Frat Pledge

Botched Pantie Raid

Chapter 1 by Nicegent42 Nicegent42

The sun was just beginning to set as Timothy Thompson stood in front of the Omega Omega Kappa fraternity house. The large, imposing structure stood proudly amidst the sprawling campus, a symbol of brotherhood and tradition. Tim's heart pounded with a mix of excitement and nervousness as he stepped closer, feeling as if he was taking his first steps for a better future. The house itself was large, but not truly imposing, but all of Tim’s life he had been the small fish in the pond, no matter the size of the body of water. He wasn’t the tallest at five foot seven, but that didn’t make him that short, the problem was he just never stood out. Scrawny and born with asthma he was never great or even good at sports, with no real chance of even being as capable as others his interests delivered from feats of athleticism. So he couldn’t bond over basketball or football like some of his peers. When that happens kids tend to move more towards being classified as a nerd, Tim on the other hand never did better than okay academically. He tried to do well, studied, but knowledge for knowledge's sake never motivated him. Leaving him squarely in a more undefined category for as groups went growing up and leaving him with few friends.

The house was bustling with activity. Music pulsed from the open windows, and the scent of grilling meat wafted through the air. Tim could hear laughter, a symphony of fraternity life. He took a moment to compose himself, adjusting his shirt and smoothing his long blonde hair before walking up the steps to the front door.

Tim would have just knocked, but a red posterboard was taped to the door with a message written on it in black marker.

Pledge Week, if you want to join ΩΩK just come inside, all are welcome!

Nodding to himself, feeling a bit nervous he entered the house, Tim was greeted by a mix of curious glances and friendly smiles. The fraternity members were a diverse group, ranging from tall and muscular to lanky and intellectual. They were all dressed in casual clothes, some wearing fraternity-themed t-shirts or hats. Tim felt a sense of belonging there, something he desired among them and couldn’t help feeling nervous butterflies in his stomach, even as he smiled brightly.

"Hey, you must be the new pledge," a tall, lanky guy with a friendly smile said, extending his hand. "I'm Jake. Welcome to Omega Omega Kappa, we like to think we are ookay." He said drawing out the first letter of the word in a playful way to mirror the first initials of the fraternities name.

"Thanks, Jake," Tim replied, eagerly shaking the older boy’s hand, clasping it between both of his and doing so for just slightly too long. "I'm Tim. Well, Timothy Thompson and I wanted to pledge, I mean I wanted to pledge here. I’m a computer science major and I’m from…"

"Nice to meet you, Tim.” Jake said, pulling his arm away as he spoke over the excited freshman. I’m actually the vice president of the chapter, full names Jake McGraff… I wouldn’t introduce yourself with your full names its… its odd, man.” Jake said feeling like he needed to reciprocate the freshman by giving his own full name. “I can tell you're eager, what makes you want to join?"

Unintentionally Tim found himself nodding, subconsciously agreeing that he did in fact want to join. “My father actually was a member… back when he was in college, but not on this campus and that is where he met my mother. So I’m a legacy or whatever you call it, that means I can join right?”

They passed through the living room, where a group of fraternity members were playing a lively game of poker. The room was filled with the sound of laughter and the clinking of chips. Tim couldn't help but smile at the camaraderie and energy in the air. Jake taking in the young man that he couldn’t help think of as a kid despite only being a few years younger. “Yeah, well, maybe. It helps, but really its about you and how you fit in with us, right?”

“Supose so.” Tim’s face faltered slightly, before his happy smile returned. “I’m sure I will fit and will do whatever it takes to prove myself.”

“Good, yeah.” Jake nodded, really wanting the kid to dial down the kid from eleven, more to a five with how chipper and eager he seemed.

Next, the pair entered the kitchen, where the scent of grilling meat was even stronger. A few fraternity members were manning the grill, flipping burgers and hot dogs. Jake introduced Tim to them, and they welcomed him with friendly nods and smiles.

"Alright, Tim, let's head upstairs," Jake said, leading him to the second floor. "This is where the pledges sleep. You'll be sharing a room with a few others. It won't be that great and more than a little cramped." Jake motioned to the room that was little more than a pair of bunk beds and a single tall dresser.

Tim had followed Jake up the stairs, his heart still pounding with excitement. The room could have been spacious if it was a single bedroom, but with the double set of bunk beds lined up against the walls most of the real estate was taken.

"Thing is…." Jake started to say, his words dragging out as he was not able to shake an odd feeling about the freshman, his overly happy attitude rubbing on him like sandpaper. “This room is really only for the pledges that have been accepted. So you will have to make other arrangements.”

Looking at the room Tim could imagine getting close to others his age, bonding with his future fraternity brothers, jointly commiserating the cramped quarters. It didn’t sound that bad to him at all, but the news he wouldn’t be able to stay in the room did add a bit of a wrinkle. “Oh… I thought… being a legacy and all. Oh… okay, maybe I can still get a spot in the dorm rooms.” he said thinking back to his father telling him how this would be a sure thing and to not worry about it and now finding out he did actually need a place to stay. ‘Things probably just changed since Dad went here, just have to get through hell week and then I can stay here.’

