The Nerd Conquest Pt. 02

"What if someone does come in?" He thought to himself. He had never performed oral sex on someone before. Mark had certainly seen his share of porn, but he hadn't exactly been taking notes. He remembered Alison's warning. If the girl he was servicing wasn't happy with his efforts, she would pull the rope. This had to be the harshest of grading scales especially for someone providing oral sex for the first time.

Mark heard someone trying to get in the hotel room door. He instinctively turned his head despite his sleeping mask. If the person seeking entrance had a key card, it was likely failing her. Again and again, he heard the door handle shake. Each time he waited for the door to open and his visitor to step inside. It never opened. Eventually, he heard footsteps walking away from his room.

"Maybe someone had the wrong room," he whispered to himself. If that were the case, the person wouldn't be back. If the visitor did have the right room, it would just be a matter of minutes before she secured another key and opened the door. As much as he hoped for the former, it was likely the latter.

Mark's heart raced as he sat on his calves waiting for the door to open. Would this be his only guest? Would she be alone? Would she recognize him? Would it even be a female? As the door handle rattled once again, he knew his time alone had come to an end. He had to prepare himself; if his performance were found lacking, his ass would pay the price.

Mark listened as the girl stepped into the room and closed the door. As Alison said would be the case, the girl didn't address him in any way. He lifted his butt off his legs returning to the position Alison left him in earlier. He tried to keep his face pointing toward the bed as his mystery guest stepped into the restroom.

Mark listened as the girl turned the bathroom water on then off. He then heard the bathroom door open and footsteps approaching him.

Any softening of his dick from his time alone was almost immediately undone. Mark's cock felt as big as ever, and the rings once again prevented blood from escaping his appendage. He imagined the girl inspecting his cock strapped in leather and metal.

Even though he couldn't see his guest, Mark could sense much of what she was doing. She stood just a couple feet away from him as she stepped out of her high heels and kicked them across the floor. He heard a long gentle "zip" as the girl ran her zipper down the back of her dress, and he felt a brush of air as she pulled the dress up over her head and threw it on the floor by her shoes.

The bed springs compressed as the girl sat in front of Mark. He heard stretching nylon as she slid her pantyhose free of her hips then down her legs. Again, Mark felt a rush of air as the pantyhose flew through the hotel air to the pile forming beside the bed.

The springs decompressed as the girl stood back up. Her cool hair whipped against Mark's face momentarily as she leaned forward and pushed her panties down her legs. He again heard the bed as she sat back down in front of him.

Anticipating that the girl would make some form of contact, Mark waited attentively. He felt the hairs on his arms and legs standing up. He couldn't be sure, but he thought he could sense her knees bookending his body. She had to be sitting on the bed directly in front of him. Her naked body was mere inches from his yet he had no idea what to expect.

After a long few seconds, Mark felt the girl's hands brush through his hair before clasping onto each side of his head. Suddenly, the stranger jerked Mark downward pulling his face into her lap. As he descended toward the girl's midsection, he was able to smell her scent, faint and unfamiliar.

The girl's coarse, curly pubic hair was the first to make contact with Mark's face. He envisioned dark black hair but had no way of knowing for sure. His mouth was firmly planted in her already wet pussy.

Still nervous and keeping his tongue to himself, Mark started out with a few kisses; he figured he would take it slow at first. He rested his hands on the bed surrounding her thighs as he began pressing his face deeper and harder into the girl's lips. He felt the tip of his penis brushing against the bed frame. The coarse sheets rubbing up and down his tip only heightened his arousal. He wanted to devour the stranger.

Just as Mark was getting into his chore, he felt a gentle tug from the hook inside his asshole. He assumed the girl wanted him to move things along.

Mark grabbed the girl's thighs, one in each hand, and started licking her pussy, bottom to top. A sign of his inexperience, his motions were more of a child consuming a lollipop than of a seasoned lover pleasuring his partner. Again, he felt the hook plunge into his ass; the stranger exerted a little more force compared to her first pull.

Determined to improve his performance, Mark plunged his tongue deeper into the girl's pussy whipping against the inside of her lips and working its way to her bud. Channeling the girls from his porn videos, Mark jammed his right pointer finger into her vagina and massaged her clit with his free hand.

