8 Answers
I get a kick out of characters who blur gender lines, and if you want a protagonist who’s a femboy crossdresser, a few titles really stand out for me. One that I gush about to friends is 'Himegoto' — the main guy, Hime Arikawa, is literally forced into dressing like a girl by a school council that blackmails him. The series is slapstick and absurd, but Hime’s delicate, overtly feminine presentation and the way the show mines comedy from his predicament makes him an unforgettable example of the trope.
Another show I always recommend when this topic comes up is 'Otome wa Boku ni Koishiteru' (commonly called 'Otoboku'). The lead, Mizuho, is a boy who enrolls at an all-girls academy disguised as a girl; the show leans into romantic comedy and school-life beats, and Mizuho’s gentle, soft-spoken nature plus the drama of keeping his identity secret creates lots of memorable moments. It’s sweet, sometimes painfully awkward, and it presents crossdressing as both necessity and character-defining.
For a different flavor, check out 'Princess Princess' — it features three boys chosen to dress up as the school’s “princesses” to lift morale. The series treats the premise with warmth and camaraderie rather than just gags, so you feel for the protagonists as they navigate embarrassment, friendship, and the weird politics of their school. I love how each show offers a unique tone: absurdist, romantic, or slice-of-life, and they all make femboy crossdressers compelling in their own ways.
I like picking apart how each anime frames a femboy or crossdressing protagonist because they’re rarely identical in purpose. For instance, 'Himegoto' and 'Princess Princess' both use crossdressing as a set piece: bright, comedic, and sometimes fanservice-y, but they also highlight the social pressures the boys face while presenting as girls. 'Stop!! Hibari-kun!' is older and rambunctious; Hibari is written with flamboyance and confidence, and the show leans into camp but still makes the character memorable.
On the other end, 'Wandering Son' treats dress and presentation as part of identity formation — slower, tender, and often melancholy. 'Kämpfer' injects supernatural transformation and action, so the gender-shift reads like both a plot device and a disguise. I find these variations fascinating because they let an anime explore themes from comedy to empathy, and I often come away thinking about how costume and identity are so tightly linked in storytelling.
I get a real kick out of shows that blur gender lines, and there are a few that stand out if you’re hunting for a femboy or crossdressing male lead.
First, check out 'Himegoto' — it’s shameless comedy where the protagonist, Hime Arikawa, is forced into dressing like a girl at school. It’s loud and silly but absolutely centered on a boy who becomes cute and feminine for survival and laughs. Then there’s the classic 'Stop!! Hibari-kun!' where Hibari is a flamboyant, feminine-presenting boy; the tone is older and campier, but Hibari’s character is unforgettable.
If you prefer something with nuance, 'Wandering Son' ('Hourou Musuko') deals with gender identity and includes Shuuichi Nitori, a boy who dresses as a girl and explores what that means. For a lighter, institutional twist, 'Princess Princess' features boys chosen to act as campus 'princesses,' and it leans into both comedy and sincere friendships. Each of these approaches gender differently, and I love how they span from silly to sensitive — they’ve all stuck with me in different ways.
There’s something delightfully odd about femboy leads, and a few series really stick: 'Himegoto' for pure, absurd crossdressing comedy; 'Stop!! Hibari-kun!' for retro, energetic zaniness with a feminine-presenting boy at the center; and 'Princess Princess' where schoolboys take on princess roles as part of a quirky tradition.
If you want emotional realism, 'Wandering Son' is quieter and thoughtful, following a boy who dresses as a girl and learns what that means to him. Each show treats the idea differently — some use it for laughs, others for identity exploration — and that variety is what keeps me rewatching scenes that always make me grin.
Short and sweet: my top picks for femboy crossdresser leads would be 'Himegoto', 'Otome wa Boku ni Koishiteru', and 'Princess Princess', and each scratches a different itch. 'Himegoto' is pure chaotic comedy with a soft, overly cute lead who’s forced into fem styling; it’s ridiculous but memorable. 'Otoboku' leans into romantic-slice-of-life territory where the male lead’s disguise creates tension and tenderness among classmates. 'Princess Princess' treats crossdressing as a club activity — the guys bond over it and the show is surprisingly heartwarming.
If you prefer something thoughtful rather than comedic, 'Wandering Son' handles gender identity and presentation with real care, following a young person exploring a feminine presentation amid the pains of growing up. I still find myself thinking about how each of these shows treats consent, identity, and humor differently — they’re all worth checking out depending on whether you want laughs, feels, or thoughtful reflection.
If I’m being concise but nitpicky, I’d point to 'I My Me! Strawberry Eggs' and 'Wandering Son' as two very different, yet important entries. 'I My Me!' has a male teacher who cross-dresses to keep his job, and the series plays with gender presentation in a workplace/educational setting — it’s part comedy, part commentary on expectations. The protagonist’s femininity is a tool he uses, but the show also uses that setup to explore perceptions of competence and identity.
'Wandering Son' (originally 'Hourou Musuko') approaches things from a softer, much more introspective angle. Shuichi Nitori presents as feminine and is often read by others as a girl; the story is about gender development, confusion, and the tender cruelty of adolescence. While it’s not a light rom-com, it’s one of the more empathetic and realistic portrayals of a young person experimenting with gender expression. If you want something that treats a femboy-like protagonist seriously, this is the one to watch. Both shows, in very different ways, stuck with me because they move beyond cheap laughs into characters you actually care about.
I’ve spent too many late nights tracking down crossdressing characters, and a handful of anime really make the femboy protagonist memorable. 'Himegoto' is obvious: its entire premise is a boy forced into wearing girl clothes at school, and it plays that situation for maximum awkward comedy while still making the main character sympathetic. 'Maria†Holic' flips things interestingly — Mariya Shidou is a male who presents as a girl and keeps the façade, which creates a ton of comedic and romantic complications.
If you want emotional depth rather than just gag-driven scenes, 'Wandering Son' is where the subject is treated with care; Shuuichi isn’t played for jokes so much as inner life and the confusion and hope of growing up. 'Kämpfer' is a different flavor: it’s a gender-transformation show where the male protagonist becomes a girl and must live that role, which often reads like crossdressing in practice even if the mechanism is supernatural. These shows range from goofy to heartfelt, and I love that mix — it keeps the trope fresh instead of one-note.
If you want a quick roundup for bingeing, I’d recommend starting with 'Himegoto' for silly, over-the-top crossdressing humor and 'Maria†Holic' for a witty, theatrical take where Mariya’s true gender is part of the central gag and intrigue. 'Stop!! Hibari-kun!' is a throwback that feels wild by modern standards but still charming, while 'Princess Princess' gives you ensemble chemistry: the boys aren’t just wearing dresses, they’re performing and bonding.
For something more introspective, don’t skip 'Wandering Son' — it treats dressing as part of growing up and is quietly powerful. These shows cover the spectrum from ridiculous to profound, and I always end up smiling at how each one makes the idea of a feminine-presenting boy feel fresh and interesting to me.