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It was hot in iTrapped’s office.
It usually was, given the AC had been broken for months. Usually, the con artist would call a repairman in to fix it, but as of late, he’d been adverse to the idea of anyone coming into his office without his permission, without background checks. What if they found something on him? What if they reported him to RHQ? Those reports rarely did anything, but he wasn’t going to risk it.
Today was different; someone was coming in.
It was a necessity. That gambler had been running around with new people—people iTrapped didn’t know. He trusted in his plan, in himself, to pull through, but just to be sure, he felt the need to hire an extra pair of eyes.
He didn’t often associate with the mafia. They got involved with crime just as often as he did, but they were so… blatant about it. Brash. Reckless. iTrapped hated recklessness. But they got the job done, and they promised anonymity.
The con artist sat at his desk, sweaty hands folded in front of him against the lacquer. A folder was carefully placed at the other side of the desk where the other chair was. iTrapped was careful not to touch it.
He tapped his foot against the wooden floor, keeping a steady rhythm as he attempted to look anywhere but the door in front of him. He wasn’t nervous. He wasn’t. He’d met Mafioso before. He would be fine.
He glanced at the clock on his desk, which clicked gently, constantly. The noise used to annoy iTrapped, but he’d grown to find comfort in it. The clock was always ticking. It didn’t stop.
It was 8:03 pm. His guest was supposed to arrive promptly at 8:00.
The con artist felt his chest grow tight. What if someone had caught him on the way inside? What if he snitched and told the authorities who he was meeting? What if iTrapped was in trouble?
A soft, yet sharp knock at the door shook iTrapped from his internal panic. He swallowed, staying silent.
A voice from the other side spoke up after a second. “Ah… hello?”
iTrapped fidgeted with his sleeve. “… Come in,” he invited, barely above a whisper.
The door clicked open, revealing a very large man. He wore a black suit and tie, with gray pinstripes running along the fabric of the jacket and pants. Sizable hands were encased in similarly black gloves, folded in front of him. His hair was visible from under his fedora, which he tipped as a polite greeting.
“Good evenin’, Mr. iTra—”
“You’re late,” iTrapped spat, his eye twitching with a scowl as he stood from his desk. He didn’t like how far he had to look up to make eye contact with the mafia boss.
Mafioso tilted his head. He was smiling just a little, a sharp, gold canine poking out. “Of course. My… apologies.”
The con artist scoffed, glancing to the folder on his desk, then the other chair. “You can take a seat. Start looking through the folder.”
Mafioso complied, the relatively small chair creaking as he sat down. His hands hovered over the folder as he scanned the label on the front; Chance, it read.
“Like I mentioned in the letter,” the con artist cleared his throat, “I need you to keep tabs on Chance. I provided all the information you’ll need in there—phone numbers, addresses, every person he’s ever bought a Limited from. You shouldn’t need anything else, but if you do, you can… contact me.”
The mafia boss nodded, still smiling. “You really did your homework, Trappy. ‘M impressed.”
iTrapped felt himself flush, humiliated. “I-I don’t want there to be issues, like last time.”
There was a certain tension in the room that neither of the men could quite place. It unnerved the con artist to no end. Mafioso had this effect on him—he wasn’t uncomfortable, but at the same time, it felt like he was suffocating around him.
The larger man was just… intimidating. That must’ve been it.
Clicking his tongue, Mafioso broke the silence. “So, am I still startin’ on Wednesday?”
“I-I need you to start sooner.” iTrapped was acutely aware of how nervous he sounded. He cursed himself internally. “I just… I need information by tomorrow. Is that—?”
The mafia boss laughed. “That’s fine.”
iTrapped exhaled shakily. “Good. That’s… that’s great.”
Mafioso stared for a second, eyeing the smaller man up and down. They were eye level, despite the fact that iTrapped was standing. His hands left sweat residue on the desk beneath them, and Mafioso could’ve sworn he could see them shaking. He grinned like a shark.
“What’re you so nervous for, anyway?”
iTrapped blinked. “I’m… not.”
“Ya clearly are. You were like this last time too.” Mafioso leaned back in his chair, his legs spreading out casually. “Me ‘n my boys can get the job done for ya. Chance won’t even know we were there. Don’t gotta worry.” The last sentence was spoken in a softer tone, like he was attempting to calm down a frightened animal. iTrapped swallowed.
