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Ech
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Unfortunately you're not going to find a lot of dark, grotesque monsters thesedays. I'd like to believe that I've seen a lot and I keep up with the tentacle/monster genre, the monsters and all that visually aren't nearly what they used to be back in the day.
Also the downfall is that back then things weren't nearly as hardcore as they were today (compared to say, Ai, Lilia, Asagi, Inyouchu Shoku, etc). Though, older hentai were often more violent. For what the OP wants, stuff like the La Blue Girl series, Twin Angels/Dolls, [everything] Darkness like Angel of Darkness, Idol of Darkness, Inma Seiden (everyone always forgets this one), etc, all have really detailed and demonic styled tentacles/monsters, but as said above, don't expect the sexual content to compare to some of todays stuff.
Nothing really comes to mind for modern releases. Maybe Sexy Magical Girl Ai, Taimanin Asagi a bit, Himekishi Lilia here and there, but I don't know what it is ... the old stuff just looks far more hideous, detailed, demonic, etc.
This dark and demonic style is still there in CG's, games, at times, but yeah. I think another factor is just how anime is done thesedays and everything typically looks a lot more colorful: ie, 80's/90's cyberpunk anime shows beat the shit out of modern shows in terms of atmosphere/detail/art. But I'll stop there because I have no idea where I'm going with that.
Oh yeah and episode 1 of Imma Youjo has a cool giant robot/monster/tentacle thing. Too bad the rest of the series doesn't.
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