wittlesissybaby
Chapter 5 - Ding Ding Dingaling
Published: November 19th 2023, 4:14:12 pm
“How’s the water, queer-bait?” Caleb asked.
But the boy didn’t answer. Just gurgled and floundered for air in the toilet water.
Caleb pressed his foot on the back of the boy’s head, hitting the lever to make it flush. “I’m sorry, f@gg0t! I can’t hear you…”
Adam tried to get away, but Caleb and his cronies held him firm. Aaron had the biggest smirk on his face, high-fiving Caleb like one of them hit a homerun or something.
“Please! I’m not hurting anyone!!” Adam cried between breaths of fresh air.
“Being gay is a sin!” Caleb growled. “You’re not only disgracing my Father’s name, you’re converting other queers to do the same thing!!”
Caleb wasn’t even that religious. He didn’t think much of a God, but he did sometimes have…other…thoughts. And rather than admit it or grapple with it himself, he took out his frustrations on others, and covered up his aggression and resentment with some loose interpretation of a book written thousands of years ago.
He gripped Adam’s sopping wet hair, yanking him upward so that he could hiss in his ear. “What exactly were you and Kerchek doing in the dugout this morning?”
“Nothing!” Adam squeaked, “Nothing! We were just…just…”
“Just giving each other a mouth hug, weren’t you?” Caleb seethed, “A little sucky sucky, licky licky!”
Adam didn’t even try to deny it.
“Did he cum in your mouth, f@gg0t?” Caleb asked, genuinely curious, but maybe for other reasons.
Again, Adam said nothing. Caleb forced his head back in the bowl.
“Did he. Cum in. Your fucking. Mouth?!”
“Yes!!” Adam gasped when he was allowed up for air. “Yes! He did.”
“Did you like it, queer-bait?”
Adam hesitated for a while, but finally said “Yes…”
“What did it taste like?”
Again no answer, again into the toilet for another flush.
“Salty! It tasted salty!” Adam sobbed. “And a little tangy…”
Caleb, satisfied, shoved him to the floor. He and his best friend Aaron exchanged triumphant smirks, and another high five.
******
Caleb awoke with a throbbing coming from inside his diaper. He clenched his legs, turning as much as the bonds of his wrists and ankles would allow. Even after a week, Caleb still hadn’t gotten used to the chastity cage. The hard plastic was not the least bit comfortable. It often pinched him when he waddled around. It chafed him underneath the base of his balls, and his dick was constantly kept at its most shriveled state. He could hardly remember what it felt like to have a fully relaxed penis, swaying comfortably inside his boxers, or even in the diapers. How he yearned for that again.
Not to mention he was in a constant state of horny. Surrounded by beautiful college girls and pheromones all day.
Caleb shifted again. He also hadn’t gotten used to the feeling of waking up in a wet diaper. He’d stopped trying to hold it in, it was best to just let it go and get some sleep instead of straining all night. But this night was different. He didn’t even remember waking up to pee. Maybe he did, but was just too tired that it didn’t register. Afterall, he didn’t really have to think about it much anymore. Loathe he was to admit it: he’d grown accustomed to relieving himself this way. The mental block he used to have was nothing more than a molehill now.
He tugged his wrists on the straps, wriggling his fingers inside his mittens. The sunlight was peeking through the small window of the basement. Or “dungeon” as it could better be described, if not for the long row of cribs around the room.
Caleb guessed he was the first one awake, as no one else was stirring. The other boys in this sick little game were snoring softly, some even making muted suckling noises over the sound of the hypnotic voice playing on repeat.
You’re a pretty little girl…
You lovvve cock…
You lovvve being a slut…
You lovvve using your diapers…
You’re a pretty little girl…
You lovvve cock…
You lovvve being a slut…
You lovvve using your diapers…
He glanced at Aaron, still sound asleep. He almost looked…happy? No way this shit was having an effect on his friend like that, he must be having a dream about fucking a big breasted bitch.
The straps were growing uncomfortable. Caleb’s diaper was much soggier than he originally diagnosed. How many times had he wet himself??
He wanted out. He wanted out of this diaper, out of these straps, out of this crib, out of this sick little game.
“Wahhhh!! Wahhhh!! Wahhhh!!” he called around the pacifier strapped in his mouth.
He and the other 8 ‘contestants’ had figured out if one of them cries like a baby, they were more likely to have a female Pledge come down and get their diaper changed.
