Mokuyobi Post - Urutsukidoji: The Legend of the Overfiend

Urotsukidoji is undoubtedly the godfather of naughty tentacle hentai and was released as a feature length OVA in 1987.  The OVA is based on the manga of the same name which is not as extreme as the anime.

    The story deals with Tatsuo Nagumo, a perverted high school student who is obssesed with classmate Akemi Ito.  After a series of demonic rapes a man named Amano tells Nagumo that he comes from a parallel plane of man beasts and is searching for the legendary Chojin who will reunite the human world, the beast world and the demon world to bring about an age of peace.  Amano is positive that Nagumo is the Chojin and will help him to realize his destiny, while protecting him from the hoards of demons that are trying to kill him.

    This is pretty much the start of tentacle rape in anime.  It is also one of the well known hentai titles in the world...for notorious reasons.  There is an excellent book that came out in the late 90s called The Erotic Anime Movie Guide that has a detailed history of the evolution of hentai and how the naughty tentacle genre cam into existence.  I highly recommend reading this book for an amazing insight into not just hentai but interesting cultural indiscretions that still exist to some extent in Japan today.  I honestly do not recommend Urotsukidoji though.  Historically it has an important place in the history and development of anime, but it is really nothing more than an exercise in exhibitionism and sadism.  The animation is typical subpar 80s style and the English dub is absolutely horrendous.  Yet when it comes to the trials of fandom to teenage otaku this was the Holy Grail at one time, may even still remain one in this day and age.

   The original OVA was followed by 5 more installments that continue the story of the manga.  The have been a few variants of the movie released in North America in various edits.  Apparently a somewhat censored version is currently available on Blu-Ray licensed by Kitty Media, which if you are unfamilliar with, is the foremost distributor of hentai in North America and a subdivision of Media Blasters.

    Bonus fact: scenes from this and the second OVA have found their way into songs by both White Zombie and Atari Teenage Riot...I'm sure a few others as well.