Jiraiya x Reader Stories(Smut)

Try Try Again

A request. Reader is a socially awkward girl who steals Kakashi's books in an attempt to learn how to seduce Jiraiya. Hijinks ensue

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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.