"Wake up, Fairie! Wake up!" Bryan called, leaning over my crib like a Mother would to her Toddler. "It's our first day! It's our first day of SCHOOL!"
I did not share Bryan's/Brianna's —whatever you wanted to call her— excitement.
I had spent the entire night bound by my arms and legs. My sheets and diaper crinkling as I struggled to get comfortable. Listening to the annoying, hypnotic voice of the woman over the speaker system, that was only drowned out by the sobs and whimpers of other sissies in their cribs.
Brianna did not look like one of the sissies who was up all night crying about their new living situation. He looked like he got the best sleep of his life.
“First day of school!” He repeated. Untying the ribbon around my head holding the large penis pacifier in my mouth. I was so relieved to have it removed. My jaw felt like it had been locked into place around the rubber cock.
My own cock was straining inside of it’s tiny cage as my morning wood struggled for space to expand. It left me with a painful throb down there. The inside of my diaper also felt a little sticky, it must have just been leakage from precum or something.
I rubbed my arms and legs to restore circulation as Brianna freed me from my bonds, unlocked my crib and dropped the side rail. My legs were so numb it was almost difficult for me to stand.
There were Sitters helping other sissies out of their cribs and over to the changing tables if necessary. Some begrudgingly getting out of bed, others springing to action with Bryan-like enthusiasm.
“Are you gurls in need of a change?” asked a stunning looking blonde Sitter. Stopping us in our tracks as we weaved our way through the cribs.
Before either of us could mutter a reply she was pulling the backs of our onesies open and peeking into our diapers to check for poo. This girl was maybe 20/25 years old tops, and i‘m a man in my mid-thirties getting his diaper checked like a toddler because he can‘t be trusted to give an accurate response as to whether he pooped it or not.
She didn’t even really bother looking in our pajamas to check the front of our diapers for piss. Just squeezed the front of them to be more of a cocktease than anything. It made my dick wiggle inside its cage.
Satisfied, she tapped our butts and told us to both get dressed and meet down at the Great Hall for breakfast and schedules.
I had no idea what to pick out or wear. Luckily, Brianna’s locker was right next to mine in the dressing room, and he obliged to hold up the various dresses in front of me to see how they would look.
I ended up picking a white dress with pink fringe and accents. It had a little pink ducky on the front which I thought was ridiculous, but there wasn’t much to choose from that wasn’t utterly humiliating or emasculating.
The skirt of the dress did nothing to cover up my diaper. I was very aware of how exposed it was. But none of the other sissies’ dresses left much to the imagination either.
Apparently, as per school rule, all shoes needed to have at least a 3-inch heel. So I stuffed my feet into a pair of pink pumps.
“Come on!” Bryan said after we had both gotten dressed. He was wearing a pink satin dress with white fringe. “We’re gonna be late!”
We rushed downstairs (which was incredibly difficult to do in heels) and made our way to the Great Hall.
Outside the door was four lines of diapered first years. Waiting in line with their respective Houses for their schedules.
”Name?” Said Professor Mars when I arrived to the front of the Whoridor line.
“Larry Parker” I answered, without even thinking.
“I think you mean Fairie Parker. Or have you already forgotten about your little Sorting incident yesterday?” She snapped. Flipping through the cards until she found mine.
Once we both had our schedules, Brianna and I made our way into the Great Hall. We sat next to Henry from the train, who took one look at both our outfits and scoffed. Henrietta’s dress wasn’t nearly as poofy, it was more straight and highlighted his curves more. I almost mistook him for an actual woman.
We pulled open the trays to our highchairs and sat down. There wasn’t a buffet of food like there was last night.
Instead, we were each brought a bowl of runny porridge and a bottle of the school’s ‘formula’. Both of them tasted like their base ingredient was cum. I had no idea where they manged to get it all from, but I wasn’t about to refuse to eat and have another incident like yesterday.
There were a few reasons for them only giving us baby spoons: 1) it only made things more humiliating, 2) it helped reinforce the idea that I was now a ‘baby’ and 3) it made it impossible to finish my meal in a few large bites like I could with a normal sized spoon. Instead, I had to take a larger quantity of tiny portions. Making the taste in my mouth linger from the more arduous process.
