Unbelievable
About a week before Liam found Harrison being used as a hustler by a seedy drug dealer, Aidan had a run in with Harrison at the Chicago apartment. While Aidan had suspected something was wrong, he had no idea the degree to which Harrison had fallen.
Dillon and Jimmy certainly kept Aidan busy when it came to sex. Dillon wasn’t into anything rough, but Jimmy liked when Aidan would get rough with him. Of course, Aidan wasn’t always around Dillon and Jimmy and sometimes, actually all the time, he craved the kind of no holds barred anonymous sex he was used to before he got into a relationship. He promised Dillon he would visit the bath house less, but he still needed his fix. Aidan’s sex addiction was something he could never shake. Even his therapist gave up on it, focusing instead on his other issues. Aidan needed to fuck and he needed to fuck hard.
Since he wasn’t allowed to bring anyone home that wasn’t playing with him and Dillon together, Aidan would use the Chicago apartment for his exploits. It was hardly ever used since Jack was out of town so much and Harrison was off doing whatever he was doing. He occasionally used his dorm room, but the apartment was much nicer. When he showed up one day, the door was ajar and he heard noises coming from Jack’s bedroom. He approached slowly and saw in a mirror that it was Harrison.
“Boo!” Aidan shouted as he entered the room. Harrison flew off the ground about three feet. Aidan just laughed.
“What the fuck?!?! You scared the shit out of me!”
“Good thing you like eating shit then. What are you doing?”
“I’m looking for something! What the fuck is it to you?”
The room was a mess. Drawers were all open, clothes strewn about. He was digging through the closet for something. Harrison’s hands were shaking, he looked pretty bad. He was wearing his usual preppy wear, though the clothes definitely looked like he’d been wearing them for a while. His sweater was all ratty and one arm was hanging on with what looked like paper clips. His corduroys were stained and frayed. Nothing seemed to fit him well at all. It just hung there on his extremely skinny frame. When he finally looked back at him, Aidan could see his eyes dark and sunken, his skin really pale and his hair a mess. His glasses were filthy and broken, being held together by a bandaid.
Aidan walked into the room and got closer to Harrison. He smelled of smoke and sweat and was all clammy. Aidan put his hand on Harrison’s shoulder and he flinched away. “Hey, buddy, are you ok?”
“I’m fucking fine asshole. Get the fuck off me unless you plan to fuck me.” Harrison turned and looked at Aidan sort of lecherously. “You wanna fuck me? Fist me? Huh? You can rape me like you did that day. Make it really fucking hurt.”
“Harry… what is going on? You’re a fucking mess! Dude. Come one, let’s get you in the shower or something. You look like shit.”
“Fuck you. I look fine. Fuck off.” Harrison appeared frustrated, he let out a grumble and shook his fists. “Fuck. I don’t remember what the fuck I was even looking for. You fucking messed me up! Get the fuck away from me!” Harrison was on edge.
Aidan just stood there looking at his friend, still rummaging through the closet for something he couldn’t remember. He felt really sad. While Aidan and Harrison had some issues recently, he still loved him and this was breaking his heart. “Harrison, please. Let me help you. I can call Jack.”
“FUCK JACK! AND FUCK YOU!! You people don’t give a fuck about me!! All you fuckers did was give me shit about every fucking thing. FUCK YOU!!” Harrison went to swing at Aidan. He knocked himself off balance and almost fell over. Aidan grabbed his arm and pulled him up.
“God fucking damn it. You know what Harrison? You can fuck off. Look at what you’ve done to yourself. You’re a fucking junkie.” Aidan was angry, but couldn’t stop the tears from welling in his eyes. “Fuck, Harry. You’re throwing your life away. Jack is going to be fucking devastated. You’re gonna fucking kill him with this. Fuck. How did this fucking happen?” Aidan slowly stepped away. “Jesus. Get the fuck out of here. Whatever you are looking for isn’t here. Go back to your junkie friends.”
“They fucking care about me! They love me!!”
That was the last thing Aidan wanted to hear. He turned and stomped back toward Harrison. He stood inches away from him. His face was red with fury. He was firm, but calm in his response. “You know what? I fucking love you. You’re my fucking best friend. My fucking brother.” By now his tears flowed freely. Aidan wiped the snot from his nose. “Everybody fucking loves you. Jack. Jack loves you. Those assholes are using you. They are destroying you. Harry, wake the fuck up. They will sooner watch you die of an overdose than save you. They don’t care. They don’t love you.” He stood there crying. Harrison felt something, but was in such desperate need of a fix, he couldn’t express it. “You have ten seconds to get the fuck out of here or I will make sure you regret every decision you have ever made. Go!!”
Harrison hesitated a moment and then grabbed some clothes and walked out. Aidan watched as he stumbled out of the apartment, slouching over and dragging his feet. As he stepped onto the elevator, Aidan’s first trick was coming off. He looked back in disgust at the drugged out boy passing him. He walked into the apartment and saw Aidan sitting on the couch, a bottle of bourbon in front of him and a thick joint in his mouth.
“Dude, you ok? What the fuck was that? You fucking homeless dudes?”
“I fucked you when you were homeless, asshole. Just shut the fuck up. I am not in the mood for your fucking opinions on who I fuck. Just get fucking naked and on your god damn knees.”
The guy was a regular of Aidan’s. Ever since he fucked him behind the record store more than a year ago, he developed a strange sexual friendship with the guy. He was an older man named Zane who had fallen on hard times. Aidan ended up helping him out and they became friends. Zane loved a good, hard railing from Aidan and frequently sought it out. Seeing Aidan like he was, he knew something was wrong. He didn’t want to be nosy, but he felt like Aidan needed more than just a blow job at the moment.
“Aidan, seriously. You can tear me apart soon enough. You ok? You need to talk?”
Aidan sighed loudly and leaned back on the couch. He motioned for Zane to sit next to him. Once Zane sat down, Aidan handed him the blunt. “Thanks man. I do need to vent for a bit. I am in a fucking mood though, so be prepared for me to go full fucking beast on your ass.”
“That’s cool. That’s what I come to see you for.”
