Mauranne. I will complete the challenge.”
Mauranne quickly sent the details. “You need to find the school janitor and ask him for a mop. Bring it to the cafeteria and clean up a spill there, then you can use the bathroom.”
Ludo’s heart pounded as he read the instructions. The janitor's office was on the other side of the school, and the cafeteria was always busy during lunch. But he had no choice.
He hurried to the janitor’s office, the urgency in his bladder growing by the second. He politely asked for the mop, explaining he needed it for a spill in the cafeteria. The janitor, although puzzled, handed it over.
Ludo made his way to the cafeteria, feeling every bump and step acutely. He found a small spill near one of the tables and began to mop it up, trying to stay as inconspicuous as possible. Students around him watched with curiosity, but he kept his head down and focused on the task.
Once the spill was cleaned, Ludo quickly returned the mop and sent a message to Mauranne.
“Miss Mauranne, I have completed the challenge. May I please use the bathroom now?”
Mauranne’s reply came swiftly.
“You may, Ludo.”
He nearly ran to the bathroom, finally able to relieve himself after the long and agonizing wait. He sent one last message to Mauranne.
“Thank very much, Miss Mauranne.”

It was late at night, and Ludo found himself in desperate need of the bathroom. Despite the late hour, he dutifully sent messages to each of his master and mistresses, hoping one would respond.
“Mr. Don, may I please have permission to use the bathroom?”
“Miss Johanna, may I please have permission to use the bathroom?”
“Miss Mauranne, may I please have permission to use the bathroom?”
He waited anxiously, staring at his phone. Minutes passed, then hours, and still no response. He could see that his messages remained unread. Everyone was asleep.
He considered sneaking to the bathroom. After all, no one would know. But he couldn’t bear the thought of betraying his master and mistresses trust.
He sat on his bed, trying to distract himself from the increasing discomfort. He thought about all the times they had tested his patience and obedience, and how he had always strived to meet their expectations. This was no different, he told himself.
Hours dragged by. He checked his phone repeatedly, hoping for any sign of life from Don, Johanna, or Mauranne. The need to use the bathroom became almost unbearable, but he was determined to wait for their permission.
Finally, as the first light of dawn began to seep through his window, his phone buzzed. Mauranne had read his message.
“Why didn't you go earlier?” was her first response, followed by a second message: “Permission granted, but we'll discuss this later.”
Ludo felt a wave of relief wash over him. He quickly sent his grateful reply.
“Thank you for your response, Miss Mauranne.”
He hurried to the bathroom, finally able to relieve himself after a long and torturous night.

The morning after his long, uncomfortable night, he knew he needed to find a solution to avoid such an ordeal in the future.
He took a deep breath and typed out his message, addressing it to Don, Johanna, and Mauranne.
“Mr. Don, Miss Johanna, Miss Mauranne, may I please have permission to buy diapers for nighttime use? This would help me avoid situations like last night and ensure I remain obedient to your rules. Thank you.”
He sent the message and waited nervously for their responses.
Don was the first to reply. His message came through almost immediately.
“Diapers, huh? Feeling like a baby now, Ludo? Sure, you can get them, but you'll have to wear them properly and let us check. Understood?”
Ludo felt his face flush with embarrassment but quickly replied with the expected deference.
“Thank you, Mr. Don. I understand and will comply.”
A few minutes later, Johanna's reply came in.
“Good idea, Ludo. It will keep you from disturbing us at night. Make sure to get the most feminine ones you can find. And don't forget to thank us for allowing this.”
Ludo's heart pounded as he typed his reply.
“Thank you for your response, Miss Johanna. I will follow your instructions and ensure I get the most feminine ones.”
Finally, Mauranne's message arrived.
“I'm glad you thought of this, Ludo. It shows you're learning to take responsibility. You have our permission, but remember, you need to show us when you put them on and if they get wet, you must ask permission to remove them. Understood?”
Ludo felt a mix of relief and continued embarrassment as he replied.
“Thank you for your response, Miss Mauranne. I understand to your terms and will comply.”

That afternoon, Ludo made his way to the store, feeling self-conscious but determined. He carefully selected the most feminine diapers he could find, with pastel colors and delicate designs.
He sent a photo of the diapers along with a message.
“Mr. Don, Miss Johanna, Miss Mauranne, I have purchased the diapers as instructed. Thank you for allowing this. I will follow your rules and show you when I put them on and take them off.”
That night, Ludo carefully put on the feminine diapers, feeling a both relief and embarrassment. The pastel colors and delicate designs made him feel even more submissive. He sent the obligatory message to his master and mistresses, informing them that he was ready for bed, with a selfie attached.
“Mr. Don, Miss Johanna, Miss Mauranne, I have put on the diapers for the night. Thank you for allowing this. Goodnight.”
Don responded quickly.
“Goodnight, Ludo. Sleep well, and remember, you're doing this to stay obedient.”
Johanna added her own comment.
“Good job, baby! This will help you stay on track.”
Mauranne finished with a final note.
“Sleep tight, little Ludo. We'll check in the morning.“
Ludo lay down, feeling more secure knowing he wouldn’t have to endure another terrible night. As he drifted off to sleep, he thought about how much he had adapted to their rules and control.

