Sorority Boys Ch. 2 - Holding Out for the Drop Out

“Wakey wakey babies!!”

The light stung Caleb’s eyes as they flicked on. He felt like he’d just closed his eyes and started resting only moments before. The collective groaning of the other diapered boys told him he probably wasn’t the only one that didn’t get much sleep that night.

Caleb glared at Chris, his crib-mate, whose avid masturbation with Caleb as a humping post was the primary reason for his lack of rest. Chris avoided eye contact, trying to pretend like nothing happened.

“Good morning sleepyheads!” Sarah cooed over the bars of the crib, looking down at the two bound ‘babies’. “Did you two have fun last night?” She squeezed the front of each of their diapers, obviously checking to see if they had any ‘accidents’. Caleb was ashamed to say he grew excited inside his diaper almost instantly at her touch. She was a very attractive brunette with a cute, mousy nose and very faint freckles. Either she didn’t notice what Chris had done in his diapers all night long, or she didn’t care as she started undoing the clasps that secured their mittens to the bars of the crib. With their arms free, Caleb and Chris could finally roll out of their forced embrace. They flexed their cramped and stiff appendages, jaws aching from the paci’s still in their mouths. Thankfully Sarah loosened the ribbon around their heads and allowed them to fall and hang as they sat up.

Caleb still wasn’t used to the bulkiness of the diaper. Despite the cold, he’d seemed to spend the night sweating inside his Pampers. His still erect cock felt clammy and gross as he and the other pledges were led upstairs and back into the large open room of the house.

Caleb was expecting to get this stupid diaper off. But the 14 highchairs in a semi-circle in the room told him this whole ‘baby’ thing was far from over.

They were lined up side by side. Girls smacking their padded butts to get them into line.

“How was your first night as a Theta, boys?” Lauren said, strutting back and forth in front of them. The padded pledges collectively grumbled and whimpered in response. Lauren didn’t seem to care.

“Yesterday you proved to us what little babies you are by being immature little brats and attempting to steal our panties. Then crying like blubbering babies when we punished you for it. So we thought it only fitting that you be treated like the babies you resemble.”

There was a lot of protesting from the boys at that.

“You kidnapped us!”

“You can’t keep us here!”

“I don’t need to wear a stupid diaper!”

“This isn’t fair!”

But Lauren just smiled. “I see some of you want out of your pretty Pampers and would like to go home?”

There was a collective “Yes!” From all the boys.

“Fine,” Lauren conceded with a smirk, “then all you have to do today is prove to us that you don’t need your diapers.” The guys looked befuddled at that, so Lauren continued. “If you go number 1 and 2 in your diaper today, you obviously still need them, and need to stay. But the last one to hold out, the one that keeps their diaper clean or dry the longest, gets to go home. Back to your old life and old underwear…whatever underwear you may choose…”

The girls laughed at that.

“I see some of you are already halfway through using your diapers!” Lauren chided, “I see a blue line on the crotch of some of you!”

She was referring to Chris, who obviously made his blue line appear with the sticky messes he spurted last night. Another, Alex#12, also had a blue line on his diaper. He must have had fun in it last night too. But it was #8, Matt, that drew the most attention. In addition to his blue line like the others, he had a soggy, yellow stained crotch to accompany it, and a flushed face to boot.

From an early age, Matt had always struggled with bedwetting. It lasted all the way up until he was age 12. It got to the point his mother threatened to put him in night time diapers. If only she could see him now.

Even in highschool, when Matt would get really drunk he would sometimes have accidents. But the worst was when he woke up in a wet bed next to his highschool girlfriend. She told everyone at school about it, and he was never able to find a girl willing to date him again.

Apparently Matt’s body felt comfortable enough in the diaper last night to let loose once again. He was immediately overcome with shame when he woke up this morning to the somewhat familiar wetness, which only was exacerbated by everyone pointing and laughing at him now.

“Now…” Lauren redirected, “you boys look hungry!”

The guys were shoved forward, each to an oversized highchair. The table top was clicked open and they were forced to sit down. Matt cringed at the feeling of his soggy diaper squelching against his bum.

Their mittened wrists were secured to straps underneath, as well as their ankles. Who made all this stuff? Where did they get it all?

They didn’t have much time to dwell as a large box of baby food was brought out.

“Pledges, please take a couple jars and a spoon”, Lauren ushered.

It took the boys a while to realize she wasn’t referring to them as the pledges, but a certain set of girls.

The freshmen females each grabbed a spoon and sat in front of a diaper-wearing captive. Bibs were handed out. Each with the respective number on them.

