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by Maecin
Rated: XGC · Short Story · Erotica · #2293175
Jack deals with his families enemies & feelings of inadequacy the best way he knows how.
          Jack woke to the afternoon sun finally reaching his bedroom window, groggy and still in yesterday's shirt he idly glanced at his phone. 2:23PM, well past noon again. The assistant would be here soon.
Giving himself a moment to wake properly Jack cracked open a can of energy drink from his mini-fridge and sauntered into the bathroom, there was still time for a shower and he preferred to be clean for this.
As the steam faded Jack inspected himself in the mirror, his lithe build and short frame made him look small in the massive penthouse bathroom, small and lonely. He hated both. Jack's fast metabolism and home gym had spared him the love-handles thus far, and despite his lecherous, bachelor lifestyle his body remained toned, his butt perky and skin smooth. He wanted to look good for his afternoon play, it shouldn't matter. But for some reason it did.

          The doorbell rang at exactly 2:45PM. The assistant was dressed in his usual navy-blue suit and horn-rimmed glasses, a stark contrast to Jack who was still in his bathrobe. The assistant was holding a neat hardwood box with 'Eivanson Industries Inc.' engraved upon it.
          "As per your request Mr. Eivanson, 4 inches each." The assistant declared in a tone a doctor might use to prescribe medication. 'Mr. Eivanson' That's what people called his father, though few showed Jack the same reverence.
          "Thank you, anything else I should know?" Jack said, carefully taking the box from the assistants' hands. "I've not inquired your father as to their origin, I'm sure you have your methods of finding out if you are curious. However, standard procedure is in effect here, they must all be terminated."
          Jack never quite got used to the assistant's matter-of-fact way of speaking, even whilst having been around him more than his own father by now. "Termination is what I do best." Jack tried to say with some levity, the emotionless blank stare of the assistant quickly shutting that down. "If that'll be all Mr. Eivanson, I must report back to base."
          "Yeah, of course, safe travels, I'll take care of this." Jack shook the box slightly, it felt light this time, but with several distinct weights inside. The assistant nodded and turned to leave in a single motion. Before long Jack was alone again, he didn't consider the contents of the box to be true company.
          He laid it on his crumpled bedsheets and put on some actual clothing; he'd be removing it again soon enough but enjoyed the process. Jack took one more look in the mirror, mussing his dirty blonde locks into something that resembled a deliberate coupe. He was an attractive young man and knew it, he'd been popular with both guys and girls back when he still dated. Nowadays there was a bleakness about him though. His lack of self-care made him a disheveled imitation of the boy he was in his college years, back when he could actually love, when the truth of his life hadn't set in on him yet. The ruthless empire he was set to inherit, one that would consume him if he didn't harden himself.
          He looked once more at the box; in the silence of his lonely penthouse, he could just make out the faint calls emanating from it. His father was happy to indulge him in this, a band-aid on his failure to be present in his life Jack supposed. One that taught him to steel his heart to the plight of his underlings, and proved that Jackie, the loving boy he once was, is now gone.
         
          With a fancy remote he set the light in his room to a faint scarlet, the reddish hue obscuring his flaws and making the whole ordeal even more ominous for his captives, he sat down on his side next to the box and carefully removed the lid. Four tiny, nude silhouettes sat huddled in the corner, instantly looking up at him. Reactions often varied greatly, this time three remained still, resigned perhaps, or frozen in fear, it was hard to make out their expressions in the dim light. One however, who looked to be about middle age and overweight, began to bawl and cry, altering between gasps of disbelief and horrified screams at the looming giants face above him. He looked back several times at his compatriots, as if to make sure they were seeing the same thing he was but got little from them in the way of affirmation. While seeing his quarry like this gave Jack a certain primal, predatory satisfaction, he'd always disliked the panicky ones. It was hard to get any sort of interaction out of them, and if pushed too hard they tended to just pass out.
