The Nerd Conquest Pt. 02

As odd as the strap felt on his penis, Mark knew the more challenging part of his preparation was yet to come; he still had to shove the rubbery plug into his ass. Mark covered the object with a thick coat of lubricant as he imagined what it would feel like penetrating his orifice.

Mark leaned forward and circled the cone around his body. He carefully covered the rubber plug with lubricant and attempted to slide the device into his asshole. It didn't fit. He applied more lube and tried again to no avail. On his third attempt, he pressed much harder. With a "pop," the plug slid into the orifice. The sensation was new to Mark. It was as though his insides were working their way back up his body. As the plug slipped into place, Mark's dick began to harden slightly against the metal rings surrounding it.

Mark could hardly straighten his torso with the intruding device still inserted into his ass. He practiced walking a few steps; it wasn't easy. Mark had to keep his legs as far apart from each other as possible as he waddled back and forth around the hotel room.

Trying to sit on the bed, the object pressed into Mark's asshole. He had to lean sideways to prevent the plug from jamming itself deeper into his body. He still had to get dressed before making his way back downstairs, a typically simple task that would be complicated by the ass plug and chastity device.

Gingerly, Mark slid his legs into the smooth tuxedo slacks. With so much hardware in his pants, He could hardly pull the zipper up and buckle his belt. After getting his pants on, he jammed his feet back into the shiny dress shoes. He would have some extra time to work his way back to the elevator, and he would need every second of it.

Mark looked down at his pants. The chastity device lifted his soft dick forward enough to tent his pants significantly, and it prevented Mark from pushing his cock safely to either side of his underwear. The situation would only get worse if, or rather when, he ended up with a serious hard-on.

Before leaving the room, Mark put his jacket back on over his pressed white shirt. Thankfully, the jacket dropped down his torso enough to conceal the bulges on the front and back of his pants.

Mark grabbed the inside handle and pulled the hotel room door open. His room was a long way from the elevator; he would have to waddle down the hall before catching a ride back to the first floor. There was no way in hell he would be able to take the stairs.

Passing several people in the second-floor hallway, Mark found himself the recipient of more than a few dirty looks. Mark couldn't tell if the other hotel guests thought he was drunk or was fighting some sort of infection. His ability to move didn't improve as he waddled along, either; the plug slid back and forth inside of him with every step he took.

Mark did eventually make it to the elevator and back to the ballroom. He didn't see Alison, Stacy, or any of their friends so he decided to find a corner and lean against the wall. Sitting down was not going to be a great option at this point.

Mark found a quiet spot and tried to stay as inconspicuous as possible. As far as he was concerned, it was up to the girls to find him. He made his way back to the ballroom as instructed. It wasn't his job to hobble around the hotel looking for Alison and her friends.

"There you are," Alison said as she shot out from a mass of people. She stepped right up to Mark and gave him a hug. As her arms wrapped around the computer science major, Alison dropped her hands just enough to check his ass plug. Squeezing him as hard as she could, she thrust her hips forward shoving her body into his ring-wrapped penis. "Very nice," she said. "You follow instructions well."

As Alison let go of him, he noticed her group of friends making their way across the crowded banquet hall. The girls, six excluding Alison, took turns giving him a big hug. Each girl grabbed onto his ass and jammed her torso into his center. By the time all hugs were exchanged, he felt his dick growing rapidly through the multiple rings.

Watching the girls, it was fairly obvious to Mark that this was not their first time participating in such an activity. They had their routine planned out and timed to perfection.

"Let's go dance," Stacy suggested to the group as a slow song started playing.

"Let's do it," Alison said grabbing Mark's hand and moving him toward the dance floor.

It was only a matter of seconds before each of the girls had a dance partner. Stacy even turned down two different guys before settling on someone.

Once on the dance floor, Alison pressed her body against Mark's. She rested the side of her head on his neck. She then wrapped her hands under his arms and hooked her fingers over the back of his shoulders. He clasped his hands together around the small of her back. As awkward as his accessories felt on his dick and in his ass, he savored being so close to such a beautiful woman.