“… I need all the information I can get on Chance,” the con artist said, staring to the side at the wooden floor beneath him. “I want to be prepared.”
“Prepared for…?”
iTrapped scratched at the stubble on his jaw. He wasn’t sure.
Mafioso noticed his hesitance, sitting up and standing. He towered over iTrapped, leaning over the desk as if to get a better look at him. The smaller man felt himself cower.
The larger man tilted his head, like he was debating something in his head. His eyes drilled into iTrapped, making him feel smaller than he already was. “… You’re like a scared little dog.”
iTrapped let out a noise. He tried to pretend he didn’t.
“I’m not paying you to… to mock me.”
“C’mon, look at’cha. All dressed up in that little suit, that little bowtie. You think ya mean business, huh?”
God, this was humiliating. “I-I…”
Mafioso let out a low chuckle, one that sent waves through iTrapped’s chest. The mafia boss leaned forward a little more, bringing his hand up to caress the side of the con artist’s face. He rubbed his thumb back and forth. iTrapped felt frozen.
“Trap,” Mafioso eventually mumbled under his breath. “I… need you. So bad.”
And the smaller man didn’t know what to say.
He supposed there was something about the larger man—his voice, his commanding presence, the way he seemed to get whatever he wanted—that made him feel weak. iTrapped felt hot all over. Mafioso spoke up, noticing his silence.
“How ‘bout I help you out in… other ways?”
A surge of confidence bloomed in iTrapped, and before he could second-guess it, he reached out towards Mafioso’s tie, yanking it down. Their lips collided in a moment of heat and yearning, both of them desperate to feel something they hadn’t felt before.
The kiss quickly turned passionate; the mafia boss slipped his tongue through iTrapped’s lips, prompting a whine from the smaller man. The con artist crawled up on the desk, his knees and suit shoes against the shiny mahogany as he melted further into the kiss. How long had this been lingering between them? How did Mafioso know it was there?
“Fuck,” the larger man growled against iTrapped’s lips. “I need you so bad, little pet.”
A jolt of something electric went straight to the con artist’s dick, his pants already feeling tight. “I’m not y-your fucking… pet…”
Something shifted in Mafioso—iTrapped could tell. It was like he expected total compliance, total submission. His eyes widened slightly, and his gaze darkened.
“What was that, Trap?” He asked, voice soft in tone, but not in delivery. The smaller man swallowed, hardening his expression.
“I’m… not your pet,” he mumbled, fingers curling into the fabric of Mafioso’s suit as he shook with excitement. “Stop treating me like a goddamn dog.”
Mafioso hummed, tilting his head. His eye contact was relentless, piercing through iTrapped like he was lesser. “Disobedient, huh? We can’t have that now.”
Before the con artist could react, Mafioso’s large hands found his hips, yanking him forward towards the other side of the desk. iTrapped made a squeak, his legs now on both sides of Mafioso, dangling off the side. The mafia boss grinned, leaning forward.
“Now… since you wanna be all tough on me,” he purred against iTrapped’s ear, “I guess ‘m gonna haf’ta put ya in your place. Ain’t that right, mutt?”
iTrapped made a strained noise in his throat, his breathing picking up. Mafioso tilted his head, one of his gloved hands moving from the smaller’s hip to his clothed erection, palming gently. iTrapped let out an embarrassingly loud moan, his own hand slapping over his mouth in shame.
“F-Fuck…” he whispered, hand muffling his words slightly. “M-Maf, please…”
Mafioso hummed. “Please, what? Use that cute mouth of yours to tell me what’cha want.”
iTrapped whined. He didn’t know how to ask for what he wanted. More than that, he didn’t want to give Mafioso the satisfaction of winning. The larger man smirked.
“You want me to take care of your little… problem?”
iTrapped huffed. “I don’t need your help.”
“Sure seems like ya want it.”
With one last grumble, the con artist’s hands moved to his shirt, undoing his bowtie and vest. Mafioso backed up slightly, as if giving the smaller man space.
“Where’s your lube?”
iTrapped felt his face flush. His mouth opened to respond, but nothing came out. The larger man smiled knowingly.
“I know ya got some, you slut. Don’t gotta be embarrassed.”
