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Attempting Sex…with Tobi…

Akatsuki Masterlist

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A/N: You try to initiate sex with Tobi, but unfortunately it’s hard since Tobi is…well…Tobi…

TW: Hand job, oral sex, mommy kink, breast sucking, getting caught, explicit. Minors DNI 18+.

You dragged Tobi to your room, wearing a sexy silk f/c robe. Tonight was gonna be the night.

“Where are we going, Y/N-Chan?” Tobi asked. You giggled. “You’ll see…” You slowly opened the door to your room and lead Tobi inside.

He gasped at the sight as you closed the door behind you. The room was adorned with candles. The rose petals on the floor lead straight to the bed.

“Ooooh, are we having a party?” Tobi asks eagerly. “We sure are…” you purred. You sat Tobi on the bed and stood in front of him.

You tugged on the belt of your robe and let it fall to the floor to reveal your sexy lingerie. Tobi gasped again, making you smirk. “You like?”

“Yes! It’s so pretty!” Tobi cooed. You sat down on his lap to straddle him. You place a hand on your breast as you flash Tobi a sexy smile. “You wanna touch them?”

Tobi reaches his hands towards your breasts as he nods eagerly. “Oooh! Can I?” You chuckle at his eagerness. “Yes Tobi!”

Tobi grabbed your breasts with both hands and squeezed them. You wrapped your arms around his neck and closed your eyes, as you took in the sensations of his touch. You let out a soft moan as the feeling of arousal starts to take over.

“They’re so soft! Almost like gumdrops!” Tobi cooed. You sweatdropped. And just like that, the mood died.

‘Okay okay…let’s just try something else…’ you thought. You skillfully unhook your bra with one hand, letting it fall to the floor. “How bout’ a taste Tobi?” You offered.

Tobi giggled. “Yes please!” You shift closer to Tobi as he partially lifted up his mask to reveal his lips. You raised a brow. ‘Is he not gonna take off his mask?’

“-Oooh!” You were snapped out of your thoughts when you felt Tobi’s lips suck your nipples. Your eyes fluttered shut as you moaned at the sensation of Tobi’s warm tongue, coated your nubs.

You threw your head back as your fingers glide through his dark hair in appreciation. ‘Whew! That tongue can work! Nice to know that mouth is good for something besides talking,’ you thought.

You smiled in satisfaction as Tobi removed his lips off your breasts with a loud POP. You hummed as you opened your eyes. “That was nice, right?”

“Yes! Thanks for the yummy milk, Y/N-chan! It was so good!” Tobi sang. You deadpanned. The feeling of arousal was now replaced with pure cringe.

You groan as you pinch the bridge of your nose. Tobi tilted his head in confusion. “Is something wrong?” You sighed. “Tobi…do you have any idea what’s going on?” “We’re playing a game aren’t we?” Tobi asked.

You decided to give it to him straight despite yours flushed cheeks. “Tobi, I love you really much. And I wanted to show you that…physically…you get it now?” You say knowingly.

“Ohhhh! You mean sex, right?” Tobi asked. You nodded as you blushed. “Yes Tobi. So do you think we could tone down the silliness for this one moment together?”

Tobi nodded eagerly. “Okay, Y/N-Chan! I’ll be good!” You giggled. “Okay, then lay down. I’ll give you a hand job,” you say with a wink.

Tobi giggled as he peeled off his pants and boxers before he laid back on the bed. Your eyes lit up at the sight of his 5 inch dick.

‘Wowwww! Tobi’s packing meat…who knew?!’ You thought. You grab a bottle of lube and squeeze it onto your hand.

You bring your hand to Tobi’s dick and begin to give him a few strokes. Tobi’s voice shuddered.

“Ooh…ohohohoho! That feels good~!” Tobi squeals. You smirk at the reaction. Now you were getting somewhere. “Feels good, right?”

“It tickles mommy!” Tobi cooed. Your eyes lit up in amusement as you continued to pump his shaft. “‘Mommy?’ I had no idea you had a mommy kink, Tobi! Want me to take care of you?”

“Yes, please~” Tobi moaned desperately. He partially lifted up his mask to reveal his lips. He then proceeded to suck his thumb like a baby as he moaned.

You deadpanned as you stopped the hand job. You were completely turned off. Tobi was taking his mommy kink way too far. ‘Okay let’s try something else…’ you thought.

