The Nerd Conquest Pt. 02

"And he doesn't know who you are," Monica lied. "Now let's get those tights off."

Mark felt his dick growing hard once again as his stepsister stood up from her chair and pushed her black tights down her skinny legs. Mark looked around nervously and caught Monica smiling at him. She was enjoying her game and taking in his every reaction.

"Panties too," Monica demanded immediately as Alicia stepped out of the tights.

Alicia obeyed with little hesitation. Mark couldn't look away as his stepsister hiked up her long sweater to grasp the sides of her panties. He caught a brief look at her blonde bush as the panties slid down just ahead of the descending sweater. Mark knew it was wrong to watch his stepsister undress, but he wasn't about to turn away.

"Good girl," Monica said as she cleared her desk. "Now lean over here so Mar...I mean the birdman can get a good angle."

Alicia nervously approached the desk and bent over it extending her butt into the air. Monica stepped behind the blonde and pulled Alicia's sweater up her back completely exposing Alicia's skinny white ass cheeks. Monica tucked the sweater under the blonde's metallic gold belt so it wouldn't drop back over her ass. It looked awkward, but the sweater was sure to hold its place.

"You're up, Mr. Bluebird," Monica said to Mark, who still had his legs crossed under the pillow.

Mark was embarrassed to get up and let the girls see his erection even if it was hardly a new development. While he didn't care for Monica seeing him aroused by the prospect of spanking his own stepsister, he obeyed her instructions.

Monica extended her hand toward Alicia suggesting that Mark should get on with his assignment, twenty swats on her naked ass.

Mark slapped Alicia's butt lightly.

"That's not gonna cut it, birdman," Monica insisted. "Better make the next one count, or you're going over the desk next."

Realizing Monica was serious, Mark hit Alicia much harder with the second smack.

"Ahhhh," Alicia responded.

"Getting there," Monica assessed. She rested her hands on her hips with a giggle. "Needs to be harder than that, though."

"Ohhhh, shit," Alicia squealed after the third smack.

"There you go," Monica said with a quick slap on Mark's own naked ass. "Now finish her off."

"Four," Monica counted as Mark took another swing.

"Please," Alicia yelped with the fifth smack, her white cheeks now a bright red.

"Six," Monica counted. "Seven...Eight...Nine...Ten..."

Mark felt bad for Alicia, but he knew it would be much worse for her if she realized the stranger spanking her was actually her older stepbrother.

"Ahh," Alicia cried with the eleventh swat. Mark saw her eyes watering as she looked back at him hoping for mercy.

Mark continued with the next four smacks before pausing briefly. His stepsister whimpered in pain; Mark wanted to stop.

"Five more to go," Monica demanded. "Just five more."

"Slap," Mark hit his sister's ass for the sixteenth time.

"Ahhhh," Alicia yelled. Her ass was blood red.

"Slap...Whack...Slap...Slap," Mark hit his sister's butt four final times in quick succession.

Alicia immediately pulled herself off the desk letting her long sweater fall over her burning ass. "Can I...Can I get my tights?"

"Sorry," Monica returned. "You'll get them when we're done."

Alicia didn't argue. She just slowly walked over to the bed and sat down gingerly.

"This is bullshit," Tina said realizing it was her turn.

"We'll see," Monica joked as she handed her younger sister the jar. "What's in store for you and our birdman?"

Mark watched Tina as his childhood nemesis pulled a slip of paper from the glass jar. Mark thought about how great it would be to spank Tina's bare ass. He would love any small measure of revenge for all the terrible things Tina had said about him and done to him over the years.

Tina held the note so only she could read it. Then, with a panicked look on her face, she closed the note, stood up, and started pacing the room. Tina wasn't happy with what she was expected to do.

"What is it?" Monica asked her sister.

"It can't be any worse than mine," Alicia added. "Can it?"

"Fuck this," Tina said as she continued to pace the floor. "Fuck this. Fuck this."

"We can call it a night and upload those pictures," Monica insisted. "Or the two of you can finish these dares and go home."

"But, I just can't do this," Tina demanded. "Let me pull another card."

"No do-overs," Monica demanded. "What's your note say?"

"It says he gets to shave my pussy."

"That's not so bad," Monica argued with a smile. "From what I remember, you keep little Tina neat and trim anyway."

