YOU SAID:

my brother went to his friends house and then to the park to play

INTO JAPANESE

私の兄は彼の友達の家にし、公園に遊びに

BACK INTO ENGLISH

My brother and his friend's House to play in the Park

INTO JAPANESE

私の兄と彼の友人の家に公園で遊び

BACK INTO ENGLISH

House of my brother and his friends to play in the Park

INTO JAPANESE

私の弟と公園でプレーする彼の友人の家

BACK INTO ENGLISH

Playing in the park with my brother and his friend's House

INTO JAPANESE

私の兄と彼の友人の家と公園で遊んでください。

BACK INTO ENGLISH

Playing in the park with my brother and his friend's House.

INTO JAPANESE

私の兄と彼の友人の家と公園で遊んでください。

BACK INTO ENGLISH

Playing in the park with my brother and his friend's House.