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alt title(s): Tentacle Rape
"Damn. Doin' it with a squid."

Knowing that tentacles have a preference for True Loves, I will keep an eye out for any and all creatures that might have them.
— The True Love List: things I will do if I am ever a love interest.

... and from that day forward, Erstin Ho never looked at swim class the same away again.

Some demons have nothing on their minds but sex. They want it, they want it in quantity, and they want it from nubile young women (especially Japanese schoolgirls). To this end they almost always manifest in forms that have many, many tentacles, tentacles that are used to catch, hold, undress and violate said young women, usually in every way possible simultaneously. Naughty Tentacles are a staple of Hentai anime.

Naughty Tentacles evolved after prohibition against the explicit depiction of genitalia and pubic hair was written into the Japanese body of law following WWII. Since animators couldn't legally depict male genitalia, they created a surrogate. The Urotsukidoji (Legend of the Overfiend) OAV series introduced monsters with one or more phallic tentacles. Although these tentacles were "weaponized" for a very pragmatic purpose (inasmuch as porn can be considered pragmatic), they quickly became a powerful visual icon that's now internationally associated with erotic anime... and sometimes, anime in general.

According to one essay on the subject, "Countless monstrous tentacles assaulting a woman is a powerful visual image for both male and female observers. The idea of a single male completely overwhelming a woman and driving her to an impossible height of stimulation can be an empowering image for male viewers, and a fulfilling fantasy for females." Broadcast anime typically only makes sly allusions to it, although some series have become much bolder in "tame" depictions.

This is Older Than Radio; the woodcut Dream of the Fisherman's Wife by ukiyo-e artist Hokusai, dating back to 1820, features a lady in intercourse with octopi. The popularity of this trope has spawned numerous jokes regarding the danger of tentacles that schoolgirls, particularly Japanese schoolgirls, apparently face.

Interestingly, being subdued or tied up by said feelies is still done straight as one of the nonviolent situations that gets past even the strictest censors for cartoons, and it seems just an unfortunate side-effect some fans can't watch that any more without thinking of the Power Perversion Potential.

Compare Mind Rape and Face Full Of Alien Wing Wong. Contrast with Combat Tentacles (which are used to impale people in the normal sense), and Tentacle Rope (when the tentacles grab without being naughty).

Also, needless to say, due to the nature of this trope, many (if not all) of the examples are NSFW. 10 years ago, perhaps the trope namer, there was a website Naughty Tentacles.com. It was Exactly What It Says On The Tin.

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Naked ApronPorn TropesNo End In Sight
Mr Magoo And The MonsterOlder Than RadioNietzsche Wannabe
Naughty NunsTurn On TropesNerds Are Sexy
Mind RapeRape TropesNear Rape Experience
Naughty By NightSex TropesNeed A Hand Or A Handjob