Manga: Princess Princess

Tooru: At this famous private boys' school, I, Kouno Tooru, who transferred here in the middle of the term, without realizing it, have had the door to my destiny opened before me. I thought I'd live a dull life in this all-boys' school, but what's this girl doing here?
Mikoto: I'm a guy!

Princess Princess is an anime, live-action drama, and manga series by Mikiyo Tsuda.

Basically: What if you suddenly transferred to an all-boys school, only to see girls attending? That's what happened to Tooru Kouno. But he soon finds out they're not girls. They're actually guys: Mikoto Yutaka and Yuujirou Shihoudani, who are cross-dressing as part of a "Princess" program to let out the straight male student population's sexual frustration. In addition to that, Tooru's been chosen to become the third Princess. At first he doesn't want to, but he finds out there's lots of benefits to becoming a Princess, so he accepts.

Along the way, we meet Akira Sakamoto—a boy who's revered by most of the school but has low self-confidence, Sayaka, Tooru's "sister" (who's really his cousin and also happens to be his stalker, who's madly in love with him), Natashou, the Princesses' costume designer, and Arisada, the Student Council president who organizes events for the Princesses (and who was a Princess himself before).

Originally a manga, Princess Princess had a manga sequel, Princess Princess +. It was made into an anime in 2006, and the live-action show (which focused on Mikoto and introduced a whole new set of Princesses), Princess Princess D, also aired in 2006.

Not to be confused with Puri Puri, a manga featuring an Unwanted Harem. Or Princess Prince, another manga featuring cross-dressing (but this time with an actual royal in the role). OR the webcomic of the same name. Or, for that matter, the character from Adventure Time.

This show provides examples of:

