Daily Free-Write March 24, 2021: An Easy Bet Pt. 2 (Patreon)

Continuation of March 19, 2021: “An Easy Bet”

"Don't make me cream my diapers, dude!" A gawky guy with glasses was pleading as a bigger man held him in his lap and rubbed the man's diaper bulge.

"Do my homework and I'll think about it, baby."

Of course the guy agreed, and quickly finished the man's calculus homework, only to be brought back to the couch and rubbed to climax anyway while the other frat brothers and their friends watched and laughed.

This was Dexter's life now. Dexter had spent weeks stuck in diapers and forced to cum in them as the frat's house baby. Every day he was sure he would make it to midnight without cumming, and finally get out of them. Every day, the frat members found a way to make him spurt into his crinkly padding. And the worst part was, he was beginnning to like it.

As he went to sleep that night in his crib, watching the mobile above his head turn around and tinkle a soft lullaby tune, he thought again, for the thousandth time, about how he ended up in this situation.

It all started the first week of classes, when Dexter and his friend Eugene went out to check out the student club fair.

"Computer club! Cool!" said Eugene, eyeing a table several people in glasses typing away at laptops.

They looked at various tables and talked to a few people, purposely avoiding some of the more sporty tables which tended to have the people that looked like the people who made their high school lives miserable.

"Have you seen the booth for math club?" asked Dexter, looking around at all the tables. Various cultural clubs and social clubs and hobby clubs were set up, but so far no math club.

"I don't know, but lets check out that club over there," said Eugene. It was MENSA; the 'smartie pants deluxe' club. They were actively signing up members and it looked like they had a very challenging puzzle for people to join. They made a beeline for that club but were halted by a guy in a school jersey and shorts with a backward baseball cap on. He looked like a junior football coach, and he was wide enough to stop both of them in their tracks.

"Hey, there fellas! You look like just the kinda guys we could use in our Greek letter organization!"

"A fraternity? Uh… no thanks," said Dexter, laughing nervously. "It's all greek to me, haha."

"Come on, man, I saw you two checking out the other tables. Leave the geek life and join the Greek life. What's your name?"

Dexter, who had a hard time getting off the phone with a telemarketer could only reply to the man's commanding voice with a meek, "Dexter."

"And you?" the man asked, turning his attention to Eugene.

"Er… ah… Eugene?" he asked, as if he was asking permission.

"You can call me Alpha," said the man who shook Dexter's hand with a firm grip. "You two should sign up! Whaddya say?"

Eugene looked skeptical. "Isn't this like, you know, a jock thing? What would you want with a couple of math and computer geeks like us?"

Alpha shrugged. "We're trying to add more diversity, is all. Yeah sports are cool and all but meatheads are a dime a dozen for us. I think you two could be really good to have around."

"Really? Level with us, man. Why are you wasting our time with this?" Dexter looked at Eugene. His buddy had some backbone after all. He was a little awed, but also scared of what the bigger man might do.

Alpha chuckled and scratched the back of his head. "All right, I'll level with you. I'm just here because no one else would do it. I'll be ready to close up shop here as soon as I've signed up enough people, but it's been slow as balls. I just need two more people to sign the list and promise to come to the frat house tonight, and you two would be the last ones on the list. Would you help a fella out? You don't even have to pledge if you don't want. Come on guys, I'm desperate here!"

"I don't know…," said Eugene, rubbing his chin. "You'd owe us pretty big if we did that…"

"Oh yeah," said Alpha, smiling. "Big time! I would make sure everyone knew you were protected. I can promise you that."

"Come on, man," said Dexter. "Have a heart. The guy's suffering! Besides, we coulda used some protection in high school. Maybe this'll be a good change!"

Alpha snickered a bit as Dexter said that.

"What's so funny?"

"Oh, nothing, nothing. Just a joke I heard. I'll tell you later. So you're signing, right? And we'll see you tonight?"

They did sign, and then Alpha made them promise to show up, or he'd be screwed.

"You have to come or it doesn't count. I promised you protection, so don't fuck me on this, or I won't be happy."

The two guys gulped.

"Are you sure this was a good idea?" asked Eugene, as they walked over to the MENSA table.

"That was scary, right? Imagine how people will feel if they try to mess with us and he shows up!"

They both agreed, feeling better about their decision already. Besides, they didn't have to join. Alpha said so. All they had to do was show up.

Later that evening, the two of them walked into the house where the rest of the pledges were waiting. Alpha greeted them enthusiastically when they came in.

"Wow, you made it! I was beginning to think you weren't coming. Thanks again guys."

"Yeah, hehe," laughed Dexter, nervously. "N-no problem."

