Wednesday, July 26, 2023

’60’s Chick

Growing up as a crossdresser in the 1960’s was not a happy place to be. 

For starters, I had no idea what motivated me on that summer day in 1963 to go to my mother’s bedroom and try on a pair of her nylons and high heel shoes. That Pandora’s Box moment was the beginning of my 60-year love affair with crossdressing, but during those early days, it was a tumultuous affair.

I was very guilty about what I was doing. Heaven forbid that anyone found out that whenever I was home alone, I was exploring my mother’s and sister’s wardrobes. I was so closeted that when my best friend suggested that we dress up as girls for Halloween, I feigned complete disinterest, although in reality, I would have loved to have done it.

The closeting of my crossdressing was not as effective as I thought because in retrospect, all the evidence indicates that my parents knew what I was doing, but they never confronted me about it.

The closet was very stifling. After honing my crossdressing skills in private for almost half a decade, I had to let the girl out of the confines of the closet. So on Halloween 1969, I borrowed my sister’s purple mini-dress, black mid-heel pumps, black tights, wiglet and knit beige cap. I wore minimal makeup. Although I had been wearing my mother’s and sister’s foundation garments in secret for years, I skipped the bra and girdle because I did not think they would appreciate me wearing such personal items.

Mind you, I had no place to go. I was too old to trick-or-treat, I had not been invited to any Halloween parties and I was too young to go bar-hopping. So I drove around town visiting a few friends and relatives, who were amused by my costume. I don’t know if I passed (I’m sure I did not), but I did not care. I was having the time of my life! All I cared about was that I was out in public living a few hours as the young woman I had discovered and nourished for the past few years.

👠 👠 👠

While searching the Internet for an appropriate image to accompany today’s post, I came upon something completely different: Mantis Lady Vintage, a website that sells vintage woman’s clothing. The site is the creation of Edward V. Cantwell, who not only sells the vintage clothing, but models it, too!

Source: Cynthia Rowley
Wearing Cynthia Rowley

Mark before, Jan after


  1. Wow, what's Mark's secret?!? I would love to be able to knock six inches off of my height when I am dressed pretty!

  2. AnonymousJuly 26, 2023

    I'm a sixties chick times two: In my sixties and I dressed up as a girl for the first time in the 1960's. For years and years I've wondered why as a 12 year old boy, one evening while home alone,I felt this sudden urge to try on one of my mom's dresses that was on a hanger in my parent's bathroom.

    It was a beautiful silk dress and putting it on wasn't satisfying enough so I found a girdle, nylons, and a slip. I felt a rush of adrenaline and fabulous sensations as mom's dress swished around falling just below my knees.

    "Is this what it feels like to be a girl," I asked myself over and over again? The moment I took off mom's dress and put her undergarments away I was wracked with guilt admonishing myself for doing something so out of step with the boy I thought I was.

    Today, as far as I know there is no one in my life who has an inkling that I love putting on feminine garments. My wife knows, but early in our marriage I confided this, whatever you want to call it, to her. She wasn't thrilled to learn of it either, but we love each other and it isn't part of our lives together.

    However, all my life I keep asking why? Why did I find mom's dress irresistible that day? Why do I continue to envy femininity? Why does that swish of a dress still excite me? I don't think I'll ever have an answer.

    1. I was also 12 when one day I was overcome by a need to try on the skirt, blouse and pantyhose my mother had left in her bathroom. It felt wonderful and I immediately got working on ways to try on everything in my mother’s and sister’s wardrobes without detection.
      I also wondered if this what it was like to “be a girl”. 45 years later, the only thing that makes sense to me is that wearing pretty clothes is to know what it’s like to be feminine.
      Just as some women love hunting, camping, fishing and sports, my interest in skirts and all of the associated items and techniques for using them simply expands the culturally defined limits of my gender role. There is nothing wrong with that.

  3. AnonymousJuly 26, 2023

    Love that Cynthia Rowley dress....perfect to wear to see Barbie! I wonder how many of us will go see Barbie dressed to the nines.. Lauren

    1. I saw "Barbie" but didn't go as Mikki. I did wear a fun pink T-shirt. It's a bowling shirt that says, "Dolls with Balls", with a ball hitting pins on the lower part. I pointed out that all of the characters are dolls, including Ken. The other word shows I'm not Ken. Ha!

  4. AnonymousJuly 28, 2023

    I was 10 when curiosity got the better of me. I wanted to know what wearing tights felt like. I then moved on to trying bras, girdles and dresses. One day, buried at the bottom of a drawer I found an old fashioned girdle and stockings. This became my go to lingerie. I was a member of an all boys youth group. Every year we would put on a display. I was lucky to get a girls part 4 or 5 times. I loved getting the parts especially as a teenager as you were given full outfits, wigs and full makeup to wear. Happy days although thinking back my mother must have known what I was doing but she never said anything if she did.

  5. AnonymousJuly 28, 2023

    My parents were homophobic and tried their best to catch me in the act. Why? Well, I tried on my mother's sole black bra in the days gone by when clothes did not have stretch. I popped one of the bra straps. I tucked it back into her lingerie draw. She had to have seen it. One day I had slipped in a sun dress that was kept in the clothes closet in my bedroom. I thought I had carefully monitored where my mother and father were outside our sixth floor apartment. Yikes! If it wasn't for the security chain on the apartment door they would have caught me. My father tried to bust through the chain, but it held. I had time to strip off the dress, hang it back and feint that I had been on the toilet. I escaped. I don't know what would have happened if I had been caught. I suspect, after high school instead of going to college I would have been tossed out of the house, ended up being drafted and killed in Vietnam.

  6. AnonymousJuly 28, 2023

    As a young teen I attended an all boys summer camp. One year our tennis counselor was a beautiful woman named Amy who was the wife of the camp's assistant director. My cabin group decided to put on for the summer's end show a skit about tennis. We needed a boy to portray our tennis counselor. We drew lots and I was chosen to be her.

    Amy cheerfully loaned me a white pleated tennis skirt, top, and pink sneakers. She helped me with my make up and loaned me earrings too. As a fourteen year old I made a somewhat credible girl. Somehow, in spite of the teasing I felt powerful wearing her skirt and loved it.

    Several months later I decided I wanted to dress up as a girl for a Halloween party. I asked my mother if she'd let me. She helped and seemed quite willing to let me dress up as fancy as I wanted. That was exactly what I did.

    I love wearing skirts and dresses and do so every chance I get.