The Kinksters are Alright

Sometimes writer's block hits you hard and then life gets in the way. It's been a while, but here we are having some fun with Jack and learning a little more about why he is the way he is.

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Chapter 18 - Jack

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The desire to be submissive, abused and sexually deviant were the things that came way too early for Jack. As a kid, he struggled to find outlets for what he was feeling. Rather than make friends, Jack made himself a target and purposely put himself in bad situations. However, his ability to maintain a happy, outgoing personality throughout his life is also rooted in his childhood. None of the adults around him knew he was a messed up kid. Not very different from the people around him now, as an adult, not knowing what Jack does behind closed doors.

It’s no wonder Jack has struggled so much of his life with deep, dark depression. He lost his virginity at 16 to a landscaper he crushed on and watched work around the yard. The guy caught him jerking off and ogling at him and basically raped him. As a junior in high school, Jack thought he was going to have a good time with two guys he met at the park. They were both in their 30’s and were actually pretty attractive. They brought Jack to a motel room in a shady part of town. After taking turns fucking him and making him suck them off, they eventually became very rough, which didn’t scare Jack at first. Eventually the two men took  turns beating Jack up. He barely escaped before they were able to seriously hurt him. These are just two examples of how Jack managed to put himself in dangerous situations.

In Jack’s senior year, he crushed on a boy who played football. He followed this kid to games and practices. He tried to remain discrete, and was mostly successful. The hot boy never actually knew Jack was watching him and never met him. Some of the players on the team were among Jack’s worst bullies and following that boy around got him in frequent trouble. Jack was eventually caught by the coach and that didn’t go well for him. 

Coach Lyle Beatty was a hunk of a man. He was 28 years old, 6’7” and 220 pounds of pure muscle. He wasn’t very good looking, he had a rough appearance, sort of like Jaws from the James Bond movies. He was all power, strength, energy and ego. Most people thought he was kind of a dick with his arrogant attitude. The school put up with him because he was the best - and he knew it. He was hired by the school to be the football coach to make sure they always had the best team. 

Lyle noticed Jack always hanging around the practices and games. He noticed how Jack got into scruffs with other boys in school. He saw that Jack was a weak, scrawny boy - just the type of boy Lyle got off on doing bad things to. Lyle was gay, but being the super sports stud he was, he could never act on it or show it. He needed to find a release for his pent up sexual energy. Typical of the guys like him, he preyed on young boys and knew he could just take what he wanted and get away with it.

One evening, after practice was over, Coach Lyle walked over to Jack, who was hiding behind the bleachers. 

“Hey! You! Scrawny boy! Come over here.”

“Me? Am I in trouble? Sorry Coach, I was just leaving.”

“No you’re not. You’re coming over here. Right. Now.” Coach Lyle pointed to the ground directly in front of him.

Jack’s adrenaline was running through him. He was afraid of this hulking man yelling at him, and was worried what he might do to him. At the same time, he also felt a little excited about what he might want from him. Jack was aroused from being barked at by this beast of a man. It really didn’t take much to hide it. Jack walked over to the coach and simply cowered in his presence.

“What is your deal, kid? You are here every day. You let these guys work you over, beat the fuck out of you, and then you come back for more. You like this? You some kind of freak?”

“Uh, well. I, uh, I am…I do?”

“Is that a question? You don’t know if you like getting your ass kicked every day?”

“I guess I don’t really know. I think I do. I’m sorry, I’m weird. Can I go now?”

“Oh fuck no. If you want your ass kicked, you’re really going to get your ass kicked. You’re coming with me,” the coach said firmly as he put his huge hand on Jack’s wiry shoulder and nudged him towards the supply shed.

Jack’s emotions went back and forth between excitement and fear. The prospect of this man destroying him was hot as long as it was just a fantasy. Now that it seemed there was something about to happen, it made Jack nervous. The boys were rough, but they really didn’t hurt Jack all that much. This guy was a monster. He was huge and probably super strong. He probably could do real damage, or worse. If he just wanted to beat on him, it would be bad. Very bad. Even if he wanted to fuck Jack, that wasn’t going to be so great either.

“R-r-really, I gotta get h-h-home.”

“I’ve seen you here later than this. I’ve been watching you closely. Don’t fuck with me. You have time. You will make time, you little freak.”

The supply shed was off to the side of the field and very out of the way. It was completely hidden from the rest of the schoolyard. No one would notice anything happening here. It was where the teams stored their gear and uniforms. The Coach led Jack into the shed and closed the door behind them.

“I’ll bet you’re a virgin. What are you, 14? 15?”

“I’m 17.”

“Nice. Almost legal! Take your clothes off, faggot.”

Jack was shaking. He was scared. His sex drive was in full force, but he also feared for his life. He slowly removed his clothes as Lyle leered at him. Coach Beatty literally towered over him. Jack was barely 100 pounds and a very scrawny 5’10” tall. He was skin and bones and at the mercy of this giant. Finally, Jack was naked. His little boy cock was harder than it had ever been and was dripping with precum.

“I see you’re excited. Good. You should be. This is going to be exciting. Certainly for me.”

Lyle ran his huge hand through Jack’s hair. He then grabbed Jack by the throat and lifted him off the ground. He looked Jack over as if he were inspecting a piece of meat. He grabbed Jack’s crotch and what little was there and squeezed it. Jack thought he was going to rip his genitals off him. Coach Lyle finally dropped Jack to the ground and demanded he get on his knees. The Coach grabbed Jack’s head and shoved it into his crotch. Instinctively, Jack rubbed his face in it and felt his way along the hard rod that was inside of the Coach’s sweatpants. He could tell it was enormous, bigger than anything he’d ever imagined. 