“How do you even know we’ll need it?” The con artist scoffed, removing his vest. “W-We might not… do anything.”
The mafia boss chuckled. “You couldn’t take me without it, pet.”
iTrapped went quiet.
“… The drawer under the lamp.”
Mafioso smirked, gloved hand shifting to pet the other man on his head. “Attaboy.”
As the larger man rummaged through the drawer, iTrapped managed to get his shirt all the way off, tossing it on the floor haphazardly. His belt was next, undoing the buckle and tugging it off desperately. His brain felt all hot and foggy, full of anticipation.
A satisfied hum from the other man snapped him out of his thoughts. Mafioso had taken off his gloves, his hand grasping the bottle of lube. He glanced at iTrapped, still smiling.
“Take those pants off, pet.”
Hesitantly, iTrapped undid the button on his slacks, pulling down the zipper with it. There was an obvious bulge, visible even with his black boxers. Mafioso huffed.
“All the way off.”
The con artist whined. “You can touch it just fine like this—”
“Off. Now,” the larger man growled. iTrapped swallowed, tugging off his green slacks in embarrassment. He was completely naked, save for his boxers, which were soon to come off. It was humiliating, especially given that Mafioso had only removed his gloves at this point.
Mafioso approached the desk, eyes wandering all over iTrapped’s bare chest, admiring the sight. “Pathetic. And here you were, thinkin’ you could boss me around.”
“I’m not… pathetic.”
The larger man laughed, but said nothing, like it wasn’t even worth debating over. iTrapped swore he could’ve seen a bulge in Mafioso’s pants before he stepped forward, his large fingers tugging at the hem of his boxers. He wiggled his hips, as if to help the other man get them off faster.
“So needy.” Mafioso tossed the boxers on the floor, taking in the sight of iTrapped’s length. He was so hard, a bead of precum budding at the tip. The mafia boss chuckled.
Leaning forward, the larger man put his left hand on the desk, right near iTrapped’s side, placing the lube nearby. His right hand found its way to the needy man’s aching cock, gripping it slightly as his thumb brushed over the tip.
Immediately, iTrapped let out a breathy moan, eyes squeezing shut in humiliation. Mafioso toyed with the head of his cock a little more before beginning to move his hand up and down slightly. Whines toppled from the smaller man’s mouth, his hips jerking up as if begging for more. Mafioso stopped. iTrapped whimpered in confusion.
The larger man smiled, gaze shifting to iTrapped’s.
“Beg for it.”
The con artist’s face exploded with warmth, a squeak of embarrassment escaping his lips.
“I’m—I’m not fucking begging. How desperate do you think I am?!”
Mafioso deadpanned, scanning the entirely naked smaller man, collapsed against his own desk, spreading for a guy he just hired. The larger man smiled.
“Very.”
iTrapped huffed. He glanced to the side, turning red at even the thought of Mafioso’s eyes on him.
“P-Please… Maf…” he whined, bucking his hips up ever-so-slightly. “Please, j-just touch me...”
“Touch you where?”
“You know where!”
“Ah ah, you gotta use your words, ‘r else you’re not gettin’ anything.”
iTrapped felt himself sigh. “Please… keep touching… b-between my legs…”
“Good. Was that so hard?”
Mafioso’s hand continued jerking up and down, pace slightly faster now. iTrapped moaned out in surprise, tossing his head back against the desk. That climbing sensation had picked up where it left off, his dick weeping precum. He could see it dripping all over Mafioso’s hand… and that did something to him.
It didn’t take much more for iTrapped to climax, ropes of cum shooting from his member and onto his stomach. Mafioso’s thumb brushed over the tip as the smaller one finished, almost entranced by the sight. The con artist flushed.
“How adorable…” the larger man purred, clearly admiring the way iTrapped’s seed had gotten all over himself. “Too bad we won’t be usin’ that cute little dick of yours anymore. ‘S only there to twitch ‘n make ya look pathetic.”
After a moment, he took the lube bottle once again, clicking it open and squirting a sizable dollop on his pointer and middle fingers. The bottle clicked shut. Without much warning, iTrapped felt a cold sensation near his hole.
He whined, a slight growl in the back of his throat as he did. “J-Just put them in already—!”
