A/N: This is smut and I don't like to censor myself.
4000+ words, get ready for the ride of your life.

...

Naruto breathes in, his eyes still closed, the smell of vanilla reaches his nose. He's slowly waking up from his well-needed nap. He hums as he rubs his head against the warmth next to him. Well, actually he feels a warmth all around him. He feels, good.

"You know, this bed is big enough for both of us and yet you insist on being right next to me," a deep, silky voice mumbles. Naruto hums again pushing closer to the heat. He adjusts his legs so they wrap around it, hugging it close. He's about to fall back asleep until he hears the voice chuckle.

Naruto's eyes flutter open, his brain slow to process the scene in front of him.

Naruto is cuddling up next to Itachi Uchiha, his legs wrapping around Itachi's left leg and his head is on his chest. The older man lies calmly on his back with one arm around Naruto while the other scrolls through his phone.

Naruto's eyes dart around. He's still in Itachi's room. It's plainly obvious with Itachi snuggled right next to him. With that thought in mind, Naruto blushes, feeling embarrassed that he's pressed up against him like this. He's even more flustered to know that he has a bit of morning wood that's pushing at the older male's thigh.

Itachi looks away from his phone and to Naruto to see if he's awake. When he sees the teen's eyes open, he smiles. "Finally awake sleepyhead?"

"S-Sorry!" Naruto squeaks as he unwraps his leg around Itachi.

The older one laughs, and it's music to Naruto's ears. He waves it off.

"You'd be surprised by how often this happens," Itachi says with a hint of amusement dancing in his eyes. Naruto begins to wonder how often Itachi has other guys lying next to him with a boner pressing against his thigh.

"Well, I'm still sorry," Naruto says, but he makes no plans to move from Itachi's warm embrace. He doesn't want Itachi to see his erection and think he's gross, but Itachi can already feel it poking against him. He doesn't mind it and knows that getting a boner is completely normal, but he can't help but think that maybe, just maybe Naruto is interested in him.

The older of the two has a devious thought. He thinks about being a tease to the younger one, he wants Naruto to beg for him, to crave him, need him. His dominant side starts to strip away at his cool and collected demeanor. He's a little ashamed of himself, but not really since sex is a basic need.

While Itachi leisurely scrolls through news articles, the arm that's around Naruto pushes at his lower back. He hears the teen release a short breath from his mouth. Naruto moves his hips slightly to find a more comfortable position, which happens to be his leg around Itachi's thigh, again. Maybe he shouldn't have worn sweatpants today.

Itachi strokes Naruto's lower back. Still no complaints from the younger male. Itachi's testing how far he can go without Naruto becoming upset. Naruto is wondering the same thing.

He looks to Itachi's face, seeing that he's reading something on his phone. He pulls closer to him and places a hand on the Itachi's chest. A faint smirk finds its way to Itachi's face as his fingers brush against the hem of Naruto's sweatpants.

Naruto feels Itachi's drifting lower, but does nothing to stop him. Itachi grabs a handful of Naruto's ass and gives it a playful squeeze. Naruto squeaks, and a dark blush spreads up to his ears. It excites Naruto that someone older than him, and isn't Sasuke but rather Sasuke's hotter older brother, is doing something so intimate with him.

"I-Itachi," Naruto finally says. "What are you doing?"

Itachi gives the teen's ass another playful squeeze before gently massaging it. Naruto isn't complaining, he just wants to know if this is okay or not. He wonders if Itachi is dating anyone, if he's a known cheater, or if perhaps this is all a joke or some hurtful dare that'll get his hopes up.

"I guess I shouldn't be so covert with my intentions," Itachi mumbles as he hits the power button on his phone. He pulls his hand away from Naruto and scoots farther from the teen. "Or perhaps you're not interested."

Naruto, disappointed with the lack of warmth, pushes himself up onto his hands. He looks at the small distance in which Itachi created. It's less than a foot apart but he can't help feel that it's a mile gap. Was Itachi rejecting him? And what's all this nonsense about being interested?

He has to let Itachi know that he does, in fact, want him. He's horny for goodness sake and if Itachi didn't pull away, Naruto was totally going to use his thigh as a humping post! The slight friction with every little movement either of them did felt so good to Naruto, and he can't just let this opportunity slip from him.

