Cross-dressing is the act of wearing items of clothing and other accoutrements commonly associated with the opposite sex within a particular society. Cross-dressing has been used for purposes of disguise, comfort, and self-expression in modern times and throughout history. There is a nice article about the history in mythology.
A transvestic fetishist is a person who cross-dresses as part of a sexual fetish. The term underdressing is used by male cross-dressers to describe wearing female undergarments under their male clothes. The famous low-budget film-maker Edward D. Wood, Jr. said he often wore women’s underwear under his military uniform as a Marine during World War II. Female masking is a form of cross-dressing in which men wear masks that present them as female.
Sometimes either member of a heterosexual couple will cross-dress in order to arouse the other. For example, the male might wear skirts or lingerie and/or the female will wear boxers or other male clothing. Sometimes the chrossdressing is part of forced feminization.
A different description is Petticoat punishment, also known as forced feminization, petticoating or pinaforing and sometimes abbreviated PP, is a kind of roleplay or fantasy that revolves around a male being dressed as a girl in front of his mother, sisters, or in some cases, girls of his own age whom he had offended by his boorish behavior. It is a kind of forced cross-dressing for punishment, a form of psychological punishment. Petticoat punishment is sometimes combined with other humiliating punishments such as forced nudity and spanking. It is related to Ageplay, BDSM, femdom, malesub, and fetishism. A male subjected to petticoat punishment is sometimes referred to as a “Sissy”.
“When petticoat discipline was first employed we will never know. A study of social history shows that it was discussed in family magazines and newspapers during Victorian and Edwardian times, and the beautifully decorated and belaced girls’ fashions of the times would no doubt have made them especially effective at subduing the high spirits of boys who required firm discipline. Certainly, as we can see from family photographs of the time, it was the fashion until the Great War to dress both little girls and little boys in virtually identical clothing; beribboned vests, petticoats, white lace dresses, and big bonnets, often until the age of five or six. Some men who were brought up in these times, including former British Prime Minister Harold Macmillan (Lord Stockton), recalled being dressed by their nannies in especially pretty and girlish clothing for some minor offence, and petticoat discipline is mentioned in Jonathan Gathorne-Hardy’s excellent book ‘The Rise and Fall of the British Nanny’, published in 1972.” (Source)
There have been many artists who illustrated about this theme. For those searching for this theme I tried to bring artists and art on this theme together on this page by creating albums solely dedicated to the cross-dressing art from the particular artist. Visit the artist page to see more art on different bdsm themes. This is not a complete collection of all the sissy, petticoat punishment and cross-dressing art that can be found on my site. It is just too much work to browse through thousands artworks in order to connect a single image to a new album. So I strongly advice you to take your time and browse my site to discover more.
There are also some ancient books on this theme. Most known perhaps is Frederique, written by Don Brennus Alera (Roland Brevannes)