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The morning went on without a hitch, or at least Shizuo doesn't have to dangle someone over a five-storey building so that they would be more cooperative for the day. Surprisingly, it only takes a scowl from Shizuo, a little bit of fist shaking, and Vorona listing off different torture methods should their 'target' decide to me anymore difficult to handle than they ought to be, to get the morning's work done. With three people out of the five they had to rattle into opening their wallets, they head for a café to take their usual break. Tom reckons it's one of those special days, when he doesn't haven't to worry about collecting money from corpses, as they head towards a nearby eatery for their lunches, and his two co-workers fell behind him at the prospect of food. They settled down in the small café, a familiar waitress quickly coming to take their order.

"Anything special for you guys today?" She said with the usual cheerfulness, holding up a piece of paper and a pen to take their orders.

"I think we'll take the usual, Himiko-san." Said Tom, more than used to ordering, but he gave the two a look as he normally did. The two blondes nod in agreement, much like two puppies too entranced by the thought of food to argue.

"So that's a large strawberry milkshake. a slice of red velvet and a slice of chocolate fudge?" Himiko supplied, already scribbling down on her paper.

"Yes, thank you."

"I'll be right back with your orders."

With that, she left the trio to their own company. Which isn't much to be expected as the two bodyguards seem all too fond of keeping quiet and speaking only when spoken to. Tom busied himself with rechecking the two addresses they still had to go to. With how dangerous some of the men were, it wasn't a surprise to see that they lived in the 'bad side' of Ikebukuro, where crime was higher and disappearance weren't even batted an eye at. Not that he was worried, certain that his two bodyguards were more than capable of protecting themselves and him no matter the situation. But still…

Himiko returned with their orders, placing down a large glass of pink shake for Shizuo, a slice of red velvet for Vorona, and a chocolatey slice of fudge for Tom, saying a well-worn. "Enjoy" as she rushes back over to the counter.

Shizuo leaned forward, taking the straw in his mouth to enjoy his drink. The rush of cold sweetness was welcomed, and he closed his eyes to savor the taste of it, until a shrill ringing sounded out. He grunted, pulled out his phone, and a big and bold 'ONE NEW MESSAGE' on his screen.

[ Can I cum over later? ;) ]

Fucking Masaomi.

[ Do you really have to ask like that? And yeah, you know you're always welcome. ]

He sent the message, pocketed the phone and made to drink his strawberry milkshake. Until, not even a one minute after he replied, he felt his phone vibrate in his pocket, not to mention the shrill beep that came with it. Whipping out his cellphone, he glared at the screen.

[ Yes, I actually do. It's part of the package. I'll cum around 8, and remember it's my night tonight. ]

He wasn't even going to grace that with a reply, quickly pocketing the phone, and resumed with his milkshake. He raised a brow at Vorona, who looked at him questioningly.

"Did your electronic device offend you, sempai?"

"Ah, no, it was a text from-" Kida? Some kid? A fuck buddy? "a stupid friend." He finished with only a short moment of hesitation. He saw a fleeting look on Vorona, as if she wanted to question further, but thankfully Tom interjected. "Oh that's nice, you should really start taking some of your day offs, they've been racking up you know, spend some time with your friends too." Shizuo shrugged nonchalantly, focusing on his milkshake a bit more. Considering he had so few friends, and his previous days off were either spent with his brother or alone, taking day offs were more of a bother than an actual vacation. He liked to be kept busy, and sitting idle at home didn't sound too appealing.

The rest of the day goes on without much incident. They manage to talk, or at least Tom does the talking, one of them into paying half of what he owed, with the promise of the second half in a couple of days. In Shizuo's opinion, they would wrung the man dry, were it not for a small child who had run out from inside the house, clinging to the leg of her 'daddy'. They left with only a small warning of what could happen if he didn't hold up his end of the bargain. And then apparently the other punks wasn't even home, but they left a very pleasant message for him when he did come back, along with a broken door to fix. A reminder and a threat.

Shizuo made it home a few minutes before six, and he immediately goes to the microwave to heat up a meal. He dug into his meal in utter silence, chewing down the dry beef and rice. Someday, he swore, he'd actually cook food half-way decent, but for now he's happy enough with something he bought from the convenience store for the moment.

With eight still so far away, he figured taking a short nap would do him some good, and maybe he wouldn't snap so much at Masaomi when he does cum over. He groans at the memory of earlier as he lays on the bed, glad that he managed to keep himself in check and NOT crush his phone right then and there. With that thought in mind, he drifted off to sleep.

Masaomi snickered as he closed his own phone. No reply from Shizuo just meant that, yeah, the man was probably not as amused by his hijinks as he was. Which didn't bother him at all, no. Once he figured that Shizuo had some of the most surprising reactions to a bit of perverted talk outside the bedroom only meant that he had to take advantage of it every chance he got. Course, he hadn't tried to sext with the man yet, he figured it would get him a real kick to the ass, but…. Soon. Quite soon.

