A request from a lovely reader. An incredibly shy virgin reader that caught Jiraiya's eye. They date and she doesn't admit to him that she's a virgin until he accidentally put pressure on her as she was deeply embarrassed by it and didn't want him to think less of her.

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."

He offers you his hand. You take it and he leads the way into the nighttime hustle and bustle. It's nice holding his hand. It's warm and a little calloused, but not at all bad. You are red to your ears but you can't stop smiling. He takes you to a casual restaurant that you feel at ease in. It's not stuffy or quiet to make things intense. It's not too crowded and you are on his undivided attention. He's shifting around in his seat like an antsy child as he happily orders for you and himself. He knows you're shy. He doesn't mind being your voice. He's just happy you agreed to go out. He hasn't been on a date in so long and you are just so darn cute.

The date went very well. You were still too quiet than you would have liked. But Jiraiya must have had a good time, because he asked you out again for the next night. You agreed. It just went on from there. More dates. More genuinely good times. But... something still bugs you.

"Why do you like me?" You ask.

"Hm?" Jiraiya stopped in his tracks and gave you a questioning look. "Why would you ask that?"

You feel a little silly. But you want to speak your mind. He always encouraged you to and you have just begun to really say how you feel. "Why me? I... I'm nothing like the girls you usually talk to. I-I'm quiet, shy, I can barely look at you for a long time. I'm not that pretty and you really are out of my league..."

"Okay." He raises a finger. "First off, never say you aren't pretty, because you are. Second, I like you because you're a great person. Thirdly," Jiraiya shrugs and smiles, "you got a nice smile and cute ass. If anything, baby, you're out of my league."

Of course you turn pink in the face. But his words meant a lot. You look up at him. "You really think I'm pretty?"

He nodded. He grabbed you by the hips and pulled you close. You can't tear your eyes away from his. They seem to be searching for something before he finally cracks a bigger grin. He used his fingers to oh so gently guide your chin and angle your head. He moved in and gave you a kiss. Your first kiss. You grab onto his shirt and hold him there. You savour the feeling of it. It feels good. His lips are soft and just the right amount of plump. They are firm but relaxed. They taste a little like the honey dango you split with him earlier. When it broke and he pulled back, there was a small noise that kisses made you always wanted to make. The little smack and chirp of a broken wet kiss. You didn't even realize you closed your eyes to really take in the feeling of it until you slowly opened them. You are lost in his pretty dark orbs.

"Thank you..." You say quietly.

Jiraiya smiles again. He cocks a brow. He looks very amused. "Did you just thank me for kissing you?"

"I guess I did. I... Is that what you aren't supposed to do?"

"No! It's very sweet. You're welcome!" He leaned back down to peck you with another kiss. "I'll kiss you anytime you want!"

"I-I like kissing you!"

Jiraiya laughed and was happy to entertain you with kisses. Honestly he's ready to entertain you all night with more. This dating thing was going well. He finds you quite attractive. He cracks it to eleven and he took you to his room. He's aiming to see that body of yours and the faces you make as you cum.

You are anxious to be there. You are in a man's bedroom. You are sitting on his bed and making out with him. You hope it's not obvious that you have never done this before. Your hands are shaky with anxiety as they settle on the back of his neck. His hands feel warm and heavy on your body. They rub back and forth on your hips to your back. Every little touch sent tingles up your spine. You jump when his fingers go under your pants. They touch your bare hips and tickle the waistline of your panties.

"Jiraiya..." You quietly trail off. He kisses you again. You pull back. "Jiraiya wait a second."

"Don't worry, baby. I got you." He closed the distance and kept your lips occupied.

He pushed you down and got on top of you. It felt good. But it's overwhelming. You're on his bed pinned under his body. His frisky hands push up your shirt. He bites your bottom lip ever so slightly. It does feel nice, but gosh it's a lot. Jiraiya was gentle in his approach. But it's so intense all the same. His hands are careful to treat you with care, but his lips are refusing to let you catch a breath. You know what he wants and you begin to panic. There's something you still haven't told him and you're a little scared too.

