Win of a lifetime

By : UchihaBurger

Disclaimer: I do not own Naruto or its characters

Sakura was on her way to the Hokages office, she was in a hurry, saying the pink haired girl was late for a training session with Tsunade.

The fifth Hokage was a very impatient women. Sakura had been training with the Sannin for the past year. Within that year she had already received a good scalding by being a minute late, let alone the 25 minutes she was behind this morning.

Sakura quickly walked into the Kages office, "Lady Tsunade, I'm sorry!" She bowed instantly. "You better have good reason for being this late Sakura..." Tsunade had a dull hungover look in her eyes.

Sakura opened her mouth, but she didn't know how to say it.

"I was, with someone yesterday, and I had, to, recover..." The pink haired girl tried to explain. The blonde women cracked a smile then spoke,

"Were you with a man?" The Hokage asked a question even though she knew the answer. Sakura stared to her mentor, 'I wonder if Tsunade already knows the reason. It's a test…' The medical student sighed at the thought.

"... Yes." Sakura didn't lie, for she didn't want to get punished for it later.

"Did you do what I taught you?" The Hokage sat at her desk, she leaned over resting her head on her palm. Sakura's attention was diverted to Tsunade's cleavage that was now being housed on her desktop.

"I, did." Sakura was bashfully proud of herself.

"Please tell me you didn't waste it on the Naru guy." The blonde women sighed thinking of the man Sakura had choose to lose her virginity to. Of course, after Tsunade had convinced the pink haired girl to forget about Sasuke her 'rogue' teammate.

"I used it on a someone special.." Sakura turned her head to the side, hiding her blush.

"Tell me who." She raised an eyebrow at her student.

"I don't think I should, Lady Tsunade." Sakura bit her tongue. Tsunade's mind wandered through a list of guys that Sakura would be interested in, 'Definitely not the Uchiha... Especially not Naruto...' Tsunade put her hand up, a sign of her throwing the towel in. "I got nobody." The mature Senju shrugged.

"Kakashi." Sakura blushed from saying his name aloud. Tsunade's face contorted to a straight, blank hungover look. "What do you mean you had to recover from him?" She stood up, her palms flat on her desk. Sakura became embarrassed,

"He was, big... I had trouble getting out of bed, that's why I was late..." Sakura had a chill down her spine from her saying that much aloud. This hadn't been the first time Sakura and her mentor had discussed one another's sex life. Until this point the cherry blossom had been with only her comrade Shikamaru. Sakura had been attracted to him for his intelligence. (Especially after years of being paired with Naruto.)

Tsunade called Shizune into her office, the black haired women opened the door, standing in the middle of the kages office.

"Yes, my Lady." She bowed.

"Get me Hatake, Kakashi." Tsunade pointed to the door.

"Yes." She left quickly, shutting the door behind her.

"What're you doing that for!?" Sakura gasped, throwing her fist up.

"I've never heard such a thing. I always thought Jiraiya was the biggest and the best." She nonchalantly spoke aloud.

"Jiraiya?" Sakura mumbled, recalling the man. She had met him on a few occasions, mainly due to the fact that her teacher and her teammate both had bonds to the white haired pervert.

"Yes. Jiraiya..." Tsunade smiled, keeping one eye closed.

'One of the legendary Sannin. He has to be more experienced than Kakashi...' Sakura was pleased by the thought of the perverted man touching her naked body.

"Sakura, I think you need to meet Jiraiya sensei." Tsunade grinned opening her Carmel eye, little did her apprentice know, Tsunade had lost a bet one drunken night with her old teammate Jiraiya, with nothing left to bet, the kage put Sakura on the line.

"For what reason." She questioned.

"He's very experienced, he'll give you a good reason." Tsunade walked to the front of her desk, leaning on it.

Sakura's eyes opened in shock as the kunoichi realized that her mentor had suggested to seek the company of Jiraiya.

"I can see how you'd be attracted to an older, more experienced man like Kakashi, I mean, you've seen his face," Tsunade snickered. "But imagine a man like Jiraiya, he could really teach you a thing or two," Tsunade shuttered inside as she spoke those words aloud about Jiraiya.