"Come on, Tina," Alicia encouraged. "I already let him smack my ass twenty times. We only have three more notes then it's all over. Monica will delete those pictures of us too."

"Promise?" Tina begged her sister. "You'll delete all the pictures?"

"All of them," Monica insisted. "I promise."

"OK," Tina relented. "I'm gonna get you for this, Monica. I promise you that."

"Sure you will, Tina. Now, go ahead and lose those jeans while I get you some warm water." Monica left Mark in the room with Tina and his stepsister. Mark couldn't even process what was about to happen.

Alicia held down her sweater as she slid off the bed to make room for Tina. Alicia carefully walked past Mark and took a chair; she wasn't about to show off any more of her body than the masked man had already seen.

"I'll bet you just love this," Tina snapped at the anonymous naked guy about to shave her cunt.

Tina unbuttoned her blue jeans and folded them neatly on her chair. She was wearing a light blue thong that almost perfectly matched her tank top. Holding a hand over her crotch, she slid the thong down her legs and let it fall to the floor. Leaving her underwear on the ground, she walked carefully to the bed and lay down on her back. She kept her hands crossed over her pussy careful not to expose herself to the bluebird or even to her best friend.

After a few minutes of silence, Monica returned with a pan of hot water, a pair of scissors, a razor, and a wax kit.

"Well, let's see that there bush," Monica joked at her sister's expense.

After a short pause, Tina closed her eyes and let her hands fall to her sides. As one might expect from a girl her age, her pussy was well groomed. She did have a visible bush of jet-black hair, but it was recently trimmed and shaped.

"It's all yours, Mr. Bluebird," Monica said as she sat in one of the chairs and extended her arm toward Tina's exposed vagina.

Mark leaned over the bed and inspected Tina, the terror of his childhood, lying exposed in front of him. For the first time in his entire life, Mark had the upper hand with her. Part of him wished she knew exactly who was about to shave her pussy. Unfortunately, she could never find out.

Mark grabbed the scissors and pulled Tina's shirt up her stomach. Her hands moved to stop Mark's wardrobe adjustment, but she immediately withdrew her defense. Tina was resigned to her wet shave.

Using the scissors, Mark clipped Tina's pubic hair as close to the skin as he could. He pulled her legs open to get a better angle, a move she once again momentarily protested. He made no attempts to avoid touching her pussy. His fingers were in almost constant contact with her exposed lips.

Once done with the scissors, Mark grabbed the razor and some shaving cream. He carefully shaved the area around Tina's pussy. He fought to keep his shaking hands steady as the razor journeyed around her soft lips. Mark disliked Tina, but he didn't want to cut her skin. After the shave was complete, he stepped back to inspect his handiwork.

"That's not smooth enough," Monica demanded. "You're gonna have to use the wax."

Mark took the jar of wax from the warm water and scooped a dab with the wooden spatula. Monica stepped up to help Mark apply the wax and make sure he didn't permanently injure Tina's pussy. Then Monica demonstrated how to apply the first strip.

"There you have it," Monica said. "Now just rip that sucker off."

Mark looked Tina in the eye. He wanted to hit pause on this moment so it could somehow last longer.

"No, please," Tina begged as he peeled the strip's edge away from her skin. "Please don't...Ahhhh."

The first strip was off. Tina started to cry more out of embarrassment than physical pain. Mark applied another strip with some wax and yanked a second time. Then he did it again, and again, and again, and again.

"Wonderful job, Mr. Bluebird," Monica said as she inspected her sister's perfectly smooth yet visibly sore vagina.

"That's it, girls," Monica said as she helped her sister up. "Two dares down and two to go."

"Haven't we had enough?" Alicia asked. The dirty blonde knew she was next.

"One more and you're done," Monica assured Alicia. Monica handed Mark's stepsister the glass jar. There were two lonely green strips of paper remaining, one for Alicia and one for Tina, who was presently hunched over trying to catch her breath. "So let's do this," Monica said coaxing Alicia to choose a note.

Alicia reached nervously into the jar and selected one of the remaining slips of paper. "Ass," she said curiously. "That's all it says."

"Good choice," Monica joked. "That means you get his ass."

"Get his ass for what?" Alicia asked.

"Let's let Tina read the other paper first, shall we?" Monica replied as she handed Tina the glass jar. "Then I'll explain how our game ends."

Tina drew the final sheet of green paper. "Cock?"

"That's right," Monica said to Tina. "You get the cock."

