Sissy School - Chapter 6 - The Sorting

Like a toddler on a trip to Disney World, I was stuffed in a 1950’s style stroller and led into the gigantic castle. The difference being that most kids would kill to go to Disney World, as i’m sure most of the sissies like Bryan would too. But not me. I had already felt like i‘d been in a bad dream, and being driven into the doors of the castle by a giant black man only emphasized that my nightmare was no where close to ending. 

There were sissies and Bouncers everywhere as we entered the castle. Penis-shaped candles and torches illuminating the inside. 

Sitters were filing the students into the Great Hall. “Come on second years!” They shouted “you know the drill! You’ve already been sorted! Meet up with the other upper classmen! Unless you’d like to go join the first years and wear Pampers again! Cause that can certainly be arranged!!”

Tyrone steered the stroller around to the side entrance, where we met the other line of first years. Bouncers helped the sissy babies out of their carts and stood them up in a line. Tyrone lifted me out with no issue as if I were a small child and plopped me on my feet. 

“Good luck, sissy!“ he winked with his baritone voice. Turning the carriage around and walking off. 

I watched him fade away into the darkness of the hallway when a loud applause erupted from inside the great hall. 

I was just at the edge of the door in line, and had just enough room to peek inside. 

There were four extremely long tables taking up almost the entirety of the room. The benches of the tables filled with sissies. All of them looking much more feminine compared to the group standing around me. Us first years looked like a bunch of middle-aged dudes who lost a fantasy football bet and had to stuff ourselves in dresses as a humiliating punishment. 

At the forefront of the Hall was a stage where I assume the Professors sat. The applause had sounded as a particularly powerful looking woman approached the stand. She looked like a stereotypical sexy librarian you would see out of a cheesy porno. Her dark hair was pulled tightly into a bun. Her half moon spectacles with a chain dangling from them. A tight, firm set jaw with sharply pursed mouth of fiery red lipstick. 

“Hello all,” she said, and the room went instantly silent. “And welcome, to another year at the Sissy School for Male Whores and Adulterers!“ there was a very high pitched squeal of applause. Again silenced as soon as the woman made another move to speak “As you all know, I am your Headmistress Eleanor Rosebelt. I take great pride at taking you pitiful excuses for men, and harnessing your true potential. Your potential to be a dirty, cocksucking sissy gurl!”

Again a round of applause from the upperclassmen. Did they really like to be spoken to in that way? Or were they just applauding out of fear of this scary looking woman?

”On your journey to becoming a full, prissified sissy bimbo, you will spend your time in one of the four Houses: The Maidenlaw house is for those who seek to serve in the home as a caretaker to their owners every need. They pride themselves on keeping a clean house, and a well fed, and sexually satisfied Master or Mistress.“

One of the tables erupted in cheers at the mention of their House name. I noticed most of them were dressed in outfits that had more black accents or fringe. 

“The Mufflefluff House is the backbone of the porn industry. As you all know, almost 33% of the countries GDP now comes from the...erotic side of the internet. And the Mufflefluffs are the ones behind the scenes making sure those cocks are hard and ready to go. There is also a growing demand for T-girls, Traps, Trannies, and other fetishes i’m sure you all perused back in your formative years.  Those in the Mufflefluff house must be prone to high levels of humiliation and degradation, and have very little values and morals. There are a lot of fetishes out there, and you Mufflefluffs will fill those voids for all!”

Another round of applause, this time from the table dressed in mostly yellow frillies. 

“And where would we be without the Whoridor house?!” The pink table exploded. “Yes, you gurls are the ones most people get to see...and use. You’re the ones working the corners, the back alleys and —if you’re lucky—the Brothels. You’re the ones who give those sleezy men you all used to be a chance! How else are those pigs and virgins going to get their dick wet if not but in your mouth? Remember the days when psychopaths used to use and abuse poor innocent females? Well not anymore! Because now they have you! The Whoridors!”

