The Kinksters are Alright

Chapter 26

Impetuous 

Boys - and girls - were very attracted to the beautiful young woman Calista had become. Free of Justin, and fully involved with Kwang, Calista felt her confidence grow stronger than ever. She was proud of her body, her boyfriend, and most especially her work. Calista was getting top grades in school, her clothing line was taking off, her costumes for Broadway getting her noticed. She was making a statement in the community and was becoming a respected philanthropist. Calista was on fire. 

All of this newfound popularity and confidence also meant that Calista grew apart from the people she had in her previous life. She made little effort to keep Harrison or Aidan in her life. She also didn’t really keep in touch with Justin either. She occasionally talked to Blaze. She still talked to Jack, though not as much as she used to. Calista still felt strongly about Jack and that she still needed him in her life. 

Calista had so many new friends. Everyone wanted to be friends with her and she took full advantage of that. She had friends from all aspects of her life and was always busy. Her and Kwang were regulars all over town. Kwang was always at her side, she was extremely proud to have him on her arm. Kwang was beyond supportive and loyal. When the Tony Award nominations came out, Calista was nominated for her costume work. She and her friends were out on the town celebrating this amazing milestone. 

When the night came to a close, Calista and Kwang invited some friends over for a little after party. It was a chilly night, but they decided to walk home from the bar where they were celebrating. They made their way through the city looking like a force to be reckoned with. It wasn’t unusual to have to dodge homeless people, which was fairly routine in the city. Calista hated to see homeless people, given her own experience. She would often give money, food or clothes to them. She donated tons of money to local shelters. She would even get hotel rooms for people on cold or rainy nights. They didn’t run into many folks that night.

As they were about to pass a doorway to an empty building, they could see that someone was tucked in there under a bunch of blankets. Calista was already feeling bad. She reached into her purse and pulled out some cash. For the moment, at such a late hour, it was really all she could do. 

“Here, sorry this is all I can do right now. If I see you again, I’ll get you some food.” Calista hesitated as her friends started to walk away, she saw a 24 hour pizza shop across the street. “Wait a minute, I can make sure you get some food. Kwang, can you dash over to that pizza place and get him something?” Kwang loved Calista’s devotion to helping people on the street. He ran off to go get food. “You girls go ahead. I’ll text the doorman and tell him to let you in, okay?”

Her friends didn’t love the idea of her staying there with some random homeless guy. They also knew there was no way they were going to change her mind either. “Just be careful girl!” Her friend Katya shouted back. They did appreciate her endless desire to help people.

The guy under the blankets kept himself buried and didn’t really look up. “This is really nice of you, thanks.” Calista thought his voice was familiar. Kwang was still waiting on the food. She knelt down to get a little closer. 

“Have I helped you before? You sound familiar. You’re all buried under your blankets, so I can’t really tell.”

“I don’t know missy, maybe. Thanks for the food though. I am really hungry.”

Missy. When Calista heard him call her that, something clicked. It was what Alex called her the night he raped her. He repeated it so many times that it is burned into her memory. “Missy is a cute name for someone.” Kwang arrived with a pizza and some sodas and set them down on the ground.

“Yeah, so? Why don’t you just leave me alone? I don’t know what you want. Thanks for the cash and the food, missy.”

The guy sounded sad and dejected. He was definitely one of the homeless that was legitimately down on his luck. Hearing the word missy clicked in Calista’s head. The voice was so familiar. “Ok, Kwang, let’s go. We shouldn’t bother him.” She couldn’t shake the thought from her head. It was Alex. She would never forget the way he called her that. She stopped Kwang.

“Kwang, would you think it was weird if I told you I think I know who that is?”

“Maybe a little, Miss Calista, but you are always full of the surprise.”

“He just sounded so familiar.” A wave of emotions went through her. Anger at what he did to her. Sadness for seeing him like that. 

“You do want to go back to him to find out, don’t you?”

“Please, will you come with me? I will be completely distracted all night if I don’t find out. He probably won’t be there in the morning. The cops will move him along soon enough. Maybe I’m just imagining things.”

“Ok, but please, let us be careful, ok?”

“Yes, always. We could take him if we had to.”

They walked back to where the homeless guy was. They stood back for a moment and then approached him. He didn’t look up. He wasn’t expecting them to return. He heard footsteps and just assumed he was getting booted from his spot.

“Ok, I’ll get going. Give me a minute.”

“No, that’s not why we’re here…um…Alex?”

The guy didn’t move. The three of them were silent for what seemed like an eternity. He finally looked up. Calista looked very different than she did the night he raped her. He had no idea it was her. It was obvious to Calista who he was once she saw his face.  

“How the fuck do you know my name?”

“You raped me.”

Kwang cringed at Calista’s directness.

“Missy, I don’t even know you.” Alex slunk down into his pile of filthy blankets..

“No, really, you raped me. You were awful to me. I know you’re Alex. You lived in a giant mansion in Wisconsin and that is where you raped me. You were one of Jack’s abusive boyfriends. I remember you well.”

Alex didn’t move. He just sat there. Kwang wasn’t sure what to do or what would happen next. He worried that this could go badly very quickly. He stepped back and dialed 911 on his phone, ready to call at any moment. Calista knelt down and brushed Alex’s hair from his face. Alex quietly sobbed.

