To reduce the complicated mess of gender dysphoria into something so inelegant as "man wearing women's clothing = trans" is to discredit a lot of the groundwork that has been laid out for growing acceptance of transgender individuals. The bit with Cloud crossdressing is not transphobic, because crossdressing in and of itself has no bearing at all on trans-ness. To borrow a phrase; it's not about your hardware, but the software in your heart. Cloud is male. Cloud is a man. Cloud finds himself in a weird situation where he does something outside of his comfort zone (dressing up as the opposite gender) in order to complete a task. Hilarity ensues because in comedy, often the best laughs stem from breaking social taboos and, still to this day, crossdressing is a pretty big one. It's cute. It's cheeky. It's humorous. The one thing that it is not is a commentary on trans individuals. In fact I'd venture to say it has nothing to do with transgender individuals. Crossdressing is its own thing."
I feel I should mention my intentions for how the story would treat the subject in later chapters. Yes, spoilers below!
Anyone who has read the first chapter knows Iceburg ends up in a dress each time he uses the magic of the cards. He's embarrassed but he uses it to his advantage as a disguise to avoid capture by his enemies. He's defensive about it at first. I planned to make it so over time he grows used to it, stops feeling embarrassed and accepts it like a uniform for the job. Near the end of the story he looks back on his embarrassment and admits to himself that the reason he had been so defensive was because he was afraid that wearing a dress would lead to accusations/assumptions that he's gay. And the reason he was so worried about that was because he was a closeted bisexual with secret feelings for his male best friend. In the end, the experience helps him face a part of his identity.
What do you think? Should I continue this story?