Warning: For Mature readers only! Will have hentai-level smut!

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Sakura huffed as she stomped to Naruto's apartment at sunset. No matter how much of a hero everyone thought he was, Naruto remains the same annoying little brat that Sakura knew in the academy.

They had made some stupid bet last month on what Sasuke would do when he was pardoned. Since Naruto won, he would not stop bugging Sakura about his 'prize.' She had actually thought that the bet was a joke. But from the way Naruto was acting, it clearly was very real.

Sakura had thought that Naruto was over the crush he had on her. It felt like it had been years since he had bugged her for a date, but Sakura now guessed that he just hid his feelings. How else was she supposed to think of the situation when the 'prize' of the bet was for Naruto to fuck Sakura's ass.

Honestly, there was no need for Sakura to honor the bet, mainly because it was ridiculous. But it was worth it just to get Naruto to shut the hell up. Besides, she was pretty sure that Naruto was… small in that area. Sakura hadn't seen it directly, but she had also never seen any sign of a cock in all these years around Naruto. Sakura had seen bulges around that area with Sasuke but never with Naruto.

Sakura decided to give in after realizing that. It would probably feel like a finger was up her ass, and that was a small price to pay for Naruto's silence… literally. Besides, if there was one thing that Sakura was proud of on her body, it was her bubble butt. Her firm cheeks jutted out so much that Sakura sort of doubted that Naruto's small cock could even reach her asshole.

Sakura trudged up the stairs to Naruto's apartment and knocked on his door. Naruto opened it quickly, giving her a bright smile.

"Sakura-chan! Come in! I cleaned the place up just for you."

Sakura rolled her eyes as she walked in. She had to admit that Naruto did clean up the place pretty well. The ramen cups and random dishes that were usually strewn around were gone.

She stopped in the middle of the living room and turned around, tapping her foot, and said, "So? When are we going to do this?"

Naruto had been busy staring at Sakura's tight body, so he was slightly startled at the abrupt question. He asked dumbly, "You want to do it right now? Without any complaints?"

"Are you trying to make me leave with all these questions?"

Naruto raised his palms up in surrender, "Fine, fine. I just thought we should, you know, talk about how to get you comfortable with my…." He pointed down towards his crotch.

Trying not to hurt Naruto's feelings by saying he was too small to make her uncomfortable, Sakura said, "Umm… I think I'll be fine, Naruto. Don't worry about me. I already prepared myself before I came."

She wasn't really lying about that either. There was a benefit to being Tsunade's apprentice that wasn't really thought about. When people look at Sakura, they think of her strength or the fact that she's a good medic. Nobody really goes around thinking that she would be a good fuck, mainly because Sakura didn't have time for it. Still, nonetheless, she knew she would be a good lay.

It wasn't Sakura's pride talking. It was simply her exceptional control over her body. Being a medic was enough, but learning Tsunade's secrets had taken her control to a new level. But as Sakura looked at the excited Naruto, she felt that it was wasted with him.

"Yes!" Naruto pumped his fist, "I didn't know you already got my file from Tsunade-baachan."

Sakura was a little confused with what Naruto meant by that, but she was already being guided into his bedroom, so Sakura didn't bother questioning him. Naruto shut the door behind them and turned Sakura around.

He took in her body for the second time that night. Sakura had always been pretty, even though that was counteracted by her irrational anger. Still, she had really grown into herself as an adult. Her breasts would never be the size of her rival, Ino, but they were perky B-cups that looked perfect for Sakura's body. The thing that attracted Naruto the most, and other guys too, was her delicious-looking bubble butt. It had always been Sakura's best feature, and it only got better.

Naruto wasn't sure what happened in the past year, but her ass went to another level. Before, it was a pair of tight, firm cheeks that would get a second look. Now, however, those tight cheeks that turned into a man-stealing, eye-gaze locking, world-class jutting ass that Naruto couldn't stop thinking about. That had turned into an obsession that Naruto had to get rid of. The way he decided to do so was to destroy that scrumptious ass. Luckily, he had just the weapon to do it, though he might have to try a little harder than expected by Sakura's reaction. Usually, when girls found out, they would steer clear of Naruto in fear. It was almost as if Sakura was used to much bigger cocks than his, though Naruto didn't know how that was possible.

