Crossdressing In The Mid-20th Century

Tami’s Adventures In Crossdressing, Part 4

By Tami

My last chapter related how I was first exposed to another crossdresser who was trying on high heels in Frederick’s of Hollywood’s flagship store on Sunset Boulevard in LA. He was dressed in drab except for wearing stockings and having bright pink polish on his toes.    

That was the first time I had solid proof that there were others like me who enjoyed wearing clothing intended for females. Of course I knew that there were drag queens and female impersonators, but I considered them professional actors, not males who wore female attire for non-professional reasons. As far as my untrained radar could tell, the male in Fredericks did not appear to be a drag queen or female impersonator; he seemed to be trying on high heels just because he wanted to wear them.

I returned home from Tinsel Town with a renewed interest in wearing ladies fashions. This was before the internet existed, so the only sources of information on crossdressing were in printed publications I discovered in a shop specializing in men’s magazines. Within the pages of magazines and newspapers like En Femme, TV-TS Tapestry and LadyLike, the world of femulation began to reveal itself to me.

Thanks to online digital archives, you can still look through the pages of these treasure troves from the past (see links below). 

It’s easier for crossdressers and transexuals to find resources and information today thanks to the internet. Before the internet existed, information wasn’t easy to get; it was limited to those lucky enough to have local support groups or access to the few publications that catered to our interests. In those pages I read about other males who transformed themselves into females, often with amazingly genuine results. The photos of many of these gurls made them look like they were born and raised female. 

In addition to the stories and photos, there were listings for local cd/tv/ts support groups all over the country, plus ads for other resources I didn’t know existed. Makeover services specializing in male-to-female transformations were the first to draw my attention. There were actually stores that sold women’s clothing, but were focused only on male crossdressing customers.

There was an ad for a store near enough to me in New York City, Lee’s Mardi Gras Boutique, which offered everything a boy needed to look like a girl: wigs, corsets, girdles, panties, bras, lingerie, stockings, large-size high heels, pretty wigs, gaffs (at this point I didn’t even know what that was), breast forms, jewelry,  everything! There were professional voice coaches offering their services to help you speak in a feminine voice, services offering hair removal by waxing and electrolysis, even psychological counselors, and pages of pages of personal ads from crossdressers and transexuals. 

Within these publications I also discovered that there were conventions for crossdressers, like one in Provincetown on Cape Cod, where men wearing dresses, stockings, heels, makeup and wigs could walk the streets with no problems, right alongside the regular folk. Stana has often written here about her adventures at this annual event, previously known as Fantasia Fair, now known as TransWeek. 

This was beyond unimaginable to the young adult version of me and I dreamed to dare participate one day. An entire ecosystem for crossdressers existed, all laid out in a few very select magazines and newspapers. There was no Google search to find anything and everything, but there were plenty of resources, much more than I ever imagined.

The first thing I did after this sudden education was to visit that store in the Meatpacking District of Manhattan. In my next installment here on Femulate, I will relate the experience of shopping at Lee’s Mardi Gras Boutique, where I actually tried on girdles and all sorts of lingerie, plus high heels, wigs and dresses. From those first steps wearing female clothing other than my older sisters’s and mother’s apparel, other further adventures in crossdressing followed, thanks to my education on the wide world of crossdressing.

   https://www.digitaltransgenderarchive.net/files/fx719m53g

   
https://archive.org/details/ladylike25unse/mode/2up

   
https://archive.org/details/enfemmemagazine1990unse_1/mode/2up

If you click on the cover of the various issues, the magazine will open and you can digitally flip through the pages or in some magazines, you can just scroll down. 

I hope you enjoy time traveling back to the olden days of crossdressing as you peruse these publications!

Wearing ModCloth

Kenneth Williams and Charles Hawtrey femulating in the 1960 British film Carry On Constables.
Click here to view this femulation on YouTube.

