The Nerd Conquest

Author's Note: This is an edited version of a story I wrote and posted on Literotica in 2016.

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Chapter One

Mark was almost surprised at how happy the couple seemed. As he sat at his lunch table, he watched the guy and girl laughing and holding hands across their table. Other than watching them at lunch every day, Mark didn't know the pair. Just the previous Friday, they could hardly look at one another. Now they acted as if they were the only people in the cafeteria.

"Maybe I'm too much of a cynic," Mark thought to himself. Either way, he was glad the couple had worked things out.

Forgoing his contact lenses, Mark had spent the previous couple days wearing glasses and a baseball cap. After everything that had happened to him on Monday night, he longed for the anonymity. He also worried about the mystery girls from the movie theater. They could be in the dining room with him that very minute, sitting at the next table and joking about how they had mercilessly teased and tortured him.

The hat and glasses didn't provide much of a disguise, and Mark was well aware of this. For the time being, it was the best he could do. At least he had survived the entire day Tuesday without anyone asking him to strip naked or jerk himself off in public. By current standards, that had to be at least a minor victory. His privacy was to be short-lived, though. In just over six hours, he was to report to the sixth-floor study room and prepare for his evening with Monica.

Mark's time with Monica was to be the second of three nights he was to spend doing whatever his hosts told him to. Lucy, his ex-girlfriend, had referred to his subjugation as 'nights of service.' It was all part of an arrangement the former couple had made after Janice, Lucy's roommate, caught Mark spying on Lucy in the shower. Mark had spent Monday evening entertaining Emily, and he would finish his week on Friday with Alison. For now, he had to prepare himself for Monica, his former high-school classmate.

Ironically, most guys would have killed for an evening with Monica. She was tall with a curvy yet toned body. Her jet black hair and big blue eyes were the perfect complements to her soft tanned skin. Her face was perfectly proportioned with striking features and nary a blemish. She was so much more than beautiful, though. She was smart, driven, and carried herself with unmatched confidence. Only the boldest of men would dare proposition her. Less confident suitors wouldn't even bother.

As nervous as Mark was about his reunion with Monica, he was just as concerned about his own stepsister learning of his subservience. Mark's stepsister, Alicia was best friends with Monica's sister, Tina. Monica did promise Mark that she would never tell the two younger girls about his evenings of service. Even so, he wasn't sure he could trust Monica.

Hoping for a few extra minutes to review his notes, Mark had opted to head out of the cafeteria a little earlier than usual. Since he wouldn't have much study time after dinner, he intended to take advantage of any available time. However, just as he was about to get out of the cafeteria, he saw Brooke making her way to his table.

"Seen any good movies lately?" Brooke joked throwing her backpack on Mark's table and helping herself to a seat.

"Oh, hi." Opting against responding to her taunt, Mark continued gathering his belongings. "Sorry, but I was just leaving. I have to get to class." He started to get up from the table.

"Oh well," Brooke said. She leaned her chair back on two feet while holding onto the table's lip for balance. "You're going to want to sit down for a minute and hear me out. This is important."

"Important?" Mark stood behind his chair awaiting Brooke's explanation.

"Please," Brooke said motioning for Mark to sit back down. "I really am trying to help you."

Mark looked around the dining area as he considered Brooke's request. He still wasn't sure what the young blonde wanted from him and why she was even mixed up in his arrangement with Lucy and Janice to begin with. "I only have a minute," Mark said as he reclaimed his seat.

"Thanks for gracing me with your presence," Brooke responded waving her hands in the air sarcastically.

"I'm sorry," Mark relented. "It's just that I have to get going. You know what I'm dealing with this week, right? Well, I still have class work too."

"I do know what you're dealing with," Brooke answered sternly. "I also know you played a pretty big part in digging that hole."

"I'm sorry," Mark conceded. "Really. Please, tell me what you needed."

Brooke paused momentarily before continuing with her planned debrief. "There's something you need to know," she said. She dropped her chair back to all four feet and leaned forward across the table.

"Something else?" Mark queried. He leaned back slightly retreating from Brooke's advance.

"Yeah," Brooke answered. "It's a pretty big deal too."

Mark settled in curiously.