Naruto swallows his pride and squeaks out, "I'm interested!"

Itachi gives Naruto a look that makes the younger male squirm. "Really?"

Naruto nods his head. Itachi smirks and leans in close. "Then prove it."

The teen blanks. How in the fuck is he supposed to prove to this hunk of a man that he wants him? He might as well jump out the window now because he's never has had sex in his entire frickin' life! Does he want him to beg? Does he want him to get naked? Does he want him to touch himself? To touch him?

"I have never done anything sexual in my entire life and I'm a total pushover," Naruto confesses with a straight face. "So if you wanna do the dirty with me, you'll just have to do it."

Itachi bites his lip to stop himself from laughing. Amusement twinkles in his eyes as he stares at Naruto's serious looking face. The longer he stares, the harder it is for him to keep in the laughter.

"Pfft!"

Itachi erupts into laughter and this laugh comes from the gut. Naruto realizes how much of a virgin he sounds like and his blush from earlier returns. The older male continues to laugh and rolls to his side hugging his stomach. His shoulders shake as he tries to control his laughter fit. Naruto just sits there embarrassed.

Once Itachi grabs a hold of himself, he sits up on his knees and glances at the little virgin boy, taking note that he's the submissive type. He smiles and says, "You know, we don't have to go all the way."

Naruto nods, his blush still visible. "Right."

"Your first time should be really special, with someone you love," Itachi says as he crawls closer to the teen. "Well, that's what I believe even though my first time was absolutely awful and with someone I hardly knew."

Their faces are twelve inches apart and Naruto looks into Itachi black eyes. They are the same as Sasuke's, but Itachi has better eyelashes.

"Do you want to kiss me Naruto?" Itachi asks and the teen nods. Naruto looks at Itachi's lips, and goodness they are tempting. Itachi leans a little closer, their lips just centimeters apart.

"Then kiss me," the older male challenges. "Show me what you got."

Hesitantly, Naruto leans in and their lips finally touch. The kiss is slow and unsure since Naruto is leading it. He doesn't know what he's doing, but he's trying. Itachi tries to match Naruto's unpredictable speed, but the kiss ends up sloppy.

Itachi is the one to pull away first and Naruto sits there flustered. Itachi studies the younger one's face and smirks.

"You really don't know what you're doing," he comments. Naruto feels shame spread through his chest and up his neck. Is he supposed to know what to do?

"It's fine though," Itachi says pushing away Naruto's concerns. "This is how you kiss."

The Uchiha grabs Naruto's hips and pulls him in for a kiss. His lips move over Naruto's in a slow, sensual manner. His tongue drags across Naruto's bottom lip, but unlike Sasuke, he doesn't immediately stick his tongue in Naruto's mouth.

Naruto mentally takes notes on how Itachi is kissing him, and how it's different from how Gaara and Sasuke kiss him. It's slower and not as sloppy or needy. He takes his time, allowing Naruto to kiss back with the same type of pressure and intensity. It's experienced, like he's a professional kisser.

Itachi pulls away for a brief moment to adjust their positions. He lies Naruto gently on his back as he climbs on top. One of his legs is back in between Naruto's as he lowers himself down.

"Are you okay?" Itachi asks as he places a hand on Naruto's lower abdomen.

"Yes," is all Naruto can reply with before Itachi starts to kiss him again. While Itachi is biting at Naruto's lip, his hand sneaks underneath the teen's tank top and glosses over his skin. His tongue slithers between Naruto's parted lips and pokes at the muscle inside. Naruto's tongue, encouraged by Itachi's, comes out to play and tangos with the other pink muscle. Their spit mingles together as their tongues rub against each other.

Feeling the need to touch Itachi, Naruto places his hands on the older man's shoulders. Itachi's fingers find Naruto's nipple and make circles around it. Slowly, it gets hard and Naruto's need becomes stronger.

Like reading Naruto's mind, Itachi's other hand grabs the hem of Naruto's sweats and tugs down. With his thigh in the way, it doesn't really work out. So, Itachi pulls away, from the kiss, from the nipple pinching and away from Naruto's body.

