The Descent

[sissy29000]

Chapter 29: Less Discreet Gifts

Ludo’s day began with a nervous flutter when he discovered the latest surprise in his locker, wrapped in shiny silver paper with a large pink bow: a pair of neon pink, sparkly bloomers, adorned with glitter and a frilly lace trim.
Hurrying to the restroom, he quickly changed into the bloomers, trying to hide them under his school clothes.
“Good morning, Ludo. Let’s see how you’re handling today’s little challenge,” Don said with a playful grin by cornering him behind a door just before entering class. He lifted Ludo’s shirt, revealing the neon pink bloomers. The sight made Don chuckle.
“Well, look at that,” Don said, clearly amused. “You’re really sparkling today.”
Ludo’s face flushed with a deep crimson hue. “Yes, Mr. Don,” he managed to reply, his voice barely above a whisper.
Don pulled his pants down to his knees to inspected the bloomers with evident delight.

In class, Ludo could feel the neon pink fabric rubbing against his skin. Every time he shifted in his seat, the bloomers seemed to chafe and itch.
While the teacher was explaining a new topic, Don whispered sharply, “Ludo, you forgot to thank me for my thoughtful gift, you’ll need to make up for it.”
Ludo became livid at his forgetfulness. He begged for Don's forgiveness, avoiding attention and knowing he wouldn't escape punishment. He just hoped it wouldn't happen in class.
His eyes widened with concern as he felt Don’s hand discreetly slip small, uncomfortable accessories to him. Don's quiet command was clear: Ludo was to put it on and endure its effects for the remainder of the class.
The accessories turned out to be a pair of tight, glittery ankle cuffs that jingled with every step and bracelets with little bells. Ludo had to put the bracelets on his ankles and wrists, making every move more noticeable and uncomfortable.

The rest of the class was a grueling experience for Ludo. He struggled to focus on the lesson while trying to minimize the sound of the jingling.
When the class ended, Don approached Ludo once more. “I hope you’ve learned the importance of expressing gratitude?” Don said with a smirk.
Ludo nodded and thanked Don profusely. “Thank you, Mr. Don. I’m really sorry for forgetting,” he said, his voice filled with genuine regret.
Don’s grin widened as he heard Ludo’s sincere apology. “Good,” Don said, clearly satisfied. “Remember, it’s all about showing respect, no matter what.”
For the rest of the day, the sound of the tiny bells was faint but insistent, a constant reminder of his punishment. The jingling sound was subtle but persistent, a reminder of his lapse in manners.

[sissy29000]

Chapter 30: Home Visit

One day after school, Johanna and Don followed Ludo home. He understood that he had to bring them in, glad that his Mom hadn't come home yet.
“Please, come in,” Ludo said as he ushered them inside.

Once inside Ludo’s room, Johanna and Don started by inspecting Ludo’s drawer, where his boy’s underwear was still neatly stored.
“Ludo, we’ve decided to update your wardrobe,” Johanna said with a mischievous grin. “We’re going to replace all your useless and inappropriate boy’s briefs with girls’ underwear.”
Don helped Johanna remove all the boy’s underwear from the drawer and replace them with various pairs of feminine underwear: lacy panties, pastel-colored briefs, and frilly designs.

Just as Don and Johanna were finishing, Ludo’s Mom arrived home. She came to see him in his room and met his friends.
“Mom, this is Johanna and Don. They’re friends from school,” Ludo introduced them.
Ludo’s mother, pleased to finally meet her son’s friends, greeted them warmly. “It’s lovely to meet you both. Ludo has mentioned you a lot. Please, come and stay for dinner.”
During dinner, Don and Johanna allowed Ludo to address them by their first names, dropping the formal titles of “Miss” and “Mr.” as long as his mother was present. However, they instructed him to count how many times he used their first names, as he would be punished for each infraction later.
Throughout the meal, they whispered orders to Ludo, which he had to follow without drawing his mother’s attention.
“Ludo, can you pick up my fork off the floor please?” Johanna said. And once under the table he had to kiss her foot.
“Ludo, clear my plate, please,” Don added, making sure his instructions were carried out promptly.