Caleb cringed as a very attractive female named Danielle sat in front of him, tightly wrapping a bib bearing the number 15 around his neck and under his dangling paci.

“Girls, this is going to be a little competition for you too…” Lauren explained. “Whoever can get their baby to eat the most jars of food in 30 minutes will get automatic entry into our prestigious Sorority!”

The girls’ eyes lit up at that. There was a certain determination in their eyes now that made all of the pampered pledges gulp in fear.

“Are we ready, girls?” Lauren asked the crowd. The girls gripped their baby spoons tightly, nodding.

“Ready…set…GO!”

There was a clanking of lids as the jars were unscrewed. The girls scooped up as much of the mushy peas, carrots, bananas, or whatever the contents of the random jars were and pressed it to the lips of the boy in front of them.

Every single guy had their lips pursed, shaking their heads back and forth like a defiant toddler. They either didn't want to eat the disgusting texture of the food, didn’t want to taste it, didn’t want the humiliation, or didn’t want to be too full to lose their diaper holding challenge.

So the girls had to adapt a strategy.

Some went with a sweet, motherly method.

“Come on wittle guy!” Cooed the girl in front of 11, “open up for the airpwane!!”

Some went with a more forceful method. Pushing the mush in anyway, and scooping up whatever dribbled out and shoving it back in. Some used the handy ‘hold-the-nose’ method, waiting for them to open their mouth for air before pouring the spoonful of gunk inside.

There were guys spitting up and spewing the contents all over the girls. Which was met with several slaps to the big baby’s face.

Danielle adjusted her horn-rimmed glasses and spoke to Caleb like a person. “Look…I know you don’t want this any more than I do, but I need to get into this Sorority if I want any shot at my dream career. So will you do this for me? Please?”

She held up a spoonful of pureed peas. Caleb turned up his nose, but he figured the more he could get on these girls’ good sides, the better. He opened his mouth and Danielle smiled thankfully as she pressed the spoon into his mouth.

Caleb immediately gagged. He always hated peas, and this texture did nothing to help. “I…I'm sorry…I can’t…” he said apologetically.

“Come on! Yes you can!” Danielle coached, scooping up another bit and bringing it to his lips, “you can do it! Come on, baby!!”

Caleb’s eyes watered as he tried to gulp down the green mush, Danielle catching it as it dribbled down his chin and bringing it back up. “There you go! Swallow! That’s it!”

Next to them, #13’s feeder was getting frustrated. Abandoning the tiny spoon and using the penis paci instead. She scooped up a big glob of bananas with the head of the rubber penis and shoved it in 13’s mouth. “That’s right! Lick it off you fucking faggot!”

The girls were getting anxious now. Looking around to see that some had already managed to get their guy to finish two jars.

#14’s girl got desperate. “If you win, I'll make you cum!” She said, and 14’s eyes went wide. There’s no better way to motivate a guy than through his dick. 14 opened his mouth and willingly started gulping down runny carrots by the spoonful.

The other girls saw how effective this method was, and started adopting the same tactic.

“If we win, I'll give you a blowjob.” Danielle told Caleb, crooking an eyebrow. To which Caleb obliged.

But down the line, #7 was already on his 5th jar. The girl was rubbing the front of his diaper up and down under the tabletop and Chris was gulping down spoonfuls as fast as she could scoop them. “That’s it, baby! You like it when Mommy rubs your wittle pampurrs don't you! Yesss you dirty boy!! Eat up! That’s it!”

How is that guy still horny?! Caleb thought, did he not have enough fun against my leg last night??

Now all the girls started rubbing diapers too. Though the one across from Matt was a little hesitant to touch his pissy pampers.

Alex’s girl had a hard time finding his microdick through his padding. But once she did, he was squirming and spurting within seconds. Losing any interest after that.

After about 8 or 9 jars, the boys were getting full.

“3 minutes, everyone!” Lauren announced.

The girls growled in vehemence as they forced all they could into the boys’ groaning mouths.

Danielle was growing frustrated at Caleb’s lack of enthusiasm, Caleb was growing frustrated at his inability to feel Danielle’s hand rubbing his dick through all the padding. When Caleb stopped eating, Danielle stopped touching his pampered penis. Until Caleb forced down another bite, and she’d smile, and reward him with another few strokes. Setting the empty jars to the side and opening the lid for more.

“1 minute left! Give it everything you got!”

Caleb was right on the cusp of cumming. He opened his mouth hungrily. Not for the food, mind you, but for the chance to cum. It was amazing what a horny brain would do.

He could feel the pressure building. If only the stupid diaper wasn’t in the way and he could get some proper stimulation! There…right there…he was close…here it comes!!”

