I am not sure of the exact year. You would think that something that significant would be a date, or at least a year I would remember, but I don’t. My best guess is 1962, ’63 or ’64, when I was 11, 12 or 13-years-old… those years when a boy begins transitioning into manhood or otherwise.
I did not dress fully the first time. I only wore my mother’s high heels and nylon stockings (way back when nylons had seams). The second time, I added my mother’s bra and girdle. Then I added dresses from my mother’s and sister’s wardrobes.
After that, I crossdressed whenever I was home alone fine-tuning my presentation, which finally saw the light of day, rather night, on Halloween 1969.
And the rest is her story!
So how old were you the first time you crossdressed?
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| Wearing Venus |
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| Dawn and partner out and about at Falmouth Pride 2024. |
I cannot remember a time when I didn't want to crossdress nor when I didn't think about it.
ReplyDeleteI think as soon as I became aware that boys and girls/women and men were different.
The most obvious difference was clothes.
I am certain was around 5 or 6 years old
I started at 8 years old, 1965. I recall it well. I tried on my mom's dresses, she was a seamstress, that she was making. They were gorgeous and made of silk, taffeta sequins. She made cocktail and evening dresses. I couldn't get over the feel of the material. I also had this overwhelming feeling that I should have been a female. I dressed female at every opportunity. I kept it hidden, still do.
ReplyDeleteI was probably around 11 when I first cross dressed. I remember coming back to school in September and noticing that most of the girls had changed but I hadn’t. My bedroom was downstairs from the rest of my family and right next to our laundry room. I started trying on some of my mother’s and sister’s clothes at night.
ReplyDeleteI was seven the first time I dressed up as a girl. I was at a summer day camp. There was a show for the parents near the end of the summer. My little group of post 1st grade boys were told that we were going to perform in a show, but half of us would need to play girls.
ReplyDeleteNo one volunteered to be a girl and the counselor said that he'd choose the girls. He called out my name first. I felt embarrassed. I did not want to be a girl. I was too humiliated to tell my parents I'd been picked for the part.
I didn't know what to do. I thought of running away, but I was always a good boy who behaved. On the day of the show I, along with about seven other boys, was put into a pink dress, a little bonnet with curls attached to it, Maryjanes, and white tights. A woman put what felt like an incredible amount of make up onto my face. I detested it.
The owner of the day camp offered me a paper cup filled with lemonade. I took a sip and was horrified that my lips left an imprint from my lipstick on it. I didn't want it any longer. Then the man reached under my dress and briefly touched me. I don't know why he stopped nor at age seven did I have any idea why he touched me.
That day was the most embarrassing time of my life.
I've never gotten over it, but when I was twelve, I was home alone and I had the overwhelming desire to put on one of my mother's skirts. I couldn't understand why I had that desire. Wearing mom's skirt lasted about a minute long experience, but after that whenever I was alone I dresses up adding nylons, girdles, bras, and slips underneath my mother's beautiful dresses and skirts.
I felt as though I was a pervert for doing that. I wondered if I was the only boy in the world who wanted to wear girl's clothes. Movies such as "Some Like it Hot" or seeing the three stooges in drag gave me no answers.
More than sixty years have passed since that first time and I've dressed up as a woman countless times. It continues to push my buttons. I'm married and I'm a dad and grandpa. My crossdressing has mostly been in complete secrecy.
Michael
Just about the same age,,11 or 12,, Mom used to hang her hose to dry on the shower rod in my bathroom,,and they were so tempting. Then came raids or her lingerie drawer, girdles mainly, and her closet, her heels,,and lipstick. Wow, well on the road! Trina
ReplyDeleteAbout the same as you, when puberty hit...and like you, the first attempts were "underthings," panties and stockings.
ReplyDeletePretty Sissy Dani
It’s hard to pinpoint a year but I know my sister married when I was 10 years old and I remember my teacher being Mrs. Travato when I did this so I’m pretty sure I was nine years old. I wrote all about that special day right here at Femulate
ReplyDeletePaula G.
http://www.femulate.org/2019/08/caught.html
Hi Stana,
ReplyDeleteMy first experience crossdressing was at a very early age, my mother told me I was about 5 or 6 years old at the time and borrowed a petticoat to make a skirt and a singlet vest as a top - I added some lipstick and a necklace, and wanted to go out to play with my friends ... needless to say that didn’t bode well for me in the early 1960’s, especially with my non-accepting parents ..