As I forced a baby spoonful of cummy porridge in my mouth, Bryan and I went over our schedules. Mine read as follows:
Class Schedule: Fairie Parker
Fashion - Professor Aguilar
Women's Studies - Professor Binns
Creative Writing - Professor Bartlett
Daycare - Sitters
Lunch
Analology - Professor Gape
Feminine Physique - Professor Michaels
Intro to Fellatio - Professor Mars
“Looks like we have almost all the same classes!” Brianna remarked. Even though I didn’t show it, I was relieved to have someone I knew to help me cope with my new life.
Henry also shared a very similar schedule too. “Come on!” he said. We better hurry if we want to make it to our first class!
We shoveled down our food, not wanting to be stopped by the patrolling Sitters who would force us to eat it the hard way. I gulped down the rest of my bottle, it tasted like tangy breast milk mixed with cum and a variety of medicines. I gagged to the point where I almost vomited, but managed to keep it down as we climbed out of our high-chairs and scurried off as fast our high heels would allow us.
“Where are you goin’, first year?!” Said a large Sluttykin in a poofy dress. Luckily he wasn’t speaking to us as we scampered through the hall. It was a young Maidenlaw on her way to class. “I said ‘where are you goin?!’” he repeated. It was weird seeing a bully dressed in such a feminine way. The Maidenlaw mumbled something inaudible, and two other Sluttykins laughed as they slammed the whimpering maid against a locker. All three pulling down their panties and pulling out their undersized cocks as they ripped off the diaper of the Maid and began fucking her as we passed.
“This way!” called Henrietta as we turned a corner and entered a very fragrant room.
Each desk looked like a show girl’s make-up quarters. With personal mirrors, an array of beauty products, and tools such as tweezers, curlers for your hair and eyelashes, and much more.
“Come in ladies and have seat!!” came a peppy, flamboyant voice. We turned to see a short, skinny little man. One that you could instantly tell by their walk and talk was very, VERY gay. “I’m Professor Aguilar! And i’m gonna show you lovelies how to look like a REAL woman!” He said as he clapped in excitement.
The three of us found our seats as close to each other as we could manage. There were more than just Whoridors here. Apparently everyone, no matter what House, needed to learn to look like a ’real woman’.
“Ohhh i just loOoOove getting all you little first years in here and showing you how to get rid of those icky man faces you have! So rule number 1: you better NOT come in here with that face all scruffy! No man wants their lady growing a better beard than they can! So you’ll need to shave nice and close before those hormones start kicking in!“ There was whispers of surprise at the mention of hormones. “Usually rule #2 is you will always come in looking made up and on fleek! But seeing as how this is first period, i’ll allow you to do your make-up in this class. But hurry honey because some of you REALLY need it!”
With that, there was a rustle of materials as the sissies began scrounging through the make-up products and (attempting to) apply them. Most of us had no idea what we were doing. I picked up a tube of red lipstick as that was the only thing I was somewhat familiar with and started applying it. I still wasn’t used to looking at myself in the mirror, my pigtails looked ridiculous, but i looked even more silly once my lips were (poorly) painted red.
Bryan was a little more experienced, but still not great. I got the feeling he was more used to wearing it rather than applying it. I’m sure the application part came more from his sisters.
Henry, however, looked like a fish in water. Expertly applying eye liner and even adding a swooping effect at the end of each eye. He had his whole face on before i could even decide what to apply after the lipstick.
“Oh honey! You look GORGEOUS!“ chimed Professor Aguilar after seeing Henrietta’s handy work. “10 points to Whoridor!”
Henry smiled, obviously enjoying the praise. Other Houses scowled in the background.
“Not bad Beasley but not so heavy on the mascara!” He told Bryan. “And you!“ he said when he came to me. “What exactly possessed you to think that red would be a good color to go with that hideous pink outfit you have on?! 10 points from Whoridor!!”
There was no need to add blush now, as my face was producing it naturally. All the other Houses snickered now as the Whoridors were the ones scowling.
“Let that be a lesson to you all: it doesn’t matter how well you apply your make-up. If it’s boushie, then you gon’ look boushie” he said, snapping flamboyantly and strutting off dramatically.
We spent the rest of the period learning the ways to pick the proper color eye shadow, and practiced applying it. I still didn’t have it down by the time the bell rang, and my face ended up looking like a cheap hooker’s who got sent through a car wash.