Naruto heard Sakura sigh and say, "Come on, Naruto. Are you just going to stare, or are we going to move this along?"

"Uhh… Alright, but let me ask again. You know about the issue with my cock, right?" Naruto wanted to make sure Sakura knew what she was getting in for.

In exasperation, Sakura gritted her teeth, "Yes already! Stop stalling, and let's do this."

At this point, Naruto shrugged and proceeded to take off his shirt. He was about to do the same with his pants, but Naruto noticed that Sakura was looking at his well-formed abs with a hit of pity and disappointment. This was honestly a little weird since Naruto knew that he looked good.

With a frown on his face, Naruto reached out and grabbed Sakura's hand to pull her towards him. He held Sakura against his hard body and grabbed her ass with both of his hands. Naruto's finger sunk into the soft ass-flesh as he mauled her bubble butt.

Naruto humped into Sakura while staring down into her green eyes and said, "Alright, seriously, tell me what your problem is! You're acting super weird!"

Sakura felt his hard cock rubbing into her lower stomach. It was even smaller than she had thought… As Naruto's finger dug into the crevice of her ass to grasp her meaty cheeks firmly, Sakura bit her lips and said, "Are you sure you want to do this, Naruto? Maybe we can stop and forget that this ever happened."

Sakura thought that she was doing Naruto a favor by saying this. He was feeling up her ass, so Naruto had to have known that his tiny cock could never reach her asshole with her jutting cheeks in the way. Sakura thought she was simply being a good friend by giving Naruto an out so he wouldn't get humiliated.

Naruto, however, finally found this reaction to be the most normal. For entirely different reasons, of course. With a grin, he said, "No way in hell I would ever do that, Sakura-chan! I have you exactly where I want you!"

With a tiny shrug, Sakura then said something that she would regret, "Fine, do what you want then. If you want to have any chance to get in, make sure you go hard and fast."

Sakura thought that was the only way a cock smaller than her finger could ever hope to get the tip inside. She didn't notice that Naruto had frozen when she said this, but she did realize that he was shaking a second later.

What Sakura was feeling from Naruto was excitement. No girl had ever told him to go hard. It was always a 'go slow,' or 'pull out.' Now the girl with a world-class bubble butt like Sakura was practically inviting Naruto to destroy her. If she wasn't still in love with Sasuke, Naruto would have fallen in love with her all over again.

"You got it, Sakura-chan!"

That was the last thing Sakura heard before she was pushed onto his bed. She idly thought that Naruto must have washed his sheets with how good they're smelling. There wasn't much else to think about as Naruto pulled up her signature red-qipao dress to reveal her bubble butt in skin-tight shorts.

Naruto knelt behind Sakura, buried his face in between her jutting cheeks, and rapidly moved his face side-to-side. It made Sakura squeak in surprise when she actually felt Naruto motorboating her ass. She knew that guys did this with women with larger busts, but it's the first time Sakura realized her ass was big enough for the same treatment.

Naruto used her hands and spread the clothed cheeks, licking around the asshole before leaving with a small kiss right on top of her covered hole. He stood up and rushed to get his clothes off before ripping off the clothes that dared to hide Sakura's body from his eyes.

Sakura briefly turned around in curiosity about Naruto's cock. What she saw was a barely 4-inch fully hard cock, not very encouraging for Naruto's chances to get inside her asshole. She turned back around to save Naruto the humiliation of her looking at him while he failed.

That was a mistake on Sakura's part, a big mistake. You see, while Sakura had Tsunade as a teacher, Naruto had Jiraiya. He didn't get anything special like Sakura did with Tsunade for being Jiraiya's apprentice, but what Naruto did get was sealing expertise. When Naruto was a growing teenager, Jiraiya had noticed something strange when Naruto was training. He was moving around in increasingly weird movements that made Naruto an easy target for enemies.

