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?