You get on top of Tobi, positioning yourself so that your head was over his dick. “I’m gonna make you feel good now, okay?” You say. “Can’t wait!” Tobi cheered. You rolled your eyes.

You fluttered your eyes shut as you brought your lips to Tobi’s dick. You slowly start to suck him off.

“WHAHAHAHA!”

“HRRRRK-!”

Tobi squealed as he instantly came inside your mouth. His hips jerked upward, causing his dick to hit the back of your throat.

You took his dick out of your mouth and coughed, spitting the cum onto the floor. “Whew! That feels so much better! Thanks Y/N-chan!” Tobi sang.

You stared at him incredulously. ‘He didn’t even last five seconds…what on earth?!’ You thought.

You quickly shake it off. “Why don’t we skip to the sex?” Tobi clapped his hands. “Oooh! Fun!” You shake off the cringe and immediately instruct him to get on top of you so that he could ride you from the back. (You had a feeling that he wouldn’t be able to find your vagina).

Tobi slips his dick into your back entrance. You sigh blissfully at the fullness. Maybe this could be a pleasurable experience.

“Giddy up, mommy!” Tobi cheered. You deadpanned once again. If it were possible to die of cringe, you would have by now…

You turn your head back to glare at him. “Tobi! Sex is supposed to be quiet,” you hissed. “Aww but I wanna play! Now giddy up!” Tobi cheered again.

He starts rolling his hips rapidly, shoving his dick deep into your back entrance. You grip the sheets as you let out moans of both pleasure and pain while Tobi cheered.

You let out a yelp when you heard banging on the walls. “TOBI! Shut your mouth! I’m trying to sleep, hm!” It was Deidara. You froze. You forgot how thin the walls were. ‘Maybe it’s best to stop and find a hotel some other night?’ You thought.

Tobi turned to the walls. “Sorry, Deidara! Y/N and I were just having sex! We’ll try to keep it down!” He called.

You widened your eyes, completely mortified as your cheeks were set ablaze. “Yeah, right!” Deidara laughed.

“Did someone say sex?!” It was Hidan’s voice you now heard. You covered your face. “Oh my god…!” “Tobi says that he’s fucking Y/N,” Deidara says.

“WHAT? HOW COME THAT LOSER GETS TO CLAP THOSE CHEEKS?!” Hidan yelled out. “Looks like our little Tobi is all grown up,” you heard Kisame say in a teasing voice. “Both of you stop that. It’s none of our business,” you heard Itachi say.

Tears left your eyes as your face was on fire. All you wanted was a peaceful, quiet, romantic night! Now the entire base knew that you were having sex!

“Don’t be sad, Y/N chan! I’ll ride you faster if you like!” Tobi sang. “No! Fuck you, Tobi!” You cried. “But you are,” Tobi says.

You growled furiously. “TOBI! GET OUT OF ME!” “Giddy up, mommy!” Tobi cheered as he rapidly thrusted into you again. You cried and moaned as you gripped the pillows.

You cried for Tobi to stop but he just kept going. “Damn! Tobi must be getting that bitch wet! That’s it I’m coming in!” Hidan laughed. “Nooooooooo!” You wailed.

You heard Hidan banging on the door. “Tobi get out of me!” You cried. “But I’m so close!” Tobi moans. Your face was now redder than hell itself. “TOBI IF YOU DON’T PULL OUT-!”

“WEEEEEEEEEEEE!” Tobi cheered as he dumped his whole load inside of you. You whined at the sticky goop that filled your entire back entrance. Tobi finally pulled out.

“Look mommy! I covered you in milk!” Tobi cheered. “FUCK YOU TOBI! ITS OVER!” You roared. “I HATE THIS!”

“Don’t be sad, Y/N-Chan! Cmon let’s go for one more round!” Tobi cheered. With that, he shoves his dick back into your hole. “NOOOOOOOOO!” You wailed.

Tobi squealed and cheered as he rapidly thrusted into you. You screamed in pain as more tears soak your pillows. “TOBI IT HURTS! STOP!” Tobi stops thrusting. “I can’t! I’m stuck inside of you! It’s very tight in there! Hee hee!” You widened your eyes in horror.

That was when you heard a booming laughter come from Kisame and Deidara. Immediately followed by Itachi. You thought you felt your heart stop because Itachi’s laughter was the scariest thing you have ever heard. You didn’t think he was capable of doing so. But now all respect you had for him was officially gone.

