Transvestites are people that dress in the accepted dress of an opposing gender for a variety of reasons. Many are wonderfully heterosexual ... they just match amazingly well.
Norse: When the mighty hammer Mjölnir is stolen by the Giant Þrymr, Þrymr demands the goddess Freya as payment. The Mighty Thunder God Thor decides "My, I would making a fetching lass" and dresses as Freya in order to steal the Hammer back. So with Loki as a bridesmaid (is anyone writing Thor 2 paying attention to this???) , the mighty manly God of Thunder dons yon dress and steals the hammer back during the honeymoon. To cap off the Norse version of The Crying Game, Thor takes down all the Giants involved. Hopefully, this was not after going down on any of them. This is all documented in the poem the Þrymskviða.
Greek: Herakles (read Hercules) killed Iphitos in a fit of madness over a complicated dispute about cattle. As a result, he was punished (not unlike a disobedient pain slut) and given to Omphale as a slave for a period of a year. In a missed portion of the Disney movie, Herakles was forced to do women's work by Omphale as slave punishment. Several versions of the story maintain that he was forced to wear women's clothing while performing said women's work.
They Say She Talks To Angels: The history of Joan of Arc is like really long to go into and junk. Here is the short version. She had a vision from God that the Brits were total assholes. God told her to kill the British in a Holy Crusade. She became the rarest figure in French history. She was a successfull military leader. Naturally, the French decided to reward this bravery with a trial as well as a famous burning at the stake. The upside is that she looked fabulous while doing it.
The Jazz Singer: Billy Tipton, born Dorothy Lucille Tipton, became a jazz band leader in the 1920's. The 'Billy Tipton' persona was originally adopted only for professional duties. Eventually, Tipton decided to live full time as a man. There was even several romantic relationships with women. One of the relationships to a former stripper named Kitty lasted decades. They even adopted three sons together. Tipton was active in the Boy Scouts with thier sons as well. Tipton claimed that thier chest needed to be bound and thier gentitals were hurt in a car accident. The truth was not fully known until an autopsy conducted afterr his/her death in 1989. This was when Tipton was 74 years old.
What I Really Want To Do is Direct: Ed Wood was a cult genius and director of such films as Glen or Glenda, Plan 9 From Outer Space, and Bride of the Monster. Of course, you can't make really bad cinema without wearing angora sweaters. Wood was more man than many of us. He was a paratrooper in World War 2. The impressive part? He was wearing bra and panties while he jumped out of airplanes. Wood later remarked that he did not fear death. He did have more than a little trepidation about the idea of getting wounded and discovered in a bra. He was dressed in angora sweaters by his mother growing up and according to his wife was more than heterosexual in the sack... he just wore hose afterwards.
One Bad Apple: One serial killer in Wisconsin and everyone starts to have a cow... Ed Gein was a killer, but mostly he just wanted to be a middle aged woman. To this end, he would rob graves and create fem suits out of women's skins. Of course, he sometimes found it neccessary to skin a live one or two as well. Gein would wear women's skin and often put on some sort of grease or oil to take care of that 'leathery feel.' Hell of a way to get rid of that 'not so fresh feeling.'
A Place Called Beaumont: Have you ever heard of Charles Beaumont? As a child, he was dressed in women's clothing by his domineering mother. He would also grow up to be one of the greatest science fiction writers of all time. You know all of those Twilight Zone episodes you often attribute to Rod Serling? Many of the creepiest ones were actually written by Charles Beaumont (born Charles Lerot Nutt). The list includes Perchance to Dream, Elegy, Long Live Walter Jameson, A Nice Place To Visit, The Howling Man, Static, The Prime Mover, Long Distance Call, Shadow Play, The Jungle, Dead Man's Shoes, The Fugitive, Person or Persons Unknown, Valley of the Shadow, In His Image, Miniature, Printer's Devil, The New Exhibit, Passage of The Lady Anne, Living Doll, Number 12 Looks Just Like You and Quuen of the Nile. Most of them were typed while wearing lovely flowered dresses.
J. Edgar: He ran the FBI. He wore women's clothes. We would say that mentioning it would be akin to flaggellation of a grmnivorous quadraped in an advanced state of rigor mortis but isn't that reallly just beating a dead horse?
Although crossdressing is not actually classified as a mental disorder, you could never tell that one by the people that cross dress in fiction. Apparently, crossdressers aren't interesting enough on thier own. There has too be some murder or an alien invasion involved. There are fun ones every now and again.
A Boy's Best Friend Is His Mother: Norman Bates was a different man in the Robert Bloch's novel Psycho than in the movie by Alfred Hitchcock. In the book, Bates was much more like Ed Gein ( and was a middle aged man.) In the movie, Bates wasn't a middle aged man until Psycho II and Psycho III and we guess to a lesser extent in Psycho IV : The Beginning. In Hitchcock's classic, Bates was a young attractive man. Anthony Perkins himself was every bit as complicated. Perkins was apparently a homosexual in his youth. Perkins later got married and turned his back on his homosexual youth. The Hitchcock version is the one stuck in popular imagination though.
