To Teach

Title: To Teach
Series: Durarara
Experienced Masaomi – Inexperienced Izaya
Disclaimer: I do not own Durarara, nuff said.
Warnings: Boy on Boy action

This was another fill request. Enjoy!

Masaomi whistled a nameless tune as he walked down the streets to Izaya’s place. It was just a week ago that he had gone to Izaya’s place to yell at him about a job, only to end up having sex instead. At first he hated himself for it but later he got over it and figured it wouldn’t hurt to have another sex partner.

Today he was feeling extremely horny and needed a release. His thoughts went to Saki but then quickly left his mind when he realized he could not think of her that way. They had been living together for well over five years now but they still hadn’t gotten past anything but a kiss. He knew it wouldn’t be long before they both went their separate ways.

With Saki out of the question he went over his list of people he could have sex with. Unfortunately he figured it would be stupid to try to get into contact with any of the people form his past.

Then it hit him like a ton of bricks. His only option was Izaya. The irony of the whole thing was quite fucked up.

He just hoped Izaya would be in the mood today as well. The last time they had sex was good but it was kind of vanilla, in his opinion. He was ready to crank it up and wondered just how perverted Izaya could be. It got him a little excited.

Finally he reached Izaya’s place and stood outside the door, ringing the buzzer. He knew that Namie was probably already home at this hour, which was why he chose it.

“Masaomi, I’m surprised to see you here on your own volition.”

Masaomi just rolled his eyes. “Are you going to let me in or are you going to leave me out in the cold?”

Masaomi heard the sudden buzz of the lock being undone and walked in the door, making his way to Izaya’s floor.

When he walked in Izaya was sitting in his usual place next to the computer. He was typing away at something but stopped when he noticed Masaomi had come in.

“So, what brings my fellow employee here so late in the day?”

Masaomi walked up to Izaya to get closer to him. “Like you don’t already know – There is only one reason I would be here when I don’t have to be.”

Izaya pushed away from his computer to turn his full attention on the young ex-gang leader. “Oh my! Have you come to confess your love to me?”

Masaomi’s eyes bugged out at his words.

“If you are then I would have to say that might cause some problems between me, you, and Saki.”

Masaomi narrowed his eyes at Izaya but tried to keep his cool. He had to remember who he was dealing with and just ignore what his stupid mouth was saying.

“Hardly- All I want from you is your cock.” He spelled out the words loud and clear so that Izaya couldn’t continue with his ridiculous mind games.

Izaya’s smile instantly left his face.

“Aw, you love to spoil all my fun. Well forget it. I’m not in the mood to sleep with a moody-”

Izaya was cut off when Masaomi grabbed him by the shirt and pulled him into a kiss. When they broke away Masaomi grumbled. “Just shut up already and do me.”

Izaya was a little taken off guard by how forward he was being. However he was now officially turned on and knew there could be no way for him to turn the boy down now.

Getting fed up with the desk being between them – Masaomi jumped up on it and made his way to Izaya’s side.

Izaya helped him along – as they continued their heated kiss – but instead of letting him off the desk he forced Masaomi to lay down on it.

Masaomi wondered what Izaya had in store for him, but when he didn’t make any other moves he began to feel a little disappointed. Still, he figured it would come later and just let Izaya continue to take the lead.

After a few minutes of kissing and mindless rubbing Masaomi was ready for more. He wrapped his legs around Izaya’s body and pulled his mouth up close to his ear.

“I want you to do all kind of naughty things to me this time.” He whispered in a sultry voice.

Izaya paused a bit and Masaomi wondered what was up.

Then he lifted Masaomi up and started to carry him off to the bedroom. Masaomi didn’t fight it, even though he was kind of hoping for desk sex.

As soon as they reached the room Izaya placed him on the bed and began to strip. Following his lead, Masaomi did the same. He didn’t want to drag out the boring part. He was dying for the skin on skin contact.