Our next class, Women’s Studies, wasn’t even taught by a woman. It was some creepy old man named Professor Binns who just stood at the front of the class with his pants down while one of the sissy students knelt in front of him on their knees and sucked him off. He droned on about the importance of Women’s Suffrage while he jizzed in the sissy’s mouth. After the sissy gulped it down, wiped her mouth, and returned to her seat, Professor Binns had already picked out another sissy to take his slimey grey dick in their mouth.
I got my first homework assignment in Professor Bartlett’s Creative Writing class. Ms. Bartlett was an older woman with a demeanor that dared you not to cross her. We were tasked to write a 5-page erotic short story about a topic of our choosing by Wednesday. It had been years since i’d even picked up a pen to write more than my name and signature, much less an essay. What’s worse is we weren’t allowed to type it. And if our handwriting wasn’t deemed ‘dainty’ enough, we would lose points.
Midway through her lesson on the various synonyms for male genitalia, I felt the strong urge to pee. I shifted in my seat as I tried to hold it, but it just made my diaper crinkle noisily.
I knew better than to ask to go to the restroom. The last sissy who did that in Binn’s class was escorted out by two Bouncers. His wails could be heard from the hallway over the sound of the sissy slurping the Professor’s cock.
I couldn’t help but feel like all the sissies in the room were watching me squirm at trying to hold my piss. When, in reality, most were either dozing off or daydreaming about their own problems.
Finally I just closed my eyes, and felt the warmth spread throughout the front of my diaper. I didn’t hear a word Professor Bartlett said after that as I spent the rest of class trying to get comfortable in my soggy diaper.
*******
“What’s Daycare?” I asked Henry after the bell rang, seeing it was next on our schedules.
“Not sure...” he replied, appearing anxious for the first time “There wasn’t any required textbook for it. I have no idea what we were even supposed to study to prepare!”
Turns out it was just as simple as it sounded: it was a time for us to go inside a large room with no desks and act like a bunch of babies.
There were sissy babies everywhere crawling along the floor (walking was obviously not allowed) with Sitters standing over and monitoring them.
“Awwww! Did you find a new friend Stewie?!” one Sitter said to a pair of Mufflefluffs. “Why don’t you two give each other a kiss and say ’hi’?!” Both men glanced over at the Bouncers guarding the door, cursed, then looked disgusted as they met each other’s lips.
There were sissies playing with blocks and stackable cups and dolls. All of them looked bored out of their minds.
It was obviously all a ploy to regress and humiliate us for an hour a day. But it also seemed to provide a training ground for daycare workers and future Sitters.
“What about this one, Lauren?” said a pair of girls standing over me as I crawled towards the Playdoh. One girl was obviously a Sitter, wearing the badge and everything. The other girl, Lauren, looked like she just turned 18 and was looking for a babysitting job.
“Check his diaper, and make sure to use baby talk!” said the Sitter.
“Hewwo wittle one!“ Lauren said, kneeling down to talk to me like a child, “Did somewon make an uh-oh’s in their diapy?!”
She didn’t even wait for a reply, not that i’m sure i’d have given one... She just simply reached under my skirt and squeezed the front of my diaper.
“Awwww! Did somewon make a messy wetsy in their diapy?! Hmm?! Did somewon make tee tee with their wittle pee pee?! Do we need to go change your soggy diapy?!“
She was about to lead me away before the Sitter stopped her with a small cough.
“Ohp! I almost forgot!” Lauren said, looking a bit flustered but maintaining her chippy, dominating demeanor. “We only change diapies that have number one AND two in them! Did you go poo poo too?!”
Again she didn’t wait for a response. Just lifted the back of my skirt and peeked on in.
“Ooooo nope! No poo poo’s yet! Do you want us to sit and play Pat-a-cake with you until you do?!”
She plopped down in front of me. Holding her hands out. I hated that I already knew this game meant for little girls. Back in grade school, there was a girl on the playground I had a crush on and would play with.
We clapped hands in the typical motion while Lauren sang:
”Sis-sy-gurl, Sis-sy-gurl’s not. A. Man. Make me a poopy as fast as you can!“ to the tune of the Pat-a-cake song.
After about the 35th time of clapping to her stupid song, I was about ready to blow my brains out. Instead, I just decided to blow up my diaper.
