Work Header

Stolen Virginity

Work Text:

It had taken months of planning and a hard-fought inner battle with his moral compass. But finally, the night had arrived for Itachi, to begin with, his plan. His parents had left him alone with his brother earlier in the evening so they could go for a short term mission outside of Konoha. That would give him two nights and three days alone with his little brother. Plenty of time to do the deed and clean up the evidence after.


After helping his brother finish his homework early and giving him a small dessert, Itachi led Sasuke upstairs and into bed. After tucking him in, he planted a little kiss on the temple. ''Good night Sasuke. I love you.'' Using the dark of the room to his advantage, he activated his Sharingan. 

Sasuke felt his cheeks turn pink from the little kiss he got from Itachi. He softly smiled and looked up with love and adoration into his big brother's eyes. ''I love you to Nii-San.'' Unaware of his brother's plan, Sasuke was defenseless and clueless as Itachi's genjutsu invaded his mind, putting him into a deep sleep within moments.

Itachi swallowed thickly as his brother closed his eyes and fell asleep with the aid of his genjutsu. "I'm sorry, Sasuke. I promise to be gentle.'' Itachi softly whispered as he stood up and turned on Sasuke's bedroom light. Lifting his hands, he made the hand seals needed to make a shadow clone. A soft pop indicated the creation of the clone. The clone left the room to get the items his real self had prepared ahead of time.

Meanwhile, Itachi walked back over to his baby brother's bed and pulled the blankets off of him. As usual, Sasuke had worn his black and grey pajamas to bed. He took a seat down beside his brother and ran his palm over his stomach. That hand slid lower to move across his brother's inner thigh and down to his calf, and he would gently squeeze along the way. 

He needed more.

Itachi pulled his legs up onto the bed and sat Indian style as he slipped his thin fingers under Sasuke's black shirt. He lifted and pulled the cotton shirt up Sasuke's chest, then past his head so he could remove it entirely. With a soft toss, the shirt joined the blankets on the floor. Like most boys, Sasuke's tummy was smooth and flat at his age. His pale porcelain skin accented his dusky pink nipples and made his collar bone pop out against his skin.

'Simply beautiful.'  Itachi thought to himself as he trailed his cold fingers across Sasuke's tummy, leaving behind a line of goosebumps. His fingertips found Sasuke's pink nipples and began to toy with them. He rolled each bud between his thumb and fo-finger, making them peak and harden. The sight alone caused the front of Itachi's pants to tent due to his arousal. 

Itachi bit his lower lip and grunted as he firmly pinched each bud and gave them a firm tug. The rough treatment of his fingers made the once pink nipples stand out a sharp red, nearly purple color after a two-minute-long treatment. At the same time, Sasuke's breathing had grown more profound, and his cheeks had become a flustered pink, and his clone came back with a tray of sex toys that he laid out at the foot of the bed. That was the sign it was time to get serious. Itachi let go of Sasuke's stinging nipples and got out of bed first to strip naked. With the drop of his boxers, his seven-inch hard pale cock bobbed in the air as it stood up straight. His red tip glistened with pre-cum due to his excitement.

He gave his cock a couple of strokes as he got back into bed beside Sasuke. Itachi sunk his thumbs into the waistband of his brother's pants and underwear and pulled down his legs with a single swoop before tossing them to the floor. Itachi's Sharingan eyes were eagerly drawn to Sasuke's smooth crotch. His baby soft, tight, and white sack hung cutely between his legs while his one-inch little penis stood erect due to the previous treatment to his nipples.

Itachi grinned and gave Sasuke's little member a gentle flick with his finger. The older Uchiha leaned over and kissed his brother right on the lips. It was messy and forceful, but it sent tingles up and down Itachi's spine. His teeth nipped and pulled on his baby brother's lower lip. He only pulled away once he couldn't hold his breath any longer.

''You naughty little boy Sasuke. Even when you are asleep, you can't help but love your Anki's touch.'' Itachi purred.

Sasuke seemed to react to his older brother's words as his cheeks darkened further. Itachi was thankful that he had his Sharingan on to record every little detail in perfect clarity. His brother looked like a needy whore in his sleep with the addition of his lips being bruised and swollen, halfway open and wet with spit from the kiss.

Fucking adorable.