Masaomi’s penis twitched in anticipation at the site in front of him. He may have once hated this guy with all of his might but there was no doubt that he was good looking. His skin was smooth and perfect, and his build was lean but strong. Everything about him screamed delicious. He felt like the luckiest guy on the planet right now.

He sat back down on the bed – now completely naked – with a just as exposed Izaya in front of him. He laid back and motioned his finger towards him, beckoning him to come.

Izaya didn’t need to be told twice. He quickly crawled up on top of Masaomi and pressed his chest down on top of his, kissing him once again. The heat of their bodies made the kiss feel three times more powerful than the first one.

They thrust their hips together, rubbing their penises and creating such a wonderful friction to a simple and slow tempo. They moaned together, swallowing each other’s moans every now and then letting them escape because they liked the way it sounded.

Izaya began to talk, but it was short and raspy.

“You – ah – feel – mmm – so good.”

Masaomi felt a bit of pride at that. Izaya was always someone to just make ugly comments and stomp you to the ground but when they were fucking he would complement Masaomi in all sorts of ways.

The last time he had gone on and on about how nice his body was. He almost felt like a girl – when a guy keeps telling her she is so beautiful during sex – but he did like it. That was one of the reason the sex was pretty good despite being so vanilla.

Masaomi broke away from one of their heated kisses so he could move on to other things.



“Suck me, please.”

Izaya nodded and bent down to his cock.

Masaomi waited in anticipation. It had been awhile since he had gotten a blow job and missed it. He really looked forward to seeing what Izaya could do.

Izaya began to lick his length, using his hand to pump him a little.

Masaomi shivered at the feeling but something was wrong. Izaya’s touches seemed, wavering and unsure. He wondered if it was because he didn’t want to do it. When Izaya placed his mouth of his rock hard cock Masaomi knew right away what was up.

He sat up quickly and pushed Izaya away.

Izaya looked surprised but didn’t say anything or fight it.

“Have you never done this before?”

Izaya averted his eyes and Masaomi knew he had hit the nail on the head. He couldn’t believe it! Izaya was inexperienced!

“That is – there is no easy way to put it – very shocking.” Masaomi clicked his tongue in thought.

Izaya seemed to be genuinely embarrassed about it too. It was really throwing him off.

Then Masaomi remembered his first few times and how awkward it had been. He was thankful that the guy he was with was very instructive and patient. It dawned on him that he was going to have to be that guy this time. A new found excitement bubbled in his chest. He would have dominance over Izaya. It was something he always dreamed of one day but never figured it would happen.

Masaomi quickly shook his head and decided now was not the time to gloat. He would do so later, after the sex. He could tell that Izaya was starting to pull away and he didn’t want that.

Still, Masaomi couldn’t help but get a sadistic smirk on his face. If he didn’t know any better he would think that somehow they switched personality’s right then.

“I guess we will just have to change that. I’ll demonstrate and then instruct you.”

Izaya nodded his head but Masaomi could tell he was trying to get back to his normal, bastard, self. Masaomi knew that wouldn’t last with his skills though.

Masaomi roughly pushed Izaya down on the bed and pushed his legs apart. He marveled at his erect length in pleasure. He could see small and thick drops of pre-cum spilling out from his swollen end and darted out his tongue to lick it off.

Izaya jerk a bit when he felt this and Masaomi smirked once again as he grabbed his length and began to pump him up and down, slow and then faster.

Izaya jerked around on the bed, doing all he could to stay calm.

At that moment Masaomi opened his mouth and took him all in, as much as he could. Izaya couldn’t help but gasp at the new feeling and thrust his hips up a bit to meet with him.


Masaomi pumped him up and down and sucked harder and harder, hitting pleasure points Izaya never really knew were there.

Izaya thrashed and tried not to thrust too much, he didn’t want to hurt Masaomi. It was really hard though, he had never felt so good. He grabbed on to the bed sheets to try and keep himself steady but just when he thought he could control himself Masaomi grabbed both his balls and squeezed lightly.