Brooke continued. "Remember the other day when I told you Janice would get tired of you, that she would move on to someone else?"

"I do," Mark said. "That's good. Right?"

"I guess so," Brooke returned. "It's good in a way. At the same time, do you really trust her with all those videos?"

"I don't know," Mark answered curiously. He leaned into the table. "It's not like I have much choice. Do I?"

"What if you did have a choice? Would you take it?"

"Sure. I guess so."

Brooke looked around the table to make sure no one was listening to their conversation. She extended her torso across the table toward Mark and continued with her story. "This all started with my father," Brooke said.

"Your father? What does your dad have to do with this?"

"I'm trying to tell you," Brooke continued. She explained to Mark how she had first met Janice. Brooke reminded him that Janice used to belong to a sorority but had been kicked out. It had all started a few years back when Brooke's father, a former professor, had visited the sorority house to assist a couple of students with a homework assignment.

A group of the sisters, inclusive of Janice, had agreed on a wager as to whether one of the younger girls could get the professor naked. The girl whose challenge it was to strip their teacher succeeded without much difficulty, and her exploits, of course, were all caught on video.

At first, Janice had used the video to leverage better grades for herself and her sorority sisters. Then once the girls finished the professor's class, Janice continued using the video against Brooke's father. She didn't ask for large sums of money, at least not at first. She just used the professor for her own amusement having him perform stunts such as wearing a thong to class and taking more incriminating photos of himself.

Eventually, Brooke's father had transferred to another school, and Janice moved on to harass other boys. Janice was finally kicked out of the sorority for humiliating their president's boyfriend.

Mark was shocked. He leaned back in his chair and rubbed his hands furiously through his sandy hair. "So your father had to quit his job?"

"He did," Brooke said. "Then when Janice found out I was going to school here, she sought me out."

"You? What did she want with you?"

"She wanted me to help her find another guy," Brooke said. "Janice told me she was going to contact my father again unless she could find someone else she could 'teach a lesson to.'"

"Teach a lesson to?" Mark asked. "What does that even mean?"

"I don't know exactly," Brooke answered shaking her head. "I do know that she has a serious problem with men."

"But, I don't understand," Mark returned. "I never even met you before Janice caught me...you know."

"It wasn't supposed to be you," Brooke said. "The plan was to drill the hole in the wall and spread the word around one of the fraternities. When the frat boys showed up, Janice would record them spying on the shower."

Mark's jaw dropped open, and his eyes expanded. "How did she end up catching me, then?"

"Well, you beat the other boys to it," Brooke responded. "I never even had to tell anyone. You found the hole on your own."

Mark was flabbergasted. Somehow, he got caught up in Brooke's sting operation. "So what do we do?" he asked.

"That's why I'm here," Brooke said. "We need to get on Janice's computer and erase all of her pictures and videos. We need to get the videos of you, of my father, and of anyone else she's blackmailing."

"But how?" Mark asked. "She used her phone to take the video."

"You're the computer guy," Brooke reminded Mark. "Janice is in class now. I have the key to her room and her computer password. I was hoping you could help me."

"But if the files are on her phone..."

"They're on her computer," Brooke interrupted. "I was in her room the other day when she was organizing them. Trust me. They're all on her laptop."

"Wow," Mark replied. "So how did you get her key...her password?"

"I borrowed the key from the resident advisor's room and made a copy. I learned Janice's password by looking over her shoulder as she typed. It took a few times, but I figured it out. She uses some sort of web storage for her computer and her phone. The way she explained it, every time she takes a picture or video on her phone it automatically loads to her computer."

"When do we do this?" Mark asked. "When would we get access to her computer without her noticing?"

"Right now," Brooke insisted. "We have to go now. Janice is in class, and her computer's in her room. I checked before coming over here."

Mark didn't want to miss his next class. At the same time, he couldn't turn down a chance to get those videos. Maybe he wouldn't even have to go through with his evening with Monica. "Okay. Let's do it."

Brooke smiled widely at Mark before grabbing her bag and leading him out of the dining room. The two ran full speed back to the dorm in hopes of finding the evidence Janice was using against Mark.

