Sissy School Chapter 8 - Frustrations

Author's Note: This is it! The brand new chapter you guys voted on and were waiting for! Thank you SO much for your support and patience! I really hope you like it! :)

“Inspection time!” Professor Aguilar called at the start of class. The sissies grumbled as they stood up out of their desks and formed a line shoulder to shoulder at the front of the room. “Shoes and stockings off, ladies!”

Larry kicked off his pair of black Penny platform heels, pulling his thigh-high stockings down and off. He’d hoped his legs were smooth enough this time, his bottom was still sore from the paddling Professor Gape administered the other day, he didn’t need another one.

It had been two weeks since Larry first stepped foot at Sissy School. To say he was getting adjusted to his new life would be…lying. The cage around his cock always kept him in a constant state of discomfort and arousal, he hardly slept at night, and he still wasn’t used to the feeling of a poopy diaper. He hoped he would never get used to that…

Professor Aguilar made his way down the row of quivering sissies, inspecting their faces for stubble and running two fingers up and down their legs from their feet all the way up to the folds of their diapers.

“Excellent, Ms. Frasier!” Aguilar said to Larry’s friend Henry, “Nice and smooth, even around the ankles! A very tough spot! 10 points to Whoridor!”

The other Whoridors in line, including Larry, smiled and cheered. Henrietta flushed and grinned widely from the praise, always enjoying being the top of the class.

Then it was on to Larry’s other friend, Bryan. Aguilar knelt and, after touching Bryan’s leg, immediately yanked his hands back in the flamboyant, exaggerated way Aguilar does. “Ms. Beasley!” Aguilar gasped, “Did you shave with a weedwacker??” Bryan’s face dropped, he had a hard time affording razors, being one of eight children in his family. He either inherited razors from his seven older sisters, or he continually used one way past its life span. As a result his legs were often heavily irritated, riddled with cuts and nicks, or just downright stubby. “15 points from Whoridor!” Aguilar snapped flamboyantly, and the same Whoridors from before groaned. Bryan looked like he wanted to shrivel up and die in embarrassment.

Graco grinned, scoffing at Bryan standing next to him and turning up his nose while his own legs were inspected. “Well done, Gracie, 10 points to Sluttykins!”

And so it went, down the line, one by one until Professor Aguilar finally came to Larry.

“Ahhh, Fairy Parker. The ‘chosen one’...” he chuckled haughtily, like the name Larry didn’t even choose for himself was some kind of silly joke, “Let’s see if you made the cut! Off we go…”

Aguilar ran his hands up and down Larry’s legs several times. More than he did with any other sissy, turning up his face when he didn’t find anything. “Hmm…well, I guess that’s a decent job,” he said, standing up, “But let’s have a look inside that diaper.”

Larry deflated, “What? Why?”

But Aguilar was already lifting Larry’s school girl skirt and taking a peek inside. “Looks like you’ve got quite a bit of stubble around your cage, Ms. Parker!” he tisked, “10 points from Whoridor!”

There was a collective outcry from the other Whoridors, but none louder than Larry. “What?! That’s not fair! You didn’t check anyone else’s privates! And how am I supposed to use a razor when ya’ll never let me take this stupid cage off?!”

“You use Nair or any other hair removing cream, you dolt!” Aguilar chided, looking at Larry like he was the dumbest sissy in existence. “And that’s another 20 points from Whoridor for backtalking! Do you want to make it 30?”

Larry pursed his painted lips together and hung his head. “No sir,” he said with a curtsey to hopefully limit the damage, “Sorry sir.” Larry remembered the pain of the hair removal cream from back in the salon at Guyagon Alley, he certainly wasn’t looking forward to that again.

“That’s what I thought,” Professor Aguilar replied, “Now, everyone back in your stockings and shoes, and back to your desks! Today we learn about Fashion from the Regency time period! Has anyone seen Bridgerton??”

******

Bryan was chosen to suck Binns’ dick in Women’s Studies. He was a mixture of nerves and excitement as he strolled from his desk to get on his knees in front of the Professor who already had his cock out.

Bryan’s red curls bounced to and fro as he took him in his mouth and started bobbing back and forth. He choked and sputtered as Binns forced his head further down while he spoke about how Jane Austen’s take on 18th century middle-class women in no way reflected the average American female.

