The first instance of tentacle eroticism (aka squid porn) is largely attributed to legendary Japanese artist Katsushika Hokusai who created an erotic woodcut of the ukiyoue (‘pictures of the floating world’) genre around 1820 called The Dream of the Fisherman’s Wife (aka ‘Pearl Diver and Two Octopuses’) depicting a woman entwined sexually with a pair of octopuses.

The Dream of the Fisherman's Wife
A movie was made about Katsushika Hokusai called Hokusai Manga (aka Edo Porn). Below is a scene from the movie.

Hokusai Manga
Artists over the years and across cultures have seemingly been inspired by this piece of artwork and have attempted their own interpretations. Australian artist David Laity created a storm when he exhibited his interpretation.

The Dream of the Fisherman's Wife by David Laity
Norwegian sculpture Rune Olsen examined censorship in society and within ourselves with For Everything I Long to Do, based on Hokusai’s Dream of the Fisherman’s Wife.

Rune Olsen's representation of The Dream of the Fisherman's Wife
In 2001, Masami Teraoka painted Sarah and Octopus/Seventh Heaven.

Masami Teraoka's Sarah and Octopus/Seventh Heaven
Katsushika Hokusai is often considered the grandfather of Japan’s hugely popular hentai genre of anime and manga, tentacle rape or shokushu goukan (触手強姦), where women are attacked and penetrated by tentacled creatures.

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With all those tenticles, how come only one nipple is being attended to?
dude, that is a very interesting point and good observation!
That Bond movie wasnt nearly as good as what it could have been!
“Octopussy”. Good angle!
I remember seeing a cartoon in Australia (and i´m sure there are many around the world depicting a man fishing in waist-high water) and a fish was giving him fellatio and it was titled ¨The Happy Fisherman¨.
I guess they got the idea from that octopus/giant squid!
is this what your talking about?
I bet that brings more pain than pleasure
hahahah
yes thats it. Not sure if its the exact same as it was years ago. But close enough.
Who wants to go fishing this weekend???
Those frisky molluscs!
http://static.howstuffworks.com/gif/octopus-2.jpg
There’s a mouth that would encourage a girl to look before she leaps.
Ouch!