As the couple swayed to the music, Alison pressed her body deeper into Mark as if she was trying to merge and become a single entity. His erection grew; the rings around his dick allowed the blood to flow into his cock but prevented his fluids from escaping.

Alison moved her hands together around Mark's back and gently raked her fingers through his hair. Her head still resting on his shoulder, she sang softly along with the music; her near perfect pitch penetrated his tuxedo jacket and rippled across his chest. For a moment, he let his guard down and enjoyed her company.

"Hey, Mark," Alison said in a soft voice.

"Yeah," returned Mark. "What?"

"You're not such a bad guy after all. Are you?"

"I don't think so," Mark answered.

"Mark?" Alison continued. "Do you like me? I mean could you ever see yourself with someone like me?"

"You and me? I don't..."

Alison interrupted Mark mid-sentence grabbing his balls through his tuxedo pants. She didn't squeeze to the point of hurting him, but he wasn't expecting the sudden grope.

"Ahhh," Mark pushed back from Alison in surprise.

Alison pressed her finger over her lip insisting that Mark not make a scene. She pulled his body back close to hers swaying once again with the music.

Alison and Mark continued to dance; his movements were slight at best as he clenched his ass around the butt plug and pressed his knees together. He noticed Alison's friends with their guys forming a circle around them. The surrounding bodies created a privacy wall allowing Alison more leeway to play with her date.

Alison leaned into Mark once again and whispered into his ear. "Do you like my ass?" she queried.

"Sure," Mark whispered back. "I guess so."

"You guess so?" Alison retorted. She reached down to Mark's ass and jammed the plug further up into his asshole. "You guess so?" she asked again.

"I do," Mark added. "I like your ass very much."

"Then why don't you grab it?" Alison said. "If you like it so much, why don't you grab it?"

Mark took his right hand and let it slide down Alison's back until it rested against her left cheek.

"Is that what you call a grab?" Alison scoffed. "You can do better than that."

Mark dropped his other hand down to Alison's ass.

"Grab," Alison said. "Fucking grab my fucking ass."

Mark squeezed Alison's ass cheeks with both hands.

"I won't ask you again," Alison said. "Grab it, and grab it like you mean it."

Mark squeezed her ass even harder with both hands; he could feel her cheeks pulling apart from each other as his fingertips slid into her crevice. He ground her body into his own as his dick pulsated through the metal rings.

"That's more like it," Alison said. "Do you like my tits?"

"I do," Mark said breathing heavily and pressing his forehead into Alison's hair. "I like your tits."

Mark slid his arms between their compressed bodies cupping each hand over its corresponding breast. He could feel her nipples poking through her sheer red dress and into his palms. She wrapped her arms tightly around him securing their bodies against each other.

"That's not grabbing," Alison whispered into Mark's ear.

Mark squeezed Alison's tits so firmly that he worried about hurting her. The harder he groped, the tighter she pulled into his body. She rotated her hips against his throbbing center. The metal rings and leather rubbed up and down Mark's erect cock.

"Do you like my pussy?" Alison asked Mark.

Mark didn't answer. He took one of his hands and wrapped it around Alison clutching her tight ass; he slid his other hand down her rippled stomach and over her snatch. When Alison's tight dress prevented Mark from reaching between her legs, he pulled the front of the dress up and slid his hand underneath.

Alison's skimpy thong did little to protect the brunette's pussy from Mark's intruding fingers. He jammed his index and middle fingers beneath her underwear and began rubbing her already wet pussy lips. He rested his head on her shoulder and watched spots of light from the disco ball circling the room. Her body slid downward into his fingers as they penetrated her cunt.

Losing himself in exhilaration, Mark failed to notice Alison unbuckling his pants and sliding her hand into his underwear. His slacks almost fell down his legs as she grabbed his cock firmly and started stroking up and down. Keeping one hand between her legs, he used the other to secure the back of his belt against his ass. She pulled their bodies closer together while pumping furiously up and down his cock.

Mark felt like he was about to cum, but the metal rings around his penis delayed his climax. His body burned as blood rushed to his center. Even though separated by layers of formalwear, Alison's pussy pulsated in synchronicity with his penis.