Aidan spent a few minutes giving a brief rundown on what was happening with Harrison and how it was affecting him as a friend. As he spoke, Zane listened without commentary. Instead he used the time to get naked and slid down to his knees to pleasure Aidan while he vented. Once Aidan was done talking, he was ready for what was really on the agenda.
“Thanks for listening, man. You ready to get fucking destroyed?”
“I’m all yours boss.”
Aidan grabbed Zane by his long, scraggly hair and threw him onto the couch. Zane was now exposed and vulnerable, his ass in the air. Aidan's rage was quickly coming on. His heart was pounding, he was sweating and his head felt cloudy. As always, Zane smelled of sweat, alcohol, and feverish desire, causing Aidan's blood to run hot. Something beyond being horny was driving Aidan. He felt like his old self again and he loved it.
After jumping off the couch, Aidan kicked Zane's legs apart and stepped between them. With a cruel smirk, Aidan forced his colossal, rock-hard cock inside him. He showed no mercy, whihc is exactly how Zane wanted it. With a satisfied grunt, he pushed further in until Zane screamed out at the sudden intense pain. "Uhhh...holy fffffuck!" His tight hole stretched beyond its limit as Aidan slammed into it with raw force. Tears pooled in Zane's eyes from the agony of the rough fucking, but Aidan only grew more vigorous with every thrust. “UNNNNGGGHHH! Fuck!” Zane cried out again. As Zane opened his mouth to scream, Aidan shoved his fingers in it, forcing them deep into his mouth.
Zane didn’t struggle anymore, this is what he wanted and he had become used to Aidan’s aggression. He let his body yield to the assault, an assault he willingly asked for. He began to contort himself, making it easier for Aidan to push himself further and further in. Even though it hurt, Zane was enjoying Aidan’s dominance over him. Aidan growled as he ravished the guy, pounding his ass with an angry force. "I'm going to fuck you so hard you will be feeling it for fucking days!" Aidan bellowed, his hand now stuffed into Zane's mouth and pulling on his face, his other hand holding his head back, pulling it sharply back. He kept relentlessly fucking Zane as hard as he could, as if punishing him for something.
Zane whimpered in pain and pleasure, unable to break free from Aidan's grip, not that he wanted to. Unbelievable to Zane, the intensity of Aidan's thrusts increased as he felt a blissful agony rushing through him. He never knew how long Aidan would keep pounding away at him, only that he could tell Aidan had pumped at least one load of cum in him already. Aidan continued this way for more than fifteen minutes before shooting another load inside him and still coming back for another.
Zane had already released, his cum splashed onto the couch. Aidan groaned and pushed himself in deep, keeping himself planted while he shot yet another load deep into Zane's gut. He stayed there like a dog knotting up with his mate.
By the time Aidan pulled out, neither of them could barely stand straight. Aidan staggered over and fell back onto the couch next to Zane. He grabbed the joint from the side table and lit it up again.
“Damn! You are such an amazing fuck. Damn dude.”
“That’s why you haven’t stopped coming for me for more than a year.”
There was plenty to distract Aidan for the day, but he still had Harrison on his mind. He was worried about him and wasn’t sure what to do next.
***
After meeting Isaiah, Harrison was hooked on him. He began staying at Isaiah’s drug house, essentially as his fucktoy. He lived in a small room with Tyler, the hustler who tried to steer him away. Isaiah had plans for Harrison, but he needed to make him fully dependent on him first. He made Harrison give him money that he got advanced from his credit cards and debit cards. Harrison was drawing out thousands of dollars a day and giving it to Isaiah. In return, Isaiah kept Harrison high, slowly increasing the doses every few days and then denying it from him, making him go into withdrawal. He hadn’t locked Harrison down yet, so he could still go out and wander around looking for sex. Soon though, Isaiah was planning to keep Harrison tucked away for his own personal benefit.
“Where have you been, pretty boy? You know I don’t like you disappearing like that. Am I going to need to restrain you?” Isaiah calmly growled at Harrison. He stopped him at the top of the stairs of the front porch, not letting him through, his henchman Quaid standing behind him.
“I went for some stuff. Clothes! See! I need more, Isaiah, please. I am out of my mind. Please.”
“You’ll get more when I say you get more. Did you bring me my money? Or were you too busy shopping?” Isaiah grabbed the clothes from Harrison, “well, you have some nice things here. Good thing you and I are almost the same size. I’ll enjoy these.” He handed them off to Quaid.
“Um, uh, no… I’m sorry. I forgot.”
Isaiah grabbed Harrison by his shoulder and forced his thumb into the space between his neck and collarbone. It felt like he was going to push right through his skin. It was extremely painful. “You know what our arrangement is, pretty boy. You get as much money as you can off those fancy credit cards and you bring it to me. And then I give you candy and make you feel good.” He forced Harrison to the ground. “Now, get the fuck out of here and go get me some cash. I have plans for you, pretty boy, don’t fuck things up.”
“Please Isaiah! I need to get fucked. But I really need something! Look! I’m shaking!! It hurts, Isaiah!!” Watching Harrison beg so desperately was entertaining to Isaiah. He loved nothing more than taking down a rich kid. “A little bump? Just one line? One shot? Please, Isaiah!! He loved seeing Harrison on his knees, but Isaiah had enough. He kicked Harrison in his chest, sending him off the porch and down the stairs.
Harrison wandered away, dejected and desperate. He needed a fix badly. He needed to get fucked badly. He was ready to do anything to feel high again.
In desperation, Harrison eventually figured out how to get to Raccoon’s. He had already alienated himself from Raccoon when he started hitting the harder drugs. Raccoon tried to pull him away, but he was too far gone. He felt terrible about it, blaming himself for letting Harrison use as much as he did. He thought the boy was in control. Raccoon had to stop seeing Harrison. He was putting him at risk and causing him problems with his business. He hated to do it, but he had to push Harrison away.
Then, he showed up at his door.
“Oh my god! Scooby! Get in here!! Fuck. What have you done?” Raccoon grabbed Harrison and hugged him. Harrison felt warm from the hug, he remembered how Raccoon was so good to him. But he wasn’t here for reconciliation. He needed a fix.
