Saturday, July 15, 2023

First Time

“How old were you when you first dressed up?” was a question asked on Reddit r/crossdressing last week. There were about 200 comments in response. My guess was that the age of puberty would be the most common answer, but a lot of ladies admit to crossdressing earlier than puberty.

In my case, I did not wear woman’s clothing (nylon stockings and high heels) until I was 12 or 13 years old. However, I do recall a few episodes when I was younger (single digit-years-old) when I wrapped a bedsheet around me to simulate a woman’s evening gown. 

And then there was the time that I smeared my face with cold cream to simulate a circus clown’s white makeup and my mother misinterpreting my feeble makeup skills as attempting to simulate a female’s face – then proceeding to remove the cold cream and make up my face as a proper young lady. 

So, how old were you when you first dressed up?

Source: Bebe
Wearing Bebe

Tim and Tina
Tim and Tina
I welcome all Femulate readers to submit Before and After photos for publication here.
Just send your photos to stana-stana at-sign


  1. Davina SatinaJuly 15, 2023

    My earliest memories of dressing up, or at least thinking about it and wanting to, were from primary school days. I was probably 5 or 6.
    Basically, I would try on any feminine item I saw if there was no one around.
    I remember taking a lipstick from the living room mantel piece and running into the garden to hide in a shrubbery. Blindly applying it as I sat under the safety of the branches!
    I often closed myself in the bathroom and raid the laundry basket for my mother's and sisters' pretty dresses, skirts and blouses.

  2. AnonymousJuly 15, 2023

    Aunty here. I raided my mom's bra drawer secretly when I was 14 during times I was alone in the house, and though she suspected me she never punished me. When I was 16 my folks went away for the weekend, and I was alone. My mom had a nice blue one-piece 50's swimsuit with padded cups--had to have a bath wearing it.

  3. AnonymousJuly 15, 2023

    I was 7 or 8 when my older sister made me try on her dance uniform; leotard, tights, leg warmers. I guess that was when I caught the cross-dressing fever. I've been doing it ever since.

  4. AnonymousJuly 15, 2023

    The first time I ever dressed up as a girl was when I was 7. It was 1961 and I was attending a summer day camp. For some reason that I'll never understand the people in charge decided that for the parents day show several of the boys in my group would be dressed up as girls to sing a love song to the audience.

    I was told I'd be one of the "girls." I didn't want to do it, but being seven I did not know how to get out of it. I dreaded it. When the boys, myself included, were dressed up and after our make up was applied, we were told to sit and wait.

    A counselor came up to me and reach under my dresses' skirt and grabbed my crotch. Startled I jumped back. He told me to be a good girl, but he backed off and did not touch me again.

    Being seven I thought he'd groped me to humiliate me for wearing a dress. I did not know about sexual molestation, but I thank God that all he did was grab me and one time.

    I was teased by friends for dressing up as a girl that day. I didn't like it and was angry I'd been forced to be a girl. However, over time I began to have urges to wear a dress again. Once I saw a boy dressed up as a girl for Halloween and I realized that I was jealous of him.

    When I was 12 and left home alone I dared to try on a chiffon dress of my mother's along with one of her girdles, nylons, and a slip. I couldn't believe how wonderful it felt, but also I felt ashamed as if I'd done something perverted.

    Eventually, as we all have realized, I discovered that other boys liked to dress up as girls. Finally at some point in my adult life I quit beating myself up for wearing women's clothes and accepted it. I've only been out in public a couple of times. Most of my Femulation is in private.

    I have a wonderful wife who wishes I didn't have this urge, but we have a "don't ask don't tell," policy. Maybe I wish I didn't have it too.

    That's my story.

  5. AnonymousJuly 15, 2023

    My first time was at 4 years old in Connecticut when I naturally slipped into mom's pantyhose and high heels just being my .𝐻𝑒𝓇-𝒮𝑒𝓁𝒻 .