Calista put her hand on Alex’s chin. “Hey. Look at me. I want to help you.”

“Calista? Why? I was awful to you. I’m a piece of shit. I should be dead. Why would you help me?”

“Because, no one should live like this.” Calista was taken aback at how beat up Alex was. He still had blood on his face from some altercation. His eye was swollen.

“I deserve this. Just leave me. You weren’t the only person I fucked over. Jack was right to throw me away like fucking trash.”

“No, you need to get those cuts cleaned up and you need to get warm and you need food. Please, just come with me.”

Kwang was moved by Calista’s kindness. He knew the story of what Alex did to her. He hoped he could do the same if he ever had a situation like this. Most people would just leave him there to suffer for what he had done. Calista had other plans.

“Miss Calista, may I speak to you?”

“I’ll be right back. Gather your things.” She told Alex.

“Are you sure this idea is good? He could be…” Kwang struggled to find the right words, “broken? What if he is still bad? He raped you, Miss Calista.”

“I know this seems crazy, but I can’t just leave him like this. He’s in bad shape and needs help. If he tries something, we’ll deal with it. Please, you know I can’t just leave him like this? I know it is the right thing to do.”

“Can we not bringing him into the apartment?”

“We’re not. We will put him in the empty loft next to us. It has furniture and everything. You know, where we put up those trans kids. We’re going to bring him there. We will be safe, and once we get him settled, he will be safe.”

Kwang let out a big sigh. “Ok. If it is wrong, I'll call the police.”

“Ok, Alex, let’s go.” Calista reached out her hand to help him up.

“Are you sure? You don’t have to do this. I’m where I belong.”

“No, you are not where you belong. I will not leave you alone until you come with me. Alex, this is not what you deserve, no matter how awful you were to me. Now, stand up and walk with us. Do it, Alex.”

Alex was surprised by Calista’s tone. He stood up slowly. He used the walls around him for stability. He winced in pain as he tried to straighten himself out. Whatever altercation he had really messed him up. He stuffed what he could in the big IKEA shopping bag he had. He just left the rest, hoping it would still be there tomorrow. It really wasn’t much.  He followed Calista and Kwang to her building.

Once they arrived, Calista had to convince the doorman everything was going to be ok. Kwang ran ahead to get the keys to the loft. He explained to their waiting friends what was going on. “She’s fucking Mother Theresa,” one of them said. 

She walked Alex into the fancy loft. “You should just make yourself at home. Go take a shower or a bath, whatever. There’s some food still in the freezer. Eat as much as you want. There are clothes in the bedroom. I’m sure you’ll find something that fits you.” Calista grabbed Alex by his shoulders, “I expect to find you here in the morning. I’m going to take care of you, though I might require something in return. Or you could steal my stuff and leave. It’s up to you, Alex. I’m going to find the good in you.” 

Alex just cried. “I don’t know why you are bothering, but thank you. I’ll be here in the morning. I’m really sorry I did what I did to you.”

“We’re not going to talk about it now. I have a party to get to. Just make yourself comfortable. I’ll get you to a doctor tomorrow too.”

“I don’t deserve this.”

“I’ll decide what you deserve. Good night, Alex.”

As Calista went back to her apartment, she texted Jack.

I know it’s late, but I had to tell someone. I found Alex and I’m helping him.

***

Even though it seemed that Jack had sex with pretty much everyone in his universe, staff of his various companies were usually off limits. This was especially true of his drivers. They were a select group of employees chosen because they could be trusted with anything, including the random things that go on in Jack’s world - and sometimes the things that go in the car. They were like Jack’s own private Secret Service. Jack has never fraternized with the drivers in all the years he’s had them. There were definitely some hotties that he would have, but he always felt that is one of the places where things could get very complicated and make things difficult for his team. 

Cameron was shaping up to be an exception. It was obvious the boy was nervous around him. That was either because of who Jack was or something more. Maybe both. 

On the ride over to the hotel, Jack made a quick call to his office to confirm everything about Cameron. He really had no reason to worry, but this was an unusual circumstance since Cameron was regularly available to drive him around. Tonya was one of Jack’s sharpest employees and she was usually very on top of things.

“Oh, Mr. Holden, I am so sorry. With Mr. Archambault and the extra new folks in town, I assigned some of your drivers to them. We all thought Cameron was a good fit for you. Is he not?”

“I’m sure he’ll be great. It was just the first time I didn’t know anything about my driver.”

“That is my fault, Mr. Holden. I apologize. He came to us for a job, to wash cars, and was so eager. He even asked if he could have the copy of the Financial Times we had in the lobby because it had an article about you in it. I thought he was being wasted in the garage, so I sent him on a test drive. He did really well for a first timer. I gave him a confusing set of routes and he completed it better than some of our more seasoned drivers! He did ask about being able to drive for you. When you didn’t say anything the first time, I figured it was ok. We checked him out like we do everyone. Terrible credit score, but otherwise clean. I hope I didn’t mess up.”

“No worries, Tonya. I trust you implicitly. If anyone can pick the good ones, it is you. I’ll let you know how he does.”

