Bi And Buy -- Sex Self-Help
Victoria King

 


Cross-dressing: hobby or hang-up?

I saw him sitting at the bar and was intrigued. He had to be at least 6’4", well-built, sandy blonde hair, green eyes and a roguish grin: I had to admit though he made a really ugly woman! What possibly possessed such a good-looking guy to cross-dress and publicly was a mystery to me. I couldn’t help but watch and see what clues the evening might offer me. His "Laura Ashley" outfit was far too conservative for a "professional" and whenever some mousy wall-street type in a three-piece suit offered to buy him a drink he politely declined. What was amazing was how many women approached him! With the pretty ones he exchanged phone numbers with the not so pretty he simply chatted until they got bored and left him alone. When I saw him get up and head for the rest rooms I could no longer contain my curiosity. I followed him and he seemed to sense my presence. Before entering the men’s room he turned and smiled at me…

"I still pee standing up."

I couldn’t help but laugh. When I emerged from the ladies room he was waiting for me. He offered to buy me a drink and I could hardly refuse after being "discovered". Over a bourbon soda he revealed his secret and I was quite surprised.

"It’s still a new game but the possibilities are endless. When I go out as a "guy" on the best of nights I maybe meet two maximum three somewhat interesting women. With this gear even on a weeknight I go home with at least ten to fifteen phone numbers. You have to admit the odds are a hell of a lot better!"

"How do you explain it?"

"Simple psychology, I’m in advertising… A good-looking guy is intimidating but a good-looking guy in drag is an enigma. After all even your curiosity got the better of you right? There is no cudo for a woman’s ego quite like snatching a man from the brink of homosexuality, the ultimate challenge. It holds the same appeal as a mission from God."

"Isn’t it a little bizarre knowing that every woman you meet wants to ‘save’ you? If you just do it to have a more varied selection, in other words to get laid, I can appreciate that. It is hardly a basis for a relationship though…"

"For better or worse I’m married to my work, at least for the time being. Just having a little fun. Most of these women only see me as a conquest anyway, as soon as I get a hard on and ejaculate their mission's accomplished. You really think any one of them would actually marry a guy they know is a ‘cross-dresser’? I must admit though this little game of mine has made me realize just what you gals put up with. I can understand the war paint: it’s a jungle out there!"

* * *

She was without a doubt the most exotic and flawless creature I had ever seen: tall, slender, graceful, chic with delicate features. I found myself following her through the arcades of Les Halles without really knowing why. She entered a boutique and I inadvertently had to stop to get my bearings. I had been so captivated I really didn’t know where I was. She emerged once again with a playful expression and introduced herself. Her voice was breathy and ethereal but the hand that gripped mine could have easily belonged to a long-shoreman. I couldn’t help but stare at it in amazement and "she" laughed lightly. I asked if she would join me for a coffee and shortly thereafter we settled down at a table at a market café. Jasmine, once upon a time Jean Pierre, for personal and professional reasons had donned the costume of the opposite sex. She was still "intact" from the waist down, as it turned out that was a professional advantage, but medical science had provided her with a lovely décolleté that any self-respecting female would envy. With a sad smile she glanced down at her hands, the give away, a part of her anatomy that surgery could not "feminize"… The feet at least could be hidden; the hands even in gloves would always belong to Jean Pierre. I seemed to provide a pleasant distraction for her, under normal circumstances the only tourists she ever met were those who engaged her services. She had started on the stroll but had been quickly recruited by a posh escort service. There was an unbelievable demand for "working girls" with her equipment. I was amazed to learn just how many respectable businessmen secretly desired to be buggered by a beautiful woman. Another surprise was when she told me how many couples on first or second honeymoons contracted her talents. Sometimes the husband wanted to see his wife being fucked by another "woman" in other instances the wife wanted to see her husband get buggered by another woman… Soon my mind was reeling. As we finished our coffees she excused herself, she had important clients to entertain that evening and couldn’t afford to miss her body wax. As we stood she looked me over with an appraising eye…

"Pity you don’t have a penis darling we could make so much money together!"

With a kiss on both cheeks she trotted off to hail a cab leaving me there to stare after her open mouthed.