Larry tried to keep his own head from bobbing in drowsiness, his only form of entertainment was watching his best friend at the school suck his teacher’s dick. But even Larry could tell his technique was lacking. Bryan had both his hands on Binns’ hips, when he could have been using them to cradle the balls and stroke the bottom of the shaft. He had an overly sensitive gag reflex, and his posture was poor, his back would surely be aching after a long session. But what he lacked in technical skill, Bryan made up for in enthusiasm. His ‘mmm’s and ‘ummphs’ made him sound more pornstar-like, without the silly ‘gluck gluck gluck’ sound.

“Austen was one of the first to show female characters that weren’t inferior to men in her novels. Many credit her as being one of the forerunners to feminis–OW! Not so much teeth, Beasley!”

The class giggled a bit at Bryan’s poor display, there probably would have been more jeers if more sissies were awake, but Bryan’s face flushed redder than his hair all the same.

It took almost the full length of class for him to make Professor Binns cum. Usually he would have gone 2-3 times by now.

*****

“I suck,” Bryan said to Larry and Henry on the way to Communications. “How can I be a sissy if I can’t even suck a dick?” he groaned.

Larry still thought it a bit weird to critique his friend’s blowjob skills. Though he had learned enough in his 2 weeks to probably help him, he didn’t think he had room to talk. Luckily, Henry took over in explaining his downfalls, if a bit unsympathetically.

“You need to use your hands for more than just break time.” he said, “You should be using your hands as much and as often as you’re using your tongue, which is to say, all the time! And for god sakes, keep your back straight! You looked like Quasimoto giving a blowjob!

They laughed as they turned the corner into Bartlett’s room. Communications was Larry’s worst subject by far. He’d spent the previous week trying to come up with something to write about for his erotic essay, but he’d never been much of a writer. His philosophy in actual school was that he would never need to learn how to write more than a paragraph or two for emails, so why do it? If only he’d known over a decade later how wrong he was…

“What’d you get?” Bryan asked Henry when their essays were passed back.

Henry looked like he was on the verge of tears, “A-...can you believe that?? An A-!! I don’t understand..” He said, reading it over again and again.

Bryan just shrugged, seeming rather satisfied with his B, hoping it would make Henry feel better…it didn’t.

Larry tried to tuck and hide his paper before either of them could ask, but he was unsuccessful. “Come on, Larry! You know we don’t care! Show us!”

It was a D. There were more red marks from Bartlett than there were black ones from Larry’s pen. On top of the myriad of grammatical mistakes, she’d criticized his use of ‘passive voice’ (whatever that meant), comma splices, and not making his handwriting ‘dainty’ enough. It was like she didn’t even care for the content he was writing, just wanted to point out all the mistakes. Finally, he got to a note at the bottom of the page that read: “More dry and boring than a Dickens novel”.

Larry hadn’t known what to write about, so he decided to pen about a time back when he and his wife Sherry were still having sex. They had gone on a romantic, week-long getaway to Punta Cana, and spent most of the time walking on the beach and making love. Ironically, it was the week before Larry ended up cheating on her. But if he couldn’t grab the reader’s attention with something he knew about and experienced, how could ever come up with something better?

“Today we’re going to work on using your Sissy voice,” Professor Bartlett announced, she had her arms crossed, with a cane tucked tight against her forearms. “Many of you have been burdened with a laryngeal prominence, or ‘Adam’s Apple’ as the laymans call it. Unfortunately, it gives you that dreadful, low-pitched tone to anything you say.”

Larry looked around the room, most of the sissies had the protrusions on their neck hidden by either a collar or choker.

“I intend to correct that unfortunate mutation you’ve been burdened with, at least until you can get the proper surgery.” she strode over to the whiteboard, rapping the cane across the first line, “You will all read this aloud in your wimpiest, most pathetic, and highest pitched voice! 1, 2 ready and…”

In unison, the class full of middle-aged sissies read from the board “Which hole would you like to put it in, Daddy?”

Larry felt ridiculous. Trying to imitate the bimbos he’d seen in porn.