I pushed with all my might. Forcing anything out that I could. It turned out to be a lot. Or at least, what i thought was a lot. I hadn’t really learned how to gauge it seeing as how this was my first official poopy diaper.
Lauren giggled at my face and scrunched up her nose at the smell I’d just produced.
“Awwwww! Did you go poo poo’s?!” she asked, as if she didn’t already know.
I nodded sheepishly. She was such a pretty girl, and it made me even more humiliated that she was talking to me about how I was sitting in my own filth.
“Awww! Do you wanna go change your diapy now?!”
Again I nodded. Unable to summon words.
“Okay! Come on wittle baby!”
She made me crawl next to her over to the changing area. My diaper felt extemely heavy from the loads of piss and shit I was hauling. It made it sag and bounce as I made my way to the changing mats on the floor at the edge of the room.
I found a spot next to a Sluttykins that was face down on his mat, arms at his side, humping the floor in his yellow and brown diaper. A Sitter standing over him with her arms crossed.
He caught my eye as I laid down on my mat next to him. His face was purple, tears streaming down his face while he sucked his paci and gave me a look that said “please don’t watch my shame”
But honestly I felt just as humiliated as he did. A girl who was barely 18 was about to see my tiny penis covered by a cage and a mess of poo.
Lauren knelt between my legs. The Sitter that was mentoring her stood behind her, somewhat paying attention to us, but also watching the show going on next to me with more amusement.
Lauren grabbed the supplies she would need for changing me out of a bag she carried.
“Okay poopy pants! Let’s see what we got in here!” She peeled open the tapes of my diaper and opened it up to expose the brown mush inside. The smell was enough to make even me gag, but she didn‘t seem the least bit bothered by it. That didn‘t stop her from teasing me though...”peee youuuu!!! Stinky boy! You made quite the mess in here!”
She grabbed several wipes and began cleaning me up. Lifting my legs as she vigorously wiped my butthole.
“Ohhh you’re one of the SUPER tiny ones!“ she said as she cleaned the cage around my cock. I tried to ignore her, but even the sissy humping the floor next to me smirked.
Once she got me in a fresh diaper she bid me farewell and let me go back to ‘playing’.
Luckily I didn’t have to pretend to enjoy the blocks for long before the bell rang for us to go to lunch.
**************
”Did they spell this class wrong?” I asked Bryan, looking at my schedule. “Analology? Don’t they mean ‘Analogy’? As in comparisons?”
He just looked at me with a mouthful of mushy carrots and smirked at my naivety.
When we walked into the class I realized why he gave me such an idiotic look. On the seats of each desk was a average-sized rubber dildo sticking straight up.
All the sissies in the room looked around incredulously, unsure what to do. Henry scoffed, looking at everyone as if we were dense. He pulled his hair back, leaned over, and took the rubber cock in his mouth. Everyone watched as he gave the dildo on his seat a quick, sloppy blowjob. After a couple seconds, he seemed to be satisfied. He straightened up, pulled his diaper to the side, and maneuvered himself on top of the dildo. Allowing it to slide inside his asshole until his cheeks rested against the seat. The dildo fully inside him.
The rest of the sissies followed suit. Sucking and moistening their dildos and easing their way onto them. Some were more ‘accepting’ of the dildo than others.
I looked down at mine. Not daring to suck it without knowing how many asses it had been in. I simply spit on it several times before pulling my diaper down enough to expose my asshole. I could barely even get the tip in without feeling like I was being split open.
I barely had it 1/4 of the way in when the door swung open, and a very dark, brooding man stormed in.
“Open your books to page 274.“ he said pointedly.
The sissies scrambled awkwardly to grab their book The Ins and Outs of Anal Sex by Sasha Romaine from their bags while keeping the dildo in their ass.
I still hadn’t gotten mine all the way in yet, about halfway now that I thought about it, but it made my legs quake to hover over the seat like this.
“Seems we have a little trouble finding our seat and materials...” the Professor said. I thought he was referring to me, but luckily he was speaking to another sissy at the front of the room who had forgotten their book, and barely had the dildo in their hole at all.
