Monday, April 4, 2016

My First Time: Stana in Wonderland

This is the first installment of a new Femulate series in which I invite readers to share their first crossdressing experience. Try to recall that moment the first time you tried on a woman’s garment and began the process of unveiling and exploring your feminine self. 

To entice you to share your first time story, I will give away a free copy of my e-book Fantasia Fair Diaries to all whose stories I use in Femulate.

To kick off My First Time, I will tell you my own story.

My Self-Portrait
I was a renaissance boy.

Growing up, I was interested in many things and some of those things resided on the feminine side of the street called “Life.” My parents did not dissuade me from my feminine interests and my sister accepted my interests because it gave her an in-house feminine playmate.

So I thought that playing house was just as “normal” as playing baseball. And even though some of my peers let me know that I might be a “fairy” because of my feminine proclivities, I ignored them and happily skipped on board the Good Ship Lollipop.

And so it went until one day at the age of 12, I was home alone and heard a voice calling me. The voice was emanating from my parent’s bedroom. More specifically, the voice came from the drawer of my mother’s bureau that contained her intimates.

I felt like Alice in Wonderland as I opened the bureau drawer and my mother’s nylon s beckoned, “Try me!”

I carefully removed a pair of my mother’s nylons from the drawer and rolled each one up my prepubescent hairless legs just as I had seen my mother do so many times in the past. But something was missing.

When my mother put on her nylons, she finished by attaching each nylon to the garters of her panty girdle. My briefs did not have garters, so the nylons were loose on my thighs and slipping to my knees. I needed a girdle. Conveniently, my mother stored her girdles in the same drawer as her nylons, so I borrowed one from my mother’s stash and squeezed my chubby figure into it.

As I carefully attached my nylons to the garters of my girdle, I was impressed on how well the girdle shaped a chubby boy into a feminine figure. But something was missing.

Although I now had a nice figure from the waist down, my girdle pushed some of my body fat up over the top of the girdle joining up with my boy boobs to create an unsightly muffin top. This will never do, so I revisited my mother’s bureau and found the perfect solution: a long line bra. After I slipped on the bra, everything seemed to be in place and I opened my mother’s closet to look at myself in the full-length mirror hanging on the inside of the closet door.

Wow! I was impressed with the female figure that I saw in mirror. I thought I looked a lot like those women I saw in the Playtex and Maidenform advertisements!

As I admired the girl I saw in the mirror, I noticed the stacks of shoeboxes stored in the back of my mother’s closet. I did not hesitate as that voice urged me to go for it. So I searched through the shoeboxes and retrieved a pair of high heel pumps that I quickly slipped on and then revisited my reflection in the mirror.

Wow again! Not only did I have a figure that rivaled a shapely female, but now my legs were as shapely as any female’s!

After admiring myself for a few minutes, I decided that I better disrobe before someone came home. So I carefully removed all my mother’s finery and returned them to their proper place. But my Pandora had escaped and I would often return to my mother’s wardrobe to adorn myself as the girl I discovered in my soul.

Source: Boston Proper
Wearing Boston Proper.

David Castiblanco
David Castiblanco


  1. To state the obvious: thank you for sharing!

    That's a powerful tale you have there and a powerful set of emotions guiding it. All respect to you!


  2. It seems so many of us older girls shared the same type of experiences. Although I didn't have any sisters, I had somehow acquired a miniature china tea set with a little doll, which I treasured. Not exactly boy's toys. Of course, finally trying on Mom's nylons and girdle, don't remember the bra, but definitely a slip, when I was 11, and thought I looked like the girls in the Sear's catalog. My Mother must have realized I was into her things, but never brought it up to me, probably didn't know how to address it. She was born here, but attended school run by Polish nun's until 8th grade, so something like this was no doubt beyond her comprehension. I do remember her saying when I was much younger that she wished I had been a girl, not another boy, but somewhat wistfully. I am older then you, Stana, but how these memories stay with us.

    1. More than once, my mother pointed out my feminine features to me and said I should have been a girl.

  3. Julie M ShawApril 06, 2016

    I don't immediately recall my first experience, it feels like it's always been a part of me. But now I will try to recall a first time. Thanks for sharing, and for the challenge!

  4. Oooh, how I relate to the story you shared. For me, though, there were many visits to that bureau drawer in Mom's room that contained the feminine things when I simply looked and touched before I ever tried on. Once I tried on my first set of underthings I forever thereafter wanted to be a girl. Nancy

  5. Me pusieron una faja panty en 1972 con 12 años por no caberme un traje confeccionado para una boda sun siendo chico.Fue una idea de una vecina ante la desesperacion de mi madre por haberme engordado.