          Jack decided to give the chubby one a moment to let his reality sink in and started with another, reaching into the box he gently picked up one of the quiet ones. His expression was stoic but defiant, he guessed the man to be in his late twenties. Dark skin, shaved head and a cut, lean physique, the type Jack would have fallen head over heels for in high school. Leaving the rest to stew in their dread Jack decided to investigate this one. He threw himself onto his bed and dangled the man an arm's length above his face. Jack spoke up, loud enough for the contents of the box to hear him clearly too. "I'm sure you heard what my associate demanded I do with you; I am however free to decide your fate myself." He lied. The man gave no verbal response. "You see, someone like me has everything one could want for, everything but real intimacy. Relations are complicated in my position, that's where you come in! Keep me happy and I promise you'll have a great life here." He noticed the tiny man's expression break for a moment and betray the terror he'd been hiding so well. "I know who you are." The man spoke with wavering confidence. Jack was intrigued, tilting his head he gave him a playful smile. "You do? That's incredible, I haven't got a clue who you are. Why don't you tell me? Remember, cooperation is greatly appreciated."
          A brief silence followed, then, the man answered. "My name is Daron, Daron Tenton, I... I'm a private investigator. The CIA has a file on you, Jack Eivanson, son of a suspected arms dealer. I was about to prove those suspicions, as well as your families' crimes in espionage, human trafficking, and theft of highly classified technology. The latter, I'm guessing, is what your goons used to do this to me."
          Jack was taken aback for a moment; it was men like this that would scare the hell out of him if he had to deal with them full-size and in the field. Thankfully here he held all the cards. "Impressive Daron. You seem like a rational man, one with great self-preservation instincts. Now unfortunately I don't really need a PI, I do however desperately need a boyfriend, or at least someone who can perform the duties of one." He brought Daron close to his mouth, letting his warm breath wash over the man's tiny body. "At first a professional such as yourself might find this humiliating, but I trust you'll learn to appreciate your new position, think of it as a permanent vacation." Jack continued, whispering under his breath so that only Daron could hear him. "I need you to do really well, if you don't, I'll eat you alive." His tongue briefly lapped over the tiny man's face, causing him to sputter and cough through a sheen of saliva. Jack didn't await any further response and brought the man down the length of his body, using a free hand to pull both his pants and underwear aside.
          Jack's dick stirred as Daron was laid beside it, the confused PI struggled for grip on the small patch of pubic hair that Jack kept before he pulled his underwear back over him. It took a few moments for Daron to orient himself and an impatient Jack lightly pressed him into his growing dick. To his delight it didn't take long for the shrunken man to start trying to please him. Jack was sure he only did so because he still held out some sort of hope of escape, but that didn't matter. He pulled down the rest of his pants so that Daron wouldn't be too restrained to perform his duties and after basking in the feelings of power and subjugation, as well as the surprisingly deft hands of his captive, Jack blindly reached back into the box and pulled out another. It was the chubby guy this time, he had stopped screaming but still appeared to be in some sort of shock, creepily maintaining eye contact with a deer-in-the-headlights expression even after Jack put him down on his chest. He wasn't a pretty man, he had pasty skin, a thin brown comb over and was totally out of shape. He doubted this one would last long no matter what he decided to do with him, even the thought of eating him whole didn't feel nearly as enticing as it had with Daron. He didn't feel like entertaining this long. "Alright chubby, your friend is down there pleasuring my dick right now and he's doing a great job." He made sure to exaggerate a moan in between his words. "But I'm a pretty needy guy, so what I need you to do is get down there too and eat my ass." Frustratingly it looked like his words didn't even registering. Annoyed, Jack spoke up again. "Hey, I'm talking to you. I just cleaned myself up if that's what you're worried about. You're going to have to pull your weight here."
          Sheepishly the man lifted his arm and pointed back at the box. "...C...client... It's my c... client you want." Jack groaned and reached back into the box, pulling out a handsome dark-haired youth. "This one?" The fat man nervously shook his head. Jack put the little guy back and tried the last one. Another who seemed to be pushing forty, scrawny this time, and vaguely familiar. Snapping his head back at the little fat man on his chest Jack asked for affirmation. Scared shitless by the giants glare he quickly nodded, looking almost relieved as if he had accomplished anything here.
