If you're looking for anime similar to Princess Princess, you might like these titles. All recommendations are made by Anime-Planet users like you!
Megumi was a normal kid. He enjoyed getting into fights and mixing it up, and one day he did so in defense of a wizard who was being attacked by bullies. His reward was a magical book that was supposed to grant his wish. The mischievous demon inside the book decided to play a prank on Megumi, though, and instead of turning him into "a man among men," he became a girl. Fast forward to five years later, and Megumi is now entering high school, a tumultuous time for even normal teenagers, let alone a girl who is trying to figure out how become a guy again...
Princess Princess and Cheeky angel have many elements in common: characters pressured to take a gender role they don't want, femininity used as a tool/weapon, school setting, humor, and group-of-friends dynamic.
They both feuture guys taking a role as females, they both have lots of humor and love.
If you like one you bound to love the other.
Kanako Miyamae hates boys so much that she breaks out into hives after any physical contact with them. So when she is able to transfer to the Ame no Kisaki Girl’s school, Kanako is overjoyed that she can now search for her fated yuri partner. When she arrives, Kanako meets Shidou Mariya, a beautiful young girl who is exactly her type... except that Mariya is really a sarcastic and sadistic young boy who is masquerading as a girl! With no intention of being expelled from school, Mariya threatens Kanako into keeping his secret, and decides to guard her twenty-four hours a day to ensure that she does. Now Kanako must share a room with Mariya who is gleefully making her life a misery while using his ‘feminine’ charms to stop her protesting. Throw into the mix Ryuuken, the most popular girl in school who has vowed to protect her; and Kiri - who claims they are dating to prevent her from being bullied - and it seems as if Kanako’s dream of all-girl school life will be nothing like she imagined!
Princess Princess and Maria Holic follow the exact same premise, having males crossdressing as females in a school setting. The comedy element in both derives almost exclusively from the unlikely situations that arise from having traps as the main characters. Maria Holic is a parody that targets shows like Marimite with gusto while Princess Princess is not as referential and more interested in mocking yaoi conventions. They may be niche titles, to some extent at least, but these titles are very likely to share at least some of their fanbase.
Well if you liked the cross dressing pretty boy(s) in one of these shows I think the other might be up your alley. Though the schools depicted in these shows are not similar they both play a major role in the plot and add serious comedic value. What are you waiting for, put on your best goth-lolita outfit- check the other out!
Tsuzuki Asato is a shinigami: a guardian of death. Acting as an investigator in Juuouchou, the bureau in charge of ensuring that each soul passes through the cycle of life naturally, his job often involves dealing with those who would disrupt this cycle. His life after death is about to change, however, as he is assigned a new partner, Kurosaki Hisoka, for a case in Nagasaki - a case seeming to involve some sort of vampire. But the two shinigami soon find that something deeper lies behind this blood-sucking menace...
Both of these series have that shounen-ai flavour to them, but keep themselves rather clean and settle for innuendo and brief hints of boyish romance. They both have varying degrees of comedy and drama depending on how far the plot is along, though Princess Princess relies on the former more often.
Hibiki is unemployed, unmotivated, and out of luck. But it seems his luck just might change: a nearby school is looking for qualified instructors, but there's a catch.. females only! With rent looming around the corner and the landlord threatening to cook the dog if you don't pay up, what's a guy to do? Become a woman, of course. Watch Hibiki as he blunders his way through embarassing situations, under the close scrutiny of the headmaster's gaze and his female students' admiration.
Both Princess Princess and IMMSE are about, well, boys dressing up like girls. In each anime the boys discover that being a girl isn't as simple as just wearing a dress. This leads to hilarious situations. But between the laughs, there is also some room for serious topics like friendship and love.
On Astraea Hill stand 3 prestigious female-only academies known as St. Miatre, Spica, and LeRim; and though the schools are separate, they share a single campus and dormitory. Nagisa Aoi is a 10th grader who has decided to transfer to St. Miatre's Girls' Academy. Though her transition has been smooth so far, while exploring the campus Aoi inadvertently falls down a hill, sees the beautiful Shimuza, and promptly (not to mention embarrassingly) faints. Nagisa continues to see Shimuza out and about, but soon discovers that she is the "Etoile" -- a well respected girl within all of the schools. With Shizuma taking a liking to the new transfer student Nagisa, secrets of Shizuma's past will unravel over the coming school year.
Both Princess Princess and Strawberry Panic show the daily life of the stars of the school, their tasks to represent and cheer for the students, and the sacrifices they have to make in order to fulfill their duties. Strawberry Panic is more romantic than Princess Princess, while Princess Princess is more centered on the funny aspects of the character's weird situation.