 If you liked
Maoujou de Oyasumi
|
 ...then you might like
Himesama "Goumon" no Jikan desu
|
Both have the same vibes, with a princess that has been captured by demons. Though, upon closer inspection they aren't quite like your stereotypical princess, likewise the demons are not demon-like at all. Both are comedic and totally unserious in nature so you can just relax and watch.
Both shows deal with the premise of a princess being captured in the castle of the Demon King, with the story taking a comical turn as the princess gets comfortable in the castle in pursue of sleeping (in Maoujou de Oyasumi) or eating (Himesama "Goumon" no Jikan desu).
Princesses held captive in these fantasy comedies as we meet new monsters interacting with them. Both MC's are very different in nature as well.
Main difference too is with their premises in that Maoujou's Princess is seeking better sleeping standards in her cell whilst Goumon's Princess is making every effort to not fall into the tempation of good food.
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Recommended by BonBonToro
Both very similar settings with princesses being taken captive by the demon lord. One being tortured by food and the other trying everything they can to have a good sleep in her cell.
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Recommended by DarknessReality
Pretty much the same anime.
Except the princess is a victim this time.
If you are looking for a spiritual successor to "Sleepy Princess in the Demon Castle" you can look no further than "'Tis Time for "Torture", Princess".
In both series, you can watch a noble and cute princess deal with being imprisoned by her arch-nemesis the Demon Lord. But there's a catch, their treatment is much more innocent and endearing than you would expect.
Captive princess parody comedy. The "bad guys" are totally inept at being evil and actually come across as caring and friendly. Also lots of cuteness overload.
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Recommended by GrumbleDango
Follows the stories of two captured princesses that soon become adjusted with their new setting. Instead of being miserable like they're supposed to be, they are comfortable and get along with their supposed enemies. Even the capturers form a fondness of their prisoner—it is through this that results in a light-hearted and enjoyable anime.
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Recommended by NekOniiChan
The story is about a princess who is kept captive by demon forces but they are good to them. One of them can sleep plenty of time, Syalis from Maojou... , and the other one feels more liberated from her obligations to the kingdom and the crown. With tons of moe.
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Recommended by Hombre7Electrico