The next morning, he woke up early. For the first time since he was a baby, he had peed in diapers. He felt ashamed and dirty, but also even more submissive, and somehow relieved that he hadn't had to wait for permission to go to the bathroom. He sent a quick message to Don, Johanna, and Mauranne, letting them know he was awake and ready for his morning check.
“Good morning, Mr. Don, Miss Johanna, Miss Mauranne. I am awake and ready for my morning check. Thank you.”
Don replied promptly.
“Be ready in five minutes. We'll call you.”

Soon, his phone buzzed. It was a video call from Don, with Johanna and Mauranne joining in. Ludo answered, his heart pounding.
Don's voice was stern. “Show us the diapers, Ludo.”
Ludo stood up and adjusted the camera, making sure they could see the pastel-colored diapers he was wearing. He felt his face flush with embarrassment as he displayed them.
Johanna smirked. “Very good, Ludo. I see you made good use of your diapers!Now, take them off.”
With shaking hands, Ludo carefully removed the diapers.
Mauranne nodded approvingly. “Good job, Ludo. Now, dispose of them properly and get ready for your day.”
“Thank you, Mr. Don, Miss Johanna, Miss Mauranne, for allowing me to use the diapers like a good little baby. I will continue to follow your instructions obediently.”

[sissy29000]

Chapter 23: A Baby's Night

For their next evening together, Johanna and Mauranne had planned a night with their “baby sister”.

As soon as he arrived, they led him to the bathroom, where a warm bath awaited him. The tub was filled with bubbles, and colorful bath toys floated on the surface.
Johanna carefully undressed him, and he stepped into the tub with Mauranne’s help.
Mauranne took a bottle of baby soap and a soft washcloth, beginning to wash his hair and body. “Let’s get you all clean,” she said, scrubbing gently. Johanna attended to Ludo’s back and legs, ensuring he was thoroughly washed.
Ludo enjoyed the bath, playing with toys and splashing gently. “Thank you, Miss Johanna and Miss Mauranne,” he said, smiling.
They wrapped him in a fluffy towel, drying him off carefully. They diapered him and produced a cute, pastel-pink onesie with a playful pattern.

Then, he was seated in a high chair for dinner, staring at the dish before him. The concoction on his plate was a bizarre mix of ingredients: chunks of raw vegetables, a dollop of mashed potatoes, slices of fruit, and a splash of what looked like soy sauce. The colors and textures clashed in a way that was both unappetizing and unsettling.
Mauranne, Johanna and Don watched him with amusement and expectation. Johanna, with a playful smirk, said, “This is our special mixed dish. Remember, you need to eat all of it and enjoy it.”
Don, leaning casually against the counter, added, “And don’t forget, if you gag or complain, there will be consequences. We want you to show how much you appreciate our cooking.”
Ludo’s stomach churned as Johanna approached with a spoonful of the concoction. The smell was a strange blend of sweet, salty, and sour, making him feel queasy before he even tasted it.
“Here comes the airplane,” she said, feeding him the spoonfuls. Ludo hesitated at first but opened his mouth.
As he ate, he grimaced at the taste.
Mauranne patted his head and said, “Ludo, remember to be polite and grateful. Finish your dinner, and it will be over soon.”
With a deep breath, he accepted the next spoonful in his mouth, trying to suppress his gag reflex. He chewed slowly, forcing himself to swallow despite the unpleasant texture and taste.
As he continued being fed, the mixture seemed to congeal into an even more unpalatable mess. He tried to focus on his task, putting on a brave face and forcing a smile. However, the combination was too much for him, and he soon felt the familiar urge to gag.
His face contorted as he tried to keep the food down. Mauranne, Johanna and Don watched him intently, their expressions shifting from amusement to mild irritation.
Johanna leaned forward, her voice firm. “Are you having trouble? We specifically asked you to eat this without complaints. It’s not polite to gag or make faces.”
Ludo tried to regain his composure, swallowing hard and nodding. “I’m sorry, Miss Johanna.”
Each bite felt like a struggle, the taste lingering unpleasantly in his mouth. Despite his best efforts, he found it impossible not to gag occasionally.
Don, shaking his head with a hint of disappointment, said, “You’re not making this easy for yourself. You need to show that you’re grateful for the effort we put into making this meal.”
With each gag, Ludo’s anxiety grew. He felt a deep sense of shame, knowing that his discomfort was being met with scolding rather than sympathy. He tried to smile and nod, hoping it would make the process go smoother, but the mixture’s taste and texture continued to revolt him.
When Johanna put down the spoon, Ludo's face flushed and his hands trembling slightly. “Thank you, Miss Johanna,” he said, his voice weak. “The meal was yummy.”