“Again!” Bartlett barked, and the class repeated the line. “Raise the larynx! Keep your vocal tract smaller and tighter! Do the same with your mouth! Don’t open it so wide until you’re ready for that dick!” she instructed, rapping her cane across certain desks. “Higher!” she seethed when sissies still sounded too manly for her tastes. “Higher!”

Which hole would you like to put it in, Daddy? The class continued to repeat in chorus.

Professor Bartlett stopped in front of a very large Maidenlaw. He was stuffed in a dress that was very ill fitting, though Larry doubted they made many dresses that would fit someone of his size. He looked like a football player forced to dress like a cheerleader after losing some sort of bet.

“You,” Bartlett said, “What is your name?”

“Vanessa Wilfork, madam,” the Maidenlaw replied in a deep, baritone voice.

The class giggled at the sound of the deep tone, but Bartlett was far from amused. “Vanessa, do you mind reading line 2 from the board, please?”

The giant sissy gulped, squinting through her long, fake eyelashes to see what was written. He cleared his throat and read, “Would you like to use my throat as a fleshlight?” in a voice that could hardly be considered dainty or feminine. But there probably wasn’t much higher the sissy could go.

Bartlett’s face was tight, Vanessa shifted uncomfortably.

“Front of the class, please, Miss Wilfork.” Bartlett said, leading the way through the aisle.

The big Maidenlaw was practically quaking both ground and body as she made her way to the front of the class behind the teacher she towered over.

“Bend over the desk please,” Bartlett instructed, “Face the class, diaper down.”

Vanessa’s bottom lip was poking out in fear as she bent over Bartlett’s desk, hiking up her skirt and pulling down her diaper.

“Repeat the line, Vanessa.” Bartlett said, running the cane through her fingers.

The desk creaked and rattled from Vanessa’s trembling weight. “W-would y-you l-like t-to use m-my th-throat as a…f-f-f-flesh–ARGHH!”

The cane thwacked across his backside. “Higher, Miss Wilfork!”

“Would you like to use my–OWW!”

“Higher!”

“Would you like to–AHH!!”

“Higher!”

And so it went for several minutes. Vanessa trying pitifully to sound feminine while getting her ass positively blistered by Bartlett’s raining blows. After 15 minutes of the display, Vanessa was blubbering so much she finally belted “WOULD YOU LIKE TO USE MY THROAT AS A FLESHLIGHT?” so loud and high-pitched they probably heard her down the hall.

“Much better Vanessa, you can return to your seat now.” Bartlett smiled, as if she had just taught her how to spell a word properly.

Vanessa was clutching her diapered backside the entire way back to her desk.

“I want all of you ladies to practice using your Fem voices today while you’re chatting.” Bartlett ordered. The class thought she meant in conversation with each other. But it wasn’t until these small black boxes with headsets attached to them came out that they realized their assumptions were mistaken.

A box and headset was distributed to each student. Larry put the flimsy device over his ear, adjusting the microphone.

“The box is connected to a phone sex hotline,” Bartlett explained to the crowd of confused faces. When I open the lines, you will communicate with your client in the prettiest, prim, and most pathetic little pansy voice you can muster until you make them cum. 50 points to the house that completes the most transactions in the next 30 minutes! Aaanddd GO!”

Immediately red lights started flashing on the black box in front of Larry. It looked like an old answering machine or cassette player. There were 6 buttons and 6 numbers, all of which were lit up. Larry assumed they must have been callers. He pressed button 1 and heard the line click. “Umm…hello?” he said into his microphone, a little more manlier than intended. The line immediately went dead, the red light around the number 1 on the device disappeared..

Too deep. Larry thought. He cleared his throat and tried to readjust his pitch, like a singer getting ready for a big solo.

He pressed the number 2. The line clicked on, “Hello?” he said, much better this time.

“Hi,” said a gruff voice, it sounded deeper than Vanessa’s had. “How are you?”

“I’m…fine…” Larry lied, feeling more than uncomfortable talking to a complete male stranger.

“Good. Good” he purred.

It was quiet for a while. Awkward. Larry didn’t know what to say. He cleared his throat, trying to maintain the same pitch. Did they know they were talking to a sissy? Or did they think it was an actual girl?

“What can I…help you with…sir?” Larry mewed uncertainly.

“You can help me with this dick.” the voice said pointedly.