"Please!" You gasp in some air before he goes back in. You gently push him away. "Please wait!"

Jiraiya paused. He was midway kissing you. His hands are right under your bra and his knee is right between your legs. He sighed and pulled back. He crawled back to give you some space. He sat back on his knees along the edge of the bed. You look flustered and overwhelmed. He's left you gasping and teary eyed. This is not the reaction he was hoping for.

"Sorry." He said. He cleared his throat. "I didn't mean to..." He furrowed his brow in confusion. "Did I do something? Are you okay?"

"N-No! You did nothing wrong!" You assure him. You wipe your eyes and steady your breathing. "I... I haven't... I've never... I-I'm... Oh goodness..."

A growing realization hits Jiraiya right in the face. His eyes grow wide and his cheeks slowly gain a pink colour. "You're a virgin." He finished your stammering sentence for you.

You are so embarrassed. You cover your face with your hands and nod. You feel ashamed. "I'm sorry! I didn't want you to think I'm a loser or anything!" You start crying because you feel so bad. "I don't think I can have sex with you! Not right now! I'm not ready!"

Oh. You poor sweet thing. You are reduced to tears from your confession. Jiraiya sighed slowly. He pushed his disheveled hair away from his face as he looked you over. You shouldn't be crying over something like this. He reached out and grabbed your wrists.

"Come on, let me see your face." Jiraiya spoke in an endearing way. He can feel the heat your face is giving off.

You relax your arms and let him pull your hands away. You must look terrible at this point. Face redder than a tomato and eyes puffy from crying. How does this man tolerate you? Even as a big red teary mess, he kisses your hot cheek. You dare to open an eye to look at him. You are afraid he's disappointed and disgusted by you. But his smile is still there. It's warm and understanding.

"There's nothing to be ashamed of." Jiraiya assured you. He cupped your cheeks. They are still so warm. He wipes away your tears. "I understand that it's scary." He put a kiss on your cheek. "It's hard to find someone that you can trust with something like this." He chortles before confessing something. "To be honest, I didn't have sex until I was about twenty four."

"Really?" You ask in a very small voice. It's hard to believe someone like him had trouble finding a partner.

"Yeah. I didn't find someone I trusted enough until then. It was all so new and weird. But it felt really good."

His words are calming you down. He puts light kisses on your flushed face. You reach out and wrap your arms around the back of his neck. You've stopped crying and are just sniffling as you kiss him back. He understood the struggle. The desperate feeling of not hitting that milestone where most adults your age have had an average of two partners by then. It's a specific mix of feeling rejected and ugly. That no one found you attractive enough to try.

"I know you're not ready. I'm willing to wait and go at your pace." He continues to comfort you.

Your breathing is getting calmer as he kisses your neck. Your hand is petting his head and running through his hair. It feels nice. He takes a chance and wraps his arm under your back and pulls you up to press against him. Your arms wrap tighter around him in response. It's nice being held so close. For both him and you.

"I'd love to be your first and show you exactly how this is supposed to make you feel. You mean a lot to me." Jiraiya finished up his little speech on a sweet note.

At this point in your life, it might as well be with someone special. You do feel something special when you are with Jiraiya. He's so sweet to you. He takes the time to listen to you and understands your fears. It seems he came from the same roots as you when it came to finding a partner. You know he would treat you right. But you aren't quite ready for all of that yet. Maybe with some experience doing different things, you could see yourself losing your virginity to this man.

"I want you to touch me... but I don't know what to do." You finally say.

"That's okay. Let's go step by step?" He offered. "Can I take your shirt off?"

"Okay." That you can do.

You put your arms up. You feel Jiraiya hook his fingers along the bottom hem. He pulled it off of you. He smiles and marvels at your newly exposed skin. You watch him carefully for his reaction. But it's fairly unreadable aside from that relaxed smile. It's affectionate and charming.

"You are very pretty. Can I take more off of you?" Jiraiya was being very polite.

