req: ( @rainn-zy ) Have a nice day Moona! Could I ask for a scenario where Itachi and fem reader have their first time in the dark, and then wake up together seeing each other without their clothes on?( I think this is kind of NFSW and SFW?) Anyway, thanks for your attention! Maybe I'm confused or misspelled, English is not my language Beijoos!🇧🇷🍡 (dangos because Itachi likes it)
this is 4.5k long so separate post for my own sanity. also, I went insane while writing this bc I was trying SO hard to convey the cluelessness and the awkwardness of a first time whilst trying to keep it sweet. pls sedate me ❤️.
warnings: NSFW, minors do not fucking interact. fem!reader, loss of virginity (for both), explicit consent, you guide itachi on how to touch your pussy ig, creampie, itachi doesn't last rip him king you tried, you still come tho don't worry, overstimulation (itachi receiving), he activates sharingan. everything under cut!
•••
itachi is a man who's praised and prized for his knowledge, for his capability. he can read his enemies' every move, predict every twist of a battle, every outcome of a plan– always two, three steps ahead.
but here and now, all of that has no use– not when you are on his lap, pressing slow yet deep kisses on his lips that send shivers down his spine. not when you are tangling your fingers in his hair and pulling him even closer, raking every nerve ending of his alight with want, need.
for the first time in his life, this man doesn't know.
he doesn't know what to do, where to touch, how to touch you. he's clueless, and it's neverwrecking, because you are one of the most valuable things in his life– he wants to lavish you with nothing more than the best he can, make you feel nothing but comfort, love, happiness.
and he's been doing a great job of making you happy, of being a good, caring boyfriend. but he's never been a lover before.
the room is dim lit, lights out except for whatever surface the moonlight grazes. and he likes it like this, he likes knowing you can't fully make out his face– how his eyes are a little bit wider from want and his brows scrunched in worry, anxiety.
he wonders if you like it though, would you rather see him? be seen by him?
he parts the kiss but his lips still linger on yours, still a breath away as his thumb caress your cheek. it trembles, you notice.
"I can lit some candles if you'd like," he sounds hesitant and shy even as he tries not to, and for some reason it flusters you.
knowing that itachi, so reliable, caring and capable itachi, is as nervous and clueless about this as you is so very comforting. knowing you're the reason he's this vulnerable also stirs a heat inside of you.
"it's ok," you whisper, trying not to sound as breathless as you feel– what with you devouring his lips and taking every huff of breath from both of your lungs, "I prefer it like this... if you don't mind."
he struggles to hold back a sigh of relief. you just took 50 pounds of worry in weight off his whole body. he relaxes at that, lips faintly tugging at the corners. you can feel the whisper of his smile as he press the kiss to your forehead, chaste and assuring.
itachi doesn't push closer, he doesn't make the next move even though you can feel he wants to, if the slight bulge brushing your thigh is anything to go by. anticipation buzzes in the air and you cut through by entangling your fingers in his hair, it's a gentle gesture, unlike the eager way you pull him in to take his lips in another searing kiss.
his body shivers. your hands are on him, unsure and shaky but still tugging at his clothes, and your lips kiss every thought away from his brain– he can only feel you, smell and touch you.
it's intoxicating how you manage to erase every coherent thought in his head like this, so easily, and it's embarrassing how he's already straining in his pants when his clothes are barely off and you've both barely grazed each other.
you gasp lowly against his lips when he accidentally presses his hips against your thigh and you feel it. your brain short circuits for a second. is that...? that's his dick, right? and he's... hard, he's aroused for you and the realization of it makes your chest heave and you clench around nothing.
it almost unsettles you how wet you're getting so quickly, your panties cling to your skin and nipples are perky and craving for any attention– you need him to pinch them, wrap his pretty lips around and lick, bite them.