Ludo’s mother engaged Johanna and Don in conversation. “Ludo is such a shy boy and has a hard time at school. I’m glad to see he’s found friends who seem to help him come out of his shell.”
Johanna smiled warmly. “Oh, yes, we’re very good friends with Ludo. We help him grow and learn to be more responsible and mature.”
Don nodded in agreement. “We’re here to support him and help him become a better person.”
As the conversation progressed, his mother turned to Ludo. “Ludo, it seems like you’ve made some wonderful friends here. You should tell me more about them.”
“Yes, Mom,” Ludo began hesitantly. “Don, Johanna, and her sister Mauranne are really great friends. They help me a lot.”
His mother smiled warmly. “That’s wonderful to hear, Ludo. How do they help you?”
Ludo took a deep breath. “Well, sometimes I can be really forgetful and a bit, um, dummy. Like the other day, I couldn’t find my homework, and Don helped me look for it. It turned out I had left it in my locker. I felt so silly.”
Don chuckled, playing along. “Yeah, Ludo tends to be a bit absent-minded sometimes, but we're happy to always check on him.”

Ludo’s mother nodded approvingly. “That’s very kind of you, Don.”
Ludo continued, “And Johanna and Mauranne are always reminding me to stay organized. I’m really bad at keeping track of my things. Like, there was this one time when I forgot my lunch at home, and Mauranne shared hers with me. She even helped me pack my bag properly after that.”
Johanna chimed in, “Ludo’s got a big heart, but he just needs a bit of guidance to stay on track. We’re happy to help.”
His mother looked touched. “You all seem like such good friends. I’m glad Ludo has you.”
Ludo felt his cheeks burning but knew he had to keep going. “They also help me with my social skills. Sometimes I can be really shy and unsure of what to say. They teach me how to be more confident.”
Johanna smiled sweetly. “Ludo just needs a little push sometimes, and we’re here to support him.”

Ludo’s mother beamed with pride. “It’s wonderful that you have such caring friends, Ludo. It sounds like they really look out for you.”
Ludo forced a smile. “Yes, Mom. They really do.”
Throughout dinner, Ludo continued to compliment his friends, weaving in examples of his so-called clumsiness and forgetfulness. Every time he spoke, Don and Johanna would nod approvingly, encouraging him to keep going. His mother seemed genuinely touched by the camaraderie and support she perceived among them.

After dinner, when they returned to Ludo's room, the atmosphere changed. Don closed the door behind them, and the three turned to face Ludo.
“Now, Ludo,” he said, arms crossed, “how many times did you call us by our first names without titles tonight?”
“Ten times, Mister Don,” Ludo admitted, lowering his head.
“That's ten punishments, then. And since you forgot to thank us for staying for diner, we'll add another,” Don said sternly.
Ludo felt his face burn with shame as he knelt before Don. “Thank you, Mister Don. I'm sorry for my faults,” he said.
“Good girl,” Don replied. “Now, let’s start with those punishments.”
They gave him to write “I must always show respect to Mister Don, Miss Johanna, and Miss Mauranne” 100 times. The punishment had to be finished by the next morning.
He also had to write apology notes to each of his master and mistresses. “Make sure you express how grateful you are for our guidance,” Johanna instructed.
Johanna pointed to a corner of the room. “When you will be done with you lines and letters, you will stand there for 30 minutes without moving.”
They also told him that the next day he would have to tuck his shirt into his panties and let the elastic stick out of his pants to be visible. “It's hardly a punishment,” said Johanna, “after all you should be proud to show off your pretty little girl's underwear to everyone!”
He should also wear his bracelets and anklets again to school.
But first, “You need to recite 'I am a silly little girl who needs to learn her place' 50 times, and make sure you sound sincere,” Don said.
Ludo kneeling, bowed his head. “Thank you, Mister Don and Miss Johanna, for your guidance and for helping me learn my place,” he said, his voice filled with deference.
Don patted his head. “Good girl. Now you can go to work. We see you tomorrow!”
Ludo nodded, feeling utterly humiliated but knowing he had to show his appreciation. “Yes, Mister Don. Thank you,” he whispered before they leave the room.
Ludo diligently did his punishments, even those that Don and Johanna could not verify. He went to bed late and was stressed for the next day. But he had to obey whatever it cost.

