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Size Matters (or Matters of Size)

Summary:

Nicholas D. Wolfwood, through no fault of his own, has just discovered his cold, calculating, rigid boss has a tiny little pp. How is he supposed to resist commenting on THAT? He had a bigger dick before he even had an official dick!

Unfortunately for Nicholas, Nai knows exactly how to make him eat those words.

Notes:

Prompt:

 

Not particular about the ship or dynamics, but I want someone with a tiny cock compensating with a massive strap to choke someone on. He makes the bottom worship and swallow down a massive strap while he gets hard and gets off underneath. I want the top getting off on finally having a big dick, and also absolutely humiliating the bottom with it.

Bonus:
+Cock warming the tiny pp beforehand
+The person choking on the strap comes from having their own dick stepped on
+Asphyxiation, with tiny pp man grasping around where bottom's throat bulges

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The second I saw this prompt I knew exactly what pairing I was writing it for. Nai deserves an itty bitty microdick.

I did a lot of research on the possibilities of phallo for this fic because I am a cis woman and I wanted to see what options Wolfwood might have access to in this universe. So for the purposes of this fic, Wolfwood has had what’s called a VPP (vaginal-preserving phalloplasty) because he seems like the kind of guy that would think something like “as long as I don’t have to deal with PMS bullshit, getting fucked feels nice. So I’d like to keep the pussy but I still want a dick.” He seems like the kind of guy that likes having options, you know? Also when I mentioned my research to my very not-cis partner, they immediately said “Man, if I ever got a dick, that’s what I would do,” which felt pretty validating.

So for the purposes of this fic, Wolfwood’s junk includes a dick, for which typical language is used, and a vagina, for which typical language is also used. His phallo is the kind that includes clitoral burying, because that can give more sensation in the penis, so he does not have a clit. He also does have the implant that allows him to get hard and he has good sensation in his dick (meaning he’s at least a few years out from his procedures and didn’t have any complications with nerve reattachment). He’s rightfully very proud of it.

(See the end of the work for more notes.)

Work Text:

Nicholas rapped on the heavy oaken door before him. He was approximately twenty minutes late for his meeting with Millions Knives. Before arriving he’d swung by the Starbucks down the block and gotten the blackest, boringest coffee he’d ever ordered from a chain famous for its frilly sugary monstrosities. He’d bypassed the newest version of Nai’s blond-haired, blue-eyed secretary Barbie at the front desk without giving her a chance to do her job and announce him. For anyone else, this level of disrespect would earn them a date with the barrel of a Punisher and a shiny new pair of cement shoes, but Nicholas had been getting away with worse for years. Hell, he would only ever call Nai ‘boss’ in front of the other Families,unless he was in trouble, which he might be right now.

His last mission had been a bit of a shitshow, to say the least. He’d gotten away with the data he’d needed, but he’d been forced to leave a pile of bodies in his wake—a nice little trail of breadcrumbs that would lead anyone even slightly savvy to the Punisher’s methods right to Nai’s doorstep. The coffee bribe seemed necessary here. Nicholas was going to be testing the limits of Nai’s soft spot for him today. He’d even gone so far as to leave his signature weapon behind, in the hopes the missing bulk would make him look less threatening. Less like a problem that needed to be dealt with.

“Come in,” Nai’s voice was barely audible through the thick wood of the door.

Nicholas swallowed any lingering nerves about how this meeting might go and plastered on his best suave smirk. He was gonna have to charm his way out of this one.

He found Nai sitting behind his massive executive desk, a file in front of him and his fingers steepled under his chin. Icy eyes tracked Nicholas’s movements like a predator tracking its prey. Without so much as a howdy-do, Nicholas strode across the room and plopped the coffee down on one of Nai’s fancy gilded marble coasters.

“Take it you heard about the Octovern job, boss.”

Nai said nothing.

Nicholas did his best not to squirm where Nai could see. “Shit, got out of hand. Bad luck the guards decided to do their rounds early so they could catch the start of the game.”

One white-blond eyebrow raised in a delicate arch. “Bad luck?”

Nicholas recognized the dangerous water he was treading in here. “Predictable, if I’d had more time to case the place. But you did say you had a deadline.”

The second eyebrow joined the first. Maybe not the best idea to blame the boss for his failure.

With inscrutable calm, Nai picked up the coffee Nicholas had presented him with. He took a sip. Nicholas folded his hands behind his back and waited for Nai’s verdict.