  6. I truly envy those who have a vivid memory of their first experiences with crossdressing. I honestly have no idea when I started -- it's been a part of my life for as far back as I can remember. I'd set an alarm for 4:00AM on Saturdays (the clock under my pillow, since I shared a bedroom with my 2 brothers) and sneak up into the attic to try on Mom's things, mostly evening gowns circa late 1950's.
    I do remember my first time venturing out fully dressed - I must have been about 16 and took a very late night walk around the block. I kept extending the route, 2 blocks then 3, until I turned a corner and a police car was approaching from the opposite direction. He stopped and asked, "Is everything alright, Ma'am?" I said a feeble, "I'm fine" and kept on walking. I don't remember the rest of the walk!

    1. AnonymousJuly 16, 2023

      Julie, I'm the girl who wrote about my 1st time summer day camp experience. It's not a good memory. When I finally started crossdressing as a middle schooler, while it was extremely pleasurable, I felt guilty for doing it and wondered why I had a perversion such as that. I felt as if something was wrong inside me and that I'd been chosen to play a girl in the show because that man at camp who touched me inappropriately knew something about me that I didn't know.

      Often I've thought that my attraction to femininity is based upon the discomfort I felt as a young male. I was not a big kid and while people would have described me as "all boy," I wasn't athletic nor a bully. I had this perhaps false feeling that girls had it easier because they were nice and got to wear pretty clothes.

      Sometimes I believed that my life would have been easier, fun, and more rewarding if I'd simply been born a girl. Sometimes I'd have dreams in which my girl cousins were outside my house waiting for me to come play with them and in the dream I'd meekly emerge wearing a dress and my cousins smiled and accepted me as one of the girls. That was before I was 12 and put on mom's chiffon dress for the very first experience of voluntarily crossdressing.

      When I was older I realized that being a girl, and then a woman, wasn't simply a world of pretty dresses, shopping, and sisterly camaraderie.

      This has been a lifelong tug of war, but I try to live with it and don't want to hurt family over it.

  7. AnonymousJuly 15, 2023

    I was about 5 when I first tried on my sister's bathing suit. By the time I hit high school I had advanced to dresses, heels, stockings and makeup. And on and on.... Lauren

    1. AnonymousJuly 16, 2023

      My first time was my sister's bathing suit too. It was hanging in the bathroom and I was seven. It was a red, white, and blue, one piece with a little pleated skirt and I don't know why, but I wanted to try it on. Later I began to try on her party dresses and later I graduated to wearing her pantyhose, slips, skirts, bras, and blouses. I was never caught though there were a couple of close calls.

      In college a girl I was dating asked me if I wanted to be a girl for Halloween. She said that her sister had done that to her boyfriend and it would be fun for us to do it too.

      I trembled so much when she asked I thought she might notice and I excused myself to go to the bathroom where I debated with myself whether or not to accept her offer. Finally, I decided that if I did she'd see through my "good sport" attitude and realize I loved crossdressing.

      Alas, I passed up the chance that Halloween and I've never publicly dressed up. It's always been in private.

  8. For me it was Puberty at around 13. I don't know what compelled me to put on that first skirt. Maybe curiosity? Just to see how it felt. It was a cotton green calf length skirt. I put it on and got this huge sense of euphoria. I loved how it draped and flowed. I also paired it with a half-slip to imitate what my mom would do. Everything felt so soft and flowwy. It just made my so happy. I don't know why. But from that day forward I CDed any chance I got in secret and daydreamed about wearing women's outfits. These thoughts and urges on a daily bases never stopped for decades. I was in self denial and only came out to myself as a (non-transitioning) Transgender at 47.

  9. AnonymousJuly 15, 2023

    I do not know when the first time I tried on some of my sisters' things from the dirty clothes in the bathroom. I do remember getting caught trying to sneak my mother girdle back into her bedroom at around seven.

  10. Diane SmithJuly 16, 2023

    I remember being fascinated by my mom's lipstick and nail polish at about age 2-1/2. She was fairly open to that and let me wear them sometimes. I don't know at exactly what age I first tried on her clothes, but by age five I was making regular visits to her shoe closet and lingerie drawer. Although I was strongly drawn to trying on her things, those adventures were not very successful because everything was much too big to fit me at that time. I was never caught or punished for it, but I figure Mom had to know because no five year old could have been careful enough to put everything back neatly without leaving a trace. And I was an only child, so there was no one else to blame!