Johanna and Don exchanged a look, and Johanna said, “Well, I suppose you did manage to eat it all. But don’t think this means you’re off the hook.”
Mauranne placed a bowl of what looked like a bizarre mix of ingredients before Ludo, a chaotic combination of gelatin, canned fruit, whipped cream, and some questionable chocolate sauce that seemed to have separated into an unappealing sludge.
“Time for dessert,” Johanna announced with a grin. “We wanted to make sure you finish your meal properly, so here’s a little something to top it off. Remember, you need to eat all of this, too.”
Don, watching with a satisfied smirk, added, “And just like before, you need to act like you enjoy it. Complaining or gagging will only make things worse.”
Ludo’s heart sank as he saw the dessert. The sight of the gloppy mixture made his stomach churn, and the smell was only slightly more bearable than the main course. He picked up the small plastic spoon and dipped it into the bowl, trying to mentally prepare himself for the challenge ahead.
As he took the first bite, he tried to focus on the sweet taste of the whipped cream, but it was overpowered by the gelatin’s rubbery texture and the strangely sour fruit. He forced himself to chew and swallow, but the combination of flavors and textures made him want to gag.
Mauranne leaned in and said, “You’re doing well so far, but remember to keep smiling and enjoying your dessert.”
Ludo tried to keep his face composed, but his efforts were becoming increasingly difficult. The mixture was not only unappetizing but also made him feel nauseous. He took another bite, struggling to keep his expression neutral.
As he continued eating, his discomfort grew. He could feel the texture of the gelatin clinging to his throat, and the taste of the fruit was becoming overwhelming. Despite his best efforts, he couldn’t completely suppress his reactions, and a few more gags slipped through.
Don’s amusement faded as he noticed Ludo’s struggles. He crossed his arms and said, “I see you’re having trouble again. Remember, if you don’t finish it properly and without complaints, there will be consequences.”
Ludo, feeling a surge of anxiety, nodded and took another spoonful. His face was flushed, and his hands trembled as he brought the spoon to his mouth. He tried to focus on finishing the dessert, each bite feeling like an immense challenge.
Eventually, he managed to finish the bowl, though he could barely keep a smile on his face. The combination of flavors had become a blur of unpleasantness, and he was relieved to be done.
He put the spoon down and looked at Mauranne, Johanna and Don, his voice trembling slightly. “Thank you, Miss Johanna, Miss Mauranne and Mister Don for this delicious dessert.”

As the night wore on, Ludo began to feel the urge to pee. He approached Johanna, his cheeks flushed with embarrassment.
“Miss Johanna,” Ludo began softly, “may I please use my diaper?”
Mauranne looked at him and nodded.
“Thank you, Miss Johanna,” Ludo said.
Once he had relieved himself, Ludo decided to show his gratitude. He crawled over to Johanna, who was seated comfortably on the couch. With a warm, genuine smile, he wrapped his arms around her waist and leaned in for a long, tender hug. Johanna was initially surprised but quickly relaxed, placing a comforting hand on his back.
“Thank you, Miss Johanna,” Ludo murmured, his voice soft against her. “I’m so happy to be here with you.”
He then tilted his head up, planting a series of gentle kisses on her hand. Johanna responded with a warm smile, patting Ludo’s head affectionately.
“You’re very sweet, Ludo,” she said warmly. “I really appreciate this.”

He then turned to Mauranne, who was sitting beside her sister. He approached her with the same warmth, wrapping his arms around her legs and resting his head on her lap. Mauranne looked down at him with a gentle smile, clearly touched by the gesture.
“Thank you, Miss Mauranne,” Ludo said, his voice full of sincerity. “I’m really grateful for everything.”
He then leaned in to kiss her knees. Mauranne, smiling warmly, gently stroked his hair and patted his back.
“That’s so kind of you, Ludo,” she said. “You’ve been a wonderful little sister tonight.”

Finally, he moved to Don, who was seated in a nearby armchair. With a shy but determined expression, he wrapped his arms around Don’s knees, hugging them tightly. Don looked down at him.
“Thank you, Mr. Don,” Ludo said, looking up with a heartfelt gaze. “I’m really grateful for your kindness.”
Ludo then placed kisses on Don’s legs. Don, clearly pleased, started to gently pet his head. After a moment, he began to lightly tickle Ludo’s neck with his fingers. Ludo’s response was immediate: he squirmed slightly and let out a soft giggle.
“Oh, thank you, Mr. Don,” Ludo said, still giggling. “That feels nice.”
Don chuckled, continuing the gentle tickling, which made Ludo laugh even more.