His clone made a noise of impatience from the back of its throat. Itachi subtly rolled his eyes at the sound but lifted his brother's limp into his arms. ''I was having a moment with him.'' He softly scolded as he sat on the edge of the bed and adjusted Sasuke, so he was kneeling on his lap, his bottom pushed out. Reaching down, he grabbed his brother's plush cheeks and spread them apart.

The clone opened a jar of vaseline from where he was kneeling at the end of the bed. ''You were thinking about fucking his mouth. That would have left evidence that we can't remove. I'm making sure we stick to the plan.'' He dipped his finger into the open jar and then rubbed it over Sasuke's pink virgin hole, so his rim was nice and slippery. He removed his finger from the crack of his brother's ass and grabbed the 250 mL enema syringe from off the tray and lubed the thin tip with more vaseline.

Itachi subtly frowned because he knew his clone was right. He couldn't allow himself to be weak right now. ''I know, thank you for reminding me.''

The clone slipped the tip of the nozzle between Sasuke's cheeks, then pushed it past his tight sphincter. The lubrication made the entry smooth and painless. Not that Sasuke could feel anything due to the genjutsu. ''One of us has to be reasonable.'' From his spot on the floor, he could see Sasuke's hole clench down around the intrusion. 

The clone pressed the pusher down on the syringe, forcing the warm soapy water to fill up Sasuke's colon. They were going for a deep clean with the size of the syringe they had. They had barely pushed half the water into Sasuke, and Itachi could see and feel Sasuke's tummy begin to grow. But if the twitching of his little cock was anything to go by, Sasuke was enjoying the anal stimulation regardless.

While his clone injected more water up his brother's bum, Itachi gently peppered his brother's lips with little kisses. ''You are doing great Otouto, I'm so proud of you,'' Itachi whispered right into his ear. 

The clone pushed the last of the water into Sasuke's rear and held the nozzle in place as he grabbed the bucket he had brought and placed it under his Sasuke's rear end.

Even under the effects of the sleep-induced genjutsu Sasuke whimpered and moaned into his brother's chest. He pressed his face into the crook of Itachi's neck as a faint grimace passed his sleeping features. Itachi gently squeezed and rubbed his brother's tush as an apology. ''I know Otouto... you will be okay. I promise.''

After a few minutes, the clone finally pulled the nozzle out from Sasuke's rear. A gush of clean water came, followed it, and went into the bucket. ''There, that should make sure he's clean.'' The fully dressed clone stood up and began to clean off the enema syringe.

Itachi held Sasuke tightly and kept his cheeks spread as he emptied into the plastic bucket. Knowing that he was going to be fucking his baby brother's tight ass in just a few minutes had his cock twitching painfully. Eventually, the sound of rushing water ended, and Sasuke's tummy went back to its original shape.
The clone left with the bucket and tray but left behind the jar of vaseline for his real self. ''Don't be too rough with him. You'll have to be gentle with him.'' He reminded just before he left and closed the door.

Itachi's Sharingan eyes remained locked onto Sasuke's plump ass while listening to his clone's final words in all seriousness. ''I know.'' He finally responded in a near-silent whisper. What he was going to do was wrong, but he was doing this because he loved his little brother. He wouldn't dare hurt him.

Left alone at last with his sleeping brother for company, Itachi crawled up the bed and helped his brother lay spread eagle on his stomach. He then laid down between his brother's legs and kissed Sasuke's smooth bottom. Closing his red eyes, he spread those sweet cheeks apart and darted his tongue out, so it licked across Sasuke's entrance. He savored the clean taste of his brother's hole before leaning back down and licking him again. With every little lick and brush of his tongue across his entrance, his baby brother's hole twitched, and his buttcheeks spasmed in pleasure.

That prompted him to slide his hand under Sasuke's front to cup and play with his penis and balls. He wrapped his thumb and fo-finger around his little cock and began stroking him slowly in time with every lick. Itachi pushed his face even deeper between those heavenly cheeks and rammed his tongue against his rosebud. Sasuke's hole resisted the intrusion, but his walls were forced to give way as his tongue burrowed away into his rectum.

Once his tongue was fully inserted, he flicked his tongue up, hitting Sasuke's prostate dead on.


Sasuke's cry of pleasure damn near gave Itachi a panic attack. He feared for a moment that his brother had woken up, but a quick check of his chakra revealed that he was still under the effect of the genjutsu. 

'Is Sasuke enjoying this so much that even my genjutsu can't stop him from crying out?'