"I'm sorry," your mind is foggy with desire, you barely register the strangled apology. but you do register the way he tugs your lips up and leans a bit further away from you and you frown, placing a hand on his cheek.
itachi bites his lip, freezing in place. he's so so glad the lights are off because he's sure he'd die if you could see him now– red with embarrassment and shame. he failed you, he was trying so hard to keep his hips away from you, to hide his embarrassing boner and now he ruined it, right? surely you're nervous like him and this probably made it worse, he should be moving slower, he should–.
he gulps, "I didn't mean–," to hump myself on you like a depraved idiot, he tries to say but clearly struggles.
you interrupt the mess that is his train of thought,
"It's fine," the assurance in your timid voice makes his stomach flutter– from desire, sure, but also adoration. it's like itachi cannot breath without being reminded each second how much he loves you– why he fell for you. "I don't mind, I–" you swallow the lump in your throat but it doesn't make your neck feel any lighter, voice still strained with both anxiety and desire, "I don't mind if you touch me."
you both just need confirmation, just need to know you're both ok with this, that you want this.
and itachi forgets how to breath in that second, because he pants as he leans closer, "are you sure?" there's a pang of desperation in his rushed voice that you've never heard before– makes your stomach leap and the spot between your legs tighten with need.
your fingers curl on whatever flesh they can grip, blunt nails scraping his skin "please."
is desperation too what he finds when he kisses you– plush lips molding over yours, moving in a way that makes you eager for more– proved by how the second he licks at their seam, they part swiftly.
he devours you then and the intesity of his kisses makes you arch into him, a moan escaping and immediately muffled by him. you feel his grip on your hips, firm and tight as it pulls them down against his; the contact makes you whimper, you can feel him now fully– even through layers of clothes you feel the heat and how hard it is against your covered pussy. you can't help but grind into him as you break the kiss, moaning his name.
itachi curses low under his breath, warm breath fanning over you lips as he feels you dragging your clothed core over his bulge– makes every nerve in his body tingle and cock pulse with want.
you feel a weight at the middle of your body and a shiver skims down your spine when you spot his fingers curling around the fabric of the sash keeping your yukata secure. you feel his eyes on you and your hands wrap around his nape, fingers digging into his scalp as you pull his face to yours.
the kiss is much slower than the heated make out you were both having, but it's just as passionate– every movement of your lips sends a pulse down his stomach, and it's all the confirmation he needs to tug the sash away.
itachi parts your yukata with reverence– his breath is held as he guides the fabric down your shoulders, elbows, until it's completely off your skin and pooling at his lap.
his hands are shaking because he can clearly make the shape of your breasts and the faint shape of your nipples– they're perky and hard, aroused and craving attention.
he swallows hard, finger itching to touch and mouth salivating. he's never been this aroused before in his life, it's hard to think knowing you're almost completely bare on his lap, and wanting him just as much as he does you.
"can I–," he takes a sharp breath, trying to steady his voice, "can I touch you?"
your breath hitches and you bite your lip to restrain a low moan, "please do."
his hand, big and firm cups your breast and your eyes fall shut, thighs instinctively trying to clench, stopped by his hips. you can feel your clit throb when he experimentally runs a thumb over your hardened nipple, a broken moan falling from your lips.
"does that feel good?" he asks, hesitant. if the room wasn't this dim, you'd probably chuckle at how his brows are pinched in concentration, his attention completely focused on how he is touching you. he can feel the peeble skin of your stiff nipple and his cock throbs at your sweet moan.
"yes," you manage to breath out, "can you... can you rub it?" you sound almost shy as you ask, and it's cute, he thinks.
he runs his tumb once again over your nipple, this time rolling it around digit and body shudders, "like this?" you moan another yes and itachi groans in response.
his lips run down your neck, brushinv past your collarbones and your stomach flutters the second you feel it on your breasts. he presses kiss after kiss, all the while gently rubbing you perked nipple and squeezing your tit.
but it's when his lips finally wraps around the other one that your stomach tightens with need– you moan his name and your nails dig in his scalp, pushing his head on your chest as you feel his tongue give tentative lick on the perked little bud.
itachi downright moans against your chest when your hips once again start slowly grinding against his and on instinct of taking a sharp breath, he sucks your nipple into his mouth.
your head is thrown back and you whimper in pleasure. you're so wet you can feel your panties clinging to your pussy lips, he's driving you mad and if he doesn't touch you there, you feel like you'll die.
you grab his free, the one that's not deliciously toying with your nipple, and take it to the place rught between your thighs. you press his fingers to the waistband of your panties and you'd be so embarrassed of doing this moments ago, but right now, it only arouses you more.