The lack of warmth makes Naruto shiver. He watches as Itachi places his hands at the hem of his sweatpants and pulls down. Naruto aids him in this endeavor by lifting his hips. Itachi also pushes up Naruto's tank top to expose his torso.

Almost instantly, Itachi latches on Naruto's other nipple, his tongue swirling around it while his hand palmed Naruto's erection through his underwear.

"A-ah," Naruto gasps as Itachi continues to fondle him. Relief and desire wash over Naruto as his hips buck against Itachi's hand.

The Uchiha pops off of Naruto's nipple and leads a trail of saliva down to his navel. He stops all ministrations, only giving little pecks above the waistband of Naruto's underwear.

"What do you want me to do to you?" The question is asked in a silky, husky voice and Naruto nearly melts.

"I don't know," Naruto blurts out, not really thinking. "I just want to feel good."

Being the good dom Itachi is, he smiles at the answer, knowing Naruto won't say anything too dirty since he's a little virgin boy. With one last kiss to Naruto's lower abdomen, Itachi lifts his head.

"How do you ask nicely?"

Naruto gulps. "Please."

"Please what?"

"Please make me feel good Itachi," Naruto says finally without any shame or hesitation.

Itachi hums and tugs at the waistband, signaling Naruto to pull them off. With haste, Naruto pulls his underwear down to his knees, feeling some type of relief now that his dick is out of its confinements. But soon, a panic consumes him. No one has seen him naked like this before. Naruto is insecure about his body but even more anxious about his dick size.

Itachi takes a hold of Naruto's dick and starts stroking it at a slow pace. Naruto releases a shaky breath, the worry about his penis size withering away and a new stress settles on his chest.

His first handjob. What does he do? Does he moan? Not moan? What are the rules?

Itachi spits on the tip of Naruto's dick, applying some type of lubrication. Naruto bites his lip as the pace becomes faster. His hips buck unconsciously and he's not even at the good part yet.

"Someone's excited," Itachi teases as he releases Naruto's dick from his grasp. The young teen whimpers at the lack of pleasure and watches as Itachi reaches into the drawer of his nightstand. He pulls out some lube and shows it to Naruto.

"I hope you're ready."

Naruto nods, watching as Itachi applies a lot of lube to just his middle finger. He spreads Naruto's legs and places the lubed finger to the virgin boy's butthole. Thinking that Itachi will plunge his finger straight in, Naruto tenses up expecting some pain; but Itachi doesn't do that.

Instead, Naruto feels a slight pressure rubbing in circles against his hole. With his other hand, Itachi takes ahold of Naruto's erection and pumps it at a normal pace. His muscles relax as the pleasure makes his thoughts fuzzy. His mind could only think of how good Itachi's making him feel and how badly he wants to come - and he's not even at the best part yet.

Itachi's finger easily pushes pass Naruto's sphincter making the boy gasp. Itachi wiggles his finger to loosen the muscles and Naruto bites back a moan. With care and purpose, Itachi thrusts his finger in and out while also stroking his dick.

Naruto has yet to make a sound besides the gasps and the shaky breaths. Itachi thinks he's not doing a very good job and carefully pushes another finger into Naruto's ass. Thanks to the lube, it slips in with ease. Now, Itachi wiggles both fingers making Naruto whimper and buck his hips.

"Does it feel good?" Itachi asks, genuinely concerned. Naruto nods and finally, he moans out. Relief washes over Itachi now that he knows he isn't hurting him. "It's okay to moan, you know. I want to hear your voice."

"A-Ah," Naruto moans as Itachi starts to stretch his asshole using a scissoring motion. The pleasure numbs his body. All he can feel is Itachi's hands touching the most intimate parts of him, and as Itachi's fingers plunge into him again and again, he feels something absolutely wonderful.

Naruto makes a sound similar to that of a horny female pornstar. Itachi knows exactly what he just touched. It's Naruto's prostate. He ghosts over it again, causing Naruto to buck his hips. Precum oozes from the slit of his penis and Itachi smears it in with his thumb as his other fingers continue to tease Naruto's prostate. He traces around it but never applies a constant pressure to it, which makes Naruto wild.

