A common question asked cross-dressers is, "Why do you dress like a woman?" There are several problems with that question. First of all the querent assumes 'woman' means 'female' mistaking gender for sex. Secondly one does not dress 'like' a woman, as someone who is 'dressed' is a woman since they are presenting as feminine. That's what woman means; someone who is feminine.
My fundamental tendency would be to respond, "To be pretty!", which is true but the complications arise when one considers the motivations for being pretty. Those motivations are several, if not many, and vary in underlying causes.
Perhaps a more explanatory response would be, "I dress to be feminine because, like others male and female, I enjoy bringing Beauty to the world and being a part of that Beauty." The key in the response is to bring up the fact 'dressing' is not solely a male behaviour but that females often indulge as well. Your motivations are the same as any other woman's. If the enquirer can comprehend that some people (regardless of sex) may want to be feminine and beautiful then they may be able to comprehend why a male might wish to be feminine and beautiful. It is a difficult concept to convey, especially to either an androphilic or gynecophilic, masculine, gender invariant males, as they have never experienced the desire to be feminine and, without that experience, will find it difficult to understand why anyone would have such a desire.
It is equally difficult to explain to an androphilic, feminine, gender invariant female. In part this may be because they cannot understand why a male would 'surrender their male prerogatives', because their desire for a gynecophilic, masculine, gender invariant male makes any alternative unpalatable and because their fairly limited view creates the illusion of normality versus abnormality. Essentially their desire for the security that 'normality' offers would overwhelm any understanding of variant behaviour.
The important thing, I guess, is to take the opportunity to educate others but it is equally important to understand your own motives. Without that personal insight one can never make others understand. To say one likes 'dressing' or that it makes them feel good simply raises the question as to why one feels good. There are a variety of possible responses to that question, including the creation of chemicals such as serotonin, sexual arousal, a feeling that one is manifesting one's true being, the pleasure inherent feeling that one is attractive, the sense of accomplishment in creativity, the attraction of the essentially complex of interacting aspects of beautification, etc. The interest in complexity is actually a relatively masculine component. It has similarities in fascinations with speculative fiction (Star Trek), mechanical creativity (model trains, motor vehicles), sports (the mathematical and statical elements of baseball), role-playing games, etc. These similarities cause some persons to identify cross-dressing as a hobby; a designation that can raise some ire. While there is some rationality in the comparison, identifying cross-dressing as a hobby is unlikely to be the whole of the matter. There are too many other hobbies, even obsessions, to engage one's attention to make such a simplistic evaluation.
It is far more likely that cross-dressing is a result of a combination of the above-mentioned factors. Perhaps, for some, one factor is more prevalent or more outstanding that others. This would explain why cross-dressers not only find difficulties in agreeing on any particular motivation but why they disagree on the significance of several such motives. This can result in a fair amount of confusion.
Even more important is the probability that cross-dressing results from two factors, a predisposition to femininity and the ability to be gender variant. There may be other ways of expressing one's desire to be feminine (essentially a socially defined collection of conventional, personality traits) without cross-dressing. It is those who tend to be more adaptable in their gender presentation who gravitate to cross-dressing. It may seem self-evident that those who are essentially gender invariant would be unlikely to be cross-dressers but that factor, and even the concept of gender invariance, seem rarely considered.
Perhaps revealing is a fairly recent query regarding the motivations for cross-dressing. Persons were asked to respond with one word. I took these words and attempted to categorize them. Granting the subjectivity of my typology, I feel the results are intriguing. There were 124 responses that I fitted together. There were more responses but some were unsuitably ambiguous and the others came after my tabulation. My categories, and some specific terms used, included:
Freedom: 38. 30.6%.
liberating, expression, security, natural, myself, freeing, identity, validating, freedom, proper, necessary, fulfilling, self-fulfillment, moksha: a state of enlightenment and self-realization, V'ree'lat – Vulcan: to order one's thoughts and clear one's mind, Me!, femininity, completeness, enlightening, balance, equilibrium, necessary, normal.