It all came from a place of understanding. His first time was a little rushed and rough. He was eager to get it in but scared of the results. He didn't want that experience for you. You deserve to enjoy yourself. He has a rare opportunity to show you one of life's most sensitive and intimate things. He wants to do it his way with you in the loop with every step. Any sexual activity should be positive and consensual. Jiraiya can easily admit to himself that he's not a romantic, but he's a pervert with standards. Any real sexual encounter should be like this. A little slow, unsure, and fearful. It's all new territory and he's determined to make his woman feel nothing but pleasure.

"Uh..." You pause as you think on your options. "I guess my pants."

"You guess? Are you sure?"

"Yes." You nod with assurance. "Please take my pants off."

Jiraiya chuckles to himself. You make him laugh with your wording sometimes. Thanking him for kissing you was still his favourite instance of this. You are polite at the oddest of times and he loves it. He leans down and decides its best to give you some attention. He kisses your bare skin. Your ribs and belly are being decorated with his light pecks. They are slow paced kisses that are meant for you to focus on. You relax yourself as he does this. You shut your eyes for a moment to focus on the feeling. It's pleasant. It tickles your skin ever so slightly. Not in a bad way. The kisses are just so gentle they give off that tickling sensation that light touches do. You feel the button and zipper of your pants begins tugged on. His finders grab the sides of the material. They slid down your hips. Then your thighs. Down your legs, exposing more skin to the cool air of the dark room. Jiraiya runs his hand along the back of your leg as he pulls the material off of you. You are smooth and silky under his touch. He pulls your pants off of your feet.

This was enough to pick up your breathing again. This was exciting and you feel that tingly sensation all over your skin as he looks at you. Jiraiya runs his hands back down your legs. From your knees and to your inner thighs. Your panties are keeping you covered. His hands don't breech that barrier. He is just feeling the soft material of it with his fingers.

"Anything else that should be taken off?" He asked.

"No... No I don't think so." You open your eyes and look at him. "I'm not ready for that."

"Okay. What now?"

You look him up and down. He's still clothed. "Can you take some clothes off?"

Jiraiya exhaled a bemused laugh. "I'd love to!"

You watch as he took off his shirt. He pulled his green kosode open. It fell off his shoulders and down his arms. You are mesmerized by his graceful movements. Oh he's pretty. Lovely fair skin. He really has an intimidating stature. Tall, broad, buff. All his body was well toned muscles that aren't too big, not too small. There's a mix of scars on his torso. From small nicks and specks to long carvings. They aren't bad to look at. It simply told a story of the trials he endured as a ninja.

"You're beautiful." You are struck with wonderment at the sight of him.

"Beautiful?"

"O-Oh! Pretty! Er! Handsome!"

That loud laugh you know and love fills the room. At least Jiraiya finds you funny. You groan at your awkwardness and cover your face with your hands. He giggles at you as he leans over you. He takes your hands away to give you a kiss.

"You're pretty too! Come on~! Stop covering that lovely face of yours!" Jiraiya teases you a little as he coos and chides you in a lighthearted way.

You squeal with laughter as he pinned your hands against your belly. He's kissing you and making flirty deep throated laughs of a pervy madman. His teeth lightly scrape against your cheek and the side of your neck. Once he goes over it with his teeth he attacks it again with kisses. It calms you down.

"What else can I touch? How far can we go?" Jiraiya asked. All of the joke was out of his voice. There's something about it that sends tingles up your back. It's low and quiet. Intimate and sexy.

You hang on his words. You are aroused. You do want more. But you lack any experience. You shift and swallow nervously as you think on what to tell him. It's hard to think clearly in this state of mind. With your partner's tongue, teeth, and lips paying such beloved attention to your neck.

"Can I use my mouth?" He asked. He moved his lips up to give your jaw right under your ear some love. "I can smell how good you'll taste from here."

That caused some anxiety. You don't want this man to be eye level with your crotch. If he doesn't like it you will be mortified. "N-No. I'm really not ready for that."

"Heh heh. Alright. I guess that just leaves my fingers."

"I guess it does."

"It'll feel good, I promise."

