Brady's Hell Week - Day 02-03

Story Info
Brady's torture continues.
3.1k words
3.9
19.2k
11
2

Part 2 of the 2 part series

Updated 06/10/2023
Created 01/06/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Brady woke the next morning to the beautiful moment before the realization of your reality sets in. When you're still half in dream world. Unfortunately the moment was fleeting, and the harder Brady tried to chase it, the faster it disappeared. He laid in bed for longer than usual, considering whether or not he was even going to class. Once his internal debate finished, he figured Rob would just come find him anyway, so it was better not to let him see Brady sweat.

With labored movements, he turned to his left and set his feet on the ground. He let the blanket fall from his naked body, as he stood and made his way over to the small bureau across the room. When he opened it, he couldn't believe what he saw. Brady blinked a few times to make sure he wasn't dreaming, but he didn't wake up, and his drawers were still completely empty. He pulled each one out in succession, but none of them had any clothes.

Brady spun around, his heart beating in a panic. He didn't have long to think before a knock came at the door. After taking a moment to breathe, he grabbed the blanket and wrapped it around himself, before cracking the door open. On the other side was Rob, smiling wide.

"Hey there little guy! Ready for day 2?" Without asking, Rob shoved the door open and stepped inside. Brady quickly closed it behind him.

"Where are my clothes?" Brady said angrily, clutching his blanket.

"That was my idea! I figured today, I could decide what you wear... and I already have an outfit ready." That's when Rob held up a small t-shirt with the words "I have a tiny pee pee" written on the front in big letters.

"You have to be kidding."

"That's not all!" said Rob with glee in his voice. He then unfurled a tight looking pair of thin grey sweatpants.

"I'm not wearing that."

"Okay, but then I'll have to drag you to class naked, and I'm not sure you'll like that either."

Brady took a moment to weigh his options, before grabbing the clothes from Rob's hands, and sliding them on. When he looked down, he was horrified to see that the shirt barely came to his waistline, leaving his little package incredibly visible against the thin fabric of the pants.

"Fine. There. Happy?"

Rob smiled even wider "Yup. Now let's go. We got chemistry in ten."

Brady reluctantly slipped on his sandals, and followed Rob out into the hallway. The walk to class was hell. Brady tried not to pay attention, but all he could see was the faces turning to laugh at him as he walked by. Almost to class, Brady saw a group of women all huddled around a cell phone. Faintly he heard his own voice saying "I have a tiny pee pee" and instantly the group burst into raucous laughter.

Brady was thankful to get to sit in his desk, despite the side glances from a number of his classmates. Chemistry ended without incident, and Brady breathed a sigh of relief just getting to get away from Rob. The staring and laughing from everyone was still obvious and humiliating, but Brady tried his best not to let it bother him. About half way through the day, he saw Meghan, the woman who tortured him the night before, walking toward him with a smile on her face. Not one of vicious mischief, but one of apology.

"Hey Brady, I'm sorry about last night. It's just a stupid tradition. I didn't really have a choice. I hope there are no hard feelings."

Her words caught Brady by surprise. He took a few seconds to stammer before replying. "Oh, yeah. I get it. I just kind of gotta deal with it. It's cool. Once it's all done I'll be a freshman starting for HSU on national television. I'd say it's worth it."

"Good, I'm glad." she replied "And after a little bit, nobody will even remember what happened to you. That stuff happens all the time here. Soon some other guy will have videos of his humiliation playing in the student lounge."

"Seriously?..."

"Look, I felt bad and I saw you coming, so I grabbed you a coffee. I didn't know how you like it, so I left it alone."

For the first time in what felt like weeks, Brady smiled. "Oh. Thanks. I take it black, so that works."

"Alright, well, I hope to see you around." the gorgeous blonde woman winked at him, and like that she was gone, leaving him with his hot paper cup. He took a sip, noting an odd taste, but chalking it up to being cheap, cafeteria coffee, and made his way to his next class.