Larry was a bit taken aback, just jumping right into it like that. He glanced around at the other sissies, they seemed to be chatting away just fine. Some narrowed their eyes in concentration, whispering to make it more sensual, some were even laughing like they’d just come up with the best inside joke. The chatter was distracting, it made it hard for Larry to focus, especially since everyone seemed to be doing so much better than him.

“H-how can I…” He stuttered, “I m-m-mean..what can I…watta you want m-me to…”

The line clicked off. Another red light faded beneath the 2.

Larry buried his face in his hands. This was a lot harder than he thought it would be, and he already suspected it would be difficult in the first place.

Henrietta was in an intimate conversation with a stranger. Giving every minute detail about how she would run her tongue along the veins pulsing around the shaft of his cock. Larry marveled at her way with words. How they seemed to flow so effortlessly. The way her tone was both seductive, submissive and somehow dominating all at the same time. Larry thought those last two were antonyms, but somehow she pulled it off.

His next two calls didn’t go any better. He got a little bit further than the last, but he still stumbled and stuttered through his words, took too long to think of responses, and overall just wasn’t confident enough to be sexy. His red lights were dwindling. He took another deep breath, and pressed line 5.

“Hello there…” came a creepy, gravelly voice through the ear buds. “What are you wearing?”

Larry had to look down to remember, “Uh…a white blouse,” he cleared his throat, realizing he sounded too manly again, and brought it up a few octaves, “umm…a pleated skirt, and some…thigh highs.”

He decided to leave the damp diaper out, figuring that might kill whatever it is he was trying to do.

“What about that mouth, baby?” the creepy voice said, “what you got on those lips?”

Larry had to think back to what he put on this morning, not that it mattered, it wasn’t like the man on the phone could see him. “Some pink lipstick and raspberry lipgloss,” he said.

There was an audible, heavy breath on the other end of the line. “And what would you do with that mouth, baby?”

“Whatever you wanted…Daddy.” Larry added at the end. He figured that last little tidbit would make him sound sluttier and swing things in his favor. The breath quickening in his ear told him that was the correct choice.

“I want you to suck my dick,” The creepy man said, Larry couldn’t help but cringe at how gross he felt, but the man taking charge made it easier for him to go along with it. “Tell me how you’d suck it.”

Larry proceeded to describe, in intricate detail, how he would give this phantom stranger a blowjob, trying to take inspiration from Henry. “Well first I would…uh…I’d get down on my knees and open my mouth nice and wide and…umm… beg you to use my mouth like a fleshlight.” he said, remembering his training, trying to focus on his pitch. If he sounded like too much of a man the guy might hang up.

“I definitely would,” the creeper said, “I’d shove my 10 inch dick right down your throat.”

Larry highly doubted the man had a 10 inch dick, it probably wasn’t even more than 5, but he didn’t press the issue. “Then I’d take it all the way down my throat, and look up at you with my pretty eyes. I’d run my tongue over your balls with your cock still down my throat. Then I’d bounce and bob on it, slurping and sucking and running my tongue all over it like you’re my favorite popsicle.”

Larry didn’t know where it was all coming from, how had he found the words? He imagined it was an amalgamation of the things he’d learned from porn and class. But it was still surprising that he was able to voice something in this way. He was also surprised at how horny it was making him. His cock was pressing uncomfortably inside his cage. Larry silently told himself it was just because he’d been locked up for 2 weeks, and that it had nothing to do with the conversation he was having.

“That’s good you fucking slut, show me what sounds you would make!”

Larry imitated the slurping and sucking sounds, feeling ridiculous and making the stupid gluck gluck gluck noise. He glanced around at the other sissies, who were too lost in their own conversations to notice.

“Ohh yea! You sound like such a little fucking whore!” the man groaned, there was a noticeable fap fap fap noise coming from his end of the line “Yea…tell me where you want this cum!!”

“I want it in my mouth, Daddy!” Larry said without even thinking. He cringed at how fast it came out.

“I want it in your ass,” the man said, the fapping getting louder and faster.

“You wanna cum in my ass?” Larry asked teasingly. His high voice coming more naturally the hornier he got.

“Yea, I wanna breed you like a bitch.”

“Breed my butthole, Daddy!” Larry squeaked, he could tell the man was close. “Breed it Daddy! Breed it!”