Once they arrived at the hotel, Jack asked Cameron to wait for him. He needed about 15 minutes to let them know he was there and he would head off to a meeting. That would give the hotel staff time to prepare for Jack being there, since it was a surprise. He chatted with some staff and then needed to use the bathroom. As Jack took care of his business, someone came into the bathroom. They dropped a plastic shopping bag on the floor and turned on the sink. The bathrooms were still getting their finishing touches, so the stall doors weren’t quite a perfect fit yet. Jack could peek through and see who was there. It was Cameron. He was brushing his teeth. He then washed his face and quickly changed his shirt after putting on some deodorant. It seemed odd that someone just starting their shift would need to freshen up this way. And why the plastic bag stuffed with clothes? Something was off here. Jack waited for him to leave before finishing things up himself.

When Jack stepped outside, Cameron was chatting with one of the bell staff. Jack noticed his suit was a little wrinkled and his shoes were a bit worn out. Once he saw Jack, Cameron quickly leapt into service and opened the door. 

As they drove over to the Hill, stuck in terrible traffic, Jack moved to one of the seats in the middle and lowered the divider. “Hey Cameron, how are you doing? How are you enjoying the new job?”

Surprised to be engaging with Jack, he responded nervously, “oh, uh, I’m ok. H-How about you, Mr. Holden. Oh! I mean, Jack. I, um, love this job.”

Jack already knew the answers to his questions, but he wanted to see how Cameron reacted. “So, how is it that you’ve been assigned to me so much? I usually have multiple drivers.”

“Oh, um,” Cameron seemed embarrassed, “I, uh, asked to be? I wanted to meet you and I asked if I could be on call for you. I’m sorry if that was wrong. They said you wouldn’t mind.”

“Not wrong, per se, and I don’t mind, but I’m curious, when was your last shift?”

Cameron felt like he was caught. “It was…um…three days ago. I worked my other job last night. I was there until 3:30 am.”

“And you picked me up at 7:00am? You couldn’t possibly have gotten much sleep.” 

“I’m ok, really. I just needed the hours. Sorry.” Cameron held up a can of Red Bull. “This helps a lot.”

“Can I ask where you live?”

“Um, Baltimore.”

“Jesus, kid, that’s an hour away! Did you stay with a friend, I hope?”

Cameron was saved by the proverbial bell, they arrived at the meeting location. “Yeah, uh, we’re here, Mr. Holde.” He didn’t feel comfortable addressing him as Jack since he felt like he was in trouble.

“We’re not done here, mister.” Jack pulled a business card from his wallet. He wrote a note on the back. He gave Cameron a handful of twenties as well. “I’m surprised we didn’t give you a pair of shoes with your uniform, so head over to Brooks Brothers on Connecticut. Ask for Mr. Doyle. He will get you a new pair of shoes and hook you up with some other stuff. Maybe even a nice duffel to use instead of a plastic bag.” Cameron went pale, he knew Jack had seen him in the bathroom. “Grab some breakfast too. You look hungry. I’ll see you in two hours.”

Jack was so busy for the rest of the day, he didn’t have time to grill Cameron any further. He didn't forget though and spent a lot of time wondering what this kid's deal was. It was pretty late, normally another driver would have taken over so no one was working too long of a shift. Jack called in to dispatch and told them that he wanted to keep Cameron on until the next day. Jack got into the car after the last meeting and offered to take Cameron to dinner.

“I’m not in the mood to eat with Sen. Schumer tonight. God, he’s not fun to be around at all. I don’t even like him. Anyway, would you be willing to join me?”

“Really? You w-want to have d-d-dinner with m-me instead of a Senator? Is th-that even o-o-ok? I didn’t think that w-w-was allowed. I’d lov…um, maybe not? I should go home, I think. I’m supposed to drive you around tomorrow too.”

“It’s ok. I can do whatever the fuck I want. It’s my company. I would definitely rather have dinner with you than him. Being from Baltimore you probably know about The Prime Rib, let’s head over there. I’ll call and tell them we’re on the way.”

“I-I-I am s-sorry ab-b-bout the stutter. It h-h-happens especially w-w-wh-when I’m n-n-nervous.”

“You have nothing to worry about. You don’t have to be nervous, though I do find it adorable.”

Jack took Cameron to an old school steakhouse that was a favorite. Cameron seemed surprised that Jack would bring him to such a fancy place. Everyone at the restaurant knew Jack and immediately brought him a drink. He got a drink for Cameron and ordered for both of them. They sat in a booth toward the back and talked through dinner. 

Cameron shared that he lived in a small house in one of the older parts of Baltimore with his dad and his sister. His mom had recently died after a long illness and things were tough for them. The 24 year old was doing all he could to help his dad out with the ridiculous debt the family incurred from taking care of his mom. He was working four different jobs, usually at least two of them in a day. The kid was very earnest and just wanted to help his family out. He also had a sort of crush on Jack, which became more and more obvious as the dinner went on. He had read about Jack in a newspaper he found on the train one night almost two years ago. The more he learned about Jack, the more he knew he had to meet him. 

Cameron also had an ulterior motive, which is why he wanted to work at Jack’s company. He needed to meet Jack, endear himself to him in some way and then ask for help. From what he’d read, Jack Holden was a very generous man. Now that he’d met Jack, he felt bad and that he was just taking advantage of him. He still shared his story, but never actually asked for anything. What he didn’t realize is that Jack had Wagner look into him and already knew most of the story. He already decided to help him out long before he heard it from Cameron himself. 