“Please Raccoon, I need to get high. I need the good stuff. Gimme that meth and coke and K and G. Give it all to me. Please, I fucking need it now!!”
“Jesus Harrison, calm down. I’m not giving you all of that. You need to get off this stuff. Let me help. Come on buddy, let me take care of you.”
Harrison tried seduction. “I’ll let you do whatever you want, baby. Fist me. Fuck me. Shove those big dildos in my ass. I’ll eat your shit, you like that, right? Please, I’ll do anything.”
Raccoon was trying hard not to show how emotional he was. He was devastated to see Harrison like this. The guilt was overwhelming him. He’d seen lots of boys crash and burn, but he didn’t love them, he didn’t care about them. “Look, Scooby. Just hang out for a while. Let’s talk. I’ll give you something later. Yeah, we can fool around. It will be fun. Just come sit down. Chill, buddy. I’ll get you some tea.”
Harrison wasn’t having it. He punched Raccoon in his stomach and then shoved him away. He pushed so hard that Raccoon fell into a table and a lamp fell on him. He was disoriented just long enough for Harrison to rush the cabinet where a lot of the drugs were stored. Harrison grabbed anything he could and ran through the kitchen and out the side door. Raccoon finally got up and chased him, but he couldn’t keep up. Harrison was gone. Raccoon fell to the ground in tears. He feared the worst. His sweet little party boy was just another junkie.
***
“Jack, this is Raccoon. I know we haven’t talked in a while. Um…”
Raccoon called Jack and got his voicemail. He was still broken up about Harrison and he was having trouble speaking without getting emotional. “Uhhhh… Fuck. Jack, you… I just saw Harrison. It’s… really… it’s really… bad.” Raccoon couldn’t believe how emotional he was. He fought through tears to finish the message. “Jack, he just was here… he… he… hit me… stole drugs… ran off. I don’t know where he is. Please call me back. I don’t know if you’re even in town. He needs help… Jack…”
Unfortunately, Jack wouldn’t get the message for several days. The campaign was tanking and he was completely absorbed in it. It was stressing him pretty badly. Jack wasn’t used to losing, let alone something as big as a presidential campaign. It was two weeks to election day and things were looking grim. A few of his real estate deals were problematic and liquidating his assets was proving to be much more difficult than he planned.
He knew something was going on with Harrison, but didn’t realize the magnitude of his decline. They’d barely spoken in more than a week and Jack’s texts hadn’t been answered in a few days. In Jack’s messed up mind, he thought Harrison was done with him. There was really no reason to think that way, but his old paranoia was letting thoughts like that live in his head.
Strangely, Harrison thought Jack had given up on him, that he didn’t love him anymore. Those thoughts were put in his head by people who had ulterior motives. The drugs had clouded his perspective so badly, he was convinced his friends and chosen family didn’t care about him.
Rather than call his therapist or talk to someone, Jack just did what he always did. He tried to ease his pain with sex. If it was with someone who would abuse him, that was even better. No matter what was happening in his life, one thing could always help him relax, a good fisting. At least he was practical enough to know that getting the shit kicked out of him in the middle of a high profile campaign wasn’t the smartest idea, so Jack opted for fisting. He tracked down his DC fisting boy, Ethan.
Ethan was young, and looked even younger. He was around 6’ tall, had a thick mass of unruly hair that he hadn’t cut since he was a teenager. He was in DC for school for something related to climate science. He had little regard for his appearance, except for taking care of his body and maintaining perfectly manicured hands. He wasn’t one to dress fashionably. He wore old t-shirts or hoodies and shorts or jeans - usually so tight they looked painted on. He had a pair of nerdy wire rimmed glasses and was young enough to still have some acne. Even though Ethan was actually 22. He looked like he was 13.
The thing Ethan was known for - and why he was so popular as an escort - was his fisting skills. He took it very seriously and as a result he became a master at being a fisting top. Samuel had a fisting obsession and was certainly a skilled top, but Ethan treated his fisting like a vocation. He was obsessed with not only being the best there was, but being someone that provided an experience that would stay with you forever.
Jack’s text asking if he was available prompted Ethan to call him instead. “Hey Jack! Really good to hear from you. It’s been a minute.”
“Yeah, it’s been quite a year. So, are you calling me to personally give me the bad news that you’re not available, or maybe you quit providing your services?”
“Oh no, I haven’t quit. I make way too much money doing it. If I wasn’t interested in a real career, I could quit school and do this full time. As it is, I’m pretty busy. Dax helped me set up something a little more, uh, professional, I guess.”
“Ah, so you’ve doubled your rates and are much more exclusive now.”
“Something like that. You’re so much fun that I won’t raise your rates. Hehe.”
“Whatever, you know that doesn’t matter to me. Shit, I’ll pay you double your new rates. Anyway, I don’t mean to be a dick, but I really need this tonight. Are you available?”
“I can hear it in your voice. You must be having a stressful time. Yeah, I’m definitely available. I wasn’t when you texted, but I made myself available for you. The reason I called is that I have a few other guys I work with and I wondered if you’d be interested in two cute boys instead of one.”
“Hmmm, I don’t want to turn away something fun, but I really need the kind of release you can provide. I don’t want someone else to kill that vibe. Do you know what I mean?”
“Jack, I think I know what you like and I wouldn’t bring it up if I didn’t think he was someone who knows how to handle you just as well as I do.”
“I’m listening. Tell me more.”
“He’s a part of my… team. He’s young, like so young that he’s only been legally able to do this for a few months, but don’t let that fool you. His name is Brent. I met him about the time I met you. He’s good, Jack. Like really good. I’ve trained him myself and I can say from personal experience that he’s just as good with his hands as I am. Maybe even better. He has a few surprises too.”
The thought sent a shiver down Jack’s spine. Two pairs of skilled hands working him over, stretching him, filling him completely. It was almost too much to imagine. But the craving was already there, gnawing at him, demanding to be fed. “Ok then. I trust you. Bring him along.”
“Awesome! You won’t be disappointed Jack. The usual place, right? We can be there in 20 minutes, is that cool?”
“Yep, the St. Regis. I’ll let them know you’re coming and to send you up. I even have some new scotch.”