“Turn around and reach for your ankles, kid.”

“Um, p-p-p-please…don’t…“ Jack was shaking and beginning to cry. He was scared of what was about to happen. He was powerless to do anything about it. It was the landscaper, the guys in the hotel, all over again.

“Shut up and do what I said. I don’t care about you. You’re going to do what I want right now.”

Jack once again, did as he was told and bent over grabbing his ankles. Lyle dropped his sweatpants and revealed a monster cock that was as long, hard, and thick as a baseball bat. He spit repeatedly on his hands and lubed up his cock. He spit some more and rubbed it on Jack’s ass, poking his finger into Jack’s tight hole. Jack stood straight up at the fierce pain he just felt. Lyle just forced him back down again with his free hand, slamming his face onto a shelf.

A little more spit and the Coach lifted Jack off the ground by his hips and impaled Jack down on his cock. Jack felt the worst pain of his entire life as Lyle forced his cock into him, showing him not even a hint of mercy. Jack let out a piercing, distressed scream nobody other than the two of them would ever hear. Lyle forced Jack all the way down on himself, ripping his hole open. Jack screamed as loud as he could as he kicked his legs and flailed his arms. He cried and sweated as he was being violated but this monster. Lyle was relentless. He even laughed at Jack’s agony, encouraging him to scream louder. Jack was overcome with pain to the point of nearly passing out. Lyle was grabbing onto Jack’s bony hips and just pounding his ass hard and fast. He held Jack off the ground as he impaled his skinny little boy body. Jack felt as if he were being torn in two. 

Coach Beatty kept thrusting into Jack until he finally blasted his load into the boy’s abused ass. He pulled his cock out and just dropped Jack to the floor. He was wiped out from the anal assault he had just experienced. Lyle gave him a slight kick.

“Oh no, you’re not done yet. You need to clean this tool off before I put it away.”

Jack looked back up at Lyle’s gigantic rod, still hard and covered in the shit, cum and blood from his poor violated ass. He wasn’t completely disgusted at this prospect of having to taste the slop on his defiler’s cock, but he knew he’d never get that thing into his mouth.

“I-I-I d-don’t th-think I c-can,” Jack said weakly.

“Yeah, you’re not getting this in your mouth, but you’ve got a tongue. Get to work.”

Jack knew he had no choice. He got up on his knees and began to lap at the dirty cock in front of him. His disgust soon gave way to desire, as he tasted himself, feeling all that was on Lyle’s cock on his tongue. He was soon grabbing onto his cock and licking and slurping his way through this chore and beyond. Lyle didn’t make him stop once he had clearly done the job. He enjoyed this cock worship too much. As Jack enjoyed Coach Beatty’s monster, Lyle felt another load of cum brewing. He pulled Jack away by his hair and blasted him with another thick load of cum all over his face and chest. Jack was coated in the Coach’s juices.

Lyle pulled his pants back up and ordered Jack to get up and get out of the shed.

“But, I---“

“I don’t care. Figure it out outside. I need to lock up and go. Get the fuck out of here!”

Jack stumbled out of the shed, naked, covered in cum and carrying his clothes. Coach Beatty locked the door and wandered off, leaving Jack there to fend for himself. The remote location of the shed worked to Jack’s advantage. Jack was so horned up from his sexual assault that he sat on the ground, still naked, and jerked himself to his own completion. As night fell, he just sat there and thought about what he’d just done. He did nothing to wipe the cum away from his face and hair, or anywhere on him. He put his clothes on, walked home and snuck in the house. As he lay in bed, still covered in dried up cum, he felt very right. He knew this is who he was. He wanted more.

***

Between work and sex, Jack had little time for friendships. He did socialize and had friends, but he kept his distance. He avoided getting too close to anyone, despite a longing to.

Jack had a pretty insatiable sexual appetite. When he wasn’t working, he was looking to get laid, or getting laid. It both worried and surprised him that his kinky, promiscuous sex life had never been discovered by anyone he worked with, though he pushed the envelope many times.

In addition to a steady stream of hookups, Jack had several regular fuck buddies, which made things a little easier during busy work periods. There was Jamie, the little college boy who liked to get fucked; Gregory, who was kind of a hipster dude that was into using Jack’s ass; Scott who was constantly trying to convince Jack to settle down with him, but also was a great, kinky fuck; and Ryan the former porn boy who was into fisting, to name a few. 

One of his worst experiences was a drifter named Shandy. This boy could have ended it all for Jack, and he came very close. The abuse Shandy put Jack through would come to be things Jack would enjoy under different circumstances, but with Shandy, it was dangerous. Fortunately, after a terrible beating that put Jack in the emergency room, Shandy disappeared. 

There was another boy that could have made life difficult for Jack, a sweet young kid named Jason. On the surface, it was one of the nicer things to happen to Jack in his life to that point, but ultimately, being with Jason was a career ending decision - if he got caught – which he almost did. 

***

One of Jack’s first big breaks was to be the campaign manager for a mayoral campaign in Waukesha, a major city just outside of Milwaukee. It was a successful effort to elect the first female mayor. Jack’s success here helped launch much of his career, eventually leading to him doing this kind of work full time. 