The next day’s meetings were late in the day so Jack could tour the new hotel. During dinner, he texted one of the staff to tell them to prepare a room for Cameron.

“Since you need to be here tomorrow morning, I’m guessing you’re going to stay at that friend’s place again tonight?” Jack had brought everything full circle to the conversation earlier in the day.

“Um, no.” Cameron blushed and looked down. “I, um…slept in the car…at the, uh…garage. I know that is against the rules, but I needed to sleep! I’m so sorry. I was never going to get home and back in time to pick you up. I-I-I…”

Cameron was clearly embarrassed and felt like he’d really messed up. He hoped this wouldn’t mean he’d be fired. He liked this job, with or without Jack. Though being around Jack made it much better.

Jack put his hand on Cameron’s arm and tried to calm him down. He was practically in tears at this point. “Hey. Don’t worry about it. You’re fine. The fact that someone your age is sacrificing so much to help his family is just fucking awesome. You’re doing all you can. Probably too much. Stop worrying. Your job here is safe.”

“Thank you, Jack. You are so kind. Like really fucking kind. I am sorry to be so stupid.”

By this point, Cameron’s desire for Jack was oozing from him. Jack was struggling internally with what to do. He didn’t want to break his own rules, and he didn’t want to think the boy had to do something in order for Jack to help him out. Jack was never good at resisting his urges, though he really was trying this time.

“How would you like to sleep in a hotel room that no one else has been in yet?”

“What? You mean at the new place?”

“Yes. I had them prepare a room for you. I don’t want you trekking all the way back to Baltimore only to come back again in the morning. I definitely don’t want you sleeping in the fucking car. Is this going to be ok with your dad?”

“Oh, uh, yeah. He’s used to me not coming home. I don’t have a change of uniform though. I also have a shift at the bar.”

“Don’t worry. I’ll have the office send over a clean uniform, you have your new shoes, and whatever Mr. Doyle hooked you up with. We can get anything else you need tomorrow. Call the bar and tell them something. You were in a car accident, you’re ok, but you need to take a few days off.”

When they stood up to leave, Cameron couldn’t contain himself. He grabbed Jack and gave him the biggest bear hug he could muster up, crying in the process.

***

Alex wasn’t sure what to expect with Calista. “Why is she being so nice to me? Why is she bothering to help me?” He was definitely happy to be in a warm, dry, comfy bed and to have had a shower. He enjoyed some of the food he found in the freezer and had a few beers that he found in the fridge. He began to worry. “Fuck. What if she is planning to fuck me over? What if she plans to have me arrested?” Alex panicked. He thought about leaving. He went back to bed and figured he’d see what she was like in the morning.

Calista wrapped up her party and was sitting with Kwang on the couch. “What will you do to the man in the loft? Do you really want to do something for him?”

“I do, Kwang, I really do. Doesn’t everyone deserve a second chance? He fucked up big time, but maybe he’s not so bad. Maybe his life sucked too. I will give him a chance to show me he’s a good guy. If he fucks it up, he’ll be back on the streets.” Calista stared off into space for a few minutes and sighed. “There is something, though. But I don’t want to upset you.”

‘What Miss Calista? How can you upset me? I have commitment to you. What are you thinking?”

“I kinda want to get a little revenge. Nothing awful. I don’t want to hurt him or anything. Well, I don’t want to hurt him too much. He fucked me up for a while, Kwang. I want to help him, but I think he has to understand what he did to me. Probably a bunch of others too. Do you think I’m wrong?”

“Oh no, Miss Calista. I think you are right. We can do it to him what he did to you.”

“Exactly! So, you’re in this with me? I promise I don’t want to be really mean, but I want him to feel what I felt.” Kwang nodded in agreement. “Ok. Let’s do this right now. I want you to get the big black dildo that we like and the big blue one that looks like a screw. We’ll need rope too.” Kwang ran off to gather everything. When he did, they went to the loft. Alex was asleep, but woke up when he heard them enter.

“Oh, uh, hey. What’s up?” Alex said groggily.

Calista motioned for Kwang to stay in the living area while she went into the bedroom. “I wanted to come and see you.” Calista sat on the bed and brushed her hand across his cheek. “I have plans for you, Alex.”

Alex looked scared. Calista hadn’t made anyone this nervous since the politician she abused. “Please don’t hurt me. I’ll do anything for you, but please, I’ve been hurt enough.”

“Aww, poor baby. I don’t want to hurt you, at least not the way you might think.”

“What are you going to do to me? Please don’t have me arrested. Calista, just tell me what you want. I said I was sorry. What else do I have to do?”

“Do you remember how mean you were to me? Do you remember the horrible things you said to me?” Calista leaned in close to Alex’s face, one hand in his hair, the other making its way down his torso. Her tone changed, it was now a dark whisper. “You call me ugly. Said I was worthless, useless, disgusting.” Her fingers were now tracing outlines around his mouth. Her other hand was dangerously close to his cock. “You said I was a freak. The worst was when you said I shouldn’t exist. You know, those words make people kill themselves.”

“Calista, I was an asshole. I was probably on something. I didn’t mean those things.”

“You didn’t? I think you did. Well, back then you did. You don’t feel that way now, right?” Calista lifted herself up and grabbed his cock. She squeezed it in her hand. “You don’t think I’m a freak now do you?”