Mark's knees almost collapsed in on themselves as semen shot through the metal rings and into Alison's fist. Alison let her legs go limp and pulled him down knees first to the temporary dance floor. Fearing the crowd's reaction, he squirmed feverishly around on the wood surface as he returned his pants to their buckled state.

As soon as Mark's pants were back in place, Alison leaned into his ear and whispered his next set of instructions. "Find a bathroom and get yourself cleaned up. We'll see you back at the room in fifteen minutes."

Still kneeling on the dance floor, Mark watched Alison and her group of friends retreat from the party and into the hotel lobby. Once the girls were clear of his line of sight, he forced himself to his feet and found an empty table. He wanted to compose himself before embarking on the next leg of his adventure.

Mark fought to regain his focus as the party continued around him. Everyone must have assumed he was simply drunk and needed a minute. His ass burned from the butt plug; his dick felt limp and sticky against the leather strap and metal rings. He realized that he had to get moving if he was going to make it back to the hotel room before Alison's deadline.

On his way to the elevator, Mark found a restroom and took a couple of minutes to clean up the sticky mess in his pants, or at least he made a valiant attempt to do so. By this point in his week, he didn't figure to be surprised by much. Even so, Alison's public display of affection threw him off. More so, he was grateful they didn't get into trouble with hotel security.

Mark made his way to the elevator and to the second floor. Along the way, he tried to remember where he would be meeting Alison at. When he followed Stacy to the room earlier that evening, he never thought to get the room number. Now he had to figure out which unit the girls were occupying based on how far their room was from the elevator. Unfortunately, all the entryways looked exactly alike, and he didn't want to start knocking on random hotel room doors.

Mark paced up and down the hallway trying to remember anything about the room he was in earlier. Just when he was about to give up and go door-to-door, Stacy peeked her head out correct door. She waved for him to hurry up and join her.

When he entered the room, Mark saw Alison lying on the bed and reading something on her phone. At the base of the bed, he noticed a rope hanging down from the ceiling. The cord connected to a small pulley that someone must have bolted to the ceiling.

"There you are," Alison said without moving from her spot on the king-sized bed. She was still fully dressed including her stiletto heels. "That was more than fifteen minutes."

"Sorry," Mark said looking down at his feet. He rubbed his polished black shoe into the expensive carpet. "I got lost."

"Well, hurry up and get undressed," Alison said. "We don't have a lot of time."

**The Final Task**

Alison and Stacy looked on as Mark obediently took off his jacket and started unbuttoning his shirt. As he removed his clothing, he reminded himself that this would possibly be the last time he would have to strip on command. In just a couple of hours, his time with Alison would be over, and his penance for spying on the girls' shower would be concluded.

Once Mark was completely naked, Alison instructed him to go into the restroom and remove the plug from his ass. He was grateful that she was letting him take it out and even more thankful that she was giving him some privacy while he did so.

Mark took his time in the restroom. As curious as he was to find out what Alison expected him to do next, he mostly just wanted his night of service to be over. The rope tied to the ceiling in front of Alison's bed didn't do much to motivate him either.

"That took you long enough," Alison said as Mark finally stepped out of the restroom. "We were worried your plug might be stuck."

"Sorry," Mark said even though he wasn't. "It's just been a long night."

Stacy took Mark's hand and led him to the foot of the bed. "Stay right here," Stacy commanded leaving him with his legs pressed against the mattress.

Mark caught Alison's eyes as she giggled and glanced down at a large hook lying on the bed beside her. The item looked like an oversized fish hook with a small steel ball in place of a sharp point. He wasn't sure what the hook was going to be used for, but the look on Alison's face told him it wouldn't be good.

Stacy stepped behind Mark and reached over his head. She strapped a leather collar around his neck and threaded the rope from the ceiling through a loop in the leather band.

"Okay," Stacy said as she grabbed Mark's shoulders. "I'm going to need you to lean forward against the bed."

Mark followed Stacy's instructions resting his chest on the mattress with his butt elevated into the air in front of Stacy. Now he knew exactly what the hook was for.

Stacy grabbed the steel hook from the bed and covered its tip with lubricant. She then walked slowly around Mark's bent-over body. He couldn't force himself to watch as he felt her cold hand made contact with his naked back. Instead, he closed his eyes and braced himself for the inevitable penetration.

