Part 1: My Story

Hi all, my name is Ramona Richards but I go by Mona. I’m relatively new to the CDH community, having joined just before the holidays. By way of introduction, bear with me as I begin this article describing my crossdressing history.

Over the course of my almost six decades, I’ve followed the “typical” crossdressing career path (haha, as if anything about us crossdressers is typical):

Childhood: early fascination with dominant women and men in tights. Specifically, the original Batman TV series that ran during my formative years in the 60’s was a huge influence (apologies to younger folks who aren’t familiar with this show). I can recall identifying with Robin (the Boy Wonder) more than Batman, perhaps because my unconscious mind was drawn to his cute, colorful outfit and his role as the submissive partner to Batman. Then there was Julie Newmar as Cat Woman – smoking hot in her dominatrix-like catsuit. I remember being fascinated by the power she wielded in her efforts to entice and dominate Batman.

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So, there I am at the tender age of six or seven, unconsciously experiencing an erotic charge from the costumes and innuendo-laced interplay between characters on a campy TV show. Clearly, our sexuality is hardwired, and I realize this is not an earth-shattering revelation to many readers.

Early teens: beginning of “transvestic fetishism” phase – secretly wearing sister’s underthings for gratification – enough said.

College: no interest and, with roommates, not many opportunities anyway.

Adulthood: marriage, career, children – very sporadic bouts of secret CDing but still limited to underthings (wife’s) for erotic stimulation. Long stretches with no interest, including the past 20 years, up until Right Now.

Right Now: my wife of thirty-plus years and I are empty nesters. I love her and our kids, love my job as a scientist – in short, I have a great life. But about 6 months ago, the urge to cross dress hit me hard, seemingly out of nowhere. In response, I have spent a small fortune to go all in – wigs, makeup, clothes, shoes, etc. This is way beyond anything that has come before, and the intensity is surprising and frightening.

All of my crossdressing activity up to this point has taken place in secret, usually followed by feelings of guilt and shame that so many of us have experienced. A few months ago, after agonizing about it for months, I came out to my wife. She was shocked to say the least, but also appreciates the courage it took to be honest and vulnerable. However, she does not want to know any of the details. The few times I’ve brought it up since, her only response has been that she is still processing it. In the meantime, our tacit agreement is that she will tolerate it but is not inclined to discuss it – and certainly does not want to see any evidence.

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As with many of us, therefore, the only time I dress is when I’m home alone, and I am diligent about erasing all signs of my activities before she returns (I would make a good criminal, haha).

For me, dressing is an intoxicating activity. I’m a fairly typical middle-aged, balding, slightly overweight, suburban man whose day-to-day office wear consists of khakis and polo shirts (i.e., the casual corporate uniform). But for those few precious hours, I’m able to transcend the mundane routine of daily life, the often-mindless conformity, and magically transform myself into something soft and beautiful and sexy.

I believe this is perfectly logical: who doesn’t want to embody that which they love and desire? I think what sets many of us crossdressers apart is the strong drive to actually act out our fantasies. And here let me state that I am sensitive to the fact that for those in our community further along the gender spectrum, it is less a matter of fantasy and more about identity.

I‘m finding that I really enjoy the creative aspects of cross dressing – trying different combinations of wigs, makeup, clothes, etc. Basically, finding my style. Note to the gal on a budget: Salvation Army, Goodwill and Payless Shoe Stores are your friends.

Right now, it doesn’t feel like I’ve started down a path toward transitioning. I’m content with my life as a heterosexual man who enjoys a variety of interests and activities outside of crossdressing. Given my history of ebbs and flows, it’s possible that in a few months, my current strong urges will abate, maybe even go away completely for another extended interval (in which case I’ll be holding a hell of a fire sale, ladies!).

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Anyway, if you’re still reading this, thank you for grinding through all the long-winded navel gazing. From my research, I think I’ve followed a fairly typical (haha) trajectory. However, it’s only half the story, because as we know, saying yes to the dress is not without a good deal of distress. In addition to the fun, I’ve been struggling to understand what is happening to me. I believe this is also typical.


Part 2: The Questions I Ask Myself

Mainly the question is why? And why now?

