Jam It In! / You Lost Me
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About
Jam It In!, vagOOO, and pOnOs are exploitable phrases stemming from an awkwardly translated hentai doujin[1], in which the Fate/stay night character Saber, asks her master Shirou to restore her magic by "putting his ponos to her vagooo, and then J-J-JAMMING IT IN."
On the other hand, the phrase/image You Lost Me became a response to any sexual innuendo, mocking Shirou's confusion about what Saber was asking him to do.
These phrases made their first appearance on 4chan's /a/ board before later spreading to the infamous /b/ board. (See also: how is babby formed)
Origin
The catchphrases originate from page 18 of Hiroyuki's hentai doujin, Platonic Magician H [1] based off the popular visual novel Fate/stay night. It is the same series famous for People Die If They Are Killed, MOU IKKAI, Gar, and Unlimited Blade Works.
In it, Shirou Emiya is asked to replenish his servant's (Saber's) magic, but Shirou is apparently clueless about sex, and needs Saber and Rin Tōsaka to help him out.
You Lost Me comes from the first panel of one of veloxiraptor's comics[2] about Fate/stay night.
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External References
[1] Fakku – Fate/stay night – Platonic Magician H (NSFW: Explicit Content) (page unavailable)