As the evening wound down, Ludo was prepared for bed.
“Goodnight, Miss Johanna. Thank you for everything,” Ludo said with a curtsey.
“Goodnight, Miss Mauranne. Thank you for taking care of me,” he added, curtsying again.
“Goodnight, Mr. Don. Thank you for being here,” he finished, offering a final curtsey.
After changing his diaper, the girls began the bedtime routine. They helped him into a cozy crib-like bed, tucked him in with a blanket, and placed Ludivine beside him.

During the night, Mauranne approached Ludo’s crib with careful steps, trying not to wake him. As she approached his bed, the faint, unpleasant odor of a soiled diaper became noticeable.
With a smirk, she leaned in closer, her eyes settling on Ludo’s slightly sagging diaper, which indicated a recent accident.
“Looks like someone had an accident in their sleep,” Mauranne whispered to herself, stifling a giggle.
She gently shook Ludo’s shoulder. “Ludo, wake up,” she said softly, though her tone was edged with excitement. “I need you to wake up.”
Ludo stirred, blinking sleepily as he slowly came to consciousness. His face flushed with embarrassment as he realized the situation. He winced slightly, knowing he had soiled his diaper.
Mauranne tried to suppress her laughter but couldn’t help a few chuckles. “Oh dear,” she said, her voice dripping with mock sympathy. “Looks like you made quite the mess. Did you have a little accident while you were sleeping?”
Ludo, his cheeks reddening, nodded slightly. “I’m sorry, Miss Mauranne,” he mumbled, his voice barely audible. “I didn’t mean to.”
She took a moment to compose herself, enjoying the situation before her. “Well, since you’re already in a bit of a mess, we’ll need to get you cleaned up,” she said, still with a teasing tone.
She carefully helped Ludo out of bed and guided him to the changing table she had set up in the room.
Ludo, feeling utterly humiliated, complied without protest. He lay down on the changing table as Mauranne began the process of cleaning him up. She removed the soiled diaper with practiced ease, cleaning him thoroughly before putting on a fresh diaper.
After he was clean and dressed in a fresh pair of pajamas, Mauranne gave him a pat on the back. “All done,” she said with a reassuring smile. “Now you can go back to sleep. Just try not to make any more messes, okay?”
Ludo, though still embarrassed, managed a small smile of gratitude. “Thank you, Miss Mauranne,” he said softly, his voice filled with genuine appreciation.

In the morning, Johanna said with a teasing grin, “I heard you had quite a poopy night. Was the diaper really that full?”
Ludo felt his cheeks flush with embarrassment. He looked down, trying to avoid eye contact. “Yes, Miss Johanna,” he said softly. “I didn’t realize...”
“Good morning, Ludo!” Mauranne called out with exaggerated cheerfulness. Her tone, though sweet, carried an undercurrent of mockery. “How are you feeling today?”
Ludo responded quietly, “Good morning, Miss Mauranne. I’m feeling okay.”
Johanna, seated next to Don, stifled a laugh as she looked at Ludo. “Oh, I bet you are,” she said, her eyes twinkling with amusement. “Considering how ‘busy’ you were last night.”
Don, who was pouring himself a cup of coffee, glanced at Ludo with a smirk. “Yeah, you really made quite a mess,” he said, his voice dripping with playful sarcasm. “It’s not every day we get to see someone fill their diaper like that.”
“Maybe you shouldn't have eaten that dish and dessert with so many laxatives in it?” Mauranne asked, unable to hold back her laughter.
Ludo’s face turned bright red, a mix of embarrassment and frustration washing over him. “Yes Miss Mauranne, please forgive me Miss Mauranne.”
Don, always enjoying a good jest, smirked and chimed in. “You really should be more mindful, Ludo. We wouldn’t want you to start leaking everywhere, would we?”
Ludo nodded, with embarrassment. “I’m sorry, Mr. Don,” he mumbled. “I’ll be more careful.”

[sissy29000]

Chapter 25: A Hot Day

On a particularly hot morning, Ludo was arriving at school when Mauranne cornered him at the entrance.
“Good morning, Ludo,” Mauranne said with a smile. “I have a little surprise for you.”
She handed him a very feminine T-shirt and a large, thick wool sweater. The T-shirt was a bright pastel pink with a cute cartoon character on the front, while the sweater was oversized and knitted, with a chunky design that made it look even more exaggerated.
“Since it’s such a hot day, I’m sure you’ll enjoy wearing this,” Mauranne said sweetly. “You need to change into these clothes right here. And remember to thank me properly.”
Ludo’s face flushed. He glanced at the oversized sweater and the brightly colored T-shirt, feeling the heat from both the temperature and the situation.
In full view of other students arriving at school, Ludo reluctantly took off his normal clothes and replaced them with Mauranne’s chosen outfit. He put on the T-shirt first, followed by the wool sweater. The sweater was so big and heavy that it felt almost comically out of place, making him sweat even more.
Ludo adjusted the sweater awkwardly and turned to face Mauranne. “Thank you, Miss Mauranne,” he said. “I appreciate your gifts.”
As Ludo made his way through the school hallways, he was faced with a tough choice: endure the sweltering heat in the thick wool sweater or deal with the embarrassment of the humiliating T-shirt.
If he chose to wear the sweater throughout the day, he would find himself sweating profusely. The wool sweater made it unbearable, and he would be drenched in sweat by the end of the day, feeling uncomfortable and sticky. This choice also meant he was constantly aware of how out of place he looked compared to his classmates.
If he decided to remove the sweater and just wear the T-shirt, he would expose the embarrassing design to everyone. The T-shirt’s bright pink color and childish cartoon character drew unwanted attention from his peers. He would face teasing and whispers from classmates, adding to his feelings of humiliation.
Ludo chose to endure the heat, keeping the sweater on throughout the day. He hoped that by not exposing the T-shirt, he could avoid some of the embarrassment. However, the oppressive heat and constant sweat made his choice a particularly grueling one.
He found himself constantly overheating, struggling to stay focused in class, and feeling self-conscious about his appearance.