As the duo darted through the lobby, Brooke nodded at another girl sitting by the front door. "She's our lookout," Brook said as she continued to move Mark toward the elevators.

Since the elevators were once again out of order, Mark and Brooke had to walk up the six flights of stairs. All the way, Mark thought through their plan in his head. He wanted to make sure he didn't leave any evidence on Janice's computer or anywhere else. This could end up being the most important computer assignment of his life.

Mark's heart raced as Brooke unlocked the door to Janice and Lucy's room. Mark felt guilty breaking into his ex-girlfriend's living area; at the same time, he wasn't going to forgo such an opportunity. Lucy would do the same thing if she were in his position. Mark was sure of it.

As promised, Brooke had Janice's computer password and was able to log right in. "Here you go," Brooke said motioning for him to sit down in front of the device. "We don't have a lot of time."

Mark started poring through Janice's files. It didn't take him long to realize that she was using cloud storage for both her computer and her phone. They would be able to access the storage, but they would need another password to do so.

Mark tried entering the same password as Janice used for her computer, but it didn't work. He keyed in a couple more variations of the same password but didn't want to risk locking the drive and notifying Janice.

"What do we do now?" Brooke asked as Mark pushed back from the laptop computer. "How do we get the files?"

"We can't," Mark insisted. "Not now at least."

Brooke threw her backpack across the room and sat down on Lucy's bed. "I can't believe this," she added. "This is such bullshit."

Mark continued to plug away on Janice's laptop. He looked for some sort of password file or application but couldn't find anything. It made sense that Janice had everything password protected. Not only did she need those files as leverage over her blackmail victims; they could also incriminate her. Blackmail is a serious crime.

"I have an idea," Mark said. He pulled the computer back to himself and started tapping at the keyboard. "I know what to do."

Brooke ran to Janice's desk and hovered over Mark. "What is it?"

Mark explained that he would download a keystroke program onto Janice's computer. It would maintain a log of every key she pressed. Whenever she typed in her password, the program would save it. They would have a record of essentially everything Janice did on her computer.

"Perfect," Brooke said giving Mark a friendly kiss on the cheek and a big hug.

"It'll take some time," Mark explained. "We would need to wait until she uses the computer and logs on her cloud drive."

In addition to the keystroke program, Mark set up a remote access application. Assuming the computer was on, Mark would be able to log into it from anywhere.

Just as Mark was closing down Janice's laptop, Brooke's phone buzzed.

"We gotta go," Brooke said looking at her text message. "Janice is on her way up here."

Mark left Brooke on the sixth floor and headed down the back stairwell. He figured it wasn't a good idea for anyone to see him hanging around with Brooke, at least not until he had the incriminating files.

As Mark rushed down the familiar stairwell, it hit him. He would still have to spend his evening doing Monica, his former high school classmate's, bidding,. Since Mark didn't have the incriminating files yet, he couldn't risk tipping Janice off. If Janice found out he was snooping around her computer, she would almost certainly use the videos against him. If that happened, Mark would be fucked.

Chapter Two

Mark had an early dinner and left the cafeteria about 6:15 that night; he didn't want to risk walking back to the dorm with Lucy, Brooke, and Janice. It was going to be a long enough night on its own without having to deal with their inconsiderate jokes and one-liners. He also wanted a few minutes to collect himself before heading to Monica's dorm room.

Mark was more nervous about his time with Monica than he had been with Emily two nights prior. As humiliating as Emily's demands had been, she didn't know him before college and would likely never see him again. Since Monica's younger sister, Tina, had been so close to Mark's own stepsister, he had a prior connection to Monica. Moreover, if Tina ever found out about what he was doing, his life as he knew it, would be over.

The sixth-floor study room's lights were off when Mark opened the door. He paused before flipping the switch. The darkness felt peaceful even if fleeting. Despite his early arrival, Monica had already set everything up for him; his punishment was ready.

Mark scanned the room and saw a neatly wrapped box on one of the tables. His stomach dropped, and his head spun as he inspected the package. The fact that Monica had gift-wrapped the box showed how committed she was to ensuring his evening was as indelibly humiliating as possible. This was in sharp contrast to Monday night when Brooke had arrived at the last minute with his skirt and cropped top.