This is how Jack met Jason, a dorky looking, adorable, underage boy with almost jet-black hair and an illuminating smile that made Jack melt. Jason was thin, a little shorter than Jack, with slight hands and a quiet demeanor. He had piercing green eyes. Jason was quickly obsessed with Jack and Jack became completely infatuated with Jason. They developed a friendship during the campaign and spent a lot of time together. Jason had expressed great interest in his mother’s campaign and even said he wanted to get into politics. Because of those interests, Jason’s mother was more than happy to allow him to shadow Jack throughout the campaign. 

There was one problem, aside from being his client’s son in a relatively high-profile campaign, Jason was only 15 – a full 8 years younger than Jack at the time and most definitely against the law. Even the suggestion that something went on between them would get Jack fired and probably end his career before it started. Plus, while he trusted the boy, what if he was being set up? What if Jason meant to do harm or blackmail Jack? Doing anything with Jason would be completely irresponsible. As usual, Jack couldn’t help himself.

Eventually, Jack and Jason couldn’t resist themselves and they hooked up. It was late after a campaign fundraiser and Jason stayed behind to help tally the checks they collected. After they were done, Jack was supposed to drive Jason home. They had been working together for nearly two months, constantly flirting with each other. Once they finished their work, Jason asked if they could take a walk before heading home. 

“I really love being around you, Jack.”

“I feel the same way about you. You’re a great distraction from the stresses of the campaign.”

“Aww, that’s good. You work so hard. I’m learning a lot from you. My mom thinks you’re amazing.” Jason stopped, put his hand on Jack’s shoulder and said, “I think you’re amazing too, Jack.”

It was getting harder and harder for Jack to not make a move on the boy, and he tried hard to resist doing anything. “Thanks, Jason. You’re pretty fucking awesome yourself. So incredibly fucking awesome.” Jack started to walk, but Jason had other plans.

As they walked down the side street next to the campaign headquarters, they were walking past a construction site for a new office building. “Follow me, Jack!” Jason said as he grabbed Jack’s hand and pulled him onto the site. He hopped over a barrier and started to run towards the shell of the building. “Come on, Jack!”

“Jason! Where they fuck are you going?” Jack said with exasperation just before he ran after him. He went into the building and didn’t see Jason. “Hey! Jason? Where are you?”

“Up here, Jack!”

Jack looked up and there was Jason, standing on the second floor. “For fuck’s sake, kid, don’t fucking fall! How the fuck did you get up there?” Jason pointed to a ladder and Jack reluctantly climbed up. “Alright, mister, what has gotten into you? This is crazy. We could get hurt up here!”

Jason had moved to more solid ground, into the doorway of a half constructed room. He leaned against the doorframe and just smiled. Jack slowly walked over, knowing full well what had gotten into Jason. He was finally standing face to face with him. Jason put one hand on Jack’s waist and took his hand with the other. Jack brushed Jason’s hair from his face. He knew he should say something adult and make this stop, but Jack wasn’t exactly known for his will power. 

“I can’t hold it in anymore, Jack. I really like you and I really want to kiss you.”

“Ugh. I like you too, Jason. Buuuut…you know this is a bad idea.”

“I know. Can’t we just kiss once? No one will see us here. Then we can forget about it. I promise. Please, Jack? I want you to be my first kiss.”

That was enough to break Jack. Jason wanted him to be his first kiss. How could he say no to that? Jason stared at Jack with his eyes full of desire and flashed his sweet smile. He pulled Jack closer to him. Once they were nose to nose, Jack whispered, “this is so bad…such a bad idea…” Then, they kissed. 

The kiss was brief, merely a sign of the strong bond that had grown between the two. In the faint moonlight that managed to peek through the beams and gaps in the walls of the unfinished building, they stood there silently gazing at each other. Jason felt a stirring of emotion from his head to his heart. The touch of Jack's finger on his neck sent waves of pleasure throughout his body. His hands found their way around Jack's back, pulling him even closer, as if they were dancing together. Despite the precariousness of the situation, they both felt secure. No words were exchanged. The intensity of the young boy's emotions was more than he could bear; it was like his heart was about to burst out from his chest.

Jack placed soft kisses on Jason's neck, as Jason leaned back letting Jack bite him lightly. Jason whispered for Jack to continue. “Ooooh, this is so nice, Jack…” he said as he briefly pulled away and looked at Jack. In that moment of his first kiss, his first romantic encounter, Jason saw in Jack's eyes a feeling of protection, patience, and love. For the first time, he was feeling what it was like to be in love. Jack ran his fingers through Jason's hair, bringing his face close so they could kiss even more. Jason didn’t want Jack to ever let go. 

As their lips connected once more, Jack felt a surge as young Jason kissed him with an even deeper intensity. Nothing else mattered at that moment - no worries or fears of consequences if anyone discovered them. All that existed was the escalating heat between them and the passion of their kiss. It was a moment that Jason would never forget, a moment that would remain imprinted in his memory long after it ended. This was nothing Jack would ever forget either. 

The intensity of their kiss soon turned to something more as their hands explored each other's bodies, touching and caressing. Clothes were discarded on the ground in a passionate haste as they began to push themselves further than either had planned. They simply couldn't control themselves.

“We really should stop this right now…” Jack panted. 

“Yeah, we should…” Jason gasped in response while their hands explored every inch of each other’s body.

Soon they were both naked, wearing only their shoes, feeling the night air on their sweaty bodies. Jack kissed the sweet boy's body lower and lower until he was staring at his beautiful eight inch cock. Jack easily guided Jason's cock into his mouth and began to suck it with fervor. A moan escaped from Jason, experiencing these feelings of gratification for the first time, completely lost in sensations of pleasure building up inside him.

