Needless+: Saint Lily Gakuen no Himitsu, Otome wa Boku ni Koishiteru: Futari no Elder The Animation Recommendations

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Needless+: Saint Lily Gakuen no Himitsu, Otome wa Boku ni Koishiteru: Futari no Elder The Animation
Needless+: Saint Lily Gakuen no Himitsu
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Needless+: Saint Lily Gakuen no Himitsu
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Otome wa Boku ni Koishiteru: Futari no Elder The Animation
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Otome wa Boku ni Koishiteru: Futari no Elder The Animation
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Both anime are OVAs with few episodes, they feature a boy who is crossdressing in order to enter an all girl school, although their aims are much different. Keep in mind that while Needless focuses on comedy, Otoboku is much more serious and drammatic.
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