Wednesday, July 11, 2018

Do you remember the first time?

By Starla Renee Trimm

Do you remember the first time you crossdressed? The first time you furtively slipped on some nylons or a dress or a bra or heels?

Oddly enough, I don't.

I feel like I must be the odd gurl out on this. Countless others over the years have described that first time to me. But I think and think and rummage through the cobwebbed corners of my brain and I got nothin'.

I grew up in New Jersey and my family moved to Florida in 1970 when I was 12. And honestly, I cannot recall a single instance of crossdressing before we made the move.

Thought about it, sure. Browsed the Sears catalog looking at the pictures of smartly-attired lady models and wondered what it was like to dress like that, certainly. Watched stylish actresses on TV and fantasized about wearing that dress or having that hairdo, yes… and often.

But I cannot recall ever actually putting on an article of female clothing until we moved to the Sunshine State. Even then, the memory banks are murky. I know that by the time we had been there for several months, I was regularly "borrowing" my mother's things. (And ashamed to admit, shoplifting wigs to wear – a nasty habit that I regret with shame to this day, yet I am also quite glad I was never caught.)

But I have no recollection of when, why and how I first slipped on her nightie or tried on her bras. Not any memory of anything that might have triggered the shift from fantasizing to femulating. Was it something I read or saw on TV? Or maybe just the fact that I was now old enough to be trusted to spend a few hours home alone giving me a relatively safe window to experiment? I have no idea.

The mind can play tricks on us in regards to memories. Things can be erased from conscious memory due to trauma and false memories can seem very real.

An example of the latter that has nothing to do with crossdressing. I still harbor a vivid memory of reading a magazine article about the Kent State shootings while laying on my bed at my grandparents' cottage in Vermont where I spent my summers growing up. But we never returned to Vermont after the move to Florida in the Spring of 1970 and the Kent State tragedy occurred in May of that year. In fact, 1969 was the last summer we spent in Vermont. Yet I have the strong, legitimate memory of watching the first moon landing that July on my grandmother's ancient DuMont black-and-white television complete with the dead fly permanently stuck between the picture tube and its protective cover.

So, it is impossible for me to have been reading about Kent State in Vermont. As much as my intellect accepts that reality, the false memory persists to this day.

As for trauma and lost memories, maybe I did crossdress in New Jersey and was caught. And the experience was traumatic enough for my brain to hit the erase button.

I don't think so. Because I do remember the first time I was caught in Florida and it was very traumatic. But I still have the memory.

So anyway, how about you? Do you remember your first time? Or are your early memories of femulating lost to the ages like a wiped videotape? Are there more of the former or latter among us?

I'll let y'all figure it out. Right now, thinking about all this, my head hurts.

Source: Rent the Runway
Wearing Trina Turk (Source: Rent the Runway)

Jannik Schümann
Jannik Schümann femulated in the 2015 German film Mein Sohn Helen (My Son Helen).


  1. AnonymousJuly 11, 2018

    Do you remember the first-time you had sex as a woman with a man?

    1. Do you remember the first time you had sex as a woman with a man crossdressed as a woman?

    2. Do you remember the first time you had sex as a man with a man crossdressed as a woman?

    3. AnonymousJuly 12, 2018

      I do remember making love as a woman with a woman. Lovely tingles everywhere

    4. The first time I had sex with a man I was @ a 1920's themed fancy dress party. I was 18,we danced most of the night,he knew I was a crossdresser,he was 23.he drove me home (staying over @ my sisters,) invited him in for coffee! He stayed the night,we were in a relationship for was wonderful, thankfully it didn't put me off relationships with both sexes. The best of both worlds. �� Charlotte.xx

  2. Dear Stana,

    The entire film MY SON HELEN is on YouTube. It’s in German.



  3. AnonymousJuly 11, 2018

    All I remember was that I was around 12 years old and anytime my parents went out for any length of time I would spend my time in my mothers closet and drawers. Panties, nightgowns piegnoirs were choice of dress especially any thing Chiffon.Now having transitioned as a full time female I no longer have to sneak around. And my love of those wonderful soft articles of clothing now fill my closet and yeas I 2 chiffon nightgowns that I sit around my home feeling like the lady I am.

    1. Hello!almost the same story,my first item was a creamcolor halfslip with a broad white lace hem,i tried on and since that day(i was 4-5years old i am hooked on lingerie skirts dresses etc i am so happy when i can femulate a few days��������

  4. Full Slip & Seamed Nylons As a 3yr old 1949 NYC

  5. AnonymousJuly 11, 2018

    I guess I remember three different first times I crossdressed. The first time was when I was in 5th grade (child of the 80s), and I remember looking through my mom's closet, and trying on her dresses, and wishing someday that those would be mine, and then buried it in the shame of thinking what I was doing was wrong. The second time I did it was in college, under the guise of halloween, and I went as a "sorority girl", really again wishing those items were mine. And the third first time was after my wife and I got married, and started having struggles a year into our marriage, and I started wearing her items. I still do wear her items, and have bought my own as well, but have never told her. Her mental state can't handle the idea of me doing this for halloween much less as much as I want to, so I live in the closet regrettably, waiting for that day I can do so much more.

  6. AnonymousJuly 11, 2018

    Hey! I had a long reply to the "do you remember" story but it would not post. Too long I suppose. How do I do that?

  7. Sometimes, I wish I had never crossdressed. I would love to experience getting dressed makeup and wig to heels for the very first time.