Mark could feel the rope sliding up and down the loop in his collar as Stacy was presumably tying the rope to the large butt hook. Each time the line pulled against his neck, he waited for the cold steel to make contact with his orifice.

Mark felt Stacy's pointer finger and thumb separating his ass cheeks in preparation for his hooking. With a sudden plunge, he felt the cold steel sliding smoothly into his puckered hole. The hook dug even deeper into Mark than the rubber plug did earlier.

As soon as the hook was successfully inserted, Stacy helped Mark back up to his feet. He could feel the hook pressing into his butthole. The rope connected to the hook slid up through the pulley and back down over the bed into Alison's firm grip.

"Perfect," Alison said as she watched Mark fight off the effects of her initial tug. "Now get on your knees."

Mark dropped to his knees as instructed. As he knelt down at the foot of the bed, the rope pulled back through the pulley and lifted Alison's hand into the air. She smiled as she gave the line a couple of gentle tugs forcing him to squirm around on the floor. His firm dick filled the metal rings of his chastity device; he shuffled back and forth on his knees trying to find the least uncomfortable position.

Alison swiveled her head toward Stacy, who took the hint and left the room. Alison needed some time alone with Mark.

Alison slid to the end of the bed and pulled Mark between her legs until his face was mere inches from her chest. The brunette reached behind herself and pulled out a black sleeping mask; she wrapped the mask carefully around his head so as to completely impair his vision.

"I'm afraid this is where we part ways," Alison said to Mark gently. "Are you ready for your final instructions?"

"Sure," Mark responded curiously.

"I set the alarm for midnight," Alison said. She caringly brushed her hands through Mark's hair. "When it goes off, you may get up and remove your mask. There are two sleeping pills and a glass of water on the bed stand. If you take the pills and go to sleep, someone will be in here to remove the strap from your dick. If you try to remove it while still erect, you might hurt yourself. Got it?"

"Sure," Mark said. "I got it."

"Good," Alison continued. "I'm going to leave you here for now. Over the next couple of hours, you may get some visitors. If company does show up, you will be expected to tend to their needs. You may only use your mouth and your hands to get them off. It is entirely possible that no one will show up. If that's the case, just stay there on your knees until the alarm goes off. Got it?"

"Got it."

"My friends value their privacy," Alison continued. "Under no circumstances are you to remove your mask. They will not offer to have sex with you, and you will not ask them to do so. You are here to take care of them. Period. Got it?"

"I got it," Mark answered. "Don't remove the mask."

"Good," Alison responded. She brushed the side of his face with the back of her hand. "One more thing. My friends won't say anything to you. They'll just come in, let you take care of them, and then they'll leave. If they're not happy with your performance, they'll pull on this rope." Janice paused and gave the line a quick tug. "So we're good?"

"Yes," Mark answered. "We're good."

"Well then," Alison said. "That should do it for us. Have a nice life."

Mark remained on his knees listening intently as Alison moved around the hotel room. He could tell she was gathering her things and preparing to leave him. In a way, her demands reminded him of his Monday night at the movies with Emily. Once again, he found himself wearing a mask, and, once again, he wouldn't be getting off.

Mark let his butt drop to the back of his calves as soon as he heard the door close behind Alison. Even if he was kneeling on the carpet with a strange contraption on his dick and a hook in his ass, Mark was grateful for the time alone. He listened carefully as strangers walked up and down the hallway outside his room. With each set of footsteps, Mark waited to hear a click at the doorway as the lock protecting his privacy gave way to a stranger.

Mark could hear the mini-fridge directly behind him. It buzzed every few minutes as the motor struggled to compete with its worn out seal. The area smelled of sanitizer and air freshener, a dead giveaway for even the finest hotel room. While not unpleasant, the odor reminded Mark that he wasn't home.

The clock slowed down for him. He had always been someone who valued time, who had appreciated and understood the distance between one life event and another. The past week had felt as if it was much longer than most, and the next couple hours could be the longest span of the current week.

As time passed, the burning in his ass calmed as did his artificially elongated erection. Could he dare hope to spend the rest of his time alone?