Reader request. Reader is shy and awkward. She doesn't know how to talk to people, let alone big handsome men she has a crush on.

It started out with a simple crush.

You met Jiraiya a couple of months ago. You fell for him quickly. He's nice, even if he is a little perverted. It's kinda nice in a way to be asked inappropriate questions. It's been a while since anyone had taken interest in you. It's just hard to say if he's being fully serious or not. Whatever the case you like his attention. It's just a matter of trying to figure him out.

Plus well... you don't know how to ask. Or flirt. Or really... talk to him. You've only had one boyfriend before when you were just becoming an adult. But even then he approached you and asked you out. And you didn't even go all the way with him. You weren't ready then. You are now.

Perhaps it's why you are seeking out the company in an older man. With all that extra experience Jiraiya will treat you you right. Or at least he can make you... feel those things. Your brain pictures what it would be like to feel his hands touch you. Or his lips against your neck. Or just hold your hand... Take you for dinner. Talk to you all night.

But there's no way he would take interest in you. The most you interact with him is when you watch Naruto train. You care greatly for that boy and you know he doesn't have any family. So you take care of him when you can. He likes your attention and you like giving it. Children are easy to speak to. They don't ask questions that are all that difficult to answer. Plus you've managed to pass on what wisdom you do have. Even if it is just housekeeping, cooking, and taking care of one's self.

It's how you met most of Naruto's friends. You met his team bringing him a lunch. You met his teachers the same way. You nearly melted when you met Jiraiya. Big, strong, confident. He's like... everything you want. But you could barely speak to him beyond a few words. You just become a total idiot around him. You lose your voice. You lose your ability to think. You become clumsy and weird.

And so you tried to rectify the situation. Asking Naruto hardly got you anywhere. All he told you what you already knew. But he did tell you about Kakashi's dedicated reading to Jiraiya's works.

Maybe that could help you. If you read the rather explicit books that your crush wrote surely you'll understand what kind of woman he likes. Not only that you can also learn what to say. It would be nice to maybe get a feel for what this man is like in bed.

There's just one problem with that.

You can't just buy those books. What will people think? These books have a reputation and those who read them aren't good people. They're nasty perverts that can't keep their hobbies to themselves. You'll draw attention to yourself and you hate attention.

You especially don't want Jiraiya to find out. Not right away. He'll think you foolish for relying on his books to ask him out. It's not exactly slick.

So you devise the only plan you can think of. Pull a heist. No one would suspect you of all people to steal but what else can you do? Jiraiya feels too special to let slip by because of your inability to hold a conversation with him. You want him badly. But you don't want him to know that you are kind of a loser. He doesn't seem the type to be attracted to the shy weird girl.

It was surprisingly easy. You went to go watch Naruto train as well as drop off some lunches for him and his team. You kept a keen eye out on Kakashi but it wasn't all that difficult. His pack was in a pile with the smaller more child sized ones. A bright orange cover in the side pocket caught your eye. When the coast was clear you kinda just... yoink. Grabbed it and returned home.

From there you devoured the words on the pages in the span of a night. And you learned a lot. The women in the books are quite different from you. They wear tight short dresses. They have on flattering makeup. They speak confidently in everything they do and seduce the men like sirens.

Man no wonder Jiraiya has hardly flirted with you. You aren't anything like this! You don't have any cute tight dresses or nice makeup. You don't ever speak to anyone with confidence and your track record with men is like a big flat zero that mocks you. But you can try to be. If this is what he likes then you gotta give it a try.

But how to get these things? You can't just go out any get it! Your image! People will know. They'll judge you and you don't want strangers to be all around your business! And what will you say if you run into Jiraiya? It would come off way too odd and strong if you tell him you're getting all this stuff for him. He might figure you for a stalker! You want his opinion of you to go up not down!

Luckily you have some skills in do it yourself. You've hemmed a couple of pants before and a skirt. So turning one of your more modest dresses into something resembling mini skirt territory won't be that hard. It ends up a little lopsided but not noticeable unless focused on. As for the whole makeup situation it can't be helped beyond using what you already have. Now you just have to go try out your new verbal skills.

Naruto often complains that most nights Jiraiya is at the bar. Then he has to deal with a grouchy hung over adult the next day. That seems like a good place to start. Most people hook up and stuff at bars right? That's what the book says. Most of the encounters between the two main characters happen in the bar. After practicing a couple of smiles and posing in certain ways you go out.

...

You flop down on your bed. That went horribly!

Between stammering out half remembered quotes and getting confused looks you wanted the floor to open up and swallow you. You nearly died in there! It was hot and smoky. Jiraiya was already half cut when you got there which was somewhat a blessing since he found you more amusing than stupid. He giggled at everything you said which was nice at first until you realized he was laughing at you.