My heart sank as she spoke. I couldn’t imagine living the rest of my life on my knees in some back alley sucking on some stranger’s cock. Or hiking up my skirt as a creepy old man rammed me from behind over the hood of his car. I did not sign up for this...

”And last but not least” continued the Headmistress, “We have the adorable Sluttykins!” The last table cheered. Their colors a lavender purple. I could see Graco in front of me nodding and smirking to his cronies, pointing to himself confidently as if he already knew that’s where he’ll be. 

“A Sluttykin sets their own path after graduation. They can choose to live a life of freedom in the outside world, or a life as a trophy wife for a lucky bachelor. No matter where they go, they will always honor our school, as a sissy or a newly remediated male. “

There was a gasp from all the first years. With whispers of “you mean I could look like a boy again?!”

I knew right then that was the House I wanted to be, but the idea was further cemented when the Headmistress said: 

“Now, as you all know, we will be competing  in our annual House Cup. The House with the highest points at the end of the year will get to spend the next term entirely out of chastity.  Because the Sluttykins won the previous term, they all — including those sorted into them tonight — get to go free from the bonds of chastity, unless otherwise instructed by staff.“

There was a buzz in the room now. Every first year wanting to join the Sluttykins. Every upperclassmen of the Sluttykins jealous of their freedom. A short cough by the Headmistress silenced them immediately. 

“And so, without further adieu, Professor Mars shall conduct the Sorting!” Everyone clapped as the Headmistress took the throne behind her and was replaced on stage by a beautiful looking young woman carrying a small pointing stick. 

“Come” she snapped at the first year in the front of the line. Pointing to the floor in front of her, indicating for the sissy to get down on her knees. The sissy obeyed obediently. Quivering from a mixture of fear, humiliation, and the feeling of a thousand pairs of eyes watching. 

Professor Mars began inspecting the sissy as if he were a breed in a dog show. ”Hmmm...a slender back and hips.“ she spoke out loud as if to herself. “Poor posture, but that can be corrected. Not a bad face...but not great either.” She grasped the sissy by the jaw and stuck a long slender finger in his mouth, swirling it around. “Not too large of teeth, but an extremely sensitive gag reflex...what's your name Sissy?"

"Chr-Christopher, Miss.." the sissy replied.

"Ohh well you will be going by 'Christie' from now on! And you will be doing it in your new House: MAIDENLAW!!” She shouted. The black tinted table erupted in applause. Welcoming their newest member to the table as he meandered his way over. 

The next sissy had unsightly moles on his face, his teeth were large and raggidy. Professor Mars took one look at him and hollered out “MUFFLEFLUFF” before he even knelt down. Apparently she thought he would be more suited for behind the scenes work or as a phone sex operator. 

Graco, Bert and Gurney were the next three up. Each one sent to Sluttykins. Smiling triumphantly as they joined the others at the table. Bert and Gurney apparently had tooblarge of a frame to be desirable in any of the other Houses, “and that’s something no amount of training can fix” Ms. Mars said. 

Next up was Bryan. Who noticeably tried to change to a slower pace when he realized he was skipping over to be inspected. After getting him on all fours Professor Mars smiled at his enthusiasm. “Ohhh we got an excited one here!“ she laughed. There was a scattered chuckle from around the Hall. Even from behind I could tell Bryan’s face had turned red with shame like it did earlier on the train. 

After inspecting his mouth, Ms. Mars hiked up his frilly skirt and reached into Bryan’s diaper with her saliva-lubed finger. “Quite the loosey goosey aren’t we?!” She teased after apparently entering his hole. She moved her hand to the front of his diaper, still keeping it inside. “And a sticky wittle mess inside to boot! I think someone‘s a perfect fit to be a wittle Whoridor!!”

Despite being a tad embarrassed. Bryan grinned with glee as he made his way to join all the pink sissies. 

The next 10 or so first years were pretty evenly distributed between the four houses. With some taking a while to be inspected, and others being sorted almost immediately. Some even had requests. Actually wanting to be a Maid or a Camwhore for the rest of their life. And Ms. Mars honored every one of them. 

