Tuesday, August 25, 2026

You Should Have Been a Girl

When I was young, I occasionally heard words that were probably intended as teasing, but sounded more like encouragement to me:

“You should have been a girl.”

Perhaps an aunt thought I was too pretty for a boy. Maybe someone admired my long eyelashes or commented that my legs were better shaped than most girls’ legs. At other times, it may have been my quiet voice, gentle disposition or mannerisms that were considered insufficiently masculine.

Whatever prompted the remark, it always caught my attention.

I suspect that many boys who grew up to become crossdressers heard something similar. In those days, children were expected to fit into clearly defined gender roles. Boys were supposed to be rough, loud and interested in sports. Girls were supposed to be pretty, graceful and well-mannered. Any boy who wandered a little too far into the feminine column risked being told that he should have been a girl.

Most boys probably regarded the comment as an insult. Some tried to prove it wrong by becoming more masculine. But for a budding femulator, the words could have a very different effect.

They might feel like a compliment.

A boy already fascinated by dresses, high heels, makeup or the women in his life might quietly wonder whether the adults had noticed something. Did they see the girl he sometimes imagined becoming? Was his femininity showing even when he was dressed as a boy?

Being told that you had pretty eyes or shapely legs could also provide a little hope. Perhaps femininity was not completely beyond your reach. If your face was pretty enough or your legs were good enough, maybe someday you really could look like a girl.

Of course, hearing those words did not make anyone a crossdresser. Plenty of pretty boys with shapely legs and gentle mannerisms grew up with no desire to wear women’s clothing. The remark merely had special meaning for those of us whose feminine interests were already waiting below the surface.

Years later, after we finally slipped into a dress, pulled hosiery over those supposedly shapely legs and applied lipstick to that supposedly pretty face, we may have remembered the old prediction.

“You should have been a girl.”

Perhaps they were not entirely correct. I did not necessarily want to stop being a boy forever. But I certainly wanted the opportunity to find out how convincingly—and how happily—I could become a girl for a while.

Looking back, I sometimes wonder whether the people who said it realized how closely I was listening. What they considered an offhand observation became something I stored away and treasured. During the years when I doubted my ability to look feminine, I could recall that someone once saw femininity in me without my wearing a dress, wig or makeup.

That was encouraging evidence.

And when I finally saw my feminine reflection looking back from the mirror, it seemed that the people who had teased me years earlier had been onto something.

Maybe I should have been a girl.

Or perhaps I was simply fortunate enough to discover that I could enjoy being both.



Source: Rue La La
Wearing Walter Baker


Guymon (Oklahoma) High School
Guymon (Oklahoma) High School womanless beauty pageant contestant (1966)

14 comments:

  1. Interesting post... when I was about 11 and definitely interested in feminine things, my parents had a barbecue and invited some friends and family. One of the women who was the wife of my dad's best man, came over to me and commented that I had legs like a girl. Outwardly, I feigned outrage, "No I don't, " but inside, I was thrilled! And, even today, all dressed up, my wife always comments that my legs are prettier than hers! Yeah, there are times I should have been born a girl!!

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  2. As I grew up,,occasionally would over hear one of Moms friends say,,he would have been such a cute girl..At the time, with occasional urges to explore Moms things,,I was embarassed.. As I grew up,,the urges got stronger, and so did some mannerisms,,and hearing cute girl,,seemed better...Best moment though,,with a good friend leaving work,,she turned to me,,smiled, and said your just one of the girls....Trina

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  3. Now we get into the "why did I start crossdressing" area. I am child #2 (I have an older brother) and I know that my mother wanted a girl. I have no memories of any times she may have treated me like a girl, or attempted to, but I have always wondered - could this be a root cause of my desire to present as female? To quote an old Tootsie Pop commercial, the world may never know.