Sure enough, the girls of Theta Iota Theta came down shortly after to awaken the padded losers, tease them for the state of their diapers, and untie them.
But instead of laying down pads for them to lay on and get their diapers changed, the girls smirked as they took the sissies up the stairs.
“It’s Saturday!” One of them said when they got to the landing of the wide open room. “A perfect morning for cartoons and playtime!!”
Once they begrudgingly made it to the landing, Caleb noticed the little wooden accordion circled around the center of the room. A playpen. It was a big playpen. The ‘walls’ just served as another way to patronize them as they could easily be stepped over. The girls removed the sissies’ pacifiers, but nothing else, ushering them into the ridiculous play area. Once they got them all down and onto the mats, the girls exited the room, unable to wipe the smiles from their faces.
Caleb and the other boys didn’t really know what to do. They all just kind of sat there with their legs crossed, eyeing each other. He glanced up at the ceiling. The camera with the redlight constantly on them. Watching their every move. He wondered what they were doing with the footage. Who was this being compiled for? Or was it being streamed? Who the hell wanted to watch a bunch of grown men prance around in diapers and dresses??
“We brought you some toys!!” The girls said, returning with two large cardboard boxes. Caleb was actually a little excited. The only real entertainment he’d really had for a while were these stupid Sissy Games. Everything in between was mundane and boring: cleaning the house from top to bottom, wetting and messing his diapers, begging the girls for a change, having to do whatever humiliating act they could come up with, finally earn a fresh diaper, and get sent back for more cleaning. It was stupid how excited he was to play with toy cars, legos, hell, even stuffed animals or blocks would be a break from the monotony. But when the girls turned the box over, it wasn’t even close to what he was expecting.
An array of dildos clattered against the floor, bouncing and rolling around the mat. They were all different shapes, sizes, and materials. Some had fake balls attached, some even had a suction cup.
“Awww!! You look disappointed!” The girls giggled when they only got a bunch of disheartened, confused looks. “What else would a bunch of sissy gurls get to play with??”
“We suggest you gurls play nice, and have fun with your toys, they may come in handy later!”
And then they left. Leaving the room completely empty other than the 9 boys in their ridiculous outfits and diapers.
No one said anything. The only thing to break the silence were the sounds of exaggerated moans coming from the TV. A cartoon Hentai episode of a big-busted sissy being bent over by a very large man and fucked with her diaper around her ankles, catching all the exaggerated semen spurting and dripping out with every thrust she took.
Some of the sissies paid the utmost attention, others had to turn away, either from disgust, or from getting an uncomfortable swelling inside of their chastity cage.
Chris, of course, immediately rubbed his diaper like he always did. He didn’t seem to have any regard for it being futile, his hand must’ve just been accustomed to that motion.
It was Ben who picked up a fake dick first. Caleb scoffed, knowing he would. He still hadn’t forgotten what Ben had said earlier: he liked this stuff. Openly. Like, not even afraid to admit it. Caleb turned up his nose at that. Who in their right mind would let people know you like having a dick in your mouth?
“What?” Ben shrugged, pulling the jelly dildo from his throat. “You heard ‘em. Whatever we do with them may come in handy later!”
Caleb was still revolted. There was no guarantee they were going to have to put dicks in their mouths, but the possibility didn’t exactly frighten him either.
Eric eyed the dildos, nostrils flaring. He looked more disgusted than Caleb. He let out a deep sigh, then scooped one up. He hesitated for just a second, amped himself up like he was about to rip off a bandaid, and stuck it in his mouth. To Caleb, it looked ridiculous. A big ‘macho’ man like Eric wrapping his lips around a big fat dick, taking it as deep as he could until he was gagging and choking.
Caleb scoffed again, turning elsewhere so he didn’t have to see it. But inside his diaper, he felt the slightest of twinges.
******
“It’s reward day!” Lauren exclaimed to the gathering of sissies and onlookers. Everyone was surrounding the ‘staging area’. A raised platform with colorful walls and lights in the background. Additionally–and probably most importantly–there were 9 dildos suction-cupped to the paneling. A digital sign illuminated above them, all displaying the number 100.
Fuck. Caleb thought. I should have listened. I should have practiced.
“This challenge is very simple.” Lauren explained, “Each contestant will get on their pathetic little knees in front of a rubber dick. They must take it allll the way down their throat until their nose presses the little red button. Whoever does it 100 times first, wins reward!”
