I have seen Wandering Son, both the manga and anime. I enjoyed the manga thoroughly, but towards the end (both anime and manga), it became lacking in depth to me...? Please don't take this as offense, it's just my opinion on the story
Brianna, if you enjoy reading manga, I happened to find Bokura no Hentai, (contrary to the use of Hentai in the title, no, it isn't porn) it is based around three junior high school children who come across each other on a cross-dressing community website and decide to meet up in real life. Marika is transsexual, Yui dresses up as his deceased older sister, and Parou began cross-dressing because the boy he liked wasn't into boys. Marika is very similar to Shuuchi in Wandering Son.
There is also a recent one I had only started to read: Himegoto - Juukyuusai no Seifuku.
"This is a story of a group of college-age people who struggle with gender and sexual identity.
Yuki (nicknamed Yoshiki) is a girl, but she is terrible at 'being feminine.' She mostly dresses like a boy and is often mistaken as one. However, she has to wear a skirt and imagine being dominated by a guy in order to masturbate.
Nagao Mikako seems young and innocent, and she uses that apparent innocence to sell her body as a fake 15-year-old. She knows her youthfulness can't last forever, but she enjoys tricking the men. Her friends have no idea of her sexual habits and believe her to be sweet and sheltered.
Aiba Kaito is a pretty good-looking guy, but he wants to be Nagao Mikako. He often dresses as a girl, picking out clothes that mimic Mikako's style. Though he's into cross-dressing, he is still attracted to women."
There is also IS - Otoko demo Onna demo nai Sei, a manga about intersex individuals, struggling to live as themselves (in-between) in a society that is strictly binary and educating others about their existence. It reminded me of being transgender and desiring to be loved and accepted as who I am. It has made me emotional on several occasions and filled with a sense of reassurance knowing that one day, I shall meet someone who will accept and love me for who I am.
Bokura no Hentai & Himegoto deal with dark topics and occasional sexual tones so if those topics have the potential to trigger you, I would suggest avoiding them. But the characters themselves are incredibly fleshed out and "real", I always seem to enjoy those stories the most.
