Half and Half

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Both of these manga are centered around the idea of a girl falling in love with her childhood best friend; the childhood friend in question ends up coming out as a woman. Friendship, love, and identity are key parts in both manga, and the romance and relationships are pretty well handled, making two heartwarming stories about what it means to love someone. 

If you're looking for another story with trans women, you may be interested in this one too. 

Oh well, they do have different scenarios, but the story is basically the same. The main characters are: a unusual protagonist in shoujo, a girl who is not cute or feminine and a boy cross-dresser. In Kuragehime, they're strangers in the beginning, while in Half and Half they are childhood friends that meet after 13 years. Both deal with gender bender, Kuragehime in a funny and sometimes serious way and H&H in a more deep way: deals with homossexuality and prejudice... Both are great manga, I only read Kuragehime's first two volumes, but I watched the anime and when I started Half and Half manga I was like: "Oh, reminds me of Kuragehime. This is good and could totally happen in the anime's continuation". So, if you like K's anime and manga, you could give a try to Half and Half, it deserves a 8, imo. read more 

Main boy crossdresses as a girl and is attracted to a boy/boys. Main girl looks masculine. In HaH they are childhood friends and the girl loves the boy, while in KnN, they are rivals for the love of one guy, but the boy ends up falling in love with the girl.