By the time it was my turn, the pit in my stomach had grown to feel like the size of a watermelon. I approached the center of the stage hesitantly. Feeling everyone‘s eyes upon me, including those of the Headmistress and the Inspector. 

I knelt down in front of Professor Mars. Too nervous to move. 

“I see someone has already had some fun today!” She said, noting the dried cum stains still present on my face. “Open wide and say ‘ahhh’, dear!” She commanded. I obeyed, pretending I was at the doctor’s office. She stuck her finger into my mouth and swabbed the inside of my cheek. Then shoved her finger down my throat as if trying to force me to throw up...which I almost did. Gagging as soon has her finger met my uvula. 

“Weak gag reflex. A little soggy around the midsection. But a few weeks with Professor Michaels will get rid of that beer gut. Any requests, dear?”

”Sluttykins...” I tried to say, but it came out as a whisper. “Please! Let me be in Sluttykins!”

She was inspecting my ass now the way she did Bryan’s. Fingering my abused asshole that was still damaged from Tyrone that morning.

“Awww but a pretty gurl like you would make a great pornstar! You sure you don’t wanna be a Mufflefluff?!” She asked, still circling and inspecting me on all fours. 

“Please Miss...” I was begging now. Flashes of being condemned to a life of taking dicks bigger than Tyrone’s up my ass for the rest of my life going through my head. I started to cry “Please put me in Sluttykins...”

I wiped away one of my tears, not wanting the others to see. In doing so I bumped my bangs just enough to expose the dick-shaped mark on my forehead. That was my mistake. Professor Mars’ eyes grew as big as saucers. 

“The MARK!!” She gasped. Pulling my hair to the side roughly and forcing my head around for all to see. “He bears the Mark of the Chosen One!!”

The room filled with a murmur of whispers and gossip. Three sharp raps of the Headmistress’ cane on the ground ended that. 

“SILENCE! I have no time for such Fairy Tales!” She shouted. "In fact, this sissy shall henceforth be known as 'Fairie', as a reminder for believing in such nonsense!" Putting the legend to rest. But Professor Mars still seemed unconvinced. Looking at me as one would a Prophet or Alien. Her eyes still the size of saucers. 

“Please...” I said, attempting to change the subject and remind her of my desires. “Sluttykins...”

”Oh no no no no...” she whispered back so the Headmistress couldn’t hear. “A talent for making a man cum in 7 seconds would be wasted in Sluttykins. People will come far and wide to use you. They will pay enormous sums just for the chance. You’re going to be the greatest whore there ever was, and ever will be. And the only House to make you reach your true potential will be...WHORIDOR!!!”

The pink table erupted in hoots and hollers louder than ever before. And unlike with the other sissies, the other Houses groaned in disappointment. Not getting to say they shared a House with The Chosen One. 

Begrudgingly, I made my way over to the Whoridor table. Everyone smiling gleefully and eager to shake my hand as I passed. I only wished I shared their enthusiasm. 

I was led to the back of the long table where the other first years sat in oversized high chairs like giant babies. A Sitter opened up the tray of the chair next to Bryan. Closing and locking it shut once I sat. 

The rest of the Sorting was a blur. I barely even noticed Henry from the train get sorted into our House as well. Taking the seat next to me. I was too busy contemplating the life ahead me. Even though none of this still felt real, the terrifying images in my head did nothing to quell my sorrow. 

“Let the feast, begin!” called the Headmistress once everyone was seated. 

Suddenly plates and platters started appearing from nowhere. As leather and latex clad sissy servants brought out trays of food. I was starving, only having Cummy Bears and my wife’s lovers loads all day. 

The first thing I grabbed was a big steaming muffin. Iced and still hot from the oven. I took the biggest bite I could and was instantly filled with regret. The ‘icing’ tasted just like the bitter, salty taste of cum i’d come to learn so well that day. The muffin itself was still gooey, and was probably laced with copious amounts of cum as well. I instantly lost my appetite. Spewing out what was in my mouth all over my dress and onto the tray of the high chair. 

