>>279767596 (OP)shit bait, YWNBAT
It's pretty rare that serious takes on the subject get an adaptation because the reality of the condition isn't exactly fun, and it isn't relatable to the vast majority of potential audiences either. Hourou Musuko for example is probably the most accurate portrayal of tranny stuff to have gotten an anime, but if you can't relate to it I wouldn't expect you to find it enjoyable to watch.
If you want something fun without being explicit about realistic tranny stuff then try Hibari-Kun.
Moyashimon and Genshiken Nidaime both have a character that's more ambiguous about their identity, but each of them capture the "vibe" of figuring yourself out in college extremely well. (actually anyone who discovered themselves in cozy early 2000's college would probably enjoy those shows, they have several other great characters)
If you just want a funny side character that's explicitly trans but played more for fun than realism maybe give Ixion Saga DT a shot.