“Perfect. Jack, you trust me, right?”
“Implicitly.”
“Cool. When we get there, just let us handle everything. It sounds like you really need some special attention so just chill out and let us set the mood. Just give yourself over to us, ok?”
“I am all yours. I’ll just sit here sipping my scotch and wait for you to tell me what to do.”
***
Jack, still dressed in his professional attire, tried to keep his desperation in check as he heard a knock at the door. When he opened it, he was greeted by Ethan wearing a worn out Dr. Pepper t-shirt and tight patterned shorts. His nerdy fashion sense was on full display with black crocs and black socks covered in bugs. Despite his messy hair and scraggly facial hair, Jack couldn't help but find Ethan adorable. Standing behind him was Brent, who couldn't be more different from Ethan. With perfectly styled light brown hair and blonde highlights, Brent looked like he belonged in an H&M catalogue or Helix Studios video. His trendy striped shirt was unbuttoned to reveal his smooth chest, tucked into too-short vintage polyester pants held up by a thick black leather belt. His feet were clad in bright white checkered Vans, but the most noticeable thing about Brent was the massive bulge in his pants - clearly the surprise that Ethan had mentioned earlier.
“Hey, boss,” Ethan said with a smirk, stepping inside. His gaze swept over Jack’s body, lingering on his face. “Handsome as ever, Jack. But man, you look stressed.” He leaned in and kissed Jack on the lips, “no worries Jack, we’re gonna take good care of you.”
“Ugh. It shows, huh? Sorry. I don’t remember the last time I felt this way about my work. Come on in”
Ethan introduced Brent, who seemed as chill as Ethan despite his more forward appearance. “Hey there, stressed or not, you’re one fine looking daddy.” He was pulling a suitcase behind him.
“Thanks, just don’t call me daddy and we’ll be fine.” Jack chuckled. “You do know what I like, Ethan. Do I need to check his ID?”
“I’m 18. Ethan wouldn’t let me do this until I was legal. I just had to have my fun with him before that. Now I get to meet guys like you.”
“Watch out for guys like me. Anyway boys, shall we get started?”
Ethan chuckled, setting his bag down by the door. “Patience, Jack. This isn’t just about you getting what you need. It’s about us.”
Jack blinked, caught off guard. “Us?”
Ethan stepped closer, his presence filling the room. “Yeah. Us. We’re not just here to stick our hands in you and leave. This is intimate. Personal. You said you needed to relax. Like I said on the phone, just leave everything to us. We’re gonna treat you right. Plus, you promised scotch!”
Jack knew he should have expected this level of intensity from Ethan. This is what he was all about. Ethan wasn’t just skilled, he wasn’t just an escort, he was as into the experience as any of his clients were. He was passionate, sensual. He didn’t just fist you, he connected with you. It was obvious he was teaching Brent his ways.
“Ethan introduced me to good scotch. I’m look forward to what you have to offer.”
“And while you’re pouring, Jack, we’re gonna make things a little more chill in your bedroom. You’re getting the whole experience tonight.”
“I’m looking forward to it. Make sure I have your Venmo so I can take care of both of you. Sorry, I wasn’t planning on needing this kind of cash tonight.”
“I know you’re good for it.”
As Jack poured scotch, the boys went about getting the room ready for their night. They laid out candles, put on some chill electronic music, laid out towels, got their various kinds of lubes ready, laid out toys and prepared the bed. They did it all behind closed doors so they could surprise Jack. They sat for a bit, talking and sipping scotch while Jack got caught up with Ethan and learned more about Brent. Jack didn’t have to go into too much detail about his stresses, but he shared some of the campaign challenges and some of the potential issues with Harrison. He explained that he would been hanging out with Cameron, but he was with his family for his sister’s birthday.
“Wow, that is a lot. I’m glad you reached out. You’re way too cool and too awesome to be feeling like crap. I promise you will feel a lot better with me and Brent, even if it just for the night.”
“You’ve got us all night if you want. We’re in no hurry.”
“That’s one of the many things I like about you. Too many guys who do what you do are clock watchers. You take your time. I appreciate that, a lot. You’ll see how much by morning. Consider this an advance tip.” Jack handed each boy a wad of bills. He did have cash, just not the amount he wanted to give them.
“Holy shit! This is the tip? This is what we’ve been getting for a session.” Brent unfolded the bills to discover $600.
“I told you he was generous.” Ethan set his glass down and stood up. “I’d say we’re ready now.” Ethan led Jack to the bedroom, his touch firm but gentle. Brent followed behind. Once in the bedroom, Jack was impressed with the ambiance they created. Ethan walked Jack over to the floor to ceiling windows and turned to face Jack. Brent stood behind him. The two boys began gently rubbing their hands over Jack’s body. They kissed his neck and each other as they began to remove Jack’s clothes. When Ethan pulled Jack’s underwear down he saw the chastity device he was wearing.
“Oh, that’s new. When did you start wearing this?”
“It’s a long story, we can talk about it later.”
Brent stepped around to look. “I think it’s hot.” He brushed his hands over the device and stroked Jack’s balls.
“Yeah, it is, but I kinda liked sucking on your cock. Do you have the key? Can you take it off, even just for a little while?”
“I have a key for emergencies. Please, Ethan, let’s not make a thing of this. You have lots to work with. I’m sorry.”
“Ethan, it is sexy as fuck. And it will add to the fun.” Brent got down on his knees and started licking Jack’s balls. Jack shivered as Brent’s tongue expertly glided over the exposed orbs and even over the device. “Plus, we’re here to fist him, right?”
“Yes, we are.” Ethan moved behind Jack and started kissing his shoulders, moving slowly down his back, lightly touching him all the way down. Ethan’s soft touch gave Jack goosebumps. Brent focused his attention on Jack’s balls. Ethan made it to Jack’s ass and began to lick up and down the crack, gently parting Jack’s ass so he could get to his hole. Ethan swiped his tongue up and down the crack and started to focus on the hole. He loved Jack’s well worn hole and how easy it was to get into. He started to ease his fingers in, two from each hand at first. Brent was now working on Jack’s nipples, biting and sucking on them. Ethan now had four fingers from each hand in Jack’s ass, spreading it open and licking the rosebud that appeared. Brent stepped away to get two plastic bottles, one with fisting lube in it and one with a lube that would create a burning sensation.