Tami’s Adventures in Crossdressing, Part 2

By Tami

In my last post I provided an overview of myself, limited to my proclivity to crossdress and I observed comparisons and differences between myself and our hostess with the mostess, the lovely and naturally feminine Stana.

Today I will reach back under the many petticoat-like layers of my memory and start at the beginning, back to the later part of the 1950’s, when I first slipped on panties, stockings clipped to the garters of girdles or garter belts, satiny, lace-trimmed slips and the like.


I was fortunate to be able to choose from my two older sisters’ and my mothers’ dresser drawers and closets full of feminine finery. The selections before me were almost limitless. My only restriction was finding enough alone-time in our house to don these soft and feminine garments. When I knew everyone would be out for a long period of time, I would slip into their rooms, pick out some lingerie from their drawers, head into their walk-in closets and slip into lots of different slinky, soft clothing items.

I’m not sure if I would be as tempted to do this if I were growing up today as the typical female everyday wardrobe of 2025 is not that radically different from a male wardrobe – slacks, wool or cotton socks, low heel or no heel shoes, courser fabrics overall, shirts instead of billowy blouses, etc. Of course most women do own some softer more feminine “girly” clothing, but that seems relegated to more special occasions or if required for working in an office or reserved for nights in the boudoir. It’s a rare sight to see my favorite girly-girl item on any female today: sheer sensuous stockings. To me the bare leg look just isn’t as special. ’Tis a shame that sensuous slips and the like have mostly slipped away.

Anyway, I was a lucky child who loved female attire and had many amazing selections for my occasional forays into dressing like a girl. I tried on every girly concoction I could and admired the view of myself in a full-length mirror, not only while wearing the wondrous lingerie –- ruffled lace trimmed satin panties, longline bras trimmed with lace, satiny girdles, garter belts, sheer stockings, slips, petticoats – but eventually, if time allowed, I also donned their high heels, dresses, skirts, blouses, clip-on earrings, bracelets, necklaces, hair bows, pretty hats with lace and nets covering one’s face and the like. No one in my house had wigs, so I had to make do with my short male hair. 

I didn’t dare try to use makeup because I worried about removing it completely and understood that anything that was slightly used might be noticed. I would have loved to try the full effect of all female attire and makeup, even spraying myself with perfume, but that never happened in my youthful experiments with crossdressing at home.

Another benefit of growing up at that period of the utmost feminine finery was the proliferation of one of my favorite girly item of all: petticoats. The fullest and pouffiest were designed to hold out the wide skirts of gowns. My sisters had two gowns each, one for the junior prom and one for the senior prom. They were my very favorites, chiffon and satin with long skirts, held out by layer after layer after layer of crinolines and petticoats. Wearing them was like turning yourself into a floating cloud. 

I couldn’t get enough of anything with a petticoat. Wearing a gown or even a shorter skirt demanded that you give it a twirl, something that took some concentration when tottering on delicate shoes with thin, spiky high heels. I don’t have any photos of those actual beautiful gowns I sometimes got to wear, but I have included photos of gowns similar to them.

In case anyone wonders, if I ever got caught dressed as a girl, the answer is no, but it was close one time. I was almost done putting everything carefully back when I heard the garage door open and I had to rush. Like Stana, I wonder if they ever noticed anything amiss, but I suspect my sisters probably thought the other sister had borrowed something and put it back. If my crossdressing escapades were ever suspected I never heard about it. 

Does any of this sound familiar to any of you out there? Did any of you ever get caught, or admit to anyone what you were up to?

 Let us know in your comments and please ask any questions you may have!


Here are some link to pages that take a detailed look into the oh-so-feminine ladies’ wear of the 1950’s.

 

Lingerie: https://www.ohsodelightful.com/what-they-wore-1940s-lingerie-and-shapewear/


Prom Gowns: https://www.ohsodelightful.com/what-they-wore-1950s-prom/ 



I’ll leave you with the lyrics of a song from the fifties that perfectly describes the special relationship to special clothing that all girls shared way back then. 