After a long, hot day, he was visibly drenched and uncomfortable. As he was about to leave, Mauranne, Don, and Johanna caught up with him. Mauranne couldn't help but laugh at Ludo’s predicament.
“Oh, Ludo,” Mauranne teased with a smirk, “You’ve been wearing that big wool sweater all day? Didn’t you think to take it off when it got so hot?”
Ludo’s face flushed with embarrassment. He forced a sheepish smile and played along with Mauranne’s mocking. “Oh, Miss Mauranne, I… I didn’t think of that. I guess I was so focused on following your instructions that I didn’t realize how hot it was.”
Mauranne and the others enjoyed his discomfort. “It’s alright, Ludo,” Mauranne said, trying to sound sweet but with a hint of sarcasm. “I’m glad I could teach you a lesson in common sense. Sometimes it’s good to be guided by someone as intelligent as me.”
Ludo lowered his eyes and nodded. “Thank you, Miss Mauranne, for guiding me and showing me how to think better in these situations. I really appreciate your intelligence and guidance.”
Don grinned and said, “Looks like Ludo learned the hard way today.”
Johanna chuckled. “Yeah, it’s really funny how he didn’t think of just taking off the sweater. Classic!”
The three of them continued to make light of Ludo’s discomfort. They laughed and joked about how he had suffered all day due to his own oversight.
Don added, “Just remember, next time, think a bit more before you overheat yourself!”
Ludo tried to laugh along, but his embarrassment was palpable. He continued to thank them, “Thank you all for the lesson. I’ll definitely remember this experience and try to be more thoughtful in the future.”

[sissy29000]

Chapter 26: The Shopping Trip

One afternoon, Johanna and Mauranne led Ludo into a boutique specializing in children’s clothing.
He had to pick by himself underwears, tights, a skirt, a dress, blouses, sweaterand cardigan, and ballet flats.
Ludo chose several pairs of frilly, pastel-colored underwear with lace trim. He felt self-conscious but managed to place them in his basket.
He selected white tights with a delicate floral pattern, feeling slightly embarrassed.
He picked a fluffy, layered tutu in soft pink. The skirt’s multiple tiers of tulle and satin waistband were perfect for a feminine look.
For his dress, Ludo first picked out a knee-length, light blue dress adorned with white polka dots and a bow at the waist. However, Mauranne immediately intervened.
“No Ludo, blue is too masculine for you! You need something that looks more feminine,” she said, setting the dress aside. “Let’s find another one.”
Ludo reluctantly put the blue dress back and chose a pastel pink one, with lace details instead. Johanna and Mauranne approved of this more suitable choice.
He initially selected a mint green blouse with a ruffled collar. Johanna examined it critically and shook her head. “Ludo, this green blouse is not quite right. It’s not as feminine as we’d like. Let’s find something in a softer shade.”
He opted instead for two blouses: one in pale lavender with lace trim and another in a soft pink with ruffled sleeves with floral embroidery. Both were delicate and feminine, which Johanna and Mauranne approved.
He picked a soft, pastel pink sweater with heart-shaped buttons. It was cozy and aligned well with the feminine theme.
He chose a white cardigan with embroidered flowers. It was lightweight and added a cute touch to the outfits.
He finally opted for shiny silver ballet flats with little bows. They were a perfect match for the clothing.
Ludo approached the checkout counter. The cashier rang up the items with a smile.
“Lovely choices,” she said, glancing at Ludo. “These outfits are adorable.”
Ludo managed a shy smile. “Thank you Miss,” he said, handing over the payment.

“From now on, you will always have to wear one of your panties instead of your boy underwear,” Johanna told him.
“Yes Miss Johanna, thank you Miss Johanna and Miss Mauranne,” he said with a curtsey.