After a while, Jason took charge of the situation, pulling Jack up, kissing him again and then turning him around. Jack grabbed on to the steel beam in front of him, arching his back just slightly, effectively giving himself over to the boy. Jason had never fucked anyone before and took his time grinding against Jack's body, feeling Jack's hole with his fingers, feeling his precum drenched cock slide between Jack’s legs. He knew enough to spit in his hands and slick his cock up. Jack let out a soft moan as Jason entered him slowly at first, letting Jack adjust and getting his own composure, before finally burying himself deep inside this man he desired so much. For his first time, Jason was surprisingly skilled, fucking Jack with a rhythm and passion that would have been delivered by a more experienced top. 

"Oh my God, Jack! This is amazing! I am feeling so many things!"

"Yes, Jason, yes...you are amazing...don't stop...please..."

Jason kept going as long as he could, but it wasn’t long until he had to release. "Jack! Can I cum in your ass?"

"Yes! Go for it! I'm ready to blow...I can't wait anymore..." Jack said breathlessly as he shot his load all over the beam he was holding onto. As he climaxed, his hole tightened up around Jason's boy cock and caused him to explode, filling Jack's ass with a huge load of virgin boy seed.

Afterwards, they silently stood there, holding each other. The area around them too dirty to do anything else. They were lost for words about what just happened between them, knowing very well that people would react badly if someone found out. They knew no one would understand why it felt so good despite the danger it posed. It should have been wrong yet wasn't because of how good they felt in each other’s arms. Jack realized they were pushing their luck as far as getting Jason home.

“We really need to go.”

“Yeah, I know Jack. Just a minute more.”

“How about two?”

Amazingly, Jason’s mother didn’t inquire about the lateness of Jason’s arrival home. The success of her fundraiser had her in such a good mood, she didn’t care. In the subsequent days, Jack and Jason found time to be with each other as much as possible. They kissed, fucked, and then explored some more. In fact, they fucked a lot, way more than they should have. 

Jack so enjoyed being with Jason that he risked a lot to keep a relationship going with him. They figured out ways to see each other constantly, surprisingly, without drawing suspicion. He found himself addicted to sex with this boy and had urges for him nonstop. He loved getting fucked by a boy so young. Jason was very sexually aware for a kid his age, and he wanted to try everything. He wanted to do things that he shouldn’t have even known about at 15. Jack savored every bit of Jason. 

Things continued well after his mother’s successful election. From the time they met, to the time it ended, it went on for almost two years. Then they were almost caught. There was a boy in school who liked Jason. He kept asking Jason to go out with him, or even just hang out with him. Jason was always too busy - usually saving his free time for Jack. The boy was persistent, and a little obsessive. He started to ask him too many questions and was paying way too much attention to Jason. He started to spy on Jason, wanting to know why he was always so busy. One day, he confronted Jason about the older guy he was hanging out with. He insisted Jason tell him what was going on, or he would tell someone. With some guidance from Jack, Jason worked things out with the boy. He needed a summer job and wanted to work for the Mayor. Jack took care of that and the boy backed off. 

WIth this boy still knowing something was up, it made both Jack and Jason nervous. Jason didn’t want to hurt his mother in any way and Jack didn’t want to ruin his budding career. Since the mayor’s race, Jack had been getting more offers for political work. They knew things had to end. It was the more mature Jason who formally ended things. Jack still couldn’t bring himself to do it. Even though Jack knew this was inevitable, he was still devastated. 

Jack was amazed it could last so long without anyone finding out. Despite the potential for disaster, the whole experience was one Jack cherished. Jason was a first love for Jack, and he hated giving him up. Jason saw Jack’s vulnerability and told him it was best if they didn’t contact each other ever again. This sent Jack into one of his many spirals into bad behaviors.

***

The Playground, the club that Jack gave to Brayden and Jarrin, was doing very well. One of the reasons was the arrangement that they had with Samuel, the drug dealer. Samuel was managing all of the illegal aspects of the club, but that was more of a silent partnership. He also managed security for the club, ensuring that the police were kept happy. All of the arrangements with Samuel were somewhat precarious and could unravel at any minute. Jack kept tabs on things just to be sure there wasn’t any trouble. Drugs and prostitution were flowing very nicely at the Playground and all seemed to be working well.

Jack got a call one day from Brayden. He sounded upset.

“Wait, hold on. Calm down and tell me what is going on.”

“Jack, it’s Samuel. He’s pissed about something. He’s been texting me constantly asking where you are. When he was onsite on Saturday, he was very aloof. He’s never like that. The boys tried to get with him and he blew them all off. He’s always down for fucking the boys.”

“Have any of his goons been around?”

“No, at least nothing out of the ordinary. It’s just him being all passive aggressive and shit. You need to go talk to him. Things are going so well, Jack. We don’t need any fucking trouble. He obviously trusts you.”

“Ok, I will take care of it. Chill out. I’m sure whatever it is can be fixed.”

Jack hung up with Brayden and immediately called Samuel.

“Hey mister. Sorry we haven’t talked in a while. Brayden said you wanted to talk to me?”

“Oh, well. The very important Mr. Jack Holden finally has time for a lowly little crime boss like me.”

“Seriously? What the fuck is that about?”

“I know, you’re doing so many wonderful things. You like to ignore the special operation we agreed to. You just leave it to your minions.”

“Ok, I have no idea what this shit is about. Do we need to meet? What do I need to fix? You already get all the money from everything you do at the club and we pay you really fucking well for the security contract.”

“Jack. There is something important you need to know. Yes, we need to meet. It is absolutely fucking urgent. I’m tired of you ignoring my messages and texts.”

