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I am looking for an anime, where a guy with long blonde hair dresses as a girl to frequent an all girls school.

It was his father's last wish, his father or grand father not sure, in order to get his inheritance.

His childhood friend also frequented the same place and helps him cross-dress.

There was some sort of sister system in place and aside from that a big sister thing.

I don't remember the date of this anime but the animation looked like something of 2000ish.

Hopefully some one can help me out.

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up vote 7 down vote accepted

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Well, then it must be Otome wa Boku ni Koishiteru. The boy who cross-dresses to get into the all-girl's school is named Mizuho Miyanokouji.

From Wikipedia:

Otome wa Boku ni Koishiteru revolves around the main protagonist Mizuho Miyanokouji, a male high school student. After Mizuho's grandfather dies, his will is reviewed, which explains his desire to have his grandson transfer to Seio Girls' Academy, the same one his own mother attended and his ancestors founded. Abiding by the will, Mizuho cross-dresses to attend the school. The headmistress, the deputy head teacher (visual novel only), Mizuho's homeroom teacher Hisako Kajiura and Mariya Mikado initially know his secret; Sion Jujo and Ichiko Takashima also eventually find this out.

Mizuho's friend Mariya Mikado helps him cross dress:

Mariya is Mizuho's cousin-german who grew up with him and therefore knows him very well. When it was decided that Mizuho would transfer to the all-girls school she also attends, she took it upon herself to transform him into a beautiful girl by the use of makeup, and she seemed to have a lot of fun dressing him up.

More information:

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That's the one thanks!! :) – Ruri Jul 22 '14 at 0:34

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The show you're looking for is probably Maria Holic.

The character in question is named Maria Shido:

Mariya is a cross-dressing boy who attends Ame no Kisaki as a girl as a means to win the chairmanship of both the all-male and all-female schools where his late grandmother served as the ex-chairman for both. He deeply respects and loves his grandmother and does not care about actually winning chairmanship. He simply wishes to honor his grandmother's request

Matsurika is Maria's maid, attends the same school and helps him cross-dress.

More info:

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That was my first guess but the grandmother part which was what got me to rethink and it was about Mariya's respect for his grandmother, i don't think inheritance was involved – Memor-X Jul 22 '14 at 0:10
    
Hi, no its not that one, I've update the question with something else I recalled. – Ruri Jul 22 '14 at 0:16

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