"can you... c-can you touch me here too?" you ask hesitantly. you're not sure how far he wants to take it.
he has to clench his jaw to stop the most indecent moan from coming out his lips. he can feel the precum right as it leaks out of his tip.
he swallows hard, lips pressed on your skin to keep himself sane as he speaks, "could you... teach me how?"
you nod frantically, almost sobbing before you realize he can see it. you whisper a small "yeah" before you guide his fingers under the waistband of your panties.
his breath hitches and this time he can't stop the moan that hisses out when you press his fingers to your bare cunt.
he can feel you, on the very tip of his fingers– how your damp folds part around them, the delicious heat that immediately pours off you and onto his fingers, and how fucking wet you are.
itachi is worried at this point he might come in his pants at just the feel of you like this– dripping down his and your own fingers as you coax him to skim over your folds, to feel your lips and trace your little hole.
"you're killing me, darling." he whimpers, jaw clenched as he tries so hard to grasp to his sanity while rubbing your cunt.
his chest feel heavy and he can't stop thinking about how wet and hot you are, and how tiny your hole felt. how could he possibly fit his cock inside you?
you shudder on top of him as your fingers lead his higher and you feel tears brim in your eyes when he finally he grazes your clit with the pad of finger; the faint touch makes your thighs clench around his hips, makes you whimper his name and grind against his hand.
your fingers curl on his hair to pull him closer, an anchor, while you try to process what you just felt– his sickeningly sweet heat at the very pit of your stomach that teased a fire even bigger. you were panting in anticipation, in disbelief of how much your body seemed to crave for him to stroke your clit again, rub it until that fire melted out of you.
"there," you plead in a breathless moan, "please touch me there."
and itachi is nothing if not a man devoted to you. even if his fingers are clumsy and touch still tentative, he presses them to that swollen little nub that has you singing moan after broken moan for him, and gets your thighs closing around his hips. he can feel it pulse under his digit and he thinks you feel even wetter than before as you sob his name.
he sucks your nipple back into his mouth and go back to rub the other at the same pace he rubs you little clit, and the coil in the pit of your stomach is almost unberable as you sob. you can feel it, so very close to snapping and in desperation, you grip his hand, tugginv it away from you.
your whole body stiffens in disappointment, but you bite the frustrated moan back.
itachi's face falls, lips bitten in worry as he gently takes his hand away from you and your underwear. "did I hurt you?" there's worry in his voice and you gasp, realizing how that might have looked through his eyes– he thinks he fucked up, that his touch is wasn't wanted.
you try to regain your breath, but your voice still sound unsteady as you hurry to speak, "no, no. it's nothing like that I just–" you swallow hard, already feeling the heat prickling at your cheeks even before you utter the next words. "I... I was close," you admit, voice small and a little bit shy as you press your face against his shoulder– as if he could see you, as if the room wasn't so dark and you didn't need to hide. but you needed the comfort, the closeness.
you find it hard to say the next part, words stuttering even inside your brain.
itachi sounds a bit confused, yet gentle anyway as he leans clsoer to you, a kiss pressed to the side of your neck, "and is that a bad thing?"
you whimper, curling a little bit in shame before you swallow it. "no..."
"but?" he coaxes, pressing another kiss to your hair.
"but I wanted to come with you inside me," you finally rasp out, words rushing out of your mind before you can regret or stutter on them. "if you want that too, I mean," you complete, you don't want to pressure him.
you're completely unaware of how his cock throbs inside his pants at your words, how his tip is leaking for you and how hard he is.
a hand sneaks to your chin then, lifting it up. he grazes his fingers, still damp and coated with your slick, on your bottom lip, coaxing it to part slightly– whether it is from the delicate pressure or from the immediate surprise of him using the fingers he was just rubbing your pussy with, he's not sure, and it truly doesn't matter when it gets a low moan from you. they feel cooler now, but the heat they felt is seared in his mind.
he's panting as he whisper right against your lips, "are you sure that's what you want?"
you could cry then– cry from how considerate he is, and cry from how this fire doesn't stop aching and how much you needed him while not even being able to voice it fully.
