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detectivestucks · 8 months ago

Text

The Bet

18+ Content, Minors do NOT interact

Pairing: Tobi x F!Reader

Summery: You are relatively new to the Akatsuki and your best friends Konan makes a wager with you. When you lose, you're forced to take Tobi on a date.

Warnings: NSFW, canon violence, mentions of biting, fingering, oral-male receiving, unprotected penetration, facial.

Word Count: 4.8k

Anon Ask via DM: Been getting a lot of Kakashi request so I was happy to write for Obito again :)

Tobi always had eyes for you.

Nothing happens in the Akatsuki without his approval but when Konan asked Pain to let you join their troop of miscreants, Tobi overwhelmingly approved of Pain’s decision. You were skilled, vicious, and adorable. You captured the attention of every man you came across. Even when fighting enemies your beauty captivated them. They shamelessly flirted with you as you battle to the death.

“Come on gorgeous, why don’t you drop the katana and I‘ll take you on a nice date?”

“Wow, strong and beautiful. Maybe after this I can take you to dinner.”

“Keep trying to kill me and I might just ask you to marry me.”

The pick up lines were pathetic and met with a resounding rejection that was usually followed by ending their lives.

Yes, Tobi had eyes for you alright. He felt a twinge of envy for anyone who joined you on missions because you were a brilliant sight to behold when you hunted your target down. You weren't a victim to the harsh realities of the shinobi world. You were the harsh reality of the shinobi world.

Always hanging around with Konan, the two of you whisper to each other whenever you’re at the hideout between missions. The other members always came over to talk to you, trying to impress you with boyish charm and corny pick up lines. They would leave you in a fit of giggles and whispers while Tobi watched from a distance. He wanted you as much as the other guys but he had a double life to worry about. He’d leave the rest of the crew to hopelessly fawn over you and your seemingly high standards.

One afternoon the two of you are chatting away in the corner of the main room laughing at Deidara and Hidan who are putting on an impressive display for you both when Tobi walks through. He runs up to his partner and clings onto him for dear life, pretending to be a damsel in distress

“Oh Deidara! There was a mean man outside! Make him go away with your very impressive art.”

He tilts his head to the side and you just know he’s batting his lashes below his mask. You and Konan crack up at his ridiculous mini play. You enjoyed Tobi. He was funny and pissed Deidara off constantly. He was the much needed comic relief amongst a bunch of moody, brooding, arrogant rogue shinobi. However out of all the guys in the gang he was the only one you weren’t interested in. Even Zetzu had a better chance ending up between your legs than the orange masked idiot.

Konan sees you laugh a little too hard at Tobi and nuzzles her lips against your ear,

“What do you think Tobi’s like on a date?”

“Oh gods I hope I never have to find out. He’d probably cling to his girlfriend the way he hangs on Deidara.”

You both snicker at that, certain it’s true.

“Care to make a wager then?”

Konan piques your interest and you lift a brow at her.

“Next mission, the woman with the least kills asks Tobi on a date.”

You turn to her with your mouth open. “Konan! You seriously are willing to keep living here if you lose?”

“Oh I’m not losing.” she says, crossing her arms.

“Well I’m sure as hell not losing either.”

The both of you continue to stare at your animated comrades when you speak again.

“What does the winner get?”

Konan snorts “Not going on a date with Tobi.”

“Besides that!”

“I don’t know.: She thinks for a quick second. “They have to invite their crush into their bedroom.”

Your eyes dart around the room, not sure who to choose. There were a lot of guys in your gang that you wanted to sleep with. Pain was off limits cause of Konan but Kisame was ripped and had that sexy predator thing going for him. You bet he bites and when he does, it breaks the skin. Then he probably soothes your wounds by licking up the blood while he fucks you stupid on his cock.

Your eyes pan over to pretty boy Deidara who was gorgeous with hair you wanted to pull while his mouth lapped between your legs. You thought about all the sinful things the mouths on his hands would do to you and it makes you cross your legs.

You look at Hidan who was crazy hot and twisted. You could see him getting freaky during your period and you wanted to surrender to the ‘way of jashin’ for just one night, letting him do whatever he wanted to your naked body.

Lastly you peer over at the quiet Itachi. Reserved, kept to himself, and well mannered. The kind of guy you could bring home to your mama but was probably a filthy boy in bed. You imagine him slapping you and calling you degrading names while his eyes glow red.

“Can’t decide, huh?” Konan says with a light jab.

“Well not all of us joined the Akatsuki with our childhood crush.”

“Don’t worry, you won’t have to choose. Cause you’re gonna lose.”