Professor Gape glided over to the sissy, and rested a hand on his shoulder. “Perhaps you require a little...assistance?” He regarded the sissy with contempt. Then forcefully pushed him by the shoulders down onto the dildo, hard. Forcing the sissy’s ass down on the chair, and the dildo to jam up his asshole. The sissy whimpered in pain.
“Now, who can tell me how many sphincters the human anus has?” He asked, ignoring the cries of the sissy he just abused.
Henrietta’s hand shot up immediately. Waving frantically like that kid in school who always knew the answers.
Professor Gape ignored her as he scanned the rest of the room.
“Miss Thompson?” He asked a Mufflefluff student in the back whose head was drooping.
“Uh...one?” He answered, as if confused by how easy the question sounded.
Henrietta shook her head, then turned back to Gape for a chance to answer.
“Abysmal, Mr. Thompson. I see someone isn’t even familiar with their own body...10 points from Mufflefluffs. Anyone else?”
When no one answered, he finally gave in to Henrietta’s hand.
”Alright Miss Hopkins, go ahead...” he said.
Henry drew a deep breath, and spouted his (obviously practiced) textbook answer:
“At the anus, there are two sphincters which control the exit of feces from the body —the internal anal sphincter and the external anal sphincter— the inner sphincter is involuntary and the outer is voluntary.” He crossed his hands on the desk and nodded, like a young child proud of themselves and ready to be praised.
“Yes Miss Hopkins...i see you are VERY familiar with your own body...and those of others im sure...” Gape said, unimpressed.
The rest of the class sniggered and Henry’s face flushed at the thought of being called a slut. Something he obviously took very much offense to.
“And you.“ said Gape. Looking directly at me. “If you think that silly mark on your forehead makes you any more special than the others here, you’ve got another thing coming.”
I felt all eyes on me now. I didn’t know what to say. Just sat there panicked. But the focus quickly shifted as the Professor flipped through his own book to page 247.
“What’s up his ass?” I whispered to Bryan.
”He’s just butthurt that he doesn‘t teach Fellatio. He’s always had his eye on that job. I think the mark on your head and the whole prophecy thing just reminds him of it and rubs him the wrong way.”
We spent the rest of class looking over the internal structure of the rectum. I couldn’t focus on much with dildo now almost buried entirely in my hole now.
Before class ended, Professor Gape had us stand up and “clean” our respective dildos. Sissies grimaced and gagged as we were forced to take the rubber cocks in our mouths and suck them before we left. It was the first time I saw Gape smile.
*********
The class for Feminine Physique took place in what could only be described as a gym. Professor Michaels was a very tough, almost manly looking woman with how toned and shaped her muscles were.
"Alright you prissy sissies, listen up!" she shouted after blowing a whistle. "I look at the lot of you and I see a bunch of middle-aged men who let their bodies go to shit and are now trying to stuff themselves into a size 4 dress. Well let me tell you something: those pudgy stomachs of yours are probably half the reason most of you ended up in here. If you were to a look at a woman with saggy breasts and a beer gut would you want to fuck them? I think not. So that's my job with you little pipsqueaks: to make you have a body that looks appetizing and fuckable! Now drop and give me 20!" she barked like a drill sergeant.
On the floor was another array of dildos sticking straight up. We had to get in the push-up position with our head above the dildo, so that when we dropped down the dildo would enter our mouth. Why did everything have to involve dicks and dildos?? It was like all these people thought about was sex...
After about 8 push-ups I collapsed down, on the floor. The rubber cock making it's way so far down my throat that I almost threw-up from gagging so hard. Professor Michaels took her riding crop to me several times until I hoisted myself back up and completed the push-ups properly.
BEEEEEEEEEEEEEEEPPPP!!
"Alright ladies! Now let's see some squats!"
**************
When we got to Intro to Fellatio, Professor Mars — the woman who did the sorting — was already at her desk smiling brightly to all that walked in.
“Please come in! Make yourselves at home!” she said sweetly. I was immediately relieved by her chipper attitude after an hour in grumpy Gape’s class and another hour of getting barked at in Professor Michaels'.
The desks were also not adorned with an array of dildos...so that was nice too.
Professor Mars was a beautiful young woman. Her feminine physique accentuated her outfit nicely. She had beautiful breasts and a nice, tight ass. It made my cock wriggle inside it's cage just looking at her.
