Sissy School Ch. 08 - Frustrations

"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.