"Yeah," Tina responded sarcastically. "But what the hell does that mean?"

"It's simple," Monica answered. "Alicia is going to lick our friend's ass while you give him a blowjob."

"What?" Alicia snapped back into the conversation. "I'm not licking his fucking ass."

"Oh, but you are," Monica insisted. "You'll lick his ass while my sister sucks him off, and you'll keep going until she's swallowed every bit of his cum."

"Swallowed!" Tina yelled. "I have to swallow his junk?"

"That's right, girls," Monica insisted as she picked her phone back up. "Get on it now or I'll upload those pictures."

"Let's just do this," Alicia said to her best friend. "We do this one thing then we're done."

"Okay," Tina relented. "But this is it."

"This is it," Monica repeated in assurance. "The game ends here.

"You're gonna pay for this, Monica," Tina again promised her older sister as she knelt down in front of Mark.

Alicia didn't say anything. She just dropped to her knees behind Mark staring into his ass. She could see some of the leftover lubricant from her previous encounter.

Monica approached her three guests from the side and grabbed the girls by their hair. Monica thrust their faces into Mark's body and their respective assignments.

Mark felt his stepsister's tongue tickling his butt crack as her hands wrapped around his legs for balance. The tongue intruded even more so as Monica pressed Alicia's head deeper into his ass. Just as he adapted to his stepsister's tongue in his crack, he felt Tina's warm moist lips cautiously wrap themselves around his sore growing penis.

"That's it, girls," Monica encouraged. "Neither of you stop until Tina swallows every bit of his load."

Mark closed his eyes. His stepsister's tongue traveled up and down his ass while Tina plugged her vile mouth with his now fully-erect penis.

"Keep quiet," Monica whispered into Mark's ear. "I'm going to take your mask off for a minute, but I'll give it back."

Mark wanted to protest but couldn't. Monica ripped the bluebird mask off his head and stepped away from Mark's threesome.

All Tina had to do was look up, and she would see exactly whose dick she was sucking. Mark's identity could be exposed at any moment.

"Please...Please," Mark mouthed toward Monica begging for the mask back.

Instead of returning the mask, Monica laid it down on her desk. She smiled deviously at Mark, who could only look into the air hoping the girls didn't do the same.

Tina grabbed Mark's hips as she pumped her mouth up and down his rod. Alicia, in a show of solidarity with her best friend, rested her hands on top of Tina's. The girls moved in unison like a team of lumberjacks sawing down a mighty oak. They swayed Mark's body back and forth from Tina's mouth to Alicia's tongue and back again. His dick would push down Tina's throat in one motion then pull out as his ass fell back on Tina's tongue. Back and forth, Mark shifted from girl to girl.

Mark's penis was throbbing and burning. It would only be a matter of seconds before he would lose his load in Tina's mouth. She would assuredly look up and recognize him. Mark had to get his mask back.

Monica held the mask up taunting him with it as he fought to control his ejaculation.

Once again, Mark quietly begged Monica to show him mercy. "Please. The mask. Please."

Monica approached him as he fought against blowing his load. She reached around his body and pulled the mask onto the top his head; his face was still exposed. "Do you trust me?" she whispered into his ear.

Mark nodded in agreement as his body swayed between the girls below him.

"I can't hear you," Monica said.

"Yes," Mark whispered as he felt his ejaculate fighting to escape.

"Still can't hear you," Monica replied again.

Mark looked down at Tina's black hair as she bobbed up and down his cock. He was about to fill her mouth with his cum. "Yes," he whispered more loudly.

"Yes, what?" Monica asked.

"Yes," he whispered again. "Please. I trust you."

At that very moment, his resistance gave way and his penis exploded semen down Tina's throat and all over her face.

"Gahl...ahll...gahl," Tina gurgled as she choked down his load.

Just as Tina looked up in disgust, Monica pulled the bird mask down over Mark's face. He hoped Tina didn't get a good look at him.

"Not yet, Alicia," Monica demanded as the blonde pushed away from her brother's ass. "Keep licking until Tina finishes cleaning up our birdman's cock."

"Hurry up, Tina" Alicia mumbled into Mark's ass.

After making Tina thoroughly lick his dick clean, Monica declared her game over.

Tina and Alicia rushed to get dressed, and Monica told them to go take another shower so she could "settle up" with their guest.

