Why I Kept my Cross Dressing Hidden

As a man who enjoys crossdressing on a regular basis, I can easily say I made the same mistake that most other men do. Not telling our SOs. We grow up knowing that we like women’s clothing. Everyone likes different aspects of it and everyone has different reasons as to why. But we also grew up in an era where this was highly unacceptable and kids got picked on for it, even if looking feminine was unintentional, such as wearing tight pants because we could not afford new ones or a “girly” color as part of our outfit. The crossdressers of my age saw that, or were a victim of it, and made sure they kept that aspect of their life hidden. Even with people I love very much, I could not be open. I didn’t tell my mom, my friends; I did not tell my SO, who I ended up marrying and with whom I shared many other secrets. By that time, I was “built” to keep my crossdressing hidden. Many times I’d try to put it away and think “it’s just a phase.” But the reality is it’s not a phase; it’s a permanent part of my life. It’s something I enjoy doing. I can’t pinpoint why I like it, but the point is, it’s there.

But this is why I hid it. It’s not that I didn’t trust my SO, even though that is what it seems like. Society brought us up that way in the 20th century. Nowadays, in my kids’ era, crossdressing is pretty acceptable among the right group of people. Finding resources is easier due to the internet, and people are not as closeted as they once were. More people find it acceptable as society, today in the 21st century, mostly allows people to be who they want to be. I see guys wearing sports bras at the amusement park, and guys with beards wearing makeup as a style, which I myself have tried and like. Tight clothing has become a thing of the past as being a women’s style only. I was recently able to buy a pair of stretchy tight pants at the store, in the men’s section. Sometimes I wish I had been born about 20 years later because these things are more acceptable now. It would have been a lot easier to communicate it to my SO, but then if I was born 20 years later I would not have met the woman I am so dearly in love with and will hopefully live the rest of my life. She makes me happy and I cannot see a future without her.

Eventually, my SO became aware of my crossdressing and out of respect for her, I now have my own clothing and my own makeup. I do not dress in front of her, as she is not yet ready to see me. A couple years into it, and she is still processing. I felt it was very important to let her know that betrayal of trust is the last thing I wanted. I have no intention of leaving. Just because I like dressing as a woman does not mean I like men. I am very much attracted to women. I enjoy being a guy, and taking on the role of the protector and the strong father, even though I might be wearing a pair of panties underneath it all or dressed in full role reversal in the bedroom.

Crossdresser Heaven - Find Your Tribe

And on a late night walk, I pity the fool who thinks he is going to harass a couple ladies walking together.

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  1. Rose3400 Garden 1 week ago

    Nice share..
    thank you

  2. Christina 3 weeks ago

    That’s pretty awesome. Just saying…

  3. Sharri Roberts 3 weeks ago

    Yes Donald Trump is trying to turn back the clock 50 years and destroy all of the advancements er have made. Its a very sad state of affairs that a president could be so closed minded and unwilling to live and let live.

    • Author
      Cindy Carpendar 2 days ago

      I don’t think Trump will be around long enough to do too much damage to the cross dressing and transgender community, but you are correct.

  4. Stef Smith 3 weeks ago

    Great comments
    I m in your category if I may use that word
    I enjoy crossdressing but love my make role as well. Andvlets face it once you take on a persona its hard to switch it
    If you start out dressing a little femme and meet someone they already know and somewhat accept it so its easier to tell them
    I love my male self and role and I m only attracted to females
    So I understand you completely

    • Author
      Cindy Carpendar 2 days ago

      Thanks Stef for reading my story. Yes, this day and age it’s easier to meet someone and talk about things like this.

  5. Alice 3 weeks ago

    Hi Cindy, Thank you for the well articulated article. You have described almost 100% of me. Like you, I have a very caring significant other who shares many of my personal value and been very supportive to me when we experienced challenges in our life, except my gender preference. She does NOT believe in gender dysphoria (although she is a Psychiatric Nurse by training) and is openly against crossdressing. She caught me once wearing a bra. Immediately, she shamed me! I shared my desire with her. Immediately I sensed her disapproval, hurt and disappointment. I am afraid I will only fulfill my wish in my next life, if there is reincarnation! Having said that, thank you again to you and all those who responded to your article. You helped me realize that I am not alone.

    • Stef Smith 3 weeks ago

      Dont be ashamed
      You are jyst a person who likes diing somethhing society doesn’t like
      In the end clothing does not define you
      You are still you with or without the clothes
      Accept yourself for who you are
      Love You theres only one of you!

      • Terri 2 weeks ago

        Thank you for posting your story. My wife has known close to 40 yrs of my dressing. She has only seen a pic of me dressed once. I hang some of my female clothes in our closet. I know she will never accept it. But she is a good wife, mother and I will always love her. But I know she Will never understand or accept Terri.

    • Author
      Cindy Carpendar 2 days ago

      Alice, I would hope some day your wife will start to learn about gender dysphoria in her training and maybe start to see a different light. My wife is a nurse as well and accepts others for who they are. her argument is that she didn’t marry a woman, she married a man. I as well hang my clothing in our closet like Terri and makeup in the bathroom on my own shelf. We just don’t play together when dressing. I still have hope. but for now, enjoy your friends here continue to have fun with yourself.

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