“Time's up!!”

Caleb whimpered as Danielle immediately snatched her hand away. As if that were the last thing she wanted to be doing at the moment. The girls looked around at the other trays, trying to assess how many jars they’d gotten through. While the boys assessed who got to cum during that whole predicament. Some were resigned to their after-orgasm relief. While others were pent up in frustration.

“Let’s tally the scores, shall we?”

Sarah and Lauren went around with a clipboard. Silently counting the number of empty jars on the trays and keeping their faces stoic and without bias. Caleb thought he made it through a ton of jars, 23 by his count. And he felt every one of the contents sloshing inside him.

“We have a winner!” Lauren announced, “With a whopping 27 jars, the winner is…Kayla!!”

The girl in front of Chris got up and screamed. Fanning her hands in front of her face to keep from crying.

“Congratulations! You’re the newest official member of the Theta Iota Theta Sorority!!” Lauren smiled and gave her a big hug while the other girls reluctantly clapped. They all gave their respective feeding partners the evil eye. Chris smirked slightly, obviously forgetting that just because he ate the most jars (and consequently came the most in his diapers) that he would get to go home. He didn’t.

The expression in the room changed as Kayla went to join her new sisters.

“Now, I hope you boys saved some room for dessert!” Lauren declared. She snapped her fingers, and as if it were rehearsed, someone immediately brought in a tray full of large baby bottles.

The empty jars of baby food were cleared away, and replaced with the giant bottles. Danielle’s face shifted from disappointment to a devilish grin. Caleb knew she was about to get some form of payback.

“Now I would say this is another competitive portion,” Lauren began, “because I know how you boys like to compete, but I think it’s more fun forcing it down and  watching you squirm!”

Danielle grabbed the bottle with a wicked grin. Caleb tried to beg, to plead, he was so full, there was no way he could possibly gulp all that down. He tried to turn, tried to shake, but the restraints held him tight to the chair. He could do nothing as Danielle put him in a headlock and pressed the nipple of the bottle to his mouth. Caleb tried to resist but it was no use, the rubber teat just spewed more liquid into his mouth every time he wriggled. It tasted like milk from a cow, but it had a slightly off-putting bitterness to it that Caleb couldn’t place.

He relaxed and accepted his fate. Trying to manually create more room in his stomach to accommodate all of the liquid. Looking around at the other contestants, he  saw they were mostly in the same boat as him. Some still squirming, others being docile and determined. Chris, the winner of the food eating challenge, seemed rather perturbed that Kayla no longer deemed it fit to rub his diaper anymore. He had a pretty pouty face as he begrudgingly sucked down his bottle.

“Oh goodness! He spit up!!” The girl across from contestant 8 called out. It was Matt, the bedwetter. He had just sputtered and spewed some of the milky fluid all over himself. He must have felt extremely infantile being mopped up with a bib in his pissy wet diaper.

Caleb was about halfway through his bottle now and felt like he was about to explode. Danielle was unrelenting though, hardly letting him come up for air, fixing her stern gaze on him as she made sure he continued to suckle on the giant bottle. There was pressure building in his bladder now, amidst all the other feelings of fullness overcoming him. His urge to pee did nothing to help his discomfort. He decided it was only a matter of time before he pissed anyway, so he might as well get it over with.

But that was easier said than done. Not a lot of people are used to peeing in anything other than a toilet. So to try to do it in a diaper–while strapped to a chair and having liquid pouring down your throat—was no easy task. Caleb wriggled a bit, trying to get comfortable. He screwed up his face as he concentrated, trying to force himself to pee. Anything to ease his disconcertment. Finally he managed to leak some out, then the whole stream started.

Danielle must have noticed his face. “Are you peeing?!” she announced louder than she needed to. The onlookers gasped as if this were a milestone they had to witness. Danielle plopped the bottle from Caleb’s mouth and scooted her chair back so everyone could watch him flood his diaper. Danielle poked and prodded his yellowing crotch teasingly.

“You are going pee pee in your diapy, aren’t you?! You little loser!!” she cackled.

That must have opened the floodgates, as soon there were other girls exclaiming that the boy in front of them was peeing too. Sighs of relief and whimpers of shame could be heard coming from down the line as blue lines formed between their legs.

Caleb immediately regretted his decision. While it was nice to take a little pressure off of his insides, he was now inside a very wet and warm diaper. It felt even more bulky between his legs now. No matter how much he shifted his weight, he still felt icky and pathetic. 19 years old and he just pissed himself in a pair of Pampers!

He tried to focus on the bottle. It was almost done but he felt like he had no more room left. He figured he’d make one last request to incentivize him.