Brent stood in front of Jack again and took his hands. He slid them into his shirt so Jack could feel his chest. While Jack felt around, Brent unbuttoned his shirt and tossed it aside. Jack was stroking his perfectly smooth chest. He took one of Jack’s hands and guided it to his hardening cock. Jack gasped as he felt how thick and long it was. Brent used Jack’s hand to stroke himself through his pants, causing Jack to pant. He could feel his cock trying to get hard, but it was trapped in the tight, flat cage and not going anywhere. Brent just stared into Jack’s eyes with his big brown eyes, not letting Jack take his eyes off him.
Ethan was digging his fingers deeper into Jack’s ass, spreading it open and enjoying how easily it gave way to his touch. He lubed up his hand and started to slide it up into Jack’s ass. So many boys would just shove their hand in, which Jack certainly liked, but the way Ethan moved, so deliberately, was something different. Ethan’s hand was now wrist deep into Jack’s hole. Jack three his head back as Ethan twisted his wrist, spreading his fingers wide inside him. The sensation was indescribable, a pleasure that threatened to consume him whole and they were just getting started. Brent took Jack’s hands and pulled them around his waist as he kicked and kissed Jack’s neck.
“Oh fuck,” Jack gasped, his entire body shuddering as Ethan’s wrist breached him and Brent kissed him. Ethan moved deeper, now midway up his forearm. He slowly pistoned his hand up and down, never moving too quickly, making sure Jack felt every movement. Brent pulled Jack’s face to his and started to kiss him with a heated desire. Ethan pulled his hand out ever so slowly and then lubed his other hand up and repeated the same process. Having been told about Jack’s hand fetish, Brent slid his fingers into Jack’s mouth, letting him suck on them. He would lightly push his fingers deeper, getting his hand nice and slick with Jack’s saliva.
“Mmmmm, you like this, don’t you?” Brent cooed as he moved his hand in and out of Jack’s mouth. Brent’s hands were smaller than Ethan’s and could fit into Jack’s mouth, even his whole fist. Brent spit several times into Jack’s open mouth and then pushed his hand in deeper, now in the fisting 'duckbill’ formation. Jack was getting fisted at both ends.
Ethan’s own desire was obvious in his expression and his breathing. “You’re taking me so well,” he whispered, his voice low and sultry. “So fucking perfect, Jack.” Jack could only moan in response, his world narrowed down to the feeling of Ethan’s hand buried inside his ass and Brent’s hand in his throat. Every movement sent shockwaves through him, his cock throbbing in its cage, neglected in the best way possible.
With his right hand up in Jack’s hungry hole more than two thirds to his elbow, he started to push his left hand in. After some slight resistance, Jack’s ass swallowed Ethan’s other hand. Jack let out a muffled yelp as Brent became a little more aggressive with his throat fisting. It wasn’t long before Ethan had both arms at the same depth. Once he did, he opened his fists and moved his fingers around inside Jack, feeling the warm velvety interior of Jack’s body. Then, he clasped his hands together and started to fuck Jack’s ass with both arms, pulling down and then pushing back up. Ethan kept this up, sometimes separating his hands and alternating which arm goes and which pulls out.
“Put your hands behind your head.” Brent whispered as he pushed away from Jack. Once his hands were behind his head, Brent started to move his body in a sultry way, gyrating and twisting. He was just a couple of feet in front of Jack as he did his little dance. Ethan looked over at him and gave him a lustful smile, he knew what was coming. Brent kicked his shoes off and unbuttoned his pants. He danced a little closer to Jack and began to ease them down. Soon, he was kicking his pants aside and all he was wearing was a jock. What was stuffed into it seemed larger than life - and it was. Brent turned around and slid his jock off. It reminded Jack of when Aidan used to do that in his routine at the strip club. When Brent turned around, Jack gasped. The biggest cock he’d ever seen was in front of him. Brent was bigger than Harrison or Aidan, bigger than Joshua, even bigger than the biggest cock he ever knew, Justin.
“Holy fucking hell! Are you fucking serious?” Jack marveled. “No fucking way!”
Ethan chuckled while still fisting Jack. “I told you he was full of surprises.” He gloated as he pulled his hands from Jack’s ass and wiped them off. “And now you get to find out what more than 14 inches of boy cock feels like,” he whispered as he walked away.
“Surprise!” Brent sang breathlessly before he kissed Jack on his cheek and stepped behind him. He didn’t say another word as he turned Jack to face the wind and pulled him back by his hips. Jack put his hands up on the window and yelped as Brent pushed his cock into Jack’s ass, making sure he felt every bit of it. It wasn’t as thick as Justin’s monster, but it was thick enough and the hard length was amazing. “Feeling good, Jack?”
“Oh fuck yes!” Jack was quivering as Brent slowly and deliberately fucked him. “Fuck…”
Ethan slipped off his clothes and managed to maneuver himself in between Jack and the window. He was face to face with his hands around the back of Jack’s head. He kissed Jack deeply with a slow, intentional kiss, scratching the back of his head. “Are you feeling better, my friend?”
“Yes, Ethan, thank you. This is amazing.”
“And we still have so much time together.”
They all moved over to the bed and for a few more hours, Ethan and Brent used Jack’s ass and mouth, but mainly his ass. They used dildos and their cocks, double penetrating Jack in a multitude of ways, two dildos, two cocks, two fists, a dildo and a fist, a dildo and cock. It was a perverse game these boys were playing using Jack’s ass. Throughout it all, Jack was in heaven. Two hot boys expertly using his ass. He couldn’t have asked for a better way to relieve his stress.
“Man, we’ve been at this for hours, Jack, your hole is fucking gaping and that rosebud! Oh fuck!” Brent exclaimed. “This is definitely the best time I’ve ever had.”
“I told you Jack would be amazing. He is insatiable. And that hole? I mean, there’s nothing like it. It is the perfect hole to just keep stretching, keep pushing limits.” Ethan grinned, his eyes glinting with mischief and something deeper, something primal. He looked at Brent who knew exactly what he was thinking. They had talked about trying something and hadn’t found anyone willing or able.