The consequential fall out has been something that I have lived with me all my life. But, as you can see from my photo above, I am still here and femulate/dress/be me whenever I have the opportunity.
hugs
Dawn
8 years old. My sister clothes. I very much wanted to be her sister! Lisa P
ReplyDeleteYes, you would think such an important event would be etched in the memory. I also can't remember the exact date, but your timeline sounds familiar. Probably 1969, 70 or 71 - as for my "coming out" it was Halloween 1975. I went into some detail in my blog entry -
ReplyDeletehttps://juliemshaw.blogspot.com/2023/06/down-memory-lane-in-pumps.html
The first time I ever got dressed was probably around age 9ish wearing my mom's pantyhose. The allure of hosiery was so irresistible, even at such a young age, that wearing them was inevitable. I did A LOT of wearing pantyhose in private throughout my teen years, occasionally adding one of mom's slips, but I don't recall ever wearing any of her other clothes. I longed to wear the fashionable outfits of girls my age, not the "old lady" clothes in my mom's closet.
ReplyDeleteOnce I graduated college and got my own place, I had the freedom and privacy to add undergarments, heels, lingerie, skirts, etc etc...and it's been all uphill from there!
My first time was when I was 5 years old. I couldn't resist my grandmother's dressing table, with perfumes, makeup and hairpins... I put on lipstick and put several hairpins in my hair. I tried to take it off before going to bed, but of course my mother and grandmother noticed the next day, but they pretended it was just "childish stuff"... By the way, I love the images you use to illustrate!!! Did you make them on Bing??? Long and detailed prompts???
ReplyDeleteThank you for the kind words, Bete. Yes, I use Bing Image Creator and tweak the images, if necessary, with Photoshop. The longer and more detailed the prompt, the better the results, but even then, the results may not be what I wanted, so I tweak the prompt and try again.
DeleteAbout age 5 or 6 but it turned out years later that I was just dressing as myseif
ReplyDeleteLike others I'm guessing but I'd have to say it was about age 5 or 6. By the time I was in high school, I was dressing head to toe in my sister's lingerie, stockings, dresses and high heels. Right about the same time, I tried makeup too. If attitudes back then had been what they are now, I don't know how different my life would have been.
ReplyDeleteI started at two or three with the whole deal, dresses, shoes, etc., courtesy of my sister, though the will was all mine. I had a rather long shaggy haircut, as some boys had at that time in the 80’s, and was often mistaken for a girl, even in boy clothes which I had to wear out of the house, as my mom dressed me sort of androgynously anyway. Or perhaps I just did not want to wear “manly” boy clothes.
ReplyDeleteAt some point, I stopped openly dressing, but continued in secret, following a slow and steady progression. It felt naughty, but oh so right at the same time. I started buying my own clothes when I moved away from home in my early 20’s, and by late 20’s/early 30’s makeup, wigs, undergarments, etc. entered life, and things took off rapidly from there!
I love that Venus dress in “Femulate Her”! Venus, Spigel, and Metro Style were long my inspirations and places I bought things.
Norah
I also cannot remember an exact date or year, but I was probably 9 or 10. Panties and hose at first, retrieved from the laundry basket, then I would wear clothes and shoes from my sister's and mother's closets. Makeup and hair were not part of my dressing for many years, so I did not venture outside until 2011.
ReplyDeleteSometime around 10 years old I ventured into my mother's underwear drawer for the first time. It was delightful. Soon I was delving into her closet also whenever I got a chance all through my teenage years.
ReplyDeleteI have probably shared all of these gems before.
ReplyDeleteI was about the same age. Probably 12 years old and to the age where my Mom would leave me home alone for the day while she went out on the weekly shopping expedition. The expectation was that I had the basic skills to prepare my own lunch and had shown enough responsibility to be trusted.
I remember trying a bra and nylons but I don't recall ever trying on shoes or heels or even a dress or skirt as a teen. My first skirts were bought when I was in my early thirties. My first dresses came along when I was in my fifties. And I remember buying my first brand new dress at Dress Barn in 2019 and I remember the wonderful experience. I went into the store and the staff was great, they were happy to help me. I was given use of a fitting room and they helped my get the best size for me. I still have the dress and wear it to work.
Another home alone experience I remember is when I first used my sister's nail red polish. The problem I later discovered was that there was no acetone to remove it. The panic was real! I grabbed my pocket knife and scraped away all of the paint before anyone got home.
I remember my first time dressed up, too. I was little, probably no more than 8. I don't remember how old I was when it happened. I wore my Mom's Bolero dance costume from when she was a little girl for Halloween. The three parts I remember from that night were:
1.) My Dad stopping to get gas and my sister telling me to smile and bat my eyes at the pump attendant.
