Crossdressing

There are various ways to say "crossdressing" in Japanese, depending on what you mean.

1. josou
   女装
   Literally "female clothes," can refer to guys crossdressing. This is the most common term.
2. dansou
   男装
   Literally "male clothes," can refer to girls crossdressing.
3. iseisou
   異性装
   Literally "opposite-gender clothes," means crossdressing in general. This is the least common term.

Left: Utsumi Shou 内海将
Middle: Takarada Rikka 宝多六花
Right Hibiki Yuuta 響裕太
Anime: SSSS.GRIDMAN (Episode 8, Stitch)

• Grammar
• Crossdresser
• A面, B面
• Pronouns
• Breasts
• Double

Grammar

Grammatically, all three words can be used as suru-verbs.

• josou suru
  女装する
  (For a guy) to crossdress.
• josou saseru
  女装させる
  To force [a guy] to crossdress.
  (causative form.)
• josou saserareru
  女装させられる
  (For a guy) to be forced to crossdress.
  (passive form of causative form.)

• dansou suru
  男装する
  (For a girl) to crossdress.
• dansou saseru
  男装させる
  To force [a girl] to crossdress.
• dansou saserareru
  男装させられる
  (For a girl) to be forced to crossdress.

Almost every word that works for one gender has a pretty obvious opposite equivalent.

• {onna-mono no} shitagi
  女物の下着
  Underwear [that] {is a female-thing}.
  Female underwear.
• {otoko-mono no} shitagi
  男物の下着
  Male underwear.

Crossdresser

There are various ways to say "crossdresser" in Japanese. Using relative clauses and compound nouns, you could say:

• {josou suru} hito
  女装する人
  A person [who] {crossdresses [by wearing women's clothes]}.
  • josou suru danshi
    女装する男子
    A guy [who] {crossdresses}.
  • josou-danshi
    女装男子
    A crossdressing-guy.
• {dansou suru} hito
  男装する人
  A person [who] {crossdressed [by wearing men's clothes]}.
  • {dansou suru} joshi
    男装する女子
    A girl [who] {crossdresses}.
  • dansou-joshi
    男装女子
    A crossdressing-girl.

Besides these, there are also specific terms for people who aren't simply crossdressing, but that are known to crossdress. For example:

• josoko
  女装子
  A guy who crossdresses. (as a hobby, for example.)
  • Pronounced josoko じょそこ with a short vowel.
  • The word ko 子 generally implies a cute person.
• dansouko
  男装子
  A girl who crossdresses.
• josou-sha, and dansou-sha
  女装者, 男装者
  Crosdressing person. A crossdresser.
• josou-ka, and dansou-ka
  女装家, 男装家
  Crossdresser. (as a craft, like crossdressers that are TV personalities.)

A面, B面

There are terms to refer to the periods of time a crossdresser is crossdressing and the periods they are not.

• ee-men
  Ａ面（エー・めん）
  Side-A. (in music)
  While crossdressing. (for crossdressers.)
  • men 面 means a face. In music, some discs are double-sided, meaning one of its faces has a set of songs, and flipping it around allows you play a different set of songs from the same disc
• bii-men
  Ｂ面（ビー・めん）
  Side-B. (in music)
  The non-crossdressing side.
  • Example: his B-side is a shop clerk. Meaning: when he's not crossdressing, he's a shop clerk.

In English, similar terms are "boy mode" and "girl mode." However, note that side-B can mean either boy mode or girl mode depending on your gender, while side-A can also mean either, but it's the opposite gender instead.

Pronouns

In Japanese, there are multiple first person pronouns and some of them are used more by one gender than the other, as such, a crossdressing character may switch pronouns to fit the intended gender.

For example, ore 俺 and boku 僕 are masculine pronouns, so a girl crossdressing may use them. Girls that use the pronouns are sometimes called orekko オレっ娘 and bokukko ボクっ娘 respectively.

The pronoun watashi 私 is feminine in casual contexts, while atashi あたし and using your own name as pronoun are just feminine in general.

Breasts

The lack or presence of breasts hints one's gender, so crossdressers may make them appear out of nowhere, or disappear into nowhere, at will.

Character: Koibuchi Kuranosuke 鯉淵蔵之介
Anime: Kuragehime 海月姫 (Episode 3)

• Context: a male crossdresser pads his chest.
• ginyuu
  偽乳
  Fake breasts.

Character: Konoe Subaru 近衛スバル
Anime: Mayo Chiki! まよチキ！ (Episode 2)

• Context: a female crossdresser makes her chest flat.
• sarashi
  さらし
  The term for this white cloth wrapped around the chest.

Double

In some cases, you have a situation in which both guys and girls are crossdressing for some reason.

For example, some series feature a school event in which participants have to wear the opposite gender's clothes.

Sometimes, it's just just a character quirk.

Left: Aura Bella Fiora アウラ・ベラ・フィオーラ
Right: Mare Bello Fiore マーレ・ベロ・フィオーレ
Anime: Overlord, オーバーロード (Episode 1)

• Context: this trap and reverse trap pair of siblings are in-game monsters created by a player who canonically likes that sort of stuff, and probably likes heterochromia, too.

Other times it's because a complicated situation was taken to the next level by making it even more complicated.

Left: Makoto マコト
Right: Minami Touma 南冬馬
Anime: Minami-ke みなみけ (Episode 10)

• Context: wanting to get closer to Minami Chiaki 南千秋, Makoto disguises himself as Mako-chan マコちゃん, and pretends to be one of her older sister's friends in order to get invited to their house to play. In a completely unrelated turn of events, Chiaki decides to adopt Touma as her younger brother, despite Touma being an older girl, and so Touma starts dressing as a boy, too.