“I don’t think I have, but you do you. Tell me where to be and when.”

“You should drop whatever you’re doing and just get the fuck over here right now. My place. I don’t want to embarrass you in public.”

“Fuck. What is his problem? He’s never been such a jerk. Something must seriously be wrong. I hope this doesn’t cause fucking problems. I don’t need Justin saying I told you so.” Jack said to himself as he rode over to Samuel’s place. “I wonder what he’s up to making me come to his apartment instead of his office.”

Samuel buzzed Jack up and stood at the door waiting for him. Jack didn’t have to even knock, Samuel heard him coming and opened the door. Once inside, Jack noticed the apartment was lit dimly and he could smell Samuel’s incense burning. “Now I know what he’s up to.” Jack thought. 

“Hello, ass slut.”

“Did you just make up a bunch of bullshit - cruelly making Brayden crazy - just so you could shove your arm up my ass? A simple text would have been fine.”

Samuel was completely naked aside from wearing a leather harness and his long, black latex gloves, one on each arm. His cock was bound up with a leather strap around the base and his balls and a tight leather pouch to contain it all. He looked really fucking hot. He stepped close to Jack and shoved his hand in his pants, sliding a finger down his crack. “Aww, did my little prank upset you and your boys? Sorry. I was just having some fun. I haven’t had a nice, well used, talented cunt like yours in a long time. It’s been almost six months since I’ve been in your ass!”

“Jesus Samuel. Brayden was completely losing his shit.”

“Good thing he has his little pig slave to clean it up for him.”

“I need to calm down a minute before you do anything. Can I get a drink?”

“I was already prepared. Your scotch awaits you by the bed. So do a few new accessories I bought.”

Samuel had been watching videos of extreme ass play online and saw some things he thought were interesting. One of them was a stainless steel anal dilator that would expand up to six inches! Another was an unusual chastity device. 

“Look at you with the new toys.”

“I can’t wait to use them on you, especially that dilator thing. It looks fucking wicked!”

“Are you in a hurry? I know you like to get to business right away.”

“If you have time to chill first, I’m up for it. You’re usually the one rushing to your little boys.”

“I told my boys I have business with you and would be home late. They can fuck each other until I get home. I’m not spending the night, though.”

“I think you should plan to stay next time. I’d love to wake up to your ass.”

“Is it me or my ass that you’re in love with?”

“I’m not in love with you, but I do like you and would enjoy spending more time with you.” Samuel suddenly blushed a little and got all shy. “I know I’m supposed to be the tough crime boss, but when I’m around you I feel different, and it’s not because I love fisting you. I like when we kiss and cuddle too.”

“What the fuck is in the air anymore?” Jack snapped. It seemed like everyone he hooked up with liked him. Not that he wanted people to dislike him, but he just found it all frustrating.

“Sorry. I didn’t mean to upset you. Get naked so I can use your ass and you can go.”

“Samuel, I’m sorry. That’s not what I meant. I actually like you too. Can we just talk a bit before we get into it? I just need to talk about some things.”

“Sure, but you still need to get naked and I want you to wear the collar and the chastity thing.” 

The chastity device Samuel bought for Jack was something Jack had heard of but had never seen, let alone used. It had a steel ring to go around your cock and balls and a thin piece of metal that screwed onto the ring. Attached to the piece of metal was a steel bar that was about an inch and a half long, with a steel ball that was slightly larger than a marble attached to it. The unusual device would push Jack’s cock deep inside his body and lock it in place. There would be no way Jack could cum or even pee with this thing on. Jack winced a little and tried very hard to not get an erection as Samuel put it on him.

“For fucks’ sake, Jack! Think about naked Trump or something!” That was definitely enough to make both of them lose their erections.

Eventually, Samuel got the device on. “This is really fucking hot! It’s like your dick is gone!” Samuel said excitedly as he rubbed his hands over Jack’s bulging balls. 

“It feels kinda weird. Like, I can feel my cock inside me, but I can’t do anything with it. I think I might want to use this again.” 

They laid back on the bed with their scotches and Jack vented about how he was feeling. He shared how frustrated he was that for most of his life he was with shitty guys and he purposely sought them out. Plenty of guys wanted to have sex with Jack, not all of them abusive. There was something about Jack that basically oozed sexual energy. However, finding someone who genuinely liked him was tougher. There were a few like Jason and Nicholas, and Justin sort of, but until he met Harrison he was just a fuckboy to most guys. Over the last couple of years, since Harrison became a major part of his life, almost all of the guys he’s hooked up with have said they liked him, or more. They all said they would be with him. They all wanted to date him. It wasn’t that people liking him was a problem, he just found it incredibly frustrating that it was all happening at once.

“I can see how that would suck. Sorry, Jack. Hey, it’s not the worst fucking problem to have though. I wouldn’t mind a hot boyfriend like you.”

“I appreciate it, Samuel. It would have been nice to actually be able to date you. I already have two serious boys in my life - which makes me so fucking happy. I just wish we’d met at another time.”

“I’m sure you wouldn’t want to date me when I was fucking six. Anyway, if it makes you feel any better, I don’t want to fucking marry you. I just kinda like you. Now can I get my fist up your ass?”

Jack knew the drill and crawled onto the bed and into Samuel’s favorite position. He bent over at the edge of the bed, his ass raised up and spread open. As he pulled his knees up under himself and rested his head on the pillow Samuel provided, he felt something at his ankles.

“Another toy?”

“Yeah. I forgot to mention the spreader bar. I want to keep your legs spread as wide as possible. Maybe make it hurt a little?”