[sissy29000]

Chapter 27: Underwear Checks

Next day, Ludo went about his classes, trying to keep his mind focused on his studies despite the secret feminine layers beneath his clothes.
During lunch break, Mauranne found him alone in a quiet corridor.
“Hey, Ludo,” she said casually, “It’s time for a little check-up to make sure you’re following the rules.”
She led him to a secluded part of the corridor and motioned for him to lift his shirt slightly. “Just a quick check. Lift your shirt so I can see.”
Ludo hesitated but complied, lifting his shirt just enough for Mauranne to get a glimpse of the waistband of his underwear. Mauranne’s eyes scrutinized the garment.
“Hmm,” she said, her tone satisfied. “Good job, Ludo. It’s important to follow these rules, and you’re doing well. Just remember to keep everything in place and continue to adhere to our expectations.”
Ludo let out a sigh of relief and straightened his clothes. “Thank you, Miss Mauranne. I’ll make sure to keep following the rules,” he said, his voice trembling slightly.
With that, she left him to return to his classes, while he adjusted his clothes and tried to regain his composure. The inspection had been a nerve-wracking experience, but he felt a sense of relief knowing he had complied with the expectations set by Mauranne and Johanna.

On a sports class day, Ludo faced the dilemma of having to wear his sports uniform and changing in the locker room with his classmates. To avoid embarrassment, he decided to wear boys' underwear instead of the girls' that was required. He hoped to blend in and avoid drawing attention.
Everything seemed to go well until the sport class ended, and the students were heading back to the locker room to change.
Don arrived at the locker room, a place Ludo hadn't anticipated he would be inspected. He had come to check up on Ludo’s adherence to the rules regarding his clothing.
“Hey, Ludo,” Don said with a commanding presence. “I need to do a quick inspection to make sure you’re following the guidelines.”
Ludo’s heart sank as he realized his mistake. “Uh, yes, Mr. Don,” he replied nervously.
Don approached Ludo. Ludo tried to act nonchalant, but Don’s sharp eyes quickly assessed the situation.
“Lift your shirt,” Don commanded, his tone firm. Ludo hesitated but complied, lifting his shirt just enough for Don to see the waistband of his underwear. Don’s eyes narrowed as he noticed the boys' briefs.
His face hardened. “Ludo, this is boys’ underwear. This is a clear disobedience.”
Ludo’s cheeks flushed with shame. “I’m sorry, Mr. Don. I didn’t want to be seen in the locker room.”

Don’s took Ludo to a private area of the school. It was a small, unused classroom that was rarely visited by students. The room was stark and unwelcoming, which only heightened Ludo’s anxiety about the impending punishment.
He was instructed to kneel in the center of the room. The hard floor was cold and uncomfortable, and he shifted slightly, trying to find a position that was less painful.
Don stood over him, crossing his arms. “You will start by apologizing for your your extremely serious act of disobedience.”
Ludo gulped and looked up at Mr. Don. “I apologize, Mr. Don. I should have followed the rules. I understand now that it’s important to comply no matter what.”
Next, Don instructed him to stand with his back to the wall, arms extended straight out to his sides. This position forced him to remain still and maintain a posture of submission.
To increase the discomfort, Mr. Don added a requirement that Ludo hold a stack of books in his outstretched hands. The books were not excessively heavy, but they were enough to cause his arms to ache and make the experience more strenuous.
While in this position, Ludo was required to remain silent and reflect on his behavior. Don walked around the room, occasionally reminding him to stay focused and maintain his posture.
After the time had passed, Don approached him and said, “Now, you will apologize again and promise to improve your compliance in the future.”
Ludo, exhausted and uncomfortable, managed to say, “I’m sorry, Mr. Don. I promise to follow any instructions in the future.”
Don nodded. “You’ve learned the lesson. But you're still wearing your little boy's briefs. Well, we can't have that, can we? Turn around.”

Ludo obeyed, feeling a lump form in his throat. Before he could prepare himself, Don yanked on the waistband of his underwear, giving him a brutal wedgie. The fabric stretched painfully, digging into his skin. Ludo winced, trying to endure the discomfort.
Don didn't stop until the elastic and fabric snapped with a loud noise. He kept pulling until he was able to rip them off completely. He threw them on the ground. Ludo stood there, red-faced and humiliated, trying to hold back his tears.
“You won't be needing those anymore,” Don said with a satisfied chuckle. “Remember this, little girl: no more boy's underwear. Ever.”
“Yes, Mr. Don. I promise,” Ludo replied, his voice barely above a whisper.
Ludo spent the rest of the day without any underwear, feeling vulnerable and exposed with every movement. The breeze reminded him of his predicament, and he couldn't escape the feeling of shame that clung to him.
That night, as he changed into his nightclothes, he vowed never to wear boy's underwear again.