'He's going to owe me for this one, bet or no bet." Senju crosses her arms lifting her breasts.

"Would it be okay if I took the day off from training?" Sakura had been convinced, Tsunade must have had a pleasant time with the Sage if she'd talk like that about him. 

"Just this once, you don't want to fall behind, I'm busy anyway." She replied.

"Where should I look for him at?" Sakura turned to the door.

"Think where naked women would be…" Tsunade tried to hide her disgust towards her fellow Sannin.

Sakura bowed to her master, then turned to the door pulling it open, to reveal the grey haired man Kakashi…

'I completely forgot Tsunade called him here…" Sakura thought to herself.

"Sakura." Kakashi smiled and waved to his former student. This was the first time they'd seen one another since the two had sex, yet the dynamics of their relationship didn't feel like it had changed.

"Hatake, get in here." The Kage spoke.

"See ya." The chiseled man walked past Sakura. She quickly left the office space, closing the door behind her.

The sun shined brightly in the pink and yellow morning sky. The kunoichi was rather surprised that Tsunade had given her former teammates Location away so carelessly. She had found herself walking down a narrow alley that was behind some shops downtown. Sakura decided to take the quickest route to the Springs. 

She figured this is where the pervert would be, saying Naruto had picked up on his godfathers habits…

she was face to face with the brown fences stood tall around the hot pools of water, Sakura walked to the back of the property, searching for the man. "Jiraiya?" Sakura called out to the invisible man.

"Keep it down..." His voice responded, not to far from her location. Sakura found the man as he was peeping through the middle of the fence where a board of wood expanded, and warped a hole.

Jiraiya looked over his shoulder, seeing who would be interrupting him at a time like this.

"Sakura." His body turned to face her.

"Tsunade sent me to find you." She was embarrassed to say the reason why.

"Oh is that right?" His face held a smug look on it. 'That women came through for once.' He grinned.

Sakura was lost for words, she didn't know what to say to the man...

"What?" He sighed, waiting for the girl to speak.

"Wanna come back to my place, for uh, tea?" Sakura could feel her face getting warmer.

"Why not?" Jiraiya stood, looking down at his prize.

Sakura and Jiraiya walked next to one another for the walk to kunoichi's home. The sannin had kept himself occupied by the image of the med ninja infront of him.

'I wonder what Tsunade told Sakura for her to want to invite me back to her place.' The man's mind focused on the lean, kunoichi's hip that swayed back and forth.

The two neared Sakura's apartment. She cleared her throat as she approached her door, unlocking it quickly.

"Come in." Sakura walked into her familiar space, leaving the door open for her guest. Sakura pulled her shirt off, Jiraiya made eye contact with the girl, he quickly entered her home, slamming the door behind him. Sakura had now stripped her clothing off, and laid on her bed. Jiraiya pushed the bedroom door open all the way.

His nose dripped blood as his eyes focused on the tight bodied, young kunoichi before him.. Jiraiya quickly wiped his lip off with his sleeve, pulling his shirts off, the Sage managed to keep his eyes on the naked Sakura.

Sakura sat up, crawling her way to him, making his erection stand in his pants.

"What makes you think you can handle the great Toad Sage?" The white haired man ran his hand through the medical ninja's soft pink hair.

Sakura started to unbutton the older mans pants, his hard cock almost bobbed out his grey pants.

"Wow..." The girl felt the nerves come back. Sakura didn't think it was possible for someone to have a cock that was thicker than her sensei's.

"Let's see what you've got." Jiraiya grabbed a handful of the kunoichis hair, guiding her mouth to his cock.

"I want you to take it all down your throat…" Jiraiya's hand pushed the naive girls head down on his member, Sakura began to gag, her eyes tearing up.

"Swallow my cock." He held her down as she obey. Jiraiya released her head as a reward for tightening her throat around his cock. The pink haired girl took a deep breath in, trying not to cough. The Sannin lightly wrapped his hand around Sakura's throat, leading her to lay on the bed, his hand left her throat, running down her torso to her center.