You nod. You look him squarely in the eye. "I trust you."

Jiraiya smiled at that. Atta girl! You look confident that you want this and he's fine to continue. He put you down flat on your back. You lay there as he flops down beside you on his side. His hand is propping up his head while the other wiggles their fingers in a promiscuous fashion above your body. You switch between watching his hand and looking at his face. He's smirking at you and wiggling his eyebrows. It gets a laugh out of you. Jiraiya laughs as well. There we go. You are getting comfortable. Sex isn't always passionate and sweaty. It can be silly. He doesn't mind making it a bit silly. You respond well to the funny tension breakers. He finds himself defaulting to that when you're uncomfortable or unhappy. He doesn't mind acting like a goofball to get you to crack a smile and release some of your tension.

You watch as his hand lowers. It lands on your stomach. It's already causing fluttering along your skin. It feels like it's pooling and attracted to your sex. It's a new feeling. It's warm and tingly. Jiraiya is watching your every movement and reaction. Your lips are parted as your breathing is getting heavier. Your cheeks are a nicer colour of pink and not so overwhelmingly red. You are warm to the touch. Your pulse is strong under his hand which is telling him that you are excited. Your thighs are together and shifting back and forth.

"Spread your legs." His tone was sweet and coaxing. His fingers are stroking back and forth over your belly in a slow motion.

"Okay." Your nerves are building again.

You are unsure. You watch Jiraiya as you spread your legs apart. He nods with approval. They are a good distance apart, at least enough to let him work. His fingers run back and forth along the waistline of your panties. The skin there is sensitive. It's odd to think how little of this area you actually touch. It's lightly ticklish but not bad. It's a similar sensation to a feather being dragged on your skin. His fingers finally dive under the fabric of your underwear.

"You nervous?" Jiraiya asked.

"A little." You confirm.

"Don't worry. I won't do anything that'll hurt, alright?"

You nod firmly. Jiraiya has never steered you wrong yet. It looks like he knows what he's doing. He goes the extra mile to make you comfortable. He tucked his free hand under your head. He scooted as close as possible until his body was pressed against yours. He leans partly over you and kisses you. He holds his lips against yours in a passionate kiss. It does distract you a little. He's a good kisser and it felt nice to have his lips on yours. You find your hand stroking up and down his arm just to touch him. His hand slides lower and lower.

"Mhph!" Your noise of surprise was muffled.

A flood of pleasure rolls over you. Finally, Jiraiya was touching you. His fingers are thick and callus. The texture of them was so new. The folds of your sex are wet and moving around his fingers. He's moving them back and forth along the full length of your slit. It's slow and not a lot of pressure. You can't resist jumping when his finger pressed against your clit. Your hips involuntarily twitch. His finger presses against it in small tight circles. He breaks the kiss. You gasp in a breath and yell out a noise. It's not quite loud enough for a moan and too breathless for anything else.

"How does it feel?" He asked.

"Ah! Hn!" You bite your lip. "Good!"

You shift your legs up and down. Your toes curl against the sheets. You must look ridiculous. You can tell your face is squished as you have practically everything tensed. You turn your head away from Jiraiya. You don't want him to focus on your face. You bite your lip and clench your teeth to stay quiet. You've never made these kinds of noises before. They sound so weird. It's turning you pink just from hearing yourself. You breath heavily through your nose as you stifle your noises of pleasure.

Something gets caught in your throat. You grip onto Jiraiya's arm. His finger had pushed inside of you. It was so unfamiliar. His finger hadn't pushed in very deep, but you could feel it and you are very aware of it. How it's stretching you. The ridges and texture of his skin. He pushes in only a little, up to his middle knuckle. It leaves you wanting more.

"Does it hurt at all?" Jiraiya asked in a whisper.

You shake your head. Jiraiya kissed your neck. It's exposed now that you refuse to look him in the eye. He kissed and licked the side of your neck. He breathes along your skin and moans. He bites your earlobe very lightly. He pumps his finger in and out slowly. He exhales a hot breath on your ear. It causes a shiver throughout your body. He's doing what he can to encourage you to express your pleasure.