  • Absurdly Powerful Student Council: From the point of view of the Princesses, anyway, who live in fear of Student Council President Arisada's next command. Not only that, but the people who used to be a Princess end up having so many utterly devoted fans that they easily glide into positions of power. Eventually they all seem to end up being extremely rich and successful, such that there is only one man on the board of directors that governs the school who was not once a Princess himself—and he had to inherit his position from his father, who was a princess when he attended the school.
  • Beautiful All Along: In the manga, Sakamoto unwillingly gets a Princess makeover for his final speech in the election for school president. He wins by a landslide.
  • Bishie Sparkle: Happens at least Once an Episode! Generally invoked by the characters doing it.
  • Bishōnen: Almost all of the characters.
  • Blonde, Brunette, Redhead: Somewhat, because Tooru has blue hair and Mikoto's Princess look has pink hair. They fit the trope by proxy, at least.
  • Character Overlap: Mikoto, Megumi, and Makoto from The Day of Revolution, and Akira Sakamoto, as well as the whole Sakamoto family, from Family Complex.
  • Defeat Means Friendship: Although Mitaka has pretty much succumbed to Sakamoto's healing aura and hypnotic smile by the time the presidential election rolls around, his defeat turns him from Sakamoto's rival to his devoted Vice President.
  • Dragged into Drag: Mikoto and Yuujirou, who never got to choose whether they wanted to be princesses or not.
  • Dude Looks Like a Lady: Even when they're not in Princess garb, the Princesses still get mistaken for female.
    "Dudes, you must be either blind or gay! We're guys, dammit!"
  • Elegant Gothic Lolita: Natashou's design style is frilly, poofy, and generally a bit gothic. The princesses wind up wearing EGL versions of maid outfits, nurse uniforms, and the invitable Alice Allusion costume.
  • Everything's Better with Princesses: Well, not of blue blood, obviously, but they're often honored as such.
  • Gender Flip: The Prince Prince mini-comic under the dust cover of each volume, which shows a parallel dimension where female versions of the main characters dress up as princes to soothe the lonely hearts at their all-girls' school.
  • Heroic BSOD: Mikoto's despair about being a Princess ramps up to a full-blown BSOD when his big sister and girlfriend find out about it. Fortunately Megumi snaps him out of it with a kiss.
  • Hero of Another Story:
    • Mikoto's oft-mentioned but seldom-seen girlfriend, Megumi, is the protagonist of Tsuda's The Day of Revolution. Lampshaded by Tsuda's Author Avatar, who says Megumi would take over this manga too, given half a chance.
    • Akira is the protagonist of Tsuda's Family Complex.
  • Human Traffic Jam: When the princesses leave the stage after the play, Mikoto suddenly stops, causing Tooru and Yuujirou to run into him from behind. His reason? His big sister Makoto and girlfriend Megumi, from whom he desperately wanted to keep his princess activities secret, were waiting for him.
  • Inadequate Inheritor: The elder Sakamoto brother is a very handsome guy who projects a blinding aura of desirability and untouchability, which led to the legend of "Sakamoto-sama" at the school. Akira Sakamoto is a plain and fairly ordinary guy whom the Student Council President saddled with "Second-generation Sakamoto-sama" as soon as he enrolled and feels he can't live up to it.
  • Incest Is Relative: Sayaka's one-sided crush on Tooru after she learns that he is her cousin, not her brother. It's all but stated that Tooru transferred schools to try and ease the awkward situation between them. Didn't work: she followed him.
  • Insult Backfire: When Mitaka learns that his rival in the presidential elections, the glorious Sakamoto-sama who he's been hearing so much about, is a plain-looking, soft-spoken average Joe with no charisma, he publicly insults Sakamoto and speculates that he's merely riding on his older brother's reputation. While everyone else is outraged, Sakamoto is impressed (and possibly turned on) by his honesty.
    Akira: So for me, whether the person has a bad attitude or not, if they're up front about how they feel, it really puts me at ease. Ever since I came here I've never known what it was like to be attacked like that, so it was actually kind of refreshing." [cue blushing and floral background] It was exciting...
    Yuujiro: That's just wrong...
  • Kimono Fanservice: Arisada told the princesses that his costumer preferred this to the EGL of Natashou.
  • Love Bubbles: Sakamoto-sama the First is surrounded by soft-focus sparkles and cascades of floating feathers. In public, anyway.
  • Manipulative Bastard: Student Council President Arisada, who always gets what he wants, from roping the there protagonists in as Princesses to convincing Akira Sakamoto's run for election as the next president.
  • Medium Awareness: In the manga, characters often comment on backgrounds and the size of panels
  • Mum Looks Like A Sister: When Tooru and Yuujirou first met Sakamoto Akira's mother, they thought she was his sister and they started arguing whether she was his older or younger sister. When he told them she's his mother, he even had to clarify she's not a stepmother. Then, when Akira's father comes along, they quickly assumed that he was Akira's brother, the "rumoured Sakamoto-sama".
  • Nice Guy: Sakamoto is such a Nice Guy that his excess niceness leaks out and forms a healing, soothing aura which refreshes everyone who comes into contact with him.
  • Omake: In the manga, you get Yonkoma in the back and a minicomic beneath the dust cover.
  • One-Gender School: Fujinori Gakuen is an all-boys school, and the lack of girls is the reason why the Princess program is established in the first place.
  • Pimped-Out Dress: Most of the outfits Natashou designs for the princesses fall under this trope.
  • Retcon: The princess system is implied to have existed for at least 2 generations, but they do not exist in the prequel, Family Complex, despite being set only 1 year after the latter.
  • Shout-Out: In one episode, the princesses are forced to sing and dance to a song on-stage in order to encourage the students. The song they choose? The opening to Cutey Honey.
  • Spell My Name with an "S": Tooru/Touru/Tohru/Thoru/Toru—well, you get the point.
  • Stalker with a Crush: Tooru's cousin Sayaka, who attacked a girl he went out with and followed him to school twice to convince him to come back.
  • Transfer Student Uniforms: Mitaka doggedly keeps his old uniform in the manga. This is despite the fact it includes a pair of rather tragic checked pants.
  • Sorry, I'm Gay: Yuujirou kisses Tooru to finally convince Sayaka to leave. Tooru does not react well afterward (not that this fazes Yuujirou—he suggests going even further in case Sayaka decides to return).
  • Yandere: Sayaka and her habit of stabbing Tooru's girlfriends with scissors.
  • When She Smiles: An important part of the job of the princesses is to cheer everyone up with their smiles. It's a very hard thing for Mikoto to do, as he hates the princess job, which make his few smiles so much more adorable and noticeable.
  • Wholesome Crossdresser: The princesses.