          "I told fatty here to go and eat me out, but instead of listening to me he told me I wanted you. Care to explain?" Jack told the scrawny man with a stern look. He was a squirmy one, Jack liked those, he spoke real graciously and polite too. "Heh, listen Jack, he's uhm, he's my lawyer, he got me into this whole mess, said I should spill the beans to the authorities after I got caught, never did of course, never would!" Jack gave him a puzzled look; seems this one knew him by name too. "Yet apparently you told your lawyer all about it, I believe my father is quite clear about not doing that. Tell me, how do you know my name?" The little man looked puzzled for a moment, then managed to compose himself again.
          "Oh, c'mon Jack! I'm Paul! Paul Melainy! I... I've been running with your dad when this whole organization was still in its infancy, hell I've known you since you were a kid! And the lawyer thing... I was looking at two times life without parole! He said he could get it down to maybe 12 years if I gave him something to work with, but I never told him he could tell the cops nothing! You gotta believe me here I-" Jack cut him off with a shush, in a way one might shoo away a cat. Now that he looked closer, he did recognize him, the name Melainy coming back to him too. He recalled him being nice enough, used to muss his hair whenever he'd be over at their mansion, even took him out on a motor ride once. None of that mattered now however, he hadn't thought about Paul in close to a decade and was sure his father knew where he'd send him, his life was forfeit along with the others.
          "That's great Melainy, but I'm sure you understand you're not here by mistake. You can't be out there anymore and it's my job to make sure of that, but being with me can be much nicer than prison. Now I told your representative here to go and eat my ass and he's still not doing that, do something about it or I'll shove him up there and have you do it instead." With that he placed Melany on his chest as well, who, after a moment of consideration slapped his fat lawyer in the face. "Do what the kid says Whitman! I'm only here cuz' your lack of discretion." The little lawyer stumbled backwards and tried to argue, only to be slapped again. It was an amusing display, but it seemed the ruckus distracted Daron from his duties. Deciding to take matters into his own hands Jack reached down into his underwear grabbing both his dick and the little PI, using his thumb to press the man's head into his glans he slowly began to rub him up and down. Paul took notice and appeared to have lost patience for his groveling lawyer, dragging the man by his jowls down Jack's torso and tossing him down onto the bed. Skillfully sliding down the giants hips himself before resuming the struggle. Jack was pleased with his loyal new servant; Paul had always been a good follower.
          Taking a brief pause from masturbating Jack removed his underwear to grant easy access for Paul to fulfill his demands. After casually tossing it off the bed Daron was finally out in the open again, the hardened professional looking hilariously out of his element perched on top of Jack's now throbbing cock.
          He felt movement down at his butt, it seemed like Paul was literally trying to jam the lawyer into his cheeks. Jack couldn't help but grin, he was loving all of this, the power, the domination, and the pleasant sensations provided by his struggling captives. It alleviated some of his insecurities and made him feel like he belonged.
          While his efforts were endearing four inch Paul wasn't going to accomplish much like this, Jack reached down his side and pulled on of his cheeks aside, revealing his asshole which twitched in anticipation. It wasn't long before he felt the man's doughy face pressed against it, faintly hearing Paul yell "Lick! Lick or you're dead!" Jack gasped as the frightened lawyer obeyed, getting a rim job from someone the length of your finger wasn't as intense as at full-size, but the tiny tickles combined with the overwhelming feeling power made for a whole different kind of experience. "Ha -aah, don't stop, make sure he keeps at it Paul."
          Jack returned his attention to his manhood and the tiny PI who straddled it, clenching his hand around both and masturbating in rhythm with the tiny licks down below. He could cum quickly like this, but knew if he did, he'd lose all interest and just dispose of them, he wanted more.
          Reaching back into the box he grabbed the last one, the handsome one, Jack lifted his shirt and pressed the youth down onto his chest. He didn't feel like conversing with them anymore. "Play with my nipple, now." He ordered, pressing his tiny head onto it. The young man quickly obeyed, hastily trying to please with a combination of kneads, licks and nibbles, it was good enough. For a while Jack basked in the worship, so many nerves were firing at once his mind started to fog. Jack picked up the pace of his stroking, tiny Daron now no more than a masturbation-aid, along for the ride while getting slathered in pre-cum. Without really thinking about it Jack used the hand he'd been spreading himself with to quickly snatch Paul from his post, in a single motion he brought him up to his face and stuffed him in his mouth, blocking the terrified man's escape with his hand and muffling his own moans. He tasted the writhing body for a moment, tossing Paul around and pressing him to the roof of his mouth. Salty, but dry and a little dull, older guys often were. Tilting his head Jack swallowed hard, feeling his throat clench around the erratic lump as it quickly sank beneath his collarbone. If nothing else Paul Melainy was a fighter, the struggling only increasing as the seconds wore on. Feeling the tickling sensation in his core Jack felt his orgasm rise, suppressing every natural instinct he let go of Daron and his cock. The dark-skinned man drooping down onto his abdomen, utterly exhausted.