The woman's legs squeezed in on Mark's head as her body squirmed beneath him. Providing such excitement to the stranger was an amazing experience for him; his penis grew thicker as the sides of his stem rippled around the steel rings.

"Uhhhh," The girl moaned as Mark continued to pleasure her. "Ohhhh...Yeah...Ohhhh."

The girl's uninhibited response was new and exciting for Mark. Unlike his times with Lucy, where it was more about mechanics than anything else, he felt a physical connection of cause and effect. He never even considered how much pleasure a woman could experience from sex. The stranger's pleasure turned him on.

The girl grabbed Mark's hair and forced his face deeper and deeper between her legs. He could hardly breathe, but he wasn't about to slow down. He plunged his tongue in and out of the girl's lips while massaging her clit with one hand and penetrating her with the other. The woman squirmed and moaned as he directed all of his focus and all of his energy to the stranger's pussy.

"Ahhhh," the mystery woman screamed a final time before falling limp on the bed in front of him.

Mark pressed his face slowly back into the woman's lap just as he felt a gentle yet distinctive tug on his asshole. She wanted him to stop.

Mark retreated a foot or so dropping his butt back to his ankles. As he tried to wipe some of the goo from his face, he thought about the massive grin he must have been flashing his guest. Mark was excited, but, more so, he was proud of his accomplishment. He looked forward to trying this again with someone he knew, someone he cared about.

Mark listened as the girl dressed. He desperately wanted to pull the mask back for a quick peek. Was the girl young? What did she look like? Did she know him? These were questions he would never get answers to. He would have to be satisfied with a final kiss on the cheek before listening to the stranger walk away from him and out the door. An unexpected emptiness consumed him as the lock clicked shut and the room fell silent.

Once again, Mark was left alone with only the refrigerator's familiar hum. Knowingly violating Alison's instructions, he decided to remove his blindfold for a quick look around. He figured he would have plenty time to put it back on if he heard the door again.

Taking an even bigger risk, Mark decided he would make a quick run to the bathroom. To do so, He had to slide the ass hook free of his butthole and remove the collar from around his neck. Knowing his next guest could show up at any time, he had to move quickly. The risk was worth it. Getting that steel ball and hook out of his ass was an incredible, even if temporary, relief.

Mark waddled into the restroom and did his best to pee through the contraption on his penis. He also took a few seconds to wash his face and gargle some mouthwash. He figured his next guest, if there would be another guest, would appreciate the gesture.

As Mark jammed the hook back into his ass and returned the collar to his neck, he noticed the alarm clock by the bed. There was just over half an hour left before midnight. Even though he had no idea where the past ninety minutes had gone, Mark was thankful to be near the end of his journey.

Just as Mark took his designated position in front of the bed, he heard the door rattling again. He pulled his blindfold back on and prepared for what he hoped would be his final task of the night.

Mark listened to his second mystery guest move around the room. This girl was undressing in the bathroom rather than right next to him. He had no idea if the change in behavior was any indicator about what he should expect.

Mark sensed the girl stepping between him and the end of the bed. She was wearing a thick coat of flowery perfume, a strangely familiar scent that made his eyes water under his mask. He thought this was odd since Alison and her perfect friends would never go out with such an obnoxious odor. This all but negated the possibility that he was pleasuring someone from Alison's group. Even so, he couldn't shake the feeling that he should know who the girl was.

The bedsprings notified Mark that his guest was in place and ready for his performance. Instead of waiting for the perfume-soaked girl to summon him, he immediately leaned toward her. As he grabbed for the girl's legs, he was surprised to find her shins lifted into the air above the bed. She was lying face-down rather than on her back.

When Mark pulled back in surprise, he felt the steel hook digging into his body. The stranger expected him to proceed with his designated function. Any delay would be unacceptable.

Mark grabbed the girl's thighs and pulled them apart from each other as she hiked her ass in the air. He could tell from her legs that the girl was short and petite. Her ass was firm, and her legs were toned; he guessed that she was an athlete.

