Retro Rerun: Why Crossdress? 28 Reasonable Reasons

As an aspiring fiction writer, I’m naturally concerned with questions of motivation: for what plausible reason would a fictional character choose to do something sufficiently unusual to provide the driving force for a short story or novel? One such question, which I would expect to be of great interest to most TGF members, is this: Why would a male choose to dress as a female? With a little thought, I’ve arrived at a list of twenty-eight possible answers, with both real-life and fictional examples where I could find them. I won’t presume to call this a definitive list, because as soon as I do, someone will come up with a dozen more reasons that haven’t occurred to me.

Fictional crossdressers can be found in many places–myth, ancient and contemporary literature, comic strips, plays, movies, and television. The creators of these works usually seem to feel a need to assure their unnerved readers (or viewers) that a sympathetic character’s crossdressing activities are just temporary expedients and that he will soon be back to normal (a twisted villain, on the other hand, does not necessarily provoke authorial reassurance). In these stories, crossdressing is usually forced or at least made appropriate by external circumstances; the protagonist happily reverts to manly garb when these circumstances have been overcome.

In the last few years, there has been a trend toward the presentation of sympathetic characters who dress because they must (the wonderful British novel I Want What I Want is an excellent example), but these remain a minority. Here, the circumstances leading to crossdressing are internal and what must be overcome are society’s many obstacles to the protagonist’s happiness as a transgenderist.

In compiling my list, I’ve made an effort to find reasons that are general enough to cover a number of similar cases and are yet distinctive enough not to overlap. In some cases, I may be splitting hairs; in others, I may be failing to see the differences between apples and oranges.

I’ve divided my reasons into four broad categories, the first of which is to please someone or suit someone’s agenda (6 reasons). This category is popular with writers of crossdressing fiction and fantasies, whose stories are often characterized by both external and internal forces–a relative or friend requires or coerces a male (usually young) to crossdress, and this act is instrumental in the protagonist’s discovery of his true transgender state.

1) The male is forced to dress as a female, either as punishment or to humiliate him. This is one of two classic fictional/fantasy themes. Johnny is bad, so his angry mother forces him to wear his sister’s clothes. Grown-up John displeases his girlfriend, who decides to humiliate him by making him wear one of her dresses. In straight fiction or in real life, most males punished this way will rip off their sisters’ or girlfriends’ dresses as soon as they are permitted to do so, and they’ll never go near them again. In crossdresser fantasy and occasionally in real life, Johnny discovers and later embraces his feminine side, but he can always say it wasn’t his fault; he was forced into it. My real life example comes from my sister, who once showed me photographs of her young sons in dresses–a punishment, as I recall.

2) He wears female clothing to please an encouraging, facilitating, or coercing relative or friend. This is the other classic fictional/fantasy theme. It seems to resonate with a frequently-expressed crossdresser’s wish for a female mentor to help him with clothing purchases and makeup techniques and to guide and assist him as he goes out into the world en femme. I know of no better fictional example than Peta Wilson’s excellent Power Dressing, published about a year ago in TGF. [In 1997.] Author Ernest Hemingway was a real-life example; his mother apparently forced him to dress as a girl for several years, until he neared puberty.

3) He is a young child who’s been raised as a girl and doesn’t know he’s a boy. Although this sounds like fiction, I have only a real-life example. Several years ago, a distraught young father wrote to Ann Landers to complain that his wife was raising their young son as a girl. “Jackie,” who was about four or five at the time, had no reason to believe he was anything other than a girl–he wore dresses and frilly underwear, and his mother was teaching him to behave as a girl. The mother’s model was Ernest Hemingway’s mother, and she planned to enlighten “Jackie” when he was about to enter puberty. That could be about now–I hope she’s set aside a small fortune for counseling.

4) He is a young boy who is dressed as a girl for cultural reasons. Again, I have no fictional examples. In his notes for The Greek Myths, Robert Graves wrote of an ancient Greek custom of dressing boys in royal families as girls and raising them in the women’s quarters of the palaces. This practice was an important element of the Achilles and Dionysus myths. In more modern times, young boys were often dressed as girls for the first few years of their lives. In his study of transvestism, Dressing Up, Peter Ackroyd reproduces a portrait of young Prince William of England (1743-1805) garbed in an elaborate dress. He also shows a photograph from around 1896 of the future King Edward VIII, at the age of two, in a lacy dress and curls.

5) He is required to dress as a female as the penalty for losing a wager. I have no examples, but I feel certain that this has happened in both fiction and reality.

6) He is disguised as a female for the convenience of his homosexual lover, so they can give the appearance of being a conventional heterosexual couple. Once again, I have no examples, but I feel quite certain that there are both fictional and real-life occurrences of this.

The second general category of reasons involves crossdressing to enable the crossdresser to do something that can’t be done any other way (6 reasons). (One must concede that this may demonstrate either the subject’s limited imagination or the author’s personal predilections.)

7) The male disguises himself as a woman to accomplish a mission, quite often one that has been imposed upon him as a matter of patriotic duty. The best-known real-life example is probably 18th-century France’s Chevalier Charles d’Eon. In 1755, the 27-year-old d’Eon was sent by the French government to serve as a spy in the court of Empress Elizabeth of Russia. To carry out this mission, he assumed the guise of a young woman named Mme. de Beaumont. Crossdressing as a woman to accomplish a mission is a popular theme in fiction as diverse as the plays Charley’s Aunt and M. Butterfly; Georgette Heyer’s Regency romance, The Masqueraders; and countless comic book adventures.