Sweet Transvestite: In 1975's The Rocky Horror Picture Show, Dr. Frank-N-Furter discovers "the secret of life itself" by creating the monster Rocky Horror. Of course, you just aren't a mad scientist without doing all your work in make-up as well as fishnet stockings. For his trouble, Furter suspects that young lovers Brad and Janet are in league with ufologists. After a stint of cannibalism and more than a little song and dance- Furter is killed by his own underlings before ever returning to Transvestite, Transexual, Transylvania. On the upside, the writer is now a voice on Phineus and Ferb.
Red State: Nothing says family entertainment like Disney's Mulan. So nothing really says family entertainment now like a crossdresser saving China with the help of a Captain who is voiced by an open homosexual. Well, that is the speaking voice, the singing voice is Donni Osmond ... you can see the difference... oh well... never mind. At any rate, Mulan takes up her families honor by fighting for family honor against a Hun invasion. She gets discovered during an injury (which is surprisingly common in finding out women during wars), but still manages to save China with fireworks. Nothing says Chinese New Year like that. All of ... well most all of it... while crossdressing.
Legendary Director - In both the 1968 original and the 2005 musical, 'legendary director' Roger De Bris was a crossdresser as well as a homosexual. De Bris flamboyance as a crossdresser some time makes people forget that he was potrayed in the original The Producers by Christopher Hewitt. Christopher Hewitt would later achieve fame on the small sreen as lovable brit Mr. Belvedere. In the musical starring Nathan Lane (who himself would memorably go into drag in The Birdcage) and Matthew Broderick, De bris is portrayed by Gary Beach who would also dress as Adolf Hitler.
Successfully crossdressing is mostly centered around bulges. Namely, either hiding them or creating them. There are a few methods of this.
Gaffs - Gaffs are flattening type underwear to smooth out bulges that you can use under other underwear. Most of the theory is to first push the testicles into the original cavity and the rest back over it. Once the gaff is applied, then other clothing can be put over. Keeping everything in place can be tricky and may actually require taping. Just know that is actually ok to put gauze or a piece of cloth over the scrotal sack before taping it down. Otherwise, removal of the tape may also result in spontaneous confessions of assassinating John F. Kennedy Sr. and Jr. and any other Kennedy they can think of.
V Strings - V strings are actually prosthetics made of rubber or latex formed to look like a vagina. Elaborate models include hair as well as catheders designed to assist in urinating from a seated position. There are even masturbator V-String editions. These are designed to allow the tip of the penis to be exposed and function as a clitoris for the purpose of masturbation in a feminine style.
Of course, thier is not just taking away bulges, there have to be ones that are timely added as well. Padding the chest as well as the rear tends to require a bit more than tissue paper.
Breast Forms - Silicone breast forms were primarily developed for women who had mastectomies due to cancer. However, almost any technology can be developed for other purposes. Generally, they are free form and can be sort of glued on with a paste. It might be a good idea to shave the actual chest before trying this one. Breast forms are also attached onto clear see through bras straps in order to avoid unfortunate detachment.
Rear Padding - Forming the hips and buttucks can be almost equally important for proper effect. Popular ways to achieve the effect include overly padded girdles as well as attachable forms to the rear and hips. That also gets in to the who issue of gluing and indiscriminately painful hair removal.
Fem Suits - Fem Suits are latex body suits that do all of the shaping for you. There is also fem masks if your goal is to look like a completely plastic woman. Perfect for living doll fetishists. The suit itself will only set you back roughly as much as a downpayment on a new car,. Once the body form is established, it is all really a matter of establishing a style with clothes and make-up.
Sexual Fetishist - Some people get a sexual thrill from wearing the clothes of the opposing sex. There are also people that get a sexual thrill from dressing someone else in the clothes of the opposing sex.
Job or Positon - In order to participate or join in on a traditionally or exclusively dominated position by the other sex, people will dress in the clothes of the opposing sex. Women did this through many wars to participate in the military. One British woman even joined the army to track down her husband who had run away from home.
Entertainment - Actors in an all male environment would dress in women's clothes to potray female characters. There is a long history in comedy of men wearing women's clothing as men. Generally, comedians will obviously be men in women's clothing. There is also the industry of drag queens as well as female impersonators.
Raised as Crossdressers - Louis XIV's brother Phillipe was actually encouraged to wear girl's clothes as a child as well as an adult to curb potential desires to the throne. He was also encouraged to be homosexual. The homosexuality did not take as he would not only marry but take on mistresses. Parents will also allow children to crossdress in order to satisfy natural curiosities they may have. Attempts have also been made over the years to make crossdressing more socially acceptable with limited results.