Bryan, however, couldn’t seem to shovel food into his mouth fast enough. Cakes, Mashed potatoes, mushy peas and carrots, some sort of pudding, all of it looking unappealing. But none of it could escape Bryan’s tiny baby-sized spoon. 

Henry looked over me and down the table at Bryan. Scoffing unapprobingly as he spooned a small portion of pureed prunes into his mouth, and wiping it daintily with his bib. 

”Having trouble little one?” Came a voice behind me. I turned to see a very pretty Sitter smiling behind me. It was she who was actually the little one. She couldn’t have been more than 5 feet tall, and had beautiful auburn hair down to her shoulders and black, horn-rimmed glasses. I twinged in pain as my cock tried to grow inside it’s tiny cage to no avail. I sat there dumbfounded. “Awww! You’re so cute!! My name’s Ariel. Does somewon need some help getting a wittle yum yum in their tum tum?!” She teased. 

“No...i’m fine, thanks.” I replied. Coming off very grumpy from being spoken to like a baby, and implying that I can’t feed myself. 

“Well you need to eat something Ms. Pissy Sissy! Here...” she grabbed a bowl off the table. “How bout some yummy cummy pudding?!” She grabbed my baby spoon off my tray and scooped up a huge helping of the white, creamy mixture. “Open uuppp wittle baby!!! Heeeeereee cumssss the airpwannnnne!!!” She cooed as she brought the spoon to my pursed lips. 

“I said ‘NO!’” I snapped. Slapping her hand away and sending the spoon flying. Her demeanor immediatey shifted from that of a loving mother/sister, to a stern, no-nonsense caregiver. 

“You will eat what I give you and you will like it!” her voice was low and menacing. “Otherwise I will —“

But we were interrupted by a ruckus across the table. Apparently another sissy baby wasn’t taking kindly to his food, and wasn’t liking being fed by a Sitter either. “You little TWERP!!” She shouted loud enough for the whole Hall to hear. Not bothering to restrain her voice the way Ariel did. The Sitter was much taller and ferocious looking than Ariel too. She had black hair snaking down her back in a long braid. Her nose was hooked and pointy. And her furrowing forehead wrinkled into the fiercest scowl i’d ever seen told me she meant business. She reached her hand up and snapped, looking out to the perimeter of the room. Immediately three large black Bouncers only slightly smaller than Tyrone swarmed around the sissy‘s high chair. 

One of them lifted the big baby out of his tray kicking and screaming. Then slammed him over the large table while the other two cleared the plates and held down his arms. The one who lifted him up was now fumbling with his belt buckle, dropping his pants to his ankles while the other men lifted the sissy’s skirt and ripped off his diaper, then began lubing his asshole. 

The sissy screamed, shouted and squirmed uncontrollably as the large man entered him from behind. Pounding him relentlessly while the Sitter watched triumphantly, arms crossed. The other sissies watched in horror as the gangrape took place only feet away from their dinner. I glanced over at the front of the Hall where the Professors were in order to see their reaction to the scene. They simply smirked and surveyed the rest of the crowd as if this were a very normal occurrence. 

After growing tired of his screams, one of the Bouncers pulled over a bowl of mushy peas, raised the sissy’s head up then plunged it down into the mush. Muffling the sissies screams into a low gurgle. After watching the sissy squirm in the green stew while getting fucked, Ariel turned back to me, smiled, and nodded. 

“Otherwise you might get that...” she finished. 

I didn’t dare protest as she brought the cummy pudding to my mouth again. 

Even though it still tasted like jizz, the first couple bites weren’t too bad. My stomach was gurgling in hunger, and the thick, slightly sweet creaminess helped to satisfy it. 