"Please," Naruto whimpers once Itachi's fingers plunge into him, nearly touching the sweet spot again. Despite Naruto's manners, Itachi continues to be a tease and soaks in Naruto's lewd face as he traces his finger around and around his G-spot.

"Beg for me, and I'll consider giving you the best orgasm of your life," Itachi says before dragging his tongue along the side of Naruto's dick. This is a new pleasure to Naruto, well all of it is, and his eyes flutter close. He feels something hot and wet engulf his penis and his body trembles with pleasure.

His eyes open and meet the intense stare of Itachi. His mouth takes in all of Naruto's length, and luckily for Itachi, he doesn't have a gag reflex. Naruto would've been amazed by this talent if not for the overwhelming pleasure that strikes him at that moment.

Itachi pokes at his prostate, but only once. It's a taste of what awaits him if he just begs.

He moans as Itachi bobs his head and plunges his fingers into him, purposely missing his sweet spot. Naruto can only handle so much and starts to melt into the mattress. His hands find their way into Itachi's black locks and tug at his tresses. He can hardly take it anymore.

"Please Itachi, please oh god, please," Naruto moans out as he feels the fingers inside him dance around his G-spot and stretch him out again. He needs this desperately, and he knows Itachi won't give it to him unless he begs properly. "It feels so good, just please touch that spot again. I want to come!"

Itachi hums in satisfaction while still giving Naruto head, which sends vibrations down his shaft. His maneuvers his fingers to press against his prostate, gently moving in circles. Naruto's head shoots back as his grasps onto the sheets and blankets below him.

Itachi pops off of Naruto's dick and strokes it with his hand again. With his other hand, he presses his thumb against Naruto's taint and applies more force to his sweet spot. Naruto's toes curl and he feels his shoulders shake. His eyes roll back as Itachi proceeds to milk his prostate, his moans becoming louder.

"Ooh, f-fuck, Itachi," Naruto groans as a weight builds in his stomach and his heart rate increases. He tries to control his rapid breathing and this pleasant buildup. He doesn't want to come yet, he wants to hold out for a minute longer.

Itachi pulls his fingers out all the way and thrusts them back in, hitting Naruto's spot directly. His hips buck and his back arches. Itachi does this a couple more times, gaining the same reaction.

Naruto's mind is cloudy, but still filling up with dirty fantasies of being pounded in the ass without any mercy. His throat dries up from all the moaning and the panting, but he can't stop. His body is on fire and every touch makes him tense up or melt.

Itachi eats up every little face the blushing boy beneath him makes. The dominant side of him loves hearing him moan his name and beg for more. He loves it when he makes Naruto's eyes roll back or when he makes Naruto buck his hips. He wants more of this, and he wants this to be one of the best experiences Naruto will ever have.

Itachi licks the head of Naruto's dick before taking it into his mouth again. He sucks on the tip, playing with the sensitive underside while also stroking the rest. He puts more pressure on Naruto's taint, stimulating his prostate from the outside. The angle in which his fingers are at strikes his prostate directly and with such a force that it makes it harder for Naruto to postpone his orgasm.

The pressure in his stomach becomes greater. Naruto is practically drooling from the mouth as Itachi pushes him closer and closer to the edge.

"Oh fu-uck," Naruto curses. A part of him doesn't want this pleasure to end, while another part of him wants to feel that orgasmic finale. "I'm gonna come."

His statement is whiny and needy. Itachi looks to Naruto and sees the teen bite his lip. He quickens his pace and doesn't stop looking at Naruto's face. He wants to watch him come undone, he wants to watch him try to hold back the inevitable but still lose himself in pleasure. It gives Itachi a deep satisfaction to know that he's the one making Naruto lose control of himself.

The young teen moans and he feels something collapse in him. His back arches, his toes curl, and his muscles tense. Itachi feels the walls of Naruto's rectum clamp around his fingers, but he doesn't stop prodding at his prostate. Shivers run down Naruto's spine as his pleasure peaks. His mind blanks and his eyes roll back and flutter close as he feels an explosion rip through his penis and release inside of Itachi's mouth. He comes into Itachi's mouth, and the older male sits there and lets him finish.