Now you were furious as you squirmed. “GET OUT OF ME TOBI! GET OUT!” You roared as tears continued to soak the sheets. “Dont tug so hard! You’ll give me a boo boo!” Tobi whined. You buried your hot face in the pillow and hysterically screamed from both the pain and the embarrassment.

That was when you heard a loud bang. You and Tobi turned seeing a red scythe has poked through the door, creating a hole. The scythe pulled out revealing Hidan. He gave you a manic grin.

“Open up bitch! I’m clapping those cheeks next! And that pussy better still be tight for me!” He laughed.

You didn’t know whether to feel mortified or relieved. Maybe anyone would be a better experience than Tobi. But you weren’t sure if you were even gonna recover after this…

Okay so think this- Itachi falling in love with sasuke’s ex teammate who is on team7. Let’s just pretend that team7 was a five man squad. Relationship headcanons for that scenario? Ily 😳❤️

((Hehe yes~ I hope these are to your liking! And that I didn't ramble on to long wjwjs))

Headcanons for Itachi falling in love/dating Sasuke's exteammate

Before

Itachi was so confused when he realized he fell in love

Especially with them

He had remembered them from before he left, but other than that all he knew was what Sasuke had said.

They were a shinobi and he was a criminal. Not only, but Sasuke had left for his revenge so long ago. Itachi didn't even think that they'd remember him.

On the Kazekage rescue mission however, eye contact was all he needed.

They remembered him.

He didn't know how to feel, but any romantic action could get the both of them in very big trouble.

After Itachi's intitial sight of them, he knew he had to see them again.

Why? When it risked so much for the both of them?

Love was a finicky thing

Soon after, he used a crow to sight them out and soon found them when they were in the forest surrounding Konoha. Out of the village where they wouldn't get caught.

They instantly got defensive when he approached, asking if they knew anything about Sasuke. A diversion.

When they replied 'no', he sort of dipped into the reason why he initially approached them.

"I couldn't help but remember you..from all of that time ago..you've grown stronger."

Wow a compliment. Savor that, reader-chan.

If they acted hostile and demanded him leave, Itachi would comply and would never return.

If they calmed down (even if they were still a bit defensive, as expected in the presence of a criminal) and kept a decent conversation, he would ask if they minded meeting him here again.

If they denied, he'd respect their choice and would stop following them and would not return.

If they accepted, he'd give a small smile and poke their forehead. Then he'd go on his way before they were both prodded about where they were.

After a good handful of meetings, Itachi could feel his romantic attraction to them build. However he was very hesitsnt due to still calculating the risks of being in a relationship.

Anyone looking to hurt him could go after them, the Leaf could force them into giving information about him..it was all the matter of risk.

If they started to act flirty, he might turn it down for now. He didn't want any influential sway about his final choice.

Finally, he had made the choice that you only live once and he'd protect them the best he could from all of that.

If they denied he'd reassure them it was okay, but then he'd likely receed from them and never show up again.

After

Dating would be very secretive

The Akatsuki can't know, nobody in Konoha can know.

Since they were still actively on team 7, he dreaded that one day they might have a mission to attack him.

All he could do was hope.

However, that was only in the back of his mind.

The longer they were together, the more open he was with them.

He told them stories of his younger days, certain recipes and especially baby Sasuke.

However, as much as he loved them, he would not share any of the Akatsuki's information and asking him for it would warrant some distrust from him. He'd think they were only with him to get information and would likely abandon the relationship.

However if it was an accidental question that was like 'what's it like' or 'do you all share a bathroom', something clearly innocent, he wouldn't get freaked out.

Do not ask to join the Akatsuki. No. Absolutely not. He doesn't want them to risk getting in any shit with Konoha or in any of the trouble that follows the criminals around everywhere.

Please do not bring up anything about the Uchiha massacre. At all.

If they were to abandon Konoha and live outside of the village, Itachi might bring Kisame by on the way to or back from a mission.

Kisame definitely would know about Itachi's s/o and these two are like the Fort Knox of this secret.

If Itachi's s/o gets along well with Kisame, he's absolutely elated.

Sometimes Itachi will stay with them overnight, mostly if he has a relaxed time solo mission.

If they stay in Konoha, they sadly can only meet in the forest. S/o better be careful because they might rouse some suspicion.

Itachi would be a lot more careful with things like dates, only really taking them in secluded places with low chances of others seeing them.

If his s/o learns ANYTHING about Sasuke, Itachi will find out. If you try to hold it back he'll get very upset.

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