          Slowly the extreme tension began to subside as Jack's breathing stabilized.
Not yet. He thought. He looked down across his half-naked body, his nipple still prickled pleasantly as the last guy hadn't dared to stop his efforts for a moment. Daron was almost spent, but that was to be expected. Jack noticed the little lawyer had stopped licking and somehow managed to pry himself free from his cheeks. Less than twenty seconds without his enforcer there and he shirks his duties. He'd expected as much, and was done with foreplay anyway.
Jack leaned aside and reached into his drawer, he pulled out a bottle of premium, unperfumed lube and squirted a generous amount into his right hand. While raising himself up into a seating position his hoodie fell back down and his diligent toy was send tumbling down it, falling beside Daron. Jack could see the little lawyer just sitting there in between his legs, staring with a blank expression at the cleft he'd been forced in between. He reached over and grabbed him, quickly covering the overweight man in lube as he maneuvered him in his hand. "Please, let me go." The man complained, his voice completely monotone. Jack answered in the sweetest and most caring tone he could muster. "Wilson, was it? Winston? Anyway, you aren't very good at this, and I just swallowed your client whole. So, I'm just going to take it from here. I do hope you still have some energy left because I'm going to shove you up my ass now." Jack finished by rubbing his thumb across the mortified man's face, having covered him head to toe in lube.
          "...Whitman, the name is Whitman." The lawyer mumbled, even as Jack sat back and spread his legs wide. At first, he gently teased his hole with Whitman's head, rubbing circles around it while carefully prodding at the center. He had expected at least some sort of response, begging, cursing, bargaining or even just the erratic screams of cornered animal, but the man remained rigid and silent. Oh well, at least his pear-shaped body makes for a decent butt-plug. Jack mused, before finally applying pressure and pushing the man inside up to his shoulders. Jack arched his back and gasped, even at this size Whitman's width easily exceeded two of his fingers. With a deep breath he relaxed and applied yet more pressure, this time pressing down two of his fingers onto the lawyers rear. Once the bulk of the man's body had passed inside Jack, his asshole quickly enveloped the rest, greedily drawing Whitman in until only his soles stuck outside.
          "Ah, fuck. You- you're a lot Wilson." Jack moaned. Clenching his asshole around the man's ankles. He recalled saying similar things to his high school sweetheart whenever he'd thrust into him. Taking a moment to get used to the new pressure in his ass Jack glanced down at the two men in his lap. Daron was on his hands and knees, still struggling to catch his breath. He might have broken a rib in the excitement, at any rate he could use a break. The other was staring up at Jack with an awed expression, this one looked familiar too. Probably another one of my dad's cronies. He figured.
Jack reached back in his drawer and pulled out a middling sized dildo. "This will do, hope it'll motivate Wilson to at least do something." He said to no one in particular while lining the toy up with his butt. It was slightly thinner than Whitman but harder, and a lot longer. "Let's get you nice and deep..." He moaned, slowly inserting the head into himself, the tiny lawyer was finally sealed in fully and Jack shuddered as he felt the lump pushed past his prostate. Still nothing. He lamented as it seemed Whitman had either froze or passed out. Maybe I'll put in one of the other two later. Jack pushed the toy further in until he was satisfied with Whitman's position, then he began fucking himself in a quickening rhythm. He'd done this countless times, alone or with shrunken aid, and in the past with his flings. His body greedily accepted the tiny lawyer and the silicone as it slid in and out of him. Jack let himself fall back down into the bed, trying to get comfortable for his rapidly approaching orgasm. "Huff, y... you two, my dick... now." He commanded his remaining two playthings, twitching his cock while giving them a venomous glance. Both obeyed in an instant, reaching to please their giant captor while his last victim was being rammed up his colon mere inches below them. The young one climbed up the shaft, riding it like a bull while desperately rubbing his naked body along to try to get some sort of friction, Daron tried to work his glans, rubbing his tiny hands along them trying not to get a mouthful of the pre-cum leaking from the slit above. Without help or proper instruction they were clumsy and ineffectual, but it didn't matter, Jack had been at the edge for a while now.