Mark knew the gift was for him as it was wrapped beautifully with blue foil and a massive yellow bow. His and Monica's high school colors were royal blue and gold. This was Monica's way of reminding him that they went way back and that she still had ties to his hometown.

As if the gift might somehow deliver a violent electric shock, Mark stepped toward the box and carefully nudged it. Upon completing his initial inspection, Mark snatched the ribbon and paper from the box with a quick tear. He set the white cardboard container down and slowly opened it. The contents were both meaningful and curious.

In the box, Mark found a bluebird mask, a blue thong, a set of blue costume wings, and a pair of yellow and blue tennis shoes. In addition to wrapping Mark's costume in their school colors, Monica was making Mark dress up as a twisted version of their school mascot.

Mark inspected the bird mask. It was more like a ski mask with bird eyes and a beak than a professional mascot head. He tried the concealment on. It fit snugly, and was very uncomfortable yet did not obscure his vision or limit his ability to breathe. He did like the idea of having his face covered up, especially if he was expected to wear the rest of Monica's costume.

Mark pulled the mask up his forehead so he could inspect the costume wings. He had no idea how he would even put them on until he saw a diagram clipped to one of the straps. The wings were basically triangle shaped pouches covered in fake feathers. To put one on, he had to crook his arm and slide his elbow in first. There was a grip at the edge of the material where his hand would press firmly against his shoulder and upper chest.

"Well whadda we have here," Lucy said as she stepped into the study room with Janice and Brooke. "Oh, my God. Monica really outdid herself on this one. Didn't she?"

"This is ridiculous," Mark insisted. "I can't wear this."

"Oh, but you will wear it," Janice chimed in jovially. "This is going to be fucking awesome."

Brooke approached Mark and gently gripped his bicep. "You can do this, Mark," she promised. Brooke casually shot him a wink and a nod. "After this, you'll only have one more punishment left."

"Well, you better get ready, birdy boy," Janice said sitting down in preparation for Mark's quick change.

Once Lucy and Brooke positioned themselves in the chairs surrounding Janice, Mark found himself once again disrobing for an audience. Consistent with previous experiences, Janice took the opportunity to record his wardrobe change on her phone.

Perhaps preoccupied with the strange outfit and worried about his evening with Monica, Mark didn't pay much mind to the three girls or to Janice's videography. At this point, it was as if they were the audience watching him in a dark auditorium, and he was an on-stage actor pacing through his lines.

Once completely naked, Mark slid into the blue thong. As far as he could tell, Monica picked out the smallest thong available. The pouch didn't completely cover his dick, and the waistband felt like it would snap at any second.

Mark put the shoes and bluebird mask on next. He was thankful to have his face covered even though the trio of girls knew exactly who he was. Mark then folded his arms in one at a time and slid them into the wing pouches. His limbs were now restricted to a flapping motion which was entirely appropriate for this particular bird costume and torture apparatus.

"You better move, birdy boy," Janice said. "You've only got five minutes. You don't wanna keep Monica waiting. Do you?"

"Just fly straight like the crow flies," contributed Lucy with a smile. She opened the door for Mark with an arm extended toward the foyer.

Mark crept through the foyer and into his least favorite hallway. A couple girls laughed hysterically as they saw his sexy bluebird costume. Not wanting to linger, he rushed past the girls and down the hall to Monica's room. He didn't even have to knock.

"There you are," Monica said opening the door for him. "That looks so fantastic on you. I was worried it wouldn't fit."

Monica was wearing a knitted knee-length purple dress with a black belt and black heels. She was dressed more for a night on the town than for a few hours in her dorm room. Considering his own outfit, Mark wanted no part of a night on the town. Mark quickly stepped into Monica's room; thankfully, she closed the door behind him.

Monica motioned for Mark to sit down on her bed. "Just hang there a minute, Mark. We'll get started soon enough."

"Started?" Mark asked. "What are we...?"

Before Mark could finish the question, Monica left the room.

Mark sat alone for almost thirty minutes. While he was grateful for the quiet, he desperately wanted to know what Monica had in store for him and where she had gone to. For all the waiting Mark had to do over the past week, he was no better at it. Not knowing what to expect was almost more than he could bear.