"Do you like it?" He whispered. His voice was husky and hot in your ear.

You nod. Jiraiya exhales a laugh. Oh his sweet shy girl. It seems he's gonna have to work harder to make you open that mouth of yours. This is a fun challenge. He never expected that you would be so hard to get some vocals. He squeezed the rest of the length of his finger and palm against you. He had enough foresight to use his middle finger. He used his first and ring fingers to squeeze the folds of your pussy around his middle finger. It added some pressure and some different sensations to keep you on your toes. He ground his palm against your clit in a circle.

"Ah!" All These new elements got a rise out of you.

You bite your lip. It feels so good! But you sound so weird. Like yourself but not yourself. You aren't sure what to make of it. Your partner sure seemed to enjoy hearing it. Jiraiya's breath hitches from your reaction. That's exactly what he wants from you. He moved faster. He wants to hear more. You grip his arm. He uses his free hand to angle your head towards him. You stare at him through almost shut eyes. You are panting loudly. You use your free hand to swing over and grab the back of his neck. You push him down. He follows your lead and kisses you. You squeal and moan in his mouth. Your hips rock back and forth with his hand. The kiss keeps breaking for you to take in air which are loud as it feels impossible to gain a deep gasp of air.

"You're close, aren't you?" He asked.

"C-Close to what?" You can barely speak you are so breathless.

His brows almost rise off of his face. "Uh... have you ever done this before?"

"No!"

So you are like... virgin virgin. He feels slightly blessed to have found you. The pervert and the virgin. Oh you are just a treat! He pushed the full length of his finger inside of you. He pushed it in and out quickly. Your hands start to shake. You hold onto the hairs at the back of his neck. Your back arches. Your toes curl. Everything in between was stiff. You inhale sharply and your mouth hangs open.

"Don't be shy~!" Jiraiya encourages you. He kisses your neck, where he can feel your raging pulse. "Scream. Moan. I want to hear it."

"Jiraiya!" You heed his advice and cry out his name. It's still a slightly shy squeak as you fear to be loud. But it's the loudest he's ever heard you and he's into it. It inspired him to curl and twist his finger to edge you on.

The feeling is unusual. Your whole body is wound up tightly. Every muscle is effected in a way you never knew it could be. Then suddenly it sprung. An overwhelming sensation of butterflies and something like a wave hits you. It's tingly and fluttery. It felt amazing! Your legs clamp around his fingers as your body contracts. You can't hold in another shout. A flood of something came out of you. You can feel it soak your underwear and down your thighs.

Jiraiya keeps his hand there until you relax. His finger pushed in as far as possible to help you get off. His breath his held as he watches you. He lets it out when you do. It's like he came vicariously by watching you. He feels a little overwhelmed and flushed just from doing that!

Once your back hits the bed again and your legs go limp, he pulls away his hand. You mewl as his digits slid away. Everything just felt so sensitive. You shift your hips and thighs. You adjust to the feelings of what you just went through. Your whole body was wired. You're a mix of tired but excited. As well as you are in a state of relaxation and contentment. You look over at Jiraiya. Oh! You gasp as his fingers are to his lips. He licked them while looking you up and down.

"What? You're tasty!" He laughed.

You sink down into the pillows. You feel a sense of embarrassment as he tastes your cum. You've never seen that before. Well to be fair you haven't seen a lot. Was this normal? He's enjoying himself at least so perhaps it is. You stretch your stiff legs. You inhale deeply and let it out slowly. That was taxing, but you wouldn't mind going through it again. It left you tired but wanting more. It's a strange mixture that you haven't felt before.

"Was that really the first time you've cum? You've never touched yourself?" Jiraiya asked. There's no judgment in his voice, just curiosity.

You hug your arms around yourself. "No... not really. I always thought it was weird... I never had the desire to."

