Ouran High School Host Club is a hilarious, tongue-in-cheek manga and anime about Haruhi Fujioka, a scholarship student at an exclusive (expensive) private school who runs into some trouble with the school host club (more or less, they guys are escorts, without actual sex, playing doting, perfect boyfriends to rich, teenaged girls.) The club forces Haruhi to join to repay a debt, only discovering after the fact that Haruhi is female.
This anime pokes fun at gender and genre stereotypes (going so far as to have a character actually call the characters and situations by their tropes–this is a flirty, reverse harem shojo, by the way) while also being charming on its own. There is spicy sexual talk and romance, but no real sexual content. Better for older kids (or at least those you don’t mind explaining “twincest” to) but definitely an enjoyable gem in the genre.
Side Note: Like a lot of anime there is a strange combination of acceptance and hurtful stereotypes. The biggest example of this is Haruhi’s father, who is trans. The characters, even the father himself, commonly misgenders himself (thus why I’ve done so here, because the character does use he/him pronouns, but presents as female) and refers to him as a “tranny”. However, he is intelligent, caring, protective, hard working and over all extremely supportive and the other characters also accept him and his presentation with respect and no judgement, and instead with sympathy for how others treat him. He is actually an excellent, if complicated, parental figure to all of the host club, and when there is ridiculing o him it is not about his gender presentation, or even behaviors linked to gender roles, and instead it is about him getting emotional or making mistakes. This is one of the most accepting portrayals of a trans woman I’ve seen, as the character isn’t cliche or a cardboard cutout, but instead is a fully realized character who also happens to be trans.
Contains: sexual teasing/talk including frank use of tropes like twinces/incest, sugar daddy/baby, and forbidden love, prominent transgenger character, heavily implied same sex relationships