When I look closely at my face in selfies, I see a woman smiling back with unbridled joy.  My eyes are sparkling, thrilled to behold the woman in the mirror, right there in front of me. It took me a while to realize that the look on my face is that of someone who has fallen in love. I think the technical term for this is gender euphoria.

This realization both excites and frightens me. Newly and wildly in love with myself, at my advanced middle age? WTF?

Now it’s time for my scientific side to enter the picture. This is the scientist who is hardwired to spend inordinate amounts of time reading and analyzing, and he is the one who is raising questions such as:

What are the psychological underpinnings of this form of “self-love”?

Am I just a guy in love with the woman I have created out of myself?

Or is my face in the photos that of the woman inside me bursting with joy after decades of repression, finally free to fall in love with herself?

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On the other hand (there is always an “on the other hand” in science), could this all just be an exercise in vanity and self-indulgence, a form of narcissism that is somehow a defect in my psyche?

Am I trying to fill a void for something else that is missing from my life? Wouldn’t I be better off focusing my time and energy on more “socially-acceptable” things, that might bring the same or more satisfaction?

What if I am publicly outed? Am I prepared to handle the fallout, including a ruined reputation, damaged relationships with friends and family, etc., etc.?

Is the sudden and intense resurgence of this activity a form of mid-life crisis? Could it be due to low testosterone or some other hormone imbalance? Mental disorder?

How about adult-onset gender dysphoria, with a sprinkling of residual transvestic fetishism and a dash of autogynephilia?

OK, that last question should convince you that I do indeed read too much. And believe me, I could go on and on with these kinds of questions.

The problem is that I haven’t found any satisfactory answers, and I’ve heard many others say that nobody ever really does. My goal in writing this is to share my thoughts and experience with the CDH community and perhaps spark some conservation.

I’ll end with a question to the millions of my fellow balding, middle-aged, khaki-clad men who at best view crossdressing with benign indifference and at worse as a deviant activity that, on the long list of atrocities that we humans have proven capable of, ranks right up there with the likes of genocide and child molestation. The question I pose is: if you had the opportunity to step outside yourself for a time to embody the beauty, femininity and alluring sexuality that women possess, would you do it?

In my opinion, those who answer no are missing out on experiencing a transformation that is magical, powerful and fascinating. So for the time being, at least, I’m saying not only yes, but hell yes to the dress.


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On-and-off CDing since early teens. Long stretches without any urges but here in my advanced middle age Mona has emerged in force. She's a high-spirited gal who shall no longer be denied. It's both thrilling and a bit intimidating because I don't know where she's planning to take me. Although I only get to dress every now and then, I'm having great fun and just enjoying the ride. I'm happy to have found this welcoming and supportive community and hope to get more involved as time allows.
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Josey Martin
4 years ago

Mona..thanks for sharing. I have been cross dressing for only 6-7 months and for the life of me do not know where it came from. I could go into detail about my life I have been married over 40 years and have always been a closet bisexual but never acted on it. Absolutely love women but fantasize about men only when masturbating and it has always been that way. My wife was away for the day and I was in our huge walk in closet and for some unknown reason had the urge to try her shoes on which is… Read more »

Deanna Lund
Active Member
4 years ago

Mona, Your story very much like mine. Very casual brief use CD bras, panties rarely with long intervals between. Until about a month ago. Coincident with joining CDH. At that point I met Deanna, made friends with lots of girls here. Started buying dresses, bras, panties, makeup wigs… Been out en femme. Have had moments when I think WTF am I doing? But they pass quickly! Last week while eating breakfast en femme at IHOP it struck me, [b][I]I Love Deanna![/i][/b] It felt totally clear, like pure, clear water. Not romantically, but a pure satisfying love feeling! Thanks Mona Luv… Read more »

Lori Profante
3 years ago


Amandah Opal
Active Member
10 months ago

Gosh Mona thanks for sharing, your narrative resonates with me entirely. I have dressed intermittently and clandestinely since my 20s, but now regularly and confidently in recent years with the wider acceptance of our LGBTQI+ community. The tension between my two personas has never really hounded me. I don’t have the typical dysphoria’s associated with surgical gender transitions, however under the DSM-5 Gender Dysphoria criteria I do satisfy the following when presenting as Amandah: A deep desire to transform into another gender A profound need for society to treat them as another gender A powerful assurance of having the characteristic… Read more »

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