The thought of an embarrassed Shizuo was almost enough to make him forget about what he was about to do. Almost, but not really. The only reason he even texted the blonde was so that he could get through this meeting.

Riding the elevator up to the top floor of the building, he breathed in and out, mentally telling himself not to rise to any bait that was sure to come, or answer back too much with anything his employer could use. The less talkative he was, the better.

He knocked on the expensive looking door, and a moment later was greeted by a woman in green turtleneck sweater. She looked him over, scoffed and stood aside to let him in. Ah, well, it wasn't like he and Namie, Izaya's secretary, ever saw anything eye to eye anyway. He had long given up trying to be her 'friend', not after she had tried to make Mikado's life miserable, and maybe the only thing they had in common was that they both hated working for Izaya.

"Izaya, Kida-kun's over here." She called, already turning her back on him to return her desk.

And just like that, Izaya rolled backwards on his chair into view, leaning back and smiling at him as if he was some welcomed guest. "Ah, Kida-kun, on time as usual, I had a question to ask you. Into my office now." He finished a tone of politeness, already moving back into the room with a roll of wheels.

Masaomi rolled his eyes. No matter how much Izaya sounded nice, he could tell from the glint in his eye that he wasn't going to enjoy this particular session. But he sucks up that feeling and deposited his school bag onto the couch, and enters the office.

Izaya stared at him for a moment, calculating red eyes scanning him over. And he can just feel it settle on the bruise that Shizuo left on his neck last night. The man never asks about the bruises though, seemingly accepting it as a natural thing, for which Masaomi is grateful for. If he has to explain ever mark, then it would take quite some time and nerve.

"How likely do you think Shizu-chan would accept a rendezvous outside his home with you?"

Masaomi blinks at the question, wondering where it had come from.

"Uhm… I guess it would depend on his convenience?"

"You guess, Kida-kun? Four months of being around him, and you guess?"

There was disappointment in there. Uh oh.

"He has a job, I don't think he'd just take a break for a meet up."

"But wasn't that what I told you to do in the first place? Do I have to remi-"

Masaomi huffed, quickly cutting the other off. "Yeah. Get close to him. Make him need me. I remember that. Thank you."

"I even gave you the hint to have sex with him, neh, Kida-kun?"

At this point he couldn't hate the man any more if he tried. It started with a deal. With a prize he couldn't resist.

Ten million yen and his freedom.

The money was a mere bonus, what he truly wanted was the promise of Izaya finally leaving him alone, never to bother him with whatever bullshit he had to going on for me. He would owe no favors, everything would be settled with it. He was past the point of return, and he could only see the plan through. Though in his defense, he didn't think that Shizuo Heiwajima of all people would be one to trust someone so easily and let them into his home. He had expected more resistance, not to be greeted with surprising compliance and gentleness.

"Yes, oh thank you, great Orihara Izaya for that wonderful tip." He said in a loud voice, sarcasm overflowing.

"Mmhmm. Consider yourself lucky that I'm not asking for details, Kida-kun~"

Which was another thing that had bothered him. Izaya, being the bastard that he was, it was sort of given in Masaomi's mind that that would have been the first thing Izaya would have asked about. It would mean perpetual embarrassment on his part, plus that was something to prod Shizuo with, wasn't it? But surprisingly, week after week, the man hadn't asked a thing about the sex. There were countless questions about Shizuo's home, his eating habits to how many times he smoked cigarettes. But never about when they were in bed. Course, Masaomi didn't bother asking about it, comfortable that he was not asked that, thank you very much. As much as he'd like to brag, giving a blow-by-blow to Izaya was creepy as fuck.

"Sure, okay. Is that all?"

"You're meeting him tonight."

It wasn't even a question.

"Well yeah, I wanna get this over with as soon as possible, and the closer I get to him, the easier it'll be to give you want you want, right?"

"Diligent as always, Kida-kun." There was sarcasm there, Masaomi was sure, even if Izaya did a terrific job hiding it. "Very well, off you go, wouldn't want to keep you from a date with a monster."

"You hired me for this." He supplied back, before leaving the room as quickly as possible, rushing past Namie and he was gone.

8:13pm

It wasn't a problem. Part of Masaomi always noted how careless it was Shizuo lived. For a man who had many enemies, whether he liked making them or not, he certainly showed that he barely cared about the security in his home. Unlocked doors, open windows, though that was probably to alleviate the permanent smell of cigarettes than actual carelessness, but it proved his point. It was too easy to get in and get out, though there wasn't much to steal, that was for sure.