The more perverted nature within Jiraiya felt absolutely elated to have such a sexually naive partner. Oh the things he's going to show you~! Your mind is going to be blown. He smiles and pulls his fingers away from his mouth. You need to be touched. He wants to. He loves touching you. He stroked your arm and belly with the very tips of his fingers as he asked his next question.

"What about now?"

You swallow the lump in your throat. You feel that familiar heat of embarrassment. This subject still made you flush. You nod. You would do this now that you know how it makes you feel. He smiles and kisses you.

"Good! I'm happy to help you with that anytime!" He encouraged you wholeheartedly. He pecked you with several quick kisses while his hand drifted up and down your hip. "Making you feel good is one of my favourite things to do!"

You smile at Jiraiya. He's got that big grin on his face that was a little perverse, so you know he meant it. You reach out and hug him tightly. He's glad to hold you against him. You cuddle up to him with your head on his chest. You really like this man. No one has ever been so considerate of your body and feelings before. This realization makes you want to ask him something. You sigh out some of that building nervousness.

"Jiraiya?" You inquire in a quiet voice.

"Hm?"

"Uh... will.. you uh... can you be my... um." You swallow down your anxiety. It's just so nerve racking! You nuzzle into him and stroke your hands up and down his back. It's easier without looking in his eyes. "B-Boyfriend? Will you be my boyfriend?"

Jiraiya began to laugh. It shook you as his body moved with it. You began to wonder if you asked a dumb question. The idea was quickly cut off as he squished you in a tight hug. "Of course, baby! I'd say we're already there!"

You can feel the smile grow on your face. Your boyfriend puts kisses on the top of your head. He giggles as he affectionately nuzzles his cheek against the top of your head. He's just giddy and excited from the door he's opened for you. Jiraiya's brain works fast as he thinks about what other things he can show you in the bedroom. He wants to be as affectionate and encouraging as possible. Even if it's low and slow, every step of the way will be fun and comfortable for you.

It's so secure to be in his embrace. It feels nice to have someone to curl up with. Especially since that someone understands your plights and hesitations. You find yourself tired as you settle down. The idea of being in bed with your significant other sounded good. You finally have one after all! You plan on enjoying every little thing that partners do with one another. Even just cuddling with Jiraiya is making your heart pitter patter with excitement. His arms are big and heavy around you. He's toasty warm. His bare skin against yours was soft. He smells really good. You can hear his heartbeat with your head on his chest. His legs are shifting slowly to hook yours in a tangle. His hands travel down your sides before resting on your butt.

"Too much?" He asks.

"No. Just right." You reply.

He hums a single note of acknowledgment. If you're good, he's good. He puts another kiss on the top of your head. Your eyes began to drift closed. The beat of Jiraiya's heart was steady and rhythmic against your ear. He was content to lay how he was with you. The winding down and relaxing for once and a while while also holding a pretty woman was kinda therapeutic. Cuddling was one of those rare things he does, but it always makes him feel happy. He usually watches women and rarely touches. This was a nice change. Dating was a nice change. You are a nice change for many aspects of his life. Perhaps he is a little lonely and tired of bachelor life.

Just try not to fuck it up, the rude side of his conscience reminds him. You're so sweet, shy, and lacking a little bit of confidence. Not that these are bad qualities or anything! Jiraiya is just having a tad bit of trouble on getting you to open up. You are so quiet sometimes it's hard to read. He really doesn't want to misstep and ruin this. He's never gone for the quiet ones before. Little did he know that the best girls are the ones who tend to fade in the background. The ones who don't like to have lots of attention on them or be in big crowds. Then he met you and he realized he's missing out on probably the kindest bunch of people out there.

"I'll try hard to make this work." Jiraiya promises himself and you that.

"Hm?" You hum sleepily. You began to drift off as you had gotten so comfortable in his arms. "Did you say something?"

"It's nothing." He assures you. "Just thinking."

You hum again. You fade back away into sleepiness. Jiraiya yawns. You're making him sleepy. From the sound of your sleepy voice to the way you keep him nice and warm with your body heat. Well... he's got nothing better to do. A cat nap with his girlfriend sounded good. He shut his eyes and falls asleep along with you.