Then some of his friends showed up and you excused yourself, not wanting to be the weird third wheel nor did you want to embarrass yourself further. You are bad with one on one talk but you're even worse with a group. Kakashi was among them too and he keep looking at you in a way that made you nervous. You didn't want to face a confrontation if he noticed his book was gone.

So you left, escaping when no one had their focus on you anymore. Then to top this horrid night off as you were walking out some stranger smacked your ass and nearly pulled you into his lap. At that point you ran out of there all the way home. The bar scene is a wasteland you were not prepared for.

The only good thing that came out of it was your drunken crush saying you look very pretty tonight. That was the high note then it just crashed and burned from there. You brace a pillow above your head and groan. Eventually you fall asleep.

It wasn't a long sleep since you had opening shift the next day. You just had enough time to wash up and change. Then you do your four to noon in a much more solemn tone. Thankfully you don't deal with much customers in the early morning and have plenty of time to think. Thinking of what to do next. You don't want to give up. Yes you embarrassed yourself but maybe it's because you went about it all the wrong ways.

You need more research material. Jiraiya has how many books in his series? Two or three? It's time to pull a second heist! You punch your fist with determination as you come up with another plan, but you nearly destroyed the tomatoes you were putting out.

During your shift you came up with a plan. Then once you were off you set it to motion. Since you're off so early you have plenty of time to make some lunches. If Jiraiya hit the bottle as hard as Naruto describes then he'll probably won't be hungry until now anyways. And be hungry for heavy foods like noodles and stuff. If there's one thing you know it's hung over people and taking care of them. Being the designated sober person for your friends as a young adult has had its perks. And you know Kakashi will be there too. You've helped him a handful of times with his silent but definitely feeling it hang over.

You skip the makeup to save time and pick out a nice outfit that you can sorta make cute. Like rolling up the shorts into short shorts and pinning them in place. Men like legs right? For some reason they like them shown off. Or so says the book.

The boys were grateful for food. Naruto was chipper as you showed up holding lunch containers. Kakashi breathed a sigh of relief as he accepted his. He looks worse than usual after a night out. He offered you a smile that he usually expresses with his eye and says you look pretty today. But his voice is groggy and he looks a little sickly. Perhaps his drinking companions pushed him last night. He asked you to stay last night but you were so flustered you didn't want to. Maybe if you did he wouldn't look so rough. Sometimes you can be a bit of a... mom. But you're just concerned for people. Especially the day after they drink. They wouldn't be so rough looking if they drank some water between shots.

Then of course there's Jiraiya. He looks a little grey but not that sickly.

"Hey gorgeous! Can't get enough of me, eh?" He greets you as he takes what you offer.

Quick what would the characters say?!

"Y-Yeah you know it." You barely manage to voice yourself loud enough to be heard.

He snorts and smirks but doesn't say anything else. Foolish. That's what you feel. Why can't you do this? Why is it so hard to talk to him?

With a sigh you step back. Your foot crunches on something hard. You turn around to see Naruto's backpack a mess on the ground. Scrolls and weapons haphazardly tossed on the ground near by it. You crouch down and began to organize it. Boys. Always so messy. You glance over to the red pocket book peering out of Kakashi's bag. With the big eighteen plus only on the back cover facing forward you know what it is.

All three of them are absorbed in eating. The hung over adults too groggy and headache induced to really take notice of you. And so you... yoink. Heist complete. Sexy book now tucked safely in your purse. Had you known it was so easy to steal from the copy ninja you'd a done it sooner.

You stand to go home and speed read it but a tug on your waist pulled you back. You land on the grass with your back against something solid and warm. You turn your head to be met with your crush. You're perched between his legs like he's an arm chair. Maybe you should've put on makeup. It could hide at least some of your flustered face.

"Don't leave yet, babe! I haven't had the chance to thank you." Jiraiya cheerfully said.

His arm wrapped around your waist and he pulled you closer. This maybe the time you die. Your limbs feel weak and your heart is beating so hard it may explode.

"Good food. Pretty. You'd make for a good wife." He compliments you. "I know a guy or two who'd love a lass like you."

"O-Oh w-well I uh." You can hardly string words together.

What do you say? That you want to be his wife? That comes off a little strong. You may not know men that well but you know that even that is pretty intense.

Suddenly his amused and rather alluring expression changed to pain. His head jolts down like something fell on it. You look up to see Naruto had whacked him with the now empty container.

"Let her go, ya perv! Can't you see you're making her uncomfortable?"

"Ow! Not the head you little jerk!" Jiraiya shot back at Naruto.

He bat the child away with his container. And Naruto fought back with his. Soon both of them were hitting each other with plastic containers. Kakashi steps in like an over exasperated parent and tries to reason with them.

With all three of them distracted you crawl away before things get messy. They're so childish. How they get any work done is a mystery. You make your way home, slide into bed, and crack open your latest treasure.