The crowd cheered, already exchanging bets and money, eager to watch the action.
“As some of you know, our sissies have spent this entire week wearing chastity. Some have…handled it better than others. But almost all of them constantly have a sticky diaper from all the leakies!” The men in the mob groaned, perhaps sympathizing with their situation, while the women thought it was the most adorable thing, ‘awwing’ and laughing in amusement.
“Whoever completes their countdown first will win an unlocking, and what I like to call a ‘two-finger tuggie’ from one of our beautiful Theta pledges!”
All of the sissies perked up at that. No one was going home, but this was gonna be the next best thing. Caleb and Aaron eyed each other, always the competitors, and furrowed their brows in concentration.
“Everyone understand the rules?!” Lauren called.
“YES!!” The crowd shouted in unison while the sissies nodded, determined.
“Then let’s get our little sluts to their proper positions!”
The sissies stumbled awkwardly at first. Their hands bound behind their backs, wearing nothing but a bonnet and a diaper with their contestant number drawn on the butt.
The dildos came in an array of sizes and colors, but they all had prominent veins and fake rubber balls. Apparently it was first come, first serve, as the sissies rushed to find the one that seemed the easiest to handle, and perhaps a little more aesthetically pleasing.
Caleb wished he had figured out to claim a cock sooner. He was left with probably the largest one, and of course, it looked like a big black dick.
His knees immediately screamed at him as he knelt down. The flashing lights threatened to blind him. It was like being front and center on a carnival show. The dick looked menacing. It wasn’t so much long as it was girthy. The task seemed impossible, but why did it also seem somewhat intriguing?
“On your marks!” Lauren called, holding up her airhorn. “Get set. GO!!”
Shouts, jeers, and cheers came from the crowd. The sissies, however, were a bit reluctant. Other than Ben, who was already working the cock into his mouth, everyone else seemed less than enthused.
Ding!
A little bell sounded. Ben had shoved the cock all the way down his throat until his chin was resting against the balls and he could smash the red button with his nose. His counter clicked down to 99.
This kicked everyone into gear. Several other sissies jumped on their dicks, jamming it into their mouths. It wasn’t long until the panel was full of the sounds of choking and gagging.
Caleb leaned towards his, it was even more intimidating up close. He had to do it. If, not only to win the competition, but because he was somehow drawn to it. Was it the hypnosis? Whatever was in those stupid bottles? No…he’d had these thoughts for a while. But did all that make it more pronounced? Or was he just tired of shoving it all down?
One thing’s for sure, when he opened wide and wrapped his lips around the head, it didn’t feel bad. In fact it almost felt…right? Having something filling his mouth. Something long, thick. It appeased his oral fixation, but it also awoke something within him.
Ding!
Ding!
Ding!
The bells were starting to ring faster now. Eric gagged next to him, but fought through it enough to press the button. He gasped and spat when it withdrew, huffing and puffing for air.
That seemed to be a common occurrence, Aaron wasn’t having too much luck himself.
How hard could it be? Caleb thought, getting a load of confidence now that he had braved the hard part of just getting the thing in his mouth.
But that wasn’t hard at all, not even close. Caleb quickly realized it took very little to trigger his gag reflex. It only made it about 3 or 4 inches in before he felt his body convulse at the intruder. Bile ran up from his stomach, an acidy taste filled the back of his mouth. The dildo didn’t bend the way he wanted it to, just felt like it was going straight into the back of his head. If he had the use of his hands, he might be able to angle it down. Instead, he was left tugging at his bonds and whimpering helplessly with half of a dick in his mouth.
Ding!
Aaron got one. It seemed to take everything he had, but he got it. It gave Caleb a new sense of competitive confidence. He took the cock out and gathered a deep breath of air, stared down his bobbing obstacle, and shoved it in his mouth. His strategy was to go fast, get it in before his gags kicked in, but that only made it worse. A glob of spit ran down his chin, he couldn’t even wipe it away with his cuffed hands, just had to let it rain down his chest like a drooling AB.
Relax. He thought. Embrace it, hunger for it, worship it.
He didn’t know where the voice was coming from, but he decided to listen. Caleb had always been interested in girls, but if the last few weeks had proven anything, it was that he always had a lingering curiosity about the other sex too.
This time he took it slow. Closed his eyes. Even hummed a bit. He still gagged, but he didn’t let that stop him. Tears ran down his cheeks as he forced himself forward. The balls were getting closer, his prize, the big red button within reach. He thought he might throw up right then and there, but he persevered, holding himself together, smushing his nose into the little knob.