"I need you inside me so bad it hurts, itachi," you whimper, feeling the tears slowly blurring your vision as your pussy clenches around nothing, "I want this."
you might as well have ripped the breath out of his lungs by the way he's panting. he offers whatever is left of it to you nonetheless in a kiss, searing and intense, as he pulls you up and on your feet to quickly get rid of his own clothes.
you hear the fumbling as you kiss him, and you part it only to tug your own panties down. you fluster at the way you can feel your slick clinging to it as you finally get rid of the soaked material.
itachi is quick to pull you back on his lap. a shiver licks down your spine when you feel his cock brush against your inner thigh– his skin is hot and hard where it touched you, and you whimper in need.
"I've heard it might hurt in your first time," it takes you second to comprehend what he's talking about, too dazed by your arousal and how close you are to finally feeling him inside you, "please," he cups you cheek and the tender kiss he presses to your nose makes your heart leap, "let me know if I need to stop. I don't want to make you feel pain," his whispered words felt so intimate and assuring, like a warm blanket placed around your shoulders. you think you'll never be able to stop loving this man, and how much he cares for you.
you cup his cheek in return, thumb caressing the patch of skin over his cheekbones, "I will," you whisper to him before taking his lips in another kiss.
the kiss is deep this time, slower and more calculated. he wants to feel every skim of your lips on his, every graze of your tongue. his fingers curl around his cock and he hisses, he's so sensitive the touch almost burns, balls tightening and his breath grows ragged as he guides his leaking tip towards your pussy.
it takes some trial and error before he finally feels your wetness on his skin. you both moan as he slowly parts your dripping folds with the tip of cock. your nails dig in his skin and your hips buck when it accidentally grazes your clit.
you can easily otice he's struggling to find your entrance, you're just as eager as him, just as sensitive and the process almost feels like a teasing torture.
itachi's eyes close shut and a strangled moan falls from his lips when he feels your hand wrap around his, you fingers brush slightly against the his cock and he almost loses it.
you're tugging at his grip, guiding his hand until his cocktip catches on your tight and dripping hole. you moan his name, pleading him to put it in and itachi feels his stomach tightening.
he presses his the head of his cock inside you, feeling your little hole slowly giving in, spreading around him. he hears you panting, feels your body tense for a second before relaxing. your jaw is clenched and you're holding onto him for dear life as he slowly guides your hips down and coax your pussy to take him– he feels so big, you feel your walls stretchinv around him, and ache not painful but unfamiliar, that still the breath in your lungs.
"you're ok?" you don't even notice he stopped moving. even while sitting completely still inside you, his cock presses against your walls to firmly, still spread your tight hole so much.
you take a second to respond, trying to put scattered words together in your hazed brain at the same pace you regain your breath, "yeah," you manage to say, "please keep going."
itachi hesisates for just a second before gradually descends your hips onto his. you both whimper in pleasure and restraint the second your hips finally meet.
you're filled to the hilt, tight pussy squeezing around his cock as it tries to assimilate the thick cock pushing against its every nerve ending. your boyfriend, on the other hand, never thought paradise could be this cruel. you feel amazing, so fucking tight around his cock, he can feel your slick dripping down his balls and at this point he's not sure if it's your cunt clenching around him or his cock pulsing inside you. it all feels good, too good– he won't fucking last.
his balls are tightening in pleasure and the tip of his cock aches and ebbs small but thick beads of precum inside you. you plead him to move and his stomach feels taut, the moment he pulls you hips up and then guides it back down on him he knows he's gone– your pussy drags so smoothly around his cock, even as tight as you're gripping him, you're so wet that he could easily hold you still and thrust hard into you until you're a moaning mess.
if he wasn't on the brink of cumming inside you already, that is. he whimpers your name, almost sobs it when he drags your pussy up his cock once again, "I'm not gonna last," the confession is pulled out him in a strangled moan.
you can feel him pulse inside your tight walls, and you moan lowly, "it's ok. you come," your voice sound so sweet, like a siren singing against his ear, "I want to feel it."
and itachi is gone the moment those words leave your lips– he manages to buck his hips twice more into your tight cunt before his cock throbs and his cum spills deep inside you. the warmth is overwhelming, much like the feel of his tip spurting that much cum inside you. your whole body shudders, and you could almost cum too from how his cock pulses in your pussy as he orgasms, how he moans your name like something holy and how hard itachi is gripping you.
but you don't, your clit still ches in desire and your pussy still squeezes around him, trying to chase the same release.
his head falls against your shoulder as he comes down from his high.
