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Sasha Sucklove's Sissy School

Story Info
A look into the USA's premier sissy school.
6.8k words
4.59
21.7k
40

Part 1 of the 2 part series

Updated 12/20/2024
Created 11/15/2024
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This is the complete story of Adam's first day at Sasha Sucklove's. We'll be regularly checking in with him (soon to be her) and his classmates here. Now that the school, classes and characters have been established, I'm going to be posting the story in longer chunks, similar in size to this omnibus rather than the bite sized installments I've been posting so far. I'll also be doing some spin-offs and new stories.

—-------------------------------------------------------

The light came and went, growing and dying as he faded in and out of consciousness. It was so disorienting and he felt so sick that he hardly took the time to notice what was going on around him. If he had, he would have noticed a line of tables, each one holding a male like himself. There were all shackled down, all knocked out by anesthetics. In the moments where his were weak enough to feel, he felt something in his arm, some ache or pain. There was also a numbness and a cold feeling between his legs. He almost thought that he saw something metal down there.

Finally, during one of these fleeting moments brought on by his higher than normal tolerance to the drugs, he noticed someone.

She was beautiful. Her dress was pink, frilly yet tight, showing off her immaculate curves and ample bosom. Her face was adorable, the kind that could make a man forget himself. Her nails were perfectly manicured with pink extensions, her heels were 6 inches high and her hair was a bright, dyed blonde. He felt an ache down below as his eyes traced their way down her body, the frame of this perfect woman.

Someone came up to her, an older man with a large frame. He wore a suit and seemed to be inspecting the boys as she minced over. Her every moment was swishly, limp wristed, feminine. Her heels clicked and clacked on the metal floor. Her hips swayed enticingly. Her hands were kept parallel to the floor, swinging gleefully as she made her way over to the man and as he put his arms around her.

"I always love inspecting the new bunch" he whispered in her ear, so close that it was clear they were something to each other.

"Me too" she replied in a high pitched tone, her voice so cutesy that it almost seemed fake.

"Oop, looks like one's awake" he smiled, looking directly at the boy with the moving eyes.

"Wondering what this is?" he asked, walking over and harshly flicking the metal cage around his member. "Well, that's just something we give all of our students before they officially join the school. Bri, show him yours."

The blonde smiled and moved her soft, slender hands to her dress, lifting it up. He saw her milky white legs, so supple and desirable. He saw her hips, so shapely, so suggestive. Her whole frame was perfection, the kind of dainty thing that would make pants tent just from the silhouette.

But within the shape of those hips was something like a pink metal thimble, one which looked similar to the cage that the boy was wearing. Below it were two balls, looking almost purple.

"Sweet dreams" said the man as he increased the dosage of the drip.

"Now" said the man, walking over to his sissy as the boy faded out of consciousness. "I'm feeling tired. Ready for bed?"

"Yes headmaster" said the sugary sweet voice. And all went black.

The first thing to make an impact on his blurry vision was the pink. He was slow to come out of whatever sleep they put him in, but even in his haze he could see the loud pink all around him. Everything was in a shade of it, save for those few items that contrasted it with clean, pure white. One such thing was his mattress, which he was slowly beginning to feel as the numbness left. Adam didn't remember much. There were some strange visions of a blonde girl, replaying in his head. Yet he wasn't sure where he was. All he knew, with the cold air on his body and a tightness down below, was that he was naked. He was naked, save for something metal between his legs.

He sat up slowly, looking around as his vision cleared and realizing he wasn't the only one here. There was another white bed in this pink nightmare, and another young man beginning to stir. He was naked as well, with only a pink metal cage on his penis, and a snug pink collar on his neck. Adam reached up to realize he wore one too, yet it was so well fit that he barely noticed it.

By the time he got to his feet, his roommate had started to wake, looking around in shock and horror as a voice filled the room.

"Hiya gals" came a giggly, high pitched voice over the intercom. Adam recognized it immediately. It was the girl he'd seen before.