About half way through the bowl, I had had enough. But Ariel kept spooning it into my mouth. Catching any that leaked out expertly and putting it back in my mouth for another attempt at swallowing it. She noticed I was moving slower, so she picked up a baby bottle off the table and brought the nipple to my mouth. Or at least...what I thought was a nipple. Upon further examination it was actually a tiny rubber penis. 

“Drink up!” She said sweetly, yet firmly. I didn’t dare disobey. I sucked the tiny penis until the liquid inside was flowing. It tasted like a protein shake, but with a lot of other flavors mixed in. Cum, obviously, but some sort of bitter remnants of medication as well. 

By the time I finished the bottle, I felt ready to burst. My belly straining against the corset. But the Sitter kept on feeding me. Shoving spoonful after spoonful of cummy pudding down my throat. 

“Please no more Miss...” I begged weakly as she scooped up another bowl once I finished the first. 

“Awww but doesn’t the wittle baby wanna grow up to be big and strong?!” She cooed. Shoving more pudding in my mouth. About halfway through the second bowl, my stomach started to rumble. I don’t know if it was from not going all day, or some sort of laxatives were put in the food or bottle. But no matter what the cause, I had to go...now. 

“Miss...may I...be excused?!” I asked, hoping my manners would yield mercy. 

“For what baby?!” she feigned curiosity, but her eyes betrayed the fact that she knew exactly what was going on. 

“I have to...” I didn’t even bother finishing the statement, we both knew what I was going to say. Still, she finished my sentence for me. 

“Awwww! Does somewon have to go tinky poo poo?!” 

I fucking hated the way she talked to me, but I didn’t care to argue. My bowells were sloshing like a washing machine. I nodded “yes” furiously as I squirmed uncomfortably in the high chair. 

“Well where do you think you’re gonna go, wittle baby?!“ she emphasized the last word to remind me what was about to happen. I knew there was no fighting it, not that I could anymore. 

It was like earlier with the enema, once I relaxed my sphincter, the floodgates opened. Only this time, what filled my diaper was a lot more thick, squishy, and smelly. 

Ariel clapped encouragingly at the uncomfortable look on my face. Knowing full well the deed I just did. The other sissies around me ruffled up their nose and giggled at the smell. 

Sissies were filing out of the Hall now, heading off to their rooms for bed. The three Bouncers had finished running a train on the poor sissy as well. 

“Can we go now, Miss?!” I pleaded with the Sitter. Trying to keep my dirty bottom elevated off the seat of my chair to prevent squishing around in my own filth any further. 

”Not until you finish your pudding!” She said sternly. And I knew she meant it. She was enjoying watching me in my predicament. 

I didn’t argue, just eagerly accepted the pudding in order to get it over with faster. 

“Sure you don’t have another mess to add to your diaper?” She cooed, putting her hand under my skirt and squeezing my diapered crotch. 

My cock immediately began screaming inside its cage. It had been entirely too long since a girl’s hand had been that close to my manhood (not counting the one who fitted me in the cage in the first place). 

“Wet it for me.“ she commanded. There was a fire in her eyes that matched her scattered freckles. “I want to feel it get warm“

What kind of sick freak is she?! I thought, but I also didn’t want her to move her hand away. 

After getting over the initial touching and waiting for my excitement to reside. I focused on wetting the diaper. 

It’s a strange feeling, the first time you wet a diaper. You literally have to force your brain to fight the mental block you have against peeing in such a weird position. Not in a toilet.  Not even touching your dick. Just tucked inside a cage and fluffy pink (and very dirty) diaper. 

Eventually I managed to rewire my brain a bit, and convince it it was okay to let it all out. And I did, a lot. It was so much I was worried the diaper wouldn’t hold it all, but it did. Ariel smiled wickedly. Withdrawing her hand and scraping the last contents of the pudding from the bowl. 

“Come on! Let’s go get you changed and put to bed!”

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Why is she taking such a pointed interest in me? I thought to myself as she led me through the halls of the castle by my hand.

 Is it because i’m the Chosen One? Is it because she saw I needed help? Or is it maybe...something else?