Appearance-sensuality: 27. 21.8%
heels, tactility, sensual, softandsilky, shoes, wigs, beauty, cutesy, sweet-sexy, lipstick, shopping, style.
Ease of tension: 23. 18.6%
soothing, comfort, calming, relaxing, calming, tranquility, escape, decrossstressed, peaceful, relief, happier, surrendering.
Emotional response: 21: 16.9%
exhilarating, satisfying, thrilling, euphoria, happiness, girly, happy, scary, excitement, awesome, essence, wonderful, breathtaking, fabulous, everything, delightful, exciting, ecstatic, stimulating.
Amusement: 9. 7.3%
fun, dancing, sensational, enjoyable, creativity, enjoyment.
Sex: 4. 3.2%
erotic, orgasmic
Response from others: 1. 0.8 %
attention.
Egotism: 1. 0.8%
egotism.
In all probability, any one respondent might have chosen several categories as being more-or-less equally important. For example while only 30.6% of respondents felt that being liberated from the restraints of social expectations was the most important factor, it is probable that this was also important for many of the other respondents as will. It would appear that such freedom, combined with the desire to create a specific appearance and the sensuality of that creation should be combined to define an overall motivation. That is one desires to be attractive for the feelings of joy, self appreciation, tactility and the self-actualizations created by achieving these objectives.
Perhaps surprising is the relegation of sexuality to a less prominent role. I would suspect, judging from numerous accounts, that this is more an indication of priorities rather than leading to the conclusion that sexuality is insignificant. It is just that being free to express ourselves in relationship to our surroundings in the manner that we find the most comfortable, even sensuous, manner creates a sense of correctness and genuineness that far overwhelms other considerations.
A particular motive for cross-dressing is the gender invariant desire to be feminine. More properly, being gender invariant, such persons are irrevocably feminine. It is just that society expects, even demands, that we behave according to conventional expectations based on sex. This is a major example of the hardships inflicted on individuals based on the assumption that sex and gender are the same. In the case of femininity this causes little distress if one is a feminine, gender invariant female or even, in most instances, if one is a feminine, gender variant female. However, if one is a feminine, gender invariant male the problems are enormous. Such a person, in their desire to actively express their femininity, will likely turn to cross-dressing initially. Eventually this will be unsatisfactory and unfulfilling and, as knowledge expands, the desire to fully feminize one's anatomy become conclusively the only available solution. In this instance, cross-dressing is more a superficial stage on the way to self discovery. This still leaves the examination of the motivations of MtF (masculine to feminine), gender variant males.
Without a great deal of deliberation, I feel that fundamental elements of motivation, acting singly or in concert, are:
To be feminine and pretty.
To create (or to be) a sex object for fantasy activities.
To escape social pressures.
To fulfill a sincere and overwhelming desire to be a woman (feminine, not female).
To enjoy a sense of euphoria and wellbeing, possibly biochemically induced.
To reflect personality changes brought about by maturation.
All of these are consistent with the concept of 'feeling good' but also need wider consideration for understanding. For example, how do we define what is actually feminine? How do we recognize beauty and is there a general agreement on what is beautiful? What is the nature of any euphoria (the opposite of dysphoria) experienced? How does (if it does) personality change with maturity?
The assertions that one cross-dresses to 'be pretty' or 'to feel' good' are actually complex. Peeling away the layers of that complexity reveals greater complexities. Like many such questions there may be no ultimate answers as, ultimately, we begin to ponder such elements of our existence that border on the metaphysical. Nevertheless by sounding the profundities of cross-dressing we may find ourselves with increased self-confidence and with the ability to help others to understand why we have these desires and needs.