His good mood faded a bit, as he remembered that his next class was with Ms. Adams, a teacher with a reputation for cruel humiliation of any student that disrupted her class. He could only hope she didn't notice his shirt, as he sat in his desk, and crouched down as low as possible.

While waiting for class to begin, Brady heard his phone vibrate. He pulled it out to find a text message from Rob.

"Enjoy your coffee?"

Brady cocked his head to the side and typed out his reply.

"Yeah. How did you know about that?"

The reply didn't take long.

"Because I'm the one that mixed a crushed up viagra into it. Enjoy Ms. Adams' class! Lol"

Brady's eyes widened. Rob had to be bluffing. There's no way he would be that mean, Brady didn't have long to ponder it before Ms. Adams swept into the room, silencing the murmuring instantly. Brady quickly shoved his phone in his backpack, and lowered himself in his seat.

The first ten minutes of class went by fine. It was then that Brady felt the medication starting to do its job. Blood rushed to his tiny penis, and within thirty seconds he had a raging, three inch hard on. Brady tried flexing his calf, and anything else he could think of, but all he could really do was hope nobody noticed. It was only a few more minutes before he heard the woman sitting next to him giggle. He looked up to see her eyes locked on his tiny bulge. Unfortunately, Ms. Adams heard it too.

"Young lady, what exactly is so funny?" She said in a stern voice, as Brady's heart raced.

"I'm sorry." she replied "It's just that he has a boner." She said, pointing to Brady. Immediately everyone's attention turned to him, the laughter beginning to grow.

"Well!" exclaimed the severe looking teacher. "Young man, why don't you come up here and tell us all what has you so excited. I didn't think proper punctuation was so arousing."

Brady stalled for a moment, but knew it was inevitable. He stood up, and the laughter suddenly got a lot louder. Keeping his head down, he made his way to the front of the class. Turning to face them, he saw everyone staring directly at his tiny erection, some even discretely pulling out their phones to capture his humiliation. Ms. Adams surveyed his attire, taking a long time to look at his shirt.

"Well... little man. It seems like you're the kind of boy who likes attention."

"No I swear I..." He tried to come up with some explanation, but nothing would do.

"Alright. I'll give you one chance to tell us what I was just talking about, unless you were too busy... manipulating yourself to pay attention."

Brady frantically searched his mind for some shred of the class, but could remember nothing. "I... I'm sorry I don't remember."

"Well then..." Ms. Adams said with an angry smirk. "Since you seem to find attention more important than your education..." Slowly she made her way behind the young man, and yanked his sweatpants to the ground, allowing his little boner to pop free for the full classroom to see. He tried to cover himself, but Ms. Adams slapped his hands away. "No no. Hands at your sides. And you can stay up here for the rest of the class. I hope you enjoy all the attention."

With that she continued on with the class. Brady could only stand there, his medicinally induced erection refusing to abate even a little. The fact that he stayed hard the entire class seemed even funnier to everyone. Once she dismissed everyone, Brady pulled his pants up, and quickly rushed back to his dorm.

"We all know what he's rushing off to do!" said a voice behind him, followed by even more laughter. Brady just ran. He kept his head down until he got back to his room. He sat on his bed for a while, before ripping off the clothes Rob brought him. It wasn't long before he realized he had a small problem to deal with. He grabbed his rigid little cock with three fingers, and began stroking it furiously, more out of anger than excitement.

Once he finished, he cleaned himself off, and laid in his bed, dreading the next day. After a few hours he drifted off to sleep, not caring about missing class or not getting homework done. Only able to imagine the humiliation tomorrow would bring.

__________

Brady opened his eyes the next morning, and at first his body refused to move. The specter of the coming day was too much to bear. Eventually he had no choice but to stand up and make his way over to the dresser. He closed his eyes, took a deep breath, and pulled his drawer open to find... shirts. With a smile he opened the drawer beneath it to find Rob had also returned all of his pants. No sooner had the weight lifted off his chest than Brady opened his underwear drawer to find it still empty. He felt around inside, and found a small slip of paper with the words "They're hanging from your webcam" scrawled across it. Brady looked over in horror to find a pair of pink panties with tiny flowers all over them.

