Jiraiya x Reader Stories(Smut)

Shy

This was a request. A shy young reader has a huge crush on Jiraiya. But she finds it hard to talk to him and all that jazz. And to top it off she's a virgin and knows nothing about sex. So she's really scared of it but doesn't wanna come off as a loser to him. No full sexy times mostly teasing and fingering.
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It's tougher than it looks. Most people think being the shy type was an easy life, but honestly it was hard sometimes. It's hard to speak. You can't even look people in the eye for too long without feeling weird. You shake when too many people look at you. But you just might pass out and die if you get stuck under Jiraiya's gaze for too long. You like him a lot! He's just so... perfect. Maybe that was an overstatement to some, but they just don't get it! He's really cool! Handsome, brave, strong, outgoing, and funny. He has this great laugh that's so loud and intoxicating. Everyone in the village seemed to be drawn to him. He had the natural charisma of a leader. He's everything you aren't. That's what makes him so great to you.

You are so shy and awkward he's probably never given you a second glance. He always smiles at you and greets you when he walks past your desk. But nothing more. You are essentially a fancy secretary. One of the only civilian jobs in the Hokage's estate was being an aid for the Hokage. It's just a fancy way of saying you organize papers, schedule meetings, and bring the old man some tea when he asks. But it meant you got to see Jiraiya almost everyday. He was quick with his missions and you are sure he shows up half the time just to heckle his old teacher. He stops to talk to you more often now.... after a month or so. Even after that long you get so flustered you can barely hold the conversation.

Maybe the universe is laughing at you. They want you to squirm and suffer because you are too shy to even talk to this man normally. You mumble and stammer. You fidget and try to find anything to do with your hands to keep yourself occupied when he talks to you. You use your hair to hide your face and know what his feet look like more than his face. You're just so nervous around him. Because you like him so much. You've developed quite the crush on the famous Toad Sage. Which made it like several times harder to speak to him.

Much to your utter shock Jiraiya asked you out one day out of the blue. You were so stunned. You just stared at him for a moment before nodding aggressively. He smiled and enthusiastically said he'd meet you outside of work to pick you up at the end of your shift. You were so excited. You got your work done and signed out at the end of your shift exactly on point. You stood outside of the estate with your eyes peeled for your date.

Then he was late. As the minutes passed, doubt began to crawl all over you. He's not coming, is he? He must have just been teasing you. Plenty of people do. You stare at your feet, feeling dejected. You feel like crying. You really believed he liked you too. This was your big break to get a first date. Maybe it's a bit late to start in your twenties... but you just hadn't found the right person. It felt like the opportunity was slipping through your fingers right before your eyes.

"You're still here!" Jiraiya puffed.

You look up. He looks out of breath. He's panting in big breaths of air and flushed. There's still dust floating around his feet from how hard he kicked it up. He whewed and smiled at you.

"I am so sorry! I got caught up with something." He apologized to you. He paused and made a face. "You know what, you wouldn't believe me if I told you why. Let's just get to that date, shall we?"

"You're sure you still want you?" You asked quietly. Needless to say you don't feel so confident about this. A part of you is still sure he's going to laugh at you and walk away.

"Huh? Of course I do. I said I would." Jiraiya tilted his head ever so slightly in question. He looks you up and down. You look so crestfallen and be wants to fix that. He gave you a cheeky wink. "Unless you got second thoughts, I still wanna paint the town with you."