In the foregoing on the motivations of cross-dressing I tended to downplay the effects of sexuality. This is misleading and an error on my part. My intention was to indicate that sexuality, while significant, is not the whole reason for cross-dressing, nor always a principle reason. This, however, is not always true and it is especially untrue in the instances of the onset of cross-dressing in pubescent males. Aside from the various Freudian concepts regarding sexual attraction and other elements of psychoanalysis, it seems intuitively and experientially likely that young males become sexually intrigued to a high degree about the ages of 10-13. To quote myself:
“Young males are sexual. This is not to suggest that young females are not it is just that young males are really, really, really sexual. They desire, generally, femininity in their lives. This is often denied them. One solution is the creation of femininity. This might be an acquisition of publications that cater to prurient interests or, more recently, an avid search for online pornography. Another means of sexual contact with femininity is making use of the services of a professional sex worker. There are several solutions, none quite satisfactory as the element of mutuality is usually absent.
“Should the young male also have a predisposition to femininity or, in some instances, be an incognizant transsexual person there would arise a certain curiosity not only about women but also about being a woman. While cross-dressing is evident in a statistically small number of males the conception of possibly creating femininity through the proper adornment of one's own body seems more widely prevalent. If I do an online search using the question, "How many men think about trying on women's clothing?" about 72 to 129 million results are indicated. Granted that perhaps only a small portion of these is relevant in any way but the question seems to have occurred to a few other persons other than myself. Since the proportion of males who become cross-dressers seems relatively small it would appear that many consider the possibility, many experiment but only some have a predisposition that drives them to seek femininity as well as, or instead of, sexuality.”
Even here I did not go into the matter as much as I should of and I do not intend to go into the matter here as much as I can. There are some very intriguing theories that amplify on the theme but I wish only to make a particular point. That point is that, in seeking to actively slake their sexual urges, young males may ‘stumble’ upon cross-dressing as a means of creating a sexual object. Intriguingly this is somewhat different from seeking an object of desire if only because of the creative element. I call this:
"I Feel Pretty!"
“Cross-dressing might find its onset during puberty. If a boy has not had his mind and value systems warped by interjected values previously this may represent a change more than an onset. Suddenly girls become of greater interest. Not as persons but as objects, goals, targets and prey.
“Advertising, television, magazines, video games, the whole western cultural imagery, creates the 'standard' image of a desirable female. This is not so much a matter of beauty as desirability. What some may find objectionable or distasteful is extremely arousing to others. Sometimes they are identical, as the forbidden fruit seems to be the most tantalizing. Thus a female pop singer can wear highly rigid, external 'underwear', creating an artificial and exaggerated concept of the feminine form and still be considered 'sexy' by some. Sex sells and it usually sells to the sexually immature. Exposure to advertising in the past 40-50 years has multiplied ten-fold. Not only has feminine imagery become sexualized and idealized but it has become essentially fictionalized. One needs only compare the number of instances of scantily clad females to instances of scantily clad males (without scantily clad females) to see a definite, sexualized objectification of females.
“Based on anecdotes I suspect that the onset of cross-dressing is more likely in the pre-school years. Very young girls have a delight in appearing feminine and pretty. The concept of being pretty seems to centre on the senses that focus on bright colours, shiny trinkets, sensuous fabrics, movement and, sometimes, extravagant shapes. This is extended to smells and taste (strawberry flavoured lip gloss) and to cosmetic colours. There are distinct differences in style between girls, young ladies and more sophisticated women. It's called, "Dressing your age!" Very young boys who might be attracted to the same sensations might well be envious of their female counterparts and wish to share the same sensations of being pretty. As a rule, parents, teachers and peers pretty soon put an abrupt stop to such behaviour.
“Most Western, school-aged boys exhibit a style of drab colours even military camouflage. They also dress in conformation to the established dictates of what is 'cool' usually in modes evocative of competition, violence, high-risk activities and death. The sexes are also segregated. Not so much as they were 50 years ago (when boys and girls had separate entrances to schools) but still noticeably. This creates the impression that the difference between sexes is of greater significance then it might be, or that the differences that do not really matter are of more significance than the differences that do matter.
“Desires created by new emotions result in fantasy objects. A sexual partner is unlikely to be available and other factors (i.e., sheer terror of rejection by the opposite sex or condemnation as a sexual pervert by the community) may be relevant. Usually the boy will be gynephilic, really (I mean really, really) liking girls, and be terrified of having his desires discovered by family and peers. Curiosity leads to experimentation with mothers' and sisters' undergarments.