He flopped in through the bedroom window, trying to be quiet as he could as he practically fell on the floor with a groan. Picking himself up, he froze as he realized what he had dropped into.

Shizuo on the bed, spread eagle. Bartender suit still on, though his tie was gone and a few buttons of his dress shirt were already undone. Sleeping so peacefully. Masaomi had to blink a bit. He didn't think that he was too late, and with how deeply the man was breathings, he guessed that Shizuo had gone to sleep before eight. He had two options of course, wake up the man and get on with it or… Surprise him altogether.

It wasn't even that hard of a decision.

He smiled to himself, dropping his bag on the floor as he slowly crawled on the bed, staring intently at Shizuo. The sleeping man didn't seem to care, and continued his slumber as the boy positioned himself between the man's legs. He worked on the man's belt buckle, unbuttoning the pants button, and cupping the flesh just beneath boxers.

Still, the man didn't move.

He massaged lightly, kneading the flesh as it slowly hardened. Impatient, he pulled on the pants and boxers, just enough to uncover the forming erection from it's confines and took a hold of Shizuo's cock, stroking it. At that, the man started to squirm, grunting and moving around his bed as he slowly awakened. A look of glee on his face, Masaomi pumped Shizuo roughly, watching as the other man opened a blurry eye at him, obviously holding back a moan as his lips formed an 'O'.

"Masaomi." Shizuo said in recognition, breathless from either sleep or arousal, Masaomi wasn't sure. But damn, that just made him shiver in a good way.

"Yeah, who else could it be."

He could see Shizuo struggling between his mind and body. While the cock hardened in his hands hardened as he pumped, there was a disgruntled look on the older blonde's face, as if he didn't know if he should be annoyed or happy about being woken like this. But Masaomi was determined to show him it wasn't all that bad. He brought a thumb over the head of Shizuo's erection, swiping over the slit, spreading the formed pre-cum over the head. Another held moan that did delicious things to his body.

"The fuck are you-"

"What do you think, hmm? I told you. It's my night." He cut the man off with a rough stroke, enjoying the bit of power he had. It would be short-lived, he knew that, which only meant he had to prolong it for as much as he could.

"Ahhhn." Was all that Shizuo managed to reply to that, staring at him in a haze of lust that was similar to his own, compliant for now. He could feel his body heat up further, the bulge in his pants twitching at that thought. How compliant, he wondered.

"Take off your shirt." Masaomi said, glad that his voice didn't waver.

Something flashed in Shizuo's eyes, a glint of pride and dignity, and for a moment, Masaomi thought for sure Shizuo wasn't going to punch him. A moment passed, Shizuo's hand moved slowly towards himself, undoing the remaining buttons and moving out of his shirt as he bared his naked torso for him to see. Masaomi sucked in a breath at the sight for him, lines of hard muscle on the man's abdomen, arms so strong, yet they only featured defined lines that weren't even close to showing how much strength the man actually had.

Masaomi blinked at the silence, not sure how long he'd been staring, but Shizuo was staring back, something of a challenge in his eyes. Not that kind that he had when he was fighting off thugs, not the kind when the police had caught him, but it was the one that Masaomi had become accustomed to. How much are you going to push? And it wasn't a question he was comfortable with.

"I don't think, you're awake enough yet." He said playfully, stroking one more time, before leaning down.

"Wait! What are you-"

Shizuo groaned as Masaomi took his cock in his mouth, the sudden warm wet feeling around his cock sending blood straight downwards. He could feel those lithe fingers on the base of his erection, though it was more of an afterthought, squeezing and stroking lightly as the boy sucked, the usual noisy tongue pre-occupying itself with tracing under his cock, teasing just beneath the crown before swiping at the slit, only to do it all over again at the next bob, effectively driving out any thought Shizuo had. Before he knew it, his fingers were threading into those blonde locks, his hips were thrusting upwards into that delicious mouth, inching his cock further into the willing heat.

Masaomi choked a little at that action, jaw moving to encompass more of the man's cock into his mouth. He curled his tongue on the erection, earning a groan and tightened grip on his hair. He took it as a good thing. With his free hand, he unbuckled himself, relief as his own dick was finally out of it's confines, hard and proud. He pulled away, panting as he did, fumbling into his pockets.

He heard an impatient groan, and the man shifting around in the sheets, but paid no mind as he searched himself for the usual packet of lube. That was until something bumped onto his head, and he was greeted with the sight of Shizuo holding out a bottle of lube for him. Masaomi grinned sheepishly, accepting the bottle and coating his fingers with it before practically throwing it to the side.

