Friday, September 1, 2023

Tomboys and Sissies

By Paula Gaikowski

Society often judges men who show feminine qualities unfairly. This happens because our culture values masculine traits more than feminine ones. 

I’ve been crossdressing since I was 8-years-old. When I think back to those afterschool dress up parties when my parents were at work, I realize now how often I spent time dressed up as a girl. I did it constantly. Several days a week, all though elementary and high school. I was bound to slip up (pun intended) and be discovered. My mother must of known someone was in her things; perhaps she just decided not to say anything. 

I suppose I became a bit too comfortable and left her no choice. One day I left her clothes, lingerie and a wig scattered all over her bedroom. I had complexly forgotten to cover my tracks and was called up to her room and asked to explain what was going on. 

I was mortified and told her that “I was just messing around.” That’s all I could think of. I remember her horrified look and the word “sissy.” Do you want to grow up and be some kind of “sissy.” Her words and demeanor hit hard. 

I did want to grow up and be a woman or at least dress and live as one. But now the message was clear that was bad, extremely bad. I was made to believe that I had a character flaw.  

People treat men and women differently when they act in ways that aren't expected for their gender. Men who act in feminine ways are made fun of and given mean names like “sissy” or “effeminate.” This is hurtful and makes men hide who they are to fit in.

On the other hand, women who do things seen as masculine are often praised. Girls who like things considered boyish are called “tomboys” and are admired for being confident. This  shows that our society thinks being feminine is not as good as being masculine.

The reason for this unfair treatment comes from the way our society is set up. We have a history of thinking that being tough, loud and strong is better than being gentle, quiet and caring. This way of thinking makes us believe that men showing feminine traits are weak and not as important.

To change this, we need to teach people about how these ideas hurt everyone. We should show that both masculine and feminine traits are okay for anyone, no matter their gender. We can also celebrate people who don't follow the usual rules and act the way they want.

Had my mother reacted in a more positive way, perhaps my life would not have been the struggle it has been concerning my gender identity. Had she told me not to be ashamed and that it’s okay to dress up like a girl if I want to, then I could have approached this conundrum with hope and optimism instead of self-doubt and anxiety. In her heart, she was trying to protect me and save me from a cruel society that needs to change its perception of femininity and masculinity.

Source: Ann Taylor
Wearing Ann Taylor

Femulating in London


  1. "...we need to teach people about how these ideas hurt everyone."

    Very much so, yes. IMO, a woman should not be compelled to be pretty, thin, youthful, quiet, etc; but should be free to behave and present at they are comfortable. Likewise, I think men accepting this and softer traits in other guys would be a good thing. Hopefully people would be able to be themselves and not carry around a mask (with the emotional heavy lifting attached). That may help reduce stress and mental health issues.

    I'm pretty tired of the toxic macho BS and how that's hurting those outside that boys club.

  2. Spot on Stana! I was also 'caught' in my sister's clothes and told exactly what society (at that time - late 1960's) - would think of that. Hopefully, things are changing for the better now.

  3. Here is a comment from Julie that got deleted in error by the moderator of this blog: Thank you for this post, Paula and Stana. A topic that needs to be addressed more.
    I post a daily meme on my FB page -- the "I Love Dressing" Meme Of The Day -- and the one I have received the most comments on says "Crossdressing IsThe Male Version Of Tomboys". We need a male version of the word tomboy other than "sissy". (One of my readers suggested "Juliegirl", and my humility prevented me from embracing it.) (lol)

    1. Femboy seems to be the positive term evolving amongst millennials

  4. Interesting info on the term Nancy boy which is derogatory

  5. My desire or need to wear female clothing did not arise until puberty. Yes, I did try on my mother's nylon full slips on occasion because I loved the feel of the nylon. I had no desire to be a girl or to have been born a girl. My parents were homophobic and, when wearing my mother's kicked in they tried to catch me in the act. As to "Tomboys" the numerous boys in the neighborhood banded together every day to play baseball. On day "Charlie" showed up as she wanted to be called; not her given name, Linda. She appeared in jeans and tee shirt and sneakers, short hair, and carried her baseball glove. We needed a center fielder. All we asked her was if she the "goods." She could catch, hit and run. She played with the skills and was equal to many of the boys and was superior to some. With hindsight it was evident her parents had to have supported her. I often wonder what became of "Charlie." She'd be in the middle 70's now.

  6. Growing up with my formative years in the 1980s, being called a "sissy" was the absolute worst thing for a young boy. All you could do is hope to hide one's desire to crossdress and hope to god no one found out. And then deal with the shame and guilt. For most of my teenage years I never even smiled for fear people would "see through me."