“Will you touch my dick if I finish the bottle?” he asked Danielle around the nipple. It sounded more smooth in his head.

Danielle burst out laughing and scoffed, “Piss off, diaper boy! Oh wait! You already did!! Haha!!” she guffawed at her own joke.

Caleb shrugged in shame and sucked the last few drops of the bottle out. The sound of air going through the tiny hole instead of liquid was music to his ears.

“Does the baby need a burping?” Danielle asked menacingly. Before Caleb could protest she was standing up and hammering him in the back repeatedly. Taking out whatever was left of her pent up aggression from earlier.

Caleb let out a huge belch and was surprised that nothing came up with it. He had to admit that he did feel a little better. But not much.

As the boys finished their ba ba’s, they were let out of their restraints and the trays of the highchairs were removed. They were allowed to stand up, groaning as they did so, those with wet diapers caught off guard by the drooping weight as gravity took over. The girls shoved the boys forward until they were lined up in a semicircle. The boys had their legs spread to accommodate the bulkiness of their diapers.

“And now comes the final portion of our challenge…” Lauren revealed. With a wave of her hand girls started filing in wearing scrubs, each pushing a metal rack on wheels with a large red bag dangling from them.

The boys trembled, some apparently aware of what the bags were, others mystified as a girl lined up behind each one of them. Each bag had a long tube attached to it with a little valve on the end. When the nurses grinned menacingly, it became apparent to everyone what their intentions were.

“Now, are you going to make this easy or do it the hard way?” The girl behind Caleb asked. Caleb was too busy being full of mush and milk to protest, so he just bent over as much his swollen belly would allow. He felt the back of his diaper being pulled to the side as the girl peeked in with a finger or two, snaking her way down his backside with the little tube. She poked and prodded until she found purchase, pressing the valve into his puckered rectum. He gasped as it entered, never having anything up his ass before. The girl turned the knob on the valve and Caleb felt a warm rush within him, like he was being inflated.

#6 tried to take off running before the enema tube could be placed in him. He didn’t get far though, as the 15 or so onlookers tackled him and held him down so his “medicine” could be administered. Once he was full,  he was lifted and placed back in line. His kicking and screaming caused the enema to leak out, and the back of his Pampers were soaked, in addition to the blue line that formed from him peeing in them before. “Looks like we’ve eliminated our first contestant!” Sarah called as all the girls cheered. Number Six was led back down to the basement to be forced to compete another day.

Lauren turned back to the inflated pledges. “We suggest you don’t do a whole lot of moving. Unless you’re really enjoying your stay here, and would like to keep having fun in our little competition!”

The boys grumbled. Straining to keep the enema inside them. In addition to everything else that was swirling within them. The girls laughed and cheered and videoed the 13 remaining pampered pledges in the room.

“We got a mushy diaper over here!” a girl called.

“One here too!”

“Awww!! Look!! This one’s squatting down to make a mushy pushy!!”

The boys started dropping like flies. They could only strain and clench for so long. Doubling over on themselves from the cramps before exploding into their diaper.

Only Caleb #15, Eric #13, Brad #3, and Donald #2 remained. Caleb was standing straight as an arrow, trying to clench his legs together to keep the strain off of his rectum. His diaper was wet and cold now, and it felt gross against his penis and legs. All the boys were shivering from the cold and humiliation.

The girls must have grown tired of waiting, so they started passing out riding crops.

“We just wanna test your focus!” Danielle beamed, smacking Caleb across the thighs, hard. Caleb yelped in surprise and felt a trickle leak from his butthole and into his diaper. He hoped it wasn’t enough to notice. Which it wasn’t, at first. But several swats later forced him to release the floodgates. He was crying on the floor from the shame of filling his diaper when the girls dragged him over to join the rest of the losers.

Brad was sweating visibly. Eric, who’s dick you could see bulging under his diaper, devised a strategy. He reached over to Brad, and gave him a backhanded smack across the belly. Brad, gasped, barely able to control himself, he started reciprocating Eric’s slaps. Each trying to force the other one out. As they squabbled, Donald waddled away to separate himself. Soon the combination of slaps from each other and the smacks from the crops escalated, and both Eric and Brad were left with mushy diapers by the end of it, Donald still safely in the corner.

“And it looks like #2 is our winner!!” Lauren roared, holding Donald’s arm up like he was a sweaty boxer that just won in the ring. “How ironic that the only one to not to go number two in their diaper is our #2 contestant!!”