“I’m all yours at this point. You do whatever you want.

“Just another fucking reason why you’re the best fisting bottom ever.”

With Jack at the perfect height for Samuel to stand there and do his business, he enthusiastically dove right in. Jack flinched a little as Samuel’s slicked up glove pushed right into his ass with no warning. Samuel knew Jack’s ass could handle a full fist right off the bat. He forced each hand in, back and forth, aggressively kicking off the session. 

As Samuel punched his fists in and out rapidly, Jack shifted, leaning further down on the bed. Samuel’s hands sliding in and out would feel like a violent intrusion for most, but for Jack, it was sheer pleasure. His staccato breathing nearly matched Samuel’s thrusts. The sensations of a good fisting, aggressive or not, are sensations he thrives on. Samuel was particularly good at bringing them out. Jack had no sense of wanting him to stop or even ease up, he simply arched up and pushed back onto his fist so he could feel more. 

Samuel eased up a bit so he could more carefully explore Jack’s ass. He took his fingers and ran them around the rim, adding more lube as he did. He then added his other hand and pulled Jack’s hole wide open. 

“Fuck yeah. Jack, your hole is something special. I love how easy it is to play with.” Samuel said as he just worked his fingers in and out and then all around Jack’s loose hole. “I think I want to try this dilator thing.”

The stainless steel dilator had a large ring with six rods with smooth balls on the ends that went into Jack’s hole. They were attached to screws that extend the rods to stretch his hole wide open. Samuel carefully extended the rods enough so they’d stretch a little going in, then once he had the device in, he screwed two rods at a time, opening Jack’s hole even wider. He did this until all six rods were extended to their maximum - a full six inches. Jack’s hole was completely wide open, his insides were clearly visible. Samuel was awed at the sight.

“Holy fucking shit, Jack! I can’t believe how amazing this is. I’m gonna take a picture so you can see it. Fuck! I can stick my hand in your hole like I’m reaching into a bucket! Wow!”

Samuel snapped a few pictures and then proceeded to ease his hand into Jack’s ass and slide it around, feeling the walls of Jack’s rectum. Jack moaned softly as Samuel gently massaged the inside of Jack’s ass. “I wonder if I’ll see your dick poking back at me!” He played with Jack’s ass like this for a while, even pushing his hand into him through the second ring. He didn’t want to do too much, he was afraid he’d hurt Jack. He slowly removed the ring and gave Jack a little break. He and Jack had some water and a little more scotch before Samuel continued. 

Once again, Samuel’s probing fingers slid into Jack’s hungry hole and manipulated their way deeper inside. Samuel started slowly and eventually gained speed as he pushed his hand deeper and deeper into Jack. After he got to his elbow with one arm, he would switch to the other. He kept up this alternating action for a while, fist fucking Jack hard and deep. Each time he’d pull his arm out all the way and then punch it back in. 

“Fucking hell, Jack! I love your ass!”

After working each hand individually, Samuel started to push them both in. At first he would go in with one and then add the other. This went on until Samuel was ready to really push things. He clasped his hands together and stood behind Jack, aiming his double fist right at Jack’s hole. With just the slightest resistance, Samuel pushed his double fist and then both of his arms into Jack’s ass. He pushed as far as he could go, almost to his elbows. Jack wailed his approval. Samuel pulled out and pushed back in again. He double fisted Jack as fast and as deep as he could.

Samuel stepped back after a while to check on how Jack was doing. Even though he knew the answer, he felt he had to ask. “Are you doing ok, ass slut?”

“Fuck yes, I am. Don’t stop now!”

“That’s what I wanted to hear!” Soon, Jack felt Samuel’s arm reaching deep into his gut, past the wrist, then the elbow and soon passing over his bicep. Samuel had gotten his entire arm into Jack, all the way to his shoulder. As he held his arm deep inside Jack’s cavernous ass, he shivered with delight.

"Goddamn!" Samuel exclaimed, “you're fucking taking it all, fuck yeah Jack!!!” Samuel twisted and turned his arm for a bit and then pulled it all the way out. He repeated the action with his other arm, pushing it in until it had completely disappeared, forcing Jack to feel the full length of his powerful arms over and over. 

“You've got my entire fucking arms all the way inside you. Fuck!! I still can’t believe I can do this!" Samuel was so excited at how much Jack could take. This was his dream to completely work an ass over with basically no limits. 

"Awwwwww…more…uuuuuhhhhhhnnnnnnggggggg…aaaahhhhhhhh…” Jack murmured incoherently, “mmmmmore…give me more...."

“God damn, Jack! I can’t make my arms any longer! I wish I could fuck you with both at the same time!” 

Samuel began to slowly pull his arm out until only his hand remained. Jack feared he was going to take it out, but instead, he merely lubed it up more and then thrust his arm back in very deeply and slowly. Again, he pulled out almost all the way and then pushed back, this time a little harder and faster. Samuel kept repeating the motion over and over, picking up speed, plunging the bulk of his forearm deeply in and out. Jack was groaning and moaning as loudly as he could.

"This is just so fucking hot!" he groaned. "Your cave of an ass is a fucking fantasy turned real. How are you feeling, Holden?” 

Jack was panting like a puppy in heat, “uhhhhhh…yyyyyessssss…”

“I know what you’re ready for now,” Samuel lubed up his fists and arms and added more to Jack’s gaping ass. He wound up and swung his full fist landing in Jack’s hole and thrusting it almost up to his elbow. Jack let out a euphoric scream as he pushed back to take Samuel’s anal assault even harder. 