"Now, who can tell me the most sensitive part of the penis?" Ms. Mars asked after everyone had grabbed their seats.
Henry's hand shot up the same way it did in Professor Gape's class.
"Yes, Henrietta?" said Ms. Mars, delighted to call on her.
"The most sensitve part is the glans, or 'head' of the penis. Specifically the frenulum which is the little line located on the underside." he said proudly.
"Yes! Well done! 5 points to Whoridor!" said Ms. Mars. "So class it is important to pay close attention to the head of the penis when performing a blowjob. That is why today we will work on proper tongue technique! So if everyone will just get out their 6-inchers..."
Everyone sifted through the various dildos in their bags. I looked through mine and for the first time noticed all of mine were colored black. Must have been a joke on Tyrone's part.
All 26 sissies spent the next 30 minutes sucking on a dildo on their desk. Performing each of the various tongue techniques Ms. Mars called out. The Tongue Tornado. The Wishy Washy. The Lollipop. etc.
I was reluctant on all of them. 2 days ago I never thought I'd be in this position. Much less with a dick in my mouth. The idea disgusted me to my very core.
"And it looks like we have a celebrity in our mists!" said Ms. Mars. Coming to the desk beside me. All eyes on me again. "For those who believe in such things," she announced "this one here is expected to do wondrous things!"
This stupid birthmark was beginning to be the death of me. I was tired of being constantly called out about it, and to have to live up to such high expectations.
"Why don't you come to the front of the class so you can demonstrate your particular gift? Perhaps we can all learn something!" she said, taking me by the hand and leading me to the front of the room.
"On your knees...that's a dear" she said.
I was horrified. Was she about to make me suck off a Bouncer in front of the whole classroom? Or perhaps another sissy?
I was quivering so much I could barely stand, so I was on my knees without much resistance.
I looked around for who I was going to have to service. But the Bouncers at the door stayed put, although smirking in amusement. I kept my head on a swivel, worried some sissy was going to come up behind me. I must have looked ridiculous in my fright, because the whole class was giggling.
I turned to see Ms. Mars raising up her skirt.
Oh. Did she mean she wanted me to eat her out? I thought. Because I would SO do that!!
But my jaw dropped when she raised her skirt. Under her panties was an already stiffening 5 inch cock!
I couldn't believe it. The ONE woman I was attracted to since being here was actually a dude!
Her cock bobbed up and down as it waited for me. I glanced over at all the prying eyes of the other sissies in the classroom.
There was no backing out. I knew what I had to do. But other than Graco's raping of my helpless mouth, this would be the first time I would have to willingly suck someone off.
It was awkward having everyone staring at me. But the tension of the silent stares from everyone in the class propelled me forward.
The spongy flesh of the head in my mouth was a strange sensation. It was nothing like the dildos we had been practicing on. I quickly realized I had no idea what I was doing. I tried to remember the techniques we had just learned, but my mind was so distracted by the feel of a cock in my mouth, and the stares of my peers.
I could almost tangibly feel their eyes on me. So I closed mine to try and block it all out and focus on what I was doing: attempting to suck off the teacher at the front of the classroom.
"Well, I can see you've learned basically nothing today" Miss Mars said, staring down at me disapprovingly and not looking the least bit pleased at all despite her dick in my mouth.
The class giggled. I wanted to curl up into a ball and cry. It was humiliating enough giving a blowjob in front of everyone, it was even more humiliating knowing I was doing a terrible job.
"I think that's enough." she said after about 5 minutes of me trying feebly to get her off. She plopped her cock out of my mouth and pulled her panties back up. Walking behind her desk and resuming instruction as if nothing happened.
I slowly, pitifully got up off my knees and returned to my seat. Everyone snickering except for Bryan and Henry, who obviously took pity on me.
When the bell finally rang, we all went off to dinner and then back to the common rooms. Where everyone in Whoridor shared their experiences and feelings on the day.
"I can't believe you didn't know Professor Mars was a sissy!" Bryan teased. "She's only one of the most famous sissy pornstars in the business!!" He punched my arm lovingly to make me feel better. And it kind of did. I just laughed it off and tried to delete the first day of Sissy School from my mind.
If just one day was this bad, I can't imagine how the whole year will go...
___________________________________________________________________________
End of Chapter 7
**To Be Continued**