There was a loud, arduous moan over the fapping. Then silence. Larry checked the box to see if he was disconnected, but instead the light above the #5 flashed green, and then disappeared.

Larry assumed the call was over. More red lights started showing up on the previous numbers as more calls came in.

Now that he had his first green light, his first positive reassurance, he felt much more confident in his abilities. He clicked over to line 6.

“Hey there, little faggot” came another gruff voice, “What are you wearing?”

******

By the time Larry got to Daycare, his balls were aching. He wouldn’t have thought that dirty talking random dudes would get him so horny, but practically anything was making him horny these days. The longest he’d gone without cumming back in the real world was 2 days, and that was only because he was so sick with COVID he could hardly move. 2 weeks without an orgasm was absolutely unheard of for him.

“Oooh! Somewon’s excited today!!” said the Sitter changing his diaper. There were ropes of precum sticking from his cage to the inside of the wet diaper when she pulled it open. He whimpered as she tickled his swollen testicles. “D’aww! Is somewon a wittle fwustwated??”

Larry found himself sniffling and mewling on the changing mat. Nodding his head ‘yes’ frantically. He felt so juvenile and pitiful, but he didn’t care.  He had such a ridiculously strong urge to cum he felt like his cage would blow off. But he knew it wouldn’t. It wouldn’t budge, he’d spent the last 2 weeks trying his damndest.

“Pwease wet me cumm, Miss!!” he cried pathetically, tears welling in his eyes.

“Awww! I’m sorry sissy!” Said the Sitter, not showing the least bit of sympathy, “But you’re going to have to find…different ways to make your goo goo’s from now on!!”

She tossed his soiled diaper to the side, grabbing a fresh one and fluffing it to its maximum volume while he writhed on the floor. Tears flowing freely now. He didn’t care how ridiculous he looked, how much of a tantrum he was throwing, and she didn’t either. She waited patiently for him to finish throwing his fit with no concern whatsoever.

“You done, little one?” she asked once his flails descended into silent sobs. He sniffled and nodded, wiping the mixture of snot and tears from his face.

She smiled again, “Lift up.”

Larry raised his hips to allow the diaper to slide underneath. He hated these stupid diapers, he hated this stupid cage, and he hated this stupid place.

“Come here,” the Sitter said after she had him taped up nice and snug.

He clambered into her lap and let her take him in her arms. He actually felt comforted as she rocked him back and forth, shhing and consoling him.

“There there…” she cooed. “I know what’ll make you feel better…”

She took her hand off his back and brought it to her chest. She popped out one of her perfect, perky breasts. Her nipple inches from his nose. “Why don’t you suckle while I pat your bottom and tell you what a sweet wittle sissy you are!! I’m sure that’ll make what’s happening in your cage feel sooo much better!!”

******

Larry’s day didn’t get better at all.

In Analology, they learned about something called ‘poppers’.

“Amyl Nitrate,” Professor Gape said, “It’s proper name, is a chemical substance that acts as a vasodilator. For those of you who don’t know how to break down basic terms, that means it makes your blood vessels expand. When inhaled, it causes more bloodflow to certain areas, allowing your smooth muscles to relax, including those around your throat and anal sphincter.”

Larry didn’t have to be an organic chemist to figure out what they might be used for in the sissy world.

Gape passed out a set of small, unassuming, brown vials. Larry picked his up off the desk, turning the vial back and forth and trying to get a glimpse of the liquid inside. He popped the lid off the top and eyed the contents, giving it a small whiff. It smelled awful. Like dirty gym socks that had been liquified.

“As I said before, poppers are ingested through inhalation,” Gape said. “So if you will all pinch one nostril, and place the vial up to the other.”

Larry and the other sissies hesitantly followed Gape’s instructions, even Henrietta looked reluctant. The smell was even worse as it got closer. Like having a sweaty jockstrap pressed over your face.

“Now, close your mouth and take a deep, long breath through your nose.”

There was a collective whistling as 30 sissies inhaled the pungent poppers.

“Hold it.” Gape growled to the class as they inhaled. “Hold it. Hold it. Hold it. Release.”

Everyone exhaled.