Samuel was manic. He punch fisted Jack’s ass with every bit of ferocity and strength he could muster up. Jack was in his own state of bliss. Samuel was a master fister and was able to use Jack’s ass like no one else. The boy’s obsession with fisting made him a true aficionado. After working Jack’s ass like this on and off for 30 minutes, Samuel eased up, gave Jack a break and then went for a more sensual effort. This was the longest session the two of them had to date at more than three hours. 

When it was all over, Samuel fucked Jack, jerking his cock while it was in Jack’s ass. After he blasted his load deep into Jack’s gut. They laid there, completely exhausted.

“Ok…I can’t fucking move. I need my phone. I’m texting the boys. You get your wish. I’m not going anywhere.”

“Aww, Jack. We get to cuddle all night.”

“Cuddling is all we’re doing. I don’t think I will survive even five more minutes of your madness. I love it, but I need to rest. I need…to…”

Jack fell asleep. Samuel kissed him, grabbed his phone and just before he curled up behind him and spooned him, he texted Harrison and Aidan. 

Hey! its Samuel. I think I fisted Jack into oblivion. He's sound asleep. He will call you tomorrow.

Of course, after sleeping for a couple of hours, neither of them could resist another fisting session, the second of three that would happen before Jack finally left.

***

Thanks to Jack’s wealth, philanthropy, and political power, celebrity encounters with people other than politicians weren't that unusual. Jack has met dozens of famous people at benefits and parties. He’s also been pulled into financing projects for some. There were also encounters that were just simply that, random encounters. 

Most of Jack’s random encounters were one-offs, or maybe a repeat situation. He had violent encounters with Cole Sprouse, Chris Brown and Christian Slater. Of course none of them upset Jack since getting beat up was something he enjoyed. He had plenty of random fun with hotties like Harry Styles, Timothee Chalamet, Tom Holland and Chandler Riggs. In fact, several of Jack’s celebrity hook ups came back for more. Just because they were famous and usually had to hide or find secret meeting places, didn’t mean they were immune to the charms of Jack Holden. Timothee Chalamet keeps in regular contact with Jack and tries to connect whenever they are in the same city. Chandler Riggs texts Jack frequently looking to get together. Just like the regular boys, famous boys usually want another taste of Jack. 

Through the efforts of others, Jack has become sort of a go-to to help finance projects in movies and music. His finance guy Max also does a lot of work in the entertainment industry and he’s gotten Jack involved in projects with Justin Bieber, Machine Gun Kelly, Finn Wolfhard and Nicholas Hoult. Sometimes, Jack has no idea he’s an investor in something. 

The most recent celebrity hook up was with the kid from Stranger Things. Finn Wolfhard actually came to Jack through Bon, Wagner’s husband. One of Bon’s brothers is involved in a film project and is looking for funds to support a short film by Finn that would be his directorial debut. Bon brought the idea to Wagner and since he rarely asks for anything, Wagner thought it was significant enough and brought the idea to Jack who immediately said yes. Jack had no idea it was the kid from Stranger Things until he went to meet the team in Vancouver, offering up one of his hotels for them to stay during shooting. Finn took notice of Jack and was too shy to approach him, thinking he was too young for him. He said something to Bon who laughed and said he was the perfect age for Jack. Bon made the connection. Jack and Finn hooked up several times. 

Jack and Finn had a relatively calm night for their first hook up. Finn was nervous and wasn’t sure if he could get away with the kind of fun he wanted to have with Jack. It was the next day that he revealed his interest in fisting. He’d never done it before, but really wanted to. Jack stayed another day just to spend another night with him. It turned out to be a really fun night for both of them. Finn got to learn how to fist someone and once he did, he was hooked. He’s wanted to reconnect with Jack a few times, but Jack’s life with Harrison and Aidan, along with his other responsibilities keeps him too busy.

Jack became close with Justin Bieber thanks to an early investment opportunity that Max came up with through a colleague. Through a fairly convoluted connection, Jack befriends Scooter Braun and ends up a major silent backer of hip hop music and several major stars, including Justin Bieber. Being who he is, Jack took special interest in Bieber. On his own, Bieber pursued Jack and invited him to spend a weekend with him. Bieber's interests are sexual, but he knows it would hurt his career to come out as bi. He and Jack developed a hushed, secret sexual relationship that ultimately ended as Bieber became more popular and he married Haley. If they get the chance, they still hook up, Justin sees to that. To many people's surprise, Bieber is an aggressive top and loves to plow Jack with his eight and a half inch cock. Bieber loves to get fucked too, which Aidan happily takes care of after a benefit one night. Jack and Bieber keep in touch regularly.

Thanks to Max, Jack was also a silent funder of Bad Boy Records. Max arranged for everything and one of the projects Sean Combs wanted Jack to fund was Machine Gun Kelly. One look at Kelly, also known as Colson Baker, and Jack said yes. He told Max it didn’t matter if he could sing, he just wanted to see him. This would be the big break Kelly needed and Jack helped make it happen. As it turned out, Jack really liked Kelly’s music and remains supportive of his career. 

Many people don’t realize that MGK is sexually fluid. When he met Jack, he was smitten. He didn’t even know Jack was one of his backers when he asked someone to introduce him.

“Who is the suit?” MGK asked Max’s assistant.

“That guy there? That is Jack Holden. He’s a businessman and stuff.”

“He looks the part. Introduce me to him.”

“Really? You want to meet him?”

“Is that a problem?”

“No, Mr. Baker. Just let me get Max.”

Max’s assistant dashed off and sent Max over. “So, you want to meet Jack Holden, eh?”

