Part 19: Little Bro Challenge
“Oh god, that was hell,” Josh said as he collapsed on his bed. Josh and Chris just got back from a grueling football practice. Their coach has been working the whole team really hard this week, trying to keep the team’s winning steak going.
“Yea, I feel dead...and disgusting” remarked Chris as he smelled his own sweaty armpits. “I’m going to take a shower.”
“I should do that too, once I get feeling back in my legs.”
Chris got his things had headed to the communal bathroom. Josh just laid in bed in his sweats and started to doze off.
**Beerrp Beerrp Ping, Beerrp Beerrp Ping** Josh’s phone started going off. He picked up his phone and saw it was Zach calling. “Oh crap,” he thought as he answered.
“Hello?”
“Jock Boy! Get your ass to the house now!”
“What? Why?”
“Don’t fucking ask questions. Get here in 10 minutes or I’ll make Butch punish you for cockblocking him at last week’s party.”
“Okay okay! I’m on my way!”
Josh hung up the phone, got his shoes on, and ran out of his dorm room toward the house. He made it with just a minute to spare with Zach waiting for him at the front door.
“Good job Jock Boy.”
Panting from his sprint, Josh asked, “what’s going on? Am I in trouble?”
“No, you’re not, but I need your help. Come with me.”
Josh followed Zach to one of the bedrooms where Tyler and his big bro, Danny, were talking. Tyler had a concerned look on his face.
“Alright, he’s here!” exclaimed Zach.
“Good, now we can figure this out,” said Danny.
Josh still had no clue what was going on. “Figure out what?”
Zach replied, “Oh, I told Danny here that you’re the star pledge of the entire pledge class, but he doesn’t believe me. He thinks Tyler knows his frat history better than you.”
“Oh geez, nah no one is better than anyone in our class. We’re all one. We’re in this together!” said Josh, trying to dismiss the issue.
“Screw that,” said Danny. “I don’t want to hear this ‘We’re all equal’ bullshit. Zach said you know everything and I’m challenging him on that.”
Zach gave an evil grin, “Yea, you’ve been studying really hard, haven’t you Jock Boy? You don’t want to let me down, do you?”
“Well no, but I don’t want to go up against Tyler.”
Zach patted Josh on the shoulder, “It’s just a friendly challenge. I want you to make me proud!”
“Wait, what if I lose?”
Danny chimed in, “If you lose, which you will of course, then I will give you and Zach a punishment. And vice versa.”
“Oh fuck, so Zach and I both be punished?” Josh hated the idea of the high stakes.
“If that worries you, then you can do Zach’s punishment for him hahaha.”
“Don’t worry that, we’re going to win anyways, right?” asked Zach.
Clearly realizing he wasn’t going to get out of this situation, Josh replied, “Yea, I’ll do my best.”
“Good! Now make me proud little bro! Let’s get this challenge going.”
Zach and Danny led the two pledges out of the bedroom and down to the living room.
Josh whispered to Tyler, “Um, how’s is this going to work?”
Tyler whispered back, “I have no idea, but I’m fucking scared man.”
Down in the living room, they saw some other brothers and pledges hanging around.
Zach shouted to get everyone’s attention, “Gentlemen! We have a history challenge going on!” Upon hearing that, the brothers got excited and started cheering. Josh and Tyler’s pledge brothers had no clue what was going on. Two brothers offered to volunteer to help.
Zach continued, “Jock Boy and Boner, go over there and stand in front of everyone,” motioning toward the fireplace. Josh and Tyler walked over and turned to face the brothers and pledges. “Okay, now, we’re going to ask a question, and you’ll whisper your answer to the brother at your side. He will then tell us what you answered. For each answer you get wrong, you’ll do something to you. The first one to get 10 wrong loses.”
Danny started the challenge, “Okay! First question, who are our founding fathers?”
Josh and Tyler each whispered their answer to the brother beside them. The brothers then went up to Zach and Danny and gave the responses.
“Good job pledges! You’re both right! Next one, what year was our fraternity founded?” Again, they gave their answers. “Both of you got it right. Let’s continue.” Josh and Tyler got the next 8 questions right, but they grew more concerned with each question. Clearly, the crowd in front of them was waiting for something to happen.
“Okay okay, question 11. What is Butch’s middle name?”
“What?” thought Josh. He had no idea. He looked over at Tyler who also had a confused look on his face.
“We need an answer pledges, now!” The two gave their answers to the brothers, who reported them to Zach and Danny.
“Tsk tsk, looks like you both got it wrong. Both of you, take off your shoes.” Josh and Tyler kicked off their shoes. It seemed that the punishments were just going to be stripping off clothes, which Josh didn’t think was so bad.