Brady considered just not wearing them, but he knew if Rob caught him, things would only get worse. He slid the panties over his legs, only to blush when he found that his below average package fit perfectly inside them. Shaking off the thought, he finished dressing himself, and headed off to class. His first class went fairly easily. Rob barely even looked at him. It wasn't until he found himself passing through the door to Ms. Adams' room that he hit trouble. The curvy, but severe looking teacher was leaning against the side of her desk, staring daggers at him.

"Welcome to class Mr. Wheelock. Don't head to your desk just yet. Stay up here." She ordered. He obeyed, keeping his head down, as his classmates filtered in. Once everyone was situated, she addressed them. "Alright class. I have spoken to the dean, and in order to avoid anymore distracting incidents like yesterday, Mr. Wheelock will be undergoing... arousal checks before every class."

The room could barely contain the laughter, which ended abruptly when Ms. Adam's put her hand up. "Unfortunately I can't do it, so one of you will have to."

Brady's jaw dropped. "No, you gotta be kidding. Can't you see I'm not hard?!"

"Frankly, as small as you are, I wouldn't be surprised if jeans hid it completely. Now... Sarah, why don't you be the unlucky one today?"

Brady watched helplessly as the girl who had called him out the day before stood up, and made her way over to him. Drawing it out, she grabbed his waistband and slowly pulled it back, letting out a loud giggle when she looked down.

"Yeah, he's as tiny as ever... interesting choice of underwear though." That's when Sarah let go of his jeans, but pulled up on the waistband of the panties, letting everyone get a good look, as he struggled to stuff them back in.

"Alright!" Ms. Adams voice cut through the noise. "Go sit down. And I honestly applaud Mr. Wheelock for his practicality. With a tiny member such as his, he doesn't need the room that men's underwear provides. Panties are likely a much better fit for him. Good for you."

Brady tried to explain, but she was off and running with the lesson. He hid his reddening face the best he could, barely making it through class. The rest of the day was uneventful, and Brady breathed a sigh of relief when his last class finished. It was a gorgeous day on the quad, and he took a moment to stop and breathe in the fresh air, while the groups of people around him chattered excitedly about plans for homecoming weekend. Brady's spirits sunk when he felt a heavy hand clap him on the shoulder, and looked to his right to see Rob smiling at him.

"Hey there Tiny! How's the day been?"

"Fucking awful." Brady replied. "Can you just leave me alone today?"

"Oooh, sorry little guy, no can do. It's hell week, not minor inconvenience week. LADIES AND GENTLEMEN!" Rob bellowed. Brady tried to beg for mercy, but was cut off when another member of the football team grabbed his hands and pulled them behind his back, securing them in a pair of handcuffs with a horrifying click.

"By now most of you are familiar with Brady here... or at least one small part of him." This brought laughter, as the crowd grew. Brady tried and failed to swallow the panic, while the second team mate held him in place. "We want you to learn more about HSU's newest star freshman! Things like... does he wear boxers or briefs?"

`With that, Brady felt hands grab his pants from behind, and yank them to the ground, revealing his flowery panties to the laughing crowd.

"Well that's certainly a shocking choice!" Rob laughed, as Brady squirmed helplessly. They let him sit there for a while soaking up the stares and laughter, before grabbing the back of his panties, and yanking them up his ass, lifting him into the air with a painful wedgie. Meanwhile the fabric stretched tight against his package, letting everyone see a clear outline of his tiny cock.

Brady tried to wiggle free to no avail. Rob and his cohort carried Brady over to a nearby flagpole, hooking the back of his underwear onto the rope, and hoisting him up even higher for everyone to see. The crowd cheered, and took pictures, as Brady could only dangle.

"Please! Let me down!" He shouted.

"I don't think so! I think everyone is enjoying the show." Rob replied. "Don't crowd, everyone will have plenty of time to get all the pictures you want!" True to his word, Rob left Brady hanging as people came and went, getting plenty of images and video of his humiliation.