"Oy, I actually go out to buy and you ahhh mistreat it." Came Shizuo's complaint, mellowing down as Masaomi took his cock into his mouth once more, adding a teasing flick to the tip, the taste of precum on his tongue, as the only thank you he'd be replying with. He reached behind himself with his own slick fingers, encircling his entrance as he moaned and shuddered under his own teasing. Which caused delicious vibrations on Shizuo's erection, the older man's eyes fluttering at the sensation.

As much as their sex was going, they hadn't bothered trying to switch positions. There had been a whole five minute discussion, wherein Shizuo made the analogy of a Corgi trying to take a Great Dane, which then led to a rather strange talk about dog sex and evolved into doggy style. Shizuo hadn't been able to talk about dogs without feeling embarrassed ever since. At least he felt that Masaomi had gotten the point of the whole stupid talk, and even this situation, with the boy technically on top of him, he trusted Masaomi enough to think that he wouldn't even try. Though what would happen by the end of the night was definitely on Masaomi's hands.

He finally breached the tight ring of muscle, pressing a finger deeper inside himself as he squirmed to the feeling. It was no different than having Shizuo do it, albeit a bit more exciting when he didn't know what he would do next. The sensation was the same, as he eased into the feeling of being stretched, the lube helping with slicking himself up for later. He added another finger, and another, scissoring himself open, as he thrust back to his own fingers, trying to curl and pry himself open for something much larger. It wasn't until Shizuo gave a light impatient thrust into his mouth did he realize that he had been too busy with fingering himself that he had stopped any movement with his tongue. He let the cock pop out of his mouth, lewd as a mix of precum and saliva dripped down. Starting from the base, he pressed his tongue onto the length, licking up to just beneath the crown, teasing the skin beneath as he held the cock steady with one hand, taking it into his mouth again while he continued to fuck himself with his fingers still deep in his ass.

It didn't take long until he was felt he was ready. Withdrawing his fingers, he shifted around in the bed, panting as he moved himself higher. Shizuo remained on his spot, already guessing what they were going to do, licking his lips and eyes darkening at the thought of it. His hands quickly took purchase on Masaomi's thigh as the boy position himself just above his cock, aligning his ass onto the waiting erection. Masaomi moved down slightly, Shizuo groaning as the tip of head met with the hot shuddering hole just above it.

"You drive me insane." He growled out, stopping himself from just thrusting into the heat presented to him, stopping himself from just pulling Masaomi down and impaling him onto his cock.

"I guess I'm just special that way." Was the breathless reply, a chuckle, before he felt the boy move. No finesse, Masaomi let gravity do it's work. The stretching he had done wasn't enough to erase all the pain that was to be expected, but enough to make sure that the cock would slip in easily enough. He sat himself, barely aware that his ass had met Shizuo's thighs as he focused on breathing and getting used to the feeling of being stretched so much in this position. Was it him? Or did Shizuo's cock just get bigger? Maybe. Just Maybe. Vaguely, he could feel the Shizuo's fingers dancing on his thigh, sending out tingles of sensation that only managed to work it's way onto his cock, letting him focus more on the promised pleasure than the current pain. Breathing in, he lifted himself up, and then came back down, the two groaning loud as the friction demanded they do it again.

Masaomi impaled himself on Shizuo's cock over and over, managing whatever half-hazard pace he could while his legs felt like they just wanted to give in. Perhaps sensing this, Shizuo pulled Masaomi closer, causing his legs to fold over, as the older man took it into his own action. Shizuo took to kissing the boy's collar, scraping teeth, brushing lips over the skin while one hand wrapped itself around Masaomi's neck. The other hand was still on the boy's thigh, a firm grip as Shizuo thrust into the stretched hole from beneath, legs and hips working in sync.

"Ahhhnnnn, Shizuo." Masaomi moaned breathlessly, eyes clenched shut as nothing but pleasure coursed through his body with every thrust to his prostate, as the slap of skin on skin brought them closer and closer to completion.

"Masaomi." Shizuo replied, barely a whisper, planting a kiss to his jaw. He unraveled his arm from the boy's neck and took the boy's leaking cock into his hand, stroking quickly and roughly with a certain goal in mind.

Masaomi's body seemed to curl into himself, forehead pressed to Shizuo's chest, as he came hard, a messy splash of white into the hand that continued to pump him, milking out every bit of pleasure it could from him.

The clench of muscle around Shizuo's cock was enough to break whatever self-control he had as he thrust in one more time, keeping himself deep and buried as emptied himself inside the willing hole, his mouth open wide as he swallowed in air, chest rising and falling as he panted for breath. He pulled out a moment later, a bit too tired to move just yet.

Masaomi groaned as he felt the strange sensation of liquid pouring out his ass, shuddering as his ass clenched around nothing. He nestled himself on top of Shizuo's chest, closed his eyes for a moment. He didn't even move when he felt a warm hand on his back.

Comforting. That's what it was.