The effect was immediate. Larry felt his head spinning. It was light and hazy, like he’d just huffed paint. His heart started beating rapidly, his vision went in and out of focus. The colors in the room would melt and then resolidify. His head felt foggy, clouded. Like he was losing brain cells by the second, becoming one of those air headed bimbos.

“Again.” Gape ordered. “Other nostril.”

The sissies groaned. Some were rocking back and forth in their chairs, their heads flopping about listlessly. Some were drooling. Some were whimpering. Some were even moaning.

Larry blinked several times to try to clear his head. It worked, kind of. Enough to see Gape glaring at him. Larry quickly brought the vial back to his nose, pinching his other nostril. He took another deep inhale, held it as long as instructed, and let it out. .

This time was more euphoric. His head felt lighter, happier, but dizzier. His horniness gauge got turned up to 11, and it was already high before he stepped foot in Gape’s class.

“Good.” Gape said, “Now, take your finger, and shove it down your throat.”

Every sissy in the room obeyed without thinking. Larry took his middle finger and shoved it down his throat hungrily. A part of his brain knew he would gag, like he did every time a toothbrush, dildo, or cock was shoved down there. But he didn’t gag. He didn’t choke at all. He barely even felt his finger on his tongue. His throat was numb. But it was also eager. Larry put another finger in his mouth and forced the two of them back as far as they would go. His eyes rolled into the back of his head, but he felt no resistance. His gag reflex was gone, but his need to have something in his mouth wasn’t. His cock was pulsing inside his cage. He could feel every heartbeat down there. He crinkled back and forth on his chair as he rubbed his diaper against it. Whimpering around the fingers in his mouth. He used the other hand to rub the front of his diaper. He knew it would do nothing, but he had to have it. He needed stimulation. Anything.

He plopped his slobbery hands from his mouth and put them behind him. Yanking up his skirt as fast as he could and burying his hand into the back of his diaper. He eagerly reached between his crack and searched for his tight little hole. But it wasn’t tight. When Larry pressed his finger into his butthole, it welcomed it easily. Larry had never been able to press his fingers in so easily before. His sphincter was loose and relaxed, welcoming his painted nails in. Larry groaned as he worked it all the way up to the knuckle, but it wasn’t enough. He needed more. He put a second finger in, and then a third, fingering himself right there in the middle of class.

It might have looked out of place, if every other sissy wasn’t doing the exact same thing. All of them were shoving things down their throats and smiling at how easily they took them. Bryan grinned at Larry stupidly. His eyes were misty and he had the biggest, shit eating grin as he pressed one of his biggest dildoes all the way down his throat until the rubber balls were resting on his chin. Bryan held his arms out triumphantly like a sword swallower at the circus.

But just as quickly as the euphoria came, it wore off after just a few minutes. Larry found himself going back to the vial for another hit, and decided to see just how easily he could handle something down his throat, even if he couldn’t handle the incessant throbbing happening in his cage…

******

Larry was still light-headed when he got to Feminine Physique. As much as he enjoyed the effects of the poppers, it left him feeling dumb and drained. It certainly wasn’t something he would want to do often, otherwise he might not have many brain cells left by the time he got out of this stupid place.

He was too lethargic and spacey to do any of the exercises Professor Michaels called for. Which left him wincing and whimpering as he took several swats from her riding crop. Her coach’s whistle making his head ring and pound even further.

Finally, they got to Professor Mars’ Fellatio class. Larry hoped they would do something mundane. Something boring to help him take his mind off his aching balls and his incessant need to empty them.

Instead, they had to watch videos of beautiful women on their knees sucking a cock. Porn. They were watching porn. But Professor Mars was adamant about the sissies watching and critiquing their technique.

“Can anyone tell me what this woman is doing wrong here?” Professor Mars asked the class.

She’s not doing it to me. Larry thought, trying to stop himself from wishing he were the big, black man getting serviced in the video.

He didn’t even hear Henry’s perfect, well thought-out answer because he was too busy focusing on how great it must feel for the man as he spewed hot, sticky semen all over the woman’s eager, open mouth.

Larry caught himself drooling, he wiped it away before looking up to see a different video of another woman going to town on another man’s dick.

*****

“I’ve gotta get out of this cage.” Larry reeled as soon as they got back to the Whoridor common room. “I need to CUM!” he shouted.

