Crossdressing Two Decades Into the 21st Century

A few weeks ago, I told you about my friend Linda and her planned ‘retirement’ from crossdressing. It may come as a surprise to you but not to me that the next time we got together via Skype she was wearing a lovely pale blue sheath dress necklace and matching earrings. While we were seated most of the time, she did stand to show me the striking navy-blue two-inch heels that helped shape her to-die-for legs. One month and she was already out of retirement. You can purge the girl’s wardrobe but apparently you cannot purge the girl’s personality.

Linda and I have had some fun recalling the decades in our lives as crossdressers. Most of our recollections have been personal but not those from the 1960s or ’70s. We are not THAT old.

So, it was a bit of a surprise for us to get together to talk about the decades of the 21^st Century only to discover that we may not have the clearest perspective on what has been happening with us crossdressers in the last 20 years. Maybe we are TOO old. Perhaps you readers can help us out here.

When Linda and I started crossdressing, it was some 50+ years ago and the word had not yet come into general use. “When you started going to the library to find information about your ‘particular interest’, Linda asked as her fingers made that quotation make gesture, “what did you find?”

“You know that in the minds of the sexologists and the public we did not really exist,” I replied. “I remember reading that in the transgender world there were transexuals—those who had or were in the process of obtaining a change of gender. There were drag queens who adopted a female guise for entertainment purposes, there were homosexual men who sometimes dressed as women to attract other men and there were transvestites who could get sexual pleasure from wearing a few articles of feminine clothing.”

“And that was it!” Linda responded as if she was congratulating one of her college students for giving the correct response. “In the minds of the world we did not exist. Sexologists like Masters & Johnson and Albert Kinsey wrote extensively about human sexual habits and proclivities but failed to identify the people, mostly males, who dressed themselves in the apparel of the other gender simply for the pleasure of dressing and acting as one of the opposite gender.” Linda and I excepted, sexual activity was and is not a big part of crossdressers’ activity and for so many the thought of sex with other males plays no part at all. Perhaps the sexologists preferred that we did not exist. But thanks to people like Virginia Prince and others the term crossdresser made its way into the public lexicon.

“But how do you define the term crossdresser?” Linda was again putting me on the spot.

“To me, we are people who dress and appear in the clothes and style of the opposite gender for the purpose of enjoying some time, however brief, feeling like a member of the opposite gender.”

“Is passing an important part of crossdressing?” Linda asked rhetorically.

“To me it is” I replied, “Not all of us are going to achieve it but I think we should be trying, not only in how we dress but how we do our makeup, how we talk, how we walk, how we sit, how we laugh and in so many different mannerisms that differentiate females from males of our species. If we don’t 100% pass, our appearance is still expected to be inoffensive to the people around us.”

“That is the way I see it, too,” my friend Linda took over, “but did you know that as we have been growing older the meaning of the term crossdresser seems to have been redefined in a way neither of us would agree.”

“What do you mean? I must have missed the memo.”

“I first noticed it back in the days of Craigslist personals, “Linda continued, “I would get into a town and post an ad with photos identifying myself as a crossdresser and the photos would show myself in my best effort at passing. Inevitably a few of the respondents would say they were crossdressers but their photos and sometimes their notes made it clear their idea of crossdressing was to put on some feminine lingerie and work at bringing themselves to a climax.”

“To me that is not a crossdresser; that’s a transvestite,” I interjected. “But yes, I noticed that, too. I didn’t take them too seriously and figured they had a right to call themselves what they wanted even if they were inflating their status.”

“Inflating their status? Well, aren’t you a proper snob!” Linda said while putting on that annoying British accent she sometimes effected.

“Didn’t it bother you that you might one time identify yourself as a CD and some folks would shy away figuring you were just into a bit of erotic lingerie and not the full package?”

“Oh, I was one step ahead of them,” she replied quickly. “I started describing myself as a pre-op TS. It was none of their business what my end goal would be but folks who were looking for a ‘chick with dick’ would know exactly where they stood with me.

“With me too,” I admitted. “So, you and I both self-identified as crossdressers but to much of the rest of the world we called ourselves something different. Shouldn’t we have been pushing back against the transvestites?”

“It was not my battle to fight,” exclaimed Linda.

That evening Linda and I broke off our Skype chat without resolving the history of crossdressing in the 21^st Century. That will have to wait, I decided. I determined to find out how and if the definition of a crossdresser had shifted from the pen of Virginia Prince to today’s Wikipedia and dictionaries.

In my work I use Wikipedia quite a bit. So naturally it was my first source for information about the modern definition of crossdressing. Linda was correct. The yardsticks have moved quite a bit in the last more than half-century since the word was coined.

Here’s part of Wikipedia on ‘cross-dressing’: “The phenomenon of cross-dressing is seen throughout recorded history, being referred to as far back as the Hebrew Bible. The terms to describe it have changed throughout history; the Anglo-Saxon-rooted term “cross-dresser” has largely superseded the Latin-origin term “transvestite”, which has come to be seen as outdated and derogatory.”

Wrong, wrong, wrong I say. The term crossdresser was inserted in the transgender spectrum not to include the transvestites but to distinguish us from them.

Is the term ‘transvestite’ derogatory? I guess it is if you consider putting on a bra and panties to ‘get yourself off’ a demeaning activity but to each their own, I say. We have no business knowing what others are doing in private. ‘If the stiletto fits; wear it,’ as they say.