It had taken a few weeks for Jiraiya to find out the monster of a cock that Naruto had started to gain after hitting puberty. It was so damn large that Naruto couldn't do anything without it getting in the way. Jiraiya, being a seal-master, made something for Naruto that would make his cock a non-issue outside the bedroom. There was a side-effect built into the seal, though. It wasn't something that was a natural side-effect for this type of seal, but it was explicitly built-in by Jiraiya from his jealousy of how big Naruto's cock was.

That built-in side-effect would make Naruto small. Like really small. Like reducing his 18-inch bitch-breaker to a below-average 4-inch cock.

That was what Sakura didn't know, and if she looked at the medical file like Naruto thought she did, Sakura would have been much more careful. When she turned back around to 'save' Naruto some humiliation, Sakura wouldn't know the true size until his cock was inside her asshole. On top of that, Sakura had told Naruto to go 'fast and hard.' Yea… she would be in for a surprise, to say the least.

Naruto licked his lips as he grabbed one meaty cheek and moved it to see her winking asshole. It really did look like she had prepared herself for his cock. Naruto could see something like lube glistening on her hole.

Naruto released the seal on his cock, his tiny pecker growing into a monster that towered over the slender Sakura. If she didn't have such a fuckable ass, Naruto would have never considered this. His cock was as thick as his forearm and was just as long. If Naruto lined up his cock, with his balls touching Sakura's pussy, his cocktip would reach above her belly button. Anyone else would need extreme care while being fucked by something so big, but Sakura was a medical-nin and Tsunade's apprentice to boot. She had all the skills necessary to take his whole cock and more.

Naruto climbed onto the bed to stand above Sakura and pointed his monster cock at her tiny asshole. He gave her one last warning, "Are you ready, Sakura-chan? If you want to stop, now is the time because when I get inside, I won't stop till you're a gaping mess."

Sakura put her face down into the nice-smelling sheets and rolled her eyes hard. Naruto was always a boaster, but he had to know that his cock was pathetic, right? With a sigh, Sakura told him, "You can try Naruto. That was the bet's prize so let's get this finished quick, okay?"

Naruto raised his head and clasped his hands together to thank the gods above. He then crouched a little, so his cock was almost touching Sakura's ass before steadying himself with a hand pushing down on her upper back. Naruto stroked cock one last time, a dollop of precum landing on Sakura's hole, and took a deep breath.

The next few seconds were blank in Sakura's memory. Try as she might in the future, there was no way for her to remember exactly what happened. But the moment after was searing into her brain.

Following Sakura's instruction of 'fast and hard,' Naruto used all of his considerable force to get his throbbing bicep-thick cock inside Sakura's tiny asshole. While it was difficult, Naruto mounting Sakura like she was a bitch certainly helped. With the help of gravity and his own muscles, Naruto unexpectedly found himself balls-deep inside Sakura. The sound of her asscheeks slapping against his crotch reinforced that fact.

Naruto groaned loudly as his cock was held in a vice-like grip by Sakura's spasming asshole. He could barely pull out his cock from the grip that was holding him in. Strangely, Sakura hadn't made a peep from having her ass stretched beyond its limit. Just when Naruto thought that Sakura made some kind of preparation that could let her take his massive cock with no problem, a wail erupted from her mouth.

"OH MY FUCKING GOD!"

Naruto smirked. There it was. Grabbing her hips to keep her ass in place, Naruto pulled out a few inches before slamming back in, drawing out another scream from Sakura.

"USE YOUR DICK NARUTO! NOT YOUR ARM, ASSHOLE!"

Giving her another mind-melting thrust, Naruto said, "This is my cock Sakura-chan."

Sakura was shunted forwards when Naruto speared her ass again. She clutched the bedsheets for some sort of grip while turning her head back to look at what was fucking her ass. Sakura's eyes widened when Naruto was telling the truth. It really was his dick that was pounding her tight ass, even though Sakura had no idea how the tiny cock she had seen turned into this bitch-breaker. A squeal left her lips when Naruto started to fuck her ass with more inches of his cock.