"This is Bri, your senior class president at Sasha Sucklove's Sissy School. First off, I want to welcome the new batch of students and give them some explanations about all this. They are currently locked into teeny tiny clitty cages, and will remain so for the rest of their lives. Don't worry though girls, they won't always be this big and cumbersome. They'll get smaller as you progress. As for your collar, it has several features, most of which you won't have to worry your pretty little heads about. But when you're naughty little girls, they're likely to do this:"

Suddenly, Adam and his roommate screamed out in pain, both of them writhing in agony as Adam himself fell to the floor. It only lasted for a second or two, but it was the most painful second of Adam's life.

"So please, behave yourself. Our disciplinarians greatly enjoy using that function and are just waiting for you to test them" said the voice, with all the pep of an overeager cheerleader giving a speech at a rally.

"In one minute, your doors will open and you will walk along the pink link to the auditorium where your proper orientation will commence. All students who refuse to attend will be made to...with additional punishments allotted" she explained.

"That's all for the morning announcements. Have a glamorous day!"

The voice disappeared as Adam and the other boy looked to each other.

"Do you have any idea what's going on?" He asked, as Adam shook his head.

"You?"

The other boy did the same. They were both sitting in a way to hide their cages, clearly embarrassed to be naked and in such a state, even in this insane situation.

Adam looked around the room, seeing nothing that could help him in the stark space. There were dressers and vanities but neither had anything inside them. There weren't even sheets on the bed. "Maybe we can break the mirror and use the shards as a weapon?" He offered. In his head, he was counting to 60. They were almost halfway to the doors opening.

"Worth a shot" said his roommate, looking as Adam tried to figure it out. There was nothing to break it with and the vanity was bolted down. He'd have to wait until they were given something other than an empty room.

**BEEP**.

The door opened on its own, revealing a hallway with lights on the floor, leading down the corridor. Hands over his cage, Adam poked his head out and saw several other boys doing the same. Sure enough, there was a pink line lit on the floor.

At the end of the hall was an open door.

One of the boys immediately ran for it, sprinting until he reached a turn and went the wrong way. As soon as he got five feet away from the pink line, his screaming filled the halls.

The other boys simply watched as he dragged himself back to the line, body taut with pain. That's when Adam looked away and noticed that the far end of the pink line was closing. "Come on!" He urged his roommate, hurrying out and down the path as the line disappeared behind him. Almost all the other boys got the message and quickly moved, not wanting to be there when the line was gone. Soon enough there was a line of naked boys, holding their cages and hurrying down the hall.

Adam looked about, seeing nothing but nondescript rooms and doors until they finally reached the auditorium. It was a massive space with stadium seats and a stage at the bottom. Laid on every chair was a pair of panties.

"Ladies, ladies, we have a busy day. Let's not drag our feet" said a stern looking woman on the stage, watching them file in and take their seats. Adam sat next to his roommate, holding the panties.

Once everyone was seated, the woman at the podium began. "Very good. You've obeyed so far and your classmates who haven't are being dealt with" she smiled, showing off a sick glee as she spoke the last two words. "I'm sure you're all thinking the same thing...who's Sasha Sucklove?" She said, clearly enjoying her own joke as the boys looked to each other. That was the last question on their minds.

"Sasha was the first student I ever had, back before this was even a school. To tell you her story, I first have to tell you the story of Henry Mars."

The screen behind her lit up with the image of a somewhat nerdy looking young man. "He was the stepson of a friend of mine, and an unwanted stepson at that. Her husband was one of the richest men in America and well, let's just say she had her ways of taking advantage. Henry, as it turned out, was too clever for his own good-"

"Why are we here you b-" began a young man in the back, before howling in pain.

"Keep in mind that I can do that to any of you, or all of you, at any time" she tssked. "As I was saying, Henry was too clever for his own good. He uncovered her past, her path of former husband's and the ways in which she squeezed them dry. But he wasn't clever enough to contact the police before confronting her, and so she called me. One rather simple kidnapping later and he was in my basement."

The boys looked in horror at this mad woman, several either trying to speak up or run and all meeting the same fate on the floor.

"My friend had taken on several names and identities in her scams but she was currently posing as a blonde bimbo, and wanted to teach her stepson a lesson after all his criticism towards her. So I began what would become my patented feminization process and well..." she chuckled, the screen shifting to reveal a woman posing for a photoshoot that wouldn't be out of place in playboy. She was gorgeous. She was voluptuous. She was making everyone strain in their cages.