“Think you can handle three?” Brent asked, his tone teasing but laced with genuine concern. He rubbed his free hand along Jack’s lower back, grounding him. “We’ve already got you stretched pretty wide.”
Jack bit his lip, his mind racing. Three fists? He’d done it before. It was pretty intense, but it was something he definitely liked. For almost anyone else this would be impossible, ludicrous even, but Jack? His ass was so used, it seemed silly to not do it. The way they were working him… it felt like anything was possible. He nodded, barely able to form words. “That would be fucking amazing. Do it. Please.”
Ethan smirked, his eyes dark with desire. “That’s what I like to hear.” He climbed onto the bed, straddling Jack who was bent over with his ass at the edge of the bed. Ethan, his hands already slick with lube, started working his hole with slow, deliberate strokes. “Good boy,” Ethan murmured, his tone soft but commanding. “Relax for me.”
Jack closed his eyes, focusing on the sensation of Ethan’s fingers pressing into him again, stretching him. It was familiar now, the way Ethan moved inside him, but there was something different this time. Ethan’s fingers curled and twisted, probing deeper, making Jack gasp.
“That’s it,” Ethan said, his voice a low growl now. “Let me in.” Then he slipped his other arm in and pushed it deep until both arms were almost elbow deep. He pushed and pulled, spreading his arms apart and widening Jack’s hole. Jack was moaning uncontrollably.
Jack whimpered, his body trembling as Brent added his fingers, the stretch intense but intoxicating. He slowly eased his hand in and then with a loud cry from Jack, Brent’s hand slipped through. It was almost too much, but Jack didn’t want them to stop. He had been this full before, and the idea of taking more sent a shiver of anticipation down his spine.
“How are you doing, Jack?” Brent asked.
“Fucking amazing. Oh fuck. Please, don’t stop.”
They adjusted their positions slightly, Ethan shifting slightly to give Brent more room to work. Brent moved his wrist slowly, easing his hand deeper, his arm stretching Jack’s entrance. As his arm moved deeper, breaching the second ring and pushing further, Jack cried out, gritting his teeth, tears in his eyes. Ethan checked in again and Jack nodded his approval. The stretch was painful in the most delicious way, a burning ache that melted into pleasure as his body adjusted. His breathing grew ragged, his hips pushing back instinctively, desperate for more.
Brent and Ethan exchanged a look, their excitement palpable. They repositioned themselves carefully, pulling out and pushing back in, three full arms moving around, in and out, deeper and deeper. The pressure was immense, the stretch almost unbearable, but Jack forced himself to breathe, to relax into it. The boys were in their own ecstasy, they talked about this, but figured they’d never get to try it.
“Oh my god,” Brent moaned, his voice cracking as they began to move in unison. The sensations were indescribable, a pleasure so intense it blurred the line between the three of them. Jack’s body felt like it was being split open, yet every inch of him was on fire with desire.
“You’re doing amazing,” Ethan panted, his own breathing uneven. “So fucking tight around us. Can you feel it? Can you feel how full you are?”
Jack nodded, tears at the corners of his eyes. He could feel everything, the weight of their hands inside him, the way they filled him completely, leaving no room for anything else. It was overwhelming, all-consuming, and he loved every second of it.
“Three fucking fists. Do you have any idea how insane that is?” Brent whooped.
Jack couldn’t answer, his mind too overwhelmed by the sheer intensity of it all. But then Ethan pulled out and leaned into Jack and whispered in his ear, “Fuck Jack, this is the hottest thing I’ve ever done with anyone. Am I crazy to want to push further? What do you think? Can we make it four? Only if you think you can, I don’t want to do any permanent damage or end up in the hospital. But damn…”
Four? This idea seemed impossible, even for Jack Holden’s legendary ass. He looked back at the two boys, the way they were looking at him - like he was some kind of marvel - made him want to try. “What the fuck, why not?”
“Are we really? Fuck!” Brent shouted. “We’ll stop if it’s too much. I mean, this is crazy!”
Jack’s body was trembling. He trusted them implicitly, knew they wouldn’t push him too far, but this could go horribly wrong. And despite the fear, the thrill of trying something new, something no one he could think of had ever done before, was too tempting to resist. Jack had basically done all there is to do, so jumping into uncharted waters was thrilling.
The boys talked through placements and movement, figuring out the best way to go about this. They dumped a ton of lube into Jack’s ass and then slathered their arms. Then, they started, their movements careful and measured. Ethan added his hand first, sliding it up to his elbow. Brent then followed with his hand, with Ethan adding his other arm. They figured Brent’s smaller arm would be best to go last. They both took a deep breath, nervously shaking as they were about to do something potentially dangerous. Brent tried a few spots, pushing and hitting too much resistance. He looked at Ethan in frustration. “Maybe we can’t do this.”
“Maybe, what about here? We came this far, we have to try, right?” Ethan pointed at the space where their arms seemed to create a small opening.
“Are you ok, Jack?” Brent asked nervously.
“Yes… yes!! Please, just try it!!”
Brent nodded and added more lube to the spot Ethan suggested. He gently pushed, Ethan moved his arms, they adjusted continuously, Brent pushed harder. All of a sudden, it happened - his hand slipped through joining the others, and the pain became almost unbearable. Jack screamed out in agony. It was a disturbing sound the boys had never heard before. They knew they couldn’t just yank their arms out, so Brent started to pull back.
“Jesus fucking Christ,” Jack choked out, his voice strangled. “It’s so much. Just…just leave it there.” They waited patiently for Jack’s word, nervous and excited at the same time. “Oh fuck, try to move. Deeper. We can do it…”
Brent pushed in further. One arm elbow deep with Ethan’s almost elbow deep arms, the other arm halfway up his forearm. They were ecstatic as they slowly moved around. They moved up and down gently and maneuvered around. Jack’s hole was ridiculously stretched open. The longer they were in him, the more he wanted. He pushed back on them and they responded by pushing in. Brent got as far as about two thirds of his second arm in and that seemed to be the limit.