After this incident, he never failed to wear his girly panties. Checks were frequent and could occur anywhere.
Mauranne would corner him during recess in the playground.
“Ludo, show me and tell me what you’re wearing today and tell me how much you like it,” she would say softly.
Ludo would quickly pull down the waistband of his trousers to reveal his frilly, pastel pink panties. “Miss Mauranne, I’m wearing these lovely pink panties. I’m very fortunate to wear such pretty underwear.”

Some other day, in a quiet school corridor, Don approached Ludo. The hall was nearly empty, providing a bit of privacy for the inspection.
“Ludo,” Don said with a hint of authority, “show me your underwear.”
Ludo pulled down his pants slightly to display the bright purple panties with ruffled edges. “Mr. Don, I’m wearing these beautiful purple panties. I’m very lucky to have such elegant panties.”
Don inspected them briefly and said with a smirk, “Well done. Keep up the good work.”
Ludo pulled his pants back up and curtsied, “Thank you, Mr. Don.”

Again once more, in the school toilets, Johanna waited for Ludo to finish his business. Once he was alone, she moved in for a quick check.
“Ludo, show me your panties,” Johanna said with a teasing tone.
He reluctantly lifted his pants to reveal his white panties with a small bow on the front. “Miss Johanna, these white panties are so cute. I love the pink bow so much. It's a privilege to wear these panties.”
Johanna smiled, clearly pleased with the check. “Nice. You’re doing well.”
Ludo thanked her before adjusting his clothing, “Thank you, Miss Johanna.”

During lunch in the school refectory, Mauranne managed to pull Ludo aside. The cafeteria was noisy, which helped with privacy.
“Let’s see your panties,” Mauranne said quietly.
Ludo lifted the waistband of his trousers to show off his bright pink panties with a cartoon character. “Miss Mauranne, I’m wearing these fun panties. Thank you so much for allowing me to have such playful underwear.”
Mauranne inspected them with a smile. “Very nice. Keep wearing them proudly.”
Ludo curtsied to her, “Thank you, Miss Mauranne.”

On the way home from school, Don decided to conduct a surprise check. The street was less crowded, providing a bit of cover.
“Ludo, let me see your underwear,” Don instructed.
Ludo pulled down his pants slightly to reveal cherry colored panties. “Mr. Don, these cherry panties are so pretty. I’m very lucky to wear them.”
Don looked at them and nodded. “Good.”
Ludo curtsied with a forced smile, “Thank you, Mr. Don.”

At the local park, Johanna managed to find Ludo alone in a quieter area. She decided it was time for a check.
“Show me your underwear,” she said.
Ludo, feeling anxious, lifted the waistband of his trousers to display panties decorated with tiny flowers. “Miss Johanna, I’m wearing these lovely flowered panties. I adore them.”
Johanna inspected them and smiled. “Nice choice. Keep it up.”
Ludo curtsied, “Thank you, Miss Johanna.”

Even during a movie at the cinema, Mauranne managed to give Ludo a wedgy.
“Ludo, let’s check your panties,” Mauranne whispered with a grin.
Ludo bend to help her have a view on his delicate lace-trimmed panties. “Miss Mauranne, I’m wearing these elegant lace panties. I’m so fortunate to have such sophisticated underwear.”
Mauranne looked at the panties with satisfaction. “They look great. Keep appreciating them.”
Ludo nodded, “Thank you, Miss Mauranne.”

Throughout these checks, Ludo always complied with a polite smile, showing his underwear as requested and expressing gratitude despite his deep embarrassment even if his anxiety about being noticed was still immense.

[sissy29000]

Chapter 28: Gifts In The Locker

One morning, Ludo opened his locker and found a pair of hot pink tights neatly folded inside. The vibrant shade and the delicate fabric immediately stood out. Ludo’s heart sank as he understood that he was expected to put on the tights before the next check. He knew he had to act quickly.
He hurried to the restroom, discreetly removed his regular trousers, then carefully slid his legs into the pink tights. The fabric was snug and slightly shiny, with a soft, almost velvety texture that felt alien against his skin.
He adjusted his clothing as best as he could to minimize their visibility, but the hot pink tights were still noticeable through the thin fabric of his pants.
When Mauranne approached for the check, she greeted Ludo with a teasing tone.
“Ludo, let’s see what you’re wearing today.”
Ludo gulped and lifted his shirt slightly to reveal the pink tights peeking out from his trousers. The bright color was hard to miss.
She chuckled and said, “Oh, Ludo, I see you’ve found my tights. They look just adorable on you.”
Ludo’s face turned crimson. He managed a nervous smile and said, “Thank you for this delicious gift Miss Mauranne.”