[sissy29000]

Chapter 31: Becoming Visible

One morning, as Ludo opened his locker, he found a small bottle of transparent nail polish inside.
Nervously, he took the bottle and applied the nail polish to his nails. The polish was nearly invisible, but Ludo felt incredibly self-conscious, imagining that everyone would notice.
All day, Ludo was on edge. He constantly glanced at his nails, worried that someone would notice the slight sheen. He kept his hands hidden as much as possible, shoving them in his pockets or clasping them behind his back. Every time he interacted with someone, he felt a rush of anxiety, convinced that they would see and comment on his nails.

During the last period of the day, Ludo was in math class. As the teacher wrote equations on the board, Ludo's mind wandered. He absentmindedly tapped his fingers on the desk, and the girl next to him noticed.
“Hey, do you have nail polish on?” she whispered, her eyes narrowing as she examined his nails.
Ludo's heart pounded. “Uh, no, it's just... a trick of the light,” he stammered, pulling his hands away.
The girl shrugged, but Ludo's panic surged. He couldn't wait for the day to end.
When the final bell rang, he quickly gathered his things and headed for the exit. As he walked through the hallway, he felt a tap on his shoulder. He turned to see Mauranne, Johanna, and Don standing there.
“How was your day, Ludo?” Johanna asked, her eyes twinkling with mischief.
Ludo hesitated. “It was... fine, Miss Johanna,” he said.
Don stepped closer and grabbed his hand, examining his nails. “Nice polish,” he said with a smirk. “Looks like you followed instructions.”
Ludo felt embarrassment, but also a strange sense of pride for complying with his master and mistresses.
He quickly curtseyed, lowering his head. “Thank you for your guidance, Mr. Don. I appreciate the compliment on my nails,” he said, his voice full of genuine gratitude.

Over the next few days, he continued to wear the transparent nail polish. Until he found another surprise in his locker. This time, it was a small tube of lip balm. The nail polish had been hard enough, but now he had to add a glossy sheen to his lips. He sighed, knowing there was no way around it.
In the bathroom, Ludo cautiously applied the light pink balm that made his lips glisten. He examined his reflection in the mirror with dread. The shine was subtle but noticeable if someone looked closely.
All day, he was hyper-aware of his lips. He constantly licked them, trying to reduce the shine, but it only seemed to make it worse. He kept his head down, avoiding eye contact and hoping no one would notice.

During lunch, Mauranne approached Ludo again. “How are you feeling today, Ludo?” she asked, her tone sweet but with a hint of mockery.
Ludo bowed his head slightly and curtseyed. “I'm fine, Miss Mauranne. Thank you for asking,” he replied, his voice full of forced cheerfulness.
Mauranne tilted her head, examining his lips. “Your lips look lovely today,” she said, a sly smile playing on her face.
Ludo blushed deeply. “Thank you, Miss Mauranne. I appreciate the compliment.”

Later in the day, Ludo had a class with both Don and Johanna. During a break, Don approached him, scrutinizing his appearance. “Let's see those lips, Ludo,” he said, lifting Ludo's chin.
Ludo obediently puckered his lips slightly, showing off the glossy balm. Don smirked. “Good job, Ludo. You're learning to follow instructions well.“
Ludo curtseyed deeply. “Thank you, Mr. Don, for your kind words,” he said, his heart racing.
Johanna joined them, her eyes sparkling with amusement. “It suits you, Ludo. You look pretty,” she teased.
Ludo's face burned with embarrassment, but he managed a small smile. “Thank you, Miss Johanna. I'm glad you think so,” he replied, curtseying again.