The castle was a lot bigger than I expected. With winding hallways and stairs. Or maybe it just felt huge because every step in heels while walking around in a dirty diaper was unbearable. 

When we finally made it to the Whoridor Common Room. There was a huge statue of a man next to the door, with a large, erect stone member protruding outwards. 

“This is where you input the password” Ariel explained. Pointing to the outstretched stone cock. “I believe the correct sequence for Whoridors is: Right, Left, Up, Down. Then three strokes.“

I waited for her to laugh and say she was joking. But her face was more stoic than the statue’s. 

Reluctantly, I grabbed the stone cock and moved it right, it slid rather easily. I then did the rest if the directions and finally stroked it 3 times like I was jacking it off. It was...very weird. 

But a noticeable click could be heard on the otherside of the doors as a mechanism was released, and the door creaked open almost by itself. 

Ariel chuckled at my gaping face, then grabbed me by the hand and led me inside. 

The room looked like a large living area decorated by a 3 year old girl in love with the color pink. There were sofas and lounge chairs and exercise bikes and even a fireplace. But it was all reminiscent of what you would find in a dollhouse. 

Ariel led me to a side room that looked like a big nursery. 

“Let’s get your diaper changed, stinky gurl!” She said. Patting the changing table. Being a grown man told to climb up and lay down so a girl who was barely 18 could change my poopy diaper was a very specific form of humiliation I never thought i’d experience. 

My cock twinged inside it’s cage the entire time this beautiful girl ran her hands between my legs and cleaned up the mess I made in my Pampers. I was actually relieved once I was finally put into a fresh diaper. 

“Let’s get your jammies on!” She said. She went over to a closet that already had a nametag that read “Larry/Fairie” on it. She opened it up and pulled out the giant pink onesie I had purchased earlier that day at Guyagon Alley. 

I could have very easily dressed myself. But she insisted on doing it. Again making me question her ulterior motives.  It was a miraculous feeling when she untied the strings to my corset, allowing me to finally breathe again. She used a small key on a chain around her neck to unlock the tiny locks on my heels. I wondered to myself if she also had the key to my chastity device. 

Once I was dressed, she led me to the room where the other first years were sleeping. It was row after row of baby cribs. Not adult sized like everything else. It was the same dimensions you would buy for a real baby. 

Several sissies, including Bryan and Henry, were already snoozing away in their cribs. In fact, I must have been one of the last to arrive. There was music playing through some sort of speaker. With a woman’s hypnotic voice speaking softly saying:

You are such a pretty baby gurl...You love the feel of your diaper between your legs...your clitty in your cage...you are not a man...you are a baby...a wittle baby girl...

Ariel led me to crib that literally had my name(s) on it, my trunk of supplies sitting beside it.  She dropped the side railing of the crib down and allowed me to climb inside. 

There were straps attached to each corner post of the crib, which Ariel looped around each arm and leg. “Just until we’re sure you can behave!” She said. 

The last thing before she left was a 4-inch pacifier shaped like a penis that she popped into my mouth. Then secured tightly with a ribbon around my head. 

“Goodnight wittle sissy! Sweet dreams!” She said, and planted a small kiss on my forehead before raising the railing to the crib and locking it. 

I struggled like a toddler would as I watched her leave. Already growing some sort of attachment to her. 

Now I was left alone in this creepy place. The gravity of everything started crashing down on me all at once. This was all real. I wasn’t dreaming. Today was just the beginning. And it would only get worse. I cried like a baby, blubbering and sniffling as much as the rubber penis paci in my mouth would allow. I struggled to get comfortable as I squirmed in the bonds holding me in the crib. Causing my diaper, footy pajamas, and the plastic sheets I was on to all squeak. I didn’t fall asleep until several hours later, when the woman on the speaker's hypnotic voice had made the 247th loop of saying:

You are such a pretty baby girl...You love the feel of your diaper between your legs...your clitty in your cage...you are not a man...you are a baby now...a wittle baby girl...

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*End of Chapter 6*

To Be Continued....