“I’m getting tired of cleaning up your messes, Nicholas.”

A cheeky comment—one that would almost definitely get him shot—rose to the tip of Nicholas’s tongue. He bit it back.

“It won’t happen again, boss.”

“Be sure that it doesn’t, or next time you’ll be on your knees begging for your life.”

Nai took another long sip of his coffee. Nicholas couldn’t help himself this time.

“That a threat or a promise?”

Nai choked on his coffee. Time froze around them as Nicholas perceived the incoming disaster caused by his own damn mouth. Those long fingers tightened around the flimsy paper cup in his hands. The lid, utterly useless in the face of Nai’s shock, popped right off the top, and hot coffee splashed into the lap of the most notorious criminal overlord in the city.

Nicholas saw his life flash before his eyes.

The office exploded into a flurry of motion. Nai shoved back his chair and stood. Nicholas leapt forward to grab at the falling cup. He managed to save half of it, sloshing more hot liquid across Nai’s desk. In a near-panicked rush, Nai undid his belt and slid his steaming pants off his thighs and onto the floor. 

Nicholas set the half empty cup back down on the desk slowly, like minimal movement might save him from Nai’s inevitable wrath. Seeking something, anything, to distract the fury he could see burning into those terrifying blue eyes, Nicholas’s gaze landed on a pair of blinding white but impeccably toned thighs. Thighs that Nicholas had ogled on more than one occasion.

Sue him, his boss was hot. It wasn’t like he’d never caught Nai staring at his ass before. He was pretty sure he knew the reason he got away with so much more shit than other Punishers.

Those thighs led up to a rather plain pair of boxer briefs. Nicholas’s dumb horny instincts got the better of him once again, and his eyes tracked to where the bulge of Nai’s considerable package should have been.

For a split second, Nicholas could only blink in confusion. He could have sworn Nai was a cisgender man, unlike Nicholas himself. Where he expected to find a bountiful feast, instead he found a little lump that instead looked like Nai had stuffed some paper down his pants in lieu of an actual packer. 

“Where’s your dick, dude?”

God.

Nicholas was going to die tonight, and he would deserve it.

The anger in Nai’s expression flared into rage. Nicholas backed up and put his hands in the air.

“Shit, sorry. Ignore me, boss.”

Nai took a deep breath. His face closed off into an alarming blank mask.

“Do not ask questions you can’t answer for yourself, Nicholas,” Nai said, all cold fury and burning gaze.

A few years ago, before Nicholas’s surgeries, he might have balked at a question like that. It was meant to cut, designed to dig into the vulnerable places in Nicholas’s chest. Nai always became the embodiment of his moniker when he was truly angry. Millions Knives, indeed.

A truly, genuinely, idiotically insane idea popped into his head.

Well, if Nicholas was headed for a midnight dive while tied to Angelina, he might as well show it off.

“Wanna see?” he asked. Then before Nai could answer or he could overthink, Nicholas undid his belt and dropped his slacks and boxers to show off his thick, heavy cock.

He’d worked so damn hard for that thing, it truly seemed a shame if no one ever got to appreciate it. It wasn’t like Nicholas was picking up one night stands anymore. Not since he’d started working directly for this bastard.

Nai, for his part, eyed Nicholas for a moment, his anger apparently dissipated. Then simply turned away to step fully out of his own pants. He bent and picked them up to inspect the stain, his back to Nicholas. A clear dismissal, and one that meant Nicholas might live to fight another day.

Now that wouldn’t do.

“Hey, ever heard of reciprocation?”

“You hardly gave me a chance to answer your question. I’ve no interest in seeing your penis.”

Nicholas snorted at the dry delivery. Still, he almost liked it better when Nai had been furious at him. Then, at least, he’d been the sole focus of Nai’s attention.

Nicholas refused to interrogate why he wanted that attention so badly. Especially right now, with his dick out and a strange swirl of anxiety and anticipation rising in his chest.

Nicholas’s mouth kept on moving of its own accord. “What, you don’t want to show it off? I thought that was a thing guys loved to do? Or do you have a pussy? I got one of those too. We can still compare.”

Nicholas could see the way Nai’s eyebrow twitched, even with his face angled away.

“C’mon, I showed you mine,” Nicholas goaded, not even sure why he was still pushing.

Nai jerked around to face him so fast Nicholas flinched. In one fluid movement, he ripped his prissy black boxer briefs down to show off…the tiniest cock Nicholas had ever laid eyes on.