Alex winced at her grabbing his manhood. “No! No! I don’t think you are a freak. You are fucking beautiful! I was wrong. I’m so fucking sorry.” Alex started to cry. “I did bad things. I’m not like that now. Please. I promise. I will make it up to you. Just tell me what to do. Please don’t hurt me, Calista. Please…”

“I love how desperate you sound. Do you realize that you sound like I did that night?”

“Just do what you have to. I can’t go back out there. Please just make it quick.”

“I just want you to feel what I did. I’m going to do to you what you did to me. Of course, it won’t be rape because you know you need me to do this. Right?” Alex nods. “Exactly. I guess I could have made this harder on you, but I’m not like that. Just consider this revenge. Once I do this, we won’t discuss what happened ever again. I want you to stay with me. I want to give you a chance to change for the better. Are you up for that?”

“Yes, please…thank you Calista. I promise I will not disappoint you.” Alex wiped away some of his tears and sniffled, “you are gonna hurt me, aren’t you?”

“I am. You’ll be fine. I survived what you did, you’ll survive what I do.” Calista stands up and steps back. “Come on, let’s do this.”

Alex nervously followed Calista into the living room. She motioned for him to stand by the dining room table. Kwang had pulled the chairs away and went to the other side of the table. Calista had filled him in on her plans. “Remember when you tied me to the table?”

“Yeah…” Alex said anxiously.

“Good, then you know what to do.” Alex leaned over the table and put his hands behind his back. Kwang tied his hands together with a rough, uncomfortable rope. He tied his legs to the table legs, spreading him out uncomfortably. “You look good like this, Alex.” Calista smirked.

Calista spit on her hand and rubbed Alex’s hole. She shoved her long, slim fingers forcefully into his hole causing Alex to yelp. Calista slipped off her skirt and exposed her cock. She spit some more on her cock and shoved it mercilessly into Alex’s ass and began pounding him roughly. The abrupt opening of Alex’s hole sent a sharp pain through him. He was not used to being fucked at all and the hard thrusting of her cock was uncomfortable. He looked up and realized he could see himself in the window, much like he made her look in the mirror. Kwang stood by watching.

“Kwang and I are going to destroy this hole.” Calista shouted as she started to build up a rhythm, fucking Alex as viciously as he could. “I forgot to tell you, this is going to go a bit longer than when you did me.” Alex was afraid of what Calista was going to do, thinking this would have been all of the abuse he had to take. 

Calista pulled her cock from Alex’s ass, went around to his mouth, pulled his head up by his hair and shoved her cock deep into his throat. While she brutally fucked Alex’s face, Kwang started fucking his ass. Alex gagged, spitting up gunk. Calista and Kwang worked Alex over for several more minutes before they moved on to the next part.

“We’re not done yet, sweetheart,” Calista snarled when she and Kwang pulled out of him. She picked up the big, black dildo and held it in front of his face. It was a massive dildo by most standards, about 15 inches long and two inches thick. "Oh, I just can't wait to fuck you with this."

“Oh fuck no! You can’t do that to me! Calista, please!! No!! That's too big! It's going to hurt me," Alex cried out as he looked into her eyes with actual fear.

"I know, just like your big cock hurt me.” Calista said as she held the dildo out for Kwang to pour lube on. 

"No, I'm serious, please, Calista…that won't fit.” Alex was getting very nervous. “Kwang! Help me!”

“Kwang isn’t going to help you. I may have him fuck your throat so I don’t have to listen to you.” Calista stroked the huge dildo, “Yeah, boy… I’m going to rape your ass now,” She said to him in a mocking sweet voice, “I’m going to shove this big, thick cock up your ass and fuck you until I get bored.”

Alex was in tears. “Fine. Just get it over with, please.” 

Calista pushed the head of the dildo against his tight hole and then began to push forward slowly, but steadily and firmly. Alex began to cry out, but she continued to pressure. "Oh yeah, boy, give me that tight little ass. I'm going to fuck your brains out and yeah, it's going to hurt, oh yes Alex, it is going to hurt. No matter how much it hurts you, I'm going to keep fucking you. I'm going to fuck you over and over. I'm going to fuck you until you can take that even bigger dildo." Kwang held the larger, thicker dildo in front of Alex’s face. 

“Oh GOD NO!! PLEASE!! NO!! That is way too fucking big!”

“Aww… you‘re a scared little rapist, aren’t you… a frightened little boy afraid it’s going to hurt… well, you should be scared… because I’m going to make sure it hurts… I’m going to use you like you used me and probably a bunch of others. When they screamed out for you to stop, did you? I‘m gonna turn your ass into a gaping fuckhole, you‘ll never be the same.”

The dildo was more than halfway in, all Alex could do was grunt and moan. Calista was finally fucking Alex’s ass with abandon. He just howled in pain, but that didn’t stop her. Each time she withdrew the giant dildo almost entirely out of his tight sphincter, she rammed it all right back in. Calista punished him for a while like this and then told Kwang to lube up the other monster, a huge blue dildo that was around 12 inches long, but much thicker, close to three inches thick.

“Go on Kwang, you fuck him now. I want to see his face. Then I want to cum all over it.”