"Keep those legs spread Sakura." He grinned that familiar perverted smile. Jiraiya's tongue slowly ran over her clitoris, "You're so wet, I've barely even touched you." His finger slid into her tight pussy.

"Master Jiraiya, it's all for you." Sakura made an attempt to talk dirty to the man.

His fingers opened her pussy, allowing him to see the hole that he had to work with.

'That Tsunade really came through. Hmph, your pussy isn't even this tight.' Jiraiya thought to himself while admiring the women before him. Sakura's eyes rolled back as her clitoris was becoming acquainted again with the man's tongue. He had began tracing various shapes and letters. Sakura's back arched as she began to squirm from the Sannins cunnilingus skills, his finger slipped into her tight pussy adding to the pleasure.

"Yes… Don't stop…" Sakura grabbed the bed sheet. Jiraiya could feel her clit begin to swell, he cut contact off with the girl, preventing her to cum. Sakura quickly lifted her head to look at the man.

"Why'd you do that!?" The kunoichi let out in an aggressive tone.

"That's how you repay me? You're quite the brat…" The Toad Sage growled almost as he redirected her head now close to the edge of the bed.

His hand wrapped around his thick and long, cock, "Open wide for me." He spoke lightly, Sakura did as the man said, opening her mouth.

Jiraiya looked into the obedient girls mouth, spitting into her mouth. Sakura laid in disbelief, before the pink haired girl had a chance to speak out, Jiraiya put the head of his cock in between her lips pushing the fat cock into her throat once more, she gagged as the man's balls rested on her face. Her hands moved to push the man away from her face, but Jiraiya was faster, grabbing both her wrists. He released his cock from her throat. She took a breath in, almost panting.

"Are you going to behave little girl?" Jiraiya smirked releasing the women's restraints.

"Yes, Master Jiraiya." Sakura wiped her tears away.

"Come here." Jiraiya put his hand out, Sakura stood in front of the man, his fingers wiped the drool that dripped past her lips.

He leaned over, planting his lips onto hers. His lips were soft, and warm, his tongue crashed into hers as they began to get to know one another, his hand returned around her throat as the kiss became surprisingly rough.

His lips pulled away from the pink haired girls, "Were going to have a bit of trouble getting my cock into you." He ran his free hand to Sakura's wet center.

"I can take it." Sakura had a glisten over her eyes.

"You are being a good girl." Jiraiya deviently smiled. Laying her onto the bed, the Sannin laid on top of the girl. Jiraiya held his shaft as he slowly ran the head is his thick cock over the girls wet opening, covering himself with her natural lube.

Jiraiya slowly thrusted his hips forward, he could feel the girl's tight hole being forcefully stretched by his member.

"Ooh fuck, you're so tight..." The man moaned loudly, thrusting his hips back and forth. The Sannins eyes watched as Sakura's pussy gripped tightly around his huge cock.

"Jir…aiya..." She barley moaned out, "You're going to make me cum…" Sakura spoke aloud.

Jiraiya pulled himself out of her. He wasn't going to allow her to cum, not after all the teasing he did to the girl.

"Come on." Jiraiya grinned pointing to his glistening cock. Her mouth quickly wrapped around his shaft, Sakura forced her head down onto his cock, so he wouldn't have to do it for her.

Sakura decided to use the skill her mentor had taught her, She used her tongue to leave a pleasure filled trail of chakra as her tongue swirled to the top of his erection. Sakura looked up to the man.

"Ooh, I know that move.. Tsunade did sent you, didn't she, auhhh, Sakura-hime." Sakura liked her new title she earned from the man.

"I sent myself Lord Jiraiya." She laid him down onto the bed, Sakura straddled the tall man. He shook his head disapproving, he didn't want her to feel incontrol.

"Stand up," She did as he said. "And turn around." The pink haired girl complied. His fingers wrapped around her left hip as he stood behind her. The man's free hand grabbed the back of her neck, guiding her to bend over the bed.

"Put your knees up too." He stated once more. His hands left her body as she did as he said. With Sakura's body bent over the bed it showed everything the perverted hermit had ever wanted to see.