And then, as the next slide revealed, she was wearing a cage. It was similar to the ones the boys were wearing but completely flat.

Several others tried to resist or start a riot, only to end up shouting in pain.

"In gratitude" said the woman, over all the commotion, "My friend gave me the seed money I needed to start this institute. "And I named it after her new daughter, the first sissy I molded.

Even Adam, though trying to keep a cool head, was starting to panic. He stood up from his chair as his roommate did the same, and as the headmistress rolled her eyes. They had a full on revolt on their hands. But all orientations ended like this.

"You will wake up with your class schedules and new names on your door. Also, for those of you who haven't caused trouble, you will receive your means of reward."

And just like that, every boy felt a prick in their necks on the inside of their collar, as blackness once more overtook them and as they fell unconscious.

Once more, Adam woke up in the pink room.

He wasn't sure how much time had passed, whether it was a new day or a few moments later. He hadn't seen widows anywhere in the whole complex, so there was no way of telling. He was still naked, only he was now laying atop what seemed to be silk sheets. And as he shifted, he noticed something else was different.

It wasn't just the cage that was waiting down below. When he changed positions on the bed...something changed positions inside of him. Something was inside of him. He yelped and stood up, feeling it pressing against his insides as he made his way to the mirror.

It was a plug.

He tried to get it out but it was just too big. He guessed from the keyhole at its base that it couldn't be minimized and removed without some staff member's help. He also guessed that none would be in the mood to help him.

His roommate turned to him as he stood, letting him see for himself before clearing his throat. It seemed like he'd been awake a bit longer. He was currently looking at the door, which had two names printed on it in bright pink cursive.

"Eve" and "Cindy."

"They have some sense of humor" muttered Adam.

His roommate raised an eyebrow. "Huh?"

"Calling me Eve. My real name is-"

He didn't get a chance to say it before screaming in agony, beating himself on the bed frame for support. His roommate watched in confusion, before suddenly realizing what must have happened.

"My name is-"

He crumbled to the ground just the same.

Both of them panted, slowly lifting themselves to their feet as they realized what was going on. They weren't allowed to say their names anymore.

Adam looked to the name on the door and then noticed the two new items that had been laid out at the foot of the bed. The first was a pink and white sheet of paper, with some sort of schedule on it. The second was a pink tee shirt and skirt.

"No judgement if you put it on" said Cindy as he picked up his clothes. "I figure it's better than being naked."

Adam nodded and slowly dressed, looking at the schedule as he did.

Eve Elegance. First Year.

First Period: Deportment

Second Period: Gym

Third Period: Anatomy

Fourth Period: Lunch

Fifth Period: Fashion

Sixth Period: Check Up

There were only six periods but they were each an hour and a half long, save for lunch. The doors unlocked as he read it, wondering what the heck Deportment and Check Up were. It seemed like he was going to find out though. Best to figure this place out as much as possible before trying to make waves.

"Let's go" said Cindy, putting on his clothes and heading for the door. There were signs lit up on the floor to guide everyone to their classes, though it seemed a few kids were missing from the amount that was here to start. Adam hurried out bare foot, feeling the cool air drafting up his skirt as he went off to Deportment.

The deportment classroom was occupied by about thirty other boys, all looking uneasy as they found a pair of small, two inch heels at their desks. Adam found his, marked with the name Eve, just as the teacher entered.

"Hello ladies" smirked the woman, a rather voluptuous babe in her early 40s, sporting jet black hair and a sinister smile.

"Where the heck is my roommate?!" Demanded one of the boys, only to fall to the ground in terrible pain.

"Great question" said the teacher, as though she hadn't just punished him for asking it. "Some of the girls who were most unruly during welcome and orientation have been put into remedial classes. That's all you need to know. Now..."

She went over to the board and wrote out "Mistress Rachel."

"Each of you has shoes. Put them on."

Most of the boys knew better than to argue, but a few stood defiant. Adam wasn't one of them.