The champions of crossdressing of the 1950s and1960s thought it very important to distinguish the growing numbers of males who enjoyed appearing as female as they could but were not in it for the sexual activity or pleasure they could derive. They wanted an identity separate from the transvestic self-pleasuring at one end of the spectrum and the man-seeking homosexuals on the way to the other. Transsexual individuals were considered way along that spectrum, in a zone most crossdressers did not consider possible or desirable to achieve.

For a while our champions found an identity in the word crossdressing and in them (us) being crossdressers. This is because the latter was historically used to diagnose psychiatric disorders (e.g. transvestic fetishism), but the former was coined by the transgender community.[3][6] The Oxford English Dictionary gives 1911 as the earliest citation of the term “cross-dressing”, by Edward Carpenter: “Cross-dressing must be taken as a general indication of, and a cognate phenomenon to, homosexuality”. In 1928, Havelock Ellis used the two terms “cross-dressing” and “transvestism” interchangeably. The earliest citations for “cross-dress” and “cross-dresser” are 1966 and 1976 respectively.[7]

Do you believe there is a predictable cycle to the life of a crossdresser? You know just like these documentaries about creatures in the wild. A calf/cub/chick will be born/hatched then spend some time being nurtured/fed by one or more adult in the species before heading out on its own. There it faces some dangers as it forages on its own, eventually finding a mate, mating and creating more calves/cubs or chicks.

For the crossdresser species it varies from one to another but a common theme I hear is that the typical MTF crossdresser discovers ‘the desire’ sometime between the age of six and twelve. Some earlier; some later.

Some get to realize that for them it is more than ‘just crossdressing’. They realize they were meant to be female and they are going for it. That realization may come earlier in life, pre-teen even. It may come later in life. I know of one person in his late 40s, with no previous connection to the local CD community, suddenly came out and told his wife and three teenage children that he was going to be undergoing gender reassignment.

I know another who lived the life of a CD into her 50s. Sadly her wife passed away after battling cancer. That enabled our friend to embark on a several year journey to becoming the woman she says she was always meant to be. She told me recently that the surgical journey is now completed.

Enough about them. We’re talking about crossdressers here. We enjoy presenting ourselves with a feminine image. Sometimes we present just to ourselves, our mirror and our camera. Sometimes we present to the world.

Linda and I talked about it once and decided that if there were to be a National Geographic documentary about the life cycle of the crossdresser it would probably include that period of self-discovery as a young male sniffing around and then trying on his mother’s or sister’s lingerie. There might even be those where “my girlfriend made me do it and I liked it”.

Next would come the period of self-growth and self-discovery where the crossdresser experiments with his art but keeps the practice to himself. He knows that those around him are not likely to appreciate his compulsion or his choice. As the crossdresser grows the crossdresser will probably want to grow to larger and larger closets. It’s not just the literal kind although Linda and I both went through periods of having to find larger suitcases, then storage boxes, storage lockers, then in her case a shared apartment to keep all her femme apparel and accessories.

Crossdressers: if it hasn’t happened for you yet, be prepared! Some day in some way someone you know and probably love is going to discover your ‘hobby’. It may be accidental, or it may be that you can’t keep the secret any longer but for most of us the secret does come out. That is where our documentary would have to split down so many avenues. The reactions and the rest of our lives can be so different depending on who we are and who are the people in our lives.

Linda and I both think that life has become much easier for the outed crossdresser of the 21^st Century than it was for those of the 1950s and ’60s. We never seem to face the derision or even second glances that were so often featured in personal stories of CDs venturing out in those past decades.

Nor does it seem that the discovery of a husband’s CD habit is an express route to divorce court, loss of job and financial ruin.

We have some possible explanations for the public’s and the courts’ apparent change in attitude. We ask if you agree:

• Has there been enough publicity and discussion about transgender subjects that it no longer generates the xenophobic reaction of the past?
• Has there been enough sightings of CDs in public places such as malls and restaurants that we are no longer considered ‘freak show’ characters? Is there such a thing as herd immunity to crossdresser sightings?
• Do people who read us just not care to say anything to their friends for fear of being admonished to ‘leave her be’?
• Do some ‘good old boys’ who might otherwise call us out, think that just maybe the CD they see just might be the next ‘crazy with a gun’ who might use it if threatened with even a wisecrack? So, they think what they think but keep it to themselves. It was my observation that we all tend to keep more to ourselves than in previous decades.
• Like Linda observed, do people just not notice other people because they themselves have their eyes glued to their smartphone screen?

I told Linda that recently I had spent several days in a town in Ontario, Canada. It is a very tourism dependent town where seven months of the year everybody knows everybody else and their business but from mid-May to almost mid-October the town is bustling with busloads and carloads of visitors. Some visitors just stay a day or two and move on. Some settle in for a week or more. Some are drawn to the river activity, some the casino. I thought that the locals would be very curious about the strangers they see coming to town. I was visiting and living full time en femme just before the start of the tourist high season. Like the first daffodils, the first robins or wild turkeys I expected some reactions from the locals. That creates some anticipation and adrenaline rush for me but no responses were forthcoming? Was it me? Was it the Covid mask I was wearing in the stores or do people just not care about crossdressers anymore?

Linda and I leave it to you to answer the questions above and to give us all your opinions on crossdressing in the 21^st Century.

Like to make a comment? Login here and use the comment area below.

Tags: crossdressing, featured

Category: crossdressing