One particularity enthusiastic kick from Paul deep within him hit just at the right time, with a trembling gasp Jack pushed the dildo in up to its base. He heaved and moaned, coating Daron in cum as his battered prostate caused it to ooze out of him in a lengthy and ineffectual stream. Leaving the dildo where it was Jack quickly grabbed his dick along with its tiny rider, stroking hard to extend his orgasm, shooting out the rest of what he had onto his stomach and chest only seconds later.

...

Jack took a moment to bask in the afterglow. "-Ah!" He gasped at the sudden movement inside, it seemed Whitman was conscious after all as he writhed with whatever strength and air he had left. Relishing the feeling somewhere deep below his navel, Jack knew from experience it wouldn't last long. He already felt himself get horny again despite the intense finish he just had.
Fuck. Why now, why not ten seconds ago you useless fat- His train of though was interrupted by the feeling of rapid little footsteps across him leaving a sticky trail behind. It seemed Daron was making a run for it. Jack let him jump off and run about two feet across the bed before snatching him up. A frustrated scream coming from the man who had thus far been so composed.
          "Remember what I said Daron, you actually did great and I was about to reward you, but now..." Jack lied again, playing with the cum-covered man in his hand.
Daron coughed violently, hacking and wheezing as he tried to clear the sticky mess from his face. "F... Fuck you! You're a monster! I've seen cartel killers with more decency! Degenerate fuck! I'll-" Jack stifled his words by rubbing him facedown into a puddle of cum on his abdomen. He pulled Daron back up and looked down at him with a vindictive glare. Speaking up before he had a chance to continue his rant. "We could have had so much fun Daron, I'd have given you the biggest, best blowjob ever. And hell, it feels like Wilson is almost spend, you'd have become my favourite little toy, feet first with time to breathe and everything. We'd shower together after, rubbing you all over myself like the worlds most spoiled little loofah. But if you're gonna be like this... well, say hi to Paul I guess." Jack had begun to lift him above his face again, only to unceremoniously drop him into his open maw. He didn't mind the taste of his own cum, the fact that the feisty and furiously fighting Daron was covered in it only added to the experience.
Jack lapped Daron with his tongue while the shrunken PI fought for his life, battering his fists bloody on Jack's teeth and trying to wrestle down the giant tongue as it toyed with him. His effort was admirable but ultimately meaningless. With a quick tilt of his head Jack swallowed him down, taking in a deep breath as his prey passed through his esophagus. Daron's arrival in his stomach seemed to reignite Paul's struggle, delighting Jack with the tickling sensations inside of him as both men continued their pointless resistance.
Feeling his lust start to ramp up again Jack turned his attention to his last remaining plaything. "Looks like it's just you and me now handsome, did any of what I just told Daron sound enticing? It could all be yours." Jack tried to give him a reassuring look, as much as someone who just ate two people and stuffed another up his ass can. The tiny man remained silent, mouth agape in some form of disbelief. There was something odd about this one. "Care to tell me your name lil' guy?" Jack asked nicely.

         "...Jackie?" The young man stammered. Failing to give his own name.
Jackie? No-one has called me Jackie since my high-school boyfriend. Jack mused idly.
         "..."
         "JASON?" He yelled in confusion. "JASON - FUCKING - TAYLOR?" The tiny man quickly nodded. It finally dawned on Jack, the familiarly, the strange attraction he felt. It had been a couple years and he had some stubble now, but it was definitely him. There he lay, naked and covered in his own cum with his ex literally in the midst of it all, having just witnessed him commit atrocity after atrocity to him and other, all for his own empowerment and gratification. Jason looked at him with a mix of fear, awe and disbelief, it suddenly made Jack feel wildly uncomfortable. He wasn't sure what to do, or what he could even say. The absurdity of it suddenly too much. "What... What the fuck are you doing here?!"


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