That evening, Ludo was in his room, applying a fresh coat of the lip balm as instructed. He knew that one of his masters or mistresses might check on him at any moment. His phone buzzed with a message from Don: “How are your lips looking, Ludo?“
Ludo quickly snapped a selfie, making sure his lips were clearly visible, and sent it back. “Shiny and pretty, Mr. Don. Thank you for checking,” he wrote with compliance.

The next morning, Ludo found a new lipstick tube. This one was even glossier and had a faint pink tint.
Over the next few weeks, Ludo's transformation became more pronounced. The once subtle changes gradually gave way to more overt feminization.

And then one day Johanna handed Ludo a small piece of lace one day after school.
“Ludo, you'going to sew this lace onto the collar of your shirt. It will look cute.”
“Of course, Miss Johanna,” Ludo replied, his hands trembling slightly as he took the lace. “Thank you for the opportunity.”
That evening, Ludo sat at his desk, carefully sewing the lace onto his shirt collar. The delicate work required patience, and he knew Johanna and Mauranne expected nothing less than perfection.
As days passed, Johanna and Mauranne added more demands. They handed him ribbons and small bows, instructing him to attach them to various parts of his clothing.

“Ludo, add these pink ribbons to your shoelaces. It’s a subtle touch, but it will make a difference.”
“Yes, Miss Mauranne. I'll do that right away. Thank you for guiding me,” Ludo responded, his voice steady despite the nervous flutter in his stomach.
Ludo spent his evenings meticulously adding these feminine touches to his wardrobe. He sewed small bows onto his socks and attached delicate lace trim to the cuffs of his sleeves.
As the weeks went by, his classmates began to notice the changes. The lace on his collar, the ribbons on his shoelaces, and the bows on his socks did not go unnoticed.
“Hey, Ludo, what's up with your clothes? Did you lose a bet or something?” a classmate teased, pointing at the lace on his collar.
“No, I just... I like them this way,” Ludo stammered, trying to hide his embarrassment.

Johanna and Mauranne grew bolder with their demands. They handed Ludo a small, delicate brooch shaped like a butterfly.
“Pin this to your jacket, Ludo. It's a lovely addition.”
“Yes, Miss Johanna. Thank you for trusting me with this,” Ludo said, bowing his head slightly in deference.
He pinned the brooch to his jacket, feeling the weight of each new accessory as it added to his transformation. The gradual changes in his appearance were now undeniable, and Ludo found himself constantly aware of the feminizing touches adorning his clothes.

[sissy29000]

Chapter 32: More And More Tormentors

On a sunny afternoon, as Ludo was leaving school, he saw Mauranne waiting with her friends near the school gates.
“Good afternoon, Miss Mauranne,” Ludo said, bowing deeply and giving a courteous curtsey. “I hope you are having a wonderful day.”
Mauranne’s friends exchanged amused glances, clearly intrigued by Ludo’s formal greeting. Mauranne smiled, clearly enjoying the attention. “Thank you, Ludo. You’re looking as charming as ever. My friends and I have planned a little outing. Would you like to join us?”
Ludo, knowing he had little choice but to comply, replied, “I’d be delighted to, Miss Mauranne.”

Ludo followed them to the park, where the girls had planned a series of playful activities. They first had him participate in a game of “pretend prince.” Mauranne and her friends took turns issuing royal commands, and Ludo dutifully followed, performing exaggerated bows and curtseys.
“Ludo,” Mauranne said with a grin, “please fetch us drinks from the park’s vending machine.”
“Of course, Miss Mauranne,” Ludo replied, hurrying off to get the drinks. He returned with the cans, giving another deep curtsey as he handed them out.

Next, Mauranne and her friends set up an impromptu obstacle course, complete with hula hoops and cones. “Time for the obstacle course,” Mauranne declared. “Show us your agility, Ludo!”
Ludo navigated the course, weaving through the cones and hopping through the hula hoops. The girls cheered and laughed, taking pictures of him as he completed each challenge.
After the obstacle course, Mauranne’s friends decided it was time for a bit of pampering. They had Ludo sit on a picnic blanket while they gave him a “makeover.” They applied bright, playful makeup to his face, added temporary glitter tattoos, and styled his hair with colorful clips.
Mauranne watched with satisfaction, clearly enjoying her role in directing the fun. “Thank you for my makeover, Miss Mauranne. Thank you for including me in your fun,” he said curtsying.
He ran home to wash himself before his Mom came home, and hoping not to meet too many people on the way.