 

The grass is always greener… Aside from the economic motives for cross-dressing there are often other psychological incentives as well. Since the days of ancient theatre where men also played the roles of women cross-dressing has an undeniable allure. None feared or envied woman’s natural role of mother so much as the Christian clergy. In our century many men have envied the behavior package called woman. In most cases they only see the up side: desiring to be coddled, coveted, catered to…worshiped as a "sex object". Of course in reality only the tiny minority of the female population ever enjoyed such treatment. Having a spouse to attend to economic responsibilities can scarcely be considered over payment for assuming the responsibilities of motherhood, child rearing and household management.

Strange as it may seem cross-dressing is one area of erotic behavior attributed only to men. A woman who seeks to look and behave "masculine" is just considered a garden-variety dike where a man who dons the garments of the opposite sex is a cross-dresser who may or may not have homosexual tendencies. What is it that compels a man either to dress in women’s clothing or to seek the erotic companionship of a transvestite? With the exception of those who are "professionals" the answer is almost always guilt.

The chap I mentioned at the beginning of the section is a rare case indeed, having discovered cross-dressing as a way to "score". For the majority of men who wear women’s clothing either in private or public this is really a form of psychological humiliation, in their mind to look and behave like a woman is really a form of punishment. Mommy dearest usually has a lot to do with this (mis)conception. The man who desires to have intercourse with a transvestite generally carries tremendous guilt for his "pathetic" sexual desires and thus seeks to carry them out with someone who at least "looks" like a woman. That surprised me initially but it was confirmed by more than 100 professional transvestites I have spoken with over the years. Only one in a hundred of their customers want to fuck them. Two out of ten just want blowjobs the rest with out exception want to be fucked. (That is why having a penis, especially a large penis is a "professional" advantage)

Society has contributed in myriad ways to humanity’s unhappiness this is yet another. When the feminine is seen as something weak, second-class, in many cases abnormal is it any wonder that the "oldest profession" is not only thriving but constantly diversifying into new branches of activity? When to be female is seen as a punishment rather than something natural this not only generates misunderstanding but also impedes the sexual and therefore psychological development of our species.

I am astounded whenever I encounter a woman, a young woman who still refers to menstruation as "the curse". What is merely nature’s way of letting us know the system works is still considered by many to be some kind of biblical punishment, a source of shame. Sure it’s inconvenient in some situations but so is getting a hard on in public and that phenomena isn’t limited to a few days out of the month!

I used to wonder why for Halloween, Mardi Gras, Carnival etc so many women and men dress up as harlots. I also used to wonder what harlots dress up as… Later when I researched the history of carnival, its social significance and its root in ancient fertility rights of Spring it became a bit clearer. The carnival domino was a behavioral carte blanche. As those with fetish patterns seek to conceal identity in order to facilitate their erotic projections the carnival domino was the great social equalizer allowing its wearer to partake in otherwise taboo practices albeit once a year. Identity, position, age, gender could all be concealed liberating the wearer from their social constraints and allowing them to experience the forbidden.

The development of cinema then television and along with them merchandising finally did away with the traditional domino and the expressions of repressed fantasy became all the more blatant and specific. The common denominator almost always an expression of repressed sexuality. How many demure bank tellers have I seen suddenly transformed into whip wielding vixens in spike heels and fishnet stockings! The most remarkable is that it isn’t just the costume they don but the persona as well. How many burly guys have I seen in mini skirts and blonde wigs rubbing up against their buddies and giggling in glee when their ass gets grabbed! It would help if they’d shave the beards and moustaches but few are willing to go that far.

For those whose sexuality is less repressed fantasies take on more power oriented manifestations: pimps, pashas, police officers…

We all like to play dress-up; it can be a fun and revealing form of self-expression. This is yet another way we can act out our fantasies with our partners. The shame is when we feel the need to hide it, even from ourselves, or develop some form of "dual" life. With responsibility and sensitivity we can spread light and cast away the shadows. The more we evoke all of the elements of our personality and come to grips with them the greater our conscious participation in our own spiritual and psychological evolution. Our choices will no longer be governed by our fears. Our own knowledge and experience will play a counseling role in our decision making process and thus we can avoid the bad habit of seeking to assign blame every time something does not go as we would hope or secretly expect. As I have stated elsewhere what we do is not so important as how we go about it and what we understand in the process. If we are responsible and ruthlessly sincere even our "taboo" experiences can become invaluable steps on the path to self-knowledge.

 

 

Copyright © 2000 Victoria King
Published on the World Wide Web by "www.storymania.com"