You open your mouth and look at her pretending to be gobsmacked. “Oh it’s on!”

****************************************************

Konan picked a good time to wager her little bet cause your next mission was a full fledged raid. One thing you envied about Konan was her ability to make shuriken out of paper, leaving her with an endless supply of weapons while utilizing minimal physical effort. You on the other hand had incredible speed but only two kunai and a katana at your disposal. No one could match your lightning speed, not even the raikage himself. But you could still only attack up to two targets at a time.

The night was long and the body count was high.

…and Konan was kicking your ass.

You were desperately trying to take out more targets than her but her range was so much farther than yours. You were needlessly brutal, terrified of the horrible date night that was to come at the end of the mission. The first rays of light shone over the rooftops when the two of you finally made your retreat.

“Your count?”

“78” you pant

“Ha! I win! 102”

“Shut up!”

She only smiles back at you.

“Fuck! Now I have to ask out Tobi.”

“Sucks to suck”

“Oh gods, what if he wants me to suck his dick?!”

“You better open wide.”

You shove her off the tree she jumped on but she caught herself by creating paper wings and flew the rest of the way home. Smug bitch.

You meet up just outside of the hideout, entering together. As soon as you walk through the threshold Konan begins to shout.

“Tobi! Y/N needs you!”

“I hate you so much right now.” You grumble under your breath.

She sticks her tongue out at you, “Deal with it. I’m gonna go find Pain.”

She leaves in a twirl just as Tobi timidly enters the room.

“You needed me, Y/N?”

“Yes…I have something to ask you.”

Tobi just stands there, staring at you behind his mask, head eerily tilted to the side. Gods he’s so creepy. You begin to wring your hands in front of your stomach, building the courage to ask the dreaded question.

“Tobi…would you…” you bite your lower lip in the most adorable way and Tobi can feel his heart twist in his chest. “Would you go on a date with me?”

“Oh.”

You stare at him, unsure of what to make of his response. Maybe he was going to reject you. Maybe you won’t have to go on a date at all. Thank the heavens.

“What do you have in mind?”

“I-uh…” Fuck! Now I have to plan the date too?! Konan I’m gonna kill you. “I hadn’t decided yet.”

There was a moment of silence between the two of you.

“Do you want to go or not? Cause I can go ask one of the others if you’re not interested.”

Tobi scratches the back of his neck and responds in his childish tone.

“Geh, Y/N, I’d be happy to go on a date with you.” He brings his hands together in front of him and tilts his head to the side in a feminine display, “I just wasn’t expecting it is all.”

It took everything in you not to cringe so instead you force a laugh. Maybe he was just trying to be funny. Yeah, that’s it, he was trying to be funny.

That night you get dressed in a long flowy pale pink skirt with slits along each thigh and a fitted cream colored top with corset detailing around the bust. You hoped one of the other guys saw you in it and would knock on your door later to show you how a real man treats a woman. For now, though, you needed to focus on making it through your date with Tobi.

He knocks on your bedroom door and you walk over to answer it. Tobi stands before you in a fitted black shirt and black pants covered in a long black kimono adorned with a dark gray geometric pattern. It wasn’t a bad look but he hid every inch of his body from everyone as usual.

“Wowzah!”

You smile and roll your eyes. “What, never seen a proper woman before?”

You turn around and retreat back into your room to grab your cream square heels, sliding them on while balancing yourself with Tobi’s arm.

“So where are we going?”

You look at him and smile playfully “You’ll see.”

You grab Tobi’s hand and pull him through the hideout, heading towards the exit. As you walk through the common area, Tobi looks to the side and sees the jaws of Hidan, Deidara, and Zetzu fall to the floor. He can’t help but feel a swell of pride at their jealousy.

The date, however, was terribly awkward. You tried your best to be flirty but you had no way of telling how Tobi felt. You couldn’t see him smile or blush. You couldn’t tell if he was staring at you with interest or anger. It was extremely one sided and uncomfortable. You did your best to sell the lie but it was probably painfully obvious that you didn’t want to be holding hands with a big masked baby.

On the way home you sway as you walk next to him, both arms hugging his right one, trying to maintain a normal conversation. It occurs to you that this might be your only chance to ask the burning question everyone in the Akatsuki is thinking.

“Tobi? Why do you wear the mask?”

“Because I don’t want anyone to see my face of course!”

You roll your eyes. “Okay but why don’t you want anyone to see your face?”

“That’s for Tobi to know.”

You shake your head “What, you ugly or something?” You squeeze his bicep flirtatiously. “You get stuck in a house fired and are covered in scars?”