“You’re not getting out.” Henry said simply, sighing as he pulled his 3 inch pumps off his feet and rubbed feeling back into them. It made Larry feel good that even Henry was miserable in high heels.

“There has to be a way.” Larry whined.

“There isn’t,” said Bryan, “Trust me. People have tried, but those cages are impenetrable. If you got it from Olivia’s, it’s not coming off, not without the key.”

Larry yanked so hard on his pigtails, he almost ripped his extensions out. “Ughhh I can’t TAKE it anymore!” he screamed. He didn’t care that the other Whoridors were ‘shhing’ him unsympathetically as they buried their heads in bookwork and studies. “I have to cum! I need to cum!”

He looked at Bryan and Henry, “Wait…how come you two aren’t as frustrated as me?”

They each exchanged glances and shrugged, “There are…ways…”

“Watta ya mean?!” Larry asked desperately, diaper crinkling as he shifted to the edge of his seat, “What do you do?? TELL ME!”

Larry realized how much he sounded like some sort of crackhead fiending for his next fix, but he didn’t care.

Henry sighed, “Have you ever heard of a ‘sissygasm’?”

“A what?”

“A sissygasm,” Bryan repeated. “It’s where you make yourself cum by…” he made an indication behind him, like he was motioning towards the backdoor.

It took a while for it to dawn on Larry, he suddenly remembered the day Tyrone came over and made Tom fuck him, when Larry spewed all over his belly without even touching his dick. It was the last time he’d orgasmed since.

“So you’re telling me I have to do it…anally?”

“That’s right.” Henry nodded, shrugging again, “We’re sissies now. It’s…really the only way we get to.”

“Unless you’re a Sluttykins and don’t wear a cage at all” Bryan corrected.

Henry pursed his lips at that, used to be the one doing the correcting.

“Right…so unless we win the House Cup and get our cages off for the year, you’re just going to have to learn to do it the sissy way. Let me see your dildos.”

Larry hesitated, he never thought he’d hear anyone ask him that question. But he shook it off and dug in his bag for his array of phallic devices.

“These are okay…” Henry said, sifting through the various plastic penises, “And you should probably learn how to get off to all of them, but for now you need one that’s sort of hooked at the end.”

Larry didn’t have anything like that in his bag, “Maybe in my trunk,” he said, and they all followed him into the nursery rooms. Larry walked to the front of his crib and started rummaging through his chest of sissy supplies. Finally he found a long, purple, rubber vibrator with a slight bend at the end.

“Perfect!” Henrietta exclaimed, snatching it from him and running her hands along it. She twisted the bottom knob and felt the vibrations hum through her fingers. “Bit too low of a pulse. You could always try holding it against your cage, but with how weak it is it will either take forever, or you won’t cum at all. You’re better off doing it in the butt, I think.”

Larry nodded, a bit disappointed he didn’t get a more powerful vibrator at Dildo Baggins.

“Do you…want my help?” Henrietta offered.

“No.” Larry said immediately, “Thanks…”

She shrugged and handed him the dildo. Larry sat down on his crib and tried to get into a comfortable position. He didn’t want to get caught by a Sitter with his diaper down, so instead he just pulled his soggy crotch to the side. Bryan lubed the tip up for him with a healthy dollop, but when Larry pressed the tip of it to his hole, he realized he didn’t need much at all to allow it to enter.

“You want to angle the hook against your prostate,” Henry explained, “Then turn the vibe on.”

Before his time at Sissy School, Larry couldn’t tell you what a prostate even was, much less where it was located in the body. But his weeks of training told him he needed to press the vibrator up his rectum and towards the back of his penis. He immediately felt the pressure of pleasure. There was no denying it was the male G-spot. But his work was far from done. He rotated the base so that the dildo began to buzz. Larry’s eyes rolled into the back of his head.

He felt a bit awkward with Henry and Bryan standing there watching him masturbate like a woman in heat, but he didn’t care. He rolled over onto his knees and bent over. Pressing the dildo down onto his prostate, working it in and out, short and deep. Biting his lip to keep himself from moaning.

“You don’t have to go in and out,” Bryan said. “Just pressing on the prostate should work–OW!”

Henry had smacked his chest with the back of his hand. “Let him do what he wants. If that’s what he likes, then let him get off with what works for him.

