Naruto Women Having Sex
After he graduated from Konoha's Ninja Academy, Jiraiya was teamed with Orochimaru and Tsunade under the leadership of Hiruzen Sarutobi. Hiruzen gave them a bell test for the team's first exercise, during which Jiraiya repeatedly fell for Hiruzen's tricks, and for failing to acquire a bell, he was tied to a stump as punishment. Hiruzen encouraged Jiraiya to be more like Orochimaru, but Jiraiya countered that his Transparent Escape Technique was a fair testament to his skills, as he could spy on bathing women without getting caught: Hiruzen offered to accompany him to see if this was true. Jiraiya had a certain interest in Tsunade from their first meeting, and when her breasts developed, she became a frequent target of his peepings. She nearly killed him when she caught him on one occasion, forcing him to be more discreet about his interests.
Naruto Women Having Sex
Jiraiya at some point discovered Mount Myōboku, the residence of the toads; in the anime, he was brought there when he tried to summon a toad without first having a contract with them. Fukasaku trained Jiraiya in their ways, most prominently senjutsu. While he was at Mount Myōboku, the Great Toad Sage made a prediction about Jiraiya: that he would travel the world and during that time meet the Child of the Prophecy, a student who would grow up to either save or destroy the world depending upon how Jiraiya taught them.
Jiraiya was a self-proclaimed super-pervert with no equal. His favourite hobby was spying on women while they bathe, a passion he flaunted openly and in fact took pride in because of how infrequently he was caught. Despite this, Jiraiya disliked it when Naruto Uzumaki referred to him as the "Perverted Hermit" (エロ仙人, Ero-sennin, English TV: Pervy Sage) in front of others. With the "research" from his peeping, he would use it as inspiriation for his novels. Despite his high-success as a novelist, this fact did not stop him from taking Naruto's money when he got the chance and spending it on alcohol and women. In the anime, Naruto ghost-writes an Icha Icha book without anybody noticing, suggesting that either Naruto can write like an adult, or that Jiraiya's writing abilities were no better than a child's. Tsunade suspected it was the latter, as she notes that a report Jiraiya wrote when he was younger was poorly written and accompanied by crude crayon illustrations.
Jiraiya's perversion has backfired on him a number of times. When he first meets Naruto, he has no interest in training him. Naruto convinces him to change his mind by using the Sexy Technique, which Jiraiya so strongly approves of that he asks Naruto to continue to use it for the duration of their training. Itachi Uchiha and Kisame of Akatsuki later hypnotise an attractive woman to lure Jiraiya away from Naruto so that they can try to capture him; though it works at first, Jiraiya quickly realises that women aren't usually attracted to him, allowing him to return to Naruto in time to rescue him. When he was younger, he spied on Tsunade while she was bathing and, when she caught him, she broke both of his arms, six of his ribs, and ruptured a number of organs as punishment. Ever since, he's used greater discretion in expressing his interests in Tsunade, careful to make his advances come off only as playful. Jiraiya considers his inability to win Tsunade's heart to be one of the greatest failures of his life. Despite his boisterous nature, Jiraiya was plagued by doubts and insecurities that his life was nothing more than a series of failures. Being unable to save Orochimaru weighed heavily on him, as did the deaths of his sensei the Third Hokage, and his student the Fourth Hokage. Jiraiya considered his achievements paltry things next to the previous four Hokage and desired a death as glorious as their own. In his final moments, Jiraiya expressed his pride in realising a heroic death that was "just barely glorious, but glorious indeed".
Jiraiya was taught how to use senjutsu by Fukasaku, which he can use to increase his speed, durability, and physical strength. He can also use it to empower his other ninjutsu, such as the Ultra-Big Ball Rasengan. Before he can gain these benefits, Jiraiya must enter Sage Mode, which he does not have complete mastery of. This causes his Sage Mode form to make him more toad-like in appearance, such as warts and webbed hands and feet, although his frog-like legs enable him to jump better. Using Sage Mode requires his supply of natural energy be constantly replenished, something that is difficult to do while in combat. For this reason, Jiraiya summons Fukasaku and Shima and fuses them to his body, having them gather natural energy for him. As an added bonus, Fukasaku and Shima can combine attacks with Jiraiya's, as with the Sage Art: Goemon, or they can perform jutsu that he can't, as with genjutsu.
Despite his goofy and eccentric nature, Jiraiya was actually very shrewd in the field. His specialty is intelligence gathering, having a spy network that runs throughout the Five Great Shinobi Countries that he can use to gain information about a particular person or group to be used to his or his allies' advantage. In combat, he is very perceptive; Jiraiya observes all of the opponents' various actions, forms a theory about the how and why, and uses that theory to try and capitalise in the battle. He has repeatedly proven to be a very talented teacher, as all his students went on to become very powerful and well-known shinobi. His memory is very good; as he was dying, he was able to craft a coded message using the page numbers of Icha Icha Tactics, with the first word on each page serving as his message.