Tobi goes stiff in your hold. You drop his arm and bring both your hands up to your mouth.

“Oh shit, I’m sorry. I was only joking!”

Tobi walked next to you in silence. If you thought it was awkward before, that was nothing compared to the embarrassment you felt now.

“Tobi, you’d have nothing to be embarrassed about you know. It’s not like you’re the only freak in the circus. I mean. Kisame is practically a shark, Sasori lived inside a puppet, and Hidan drinks blood to become a skeleton.” A hot ass skeleton but Tobi doesn’t need to know that. “We’re all weirdos.”

Tobi still doesn’t speak but his body relaxes some. He was getting a little easier to read but you still couldn’t wait for the night to be over. He creeped you out and you still had no respect for him. He was a fool even if he was kinda funny.

You finally make it back to the hideout and much to your disappointment, everyone has gone to bed. Tobi walks you to your side of the hideout next to Konan’s room and awkwardly gives you two pats on the shoulder before telling you he was off to bed in his high pitched kid’s tone.

You turn to unlock your room with a signature roll of your eyes relieved the night was over.

“Pfh, what a loser, bet he’s never even made a girl cum in his life.”

As Tobi’s walking away he overhears you and stops dead in his tracks. He knows that he’s playing a fool but it wouldn’t hurt to teach you some manners and show you who’s really in charge of the Akatsuki while he’s at it.

Just as you open your door you feel two gloved hands tightly grip your biceps. Someone had snuck up behind you.

“What’d you say?”

The voice was rich and deep. It was a cold blanket that covered you with fear and made chills creep down your back. Your breath falters. You didn't dare turn your head.

“Tobi?”

He pushes you into your room with a finger shoved into your spine between your shoulder blades.

“Would you like to test that little theory?”

You turn around, face painted in fear as you search Tobi’s orange mask for answers. He slams the door closed behind him. Tearing off his robe as he swiftly steps forward causing you to retreat away from him backwards. You’re too distracted by the sudden change in his demeanor to notice the bulging muscles poking through his skin tight shirt before he picks up a shoe and throws it against the wall to kill the lightswitch.

You reach your arms in front of you, ready to push him away but he somehow passes through them and has a grip on your hair while he is sucking on the skin of your neck. An involuntary pleasured grunt escapes you, realizing he discarded his mask and has his lips locked on your skin. You keep trying to push him off but every time your hands pass through him while his grip against your hair remains solid. You couldn’t figure out how it worked but you were starting to no longer care as he created various bruises along your collarbone. You begin to pant slightly, feeling arousal pool between your legs from how he nibbled against your sensitive flesh. Your mind was slowly fogging over and in your haze you wanna hear his voice again.

“T-talk to me. I wanna hear you s’more”

“And say what, Princess? Tobi isn’t my real name?”

His voice was smooth and intimidating. It made your eyes roll to the back of your head. You lean your face against his.

“Yes, tell me more.” you whisper

“What do you want to hear? That I’m the actual mastermind behind the Akatsuki and you are all my little puppets?”

You begin to lift your leg and wrap it around his waist. Panting from how his baritone tickled your mind.

“or that I’m going to fuck you like a whore right now and turn you into my personal concubine.”

“Yes”

You lunge for his lips, hands clawing the back of his head to pull him into you. You had never been so attracted to a voice in your life. You had no clue what he looked like but you knew he had adorably messy hair and scars on his face. You could feel the tough skin with your lips. He backed you all the way over to your bed and switched places with you so that he could take a seat before pulling you into his lap.

You straddled him, your heat pressing over his concealed boner, while you feverishly made out with him in the pitch black room. Your kisses left his lips and traveled over the ridges of his face, sucking and breathing on the battered skin he was afraid to show, before you licked a stripe up his cheek.

He anchored you at your hips and pulled you down on him while he rutted up into you. You cried a needy moan into his ear as your fingers played in his hair.

“My, my, I think I can make you cum without even touching you. You’ve got yourself all worked up over a little conversation and sitting in my lap.”

You groan at the sound of his voice and begin to grind on him, needing the friction while you kiss his lips. You rub your chest against him as you work yourself up into a frenzy. He reaches behind you, looking for how to take off your shirt when he gives up and opts to rip it off of you instead.

You let out a small cry, partly in awe of his raw strength but partly because that was one of your favorite tops.

“I don’t tolerate anything getting in my way.”