The girls clapped and cheered. Donald looked absolutely flummoxed. He whispered in Lauren’s ear, she laughed and said “No, you can definitely not use our toilet! But you’re free to go! I’m sure you can find one around the neighborhood somehow. There’s a Zeta House down the street. And they’ll let anyone in if you know what I mean!!”

She mouthed the words sluts to the other girls just in case they didn’t catch her drift. Donald scampered out the door, holding the back of his diapers as if that were the only thing keeping them contained.

Lauren turned back to the group of remaining boys. All wet and messy in their diapers. “Looks like you boys had fun!” she strutted through the blubbering babies, “It may be a good time to tell you that that bottle you all drank was laced with laxatives. So this probably won’t be your only messy diaper today. We also won’t be changing you. Us girls don’t like to change stinky diapers. So you’ll be changing each others’! But first, we want each of you to take turns standing up and telling us how much you love your pissy, poopy Pampers while you rub the front and make a #3 in them!”

*******

After Donald made it out of the Theta Sorority House, he immediately ran back to his dorm room. He had to drop his diaper, squat down, and empty himself twice along the way. He didn’t want anyone seeing him in a diaper, but he didn’t want to get expelled for running around butt naked either. Hazing was pretty common place around this time anyway.

Once he got changed into normal clothes, he headed immediately to the Dean’s office.

“Come in” came a mellow, melodic voice.

Donald stepped into the Dean’s office warily, wondering how he was going to go about this. Sure, he had been caught breaking and entering and trying to steal some panties, but what the girls did was way over the line.

The Dean looked down at him over her half-moon spectacles expectantly. She had a very “sexy librarian” look to her. And even in her mid-fifties, she was still a smokeshow. It made things even more intimidating.

Donald cleared his throat, “Ahum…Dean Pritchett, I just…wanted to let you know about some things going on in the Sororities at your school…”

He proceeded to tell her everything. Admitting his fault in stealing the panties, the spanking challenge, the hazing, the diapers, the competition, everything. Dean Pritchett had a very stoic face the whole time. She waited for him to finish, then sat there silently. As if mulling over what she was going to do about everything Donald just told her.

Finally, she picked up the phone at her desk, tapped a few buttons, and waited.

“Yes, can I get two authorities sent to my office please?” She placed the phone down and sat back in her chair smiling.

Donald was a bit confused by her expression, after everything he had been through, she was…smiling? “Is something…funny, Dean Pritchett?” he asked.

“Do you really think I don’t know what goes on at my school?” she asked, “Do you really think something like this could fly under my radar?”

Donald gulped, not sure what to say, so she pressed on for him, turning her computer screen around so he could see.

The whole screen was filled with footage of the Theta Iota Theta Sorority house. There was a live feed of one of the contestants with a #15 on his bib, furiously rubbing the front of his wet, messy, diaper with one hand, the other hand’s thumb in his mouth while he babbled “I love my pissy poopy Pampers! I love my pissy poopy Pampers!”. Another screen had a chatroom with dollar signs flying everywhere.

2k says he cums in under 2 minutes!!

You’re on!

10k on him to lose the whole thing!

Na, I bet 15k that #7 wants to stay there forever! He’ll keep losing purposefully!

The chats and bids were going by so fast that Donald couldn’t keep track of it all.

“Do you have any idea how much money this little ‘Sissy Games’ competition brings in?” the Dean asked, “How many people are actually behind this? How many are bought and paid for?”

Donald didn’t know what to say, he was flustered, panicking, “You…you can’t do this! I’ll…I’ll go to the police!”

“They’re paid off.”

“Then I’ll go higher! I’ll go to the FBI or the..the president if I have to!!”

Dean Pritchett just smiled again. “No…I don’t think you will…”

She clicked to a new window on her computer and clicked play. “You have a troubled past, don’t you?”

Donald couldn’t believe what he was looking at. It was the video of last year’s prom party. A girl was passed out on the bed face down. Donald watched his younger self come into the frame, taking a huge swig of whiskey with his dick already out. The other guys in the room of the video chuckling to themselves.

Donald was flummoxed, “You…you can’t prove that’s me!”

The Dean crooked her head to the side, right as his voice cut in “Hi, I’m Donald Triver, and I’m about to pound that ass!” Like he was about to do some Jackass stunt.

The Dean clicked the video off.

“I think I can trust you to keep your mouth shut.” She said.

Donald whirled and made to leave. As if running was going to get him away from all this. When he opened the door of the office, two very large men were standing there with their arms crossed.

“Ahhh, gentlemen,” the Dean smiled, “Thank you for coming! Please, take Mr. Triver away to where he can be more…useful to society.”

Donald cried and struggled as the two men grabbed him, carrying him off to parts unknown.

To be continued...