The Sannin's pointer fingers opened Sakura's tight pussy, he spread her open for him.

"I didn't stretch you at all..." He sighed lightly admiring the small hole. Jiraiya began rubbing her clit. Sakura looked back at the white haired man as she let a moan escape her mouth.

The Sannin's pointer fingers slid into Sakura's still tight pussy, his finger curled inside her.

The Sannin grabbed the pink haired girls ass, shaking his hand to make it jiggle. Jiraiya quickly guided his rock hard member into Sakura. The Sage pushed Sakura's lower back down, making arch her back, as he entered her from behind. Jiraiya thrusted hard, leaving Sakura almost breathless. Jiraiya reached under the girl, pushing his thumb into her bundle of nerves, Tsunade hadn't been the only one to have a trick up her sleeve. As he thrusted in and out of her, his thumb leaked a flow of Chakra.

"That feels so good…" Sakura moaned as her pussy began to pulse. The Sage was going to allow her to come this time, knowing the build up from waiting last the last few times would be way beyond enough pleasure then the girl could handle. Sakura moaned loudly, her head held low, watching Jiraiya's thumb glow a very faint blue ora. She kept moaning, as her muscles tightened and began to pulsate with pleasure, almost like a slow heart beat that vibrates her clit.

The man smiled in approval as he felt pressure build in her pussy.

"Sakura. You didn't tell me you're a squirter.." The Sage pulled his cock out, watching her juices push out her, the tip of Jiraiya's cock was now resting in her slit, he ran it up and down listening to the soaked pussy.

"Uuuhh, yes, yes…" Sakura cried out in pleasure, her body trembling with the pleasure she was feeling from the chakra induced orgasm.

"Hey." Jiraiya stated. Sakura's Head turn back to look at the experienced man that had given her the best orgasm's she had ever received.

"What is it Master Jiraiya." The kunoichi sighed still feeling traces of chakra tickling her clitoris.

"How would you like to do something new?" The white haired tried to hide his smile.

"I'd love to." She naively responded, in a daze of pleasure.

That's all the man had to hear, he ran his cock up from the wet hole, "Hehee…" The pervert lightly chuckled, his eyes locked onto the untouched ass that he was about obliterate.

Sakura's hand reached back, unknowingly spreading her asshole open for the man. His cock began to push its way into the girls tight ass, Sakura gasped in shock and pain as he plunged his fat cock into her virgin hole.

"No, no!" Sakura cried out. She had never had anal sex before and it hadn't been something she was planning on getting into. Until now...

"Oo Sakura this looks so hot, your insides are grabbing onto my cock…" Jiraiya's hand grabbed the young girls hips, forcing her ass to slam back and forth onto the flesh rod inside her.

"Sakura, I'm going to bust in your ass…" Jiraiya's hand quickly left the girls hip and moved to her hair, pulling her head back.

"Cum inside me Master!" Sakura almost dry heaved as she couldn't wait for the man to exit her.

His cock pulsed in her tight ass, Sakura realized through the pain, how good the feeling of the man's veiny member squirting inside her ass felt.

Jiraiya slowly pulled his cock out of the now gaped hole.

"Push my cum out of your ass." He made his last demand. Sakura was hit by a bus of embarrassment… 'Am I really suppose to do that..' The pink haired women took a deep breath, she clenched her ass together, doing as the man told her to do.

Jiraiya smiled in approval as his cum dripped out of her stretched ass over her pussy.

Jiraiya laughed, "I gotta say, I'm impressed by you. It's been a while since I've gotten to dominate a young women." The man stated as he stepped into his grey pants, pulling them to his waist.

Sakura stood from the bed, her eyes wandered to the mess she had made on her comforter.

"Are you leaving?" She almost sounded offended.

"Of course I am." The Sannin pulled his shirt on. Jiraiya walked through her open bedroom door, then left her apartment. 

Sakura walked to her bathroom, turning the hot water on, mixing it with colder water.

'Tsunade was right, I did learn something.' Sakura smirked, then stepped into the warm shower water.