“Uh-huh” you agree breathily, cupping his face in your hands, recapturing his lips with yours. As much as you want to keep hearing that velvet voice, you want the lips that form the words to be interlocked with yours. Your arms wrap around his neck as you push your barren chest against his clothed one. His hands explored your soft back. You were glad to feel his fingertips dance over your skin and not his leather gloves. You wondered if you’d get to feel all of him tonight. You could tell how toned he was through his clothes and were dying to lick and nibble his chest.

“Tobi,” you pant against his face, “please make me cum.”’

He hums and grabs you at your thighs flipping you onto your back and kneeling over you. Your hands continue to explore all over his upper body, running up from his forearms to his biceps, sliding over his delts, and tracing down his traps before sinking your nails into his rhomboids. He grunts into your neck. Arousal puddling in your underwear at the sound.

You wrap your legs around his waist, lifting your hips and grinding into him some more. Panting and needy, the mystery of him increasing your desire. Tobi grabs the front panel of your skirt and pulls it aside, yanking your panties out of the way. You drag your lips along his jaw.

One of Tobi’s fingers traces along your slit, collecting some of your slick and smearing it along your sensitive nub hidden within your folds. You twitch from the sudden contact and can feel him smile against your face.

“Someone's sensitive.”

A high pitched “mhm” comes from you as you push your face against his. His thumb casually rubs circles between your legs. Shuddered moans expel into Tobi’s ear as your arms slide back up to Tobi’s neck and wrap around him tightly. He lets a finger slip past your entrance, stroking in and out twice before being joined by a second.

Your eyes snap shut. He pumps his fingers in and out of you. Your head falls back in pleasure as he scissors you open, playing you like a violin. You squeeze around him, soaking in how it feels to be touched for the first time in over a month. Back in your village you were a menace and well hated but you were never short of male companionship, even if it always ended terribly. Once you officially became a rogue ninja the world was much more lonely than expected. You had imagined it would be different once you joined the Akatsuki but to your own surprise, you didn’t take a lover till tonight. Short of breath you manage to wheeze out,

“Thank you Tobi”

“Good girl, you know your manners.”

His condescending praise filled you with butterflies when spoken in his bassy tone. You respond by nibbling on his lower lip. You so badly wanted to rip off his clothes but you didn’t dare, too afraid he’d stop. Instead you softly beg into his ear,

“Please shove your cock into me.”

“Of course, Princess. How can I say no when you ask so nicely.”

A small cry of excitement whines past your lips. He darkly chuckles at your neediness. What a sharp turn from the bitch who tried to make a mockery of him by asking him on a date as a joke.

He’d make you pay for that. He intentionally wasn’t pursuing you before but since you sought him out with your farce, now he’d take full ownership of you. You were going to be his property now. He wasn’t talking dirty when he said you’d become his concubine. He meant it. You’d be chained to him, only let off your tether during missions.

He opens the front of his pants and slips into your quivering entrance, stretching you uncomfortably as he pushed his excessive girth into you. A pleasured wail drew from your mouth.

“What a good girl. Tell me Princess, do you want more?”

“Yes!”

You cry the word. He pulled back slowly just to plunge back in. You sink down into your mattress, getting shoved into it deeper with every inward thrust. It was rough. There was nothing gentle about the way he fucked you. His swollen head pummeled into you, dislocating all your organs. He folded you in half as he pushed in. Your knees found a new home by your ears, his body pinning the backs of your legs, pushing your thighs against your chest. In the darkness he could see the whites of your eyes as they rolled back in your head to look at your melting brain.

Your mouth was left agape. You were babbling and drooling from his dick dragging in and out of you. You swear you’d never been fucked so good in your life. He brought you to tears on his schlong, pistoning in and out of you. Your nails digging into his back once more.

“Gods damn, Princess!”

Tobi was struggling to maintain his domineering composure. He was losing himself inside of your pussy. It gripped around him tightly. The pink muscle constricted around his member, attempting to milk him before he was ready. “Eager little fucking slut.”

He husked between thrusts. You body fell limp. You became a rag doll under him. The only part of your body that was tense was your gummy walls which held onto him with a death grip. He pushed his sweaty forehead against yours. Holding the back of your head.

“Fuck this pretty pussy. It belongs to me now. You belong to me. Understand?”

You wished you could’ve answered. You would’ve told him yes. You would've told him that you’d never leave his side. That you’d bend over for him anywhere. You’d wrap around his dick whenever he needed you to. You would willingly degrade yourself in the middle of battle if he wanted. You were addicted to him and you weren’t ashamed to admit it.

His speed increased. He was about to cum. He brought himself all the way to the edge before he pulled out.

“Stick out your tongue, Princess.”