  11. I was four when I was borrowing my mum’s underthings. I also used to cut the lingerie pictures out from store catalogues and dream about wearing them (oh those girdles and corselets!)

  12. An outlier here. I *wanted* to dress as far back as I can remember - well, as far back as I noticed that boys and girls were dressed differently (which may be the same thing now as I think on it): so, about 4 or 5? I can't recall with any accuracy much of anything before then. However, I did not actually dress in anything other than male clothes until I was 18 and at University - and that was just an item of underwear I was sent in a convoluted prank, in private and alone. For anything more, I'd have to wait until I was 23 and bought a pack of knickers. Then, the following year a friend of mine convinced me to wear a dress he'd bought for an occasion, we'd later date and I'd actually dress up properly for the first time at his birthday party. I *did* use string to alter some white undies I owned to make them more 'knicker-like' around the age of 13-14 though. I finally accepted myself as transgender at the young age (!) of 40 and went 'full-time', so to speak, the following year.

    tl;dr - I dressed properly for the first time aged 24. *Ralph Wiggum voice:* I'm an outlier.

  13. I was probably around 7 or 8. I got up early for some reason and tried on the pair of nylon stockings hung up to dry in the bathroom. I put them and took them off several times. I had always wanted to as far as I could remember and when the opportunity presented itself, I couldn't resist. Over sixty years ag and I've nerer looked back!

  14. For me it was 7 grade. I know for sure because for seventh grade initiation at the parochial school we had to dress up wearing a skort, a white shirt backwards (It looked liked a Peter Pan collar), and one high heel (When you crossed your legs you could see the high heel shoe).

  15. AnonymousJuly 16, 2023

    I was nine years old I sneaked down to my sisters closet, with this over whelming need to wear fishnet stockings and a mini skirt that I had been watching girls in school wear.

    I wrote all about it in this really cool blog called Femulate. Paula G

  16. AnonymousJuly 16, 2023

    My earliest recollection was putting on one of my sister’s full slips. We all know how sketchy memory can be, but I would guess around the age of 5,

  17. AnonymousJuly 16, 2023

    Perhaps around the age of five, I recall slipping into one of my older sister’s full slips. -Kim

  18. AnonymousJuly 16, 2023

    I do not recall the age I was when I developed a fascination for my mother's nylon full slips. She hanged the laundry to dry on a clothesline that ran the length of the hallway to the bedrooms in our apartment. At first I would just fondle the silky material, and, later progressed to taking them down and slipping into the slips in the bathroom. It wasn't until puberty that my interests expanded into her bras, girdles and stockings to go with the slips.

  19. AnonymousJuly 16, 2023

    Like all of us I wore my mom's/sisters clothes shoes when I was about six or seven. And from then on only an article or two. Only when I turned 35 did I get dressed completely from head to toe, wig, makeup, b forms, hip pads ,dress, hose, heels, etc. After that I knew there was no going back! Haha. Allison,

  20. When I was a little kid, Barbie wore underwear. I remember slipping my sister's Barbie's underwear onto my big toe. I remember feeling something. I guess it was a yearning. I would pet my blanket's rayon edging because it was silky. I loved silky fabrics. Eventually, I tried on a slip and later pantyhose. On and on over the years until I tried on my mom's dress and heels. I own my own dresses and shoes these days, but I seldom get to wear them.

  21. I embrace my new life at 12

  22. AnonymousJuly 17, 2023

    On a different topic.....I love the Bebe dress!!! Lauren

  23. Melissa RobertsJuly 19, 2023

    I remember that I was about 5 or 6 years old and was staying with my Aunt. One day I was in the bathroom and she had a wooden drying rack set up with bras and panties hanging to dry. Not sure why I did it but I got undressed, put on a pair of her panties, got dressed again and went about the day. I had kind of forgot about that I was wearing them until it was time to go to bed and change into my pajamas. They were light blue nylon granny panties with a lace applique. I Love that style panty until this day!

  24. AnonymousJuly 29, 2023

    I started around age 8. I used to see mom getting ready in the morning for work and i'd catch glimpses of her putting on her makeup and in her shiny underwear. I wondered how that felt, and tried on her panties. I guess that hooked me and here I am today.

    Michelle Madison