Itachi pulls off of Naruto's dick and reluctantly swallows. He lets the teen ride out his orgasm as he continues to pump his still hard willy, which leaks a little bit more cum. Naruto flops back to the mattress. He whimpers when Itachi withdraws his fingers from inside of him.

Naruto closes his eyes and he feels ready for another nap. His body and mind are so exhausted that he forgets that he needs to return back home. Itachi removes his hands from Naruto and stands up.

"Don't fall back asleep," Itachi teases as he heads for the bathroom. "I don't want to have to do this again."

Naruto groans and sits up. Not going to lie, his butt feels gross now with all this excess lube. His body feels numb as well.

I'm gonna need to take another shower. Are his first thoughts as he swings his legs over the edge.

As Itachi is in the bathroom washing his hands, he asks, "How'd it feel?"

Naruto gazes at Itachi with half-lidded eyes and says, "It was amazing. I felt like I was floating for a second. The feeling doesn't last very long though."

Itachi chuckles and turns off the faucet. He dries his hands and walks out of the bathroom. "You should probably pull up your pants."

Naruto finally notices that he's still half naked and fixes his clothing. He stands up, wobbling until he gains his balance. A blush settles on his cheeks as he realizes what just happened. His normal insecure and panicky self returns to the surface.

"I-I'm sorry! I shouldn't have forced you to do that," he apologizes as his whole face bursts into flames. Itachi laughs, thinking Naruto is a funny dude.

"What are you talking about kid? I wanted to do that," he reassures as he waves off Naruto's apology. "Well not really wanted. I didn't plan it or anything, it just sort of happened. I'm just happy I didn't hurt you in the process."

Naruto smiles and is thankful that Itachi cares for his well-being. "Thank you. I had... fun?"

Itachi claps him on the back. "No problem kid."

Something clicks in the older male's brain and he remembers something very important. He goes into his sock drawer and pulls out a stack of money.

"I forgot I need to pay you for cleaning up today, I should probably pay you extra too," Itachi says as he starts pulling bills from the stack. "This should be triple from last time."

Naruto's eyes widen as he's handed the money. "Wait, why'd you triple it?"

Itachi shrugs. "Well, you did a lot more work than last time, and you did it alone too. Plus, I think I should pay you for what you had to endure a few moments ago."

Naruto's cheeks flush as he's reminded of his first sexual experience. He's glad that Itachi stopped after his first orgasm because he doesn't think he could have handled any more than that.

"But," Itachi pauses as he reaches out his hand. "If you don't want it, I'll gladly take it back."

"No, no! I want it," Naruto says, shoving the money into his wallet. His wallet bulges from the amount of cash that's being shoved in it.

Itachi smiles in amusement and places a hand on the younger one's shoulder.

"Let me take you home."

...

Naruto is driven back to his school in Itachi's car rather than that rusty old van. When they pull into the parking lot, some of the students that are standing outside to smoke gawk at his car. Naruto unbuckles his seatbelt and gives Itachi a grin.

"I know this may be weird, but can we take a picture together?"

Itachi raises an eyebrow, wanting to question the teen next to him, but just shrugs it off instead. One measly picture can't hurt, right?

"Fine, sure. Whatever," he says as he poses for the photo. Naruto takes out his phone and snaps a picture of both of them. He immediately sends the image to Sakura, who in return sends him back a bunch of heart emojis.

"I'm totally telling everyone that I just got fingered by Itachi Uchiha," Naruto jokes as he opens the car door. Itachi chuckles nervously, not knowing if he's playing around or not.

"Haha, just don't mention it to my brother," he mumbles, but Naruto doesn't hear him as he exits the car. He closes the door behind him and waves to the older male. The students that are hanging around Itachi's car start to whisper to each other.

"Bye Itachi! Thanks!" Naruto yells as he runs off into the courtyard.

"He's... He's gonna die."

And with that Itachi drove off.

...

A/N: I never know how to end smuts, so this is it.

Sorry if it sucked. I'm not really good at smut stuff, but I needed some smut.
Like, this will all fall perfectly into place sooner or later. Y'all don't know my plan for this story.

Thanks for reading, love you toodles!

*Virgin Boy Butthole will forever make me laugh.