"Rob please, what do I have to do?" Brady begged.

"Well I don't think I can let you down until you give the crowd your big new catchphrase! It's what everyone wants!"

The crowd cheered in affirmation. Brady knew exactly what they wanted, but blushed heavily at the thought of giving it to them. In the end, there was really no choice.

"Fine! I have a tiny pee pee." Brady said, quietly.

"What was that? We couldn't hear you." came the reply.

"I HAVE A TINY PEE PEE!" He shouted, much to the joy of the onlookers. Slowly, Rob lowered him to the ground, stopping just as Brady's toes hit concrete.

"Alright everyone! You all get one good smack before heading off... for good luck."

Brady knew better than to argue, letting each passing person spank his exposed ass cheeks. By the end his backside was bright red, but Rob let him down, unhooking his panties from the pole.

"Alright Rob." said Brady "Can you please uncuff me and give me back my pants?"

"No can do and no can do! I'll tell you what I will do though..." Rob reached down and pulled Brady's dorm room key from his pocket, and pulling back the front of his panties. Rob then slid the key ring around the tip of Brady's tiny cock. He dropped the handcuff key down there as well. "You can run along home and see if you can get anyone to help you." With a laugh, Rob turned and left, not even giving Brady time to protest.

He walked back as quickly as he could, trying his best to ignore the groups of people pointing and laughing at the guy with the pink panties and the tiny bulge. Once he got back to his building, he was faced with an entirely new task. He asked a few people passing by to help him, but all anyone did was laugh. He was eventually forced to go into the building and start knocking on doors. To his dismay, the only door that opened had a woman behind it. A short, red headed woman with large breasts and an adorably crooked smile. She got one look at Brady's predicament and busted out laughing.

"Yes." said Brady, tired "I know this is really funny, but I need your help. I need you to grab my key, and help me into my dorm."

"Okay" she gasped through the laughter "I'm... I'm sorry. Where is the key?"

"Ummm..." Brady motioned downward with his head, causing her to laugh some more.

"Oh god. Oh no, seriously? You're such a weird little perv!"

"You think I would do this to myself? Please, I don't like this any more than you do, but I need help."

Eventually her merciful side took over, and she pulled back his waistband, but her laughter was renewed when she looked down and saw his tiny dick. She recovered quickly, and reached down, sliding the key off of the head, stealing one more little glance, before grabbing the handcuff key as well, and walking him to his dorm. She unlocked the door and opened it for him, before unlocking his hands.

"Th-thank you." he stammered sheepishly, before the woman gave his ass a quick slap.

"Don't mention it, baby dick." she giggled, before heading back to her own room.

Brady sat on his bed for a while, considering dropping out. After a bit, a more rational idea came to mind. He had a game on Friday, so he had to stay until then, but he could have a friend pick him up immediately afterwards, and not have to worry about anymore hell week shenanigans. He thought he was a genius... He thought.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
2 Comments
darthnader19darthnader19almost 3 years ago

Def needs another chapter

AnonymousAnonymousover 3 years ago
I hope Brady is taking notes

When Hell Week is over he should be making plans on revenge on all people that humiliated him. Hanging by his panties on the flagpole was dangerous to say the least. I was surprised that he did not fall over since he was certainly top heavy and tall anyway; plus having his dick and balls being pulled up and tight would have cause a lot more pain. There is a lot of good, albeit short, creative writing in this imaginative story. He still has four more days to go so there is a lot of more degradation that happen.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Dr. Berlin Dr. Berlin helps Kelly cuck her boyfriend.in Fetish
Cassie and Eric Ch. 01 Cassie and Eric are a strong couple that discover fantasies.in Fetish
Blackmailed Couple Used Married cpl are set up and blackmailed by a kinky bull.in NonConsent/Reluctance
Brady's Hell Week - The Grand Finale Brady's awful week comes to an end.in Exhibitionist & Voyeur
Mr. Johnson's Wild Ride A new teacher gets more than he signed up for.in Fetish
More Stories