Maybe he was a grower?

Pity flooded through Nicholas. He attempted to keep the feeling off of his face. He was pretty sure he could have won this dick measuring contest before his phallo.

“That’s it? Pretty sure my clit was bigger than that before the doctors gave me this.”

Nicholas had no idea what was coming out of his mouth anymore. He hadn’t intended to give voice to the stupid thoughts in his head. The half-pitying, half-goading tone was certain to get some kind of reaction, and even Nicholas wasn’t sure what he was aiming for.

The last dregs of calm drained out of Nai’s face. Between one blink and the next, he’d gone from behind his desk to in front of Nicholas. Before Nicholas could so much as draw a breath, Nai had grabbed him by the lapels of the jacket he was still wearing and slammed him backwards into the nearest wall. His head banged into the drywall.

“I don’t need a big cock to make you see stars,” Nai snarled.

Nicholas was already seeing stars. He grinned at Nai, all teeth.

“Yeah? Prove it.”

Nai’s forearm came up to block Nicholas’s windpipe. Nicholas wheezed.

“Can you get hard?”

He supposed that was a valid question. Unable to form words, spots and pinpricks of light dancing before his eyes, Nicholas nodded.

Nai let him go. He gasped for breath.

“Take your clothes off.”

Nicholas had never obeyed one of Nai’s orders so quickly. 

Nai eyed him up and down, blazing fury once again replaced by eerie calm. Nicholas didn’t know what to make of the mood swings.

“Get yourself hard for me.”

Nicholas flushed. Humiliation burned in his chest as he wrapped his hand around the base of his cock. Nai was eying him like a specimen under a microscope. He wanted to squirm out of his skin.

He wanted Nai to never stop looking at him.

Nicholas gave himself a few long, slow strokes, shuddering at the feeling of the sensitive nerves alighting under his hand. He’d once feared he’d never recover sensation there, but now, years down the line, he reveled in the feel of his own dry hand as he tried to give Nai a good show.

Nai, for his part, gave nothing away. He may as well have been watching a particularly boring nature documentary. After a few minutes of working himself to hardness (Dry, he might add. Nicholas vaguely wondered if Nai would be disgusted or turned on if he dipped his fingers into his own pussy for some natural lubrication, since he couldn’t exactly produce it with his dick) Nai raised his wrist to check his watch.

“I have a meeting in ten minutes. Get under my desk.”

Nicholas blinked at him, “What?”

“Under the desk. Or leave.”

Whelp. Under the desk it was.

Nicholas took one step in the direction of the desk. He was stopped by a large hand tangling roughly in his hair. Nai shoved and Nicholas went down to his knees without a fight.

“Crawl.”

Fuck.

Nicholas’s entire body burned with shame. Slick started to gather between his folds and leak down between his thighs. His hard cock hung heavy between his legs as he shifted himself onto hands and knees, unable to keep himself from rubbing them together. Even with his dark complexion, Nicholas was certain that his flush extended to his peaked nipples. He angled himself to give Nai the show he wanted, flaunting the weight of his cock and the place where the base met his wet slit. He could feel Nai’s eyes on him as he made his way across the room to the desk. His unwavering gaze stoked the fires of lust and humiliation into a bonfire, blazing under every inch of his skin.

He had never been grateful for Nai’s giant fuck-off executive desk until that moment. The space under it, even when Nai sat down in his chair, had plenty of room for Nicholas to settle on the plush carpeting. The full length of the heavy wood sank all the way to the floor on all sides, rendering Nicholas completely invisible to anyone else in the office.

Nai spread those thick thighs and gestured to the space between them, “You have five minutes to get me hard. When my meeting starts, you will not move or make a sound. Be good, and I’ll consider giving you a reward.”

Fuckfuckfuck.

Already cock drunk and hazy, Nicholas scooted forward into the juncture of Nai’s open legs. He wrapped two fingers around the miniature dick in front of him.

It was actually kinda cute up close.

He stroked his fingers up and down the sides like he would have back when he was getting his t-dick warmed up. It twitched under his touch, but a quick glance at Nai’s face revealed no reaction. Nicholas rubbed his thumb over the head, gathering the wetness starting to form there, and eased his fingers back down the length. Nai hardened rapidly, but really didn’t get all that much bigger in Nicholas’s hand. He kept stealing glances at Nai’s face, but he was met with an impassive mask every time.

Fine.