“Yeah. He seems interesting.”

“Ha. Yeah, he’s interesting alright. Come on.”

“Hey, Jack, I want you to meet someone. This is Colson Baker, otherwise known as Machine Gun Kelly.”

“Oh, wow, it’s a pleasure to meet you. I’m a fan.”

“You’re a fan of my music? You don’t look like the type.”

“Colson, this is Jack Holden. He’s someone you definitely should get to know. I’ll leave you guys.” Max smirked at Jack as he walked away. He knew Jack was all about MGK. What he didn’t count on was MGK being into Jack.

“I guess I didn’t know there was a type. Honestly, it’s not the kind of music I usually listen to. But, I like it.”

“Nice. I’m, uh, curious about you. I dig the pink.” MGK commented about Jack’s tie.

“Oh? I like pink. It’s a fun color. What are you curious about?”

“I’m curious if tall skinny tattooed boys are something you like.”

“Gee, let me think on that a second,” Jack looked MGK over. He was wearing a tight sleeveless shirt, a few chains around his neck with random medallions, and a pair of tight jeans with tears and holes in them. “Maybe. I generally like tall skinny tattooed boys with skulls painted on his nails.”

Baker looked down at his nails, as usual they were painted, and they happened to have skulls on them. “Looks like we have a winner.”

Jack and Colson talked for a while. It was evident to the people who knew both of them best that they were hitting it off. Eventually, Max would let Colson know that Jack was the backer of his record. He wanted to wait until they were well into their conversation to see just how well they got along. When Jack mentioned that he was going to Baker’s hotel room, Max knew he’d struck gold.

The sex between Jack and Baker was pretty wild. Colson was a pretty aggressive top who liked how much attention Jack paid to every part of his body. Baker’s over 11 inch cock made Jack happy, especially as he got pounded by the pop star. MGK railed Jack good and hard for most of the night. Jack took a pounding in his throat too. Baker couldn’t believe how much fun he was having with Jack. 

“Damn, man! You are gonna wear me the fuck out! I’ve never been with someone who can take it like you. Fuck!”

“The more you give, the more I will take.”

“Yeah, fucking hell! I got a lot more to give to you.” MGK slid his right arm through his left hand in a fisting motion, “like this man. I definitely want to give you this.”

“Then I guess we will be seeing each other again soon?”

“You fuckin’ know it!”

***

Despite a complicated and messy life, Jack was also more successful than almost anyone. That didn’t mean he was ever happy. For most of his life, he was quite miserable. Just like when he was a boy, he was exceptionally good at hiding it. 

Now, things were different. Jack could finally say he was happy - he could even say it out loud. He followed through on his commitment to Harrison to get help and was seeing a therapist - something he had never done in his life. In just a few sessions, the therapist realized Jack had more things to process than his entire roster of patients combined.

Telling Joshua off like he did flipped a switch in him. Not only did it make him realize he wasn’t pathetic or worthless, it also made him think about his legacy. He wondered what he’d leave behind. He wanted it to be something good. When he realized how badly Joshua had beaten him down, he was shocked he was successful at all.

Jack had more money than anyone could imagine. One of the things about that much money is it constantly grows. His businesses were all hugely successful. He just kept making more and more money. Of course, he knew this was not the worst problem to have, but it still bothered him. Even with all the good he did, he knew he wasn’t doing enough. He was going to make some major changes. He began consulting with Wagner and Max about how he could do more. Jack was ready to retire and enjoy life, something he thought he would never be able to do.

Nearly losing Harrison reminded Jack that time is fleeting. He had the most amazing boy in the world in his arms every day. He wanted to be with Harrison as much as he could. Harrison still hadn’t seen the country, let alone the world. There were tons of experiences they could have together. He didn’t want to waste time working too hard and feeling depressed.

Aidan complicated things for Jack. Falling as deeply in love with another boy, as he had with Aidan, shouldn’t have been possible. Harrison and Aidan worked out together, even though Jack knew they each wanted him to themselves. It was their love for Jack that allowed them to make their odd relationship work. It was yet another unusual thing in Jack’s life that would almost ruin any other relationship. And while most people lose their sex drive when they get older, Jack’s just got stronger. He had two hot, virile boys who couldn’t get enough of him. He never felt younger.

Jack’s friendship with Blaze really took off. He saw himself in Blaze and wanted to do all he could to help him succeed. He was never interested in kids, but treasured this father-son like relationship. They worked through their depression together. Jack completely gave of himself to Blaze and was ready to pass his firm on to him. It was especially gratifying that the firm he built would continue and thrive after he was gone.

Seeing Calista grow into what she had become gave Jack such joy. With the weight of Joshua lifted off of him, he was able to see that. He loved her dearly and wanted everything for her. He was committed to making sure she got everything she wanted. Hearing her story impacted him a lot, knowing what she had been through. Harrison struggled, Blaze struggled even more, but they were still strong enough to make it, even if they had to do it alone. Calista would never have made it this far on her own. Lucas was too weak and without coming into his life, Jack worried we’d never have met Calista.

Jack had no problem welcoming Brayden and Jarrin into his world. They had their own rough lives and Jack felt they deserved better. He knew they weren’t there to hurt Harrison, they were just manipulated by Joshua. It was in his nature to help these boys out. They wouldn’t be the last either. Jack was already doing a lot, almost exclusively anonymously. He was preparing to do a lot more for several other people in and out of his orbit. 

This was the legacy that Jack was going to leave behind. Helping a whole bunch of deserving people - especially Harrison, Aidan, Blaze and Calista - get where they deserve in life.