Tentacles are often associated with hentai, although it is less common than populary supposed. Tentacle hentai allows for a character to have sex with several recipients at once, without the need for a body. This allows for much more freedom which in turn can lead to several different positions that are normally not available otherwise.
While not the only genre involving tentacle, tentacles are most often associated with rape due to the fact that tentacles can be used as a "living rope" to bind a character and at the same time have sex with it.
While tentacle hentai has come to mean something else, the origins are from the Japanese Edo period when Katsushika Hokusai made a woodcut called "The Dream of the Fisherman’s Wife" which features a woman sexually engaged with a pair of octopuses. This piece was just meant to be a playful look at sex.
Later on however, due to censorship issues regarding the showing of genitals, tentacles became a common substitute for the penis. Credit is most often given to mangaka Toshio Maeda for being the first to use tentacles in this way.
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