The Nerd Conquest Part TWo Read online

  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?

  “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.

&
nbsp; 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?