“Oh, pet,” Mafioso purred. “So impatient. You can’t even handle a little teasin’?”
The tip of one of his fingers slipped inside, only to pull right out. iTrapped groaned in frustration. Mafioso grinned. “Think you’re all big ‘n tough, huh? But here ya are, underneath a guy you hired, beggin’ for him to fuck ya. Don’tcha see how pathetic that is, mutt?”
Holy shit. iTrapped’s cock twitched despite the lack of physical contact with it, an embarrassing noise from his throat giving away his lust.
“All I want’cha to say is ‘please.’ Can ya do that for me, little doggy?”
Fuck. Fine.
“P-Please…” iTrapped pleaded, a whininess in his breathy voice. “Please, Maf, just put them—”
Two large fingers slid in at once, pumping in and out at a rough pace already. iTrapped practically screamed, whimpering as pleasure exploded from between his legs. Each whine and moan had a slight growl to it—something feral that he wasn’t quite ready to acknowledge. Mafioso scoffed.
“Quiet, dog,” he spat. “So fuckin’ loud.”
iTrapped tried to muffle the noises, he really did. But fuck, he’d never felt like this before—so desperate, so out of the usual control he craved, and yet he didn’t mind.
“I said, quiet.” Mafioso took his free hand, the large thing slapping over the smaller man’s mouth. iTrapped shook his head, biting down on the hand just hard enough to sting. Mafioso grunted in pain, yanking his hand away.
“Mother fucker—!” He whispered harshly, adding another finger to iTrapped’s tight hole as punishment. The con artist moaned out. “You think you can bite me like that, fuckin’ mutt?! Gonna have to get a muzzle for you if you can’t behave.”
iTrapped made a noise, cock twitching at the mere thought. Maybe he could tie him up too, put a little collar on, a leash—
“ Shit— I’m so close, M-Maf—!” He whined, his smaller frame tensing.
“Close? You gonna cum from just my fingers?” Mafioso laughed. “Go on, finish all over yourself, pet.”
iTrapped didn’t have to be told twice. Ropes of cum shot from his member as his back arched, one long whimper escaping his throat as he reached his climax. The cum got all over his abdomen, some of it shooting up to his chest. Pleasure flowed through every single one of his nerves, and he shook slightly from the force of it. Fuck, this was so perfect.
After a blissful moment, iTrapped came down from his high, his breathing labored as he stared up at Mafioso through half-lidded eyes.
“M-Maf…?” He mumbled, exhausted. The mafia boss just stared, smiling. He took his fingers out, iTrapped whining at the fullness leaving his hole.
The con artist heard a belt unbuckling, the fumbling of cloth, then the sound of a zipper. He took a breath with anticipation.
“Fuckin’ dog,” Mafioso muttered, his tone laced with barely-controlled rage. “Biting me like that, thinkin’ you’re the boss of me.”
iTrapped stared as the larger man removed his boxers, his erection springing up as it was freed.
Holy fuck.
iTrapped knew it would be big—the guy was massive, for god’s sake—but actually seeing it put its size into perspective. Its length was ridiculous—about 8 inches, not that iTrapped was an expert—but its girth, that was the thing that stood out. A large vein traveled up the side, stopping about an inch below the head. The girth got larger as it got closer to the base of the cock, which a bush of pubic hair sat atop, unshaven. Mafioso had tugged his shirt up, revealing the line of hair that ran from his lower torso to his pubes. iTrapped felt himself drooling.
Mafioso let out a breath, clearly getting just a little needy himself. “Think you can take me? Or do I haf’ta finger you again?”
“C’mon,” The smaller man said with a grumble. “Put it in already…”
“Shut it,” Mafioso snarled, beginning to remove his suit jacket and rolling up his sleeves. “Didn’t know you’d be such a goddamn pain in my ass. Thought you’d just shut up and take it. You seem the type.”
iTrapped felt his dick twitch, face warm with embarrassment. Mafioso chuckled mockingly.
“You like that?”
“… No.”
The larger man hummed, clicking the lube bottle open one more time. He got a hefty amount on his fingers, stroking his own cock lightly in order to distribute it all. Precum was leaking from his tip. He made a breathy noise.
Painfully slow, he lined up the head of his member with the smaller man’s hole, rubbing up and down slightly as if to tease. iTrapped whimpered, hips wiggling in desperation.
