http://tvtropes.org/pmwiki/pmwiki.php/Main/OtokonokoGenre

An author and his manga.

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"Otokonoko", also known as "Otoko no Musume", is a Japanese genre of romantic and/or erotic stories for men, focusing on Attractive Bent-Gender male Crossdressers. The name is a pun.Details The word "otokonoko" normally means "boy" (literally "male child"), but swapping the "ko" meaning "child" for a different "ko" meaning "girl" gives a compound that Japanese sites like to translate as "male maiden". It is sometimes called '"josou" ("women's clothes"), a more generic term for male crossdressers. Western fandom uses the terms "tomgirl" (as the opposite of Tomboy) and, somewhat less often, "trap".note As this term carries some Unfortunate Implications involving Unsettling Gender Reveal and an actual trap generally being a terrible device, the use of this term is controversial, especially amongst people who are transgender, since it plays to the (very, very false) stereotype of trans women trying to trick straight men into having sex with them. Which is used as justification for transphobic violence.

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Otokonoko features both girl-on-crossdresser and guy-on-crossdresser stories (it's one of the few places where you will find m/f stories and m/m stories side-by-side in the same magazine). The target audience is men who crossdress (or are interested), and men who have a fetish for crossdressers, and the art styles and tropes are typically those of male-oriented romance / ecchi / hentai material. There is also a significant Periphery Demographic of female readers. (Although guy-on-guy otokonoko is often mistaken for Boys' Love Genre, and some Shoujo, Josei, boys love works, and otome games do include characters that identify as otokonoko, anything targeted to women is not the otokonoko genre.)

Although cute crossdressers in romantic situations have been an occasional theme in Shōnen and seinen since the '80s, otokonoko did not start as an identified genre until about 2004. Most works created before this are not usually considered part of the genre, although some have been grandfathered in.

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An otokonoko character must be anatomically male (no Hermaphrodites or Gender Benders) but look convincingly like an attractive girl. Most identify as male, but even when the character identifies as female, few works try to deal with actual Transgender issues in anything like a realistic way. Since otokonoko is mainly an otaku thing, otokonoko are quite likely to wear Sailor Fuku, Meido, Miko, Cat Girl or Naughty Nurse Outfits as well as "ordinary" female clothes.

Some non-fiction magazines exist to provide advice and help with crossdressing for men who identify as otokonoko in Real Life and who crossdress to achieve the look (or want to).

Most otokonoko is technically seinen, although some is shounen. Works aimed at a female audience are never this, so don't list Shoujo, josei or boys' love.

Examples:

The following works either technically aren't Otokonoko or precede the establishment of Otokonoko as a genre, but have been influential in its development:

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Anime and Manga

Light Novels

I'm a Royal Tutor in My Sister's Dress revolves around a boy impersonating his older sister in order for the both of them to avoid execution.

Visual Novels

Otome wa Boku ni Koishiteru: Possibly the original "boy crossdresses to infiltrate an all-girl's school, gets involved in pseudo-lesbian sexual hijinks" story; released at a point where the genre didn't have a name and consequently advertised as "Girls' Love" even though the main character is male.

Josou Jinja is a fairly generic otokonoko gay Hentai Kinetic Novel which is mainly notable for being the first one in the genre to be not only released in English but also given a widespread release on Steam (under the name Trap Shrine).

Web Original

Otoko no Ko wa Meido Fuku ga Osuki!?: Four cute girls open and run a maid cafe (spoiler: they're not girls)

Real Life