Jake blinked slowly, chewing on his own bottom lip. ‘What kind of idiot shows up at college without a place to stay?’ Letting out a sigh Jake gave him, he was just trying to give the kid a reason to not pledge, but now he just felt like he had kicked a puppy. “You know what, don’t worry about it, you can just sleep on that bottom bunk over there.”

"Thanks, Jake," Tim replied, setting his bag down on the bed. "I appreciate it!"

With a shake of his head Jake left the kid to get himself settled, thinking about what he was going to do to him and the other pledges to have a little fun.

Tim took a moment to look around, not just in the room but at people about the house. The others were chatting and laughing, already forming bonds with one another. It gave him a sense of belonging, despite the nervousness that ran through his body and mind. Quickly unpacked his bag, hanging his clothes in the small closet and placing his toiletries in the shared hallway bathroom.

As he finished settling in, Tim heard a commotion downstairs. He peered over the railing to see Jake, standing in the living room, wishing he was nearly as tall as the older boy. Jake was tall with messy brown hair and warm eyes and a confidence to him that Tim envied and the others around seemed to be hanging off his every word.

"Alright, listen up, everyone," Jake said, his voice booming through the house. "We have a new pledge joining us today. Timothy Thompson, get your butt in gear and come down here." his voice turning into a below as he mentioned the newest pledges name.

Tim took a deep breath and made his way downstairs, his heart pounding in his chest. His feet moved as fast as they could down the stairs so that he could stand beside Jake to meet his future fraternity brothers.

"Timothy here is the son of one of our esteemed alumni," Jake said, clapping Tim on the back. "Let's give him a warm welcome to Omega Omega Kappa."

The fraternity members cheered and clapped, welcoming Tim with open arms. Tim couldn't help but smile, feeling a sense of pride and belonging. All the talk of needing to prove himself meant nothing to the idea of gaining so many friends.

"Now, Timothy, let me give you a little advice," Jake said, leaning in close. "Pledging is no easy task. You'll be cleaning, sleeping on the floor some nights, and wearing these ugly brown sweaters at all times."

Jake handed Tim a large sweater with the word Plede on the front. Tim chuckled, taking the sweater and putting it on over his shirt. "Thanks, Jake," Tim replied, his cheerful attitude unchanged. "Plede, huh?"

Jake pressed his lips together, hating the fact the sweaters they had ordered had the word pledge misspelled. "Printing mistake.” he lied, knowing it was his own fault when he put in the order. “We'll see about you earning your place here, but for now welcome to Omega Omega Kappa house."

As the day moved on and turned to night, Tim found himself immersed in the fraternity's rituals and traditions. He helped clean the house, sweeping floors and wiping down surfaces. Moving to being on his hands and knees with his own toothbrush to clean the grout between the tiles on the floor that became his place to sleep despite the bunk bed he had been shown on his tour. Using a thin blanket and pillow provided by the fraternity for a small bit of comfort, the word comfort being very much a lie. Despite the discomfort, Tim remained bright and cheery, determined to prove himself to the brothers.

Over the next few days Tim was busier than he had ever been before, making things pass by in a blur of activity. There were classes, but much of the time seemed to be filled with the various chores him and the other pledges had to perform, each of them wearing a similar sweater in various colors. Cleaning the grout with his toothbrush was one such chore that took up a great deal of his time, but another pledge had to do something similar with all the toilets in the house, making the young man feel like he got off easy despite how sore his knees and fingers were from the task, even as another trimmed the grass out front with a pair of scissors. They were also required to attend study sessions and participate in group activities, none of them allowed to remove the sweaters to make them stand apart.

Tim's cheerful attitude had not ceased to annoy Jake. Who saw Tim as a nerdy kid who didn't fit in with the fraternity. Legacy or not it felt more and more like his presence was a burden that he did not want to keep dealing with. It would be one thing if he was just excited, but it just didn’t seem to end and someone being bright a cheery first thing in the morning when all he wanted to do was sip coffee and wake up was not something he wanted to be near in the short or the long term.

One evening, as Tim was helping clean the kitchen, Jake approached him. "Pledge, I have a special mission for you," Jake said, leaning against the counter. "We need someone to go on a panty raid to the Tri-Sigma sorority house. Think you can handle it?"

Tim's eyes widened with excitement. "Absolutely, Jake! I'm ready for anything." He didn’t actually think a pantie raid was a real thing, at least not anymore, something from a bygone era that only existed in movies and tv shows.
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Jake smirked, knowing that Tim was unaware of his true intentions. "Great. All pledges have to do it at one point or another to be accepted. Now is your time, this is a make it or break it moment. Think you can do it?”

“Yes sir!” Tim saluted, feeling a bit like a fool for doing so. Between Tim’s eagerness and believing all the pledges had to do the task, he accepted the mission without further thought. He spent the next few hours preparing, gathering supplies and planning his approach. His mind was filled with determination and excitement, believing that this mission would prove his worth to the fraternity.

“Okay, this is the important part. You need to not get caught and if you are, I… we here at Omega Omega Kappa didn’t put you up to anything. This is your decision, you don’t HAVE to do this.” Jake said, stressing the part that there was no obligation even as he had told the kid everyone had to do the task less than a minute before.

“Got it. Don’t get caught and if I do plausible deniability.”

“Yeah… something like that.” Jake agreed, the same cheerfulness that made him want to get rid of the kid making him already feel guilty for setting him up.

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