On the way, he was stopped by a bunch of young children. “Hey! That’s him I was talking to you about, look at him, he looks like a girl!”, a girl shouted.
They circled around him. They were giggling and whispering to each other, pointing at him with curiosity and amusement.
“Are you a girl or a boy,” a boy asked.
“I’m a boy,” Ludo said, lowering his head.
“You look like a girl to me!”, the boy laughed.
“Is it true that you let them boss you around?” one of the younger boys asked, barely able to contain his laughter.
Ludo, feeling a flush of embarrassment, tried to ignore them. But his silence only fueled their boldness.
“Why do you let them do that to you?” a little girl chimed in, her voice high-pitched and mocking.
As Ludo remained silent, the teasing escalated. They started calling him names, mocking his obedience to his masters and mistresses.
“You're like a big baby!” another boy taunted, “You do whatever they say!”
Ludo felt the sting of their words but knew he had to endure it. He had been conditioned to accept humiliation, and this was no different, even if it came from much younger kids.
“Do you cry when they tell you off?” one of the girls asked, her tone dripping with sarcasm.

Ludo's eyes began to well up with tears, much to the delight of the kids. Seeing his emotional reaction, they pressed on, their taunts becoming more relentless.
“Look! He's going to cry!” they jeered, pointing and laughing at his teary eyes.
Ludo tried to hold back the tears, but the combination of their mocking voices and the sheer humiliation overwhelmed him. A tear rolled down his cheek, followed by another. The younger children, seeing their power over him, continued their teasing with renewed vigor.
“Crybaby! Crybaby!” they chanted, dancing around him in a cruel circle.

Ludo felt utterly defeated. The tears flowed freely now, and he sobbed openly, which only seemed to entertain them more.
In a desperate attempt to make the teasing stop, he lowered himself even further. He looked up at the children through his tears and begged, “Please, please stop. I can't take it anymore.”
But his plea fell on deaf ears. Instead, they mimicked his begging voice, adding to his humiliation.
“Please, please stop,” they echoed mockingly, laughing as they did so.
Ludo's sobbing became more intense, his body shaking with each sob. The younger children reveled in their power over him, enjoying the spectacle they had created.

[sissy29000]

Chapter 33: Opening Up To Mummy

Ludo’s mother noticed the changes subtle feminine touches in his clothing, but also that his movements were more delicate, his demeanor softer. She had suspected something for a while but hadn't confronted him about it.
Ludo had started doing the laundry himself so that she wouldn't notice the absence of his boy underwear and the presence of his panties, but she ended up opening his drawer one day and realizing that he only owns ultra-girly underwear.

“Ludo, can we talk for a minute?” she asked gently as she sat down on the sofa.
Ludo hesitated but then nodded, sitting down across from her. “Sure, Mom.”
She looked at him, her eyes filled with concern and curiosity. “I've noticed you've been dressing differently and acting... well, more feminine. And then I saw your new underwear. Is there something you would like to talk to me about?”
Ludo took a deep breath, knowing this was a pivotal moment. “Mom, it's a bit complicated, but I'll try to explain. I guess it all started when I realized I didn't feel like I measured up to other boys. They were always stronger, more confident, and more assertive. I always felt... out of place.”
His mother listened intently, nodding for him to continue.
“I started to feel comfortable when I was around girls, especially Johanna and Mauranne. They didn’t judge me. Instead, they helped me dressing up for fun. And for some reason, it felt... right.”