Kwang rammed the huge blue dildo into Alex’s ass, making him scream bloody murder. While Kwang was wrecking Alex’s hole, Calista was fucking his throat. She was relentless as she pounded away at him working to bring herself to orgasm. As she got closer, she wanted Kwang to cum too so she told him to toss the dildo and just fuck Alex. After a few more minutes, both her and Kwang blasted their loads. Calista made Alex swallow her load, Kwang pumped his into Alex’s gut.   

Calista patted Alex on the head and repeated his words back to him, “I might like having you around, little pussy boy.”

Alex could barely lift his head. He had cum dripping from his sore mouth, his throat throbbing. His ass was even more sore and felt like it had been ripped apart. He was so uncomfortable bent over the table, the ropes scraping his skin. He couldn’t believe that Calista was able to take him like that. He was exhausted and just laid there hoping to be freed soon. Kwang carefully removed the ropes.

“Thank you, Alex. I needed that. You were amazing! I hope we can play like that again. Now, come on, Kwang will draw you a nice hot bath so I can take care of you. No more pain, ok? I’m going to make you feel good now.”

“That’s it, right? You’re not gonna do that to me again? Please…”

“Not unless you want me to. That’s how consent works, my dear.”

“Message heard. Loud and fucking clear.”

***

Once at the hotel, they went to their rooms. They ended up in two adjoining rooms. After saying goodnight in the hall, they went into their respective rooms. Cameron was blown away at how beautiful the room was and the view of the city. He’d never been in such a luxurious place. He went and plopped himself on the bed. It was heavenly. After calling off from work and then calling his dad to let him know he was ok, he stripped down and took a long shower. Even the towels were awe inspiring to him. The rooms weren’t all fully set up for guests, but the staff left toiletries and a robe behind. They also left sodas, water and even some wine in the room as well. Cameron poured some wine and tried to relax. It was just after 10 pm. Cameron was almost never able to end his day this early. 

Jack called Harrison for his usual nightly chat with him. After Jack filled him in on things with Cameron, he was convinced Jack would not be obeying his company rule. Jack poured some scotch for himself and cued up the music videos one of his young celebrity friends, Finn Wolfhard, had sent him, and kicked back for the night. He was pleased with himself for not breaking his rule. Never one to sleep well, especially alone, Jack would probably sit there all night, most likely texting with Harrison since he wasn’t out fucking or getting fucked. He was just chilling at home with Aidan, watching movies. This pleased Jack since it meant they had patched things up. Of course, he knew they wouldn’t just be sitting around cuddling for long.

It was about two hours after they settled in. Cameron was sitting in his room, finishing off the last of the wine, totally anxious about what was happening. All he could think of was Jack in the next room and how much he wanted to be laying next to him. “This is my chance. I can’t fuck this up. I’ll never get this close to him. Damn, he’s so cute! I want to just kiss him all over. Ugh. I want to just fuck him so much. I have never wanted to fuck someone so much!” Cameron thought to himself. “Oh fuck it. I gotta do this. This is my chance to finally do this!”

Unsure of his next move, Cameron paced the floor. He held his phone in his hand wondering if he should text Jack or if he should just knock on the door between their rooms. He decided to knock. Jack was startled by the knock at first, forgetting that someone was in the next room momentarily. He was stroking himself to Harrison’s filthy texts and watching Wolfhard’s videos, imagining a threesome with the two of them. He closed up his robe and went to the door.

“Hey, Jack. I’m…uh… r-r-really sorry to…um, bother y-you.” Cameron stood in the doorway, also dressed in the robe he found in the room.

“It’s ok, Cameron. Is everything ok?”

“Yeah. Sorry…I’m just… gonna go back…”

“Come in. It’s ok. You should come in.”

Cameron hesitated, then slowly stepped into Jack’s room. He stood right in front of Jack and looked at him earnestly. Neither of them said a word, they just stood there in silence, Jack still holding the door in his hand. Cameron lifted his hand and brushed Jack’s hair back. “We’re not s-s-supposed to do…this…right?” He said as he edged just a little closer.

“Um, technically, no. But, I am the boss, so…”

“So I can…um… k-k-kiss you? You won’t…uh, f-f-ire me?”

“That’s not a fireable offense to me.”

Still standing there in silence, Cameron’s face slowly turns red. They’re now standing very close together in the doorway. His hand shakes as it lightly grazes Jack’s. He feels warm and blushes, keeping his gaze on Jack. Slowly Jack grasps his hand, lacing their fingers in a way that makes Cameron’s heart beat faster. It feels weird to Cameron. He’s an employee and now he’s spending time alone with Jack. Intimately. 

A smile nervously crosses Jack’s lips, because he knows he shouldn’t be with this boy, his driver, his employee, alone in his room. It’s too late to do anything about it now. They both stare, Cameron in awe of Jack, Jack adoringly. Their fingers are entwined, their bodies close. Jack shifts a little closer and their noses touch. They both let out a soft giggle. Jack’s breath is on Cameron’s lips, and he quivers a bit at the sensation. Cameron’s heart is beating so fast that he can barely breathe.

Ready to finally start this journey with this cute boy, Jack presses his lips to Cameron’s. Usually, Cameron would close his eyes for a kiss, but he kept them a little bit open, he needed to see Jack as he kissed him. The kiss is slow and sweet. Jack gently moves his hand under Cameron’s loosely tied robe, over to his hip, and lays it there, rubbing the smooth, exposed skin there. At the moment, it’s not sexual, but comforting. Cameron lifts his hand and slides it into Jack’s robe, pressing against his chest. Not too hard, so Jack doesn’t think he’s pushing him back. This slow and passionate kiss goes on for a long period of time with Cameron lost in it.