“You’re doing it,” Ethan crowed, his voice filled with awe. “Four fucking fists. Look at you, Jack. You’re incredible.”
Jack could barely process the words, his mind consumed by the sensations coursing through him. He felt impossibly full, stretched beyond what he thought was possible, yet there was an undeniable thrill in knowing he was taking something so completely beyond anyone’s limits. His body trembled, his hips rocking back instinctively, seeking more even as his mind screamed for relief.
“How does it feel?” Brent asked, his voice rough with desire. “Tell us, Jack. Tell us how it feels to be this full.”
“It’s—” Jack gasped, his voice breaking. “It’s unbelievable. I’ve never—fuck, I fucking love this.”
Ethan laughed softly. “You’re fucking amazing, Jack. Absolutely unreal.”
Their hands worked together, stretching him even wider, pushing him to his absolute limit. Jack’s vision blurred, his senses overwhelmed by the sheer intensity of it all. He moaned, his body trembling as they continued to work him over. He felt like he was coming apart at the seams, his mind shattered by the pleasure coursing through him. Every movement sent waves of sensation crashing over him, leaving him breathless and desperate for more.
Ethan and Brent didn’t stop, their hands continuing to move inside him, causing him to first piss through his device and then drawing out a painful orgasm. Jack had finally reached his limits. He was utterly spent. “Ok, it’s time…” When they finally withdrew, Jack collapsed onto the bed, his body trembling and slick with sweat.
“Fuck,” Ethan breathed, his voice filled with awe. “That was… I don’t even have words.”
Brent laughed softly, running a hand through Jack’s hair. “You’re a legend, Jack. Seriously. That was…”
“Unbelievable,” Ethan finished, his tone reverent. “Are you okay?”
Jack nodded weakly, his mind still reeling from the experience. “Yeah. I’m… I’m good. Amazing, actually.”
***
Harrison made his way back to Isaiah’s house. Before he was allowed in, he had to hand over the money - and the drugs - that he had on him. By maxing out the ATM cash advance limits on his credit cards, he was able to get almost $7,000. Since he’d met Isaiah, he’d been getting five to eight thousand dollars every day from ATMs. He managed to figure out how to rotate the different cards he had so he didn’t arouse any suspicion, but that was about to catch up with him.
Ever since they met, Harrison had felt a strange attraction towards Isaiah, even beyond the high he got from him. In his rare moments of clarity, he genuinely enjoyed being around Isaiah. This troubled Isaiah because he also felt a connection with Harrison. But he knew it was best to keep his distance and not form any emotional ties; the boys in his world don’t stick around for long. Deep down, Isaiah was a cruel individual and forming relationships was not part of his plan. However, he couldn't deny that he liked Harrison on some level.
Isaiah convinced Harrison to stay at his rundown house in one of Milwaukee's worst neighborhoods. The house was nothing more than a dilapidated drug den, a far cry from the luxury Harrison was used to. He actually lived better when he was homeless. Isaiah wanted Harrison to be readily available for his own sexual needs. He was very into Harrison and liked using him. This meant Harrison was available to anyone at the house for whatever they wanted and there were no limits to how he was used. Quaid was Isaiah’s lieutenant, a dangerous, unsavory character who wasn’t very bright and did a lot of Isaiah’s dirty work.
Eventually, Isaiah planned to use Harrison to make money. As long as Harrison was still a cute, pretty, horny boy, Isaiah could pimp him out to let others have their way with him. Tyler, who Harrison met at the Burrow and who warned him to stay away, was already a revenue source. Tyler was a little like Harrison. He was young, cute, came from money and had been lured into this underworld by Isaiah. His boyfriend was Johnny, a sleazy 30 something guy who ran drugs for Isaiah and was sort of a bodyguard.
Isaiah was relentless in turning Harrison and Tyler into addicts who were dependent on him. They were just two more in a long line of boys Isaiah had ruined.
***
“See, when you’re a good boy, I take care of you.” Isaiah asserted as he gave Harrison his fix.
“Yes, thank you, Isaiah. You’re always so good to me.”
Harrison's body shook as the needle pierced his skin, sending a cold sting through his veins. As the heroin flowed into his system everything else faded away into a peaceful blur. His eyelids drooped shut, and he let out a soft sigh of relief.
"That's it, pretty boy," Isaiah drawled, brushing the hair from Harrison’s face. He stared at him for a few minutes, a crooked smile on his face. Isaiah admired just how attractive Harrison was, and he could see the slow deterioration of the boy from his eyes, to his skin, to his mouth. “You are so beautiful, Harrison. You might be the most beautiful boy I’ve found yet. It’s a shame you won’t last. You boys never do.”
Harrison didn't respond. He couldn't. His mind was already drifting, floating on the warm tide of the drug. Isaiah's hands groped him, rough but not unkind, slowly moving about his body, removing the rest of his clothes.
Isaiah chuckled, "We’re going to see just what you’re made of. Don’t worry, I won’t work you too hard too fast, that cash I get from you is nice.” He deserved it. Did you see how hard that guy fisted him? And he didn't even whimper." Harrison struggled to keep his focus as Isaiah loomed over him. His body felt heavy and his thoughts were muddled. Isaiah leaned over him, a sinister grin spreading across his thin lips. "How are you feeling, Harry?" Isaiah's voice was almost gentle.
Harrison blinked, struggling to form coherent words. "Good..." he slurred, his voice barely audible. "So goooooood."
Isaiah's smile widened, a twisted pleasure glinting in his eyes. "Good," he purred. "Do you know what comes next?"
Harrison nodded, though he wasn't sure if he truly comprehended. Everything was hazy in this state, every sensation dulled but still present. Deep down, he knew that something was about to happen, something he both feared and craved.
With a rough tug, Isaiah stood up and pulled Harrison off the couch, forcing him onto his knees. Despite his trembling legs, Harrison obeyed and sank to the floor. He could feel Isaiah's commanding presence looming over him as the world spun around him. Harrison stumbled but Isaiah's hand on his head kept him upright as he unbuttoned his jeans and let his nine inch cock spring free. "Open your mouth," Isaiah demanded in a calm tone.