2.) The town's rag shag parade. The little kids would march around the Town's Common and then gather in the school's auditorium to get lots of candy.
3.) After collecting the sugary treats, we went to the house of my Mom's Mom and her husband to trick or treat in their neighborhood. 50+ years later, I'd love to know how badly triggered the husband was by me wearing my Mom's clothes. He was a genuinely evil creep.
On other notes, October 11 is:
My 59th birthday!
I'm getting my flu shot and the latest COVID booster today.
International Coming Out Day.
This weekend is the Pride celebration in Las Vegas with the Pride Parade happening tonight.
This weekend also has the 30th annual Age of Chivalry Renaissance Fair in Las Vegas.
Yes, going to all of these things means I will be a very busy gurl!
Have a great day.
Heather.
My mom found my stash of some old hose when I was in the second grade. It was before then. My first time probably was me trying on some of mom's pantyhose that were in the bathroom where she would hand-wash them and dry them.
ReplyDeleteBefore that, I recall putting my sister's Barbie's panties on my big toe once and feeling something good. (Weird, I know...)
Before that, I remember putting on my mom's house shoes and putting some curlers in my hair. I came into the kitchen and she saw me and laughed and said, "Do you want to be a girl?" That was not crossdressing. That was just a kid playing. It held no special place for me. I might have been 4 when that happened. I do remember thinking about her question. The only time I can think of that I actually wished I was a girl was later, when I thought, "If I were a girl, then I could wear these clothes."
The first time I ever crossdressed in front of my mom was when I was out of college. A friend asked me to dress up for an event he was hosting. Mom helped me with my costume. That was such an excellent experience. She was letting me try on things, and I was dressed in front of her. There was no fear on either of our parts. I guess that is also the last time I have dressed around her.
Joey
Years later, some dresses got put into my closet. I think they were my sister's. That was handy.
As a child I don't remember wearing dresses as I had two brothers and no sisters. However my mother taught me how to apply lipstick and my paternal grandmother taught me how to apply nail polish. When I was about 6, I converted a pair of shorts into a skirt by cutting the crotch area. Needless to say, my mother was not pleased.
ReplyDeleteI started to wear dresses around 2010, and I still presented in drab most of the time. Now I hardly ever present in boy mode anymore, as my default mode is en femme.
John
I was four — I remember it specifically as I had not started school yet. Unfortunately I did not have the luxury of a sister and her wardrobe so it involved oversized clothes “borrowed” from my mum! I had also fallen into the gravity well of shop catalogues and spent hours looking over the clothes, especially the lingerie and being fascinated by the girdles and corselettes in particular. Today I wear those corselettes underneath my skirts and dresses whenever I go out, a childhood wish come true.
ReplyDeleteI must have blossomed early, because after I expressed an interest, my mom would sometimes let me wear her lipstick and nail polish starting around 3 years of age. By the time I was 5, I was totally obsessed with high heels, although I had almost no access to shoes that fit at that time. (Mom was a size 6-1/2 US, and it felt like her shoes went from "too large" to "too small" on my growing feet almost overnight.) I was regularly in her closet and lingerie drawer from that time on, when I could get a few minutes alone at home. Her girdles and stockings were my favorites. I got my ears pierced at age 9 (a long story in itself) and went shopping for heels at a downtown department store with my mother when I was 12. I'm 67 now and never slowed down.
ReplyDeleteGuess I was always a bit of a mummies boy, hiding behind apron strings, however when I read about April Ashley in the newspaper, something clicked. Then of course the part in J.D. Salinger’s book, Catcher in the Rye, which was part of our curriculum, when he was in the hotel room looking across to another hotel room, made me realise that I wasn’t alone.
ReplyDeleteThat passage in Catcher in the Rye caught my attention in High School. I felt the author was describing me putting on one of my mother's evening dresses. When I read that I realized others did it too, but honestly it sounded so damn creepy. It magnified the secrecy, shame, and embarrassment that was in my mind. I still remain pretty closeted and I don't want to share this with my family and friends, but I've worked hard at trying to remove the shame and embarrassment from my mind.
DeleteEmily
around age 18 on a Halloween double date.went well until someone I knew came in to the nightclub and my guilt took over and we spit early.
ReplyDeletethis happening was due to my dropping enough hints to my friends (boy / girl role reversal). what stimulated this was an article in the paper about 7 weeks earlier--a young lad attended the first day of school at a Catholic girl's high school. he was totally decked out in the school uniform and was there until about noon when the word got back to the nuns and he rapidly departed
Emily