After what seems like an eternity they pull away, lips slightly sticking together, just a bit. Cameron’s face still red with excitement and maybe a little embarrassment.

“Wow. Th-Th-That was…um, so much better…better than I thought it would…b-b-be. And I thought…it would be…so good.”

“That was really nice. I had no doubt it would be.”

“I-I-I should j-just…go now… before…”

“It looks like some parts of you want to stay.” Cameron’s eight and a half inch cock was standing at full mast, poking out of his robe.

He laughed nervously, “uh…yeah, um…”

Jack didn’t wait for an answer, he leaned in and kissed Cameron again, a little more ardently. He had both hands on Cameron’s hips, softly caressing them, pulling Cameron close. He could feel Cameron’s rod poking through into his robe and brushing against his legs. “You can stay if you want to.”

“I r-r-r-really want to s-stay, Jack.”

“I guess it's settled then.” 

Jack took Cameron’s hand and they walked over to the bed. They slipped their robes off and climbed onto the bed, making out fervently. It was passionate, but sweetly innocent. Cameron wasn’t like the other boys in Jack’s life. He was a soft touch, almost cautious. It was nothing like the heated passion Harrison gives him or the ferocity that Aidan forces onto him. Cameron was just a gentle boy whose nervousness made it all the more adorable. 

Cameron seems apprehensive, like he wants to do something, but isn’t sure he should. He stops kissing and looks down at Jack. He stroked his cheek ever so softly. Jack enjoyed the gentle, tender touch of the boy’s fingers and his affectionate smile looking down on him. Cameron is a well of emotions, he is stirred deep inside, thinking how amazing Jack is, how lucky he is to be with him. 

“Are you ok, Cameron?”

“I think so?” Cameron says as he looks at Jack quizzically. Jack smiles before pulling him down to kiss him deeply, keenly aware of how much this boy wants him, sensing his need for him. Something felt different about Cameron than other boys. They kissed some more, their tongues lashing against one another. Cameron pulled back just a bit and felt the tension build.

“Jack…I…I…um, I haven’t…” with a deep sigh of frustration, Cameron lifts himself up. He looks back down at Jack apprehensively, “Oh fuck it…I have never done this, Jack! Well, not much… and it wasn’t… good.”

“Oh, Cameron. I don’t care about that. You’re doing it now and you’re doing very well. Whatever you want to do. We don’t have to do anything. We can just cuddle if you wan—”

“No, Jack. I don’t want to cuddle.” Cameron’s firm conviction caught Jack off guard, “This is p-p-p-probably r-r-rude. I just r-really w-w-want to, you know… I want to be inside you. I just…have never done that. I’m not a virgin! I’ve just never been…a…a top. I’m sorry.” He leaned back with his hands over his face, then leaned down right over Jack’s face, his hands on either side of his head, “but you. You, Jack. I want to be a top for you. I don’t even know if you’re a bottom. Someone like you is probably such a top. Fuck. I don’t know what I’m doing.”

Without saying a word, Jack reached around Cameron’s neck and pulled him down. He kissed him again, this time even more fervently, but still slowly, dragging it out, savoring it. Jack is so used to the madly passionate fucking that he has with Harrison and Aidan, but he feels this needs to slow down, so Cameron can feel everything. “You know exactly what to do,” Jack whispers. 

Jack isn’t used to guiding things. He’s always just let boys take him. It has been a long time since he was with a boy like Cameron. He gently let his fingers explore Cameron’s body, feeling his soft skin down his slight patch of chest hair, past the curly hairs of his trail. He explores his way downward until his fingers are sliding through the crease where his thigh meets his torso. Waves of soft pleasure are flowing through Cameron’s body as Jack teases him, moving his fingers all over his crotch, without actually touching his balls or his cock. Cameron’s breathing quickened, sensing his need Jack reached down and caressed the soft, silky skin of his balls.

“Oh my God, Jack…”

Jack moved his hand upward, glancing at Cameron and seeing his eyes squeezed shut in longing for Jack to continue his exploration. Jack wraps his hand around his throbbing cock, feeling how hard he is. More familiar feelings rush over Jack, he needs this cock deep inside of him. He needs this boy to fuck him for all he’s worth. He needs to be stretched and filled and pounded, leaving a bit of himself inside him. 

Looking directly into Cameron’s eyes, Jack lightly strokes his rock hard member. He raises his legs and guides Cameron’s tool toward his waiting hole. Jack is about to help Cameron do something he has never done before. Cameron’s eyes widened, gasping deep breaths as he felt Jack take his cock firmly, and slide just the head in, squeezing it with his sphincter. “Ohhhhhh, ffffffffuuuuuuuccccckkkkkk!!!!” Cameron moans as Jack releases and slides his cock in another inch, squeezing again. Jack is surprising himself at his ability to direct this situation. He allows another inch, hearing Cameron’s breath quicken as his eyes squeeze shut, and he lurches back. Jack’s hole squeezes him again. Then, finally, he eases him the rest of the way. Once Cameron is firmly lodged inside, Jack waits, driven crazy by the feel of his hard, throbbing cock filling him. 