You opened wide as he shot his load all over your face and chest. Your body still bent in half; your feet resting over his shoulders. He took the palm of his hand and smeared his fluids all over you. Rubbing the glossy substance into your skin and pushing it into your mouth. You hummed happily which made him melt. He allowed your body to unfold and laid his full weight on top of you, arms possessively threading around your waist and pulling you close.

You lost your breath. Your mind became a swimming intoxicated mess in his hold. You nuzzled your face further into his shirt while his cum dried on your face and skin. He never undressed. His shirt still on, his pants pulled up. He was a complete mystery to you and now you were invested in solving it. You were his but he was about to be yours just as much. Soon, you’d break him…soon. For now you slept sheltered in his arms.

****************************************************

The next day you both emerge from your room close to noon. The majority of the members of the gang were rough housing together in the common area. All turned still as you came out holding hands with Tobi.

“Holy hell…”

“You two?”

“Are you fucking kidding me?!”

You couldn’t bring yourself to make eye contact with any of them and instead chose to look up at Tobi’s mask. Eyes locked on the face you weren’t sure you’d ever see. Tobi though had a far different reaction. A smug idea popped into his sick mind. It was time to show everyone that you had an owner now and he wasn’t going to entertain any of these brutes trying to encroach on his possession. In his childish voice he called to his comrades.

“Look at my new toy everyone!”

He yanked on your hand so that you were whipped around standing in front of him, your back to the room.

“Y/N, suck Tobi’s cock. hmm?”

“Yes, sir”

It was embarrassing and made your face heat up but you felt your mouth water as you knelt down before him nonetheless. On your knees, you open the front of his robe and untie his pants, pulling out his thick cock.

“What the hell…” you hear Konan behind you in complete disbelief.

You let his pulsing length rest on your bottom lip while you look up at him. His chest rumbles as you slip your tongue out and under his weighty member before opening wide and sliding him all the way down your throat. He grips your hair with one hand before looking up at the shocked faces around the room.

“Y/N belongs to Tobi now. Look how good she’s taking my dick, slurping on it like a good little pet!”

Lewd gargles and squelching sounds came from your mouth as you bobbed back and forth along his cock. He was humiliating you in front of everyone and it was making you wet for him. Your hand came between your legs to rub yourself.

“Aww how precious. She’s even playing with herself for me. You see that everyone?”

You wanted to die from embarrassment but you couldn’t help yourself. The taste of him is addicting. He had you out of your mind.

“Here Princess, let me help you.”

He brings both hands into your hair and pushes you down on him. He thrusts into you at the same time causing you to gag around him. You hear him grumble in delight. You open your jaw and allow him to plummet all the way in. Throat constricting around his tip as it slips past your vocal cords. You hum in contentment, forgetting about everyone watching you. You close your eyes focusing on him and how he feels in your mouth. One hand rubbing your clit more harshly while the other clutches his thigh.

Tobi’s facade almost slipped. He felt high from the way your warm mouth closed around him. He had half a mind to say he loved you. He opted instead to cease talking so as not to give away his cover and instead simply grunted as his hips snapped into your mouth.

The remainder of the room watched in stunned silence at the pornographic scene before them. They watch the orange mask fall backwards, looking up at the ceiling as Tobi was close to cumming. The jealousy Deidara felt had him storm out of the room. Konan had an uncomfortable guilt crawl over her skin but little did she understand, you were in heaven. You whimper as you touch yourself, bringing yourself close to an orgasm. The sounds make Tobi hammer into you faster until you feel his hot spend shoot down your throat. Your walls clench around nothing and you bring both arms to wrap around Tobi’s wait, holding yourself all the way down on him as you hug around his waist.

Tobi so badly wanted to coo in your ear and praise you. Tell you what a good girl you were but he couldn’t muster his carefree sound. Instead he pulls himself out of you and grabs your wrist. He yanks you back into your bedroom and slams you up against the door with the two of you on the other side.

“Fuck Y/N, you’re such a good girl for me. Here, let me reward you.”

You mewl for him, your lip quivering at the return of his deep voice. He twists his mask to the side gaining you access to his lips. You pull them into you while he lifts you up, slipping his wet length between your folds and fucking you against the door.

The banging can be heard by the group on the other side, sitting in the common area.

“Shit…it was supposed to be a stupid prank.” Konan confesses. “What the hell happened last night?”

If only they knew…

Masterlist

#tobi fan fiction #tobi simp #tobi x reader #tobi smut #daddy tobi #akatsuki #akatsuki smut #akatsuki fanfiction #story requests

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