Nai’s size meant that he had to nose in close to Nai’s groin to wrap his lips around the little shaft. This close, his heady, musky scent overwhelmed Nicholas’s nostrils, deeply masculine for all of Nicholas’s jokes and teasing. He easily buried his nose into the white-blond curls at the base, no need to control his gag reflex or take his time to take him all the way down. The weight of it was nothing like the fat cocks he’d most often blown in the past. Before this exact moment, he might have even identified as a bit of a size queen, but Nai’s cock was doing it for him. Or maybe it was just Nai. 

Nicholas suckled at his mouthful, swirling his tongue, and smirked when he heard Nai’s sharp intake of breath at his ministrations. The salty, bitter taste of precome drowned out the lingering flavors of coffee and cigarettes as he moved his mouth without bobbing his head. He didn’t need to.

A knock at the door startled Nicholas so badly he almost hit his head on the bottom of the desk. Nai’s hand fell into his hair and locked him in place, lips still wrapped around Nai’s cock.

No more moving. No sounds. He could do this.

Nicholas shifted into a more comfortable position and froze, Nai’s cock resting, light and comfortable, on his tongue. The grip on his hair eased slightly.

“Come in.”

Oh god, Nicholas really really hoped he could not be seen from the other side of the desk.

“You wanted to see me, Master Knives?”

Fuck. Legato.

Anxiety tightened Nicholas’s chest. Only the comfort of Nai’s weight on his tongue and hand in his hair eased the feeling.

Be good, Nai had said.

Nicholas breathed slowly through his nose and tuned out the conversation happening above him. Instead, he focused on the salt of Nai’s skin, the heady musk between Nai’s legs, the idle movement of Nai’s fingers through his messy curls. Saliva gathered in his mouth and he swallowed around Nai’s cock.

He drifted, letting all thoughts float away in favor of sensation. The murmur of voices became background noises, muffled as if Nicholas was sinking below water. His eyes fell halfway closed, his vision filled with blond hair and pale skin.

A nebulous calm had settled over Nicholas by the time Nai’s hand tightened in his hair enough to pull him off of Nai’s cock. He blinked, unaware of what had changed.

“He’s gone. I suppose you did an adequate job of keeping me warm.”

A shiver worked its way down Nicholas’s spine. A large hand cupped his jaw. Nai ran the pad of his thumb over Nicholas’s bottom lip, before pushing the tip of it inside. Nicholas lapped at it, already missing the taste of Nai’s skin.

“Since you were good, I suppose I can show you why size doesn’t matter.”

Nicholas nodded eagerly, a thrill running through him at the words you were good.

Nai rolled his chair back from the desk and reached down to unlock one of the lower drawers. He pulled a bundle out of it that Nicholas couldn’t see. Nicholas stayed exactly where he was—Nai hadn’t told him he could move—as Nai got up and walked across the room.

The schnick of the office door locking echoed in the silence of the room. Clothing rustled beyond the desk, but Nicholas didn’t dare move without permission.

“Come here.”

He scooched his way out from under the desk. Even with the lavish carpet, his knees were starting to burn. He still didn’t stand.

Nai stood, naked but for his fancy leather shoes, across the office with the smuggest expression Nicholas had ever seen adorning his face. A dildo well beyond any human proportions jutted proudly from where it had been secured at his hips. Nicholas’s eyes widened. Nai stroked it a few times, his hips rocking forward into the pressure of the strap.

“I told you to come here, Nicholas. I will not ask again.”

Christ Almighty, Nicholas could have sworn his soul was trying to exit his body through his pussy. Or his cock. One of them. Or both, probably.

Nai, cold and gloating, flat and excited all at once, was the most terrifying yet most beautiful thing Nicholas had ever seen.

He crawled forward, unable to be self-conscious this time with his eyes glued to the massive cock Nai was now sporting. Like everything in Nai’s office, the dildo was clearly expensive. It fit snugly into the strap as though it had been custom made, powder blue with white swirled through the silicon and a shiny, pearlescent finish. The shape was at least human, not one of those dragon or horse insanities like some of the ones Nicholas had discovered in his shameful online perusals. It was human, but a bit like a mountain troll had gotten his cock chopped off to be used for Nai’s intense, gleeful pleasure instead.

Nicholas settled himself at Nai’s feet.

“Good boy.”

Nicholas shivered.