His mother’s expression softened. “But why girls' clothes, Ludo?“
Ludo blushed but pressed on. “When I started wearing girls' clothes, it was like I found a part of myself that had been missing. The fabrics, the colors, the styles – they all felt more me than any boy's clothes ever did. And it wasn’t just about the clothes. It was about the way they made me feel. Wearing them made me feel cared for and special.”
He paused, gathering his thoughts. “And... Johanna and Mauranne, they started giving me small tasks and orders, Obeying them made me feel useful and accepted in a way I hadn't felt before.”
“Orders?”, his Mom asked intrigued.
“Yes... I know it sounds strange, but taking orders, even humiliating ones, gives me a sense of purpose. It takes away the pressure of trying to fit into a mold that I never could. When I obey, I feel like I’m doing something right, even if it's embarrassing. It feels like my natural place.”
He hesitated before continuing, his voice dropping to a whisper. “I know this might sound pathetic, but I feel that it’s normal for me to obey them, no matter what. And not just them – anyone who’s more assertive than me. I think others have every right over me because of that.”

His mother took his hand, squeezing it gently. “It’s true that you’ve always had a side… How should I put it… A kind of wimp and crybaby,” she said thinking out loud. “But do they treat you well?”
“Yes, they are demanding and they make me understand my place, whether it's Miss Johanna, Miss Mauranne or Mr. Don.”
His Mom frowned upon hearing such formal names.
“But they sometimes treat me like their little sister, like a little baby, and it’s very nice when they give me affection,” he continued to confess.
Ludo smiled, a tear slipping down his cheek. “It makes me feel safe, Mom. When I’m pampered and treated like a little girl, I don’t have to worry about being good enough. I can just be. I know it’s weird, but it makes me feel loved and protected in a way I can’t explain.”
She nodded, understanding dawning in her eyes. “Ludo, I love you no matter what. If this is who you are and what makes you happy, then we'll figure it out together.”

Ludo felt a weight lift off his shoulders. “Thank you, Mummy. I was so scared to tell you, but I feel better now.”
She ignored him using the childish term and pulled him into a hug, holding him tightly.

[sissy29000]

Chapter 34: Opening Up To The World

One day, during a school assembly, Ludo was called to the front by his teacher. His classmates and teachers noticed the not so subtle makeup on his face, the pink nail polish, and the barrettes in his hair. The whispers and giggles were almost deafening, but Ludo stood tall.
“Ludo has something he wants to share with all of us,” a teacher announced.
Ludo took a deep breath, feeling his heart pound in his chest. He looked out at the sea of faces, including his Mom who had been invited by the school.
“I... I like being feminine,” Ludo said, his voice trembling but gaining strength with each word. “I like wearing makeup, and nail polish, and feminine clothes. This was my choice, and I'm happy this way.”
There were gasps and murmurs from the crowd.

In the weeks, his nail polish turned a brighter shade of pink. Barrettes decorated his hair, holding back the growing strands that framed his face. He wore girl's t-shirts and tights under his shorts. Ballet flats replaced his sneakers.
At the request of his master and mistresses, he began to remove his entire hair very frequently to have smooth baby skin.
Of course, Ludo faced teasing and mockery, but he also found a strange sense of liberation.

There was no longer any question of blackmail into revealing his embarrassing photos and videos. The whole world must now know Ludo's true nature. Either way, it was obvious to Don, Johanna, and Mauranne that the images were just a pretext and that Ludo was a willing participant in the domination relationship he was in.
In private sessions with Don, Johanna, and Mauranne, Ludo confessed everything. One evening, as they sat in Mauranne's living room, Ludo kneeling before, he even admitted that forgetting his swimsuit the very first time was on purpose. Johanna laughed and said she knew it all along, she had immediately noticed how mesmerized he was by the ultra feminine swimsuit.

After this confession Johanna and Mauranne dressed him in a beautiful pink dress, complete with lace and ribbons. His hair was styled, and his makeup was done to perfection.
“You look lovely,” Johanna said, adjusting a ribbon in Ludo's hair.
“Thank you, Miss Johanna,” Ludo replied, curtseying. “I appreciate everything you've done for me.”

[Sandra B]

Love the meticulously-described gradations of feminization.  Where can it go from here?