Naruto slammed his hips and stayed glued to her ass, flattening her jutting cheeks. Sakura's initial thought of her ass stopping his cock was brutally disproven with the force that Naruto was using. Sakura flailed when Naruto lifted her lower body, standing up on the bed with his cock still balls-deep inside her body. Luckily for Sakura, Naruto planted her on the bed with her knees raising her ass in the air. It was the face-down, ass-up position that Naruto thought would make it easier to fuck Sakura harder.

"Naruto! Wait!"

Naruto rolled his hips, closing his eyes at the pleasure of stirring up her insides. He was far too gone to listen to Sakura right now, and he did warn her that he would stop before her ass was gaping.

For the next thirty minutes, the bedroom was filled with the sound of Sakura's ass being slammed into by Naruto pounding hips, along with Sakura's screams of pleasure and pain.

No woman could take a cock like this without feeling some pain, but Sakura's medical-nin skills really did pay off here. She was surprisingly hit by a continuous stream of pleasure from getting her ass stretched and destroyed by this monster cock. Sakura's pretty face was lying on the bed with drool coming out of her mouth, her eyes almost looked blank, with the only sounds she could make being screams and moans.

"I almost forgave you, Sakura," Naruto said while relentlessly using her ass as a cocksleeve, "All the times that you hit me when we were kids. When you kept choosing Sasuke over me."

Sakura's legs gave out from the constant ass-pounding. Naruto didn't let that stop him, so he followed her down onto the bed and laid on top of Sakura's prone body. He gave a few jabs into her ass and loved this feeling even more. While the position before let Naruto get deeper into Sakura's ass, this prone-bone position gave him a dominating feeling. Like all Sakura could do was take what Naruto gave her.

This gave Naruto a new life, making him somehow slam into Sakura harder. Her ass was turning bright red by the constant abuse it was getting before Sakura let out a loud, high-pitched squeal. Naruto was just doing his job of destroying the bubble butt below him when he felt a gush of liquid spray onto his swingings balls and bed.

Curiously, Naruto turned Sakura face to him with a grip on her pink hair, and what he saw excited him. Her face had that fucked-stupid look that Jiraiya loved to write into the Icha Icha books. Naruto didn't think that was possible, but it looked like he had actually put it on Sakura's face.

"Holy shit Sakura-chan! I didn't think you would be such a fucking slut! I just wanted to ruin your ass, but you're actually enjoying it!"

Naruto pumped hips up and down rapidly, making her asscheeks bounce and wobble from the beating it was getting. He wanted to get another analgasm from this pink-haired slut.

"Shit, are you going to get addicted to my cock? I don't love you anymore, Sakura-chan, but I'll gladly ruin this ass whenever you ask."

Poor Sakura was in no state to answer back to Naruto's taunts. Her mind was far from being able to make a coherent sentence right now. All that was let out was a strangled moan as her pussy gushed out more femcum.

Naruto had been railing Sakura's ass for a long time now, and her ass spasming around his thrusting cock again brought him to an end. Naruto buried his cock deep into Sakura's guts with a thunderous clap and unloaded an ungodly amount of cum.

Sakura's ass was filled with stream after stream of Naruto's cum for what felt like minutes. She moaned deliriously as her body somehow kept taking more and more of it without being able to expel any, mainly because of Naruto's cock acting as a plug. In the reprieve of her ass getting pounded, Sakura could finally say something that wasn't a scream or moan for the first time in a while. But, unfortunately for her ass, it was something that turned Naruto on even more.

"HNNNG! OH MY GOD, YOU BLOATED MY STOMACH! I LOOK PREGNANT!"

Naruto stilled on Sakura's back before he abruptly turned her around on his cock to lay on her back. Naruto stared at the formally taut stomach that now looked a few months pregnant, and it was because of the cum he had dumped into her. Sakura got a little nervous at the look in Naruto's eyes and stammered out, "D-Don't get any funny ideas, Naruto."

Naruto stroked her stretched belly and said, "I don't think it's funny at all. In fact, let me show you how unfunny it is."