  7. With all the talk of how being masculine is superior to be feminine, consider if you had to choose only one gender to exist, it would have to be females. It would be possible for a specie to procreate with just females. However, the genetic makeup of the offspring would be identical to the mother. So, there are males to ensure the survival of the specie to provide for genetic diversity.


  8. When I grew up in the 60s SISSY WAS the worst thing you could call a boy. Some
    times for playing with the girls. other times as a dare. Fist fights would
    occasionally follow. Yet today I see it in ebay when sellers (i presume women)
    callout to CDs & Trans to come buy my items. Its still a Bothersome wotd to me! linda B

  9. Having grown up in the 70's and 80's and lived through all of the worst parts of existence, being a dopey middle school kid, geeky junior high kid, dorky high school kid. Is that a kid who was in the band? All of the memories come flooding back. Yes, sissy was bad but there were worse words too. Far too many homophobic slurs were used back in junior high. the jerks would add the evil words to your last name for the most evil and stinging insult. And yes, it truly was the worst thing when it was used.

    The younger generation has reclaimed the word "queer" and turned it around from a word that was one of the worst insults, it then became a word that was NOT to be used and this young generation reclaimed it to be a bit of a badge of honor today.

    Recently, Jacob Tobia took the former insult "sissy" and turned it into the title of their biography. If you haven't read it, it's quite good. I say "recently" but the book was released in 2019!

    As a kid, I always worried about my secret being discovered. Even now, I worry that my Mom might be angry if I told her that I live openly as a woman on a daily basis.

    As an adult, I still worry that someone would harm me or my family because of how I dress. But the longer I'm living openly in public, the less frightening it is and I don't worry nearly as much.
    I guess that it's admirable that younger people are more confident and able to open doors that we thought were locked to people like us and now that we see the whippersnappers blazing a trail. Now I'm running down that same trail in my dress and heels yelling to them, “Wait for me!”


    1. As far as wearing dresses, I have not worn trousers since the middle of June. You know I HAD to wear something. You can't go around naked. So I wear dresses, at home and out in public. For church I even add heels and makeup. And it doesn't bother my mother at all with my choice of attire. And guess what? I have received virtually no pushback.
      I have NEVER been called a sissy within my adulthood. I guess my deep masculine voice might have something to do with that.


  10. Sexual equality is an area where half the population is more equal than the other
    They can wear pants, skirts, dresses, anything they like
    The other half are restricted to pants regardless of the air temperature

  11. I've written about this before. When I was eight I was forced to play a girl's part in a little "Parent's Day Show" at a summer day camp. I was not asked if I wanted a girl's part and once it was assigned, I felt ashamed and extremely humiliated. Moments before the show, just after I'd been dressed up in a pink dress, wig, and make up, the Day Camp's director touched much under my dress and told me to be a good girl.

    I don't recall exactly what happen, but I recoiled and he backed off. I had no idea he was trying to sexually assault me. I didn't understand that kind of thing at age eight. I thought he was teasing me for wearing a dress.

    The audience's reaction to the several young boys dressed who walked on stage dressed up as girls still makes me queasy. I hated it. Some of my friends relentlessly teased me and gave me a girl's name. Some claimed I'd turned into a girl. I guess that was the biggest insult they could throw at a boy.

    Beginning at age 12, secretly, I began to try on my mother's dresses. I loved wearing panty girdles, nylon stockings, slips, and pretty dresses. It felt exciting and liberating. It still does, but wearing dresses didn't help my teenage self esteem. For years I wondered what was wrong with me.

    Honestly, and not to minimize what women feel, I get the "why me" movement. How one person's act can affect another person's entire life. It's unfair. If I was destined to become a femulator, I should have been free to discover it on my own and not forcibly dressed up as a girl for I endured utter shame.


  12. I love this post! You are "Spot on" as to how society treats men who exhibit feminine behaviors or traits. I'm transgender now (for many years) and can be as feminine and girly as I desire. But growing up I was always called a "sissy" among other names. I cried and cried until I finally understood not to let other people's meanness affect me.

  13. It's great to read all of these posts and there are not any derogatory adult terms or words!

    1. I try to keep the blog as family-oriented as possible.

  14. AnonymousMay 04, 2024

    I prefer to wear short dresses with heels and bare legs since being the femme is more fun. while the butch woman who I befriended wears the pants in the relationship. When we go out most of the people who are supportive are women we occasionally see who has the smoothest legs who needs pants. In the summer I swim and surf in one piece swimsuits one even has polka dots.