Mark pressed his face into the girl's relatively substantial thigh gap. Even from behind, he was able to get his tongue into her pussy. Mark reached his hands over the girls' legs and started rubbing her ass. When he tried to move his hands back to the bed, he felt a not-so-gentle tug against his rectum.

Mark circled the girl's pussy lips with his tongue as his finger provided a corresponding motion around the girl's butthole. The girl thrust her ass even further into the air almost forcing his finger to penetrate her. Again, the girl's wishes were clear even if she didn't say a word.

Mark drove his finger boldly into the skinny stranger's asshole as he flickered his tongue against her clit. Using his free hand, he penetrated the girl's tiny vagina. He could only get a single finger in between her lips, and, even then, it was a tight fit.

The girl moaned as Mark picked up his pace. His finger movement was fierce; the faster he rotated, the more the girl drove her pussy into his tongue. The girl lifted one leg behind herself and rested it on his shoulder; her other leg followed suit to the other side of his head. His hands in her ass and pussy were holding the girl in place as her thighs clenched in on his skull. The girl's body formed a bridge from the bed to Mark's face as her legs extended over the back of his shoulders.

The girl's hips rotated on Marks' face; she swung her body forward and back on the bed moving him along with her. She let out a guttural scream as her legs tightened around the sides of his head. The girl's body convulsed and seized. His head and neck hurt almost as much as his ass; His dick rubbed against the bed in front of him but refused to cum.

With a final scream, the girl relaxed on the bed allowing Mark to fall back onto the floor. He just sat there exhausted and aching. He wasn't sure he could force himself back to his knees even if he wanted to. He was spent.

Just as the guest before her, the skinny athletic girl gathered her things and quietly left the room. As the door shut behind her, the alarm clock by the bed buzzed. It was twelve o'clock.

Chapter Six

The morning light pierced the hotel curtains and burned Mark's eyes; his torso shot up responsively from the plush bed. It took him a few seconds to collect himself before finally remembering that he was in a hotel room, the same room Alison left him in the night before. He recalled that she left sleeping pills and some water on the nightstand. He must have taken the pills and passed out.

Looking at the empty glass, Mark remembered the leather strap and metal loops that were strapped to his penis. It was because of the device, after all, that he needed the sleeping pills, to begin with. He looked under the sheet at his member and was glad to see the rings and leather were gone. But how?

As Mark dropped his head back to his pillow, he noticed that he wasn't alone in the bed. A girl was lying there with her back to him. She had short blonde hair; she was wearing a pink night shirt and white bikini panties. Part of her back panty line had tucked into her butt cheek creating a thong effect.

It didn't take Mark long to recognize the pink shirt. It was the same top Brooke wore into the study room that first morning he met her. She was the first person to make him strip as part of his punishment for spying on the girls' shower.

Putting the pieces together, Mark assumed that Brooke had come into the room after he had fallen asleep. She must have removed the device from his penis then draped a sheet over him. He wasn't sure he was ready to forgive Brooke just yet, but he was glad to wake up next to her.

As Mark got out of bed, he noticed his clothes, the same outfit he removed in the study room the night before, on the chair beside him. He grabbed the pile of clothes and made his way to the restroom for a quick shower.

As Mark stepped out of the bathroom following his shower, Brooke was already dressed and ready to go.

"How's it feel?" Brooke asked.

"How's what feel?" Mark returned. Despite the shower, he was still groggy from the sleeping pills.

"Freedom," Brooke said with a smile. "You're a free man."

Mark smiled. They both knew the answer to her question.

* * * *

Just over a couple weeks later on a Monday, Mark found himself once again at his regular seat in the cafeteria. He was watching a guy sitting by himself mourning the loss of his girlfriend. Mark had watched their relationship from afar for most of the semester. They had been on and off again for a while, but Mark was somehow sure this would be it for the couple. As bad as he felt for the guy, Mark hoped the stranger realized that this could be a new beginning, a new adventure even.

On the other side of the dining hall, Mark saw Janice and Lucy. He had passed the girls around campus a few times since the end of his penance, but he had yet to speak a word to either girl. He assumed they would never talk again.