“I’m giving ya what you want,” Mafioso said. “Just be patient, my little pet.”
The larger man leaned forward, rubbing his tip up and down one more time. Slowly, Mafioso began to enter the smaller man. Choked moans fell from iTrapped’s lips, like the sheer girth was almost too much. He panted sharply.
“Haahh—it’s— fuck! It’s s-so big—!” He whined. “M-More! Please, Maf, I-I need—”
“Shut your fuckin’ mouth,” Mafioso commanded with a snarl. He continued pushing inside, both of the men moaning with that almost primal growl behind each noise. iTrapped’s tight hole clenched around his cock, so needy for more.
After what felt like hours, the larger man’s dick bottomed out inside of the con artist, twitching slightly in anticipation against his walls. The two men looked at each other for a second.
Without another word, Mafioso began to thrust in and out, his pace slow but not exactly gentle. Each thrust felt forceful, like a little bit of frustration eased out of him with every movement. iTrapped couldn’t get enough—he felt so full , being used like this by a man so much bigger than him. A man who could overpower him without even trying.
“So… so noisy,” Mafioso muttered. “How am I ever gonna shut you up?”
“Mm—Maaafff…!” The smaller man whimpered. “U-Use a muzzle next time! Mmhf, hah, pleeease use a muzzle on me—I’ll be so quiet!”
Mafioso let out a breathy chuckle, his moans becoming difficult to mask. “I-Is that right? Will treating you like a little dog make you behave? Do I, hah , have to train you like one too?”
iTrapped nodded furiously. “Put— hmmf —me in my place, oh god, please! I’ve been so bad—!”
“That’s right, s-so disobedient…”
The pleasure kept building, both of the men grunting and moaning in time together. There was something in the way that Mafioso thrusted that told him he’d wanted this for a while. It all clicked in his head—the way the larger man would seem to hold back around him, the way he’d stare at his hips for just a little too long, the way he’d take pleasure in making iTrapped squirm under his gaze.
The penetration was so much; bigger than anything iTrapped had ever felt before. An outline of a bulge from Mafioso’s large cock was visible on his abdomen, pumping in and out of him. The sight was intoxicating. Mafioso’s fingers dug into iTrapped’s hips, his thrusting more insistent, like he was fucking to prove a point. The con artist felt his body tense, a clear sign he was close. Mafioso caught this.
“You gonna cum for me? Gonna finish all over yourself again?” He taunted, tilting his head. “Well, ‘m gonna finish inside. G-Gonna fill you up, paint your guts white. You like that, pet?”
iTrapped screamed in pleasure, nodding and babbling incoherently. He could almost picture it—Mafioso’s cock ramming into him, filling him with his seed, breeding him—
With a sharp moan, iTrapped climaxed again, eyes almost rolling back as his cum spewed out all over himself, covering a spot on Mafioso’s shirt as well. It didn’t take long for the larger man to finish, thrusting once more and filling his hole from deep inside.
They breathed. Everything felt still.
Mafioso was leaning over iTrapped, his fedora knocked off some time ago. The silence wasn’t uncomfortable—far from that. It felt warm, sweet, almost. It was a foreign feeling to iTrapped.
Mafioso groaned slightly. “I-I’m… gonna pull out.”
iTrapped let out a breath, something almost disappointed, and nodded. Slowly, the full sensation that the con artist had grown addicted to pulled away, leaving the feeling of something warm oozing from his hole. He whimpered. There was so much.
“I—uh,” the mafia boss started, uncharacteristically hesitant. “‘M gonna get you some water.”
iTrapped offered a slight smile, acutely aware of the way he was spread out against the table, cum literally dripping from his hole. “Thank you…” he mumbled.
Mafioso tugged his pants up, redoing the zipper and opening the door to the office. He looked back once more at iTrapped.
“I’ll just be a minute.”
“I heard you,” the smaller man said, a small laugh in his tone. Mafioso smiled, different from his previous grins.
The door shut behind him. iTrapped blinked, staring at the clock on his desk. It was nearly 8:30. Had everything really happened that fast?
The man huffed. He wasn’t sure what to do with himself. He wasn’t sure what he and Mafioso were now, if anything at all.
But for once, he felt the anxiety in his chest ease, just a little.