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Jiraiya stated that Tsunade's oppai size was 106cm.

From Tsunade article:

Despite being known as flat-chested in her childhood, she now has a rather large bust; 106 centimetres in circumference, according to Jiraiya.

From Jiraiya article:

when caught spying on Tsunade in his younger years, she proceeded to break both of his arms, six of his ribs, and ruptured a number of organs as punishment.

Considering the amount of fear and respect Jiraiya then developed towards her, how did he know the measurement of the adult Tsunade?

Source: https://www.youtube.com/watch?v=ny7Fni193Jk

(I'm really sorry about the quality of the video)

Below is the image from the corresponding scene in the manga (chapter 406, page 9):

Ero Sɘnnin
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5 Answers5

11

Maybe Jiraiya transformed into Tsunade using a transformation technique and found the size using traditional measures by measuring himself(!).

He may have used Sexy Technique.

senshin
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    According to wiki [Jiraya](http://naruto.wikia.com/wiki/Jiraya) never used Sexy technique (see in Jutsu column). – Light Yagami Feb 24 '16 at 14:17
  • Just because he is never show to and never admits to using it does not mean it was used by him. He definitly prefers the real thing though, so he would not want to transform without a good reason (like finding the numbers). the WIki can only use stuff the manga and other major sources provide. for Kakashi, "he is reputed to have copied over a thousand jutsu" Straight from the wiki, Though it only lists about 40 Jutsu, the ones he actually used in the series. – Ryan Feb 25 '16 at 17:56
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    This doesn't make any sense. Just because he transformed into her does not mean he would have aimed exactly her breast size. He would still have had to measure them. – Akira Mahisaseru Apr 01 '16 at 19:25
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Jiraiya was a very powerful ninja, and particularly proficient in stealth missions. He was almost the sole source of all information on Akatsuki, and was able to enter Amegakure and defeat several of Pain's bodies.

Jiraiya feared Tsunade after she beat him particularly badly once, but if the mission was important enough he showed himself to be ready to risk death.

I believe that with careful planning and execution, Jiraiya could have and would have done this.

Qiri
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6

During the time he was training Naruto, Jiraiya was seen fooling around with girls. It could be from the experience with girls that he had gathered for decades, that he was able to measure a girl's breast size based on looking only.

Ero Sɘnnin
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絢瀬絵里
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My best guest is he use his Cloak of Invisibility Technique a.k.a Cloaking Technique. (Synonymous to Naruto's kage bunshin). I just can't remember on what episode of manga the 3rd Hokage mentioned about Jiraiya using it (I think during a flashback of their training).

Mark
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I believe the real reason why Jiraiya knows Tsunade's measurements probably has to do with him being somewhat of a lady's man in his own words. Which can be confirmed as there's an occasion when he's surrounded by women, thus meaning that he is such an experienced lover that he is capable of guessing a woman's measurement by looking at them. Plus he spent a lot of time spying on Tsunade in hot springs!