There wasn't much more to learn. This book is similar to the the first. There's a couple of new tactics you maybe can apply but it's all stuff you already know.

Now it really feels like you hit a wall. You know all this stuff already. Be flirty. Be cute. Try to apply the situations in the book to you.

Maybe you aren't applying it hard enough...

Somehow you got invited to a party and decided that this was it. A last chance to get this right. You've been failing horribly for too long. You got a whole new arsenal of book study behind you now. You got this. Parties are a good flirty situation... right? There's a scene in the book about a party. Maybe you can do that? But you aren't much of a drinker.

It's a small house dense with people. Mostly shinobi. But they're all in casual clothes and tipsy so it doesn't feel all that exclusive. Since you don't have work the next day you give in and have a few drinks. They taste strong but you'll be fine. A couple of drinks to relax a little won't do that much harm. It's called liquid courage for a reason.

You seek out your crush, hoping to once and for all to get a date out of him. Those drinks have loosened your tongue a little and boosted your set confidence. You got this. You can get this man to notice you. Jiraiya is quite easy to spot in any crowd. Even in something more casual. He's tall and his pretty long hair is eye catching. You stumble into him, catching his arm and holding onto it.

"Heh... hey babe! Hitting the bottle hard already eh?" He asks with a chipper smile.

"N-No I uh... tripped." You say.

He chuckles as he assists you standing up from your fumble. You cling to him, flustered and thinking on your next move. You look around and realize he was speaking to... oh who else? Kakashi. He kindly offered to guide you to the host's house tonight and you lost him in the crowd. Then again you hyper focused on finding Jiraiya. Maybe you should've just followed him if he was going to speak to Jiraiya right away.

"There you are. Maybe you should sit down." He suggests. "You look unsteady."

"I'm fine! I got him to hole... hor... hold!" You bark the word you struggled on sharply. "Hold onto."

"I can have that effect on women." Jiraiya jokes.

"You got that effect on me."

It falls weirdly quiet between them. They both look at each other then back at you. They both seem unsure what to think.

"Let's get you some food." Jiraiya says. He turns you towards the table set out full of snacks. "Absorb some of that alcohol."

"Does this count as a date?" You ask.

"Why not?"

"Yer."

He pulls you along quickly to the table. You look over the food but it wasn't for long. He grabs your shoulders and says your name firmly, gripping your attention fully.

"What has gotten into you?" He asks.

"You..." You reply as your jab his chest. "You gotten into me."

Ye... that was slick. Maybe those books are paying off. This flirting thing isn't so hard.

"No. You like Kakashi."

You frown and shake your head. You put your arms around the back of his neck and try to move in closer. He looks so nice. He always does.

"I like you."

His brows raise as you drape yourself around him. Your cheek pressed against his. Your body so close you can feel his warmth.

"I'm doing all of this for you."

"This? What exactly is this?"

"You like girls like this, don't you? You write about them like this..." You frown at him. Telling him now feels okay. He won't be weirded out. Not when you look like this.

"Wait... You stole Kakashi's books not to get his attention but to get mine?"

You nod. To your surprise he laughs. Then he embraces you more tightly. He finds you rather adorable.

"I gotta say that's the sexiest thing a girl has ever done for me. I'm flattered!"

The air was taking away from you when his lips press against yours. That was quick! The kiss broke and your hand immediately flies up to cover your mouth. Your lips feel all warm and tingly. A good tingly. His lips are soft. He tastes like the donkey juice being served... but on him it doesn't taste bad.

"I've never had someone try so hard and... somewhat fail at it for me before." Jiraiya said.

"W-Well I couldn't do what most other girls can do. I didn't want to seem obvious."

"Ah... I see. Well whatever you did I took notice but I thought you were doing all this stuff for Kakashi."

To him it seemed rather obvious. The change in your clothing. Your demeanour. Always coming around with good food and your loving comforting energy to recharge the group. He figured you were laying it on for Kakashi. Cuz you know... you stole Kakashi's books. It never occurred to the author of said books that you took them because you well... wanted to learn about Jiraiya. He was just trying to be a good wingman!

Kakashi was on the fence about returning your affections and confided with the expert for advice. So Jiraiya convinced him to go for it. Like bro... A beautiful young woman is doing all kinds of things to change herself and get your attention! Go for it. Hence why he was acting grabby around you. That's his true effect on women. If he plays the bad guy in a sense, the guy that always grabs you and says dirty things to you, then you'd retreat to the much more respectful and kinder Kakashi. Honestly he doesn't get women unless he pays for their attention or they are just as odd as he is.

It seems he misjudged you. You are just as odd as he is. Your attempts at flirting with him are... goofy. It's over the top to put it simply. It's a clumsy attempt but thoughtful. It's still more than a woman has done for him before. It makes him feel all warm and fuzzy on the inside that there's a girl out there that liked him enough to try. And he totally missed it!