“Next question, which brother used to be a professional video gamer?” Again, Josh appeared clueless but guessed a brother at random.
“Alright Boner! You got it right!” said Danny. “Jock Boy, remove your socks.” Josh did as he was told.
The difficult questions continued. Both Josh and Tyler seemed to know some obscure facts, but they were both losing clothes at a fast pace. After 10 more questions, Josh ended up with five wrong and Tyler had gotten three wrong. Josh was down to his jockstrap and Tyler still had his tighty whities and shirt on. Josh realized there weren’t enough clothes for all the possible wrong answers, he then started getting even more scared.
After the next question, Josh lost his jockstrap leaving him completely naked and Tyler was down to his underwear. The brothers and pledges in the audience were completely enthralled with the game. Some were cheering for Josh, others for Tyler. Some just cheered whenever someone lost. It was really exciting for them, but utterly embarrassing for Josh and Tyler.
The next question was asked.
“Oh damn, both of you got that one wrong also,” said Danny. Tyler lost his underwear to reveal his semi hard cock and cock ring. Josh didn’t know what was going to happen to him. Suddenly, the brother who was taking his answers took his arms and attached wrist cuffs to them. Then he used rope that was attached to a ceiling hook and hooked his cuffs up to them. He was left standing with his arms fully extended upward and with just enough slack to get his feet firmly on the ground.
“Oh shit!” cried Josh. Tyler and the other pledges looked at Josh with large eyes, showing concern for their fellow pledge brother.
“Let’s keep going. It looks like Boner is winning at the moment!” said Danny. However, that lead didn’t last long as Tyler lost the next two questions and Josh got one wrong. Both of them were now strung up with their arms above them and spread bars were attached to their legs. They both felt very exposed and helpless.
The current score was seven wrong questions for Josh and six wrong for Tyler. (Remember: Josh wears both underwear and a jockstrap for his daily uniform).
The next question came up and again they both got it wrong. This time, they were both gagged with their own dirty socks, which were held in place by a short rope, and then they were blindfolded with their shirts.
“How the hell were they going to answer questions?” thought Josh.
Zach spoke up, “Jock Boy and Boner, since you two can’t talk anymore, we’re going to start giving you True and False questions. Give your answers by nodding your heads. Got it?”
Both of them nodded their heads. Josh wondered if it was planned to have him and Tyler get blindfolded and gagged at the same time.
The next question came up. This time the audience could see the answers they were giving. Josh and Tyler could hear everyone screaming at them trying to get them to choose the wrong answers, hoping that they get punished more.
Both of them got the question wrong again. The whole room got quiet and Josh and Tyler kept wriggling in their restraints trying to anticipate what was about to come.
“Smack!”
“MMmmppfff!” screamed Josh as the feel of the paddle hit his ass. Tyler had the same reaction. They were paddled ten times each and their asses turned a bright red.
The score was nine wrong for Josh and eight wrong for Tyler.
Zach came up to Josh and whispered in his ear, “Don’t let me down Jock Boy. If you get one more question wrong, we lose. Come on, you can do it.” Josh nodded his head.
Next question came up and Tyler missed it. Clothespins were attached to his nipples.
“Pledges, both of you have gotten nine wrong! It’s really close here,” said Danny. “Here is possibly the last question! True or False? Is your Pledgemaster’s underwear blue?”
“What the fuck? How would anyone know that.” thought Josh. He and Tyler both had a 50/50 chance of getting the answer right. Josh nodded his head yes while Tyler shook his head no. Their blindfolds were taken off, but they were left gagged.
Danny spoke, “Looks like you both answered differently so we definitely will have a loser here! Trent! Will you do the honors?”
The crowd started yelling and cheering, urging Trent, the pledgemaster, to get up and reveal the answer. Trent got up smiling and motioned with his arms to get everyone to quiet down. The audience grew quiet and Trent unbuttoned his jeans and put his thumbs to its sides. In a quick motion, he pushed his jeans down to reveal black and blue underwear.
“Awwww so close! Jock Boy loses! Good job Boner! You’ve made me proud!” shouted Danny.
The crowd cheered at the results. Josh and Tyler were freed from their restraints and got their clothes back on.
Josh felt terrible for losing. Zach came over to Josh and patted him on the back, “Oh man, it was close Little Bro. Don’t worry, I’m still proud of you. Let’s hope the punishment for us isn’t too bad.”
Danny walked over with a grin on his face, “Are you two ready for your punishment?”
****** Any suggestions for what happens next?
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