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    1. When I was really young I heard many times from my mother that I was suppose to be a girl, not that I looked like a girl. At age four or five there really isn't too much difference between what a boy or girl looks like, other than the length of air. Yep, post World War 2 "boomer" family: husband, wife, older brother and younger sister. The first born was the older brother who was named after my mother's father, I came along the following year and my dad's sperm did not produce the desired result" another boy. My brother had the middle name of my grandmother, feminized. I was given the feminine of my grandmother. How novel? Once when I heard I was suppose to be a girl I don one of my mother's nylon nightgowns and cried in her bed that she did not love me because I was not a girl. She held me a promised never to say it again, and she did not. I became the son that got extra discipline and hand-me-down clothes and passed on bicycles, while the older son got everything. She showed her displeasure that I was not a girl. Was this the cause of my crossdressing? Until puberty I had no desires to be a girl. I was rough and tumble; got into trouble at school all the time, etc. However, genetically I never had he body mass of a man. I could never develop muscles past the muscles a woman would have. Did my mother take drugs during my pregnancy?

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  4. I was a nice looking little boy with blondish curly hair and long eyelashes. Sometimes I was told my hair and eyelashes were too pretty for a boy to have and that I sould have been a girl.

    However, at age seven I was forced to dress up as a girl, along with a few other boys, for a summer day camp parent's show. It was humiliating to say the least.

    That set off years of wondering what was wrong with me that I should have been singled out in that way. I was teased relentlessly and notions that maybe I should have been a girl tortured me.

    Eventually, I began to secretly cross dress. I loved it, but for years felt guilt and shame for doing it even though no one knew.

    I'm 72 now and have been married 44 years, and I'm a grandfather. I enjoy my male life, but I've always had this white noise background of what it all means to see a beautifully dressed up woman and wish I was dressed up like her?

    I guess it means nothing more than I like doing that, but still, I wish I hadn't had those questions or statements, or role in the camp show heaped upon me.

    Emily

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  5. Oh,,I think our contestant from Guymon High is enjoying the moment a little too much to be a civilian!!!!!!! Trina

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  6. It was the eyelashes for me also. "Look at those eyslashes - should have been a girl", I remeber vividly. .

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    1. It embarrassed me to be told I could have or should have been a girl.

      I'd never say that to a young boy, ever.

      Emily

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    2. Hi Rhonda, I too have received comments on my eyelashes. Usually envy from women about how long and dark they are. It makes me wonder if perhaps men are supposed to be the ones with luscious lashes and women are emulating us with their mascara and false lashes!

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  7. big family Xmas gathering. don't want the 4 year old 's clothes splattered with gravy etc. At that time women in the kitchen wore a type of apron which may not even exist today. very pretty with lace etc.so we'll put the 4 year old in it.Followed by ridicule from older boy cousins. This is my earliest memory. Did that event jump start my girlish desires?

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  8. My mother said it to me once in passing about being a girl, as the youngest, so I would do womanly things around the house. I remembered it and when I told it to her later, years later, she didn't remember having said it in passing. Many other girls my age and women have told me, in giving a compliment, that my legs were better than theirs. That they can see that I should have been born a woman. I am trans, so I am beyond just enjoying wearing women's clothing.

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  9. When I was a boy, I was graceful, pretty, and had long eyelashes, and of course, had a treble voice. So I was teased for being feminine. And then my voice deepened when I was around 13. That in itself eliminated being teased for being feminine. However, I had a narrow waist and wide hips like a girl. Due to estrogen, I now have a DD bust. Right now I'm going on long walks to fight the Battle of the Bulge, and hopefully get back my narrow waist.
    At choir rehearsals I wear dresses. Some new lady in the choir was wondering where the bass (not baritone) voice was coming from. From me, of course!
    -John

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  10. Guymon is no guy, mon!

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  11. "I did not necessarily want to stop being a boy forever. But I certainly wanted the opportunity to find out how convincingly—and how happily—I could become a girl for a while." This describes my relationship with crossdressing perfectly!!

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