Izaya screamed out his name again and came into his mouth. He was planning to warn him but he didn’t get much of a warning for himself.

He was about to apologized until he noticed that Masaomi didn’t seem to mind one bit. In fact the sight of him licking his lips caused his penis to start twitching again. The boy had a hold on him like no other human ever had. He never thought one person could keep his attention this long – and this strong – but Masaomi was it and he was going to do all he could to make sure he never got away.

“Now that I showed you, it’s your turn.”

Izaya nodded his head. He would do this right and let Masaomi know he was a fast learner. He would not be humiliated again.

Masaomi rolled over so he was now on his back. Izaya took the same position that Masaomi had and looked down at his penis. It was really swollen, more so than it had ever been the last time. His pre-cum was getting so bad that it was running down his length.

Izaya licked it up like a lollipop and found the taste to be a little bitter and salty. He wondered how Masaomi was able to drink so much of his.

He must have given off a face because then Masaomi laughed.

“Don’t worry, it’s an acquired taste and I won’t be offended if you spit it out.”

Izaya sort of looked miffed by this. He didn’t want to be treated that way but it wasn’t like he could say anything back.

“You got two ways to do this. You can either, just try and take all of me that you can and try to imitate what I just did to you or you can let me instruct you slowly.”

Izaya shook his head.

“I’ve got this.”

Masaomi was about to say more when he felt warm lips wrap around his length and suck hard on just the tip part.

Masaomi closed his eyes and let out a moan of pleasure. As Izaya continued to suck his tip he used his hands to thrust the rest of him. Masaomi jerked his hips up to meet with his hand thrusts.

His thrusts became smaller and smaller as his mouth took over more and more of his penis.

Masaomi whimpered and couldn’t believe how quickly Izaya had picked up on it.

Through his sucks Masaomi felt Izaya tongue hit a certain spot around his penis and his tip. He bucked hard on reflex and caused Izaya to gag a bit when he hit throat.

Masaomi looked at him with guilt and apologized. Izaya just shook his head and continued to work on him.

When hit tongue hit that spot again Masaomi did all he could to keep from jerking.

“There! That is the spot, there!”

Izaya understood and kept his attention to that place as he sucked and began to play with his balls.

Masaomi was just about there. He looked down the see Izaya head bobbing up and down and it was the last straw.

“Izaya, I’m cumming.”

Izaya didn’t stop though and Masaomi was surprised. He came within the next few seconds and watched as Izaya tried to swallow most of it without gagging.

It was amusing how hard he was trying. He had to admit, he seemed to be doing better than his first time.

When it looked like he had gotten over it Masaomi tackled him and pushed him back down in the bed again. He kissed him with a fire – ignoring the after taste of his own cum. Izaya didn’t protest in the slightest and reached his arms up above his head to pull Masaomi down on top of him.

Masaomi felt how hard Izaya was again when he did this. It was already starting to make him feel hard again. He pulled away from their kiss and took Izaya’s hand.

Izaya watched in wonder as Masaomi placed three of his digits in his mouth and began to suck. It was a truly hot sight to see. He sucked and licked them good until they were nice and moist, dripping down a bit as well. Then he turned and put his butt in his face. Izaya knew what this part meant but he wondered why he went through the trouble of sucking his fingers when he had lube.

“Are you sure you don’t want me to get the lube?”

Masaomi growled. “Just do it.”

Izaya placed two of his fingers in him immediately and Masaomi stiffened at the mixture of pleasure and pain. His penis was now fully hard again so he began to stroke himself as Izaya continued to finger him, stretching him out with scissoring him, then placing a third digit in.

When he thought he couldn’t last much longer, Masaomi pulled away and turned back around. His face was flush, Izaya noticed, and he smirked in knowing that was because of him.

Masaomi placed himself over Izaya’s cock and took a deep breath. In one swift move Izaya’s throbbing organ filled Masaomi and it was all he could do to keep from screaming out from the rush it gave him.

He stayed still to get use to the feel. Izaya looked at him with so much lust on his face. He could tell that he is trying hard not to move already.