That gave Itachi a feeling of hope that he hadn't felt in a long while. Maybe...and just perhaps. Sasuke might welcome this side of him. The long-haired raven pulled his face out from between Sasuke's ass so he could stick his finger into his mouth. Once he had his fingers nice and wet with spit, he gently pushed his finger into his brother's butt.

Another pleasurable groan came escaping from Sasuke's lips as Itachi rocked his finger back and forth inside of him. After a minute of rocking his finger back and forth, he pushed his finger in as deep as he could and curled it, so he ended up pressing hard into his prostate. Instead of getting a cry from Sasuke's lips, he got a full-body jerk as Sasuke unconsciously pushed his ass back onto his big brother's finger.

"Shit, Sasuke, your a little anal slut, aren't you? You like having your prostate played with, huh?'' He teased as he added a second finger. The addition of the digit had Sasuke panting heavily in his sleep, a deep blush covering his cheeks as he weakly rocked his ass against the fingers deep inside of him. His little cock was humping the sheets of his bed.

Itachi scissored his fingers apart to help stretch open Sasuke's inner walls as he jacked himself off with his free hand. He needed to be inside of Sasuke soon, or he was going to lose his mind. Once he felt like he had stretched Sasuke well enough, Itachi pulled his fingers out, to Sasuke's sleepy dismay. After grabbing the jar of vaseline, he opened it in a hurry, scooped out a handful, and lathered his cock with it. With how much he had scooped out, he knew this was going to be slippery.

He usually was able to keep himself entirely composed at all times, even in the most stressful of missions. But here he was gawking in blushing like a damn school girl as he prepared to fuck his little brother. He gripped his slippery cock and guided it to Sasuke's hole. "MmmMhh fuck.'' He forced himself to keep his eyes open as he slowly pressed the tip of his cock into Sasuke's stretched hole. It was a squeezing tight fit even with all the stretching, and his brother's body trembled as his hole was forced open until finally, he sunk inside of his brother's velvet walls.

Like water being sucked up a straw, it was as if Sasuke's ass had grabbed the tip of his cock and pulled the rest of him in one tug. His hips soundly clapped against Sasuke's jiggling buttcheeks.

Itachi felt his ponytail come undone, but he didn't give enough of a shit to fix it. Hell, he had to grab his brother's hips to stop himself from coming right then and there. And it seemed like he wasn't the only one enjoying the experience either. Sasuke was panting and gripping the sheets. His face scrunched up due to the pleasure of being filled and stretched so fully.

"Hehe, you're not even awake, but you're reacting so beautifully. I wonder what you would be saying if you were awake.'' He could imagine it already. Sasuke would be begging for him to move. For more pleasure.

Itachi licked his lip and shifted positions just a little bit to be more comfortable. ''If you want me to move, I'm more then happy to.'' Itachi pulled back until only the tip of his cock remained inside of Sasuke's stretched fuck hole. Then he slammed back inside, ramming into Sasuke's prostate with one definite hit. Sasuke's back arched, and his entire body tensed, his cock spasmed and unleased two small squirts of cum onto his mattress before he fell entirely limp. A stupid smile was gracing his bright red face.

'Did he just...? Did he cum from one thrust?' 

Itachi.exe had to reboot from the utter shock to his system that had been. Like he knew he was a horrible pervert. But for Sasuke to cum in due to one thrust? His baby brother was bred for sex!

Well then, he might as well follow his lead. Itachi's hips slapped and smacked his brother's unconscious ass, the sound of wet slurping filled the room as he de-flowed his princess of a brother. Sweat beaded down from Itachi's forehead, and he felt the bowstring in his lower belly grow tight. A slew of soft curses escaped past his lips as he reached the edge of the abyss. With a cry of pleasure, he came deep and hard into his brother's ass. Shooting ropes of cum deep into his Sasuke's bowels. He didn't stop thrusting until his balls were drained and emptied. Panting heavily, Itachi slid out of his brother with a wet 'pop.' 

Sasuke's hole tried to clench down on something that wasn't there. His open hole was unable to close all the way shut. He was making it look like he was winking at him instead. With a soft smile, Itachi fell onto his side besides his brother and pulled him into a warm and protective snuggle. Sasuke would be sore tomorrow for sure, and he would need to clean them both up thoroughly. But Itachi was fine getting some rest right now.

His Sharingan faded from his eyes as he looked down at his sleeping Otouto. 

''Sweet dreams, Sasuke.''

Itachi laid his head back and slowly drifted off to sleep.


Wait. He never used a condom!