He abruptly picked up the lithe Sakura and got off the bed. Sakura watched helplessly as she was held in his arms and moaned when Naruto actually pulled his cock out of her ass. They both watched the bloat from the cum reduce a bit when it escaped from her unplugged ass. It didn't last long, though, as her ass soon regained its former tightness, courtesy of Sakura's preparation beforehand, and locked the remaining cum in her ass.

Naruto looked at Sakura incredulously and asked, "How the fuck are you not gaped out yet?"

Even though she looked like a bred-bitch, Sakura said proudly, "My med-nin skills aren't just for show. Even with your monster cock, I won't be affected for too long."

Naruto gained a weird look in his eyes before he looked back down to her bloated stomach. He experimentally pressed down on her belly, and a spurt of cum shot out of her ass. Naruto smirked and pressed the rest of the cum out quickly. He had plans for the so-called skills to be put to the test.

Naruto threw Sakura back on the bed, leaving behind a puddle of cum on the floor as he followed her. Naruto grabbed Sakura's long legs and pushed it up her body, practically folding it in half into a mating press. Of course, Naruto wasn't going to be fucking Sakura's dripping pussy, so he had to push a little harder to get easier access to her asshole.

It was still a marvel that her ass regained so much tightness that quickly, but it would be Naruto's pleasure to gape it once again. He looked at the nervous Sakura and asked, almost rhetorically, "Are you ready, Sakura-chan?"

"For a cock like yours? How can anyone be…."

Sakura was interrupted by Naruto slamming his cock back inside her ass. His fat balls slapping against her firm asscheeks. Sakura opened her mouth, and a shrill squeal/scream almost broke the windows of Naruto's room. He didn't particularly care about that because he saw something glorious.

Naruto could see the outline of his cock in Sakura's stomach. He laughed proudly, "Look down, you anal slut! My cock's so big that you can literally see how deep it is inside you!"

Sakura whimpered at the shaft that was bulging her midriff. She bought up a shaky hand to feel the bulge appearing and disappearing rapidly in tune with Naruto's thrusts.

"Ugh, yeah, that's it, Sakura! Stroke my cock while I fuck your ass!"

For once, Sakura did as Naruto asked. With his cum-filled balls slamming down onto Sakura's bubble butt, his 18-inch cock impaling Sakura's ass, the addition of her hand stroking his pounding cock through her stomach was all Naruto needed to fill Sakura with more cum.

Sakura felt his balls twitch against her ass and reached down to rub her engorged clit. Naruto didn't fuck her long enough to make her cum this time, and there was no way in hell that only he would get to orgasm.

By the time Naruto started to hose down her ass with his second cumshot, Sakura's eyes had rolled back into her head and squealed as she squirted her juices on Naruto's chest.

"Fuck Sakura. You're the perfect fuck-puppet! I could have been destroying his ass for so long if you just gave in just once!"

"HNNNNG! Shut up! Even if you have a donkey-dick, I still love Sasuke-kun."

Naruto ground his hips into her soft asscheeks, and his eyes glinted. He didn't really care about who she loves, but it wasn't proper etiquette to talk about other men when you have another man's cock deep inside your ass.

"I think I should teach you a lesson Sakura-chan. You've been an angry bitch for so long that I think only a cock like mine can fix your attitude."

Sakura's following words got stuck in her throat. The sudden restart of her ass getting pounded stopped any further conversation. It felt like her ass was railed in different positions for hours... because it was.

Naruto had first stretched out her ass late at night. But when Sakura finally felt multiple loads of cum expelled from the confines of her ass, she could see the faint rays of sunlight peeking through the windows. Naruto had been fucking her nonstop for hours upon hours, trying to 'destroy' her ass as he promised himself. But whatever he did, it seemed like her asshole would go right back to the delicious tightness it had previous to Naruto railing her. This was enjoyable for both Naruto and Sakura since Naruto would go right back to fucking her again. Still, it wasn't what Naruto wanted to end the session with.

He stared down at the heavily-breathing, sweaty, well-fucked Sakura pensively. If hours upon hours of anal stretching didn't do the trick…. what about two cocks doing the stretching at the same time? Naruto hesitated a little, not because of any concern about Sakura's ass taking too much cock, but the fact that his cock would be touching another… even if the other cock belonged to a shadow clone. Eventually, Naruto decided he had to do it. He had to see Sakura's perfect ass ruined.