After a short speech by one of the senior members, which the two boys practically snoozed through, they were on to the assignments. Each aspiring member drew a task that they had to complete in order to join. They ranged from the very easy - such as completing every member's math homework by the end of the night, to nearly impossible, such as going out and getting 5 guys or girls' numbers in five hours. Some accepted, while some turned them down. Dexter suspected that he and Eugene weren't the only misfits that signed up, as he saw the pattern of who agreed with confidence and who slunk away.

Finally, it was Dexter's turn.

"Okay pledge," said Alpha, "Ready to learn your challenge?"

Dexter gulped and nodded. He drew is piece of paper and Alpha took it, turned around and looked. He turned back around and grinned. "Oh, this is a fun one!"

He held the piece of paper up and showed it to everyone but Dexter. People began to chuckle and giggle.

"Feast your eyes…" The Jock reached into a small backpack on the floor with a flourish and pulled out…

"A diaper?" Dexter asked, cocking his head in confusion.

"Your new underwear." Alpha said with a grin. "At least until you beat this challenge. You're house baby now. There's always one. Think of it like tag. Once you pass, this one moves on to someone else and you won't have to be house baby again."

"We don't have to go through with this, remember?" asked Eugene, who was looking ready to bolt.

"Oh come on, it's not that hard," said Alpha. "All you have to do is go through one day as house baby without creaming your pampers and you'll be a full-fledged member with all the protection you could ever want. But until then, it's diapers all the way."

"W-well…" said Dexter, shifting uncomfortably and glancing toward the exit. "Thanks for the offer but…"

"What's a matter? I gave you an easy one. It shouldn't be that hard to keep from creaming your pampers… unless…" Alpha looked at Dexter and rubbed his chin with suspicion. "Unless you're into that sort of thing…"

"N-no!" said Dexter Blushing. "I'm not into that at all!"

"I don't know, man. You don't seem so sure, does anybody else?"

He looked around the room. Pledges and members alike shook their head and several snickered. Dexter got a sinking feeling in his stomach.

"Uh oh, Dexter. You don't want the reputation of being the campus diaper boy, do you?"

"B-but I'm not," whined Dexter, looking around the room at all the unsympathetic faces.

"Why don't you prove it?" He held the diaper up to Dexter, who stood stock still, looking like a deer caught in headlights. "Hey, man, calm down," said Alpha, his expression softening. "I didn't think it would be that big a deal... I'll tell you what, I'll make this challenge even easier. Wear til the end of the night without cumming and if you can do that, you can be a member… Don't tell me you can't do that."

"N-no. I mean I can! That's easy." said Dexter, crossing his arms and looking annoyed.

"Alright, he accepts," said Alpha. "Go get the old house baby."

A man was led into the room. He was wearing a pink bunny outfit, and waddling with what was clearly a thick, saggy diaper. He was sucking a pacifier and hugging a cute teddy bear tightly, his face bright red as he was led of the center of the room.

"I'm outta here," said Eugene. "Have fun, Dexter." And with that he was gone.

"Gee thanks," said Dexter, who was suddenly flanked by two large and friendly looking guys who rested their hands on his shoulders. They did it in a jovial manner, nevertheless when he tried to back up, the hands were as unmoving as stones.

"Okay, buddy. You're out of diapers."

The guy immediately spat out the pacifier.

"Really?! You mean it?!" asked the man, who seemed overjoyed.

"Yup, no more protection for you."

A frat brother took a key and unlocked a little padlock at the back of the man's pajamas and unzipped him. Then they took off his diaper and let it fall to the ground along with the pajamas, leaving the man naked and dripping in the middle of the room.

"Here, put some clothes on, dude," said Alpha, who tossed the man a plain tank top and gym shorts.

"Thank you. Thank you!" he said putting them on and hurrying out of the room.

"W-was that a … uh… member?" asked Dexter.

"No, sadly he never made it through the challenge, so he's just out of the running now. I'm sure you'll do better, though."

Dexter had a sinking feeling as he was taped into the man's soggy diaper and zipped up in his bunny outfit. He cringed as the thick soggy material pressed against his crotch and butt, forcing his thighs apart and bulging obscenely out in the pink bunny outfit. Alpha smiled in approval.

"Well I think that's everyone. Good luck with all your tasks, pledges. I'm gonna tuck the little one in for the night. It's his bedtime."

Let's show you your new room, baby bunny." Alpha said, grinning down at Dexter, who struggled and failed to break the man's grip. He was tugged upstairs to a giant nursery that would be his new bedroom until he beat the challenge. It wouldn't be hard though, all he had to do is make it through the night, right?"

-Written by ChampTehOtter