"But I was flirting with you." You object.

"That was flirting?"

You huff and feel the heat rise to your face. You weren't that bad, were you? He laughs at you again. Then his hand moves under your chin and he lifts your head to kiss you again.

"I gotta say though... I liked you better before you changed up your look."

"Really?"

He nods. You smile.

"I liked the cute nun thing you had going on."

You frown. You aren't that conservative in dress are you? Again you can't think about it too long as your newly acquired lover kisses you again. And again. Soon his hands are exploring your body. You aren't really sure what to do. No one has done this with you before. The kissing in the book isn't so descriptive. It's just the warm up to the more saucy stuff.

"Wanna find a room?" He asks.

You nod. You aren't sure what is going to happen when you get to this room but you want to know. Jiraiya holds your hand as he leads the way. His gaze slides up above your head. There Kakashi was looking back at him. The two men share a look of understanding. With the older of the two being more apologetic. Sorry... but you want him.

He leads you across the house to a thin hallway that ends in doors. Two across from each other and one at the end. The end was a lonely linen closet. He opens the door to the left. Then he pauses and slowly closes it again.

"That one is occupied already." He said with a chuckle.

"Oh my." You respond with a small gasp.

He tried the door on the right and it's an empty dim room. And so you follow him inside. Suddenly a swarm of butterflies grows in your belly when he locks the door. Jiraiya returns to your side and he's kissing you again. Soon you are laying in a stranger's bed and he's on top of you.

Surges of anxiety rise up then fall again a beat apart. You cling to him for comfort. At the moment Jiraiya feels like your only tie to reality. He's keeping you steady. While you hardly have a clue about what you are doing you trust him to guide you. His hands slide under your shirt.

You tensed and the kiss broke. Both you and him are breathing heavily.

"Sorry. Did I hurt you?" He asks.

You shake your head. That felt different than you thought it would. This is moving so quickly but you don't want it to stop. He smiles at you. It's one of understanding. You're nervous and he knows that.

"Just relax."

You exhale a sigh and go limp.

"Not that relaxed."

You tense up again. He chuckles at you. You feel silly whenever he does that. His amusement slowly fades and he looks you over carefully.

"You've done this before right?"

You hesitate. One of his brows arches up. His expression is that of confusion and uncertainty as he tries to figure out what you're thinking.

"It's not a big deal if you haven't."

"Are you sure? I feel silly."

"Don't. You're wonderful. But perhaps it's not the right time to be doing this."

"What?"

Jiraiya partially rolled to sit beside you instead of being propped on top of you. He exhaled deeply through his nose. Yeah he's a big old perv but he's not into partners that are all anxious. Sex is supposed to be fun.

"It's nothing against you it's just... doesn't feel like the right time." He explained.

"I thought you said it wasn't a big deal?"

He turns his head towards you. You fidget with the edge of your shirt nervously as you stare at him. He offers a smile and his hand drifted to yours. His fingers brushed against yours.

"Is it to you?"

"I..." You trail off. The answer was a little unclear. So you go with your gut. "I think it is."

"Okay. Then let's not do it in some stranger's bed in the middle of a mediocre party."

That does sound kinda weird when he says it like that. Maybe this isn't the best place. Maybe you aren't completely ready. It's noisy on the other side of that door. And it smells like smoke and alcohol. You don't truly feel alone with him here.

"Did you want to go back out?" He asks.

"Not really. I'm not good with crowds."

He nods. That he can understand. He paused and looked around. Only one possibility is left.

"Wanna leave?"

"Together?"

"Yeah."

"That sounds nice."

Jiraiya stood up and tugged you to your feet. Instead of the door he went for the window. He hopped out of it first and helped you through. And just like that you escape with him. You hold his hand tightly as you run with him into the quiet night streets of Konoha.

From there, you and your date do things you would never do. Jiraiya pushes you in a way. Your hesitations mean nothing around him. He brings out a side of you that well... you only read in his books. In a way you become like the woman in the story, free and adventurous.

For the first time in a long time you have fun. Complete unfiltered unworried fun!

You dance with him in the streets. You laugh with him. He buys you a cold treat and one for himself. Things calms down for a while as you eat ice cream with him in the warm summer night. You hold his hand and wander the streets with him. It's not so hard to talk to him now. It's easier knowing that's he's always liked you for you. It's a lot easier when it's just him. His arms wrap around you and he raises you up in a hug.

From there you kiss him. He kisses back. The atmosphere shifts as he strokes your back and his fingers graze your ass. He asks a simple question. You nod in agreement.

From there... you take him home. You lead him to your bedroom. Soon he's over top of you as you lay in in bed kissing him. It's much better. It's quieter. It's just him and you.

From there...

It's something out of a dirty novel!