Hentai Anime Girl

History
The earliest association between anime and adult animation occurred preceding the release of Fritz the Cat when American distributors attempted to cash in on the publicity garnered from the rating by rushing out dubbed versions of two other adult animations from Japan, both of which featured an X rating in their advertising material: Senya ichiya monogatari and Kureopatora, retitled One Thousand and One Arabian Nights and Cleopatra: Queen of Sex, respectively. However, neither film was actually submitted to the MPAA, and it is not likely that either feature would have received an X rating. One Thousand and One Nights was the first erotic animated feature film, and at 130 minutes, it remains one of the longest animated films.
The Lolita Anime series was the first hentai original video animation (OVA), released in 1984 by Wonder Kids, which mainly focused on underage sex, rape, and bondage. Cream Lemon, which contained many themes found in hentai today, was released later that year by Fairy Dust and contained some in-depth storylines and classic (late 1970s to early 1980s style) artwork. The Brothers Grime was a three-video cartoon-pornography series produced by Excalibur Films in 1986, 1987, and 1988, using titles primarily from the Cream Lemon series, the most popular of Japan's erotic anime before Urotsukidoji.
The Urotsukidoji anime series was created by Toshio Maeda in 1986 and released in America in 1992 by Anime 18. It is most famous for being the first in the tentacle rape genre, though only one scene in the first OVA actually contains any tentacle rape. Tentacle rape was not present in the Urotsukidoji manga, but was featured in a series that he would publish years later called Demon Beast Invasion. Demon Beast Invasion created what might be called the modern paradigm of tentacle porn, in which the elements of sexual assault are emphasized. Maeda explained that he invented the practice to get around strict Japanese censorship regulations, which prohibit the depiction of the penis but apparently do not prohibit showing sexual penetration by a tentacle or similar (often robotic) appendage. Maeda went on to create La Blue Girl, which departs somewhat from its predecessors by lightening the atmosphere with humor, lightly parodying the tentacle rape genre.