One morning, Ludo opened his locker to find a shiny pink leotard folded neatly inside. The leotard was made of a sleek, stretchy material with a glossy finish that caught the light. He felt a sense of dread knowing how noticeable it would be.
In the restroom, he had to completely take off all of his clothes to put on the leotard. He tried to adjust his outer clothing to cover as much of it as possible. He pulled on his regular pants and shirt, but the form-fitting nature of the leotard meant it was still visible around the edges. The leotard felt restrictive and uncomfortable, adding to his unease.
He tried to walk normally, but the tightness of the leotard made him feel self-conscious.
Mauranne approached with her usual playful smile.
“Ludo, let’s see what you’re wearing today,” she said, clearly excited.
Ludo reluctantly lifted the hem of his shirt, revealing the shiny pink leotard underneath. The vibrant color and glossy finish were impossible to miss.
Mauranne’s examined the leotard closely, her grin widening. “Oh, Ludo, you look absolutely fabulous in this leotard! It’s perfect for you. I’m so pleased with how well you’re wearing it.”
Ludo forced a nervous smile and thanked her profusely.

Later that day, Ludo met Don in the school corridor. Don's eyes quickly landed on Ludo, and he noticed the telltale signs of the shiny pink leotard peeking out from under his clothes.
“Ludo, I see you’re wearing something quite special today. Let’s have a proper look at it, shall we?”
Ludo felt a surge of panic. He knew he had to remove both the top and bottom of his normal outfit to reveal the full leotard. The idea of exposing himself fully in such a public area was deeply embarrassing, and he feared that someone might walk by.
He hesitated, his face turning red as he fumbled with the buttons of his shirt, trying to avoid the full reveal. His hands shook slightly, and he tried to offer a nervous smile.
Don noticed Ludo’s hesitation and raised an eyebrow, his expression turning more serious. “Ludo, hesitation like this warrants a punishment. You need to show the full leotard now.”
Ludo’s heart raced. He knew that Mr. Don’s tone meant business, and he couldn’t afford to disobey.
He pulled off his shirt and pants, letting them fall to the floor. The leotard’s glossy surface shimmered under the fluorescent lights, its bright pink color and lace details now fully visible. He stood awkwardly in the middle of the corridor.
Don inspected the leotard with an amused yet authoritative gaze. “Well, well, Ludo. You’re certainly putting a lot of effort into embracing this outfit. The leotard looks just as fabulous as I imagined.”
Ludo stood still, trying to ignore the growing sense of embarrassment. He forced a nervous smile and said, “Thank you, Mr. Don. I’m very fortunate to have such a beautiful piece of clothing.”
Don nodded, clearly pleased with the sight but still serious. “Good. Now, because you hesitated, there will be a punishment for your behavior today.
Ludo nodded. “Yes, Mr. Don. I understand.”
After Don finished his inspection, he motioned for Ludo to get dressed. Ludo quickly put his clothes back on, feeling the leotard’s fabric pressing against him as he dressed over it.
“Thank you, Mr. Don. Please forgive me for my hesitation. I am deeply sorry.”
“Sorry isn't enough,” Don replied sharply.
He glanced around, ensuring the hallway was still empty, then motioned for Ludo to follow him and texted Johanna and Mauranne to join them.

“What's going on?” Johanna asked, smirking.
“Ludo here hesitated during his inspection,” Don explained. “We need to remind him of his place.”
Mauranne's eyes gleamed with excitement. “Oh, this will be fun.”
They led Ludo into an empty classroom, closing the door behind them. Don turned to face Ludo, his expression serious. “Strip,” he commanded.
Ludo's hands trembled as he slowly removed his clothes, the humiliation burning on his cheeks. Once he was down to his leotard, Don shook his head. “All of it, Ludo.”
With a deep breath, Ludo complied, standing naked before them. Johanna and Mauranne snickered, whispering to each other.
“Now, what should his punishment be?” Don mused, looking to the girls for suggestions.
“How about some lines?” Johanna suggested. “He can write, 'I must obey without hesitation' a hundred times.”
Her friends agreed and she Johanna handed him a piece of paper and a pen. “Get started on those lines,” she ordered.
Ludo sat down at a desk and began writing, the shame of his situation making it hard to concentrate. He knew that any further hesitation would only make things worse.
As he wrote, Johanna and Mauranne took colorful markers and stickers and started writing and sticking on him.
“Now, go to class,” Don ordered. “And remember, any hesitation will be met with even harsher punishment.”
Ludo nodded, his eyes downcast. “Yes, Mister Don. Thank you Mister Don, Miss Johanna and Miss Mauranne.”

Once he was dressed again, the marks could still be seen on his wrists and neck.
As he walked through the hallways, he could feel the stares and hear the whispers of his classmates. The humiliation was almost unbearable, but he knew he had no choice but to endure it.
By the end of the day, he found Don, Johanna, and Mauranne waiting for him outside the school.
“Did you learn your lesson?” Don asked, his tone demanding.
“Yes, Mister Don,” Ludo replied quietly.
“Good,” Don said with a satisfied nod. “Remember, Ludo, you are to obey without question or hesitation. Understood?“
“Yes, Mister Don. Thank you Mister Don, Miss Johanna and Miss Mauranne,” Ludo repeated with his best curtsey.