8) He disguises himself as a woman to be with or near his beloved. There are many real-life examples of women disguising themselves as men to follow their husbands or sweethearts into battle. I can’t cite any specific examples of men dressing as women to be near their wives or girlfriends, but I suspect that it has happened–a teenager seeking to infiltrate a girls’ school or camp, for example. This has certainly been a movie plot device, and it was also a plot element in the Gilbert and Sullivan operetta, Princess Ida. In this case, Prince Hilarion and two friends disguise themselves as women to invade the fortress of the ultra-feminist Princess Ida. She was betrothed to the Prince when she was one and he was two, and now, twenty years later, he means to claim his bride.

9) He disguises himself as a woman to escape danger, capture, or imprisonment. In real life, Charles Stuart of Scotland (Bonnie Prince Charlie) disguised himself as a woman to evade capture when his military effort to free Scotland from England collapsed. Jefferson Davis, president of the defeated Confederate States of America, disguised himself as a woman in an effort to escape from a Union prison. There have been many other instances of men disguising themselves to escape from prison by walking out in the midst of a crowd of female visitors. There have also been many cases of men disguising themselves as women (both in fiction and in real life) to commit crimes and (they hope) evade capture.

10) He disguises himself as a woman to meet the requirements of religious ritual. In his notes to The Greek Myths, Robert Graves states that ritual crossdressing occurred during the long transition from a matriarchal religion and rule to patriarchy as “the king deputized for the Queen at many sacred functions, dressed in her robes, wore false breasts, borrowed her lunar axe as a symbol of power, and even took over from her the magical art of rainmaking”.

11) He disguises himself to earn a living in a woman’s job. (Not too many years ago, kiddies, there were “men’s jobs” and “women’s jobs.” Now, the non-TG male job seeker would simply file a lawsuit instead of assuming a disguise.) The real-life example here is one of the child actors in the old Our Gang films. One of the gang was supposed to be a girl, but the part was played by a boy who was initially presented to audiences as a girl. In the fictional realm, we can turn to the comic strip Apartment 3G. In one series of episodes, a writer who had submitted a manuscript under a woman’s name had to disguise himself as a woman when a publisher accepted the manuscript and wanted the author(ess) to promote the book on talk shows.

12) He disguises himself to win a wager that he could successfully pass as a woman. Sorry; no examples–but I’ll bet it’s happened!

The third general category of reasons is to entertain (4 reasons). Since entertainment involves real people performing for other real people, I won’t try to cite fictional examples, although I feel certain that there are fictional counterparts for some or all of my real-life examples.

13) The male performs the role of a man dressed as a woman. There are many movie examples: Jack Lemmon and Tony Curtis in Some Like It Hot; Dustin Hoffman in Tootsie; Patrick Swayze, Wesley Snipes, and John Leguizamo in To Wong Foo; and the three drag queens in Priscilla, Queen of the Desert.

14) He performs the role of a woman. This is not the same as Number 13. Examples come mostly from the stage–ancient Greek and Roman theatre, English Elizabethan theatre, Japanese Noh theatre, and Chinese opera were all closed to females, and males performed all female roles. In the last few years, there have been a number of examples of men taking female roles in off-Broadway and regional theatre productions. Note: In each of these examples, we have actors, known to be male, dressed as women. A TG earning a living as an actress doesn’t count here, because she’s identified as a woman (this is where the hair-splitting begins in earnest).

15) He entertains as a female impersonator. The performer presents himself as a male impersonating females, usually well-known actresses and singers. He does brief impressions rather than extended stories (as in Numbers 13 and 14). Danny LaRue, a British pioneer in glamour female impersonation, deviated from this by playing leading roles in a number of plays and films and the title role in a television production of Charley’s Aunt.

16) He entertains by burlesquing or denigrating women. In British pantomimes, which are usually broad takeoffs on classic fairy tales, there are invariably one or two “dame” parts–the Ugly Sisters in Cinderella, for example–that are played as burlesque roles by male actors.

The fourth category, to please himself, contains twelve reasons, almost half of the total 28. We are now getting down to TG reality. A male dressing as a female for one of the sixteen reasons above is not necessarily transgender, although he may be. If his reason is one of the twelve below, he is quite likely to be TG. Crossdressing for money or glory doesn’t make one a crossdresser, but crossdressing for pleasure usually does.

In her September 1997 Sexy Vampire column in TGF, Kalina Isato offered six responses to the question, “Why do crossdressers crossdress?” They all fall into the “to please himself” category:

• It’s fun
• It feels good
• To be someone else for a while
• To fool men
• To pick up men
• To worship women

In general, I won’t try to provide examples for the twelve reasons below. You can find most of them in any issue of TGF.

17) The male dresses as a female to play a joke on someone.

18) He crossdresses for amusement; e.g., as a guest at a costume party.

19) He crossdresses out of curiosity; he wants to see how it looks and know how it feels.

20) He dresses as a female for sexual pleasure. Crossdressing is an erotic experience for him.

21) He dresses as a female for aesthetic pleasure. He loves his appearance as a woman.

22) He dresses as a female for psychological satisfaction. He feels better when he is crossdressed, whether or not crossdressing gives him erotic or aesthetic pleasure.

23) He dresses as a female for the thrill of doing the forbidden and risking discovery.

24) He dresses as a female to make his appearance match his psychological gender.

25) He dresses as a female because he believes he’s really a woman.

26) He dresses as a female in order to live as a woman, whether or not he believes he’s really a woman.

27) He dresses as a female to attract a male.

28) He dresses as a female to demonstrate admiration for/solidarity with women.

And there we have it. That’s my list of reasons.

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Tags: crossdressing, featured, opinion

Category: Transgender Opinion