A clone of Naruto appeared in a puff of white smoke. Sakura tiredly looked towards the sound and saw two identical, massive, bitch-breakers standing ready for action. It took her a while to realize what he wanted to do, but when Sakura did, an intense look appeared in her eyes as she rasped out, "Do it. I fucking dare you to do it."

Without a word, Naruto lifted Sakura's body and impaled her once again on his cock. Even though she had felt this dick rearrange her insides all night, it still made Sakura squeal a little before she got used to it. Naruto pulled her body down, so Sakura laid her upper body flat on him while still straddling his hips.

Sakura looked back at the clone stroking its cock behind her and bit her lips before nodding in approval. To help Naruto out in his quest to destroy her ass, Sakura reached back and spread her cheeks for him. Inviting him into the already occupied hole. She was a little curious about how they would do this, and while it might hurt if they succeed, Sakura knew that the pleasure she would feel would far outweigh any pain. Thank god for Tsunade-sama's teachings.

The original Naruto winced when he felt the clone try to jab his cock into the hole he was filling. Naruto tried to forget about what he was feeling by staring at Sakura's face. She was wincing and flinching whenever the clone gave her asshole a try. It had to have been ten minutes before Naruto felt a change.

Sakura's eyes went wide. She held her breath as Naruto somehow felt her asshole getting tighter than before. He could feel the clone getting inside, and as long as Naruto could focus on Sakura's pretty face, he could get through this.

Sakura's face was bright red from the pain she was feeling. Her previously tiny asshole was being reamed by two bicep-thick cocks at the same time. And the crazy part? Sakura could feel the pleasure following right behind the pain. She just had to hold on a little longer.

When the clone's cock was halfway in, Sakura couldn't take it anymore and let out a shrill scream. It was so loud that Naruto was sure that the whole village could hear Sakura getting destroyed. The clone actually gained a concerned look and moved to pull out, but Sakura stopped him.

"DON'T YOU FUCKING DARE! I can feel it right around the corner, and if you pull out now, I swear I'm going to cut both your dicks off!"

Both Naruto's looked stunned before Sakura barked out in pain, "DO IT! Go all the way! NOW!"

That's precisely what the clone did. The original Naruto below should hear the thwack of Sakura's fat ass hitting the clone's hips. Sakura seized up and spasmed, falling limply on the original Naruto as she came her brains out. She had the strongest orgasm of the night by two impossible cocks sheathing themselves into her tiny asshole at the same time.

The two Naruto's looked at each other before they started pumping into her ruined ass, trying to get their own orgasms. They could both feel Sakura's body twitch every few seconds from the mini-analgasms she was having, her pussy constantly gushing out her femcum as they railed her ass.

Simultaneously, they both slammed deep inside Sakura's ass and seed her with double the amount of cum compared to the previous loads that were shot into her. All Sakura could let out was a small whimper as her asshole was used as a cumdump. Eventually the clone had given everything that it had, and popped out of existence.

Sakura's pussy gushed again when her asshole closed tightly around the remaining cock that was left inside. Naruto loved the tightness, of course, but his brow twitched when he realized that even two monster cock might not have been enough to gape her asshole.

Naruto struggled to get out from underneath Sakura and pulled his finally-softening cock out of her abused hole. He stared intently as Sakura moaned while cum poured out of her unblocked ass. This time, her ass didn't tighten up fully. There was a steady stream of cum that was pouring out as her bloated stomach deflated.

Naruto pumped his fist in excitement, and he gave Sakura's bright red asscheeks a hard slap in celebration. Sakura just twitched in protest on the bed.

"Debt fulfilled Sakura-chan! But what do you think about making this a regular thing? I think we both enjoy trying to break your ass."

Sakura mumbled something that was muffled by the cum-drenched bedsheets. Naruto just shrugged and decided to ask her again when she didn't have cum pouring out of her ass.

I have a lot more stories posted on AO3 under the same name. I'm slowly uploading everything on fanfiction, but it'll take time to catch up.