Ding!
He did it! His counter clicked down to 99. He glanced at the other sissies, none of them were past the 90’s yet. He still had a chance.
“Earn that orgasm, you little sluts!” One of the Thetas in the crowd called.
This got everyone going. More and more dings came in succession.
Ben seemed more worried about giving the cock a good blowjob as opposed to just deepthroating like a pornstar. For being turned on by it, he didn’t seem too worried about getting his numbers down.
Gluck! Gluck! Gluck!
Ding! Ding! Ding!
Someone down the row was racking up points. It was Chris. Always eager to masturbate. If his hands were untied, Caleb had no doubt he’d be rubbing his diaper in rhythm with his enthusiastic slurping.
Caleb had a new appreciation for pornstars. How were they able to shove massive dicks down their esophagus without puking all over themselves?? After only 7 button smashes, Caleb was about ready to tap out.
Bzzt!
A sharp zap shocked him from behind. Caleb turned to see Sarah holding a cattle prod in her hand, glaring at him threateningly.
“Get moving, sissy!” She growled, “Or I’ll zap you again!”
She didn’t have to tell him twice, that shock was not fun at all.
The contest probably took longer than everyone originally thought. The sissies were winded and gasping for air like they ran a marathon. Covered in drool, sweat, tears, and in one case…vomit.
“Awww! The wittle diaper boy spit up!” A girl from the crowd cooed at Aaron. He looked incredibly embarrassed at the small bit of puke running down his chin. He spat and sputtered, trying to use his shoulder to clean himself up, but it was futile. A zap from the cattle prod got him back to work.
“10! 9! 8!” The crowd shouted in unison as it came down to the wire. Caleb wasn’t even close, still at 54. The contest was down to Ben and Chris.
Ben had dropped his enthusiasm for the chance at getting the reward. Focusing now on deepthroating as much as he could, but that didn’t stop him from moaning and groaning the whole time like a whore.
“It’s close!” some guy exclaimed.
“Number 6 has it in the bag!”
“Na no way! Look how desperate seven looks! And he’s catching up!!”
Chris was gluck, gluck, glucking like his very life depended on it. With how much of his life he spent masturbating, it probably was. His numbers were dropping faster than Ben’s, even though Ben had the lead.
A cacophony of excited sounds came from the audience. The final moments had arrived.
Ben worked himself onto it, choking and sputtering still, but not as much as when he first started practicing yesterday.
However, it was Chris who finally found the strategy. Instead of going back and forth on the cock, he just held his face as deep as he could on the balls, and pressed the button as many times as he could with one breath.
“5!! 4!! 3!! 2!! 1!!”
Bells and whistles rang out. The dick in front of Chris whirred. When he came up for air, a huge blast of white liquid shot from the rubber cock. Covering him from head to diaper in pearly, gooey slime.
“And we have a winner!!!” Lauren called like a carnival announcer.
The crowd simultaneously erupted and groaned. Those who made the proper bets were happier than the contrary. While their winnings were distributed, the girls brought a chair up onto the stage.
“Come on Chrissy-poo!!” one of the girls cooed, taking him by the slimy hand and leading him over to the pedestal. “It’s time to collect your prize!!”
Some of the patrons left, not wanting to see this part, others gathered even closer.
The spotlights shone brightly down on Chris as he sat his soggy bottom onto the chair. He didn’t protest as two girls pulled his cuffed arms behind the chair and secured them to the wooden legs. In fact, he was smiling gleefully when they untaped the front of his diaper, opened the flap, and exposed his tiny, caged penis to the entire crowd.
Some of them clapped, all of them laughed, and some of them cooed.
“Awww!! It’s so tiny!!”
“Looks painful…”
“Pathetic!”
“Look how purple his balls are!!”
“They’re so swollen!!”
“Hasn’t it only been a week?!”
The hushed jeers and whispers ran together, but they ceased when Lauren strode up, brandishing the key. She held it up to the light like Rafiki displaying Simba on his birthday. Many of them continued to gawk and stare as she brought the key down to the tiny lock, their interest piqued. Most of them probably had little to no experience with chastity devices, few had even heard of them. They watched with college-infused interest as Lauren wriggled the key into the lock, and pulled out the tiny pin.