Larry was embarrassed that he defaulted to pounding his asshole, he felt like such a slut. He couldn’t imagine what he might do just to get his cage off, but right now, this was his only hope.

He pressed as hard as he could handle against his p-spot. He could feel a sticky residue forming inside his cage as he leaked but–-while it felt good—he hadn’t achieved anything resembling an orgasm or relief.

He writhed around inside the walls of his crib for over 15 minutes, trying different angles, pressures, speeds, everything.

“Are you sure you don’t want my help?” Henry asked, “I’m pretty good...I do it to myself almost every night, I’m sure I could make someone else–”

“No.” Larry said exasperatedly, sweating from the exertion and frustration, “No…I’m…fine. I’ll…get it…”

Larry didn’t understand. He was able to cum hands free just from getting fucked by Tom, and he didn’t even know what a sissygasm was back then. What did it say that he was only able to cum when a real dick was in his ass?

“Maybe we should give you some privacy…” Bryan suggested, and he and Henry exchanged nods as they headed off. “Good night, Larry! Good luck!”

“Good luck!” Henry echoed, still biting his lip and wanting to help.

They left Larry alone in his crib. Grunting and groaning as he tried his best to force himself to have anything even resembling an orgasm. He screamed into his pillow, put his paci in to muffle his sounds and soothe himself. But no matter how much he jammed the dildo in and out of himself, pressed it against his spot, and tried to think happy, slutty thoughts, he just couldn’t make himself go. His cock was aching inside his cage with no signs of relief in sight.

“Ready for bed, little one?” A Sitter said behind him. It was the red-headed girl from the first day he got here. She was the one that fed him his first meal as a sissybaby. Larry faintly remembered her name was Ariel.

Larry sighed, pulling the vibrator out of his ass and laying it down next to him.

“Looks like you were having some fun!” She teased, taking his hand and leading him through the rows of cribs to a changing table.

Larry’s balls were throbbing as he waddled beside her. She didn’t seem perturbed by seeing him masturbate at all, just helped him on the table and giggled as she squeezed his soaked padding.

“Wooks wike somewon had a visit from the sog-monster!!” she jeered, tickling him up his sides and forcing him to smile no matter how much he didn’t want to. “Let’s get the wittle sissy changed, shall we?”

She peeled the tapes off with expert precision, like she’d done it thousands of times. Which, depending on how long she’d worked here, was probably an accurate estimate.

“Hmm, somewon’s got a sticky dicky!” she giggled as she tapped the hole of his cage and watched the clear ropes of precum stick to it. No matter how much Larry may have leaked into his diaper, he certainly didn’t feel any better. If anything, he felt worse. His balls were blue and his thoughts were hornier than ever. He felt like he was in a constant haze of high libido, and the beautiful, bouncing boobs in front of him did nothing to help matters.

“Let’s get you in a fresh diapy, wittle baby!!!” Ariel cooed. Pulling his pissy pampers off and replacing them with a fresh one. Larry just watched the ceiling with his arms crossed as he let the woman poof a cloud of powder, pull the new diaper up, and tape it tight.

“Bedtime!” she grinned.

As they were walking back to the cribs, the lights were turned down for their 7:30 bedtime. The room was mostly dark other than the glow coming from the nightlights. The hypnotic voice started playing over the speakers, and the mobiles above the cribs started spinning.

“Sleep tight, little one!” Ariel said after ‘helping’ him into his crib, pulling up the railing and clicking it shut.

Larry grabbed his blanky and put his paci in his mouth. For some reason, he hadn’t been able to sleep the last few nights without it. He watched his mobile spin above him. Rainbows, unicorns, and phallic shapes swinging and swirling. He was still upset he didn’t get to cum. He sighed, turning over onto his side, but something felt weird inside his diaper. Something square and stiff pressed into him. Larry reached into this diaper and pulled out the bizarre intruder. It was a small paper note, folded into a rectangle.

Larry had no idea where it came from. Surely Ariel would have noticed it while changing his diaper?

He unfurled it and squinted his eyes to read it in the darkness.

If you want to cum, visit the Sitters bathroom on the 4th floor in the Wimpy Wing. Perhaps I can help you out!

– Ariel :)

To Be Continued