"I see..." said Mistress Rachel with a shrug, watching as the boys stood there in growing discomfort. Adam didn't know what was up until they yelped and jumped onto their desks, only to find that just as painful.

Bending over, Adam touched the floor, only to feel it start to burn his finger. Not wanting their feet to get scorched, the rest of the boys put on their heels.

"Very good. This class is deportment: the art of movement. So help me, I will train away every masculine mannerism you have. I will correct away your boyishness, reeducate you on your every instinct and replace it all with proper womanhood. Heels, obviously, are an important part of that. I will be locking those onto your feet before you go and every week, they will go up an inch. First lesson. Sit."

The boys all looked to each other as she rolled her eyes. "Sit. Now!"

They quickly obeyed, glad to find that their metal chairs had cooled down. But obviously, they didn't know how to sit in skirts. None smoothed them. None sat properly. Some even manspread. Most of all, they found it strange to sit with the plugs, trying to keep their weight off them and pretend they weren't there.

Mistress Rachel walked up to Adam and smiled. "Try again."

He was a bit confused but stood up and tried to sit again.

SMACK

She hit him hard across the face. "You're wearing a skirt!" She reminded him, before instructing him in how girls in skirts were supposed to sit. "Now try again and if you disappoint me, you get the collar!"

He nodded and tried his best to follow her instructions, nearly shaking with fear. But she seemed mostly content with it. "Good. Now girls, do the same."

The next hour consisted of Mistress Rachel making them sit properly, over and over. She was a stickler for perfection and the more they practiced, the more comfortable she seemed punishing them for the smallest error. She even zapped a boy with his collar because he burped. By the end of class, she was beaming with delight and most of the boys were sick with pain. She took the pleasure of going to each and every one and locking on their heels before they left, snickering as she did.

"Not bad for a first day. Tomorrow we continue making proper ladies out of you" she said, ushering them out of the class. Adam had trouble walking but he hurried as fast as he could, taking his heels on to Gym.

The pink directions on the floor led Adam to Gym, even if his pace was slow. The heels were bad enough, even if they were only meant to be a prelude for what was coming. But what really made it hard was the pain from his last class, which had coalesced into a sore and nauseous feeling. He tried to feel better by the time he arrived, but there just wasn't much he could do. Luckily, there wasn't a need to change. The students were ushered past the locker room and right into the large gymnasium where the teacher was waiting.

This one was another woman, though markedly different from Mistress Rachel. She was an Amazonian type, standing taller than most of them and showing off her abs as she waited. Her muscles rippled in her sports bra and yoga pants, and some of the boys were already staring. She scoffed and approached one.

"Don't worry, I'm not going to turn out to be another sissy. We like pulling that rug out from under you but I'm all woman. And no sissy would ever look like this" she bragged, flexing her arm. "So no problem staring, right?"

The boy sheepishly nodded, looking more than a bit nervous. Before he could add anything else, however, she had him in a headlock.

"Wrong! Women are your superiors! And it's your job to be objectified. Not theirs. Understand?"

He whimpered. "Yes..."

She let go and slapped him hard across the face. "Yes, Mistress Amy!"

"Yes, Mistress Amy" he repeated.

"Good. So you girls can learn. First thing's first: you aren't getting muscles. Ever. You aren't lifting. You aren't making yourself stronger. This class is about getting you in feminine shape. So squats. Yoga. Flexibility. Understood?"

The boys meekly nodded.

"Good. And if you don't, I have a demonstration ready for you."

With that she clapped her hands, and a giggling figure came prancing in from one of the doors. She moved like each step made her giddy, so much pep and energy as she practically skipped next to the teacher. It was Bri, the Senior Class present. She was wearing a pink sports bra that was making more than a few cages very tight. It didn't matter that she was a sissy. She was the most perfect, most feminine thing they'd ever seen. Most girls couldn't even dream of approaching her levels of girlish beauty. Her bottoms were matching pink shorts, tight as can be and extending to her midthigh. To anyone who could get a glimpse, they made her cherrybomb of a booty look absolutely irresistible. It was only then, during his second encounter, that Adam realized she had no blemishes. No birthmarks, no scars, nothing at all except for the most supple, milky white skin he had ever seen.

12


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