Later that day, Janice's computer would crash. She would be able to get it fixed but would lose all of her old emails and the contents of her cloud drive. Mark had heard rumblings that she was already blackmailing some other guy. If that were the case, the evidence against the other victim would be lost as well.

Mark had saved a copy of Janice's files and emails. As he dug through all the information, he found out that she had been doing a hell of a lot more than making guys strip for her. Janice was extorting money from several men, including Brooke's father, and she was cheating on virtually every one of her classes. If Janice ever made her way back into his life, he would have everything he needed to make her back off.

Mark gave Brooke all the evidence regarding her father. It turned out that Janice and Brooke's father were involved long before he ended up naked at the sorority house. He figured it would be Brooke's decision how she wanted to handle things, but he hoped she would let her father off the hook. Mark, after all, was well too aware of how easy it was to fall into Janice's trap.

Mark started gathering his things. Since it was Monday, he had a long afternoon of classes in front of him.

"Hey, stranger," a voice came from behind him. He felt cold hands wrapping around his eyes.

"Who is it?" Mark asked. It could be any one of several girls.

Emily swung her head around his and gave him a quick kiss on the cheek. "Did you miss me?"

"Uh...Hi, Emily," Mark said. He hadn't seen Emily since his first night of service a few weeks earlier.

Emily sat down next to him and wrapped her arm around his back. "I missed you the last couple of weeks."

"You missed me? I'm sorry...What is that?"

"You know," Emily said. "I miss our Monday dates."

"Our Monday dates?" Mark returned. "You know that was a one-time thing. Right?

"I do," Emily acknowledged. "It's just that I think we should get together every week."

"Every week," Mark stated. "Are you even serious?"

"I am serious," Emily insisted. "Since this is Monday, I need you in my dorm room by seven tonight."

"Your dorm room?" Mark asked. "Why would I do that?"

"Because I told you to," Emily said. "Because I told you to, and because you want to."

"But what would you make me do?" Mark asked curiously.

"Whatever I want," Emily answered. "That's how it works. You do whatever I tell you to without question."

"What about other people? Would Janna be there?"

"It would be whatever I want," Emily insisted. "That's how it works. Janna will be there if I want her there. If I invite someone else, then someone else will be there."

Mark scowled at Emily. He couldn't believe she had the nerve to ask him this. He'd paid his dues already, and she wanted more.

Emily gave Mark a kiss on the top of his head. "I'll see you at seven."

"No, you won't," Mark answered. "I'm done with that."

Emily smiled at him. "I'll see you at seven," she repeated confidently before turning and walking away from the table.

Mark watched Emily walk away from him and out of the cafeteria. Her curly blonde hair bounced freely and confidently with each step. Her short skirt swung back and forth against her thighs as her top slid up her back revealing just a hint of skin.

Mark thought about his night with Emily, how she tortured him in the movie theater and made him streak across campus. He also thought about how she rewarded him when his night was over. The image of her kneeling on her dorm room floor, naked and waiting for him, was permanently etched in his consciousness.

"Are you out of your mind?" a familiar voice sounded from behind him. "You're actually considering her demands. Aren't you?"

"Monica, hi," Mark said as his former high-school classmate joined his table. "You were listening to our conversation?"

Monica laughed. She leaned back in her chair and rested her hands on top of her head. "I'm not spying on you, Mark. I was just curious. That's all."

"It doesn't matter," Mark said. "I don't think I'll go through with it anyway."

"You don't like her?" Monica asked in reference to Emily. "She is kind of hot."

"It's not that," Mark said. "It's just that...Well, it's been a long few weeks. I just want to finish school and get on with my life. I hate it here."

"You hate college?" Monica quipped. "You think it'll be any better when you graduate? Life is what you make of it, Mark."

"Life will be better," he insisted. "I'll make it better."

"Good for you," Monica said. "What if I told you the rest of your time in college could be better too? Much better."

Mark looked curiously at Monica. She was clearly planning something which made him nervous. The last time she'd had a plan it involved tying him to a bed naked in front of his stepsister. "Better?" He asked. "How so?"

"What about Emily?" Monica followed. "I understand that she put you through the paces. Didn't you have to streak across campus for her?"