They gasped as the front of the cage fell away, and Chris’ penis immediately grew erect.
Chris was gasping too, trembling. Not in fear, but in anticipation. He tugged at the cuffs, probably not in an attempt to escape, but more to try to get his hands back on his penis like he always did, but he couldn’t. Two girls kept him down on the chair by his shoulders.
“Ready for your treat you little bitch?” Lauren teased.
“Mhmm!!” Chris nodded so frantically he sent droplets of the fake, goopy jizz juice across the room. He struggled and squirmed desperately. Impatiently.
“PLEDGE!” Lauren yelled dramatically.
From the crowd of Theta girls, a shy, timid one emerged. She took an audible gulp, held her head up, and stepped forward onto the stage.
“While we do enjoy our little Sissy Games,” Lauren explained to the crowd, “Our Theta pledges have little competitions of their own too! Unfortunately, Miranda here, lost. Not in anything crazy, just a friendly round of bowling, but hopefully she’s able to handle balls much better this time around!”
The audience laughed at the awful joke, but the implication was obvious.
“You’re sure you’re okay with this?” Lauren muttered to Miranda so that only she and Chris could hear.
After a moment’s hesitation, Miranda nodded, and smiled. “I’m ready!”
Lauren gave a very proud wink, then turned back to the crowd.
“Miranda will tug on the little Deepthroater’s dingaling for a maximum of five minutes, or until he orgasms–whichever comes first. He will be–”
“Yea yea, we got it! Just get on with it!” An impatient guy called.
Lauren looked perturbed, but kept an even face, and shrugged. “Off we go then…ready, set, go!”
Another Ding sounded and a timer began counting down from 5 minutes.
Miranda crouched down next to Chris, as if she wanted to inspect the little 4 inch thing she had to play with. She watched it bob up and down, twitching, throbbing desperately.
“You only get two fingers, okay?” Miranda giggled. She seemed more excited now that she had a helpless, blubbering bitch boi at her disposal. Power is a wonderful drug.
She placed her hand down at his knee, slowly sliding it upwards to gather some of the goo to use as lube. She worked it between two of her fingers, smiling when she was satisfied with the amount of slick, and brought it to the dancing dick.
But just as Miranda was about to pinch her fingers around the head of his penis, Chris began to convulse.
“Is he having a seizure?” someone gasped.
“What is he…?”
“Holy SHIT!!”
The chair legs rocked and creaked as Chris spasmed, spewing spurt after spurt of semen across the stage. Miranda had to dodge out of the way to keep from being hit. Every jaw in the room dropped to the floor.
“Did he just…?”
“No way!”
“No fucking way!!”
“Did you even touch him?!” Lauren asked, and Miranda threw her hands up in innocence.
“No! I didn’t touch it! I swear!” she exclaimed.
But Lauren wasn’t mad. Instead, she acted like it was the most amusing thing she’d ever seen. The crowd soon joined in her cackling laughter.
“Well…there you have it folks! I guess our sissy has earned his prize! And it only took 17 seconds to…’hand’...it out!!”
Some of the onlookers were stupified. Others seemed like they’d seen something similar before. Others were practically in tears from laughing so hard.
Chris was in literal tears, for a much different reason. Blubbering like a BB that just got a toy taken away from him.
“Back in his cage please, ladies!” Lauren called without the least bit of sympathy.
Several giggling Thetas swooped in, using their fingers to carefully put Chris’ deflated member back in its little metal prison.
This really got him going. His cries turned to blood-curtling shouts and pleas. It took several of them to hold and restrain his thrashing body.
“No!!! Please!!! Don’t make me go back in there! I can’t handle it!! Let me cum just one more time! Please!! I need it! I neeeed it! MMPMPHHH!!! MMMPHH!!”
A very large penis pacifier was stuffed and tied into his mouth.
“That’ll shut you up!” Lauren said. “Seems like you like things like that down your throat anyway…”
Chris continued his muffled blubbering as the cage and diaper were readministered.
“And that’s our show!!” Lauren called back to the crowd, throwing her hands out wide dramatically, “We hope you enjoyed it! Come to our elimination game tomorrow, where the stakes get higher, the humiliation gets heavier, and the tears become even more real! Stay tuned!!
To Be Continued
This was going to be a long Chapter, but would have taken me a long time to finish up, so I decided to split and give you guys something to read now while I finish up the rest. I may have to come back and retcon when it's all said and done, but I hope you enjoyed this segment!