“Eventually, one wishes to experience the 'full effect'. Aside from elements of narcissism the effect can be startling. One sees in the mirror a 'sexy girl' ready to be the object of one's desire. This creates a mild sexual addiction. In later years, this may diminish if opportunities to develop the practice are rare and 'real' women become available.
“At first the person in the mirror has no particular name or personality. She is an object and, as gender often is itself, part of a fantasy. If sufficient opportunities present themselves she may acquire a name (often a ludicrous reflection of her role as a sexual object) and even develop a personality. Many cross-dressers report a change in behaviour when 'dressed'. Sometimes some elements of that change impinge onto the 'male' portion of their lives.
“The adolescent for whom cross-dressing has become a sexual experience finds the process of 'dressing' is itself sexually provocative. Even the anticipation of the opportunity is exciting, possibly partially due to the possibility of discovery. 'Dressing' is a form of foreplay.
“In later years, as the feminine personality becomes more developed, this feeling of anticipation, excitement and wellbeing may be diminished but evident. Sexual release is sometimes immediately followed by the loss of the desire to athenase and even distaste and a sense of guilt. Older cross-dressers report dressing to 'feel good' more than for sexual excitement. Ingesting chocolate is also supposed to be mildly arousing and to make one feel slightly euphoric. Thus one becomes addicted to chocolate (although the sugar content may be a major factor as well). Presumably this is a chemically induced effect. There is the release of Phenylethylamine and Serotonin connected to feelings of passion or eroticism. They also create a sense of wellbeing and euphoria. Cross-dressing does the same. While possibly slightly addictive, cross-dressing is not fattening.
“Perhaps ironically Serotonin production likely increases with the production of testosterone. One 'treatment' for 'transvestism' is the administration of drugs that increases serotonin. Side effects include Sexual dysfunction, seizures, obesity and nausea. Other drugs (some known as 'selective serotonin reuptake inhibitors' or 'SSRI') were lithium carbonate to treat transsexual persons. It seems probable that chemicals, whether naturally produced or artificially administered, are involved. It should be noted that regarding cross-dressing as a paraphilia is highly debated and that equating it with Obsessive Compulsive Disorder has no support. Chemical treatment for OCD has had some results but a similar treatment for cross-dressing has been generally negative.
“The sense of beauty-attractiveness and the need for sexual exploration seem related. A boy who finds he has available (and that he is) a pretty girl is liable to take advantage of the situation for exploratory purposes as well as from the desire to be attractive. The desire to be pretty, attractive or beautiful is similar to the goals of any person who takes the time and effort to dress fully. It is probable that some females share the same exhilaration and excitement the process has for some males. How else can the massive amounts of money spent on clothing, jewelry, cosmetics, fad diets and beauty parlours be explained?”
“Consider how often one reads of someone who ‘discovered’ cross-dressing as the result of a Hallowe’en prank or effort, an entertainment such as a play or skit, some dare or jest or simply an almost random experimentation with the clothing of a relative. For many, this may be pleasurable but not particularly life altering. There are, as indicated above, numerous other avenues of exploration. For some it is an epiphany. There is the recognition that, deep within themselves, there is a need to be feminine that demands to be made manifest and once released the genie is not going back into the bottle. The practice may, at least initially, continue as a predominately sexual pastime particularly as the opportunities for cross-dressing will likely be limited; however, the passage of time, acclimatization, developed experience and greater opportunities will possibly create a desire to athenase for more than simply sexual motivations. For some, cross-dressing will no longer be sufficient and, in the case of Early Onset Transsexuality, the need to transition will become overwhelming.
“An element to consider, but I will not expand on here, is that a young male’s sexual focus might evolve from seeking a sexual object to creating a sexual object to being a sexual object. This suggests a chain of events by which gynephilic males can initially see themselves primarily as sexually masculine but can eventually also see themselves as sexually feminine. This is a matter of sexual identity rather than of motivation. My purpose here is to add to the above motivations the importance of considering sexual motivations and the effects they have.”
Minerva.