During an unannounced return to Konoha, Jiraiya visits the Konoha Hot Springs in order to spy on the women bathing there. He is discovered by Ebisu who, not realising who Jiraiya is at first, tries to stop him and reprimand him. Jiraiya uses a toad to knock Ebisu out so that he won't interfere in his "research". Jiraiya is immediately confronted by Naruto Uzumaki, who Ebisu was training to improve his chakra control and who now, because Ebisu is unconscious, needs somebody else to teach him. Jiraiya refuses to be that somebody until Naruto demonstrates his Sexy Technique, at which point Jiraiya eagerly agrees.
After leaving Konoha, Jiraiya and Naruto stop in Shukuba Town. While they check into a room to rest in, an attractive woman starts flirting with Jiraiya; Jiraiya sends Naruto to their room while he and the woman spend time together. It quickly occurs to him, however, that women are not usually drawn to him, at which point he realises that the woman is under the influence of a genjutsu so that she could be used to lure Jiraiya away from Naruto. He returns to Naruto and finds him about to be captured by Akatsuki's Itachi Uchiha and Kisame Hoshigaki; Sasuke is also there, wishing to fight Itachi. Itachi and Kisame decide to flee rather than fight Jiraiya, which he tries to stop with his Toad Mouth Bind, but this fails. Jiraiya collects a sample of the Amaterasu flames that Itachi used to escape and returns to Naruto and Sasuke, at which point he is attacked by Might Guy.
Jiraiya and Naruto eventually learn that Tsunade is in Tanzaku Quarters. When they arrive at where she's supposed to be, however, she isn't there. What's more, there's evidence that Orochimaru has been there. They find a place to eat to decide what to do next, only to find Tsunade there with her attendant, Shizune. Tsunade is surprised to see Jiraiya, having just met Orochimaru, though she refuses to say anything about the nature of their meeting. Jiraiya informs her that Konoha would like her to become the Fifth Hokage; Tsunade is surprised - having thought Orochimaru was lying when he said he killed the Third Hokage - as is Naruto, who didn't realise Tsunade was being offered the Hokage position. Tsunade refuses to offer, ridiculing those who've been held the title, including the Third and Fourth Hokage, and dismissing the job as fitting only for fools. Naruto, who has his own dreams of being Hokage, is enraged and tries to attack Tsunade. Jiraiya holds him back, but Tsunade agrees to fight with him.
Tsunade is able to protect Naruto and overcomes her phobia so that she can return to the fight. She summons Katsuyu to fight Orochimaru's Manda, with Jiraiya joining in by summoning Gamabunta. After they save Katsuyu from Manda, Jiraiya and Gambunta attack Manda with Fire Release: Toad Oil Flame Bullet. Manda avoids it and attacks them from behind, but they are saved by Tsunade, who defeats both him and Orochimaru. Orochimaru escapes with Kabuto; before he leaves, he warns that he has other ways of fixing his arms. Tsunade heals Jiraiya's broken bones, restores his chakra, and, having accepted the Hokage position, returns with him and Naruto to Konoha.
While the Eight Man Squad is still on their mission, Jiraiya visits Tsunade with news that he's discovered the location of Akatsuki's leader, though he refuses to go into more detail until she meets him for drinks. While having saké, Jiraiya shares news of Amegakure's ongoing civil war, which the Akatsuki leader is rumoured to be behind. Because Amegakure is in a delicate political situation, Jiraiya must infiltrate the village by himself to confirm before Konoha can take direct action. Tsunade feels guilty for always relying on him to do dangerous work like this and offers to help him if he needs it. He reminds her that she, the Hokage, can't just leave the village, but she replies that Naruto will inevitably replace her anyway. While they discuss Naruto, Jiraiya reflects that, because he thought of Minato as a son, being with Naruto feels like being with his grandson. Jiraiya departs, but warns Tsunade about Danzō Shimura before he goes.
Jiraiya is able to successfully infiltrate Amegakure and quickly captures two Ame-nin, Ryūsui and Yūdachi. He tries using tickle torture to get them to reveal information about Pain, but it's only after using the Turning into a Frog Technique on Yūdachi that Ryūsui is forthcoming: Pain is the mysterious leader and god-figure of Ame, who brought the rebelling faction to victory in the civil war by personally killing Ame's former leader, Hanzō. Jiraiya is unsettled by news that Pain killed Hanzō, having assumed from his own past encounter with Hanzō that he was unbeatable. He takes a precaution by removing Gerotora from his body and instructing him to go to Naruto if anything happens to him. Gerotora warns him against this, feeling Naruto is unprepared for full access to the Nine-Tails' power. Jiraiya shares his suspicions that Madara Uchiha is somehow moving behind the scenes which, if true, would mean Naruto will need to master the Nine-Tails sooner rather than later.