Bobby Sox to Stockings

By Frankie Avalon, 1956

When a girl changes from bobby sox to stockings

And she starts trading her baby toys for boys

When that once-shy little sleepyhead

Learns about love and its lilt

You can bet that the change

Is more than from cotton to silk

If a miss wants to be kissed instead of cuddled

And to this you are in doubt as what to say

When a girl changes from bobby sox to stockings

Then she's old enough to give her heart away

(Songwriters: Clarence Way Kehner / Richard Di Cicco / Russell Faith. Bobby Sox to Stockings lyrics © Universal Music Publishing Group)

In my future installments I will relate my first experiences dressing like a girl outside of my childhood home and eventually relate my crossdressing up to the present day. Hope you are enjoying dressing like a girl half as much as I do, that would still be a lot!

From this fan of feminine finery, thanks for following along.

Wearing Amanda Uprichard

John Inman femulating on British television’s Are You Being Served?

Amy and the Doctor

By Amy

Today, our regular contributor, Amy, writes about finding self-improvement in the doctor's office.

With self-improvement foremost in my mind, I have followed the zillions of magazine pieces written on face lifts, nose jobs, eyebrow lifts, neck lifts, etc. I have read everything I can on facial feminization surgery and all that can be accomplished. I perpetually come back to my own base line appearance and count my blessings; no prominent brow bone; no Adam's apple; reasonable cheek bones; very good skin. (Thanks Mom!)

I did conclude that as I was aging some areas of my face were showing signs of drooping as fat and collagen were naturally lessening. I embarked on meeting with several dermatologists which turned out to be the best series of meetings, advice and support I could imagine.

Early on, I started in boy mode. Each doctor I met was a woman specializing in helping women look their best. I was right up front. I wanted to improve my appearance, to be more youthful, and have a soft feminine look.

The first of these doctors didn’t miss a beat and started me on a program called Thermage. You need to look into it, but in short, it is a form of laser passed over your face with the effect of triggering your skin to replenish lost collagen. For my skin type and other variables, the multiple sessions were very successful. An added benefit is that the laser greatly thinned my beard in the most natural way. What remains of my facial hair is thin, light in color, hidden easily under a very light foundation.

Secondly, I started on a prescription of Retin A. I have used it nightly for years. The evenness of color of my skin, the noticeably reduced pore size and near elimination of black heads is amazing. I use it everywhere below the eyes as my skin under my brows won’t tolerate it. I will never quit using this!

My appearance definitely improved and I began seeing all my doctors as Amy. At every office the staff and doctors cheered me on and enthusiastically helped me begin with new products. Dermal fillers were coming of age as was Botox.

I started eliminating frown lines between my eyes and filling little imperfections with these amazing products. They needed to be replenished, but I have found that by staying on schedule, I built a good foundation and moved forward.

Recently Juvaderm came on the scene and it was recommended I enhance my cheeks slightly for a more feminine shape. A more feminine contour was easily achieved and the skin under my eyes tightened and smoothed noticeably. Every place I have used fillers has served to make up volume in my face and slightly tightened the surrounding areas. Years melted away and people notice!

I now see four different doctors for these various tune ups! The method to this madness is that they all assess my needs and see things differently. Their skills are also different. One is especially good at removing the downturned line at the corners of my mouth. Another is particularly good at raising my brows and smoothing my forehead with Botox. So multiple opinions can matter.

Seeing multiple doctors in this way also taught me that I am not the only client pursuing a feminine appearance. Many of their trans clients have done far more invasive procedures; some are just discovering how helpful a dermatologist can be.

I am pleased to say that I have great relationships with these doctors and enjoy a very personable and intimate level of service. I love it when they do their magic and stand back and smile broadly! They enjoy helping me achieve my goals and would certainly do the same for you.

Wearing Brahmin.

Actor Richard O'Brien