Before he could bask in the praise though, a harsh hand threaded through his hair and roughly yanked him down to kiss the tip of Nai’s cock. Obediently, Nicholas opened wide and wrapped his lips around the head. Nai gave him no chance to adjust. His hips rocked forward, thrusting the gargantuan length into Nicholas’s throat with no warning. Nicholas choked. Nai laughed.

“You want a big cock? You better be able to take it.”

The absurd image of his own obituary flashed behind Nicholas’s watery eyes. Nicholas D. Wolfwood, asphyxiated on a mammoth dick.

What a way to go.

Determination and desire drove Nicholas down on Nai’s strap. He could only take it’s length about halfway at first, but he kept trying. He relaxed his throat, making no attempt to stop the next thrust of Nai’s hips. His lungs screamed for air, but he ignored them. Tears clung to his lashes, but he ignored them too. He knew only how to take what he was given, and give as much as he could back. He was convinced Nai was about to rip out chunks of his hair, but the pain hurt so good in tandem with the stretch of his throat.

Through the spots dancing in his vision, Nicholas noted the growing wet spot where the dildo met the harness. Nai was certainly enjoying himself.

Nai bent forward. The hand not in Nicholas’s hair wrapped itself around his throat and squeezed.

“That’s what you wanted, huh? To choke on my cock? Do you think you could take this? Would that greedy cunt of yours suck this in? Would it hurt? You’d feel this for days, for weeks. Think size matters now?”

God.

He could feel the movement of Nai’s cock through his throat against the grip of Nai’s hand. Nicholas rocked his hips. His hands scrabbled against Nai’s thighs and ass, looking for some kind of handhold. His soaking pussy clenched on nothing, his cock finding no friction in the empty air.

Nai shifted his stance. Like a gift from a benevolent god, one of those fancy leather shoes—shoes that had to be made by an actual cobbler and probably cost more than everything Nicholas owned—came forward to press hard against Nicholas’s erection.

Nicholas came in a gush of fluid, tears streaming down his face, his broken cry lost against the dildo down his throat.

He must have blacked out for a few seconds. When he came to, he’d been laid out on Nai’s office couch, and Nai was standing next to his head, his large hand moving furiously over his tiny erection, the monster cock pushed off to one side. Seeing what was coming, Nicholas just barely had the wherewithal to open his mouth and close his eyes.

Streaks of hot come painted Nicholas’s mouth and face. Nai may have been small, but he came as much as anyone else. Nicholas swallowed what he was able, licking his lips. He blinked his eyes open, lucky they were clear of fluid

For a few moments, Nai loomed over Nicholas, panting. His eyes greedily devoured Nicholas’s prone form. Nicholas fought not to hide in response.

Then, without a word, Nai turned and walked to his attached bathroom.

Nicholas’s heart dropped through the floor. He pushed himself up on the couch. Panic tightened his chest and restricted his breathing, in a much less fun way than moments before.

What if Nai hated him now? What if he was about to meet the business end of one of those famous, stylized knives?

Nai stepped back out of the bathroom. He took one look at Nicholas and crossed the room in a few long strides. His hand came up under Nicholas’s chin, angling his head back. In his other hand, he held a wet washcloth. He ran it gently over Nicholas’s face, cleaning away the mess.

“You did well. Now be still for me.”

Nicholas sagged forward into Nai like a puppet whose strings had been cut. Nai huffed, but he maneuvered Nicholas back onto the couch and knelt so he could get between Nicholas’s legs. He cleaned there thoroughly as well.

“Next time, I’ll put my cock inside you.”

“Which one?”

He sounded like he’d been gargling sandpaper.

“Wouldn’t you like to know?”

Nicholas giggled. Nai petted a hand through his hair, gentler and sweeter than Nicholas ever would have expected from him.

“Sleep. You have thirty minutes before I need to get ready for my next meeting.”

Uncertainty tightened Nicholas’s chest again. He reached up and put a hand on the back of Nai’s neck, tangling his fingers in the base of his blond hair and dragging him down into a kiss.

Nai kissed him back.

“I expect to see you at my home tonight. Eight o’clock sharp. Do not be late this time,” Nai murmured against Nicholas’s lips.

The last dregs of anxiety drained out of him.

“You got it, boss.”

“Shut up and go to sleep.”

Nicholas offered Nai a tired thumbs up and snuggled into the lush leather cushions. In minutes, he drifted off.

Notes:

Nicholas D. Wolfwood, walking in 20 minutes late with Starbucks: Yo, boss, did you know your dick is small?