by C. W. Niess
Stacy lifted the bottom of her dress up her legs enough to kneel down in front of Mark. She lifted the device to his mid-section as if she were a model showing off a game show prize.
Mark listened carefully to Stacy’s instructions as to how the chastity device worked.
“You’ll need to deal with the erection before putting this on,” Stacy said with the slightest of smiles. “Take this big ring on the end here and slide it all the way down your dick then loop it behind your ball sack.” She pressed the largest ring against the base of his penis for the purpose of illustration. “These other rings just wrap around your dick.” She held his cock in her hand showing him precisely where each of the loops needed to go. “Got it?”
“Yeah,” Mark said. He was embarrassed by his growing erection but wasn’t about to call attention to himself. “I got it.”
“Okay then,” Stacy said placing the contraption on the bed beside Mark. “When you’re all set, get dressed and meet us downstairs. I’ll let you go ahead and get ready.”
“Sure,” Mark said. He sat on the bed and casually crossed his hands over his lap. “Uh, thanks.”
“No problem,” Stacy smiled. “I’ll see you downstairs. Alison expects you back in the ballroom you by eight thirty.”
Mark checked the time on the bedside alarm clock as Stacy stepped out of the room. He had more than thirty minutes before he had to meet Alison back at the party.
Mark spent most of his free time trying to figure out exactly how the device with the leather straps and metal loops would affect him. He remembered Stacy telling him that he should take care of his erection before putting the contraption on. Looking down at his hard dick, he decided to follow her advice.
Mark grabbed a few tissues from the bed stand and started stroking himself furiously. Less than a minute later, his erection problem was solved. After giving his penis a few minutes to relax, he carefully slid the largest loop down his stem and around his sack. Mark then moved the other loops along his dick and into their respective positions.
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 o
ver 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.