Harrison obeyed without question, too lost in the foggy haze of his mind to resist. He took Isaiah's hard cock willingly into his mouth, wrapping his lips around the tip. Isaiah groaned and tangled his hands in Harrison's hair. "That's it, boy. Keep it right there. I have a little treat for you, I know how much you love this." He slowly began to piss into Harrison's mouth. At first, Harrison struggled to swallow, causing some of the rank liquid to spill down his chin. But eventually, he started to eagerly accept and swallow the bitter yellow liquid.
"You're such a good little toilet," Isaiah praised, relishing in his power over Harrison. "I'll save the stuff you really love for later. If you’re a good boy, I’ll even let you eat right from my ass."
Harrison's mind was muddled and he struggled to understand what Isaiah was saying or what was happening around him. His body felt heavy and if Isaiah wasn't holding him up, he'd surely fall to the ground. The taste of urine in his mouth was strangely satisfying. Even though he had only been living in this house for a few days, he had already become accustomed to this new way of life - drugged, used, and taken advantage of by whoever desired him.
Isaiah finished pissing and pushed his length further into Harrison's mouth. "That's it, pretty boy. Suck it like you mean it."
With eagerness and clumsiness, Harrison followed Isaiah's instructions and started sucking his cock. Isaiah thrust deeper, pushing more of himself into Harrison's mouth. Despite the overwhelming feeling, Harrison didn't gag, his natural ability to swallow cock had not been diminished by the heroin.
"Fuck boy, you're really good at this," Isaiah moaned, tightening his grip on Harrison. "Wish all my boys were as willing and talented as you."
Harrison choked slightly, but didn't resist. He craved this, needed it desperately. The drugs had numbed any sense of self-preservation, leaving him hollow and eager to please. All that mattered was pleasing Isaiah, obeying his every command. His desire for sex was previously insatiable, but now it felt like a vital necessity.
Isaiah enjoyed Harrison's oral skills. Even in this state, Harrison was exceptionally talented at oral pleasure. When Isaiah was ready for more, he barked new orders at Harrison. "Get on all fours," he instructed, pulling out of Harrison's mouth.
Harrison quickly complied and dropped to his hands and knees. He was so fucked up, he fell onto his face and struggled to push himself back up. Isaiah got behind him, his body pressing down on Harrison. "Spread those legs," he commanded in a low growl.
As Harrison complied, his body opened up to Isaiah's touch, sending shivers down his spine. With a mischievous grin, Isaiah reached under the couch and retrieved a well-used dildo, still slick with lube and whatever else had gotten on it from its last use. He wiped off the dust and dirt before coating it with more lube from a bottle on the end table. Isaiah spread lube onto Harrison's already abused hole, his fingers trailing down his thigh.
"I know how much you love this," he promised, positioning the dildo at Harrison's raw hole. The dildo wasn't too big by Harrison's standards, but it still measured 13 inches long and was fairly thick. As Isaiah slowly pushed the dildo in, a sharp gasp escaped from Harrison's lips. Moving with deliberate slowness, Isaiah eased the dildo deeper, sliding in and out, until it hit that spot that made Harrison arch off the ground in pleasure.
Harrison felt a sudden warmth spread through him as Isaiah leaned in to kiss him, the intoxicating mix of lust and drugs heightening his senses. It was these tender moments that contradicted Isaiah’s true nature. With each thrust of the dildo, Harrison moaned softly, surrendering himself completely.
"You're doing so well," Isaiah praised, his voice thick with desire. "But I know you want more."
After a while, Isaiah tossed the dildo aside and positioned himself behind Harrison, thrusting his cock inside him. Harrison barely reacted, his body limp and unresisting. As Isaiah pounded into him with increasing force, Harrison's body slid along the floor, his head bouncing against the leg of the nearby couch. Pulling out briefly, Isaiah then flipped Harrison over on his back and impaled him once again.
"Your hole is so loose," Isaiah growled as he thrust into Harrison's eager body. "I love it that you're this loose, so worn out, so sloppy."
Harrison was in a state of euphoria, his inhibitions washed away by the intense sensation of Isaiah's thick cock filling him entirely. His momentary burst of energy allowed him to wrap his legs tightly around Isaiah's waist, pulling him closer for even deeper penetration. Nails clawed at Isaiah's back as Harrison begged for more. "Harder," he panted desperately. "Please, harder."
Isaiah complied eagerly, each thrust becoming more powerful and precise than the last, slamming into Harrison with ruthless abandon. The sound of Harrison's cries grew louder and more frenzied. Suddenly, he felt a wave of nausea wash over him and began to vomit uncontrollably. Without missing a beat, Isaiah rolled Harrison on his side, still fucking him, and turned his head to the floor to prevent choking on his own puke.
"Fuuuuck…Isaiahhhhhh…" Harrison shouted through gasping breaths, spitting up bile and saliva as he writhed beneath Isaiah's relentless assault. "Mmmmmmorrrrrre…"
With Harrison begging, Isaiah gave it to him. He slid his hand into Harrison’s ass and began to jerk his cock inside Harrison’s ass as he fucked him. He finally reached his peak, releasing a thick load of hot cum deep inside his gaping ass.
With a loud satisfied sigh, Isaiah pulled out and stood up. He rolled Harrison over onto his stomach in case he vomited again, and left him lying there on the floor. Harrison remained motionless, covered in vomit and saliva as he moaned mindlessly.
A few minutes later, Quaid appeared and dragged Harrison by his legs into his room, dumping him unceremoniously on the floor. As Harrison drifted off into a deep sleep, his body still trembling from the intense experience, Quaid couldn't help but feel a sense of pity for the boy who they were treating so brutally. But for now, all he could do was leave him there to sleep off his intense high.
From that day on, Harrison effectively disappeared from his previous life. His phone was taken away, his credit cards were taken and used to continue sucking cash from his accounts. He was regularly drugged and was kept locked in a room with Tyler. He was let out to please Isaiah, or the other men, or to be pimped out to whoever Isaiah brought over. He was brought to the Burrow to be used and abused as well. All the time with Isaiah charging others to use him. He kept every penny.
Harrison had finally hit the bottom.