Cameron knows he has to take control. He remembers what his ex used to do that he loved, so he tried it with Jack. With his cock still deep inside, he moves his hips in little circles making his cock touch every bit of the walls of Jack’s ass. 

Cameron finally speaks, his voice intense, breathy, and very sexy. "How d-does that f-f-f-feel?”

Barely above a whisper, Jack replies, "It feels so good, Cameron. I love the way your cock feels inside me."

He pulls out a little, then firmly pushes in. "D-d-do y-you like th-that?"

“Uh huh.”

Taking his cue, now feeling like he can do this, he pulls back out, tenses up, and then slams roughly into Jack’s ass. Jack moans as he feels his boy cock plow into him, not fast, but firmly, decisively. Cameron is experiencing every thrust deeply. This moment is the most meaningful one he has had in a long time, if ever. Jack gasps as they settle into a rocking motion, Jack’s ass sliding back and forth on his raging hard cock, his cock answering with firm thrusts. He gets slightly quicker, slightly more intense, when he leans down and plants a ravaging kiss on Jack’s lips. Jack wraps his arms around Cameron’s back, digging his nails into his back as he slams into him more insistently.

“Oh my God, Jack! God damn!” Cameron screams as he slows down his thrusting. He feels his orgasm building and wants to do it slowly, feeling every pulse of his cock as it dumps his seed into Jack’s ass.

Sensing his pending climax, Jack nudges him along, needing to release himself, "I need you to cum inside me, Cameron."

Cameron slowly thrusts in a few more times, then looks straight into Jack’s eyes and whispers, "I'm about to cum…." Then he thrusts in and holds himself inside, looking into each other's eyes as they both shake violently, Jack’s hole squeezing and releasing uncontrollably as he cums, meeting each pulse of Cameron’s cock squeezing every last drop of cum out of him.

When it is over, they relax as Cameron falls on top of Jack, breathing into his shoulder, holding him close. “Jack, I l-l-ov—” before finishing his words, he catches himself. “I loved that!”

“Fuck, I almost said I love you. Fucking idiot!” he admonishes himself. 

“That was incredible, Cameron.”

They stay in a pile, Cameron on top of Jack with his soft cock still inside of him, as they drift off to sleep.

The next morning, they didn’t talk much about what happened. A shared slight smile was enough to acknowledge their satisfaction with one another. They took the tour of the hotel, Cameron blown away by the beauty of it, Jack pleased with how it all came out. They continued their day with Jack’s meetings. Jack still wanted to let Cameron know he was going to help him out. He invited him to stay another night.

“Will that be ok? I don’t want you to upset your dad.”

“He’s fine. I just told him I have a tough work schedule. He understands.”

“Pick a place for dinner and let me treat you again.”

“You’re too kind to me, Jack. If you don’t mind, I really liked the place you took me last night. Can we go back?”

“Totally. I would have gone there anyway if I were by myself.”

Throughout the day, Cameron was much more relaxed. He felt more confident and wasn’t nervous about being around Jack. In fact, he felt so confident, he asked to spend the night with Jack again.

“Since we already broke the company rule, can we do that again tonight?”

“You must be reading my mind. I was going to ask you to join me again tonight. That was fun. I think you’re lying about never topping before.”

“Seriously, Jack. I never have. I’ve only had a few experiences and my ex was a total top. I only had sex for the first time when I was 19. So…”

“Well, you are an excellent top. I’m happy to allow you some more experience so you can be even better.” 

“I appreciate that. I hope you’re not offended when I say your ass is, like, um, magical. I can’t believe how good that felt.”

“Wait until you get a chance to try my throat.”

“Mmmmm. Are you exclusively a bottom, because I would love for you to fuck me and let me suck you off too.”

“We can work all that out later. I have something I want to tell you.” Jack took Cameron’s hands and held them across the table. “You really got to me with your story about your family. I’m so sorry you went through all of that with your mom. She sounds like she was very special.” Cameron started to tear up. He was also wondering where Jack was going with this. “I’m going to get you in contact with my number one guy. My fixer. You have your dad give him all the information about the hospital bills and everything else. I want all the info on your mortgage, student loans, credit cards, everything. I don’t want your family to have to worry anymore.”

“Jack? What are you doing?” Cameron asked through tears.

“I’m making sure your family is taken care of. By the way, this isn’t optional. It’s not charity. It’s not pity. It’s just righting a wrong. I’ve got you covered if you want to go to school. I’ve got your sister covered for whatever she wants. I know you said your mom was the breadwinner of the family and your dad’s job doesn’t cover the bills. Well, first off, you won’t have any more bills and secondly, if he wants a better job, I probably have something in one of my businesses that he can do and enjoy while making good money. You can quit all of those other jobs. You can quit this one if you want, but I hope you’ll stay. You’re a part of something special now. I’ve got your back. You and your family will never have to worry about anything again. At least anything we have control over.”

Cameron was completely overwhelmed and just broke down crying. He couldn’t believe what was happening. When he started this he thought he’d get a loan or a raise or some help with the bills. He never expected this massive expression of generosity. Clearly he didn’t know everything about Jack Holden.

While Jack comforted Cameron in the booth, the manager of the restaurant was watching things with one of the service staff. “What’s going on?” the server asked.

“Just the usual. Jack Holden is just changing yet another person’s life.”