As he got use to it he began to rock back and forth, letting Izaya’s penis fill him even more.

Izaya began to slowly lift up his hips to meet with the rocks. It was slow torture to the both of them and Masaomi knew they wouldn’t get far in their current position. He pulled off and laid his face down on the bed with his bottom in the air, waiting for Izaya to refill him.

Izaya got up and thrust back into Masaomi quickly, causing them both to moan really loud.

Izaya continued to pound into him and Masaomi was thrilled by the feel of it but he wanted something more.

“Izaya, this feels great and all but I need more.”

Izaya sighed in annoyance.

“What is that?”

Masaomi tried to think quickly but realized he didn’t really have all that much to work with. “I want you to use something to tie around my head so I can’t see and then my arms.”

Izaya raised an eyebrow, he never expected Masaomi to be that kinky, but he didn’t say anything as he pulled out and went over to his bedside to get some of his scarfs. He was tempted to grab a yellow one but decides against it since he wouldn’t be seeing it anyway.

When he came back he tied the black one around his eyes first. Masaomi said nothing and even helped him with the next part by putting his hands together.

Izaya tied it gently but Masaomi snorted.

“Tighter, I don’t want to be able to get out of it.”

Izaya decided then and there to stop acting nice and tightened it as much as he could. It was going to leave a mark later, he was sure of that. Masaomi didn’t complain though.

Without warning, Izaya plunged right back into Masaomi’s ass and shuddered at the feeling of his muscles tightening around his cock.

Masaomi shuddered as well and started to really get into it now. He senses were on over drive now that he could no longer see or use his hands to stop it. If anyone else knew about this they would think he was really stupid to let Izaya tie him up but he just didn’t care at that moment. He wanted it hard and he wanted it kinky. He liked the small sense of danger from letting Izaya have all the control.

His speed began to quicken, setting an interesting tempo from slow and hard pounds to fast and speedy thrusts. Masaomi was surprised by this and wondered if Izaya was doing it on purpose. He was torturing him by it because it was bringing him so very close but then slowing it back down.

“You are being a tease. Slap my ass if you are going to be that way.”

Izaya felt a little embarrassed by this but did as he was told. Masaomi hissed slightly but didn’t yell at him for it.

Masaomi began to rock back from side to side on the bed and Izaya wondered what he was doing.

“Hey, put me on my side.”

Izaya moved him so he was now his side, one leg between his legs and the other wrapped around his waist. Izaya saw this as a good opportunity. He would really be able to thrust into him deep now.

He pushed in and Masaomi let out a noise Izaya had never heard before.

“That’s the spot!”

Izaya pulled back out, only leaving the tip and then pushed back in at full force, hitting that spot again. Masaomi shuddered – he wouldn’t be able to hold out much longer.

Izaya pumped him harder and faster, gaining speed because of the better position. They were almost there – both calling out each other’s names. Izaya took hold of Masaomi’s penis and began to thrust it with each pump.

With one last, hard, thrust, they both came – Masaomi all over Izaya’s hand and bed, and Izaya deep inside of Masaomi’s ass.

They both fell down on the bed, not caring about the wet spots. They were already covered in sweat and sperm in the first place.

Izaya took the time to release Masaomi from his bondage and then lied back down.

As they lay there panting, Masaomi thought now would be the perfect time to gloat.

“I can’t believe that I had to teach the infamous know-it-all about good sex.” He sat up a bit to give a toothy grin at Izaya’s face.

Izaya glared at him but Masaomi noticed it wasn’t heart felt. He bent down and gave Izaya a sweet and lingering kiss. It wasn’t like him to try and be sweet with Izaya but for some reason he couldn’t help it.

Then he lied back down to try to get some sleep. That had been quite a work out for the both of them.

“Next time-”

The room was quiet. It was just the sound of their raspy breathing echoing through the room but Masaomi knew that Izaya was still listening intently.

“I will have to bring some of my toys.”



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