  8. I must have been about 9. Suddenly, I was old enough to be left alone in the house so I went exploring and found a rag bag of my mother’s old clothes stuffed away in the bottom of the wardrobe. In spite of a heightened sense of danger, I tried on a pair of old stockings and an old girdle. They felt wonderful!

    I do not have an earlier memory but I already knew, somehow, that what I was doing was forbidden but the attraction was too strong to resist. I have managed to bury it for long periods of time but it always comes back. I am now fedup with resisting as the emotional cost is too high and am now considering my nextvsteps.

  9. AnonymousJuly 11, 2018

    To Starla, If you cannot remember but want to remember, do a google of EMDR. Eye Movement Desensitization and Reprocessing. You dont need the services of a therapist, just follow the basics given in many references to EMDR. This technique was discovered by a female therapist while she was walking on a beach. She was searching her memory for a reason for the cause of her emotional distress. Often when one searches memory, the eyes scan left-right in a rhythmical fashion. In the course of the search, the connection appeared (as connection of image and thought and feeling) in her mind. Problem solved. I have experienced EMDR, both in therapy, and searching my mind on my own. Both seem to work. So go cheap and explore on your own. Since you wrote of your c-d adventures, if you do discover something significant, perhaps you will share. Velma Dinkley

  10. AnonymousJuly 12, 2018

    I can remember the first time I tried a skirt on
    It felt strange putting both legs in the same place
    Getting into a dress with a long back zip was very different to what I had been used to with trousers
    Pulling the zip up was a challenge
    I found both the skirt and dress very comfortable once I got used to the openess down below

  11. Julie M ShawJuly 12, 2018

    I am one of the "I Don't Recall The First Time" gals. I know I started with Mom's things, and when my little sister grew up enough I went between the 2 closets. I remember my first time going out - late at night for a walk around the block, and about half way a police car pulled up beside me and he asked, "Is everything alright, Ma'am?". Scared me to death, I was shaking all the way home. I remember the first time I presented dressed - Halloween in 1975. But as to the actual, very first ever time to put on feminine clothing - lost in the memory banks.

  12. To my first was only stockings, dresses and makeup came later, here the link to ‘my first time’

  13. Really had to go back and try to truly recall the first time. What I recall is around when I was 10 years old or so I really was fascinated in girls/women's clothes, I was really intrigued with them always wondering what it would be like to wear them. My parents had a fairly large walk in closet, of course it was mostly Mom's things, that I could lose my self in and just wonder away. For what ever reason I never got the courage to try anything on. One day Mom and I and I were home alone and somehow I asked her what is was like to wear a dress. I don't remember the actual conversation on how we got to the point where she said go try one on. Then I really did not know what to do, so she went back to the closet and got one the would "work." It was a light blue shirt waist dress which was the type dress she usually wore. Wearing it felt very different, I walked around the house just trying take in the feeling of wearing a dress... looking out the window, sitting down, even laying down with it on. Really not sure what all was running through my mind.

    After some time had passed, have no idea how long it was, but it all took place in the afternoon. I returned to the part of the house where she was sitting and asked her what do you think Dad will say? Thinking he might be amused and get possibly a laugh out of seeing me in a dress... she calmly said "I don't think he will care for it very much." That was not at all the answer I thought I would hear. I stayed dressed for a little while longer thinking about her response and I suppose not wanting to create any negative vibes and not have Dad be disappointed with me, I took the dress off. Nothing was ever agin said to me by my Mom about wearing a dress and I have no idea if she ever told my father. I guessed I sensed a barrier that I chose not to cross for some time.

    While I never experimented with any female clothes from that moment until the time I was about 17, my curiosity was still just as strong as ever. Then at 17 I tried on my girlfriend's side zipping shorts that she had left in the car after a trip to the beach. Not long after that it was a pair of nylons. Those brief encounters were all that was needed for me to know I wanted to try being dressed totally female. From then on it was just a lot of incrementalism with many periods of guilt and suppression of those feelings in between.

    Have to say there is so much I would have done differently and SOONER if I knew then, what I know now.


  14. AnonymousJuly 18, 2018

    I was 10. Curious to see what my legs looked like in my Mum's tights. Then moved on to bras,stockings and dresses. Looking back,she must have known what I was up to but never said a word. Years later I did muster up the courage to ask her to borrow one of her outfits for Halloween.Surprisingly she agreed quite readily.

  15. At age 5-6 i tried on mom'half slip(vaserette hollywood)while she was standing beside me,it felt so right/good later she laid her dresses&skirts where i had easily acces to them-she liked my feminime side-

    1. I read your post and was so jealous... but then I remember also having a similar experience when I was much older that involved an elderly in-law. It was so kind of her to 'know' and yet not to say a word. I wish I could have been totally open and yet there was a sweetness to us both acknowledging the situation. I loved that she allowed me to share that side of me with her. And she in turn shared truths with me.

  16. My earliest fantasies was being enslaved by a society of women and being forced to become one at age 6. I looked through the catalogues and Sunday adverts of the women's section. And while I might have worn something briefly it wasn't until I was staying for a long vacation at my grandmothers at age 13. I discovered her special nighty and panties and I wore them to bed for a week. Decades later I still look back and smile, and I underdress when possible.

  17. My first time was when my mom wanted me to be a princess for Halloween wearing a lacy white dress, white gloves and shoulder length dark wig for Halloween. I modeled it for her in her bedroom but she could tell I was too nervous to go out in public. So she made me a skeleton costume to wear instead. But that sparked something in me because after that I secretly would put on her dresses (she kept in the closet in my bedroom!) plus the same wig every so often for years afterwards.