As soon as Tina and Monica were gone from Monica's room, Monica pulled the mask off of Mark's head for the last time.

"You're done here," Monica said to him. "Thanks for being such a good sport."

Mark realized he would have to make his way back to the study room completely naked and without the mask, and he would have to move carefully. After making it through the night with his identity hidden, he didn't want to run into his stepsister and her best friend by the showers.

"Hey, Mark," Monica interrupted as he grabbed for the door.

"Yeah," Mark responded impatiently.

"Do you know the difference between you and the guys I dated in high school?"

"About three years on the football team and twenty pounds of muscle," Mark answered.

"That's fair," Monica said. "There's more to it, though. The main difference is that they had the balls to ask me out."

"So you would have gone out with me?" Mark asked.

"We'll never know," Monica insisted with an evil grin. "You never asked."

Mark had no idea how to respond, and he wasn't about to wait for Alicia and Tina's return. Instead, he nodded goodbye and stepped out of Monica's room. As he made his way down the hall, a couple of girls clapped and whistled, but he was too tired to react or to even care. Seconds later, he found himself back in the study room fighting to get dressed once again.

Mark stumbled back to his own dorm room and dropped to his bed.

Mark thought about what Monica said as he left her room. He convinced himself that she either felt guilty for putting him through so much or was playing some sort of mind game with him. Knowing Monica, it was certainly the latter. He could never date a girl like her. Could he?

Mark went to sleep with a smile. No matter what happened from here on out, he would always have the memory of Tina choking down his cum. That mental picture alone could get him through hell and back.

Chapter Four

Mark woke up Thursday morning after the most restful sleep he had in a week. Despite how well things worked out with Monica and his stepsister the night before, he was thankful his time of service was nearing its end. He had one more night ahead of him, Friday night with Alison; he knew his time with her would possibly be his toughest challenge of all, but after that, his suffering would be over.

Lucy and Janice promised Mark that if he followed through with their plan for this week, his debt would be paid in full. He had to spend Monday, Wednesday, and Friday with different girls, and he was expected to do exactly as his hosts instructed. If he did so, Janice and Lucy promised they would never make the video of him spying on the women's shower public.

All along, Mark had worried that Janice or Lucy would decide to extend his time of servitude beyond the current week. Since they had the incriminating videos, there would be little to preclude them from adding time to his sentence or making new demands altogether? Thankfully, Brooke offered Mark an opportunity to secure some insurance against such additional requirements.

Brooke helped Mark break into Janice and Lucy's room and log on to Janice's computer. He was able to install tracking software that would hopefully grant him access to Janice's files. If he could get to the damning videos, he could ensure the end of his servitude once and for all.

Even before taking his morning shower, Mark booted up his own laptop to see if he had access to Janice's cloud drive. Using the keystroke program that he loaded onto her device, he would eventually be able to steal her password; she only had to type the security code into the drive herself before he could see it. If everything went according to plan, she would never know who deleted her files.

As part of Mark's arrangement with Brooke, he had agreed to also remove the embarrassing content Janice had collected from her father, a former professor at the college. It was the least he could do in return for her assistance.

Part of Mark wanted to delete all of the files on Janice's computer before his Friday evening rendezvous with Alison. Considering what happened during his first encounter with her, he worried about what she might demand of him when given more time to prepare. While he had no idea what exactly to expect from his final host, he was afraid he was in for a terrible Friday night.

Despite his concerns about Alison, Mark realized that cutting his service short could potentially provoke Lucy and Janice. Even if he managed to destroy the incriminating videos, there were plenty of witnesses to his crime. He also had to make absolutely certain that there were no offline copies of the videos. Caution had to be his first priority.

Another part of Mark, a part he would never admit to, was curious about what Alison would demand of him on Friday night. While he would never admit to enjoying his time with the girls, it certainly added some excitement to his senior year. Was he going through with his final night of service because it gave him the best chance of escaping Janice's blackmail, or did he actually want to subject himself to Alison's demands? For that question, he didn't have a simple answer.

To Mark's disappointment, Janice had yet to log into her cloud drive. She had been using her computer the night before, but she had only checked her email. Mark figured he would go through her online correspondence later. For now, he had to get ready for class.

Mark brought his laptop with him that morning so he could check in on Janice between classes. He might even be able to snoop around her hard drive after his first-period test; ironically, he was taking the literature exam that had been canceled the Thursday before.