"I'm sorry," it's almost inaudible with the way he's gasping for air, but you can still make out his apologies between his desperate catch of breath, "I– I didn't mean to... you– you felt so good."
you whimper, eyes stinging with tears– you're so sensitive and it feels like you're so very close and so far of the edge. even his words are enough to make your clit throb.
he hisses when your pussy tightens around his spent cock, he can feel your desperation– you cling to him, sob into his neck and to grind your hips against his to get any sort of friction, but his iron grip frustrates every attempt.
he coos at you, heart tightening in his chest– he hates to see you suffer. he presses his lips against your cheek, soothing you, "I know, darling, I'm sorry. it hurts doesn't it? I'll make it up to you, my love," he whispers to you, trying his best to ignore how your pussy keeps gripping his sensitive cock, in order to fully focus on you.
"can you be still for me, angel? I'll make you come, I promise," he will do it even if takes all night and day, but he won't be able to focus if you keep trying to grind your hips against his.
he hears you sob against neck before nodding, a muffled "please," uttered against his skin.
one of his hands leave your hips and he's so grateful when you keep them still, even when he knows how hard it must be for you. he rewards you instantly by pressing his thumb against your clit– and just how you teached him, he rubs it, this time applying enough pressure to cause your eyes to roll to the back of your skull.
your toes curl and itachi slides his free hand all the way to the back of your head and gently tug at your hair, coaxing you lean back, and you do, without a second thought. you're almost laying back as he leans forward, and before you can even think, his lips are wrapped tightly around your nipple, his teeth grazing at the stiff nub as he sucks on it.
the moan that rips out of you is broken and desperate– his thumb is merciless rubbing your swollen clit and the added stimulation to your nipples makes tears run down your eyes. it feels so good.
your pussy is clamping down on him, he can feel you're close even before the moan breaks from you, it makes his cock ache from rhe oversensitivity and yet, he doesn't pull out.
it's his punishment, he thinks– for denying you of pleasure for this long, for getting his before you could get yours. and yet, even as you cunt flutters frantically around his extremely sensitive cock, he can't help but find the overstimulating sensation, his punishment, sweet, especially as he feels yours and his slick dripping down his balls as you finally cum.
he's well aware the dark is meant to keep you both from feeling too overwhelmed by each other's gaze, and perhaps he is cheating when his black pupils dilate into deep bright red, glowing faintly in the dark night. he is cheating as he see you perfectly, eyes closed and every micro expression tiwsted into pleasure– but can he be blamed for wanting to commit it to memory, for craving to engrave you to his memory, just like this, in this beautiful and mindnumbing glory as you come apart for him?
no, no he can't.
his lips brush featherlight kisses onto your skin, from chest all the way to your cheek.
much like you, he's still catching his breath- low pants and gasps fanning across your cheek when he leans closer.
you can also hear it in his voice, the strain of it, the quick intakes of air and yet, there's still remnants of that hunger when asks in hushed breath, "more?"
•••
he wakes up to the nuzzle of your nose against his neck. he chuckles, hands rubbing against your bare back.
"good morning," you whisper against his skin and a small shiver runs through his skin.
he smiles, eyes opening to a room fully lit by the morning sun, and he gazes down at you, "good morning, my love," you lean back to catch his eyes and the tenderness in them makes your heart flutter in your chest.
your head tilts a bit in confusion when his eyes drop down your frame and he immediately averts his gaze, cheeks tainted red. you follow his gaze and immediately feel your own heatening too.
the sheets covering your bare frame had fallen aside, exposing your chest and stomach, probably when you moved back to stare at him.
"oh," you bite your lip, not sure what to say or if you should cover yourself. would he understand it wrongly if you did? would he prefer it? you're about to reach for the fabric when his fingers wrap around your own, effectively stopping you.
he cleans his throat, but he still cannot keep your gaze, and you're sure you've never seen itachi this red before in your life, but the way he speaks to you is genuine, and ends alll your worries on the spot, "you are beautiful."