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.

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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I have enjoyed cross dressing since I was about 7 years old. I like a little of both worlds. I enjoy makeup, both with and without a beard, I enjoy wearing a thong every day. I keep my body hair short or shaved and my nails longer. I have feminine characteristics like wearing makeup weather I am cross dressing or not. I like red lipstick but most of the time I wear a nude color lipstick throughout the day. I wear concealer on occasion and a little eyeliner. I like traditionally women's type clothing like wearing a T back tank top and yoga style pants. I like the feel of a bra and I enjoy spaghetti strap tops. Even thought I like these feminine items, I like being a man as well. I like having muscles and being strong. I like to get dirty under the hood of a car and go camping. And sometimes, I like mixing both such as I mentioned above. Having a beard with red lipstick on is sexy. Most of the winter, I have a full beard and I still wear concealer.

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  1. Alice 7 months 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 7 months 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 7 months 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.

      • Alice 6 months ago

        Thank you Stef.

      • Chrissy Landwer 6 months ago

        I can’t agree more.

    • Author
      Cindy Carpendar 6 months 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.

      • Alice 6 months ago

        Hi Cindy, I hope so too! Thank you for your words of encouragement.

  2. Stef Smith 7 months 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 6 months ago

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

  3. Sharri Roberts 7 months 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 6 months 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. Christina 7 months ago

    That’s pretty awesome. Just saying…

  5. Rose3400 Garden 7 months ago

    Nice share..
    thank you

  6. Jessica King 6 months ago

    It encourage ing too read its alot what ive been going thru its been a big secreat over my head and i thought it mean something was wrong cause not gay just enjoy and acting as woman but due to family and loss of my babys mom for not understanding it made me push it back again and hiding it still due to that its so hard for fear of judgement

  7. Chrissy Landwer 6 months ago

    I’m a cis man I think. I have mixed feelings internally but am masculine on the outside. I love fine things and coordinating clothes and noticing detail in so many things.
    My testing results scored 90% fem. but my world would be shaken if I revealed my true interests and desires. I don’t know why we need to consider others when it’s our lives.

    • Stef Smith 6 months ago

      I hear you
      We consider others because we love them and wish to do them no harm
      It is a delicate balancing act to be true to self and protect our loved ones
      And then we have to decide if the ABSOLUTE truth is really ABSOLUTELY the best thing to do

      • Chrissy Landwer 3 weeks ago

        Thank you Stef. I wish it were easier to chat and meet and talk in person.

  8. Christie Deville 6 months ago

    thank you for sharing

  9. Erika Jiame Jiame 6 months ago

    Being in Law Enforcement I really had to keep my dressing private. I loathed this fact.

  10. Erika Jiame Jiame 6 months ago

    OMG! My secret was %100 job related. At 22 my life took me into Law Enforcement. I do feel your pain as it wasn’t feminine men friendly.

  11. Marsha Isme 6 months ago

    Hi Cindy,

    I just joined the site today. It seems many of us have similar stories. My wife, of 49 years, has never known my secret. No one has.

    I have bought clothes while traveling for work, and thrown them away before leaving for home. And, never worn them outside if the hotel room.

    Well…. Ok. I have worn panties, under my suit. But, not for long, it’s always that hospital emergency room issue in my mind…..

    I have never felt gay, and always been attracted to women. Infact, my secret desire is to have a sexual encounter with a woman, while dressed…. With her full knowledge of my true gender.

    I am happy to be here and share.

  12. Melissa Davis 6 months ago

    Those who are troubled about whether to be honest with a companion might find it useful to see the Tim Burton Movie ED WOOD, based on the true story of an an enthusiastic crossdresser in the 1950s who is remembered today as perhaps the most amateurish in Hollywood history. Wood’s best known picture is GLEN OR GLENDA, in which he plays both parts. (Both movies are available online.) ED WOOD is a very funny comedy, with Johnny Depp in the title role and a great cast including Bill Murray and Martin Landau (who won an Oscar for it). There is a touching scene in which Ed is driving with his girlfriend and slowly brings up his cross dressing, not knowing how she will take it. When Ed asks if she can live with that, she thinks a moment, then asks he still loves women. When he says yes, the girlfriend thinks just a moment and says something like That’s OK with me, almost as if he had asked if she would object to his wearing wingtip shoes. Good message in an entertaining comedy.


    • Melissa Davis 6 months ago

      I dropped a word in the post above. Make that “the most amateurish director in Hollywood history.”

  13. Samantha G..... 5 months ago

    Great article Cindy !!!

  14. michelee 5 months ago

    It’s so reassuring to hear my story as shared by another person. Thank you so much for sharing your emotions.

  15. Harietta 3 months ago

    These are all great views and well expressed.
    I still think that I have found a happy medium in my “management” of my gender fluidity.
    Fear the “Pink Fog”.
    It takes discipline, and more and more these days given the dangerous fire storm that social media can create.
    Evidence…it’s not about cross dressing but this week in Ottawa we have a case of a longtime member and former minister of both provincial and federal losing it all on social media. His Willy spoke to him louder than his noggin and he las been dismissed and his family shamed.
    Something to think about for we shes who choose to remain hidden from our spouses, bosses, friends etc.

  16. Chrissy Wantin 2 months ago

    Hi Cindy, I’m in the closet CD and am petrified of coming out. After reading your post I’m thinking and I mean JUST THINKING bout coming out. I worry so much about what others will think or do. If I had a CD girlfriend to encourage and show me the way I think I could do it. Thats why I came to this site, to hopefully find a friend to help. All the other sites seem to be just for sex,sex,sex.and as we all know there’s more to this lifestyle than sex. I’m in Richmond,VA area so would greatly appreciate any help from nearby,thanks… Chrissy

  17. Lilly 2 months ago

    I’m reading though a lot of articles because I’m finding myself in the same boat as you. I am proud and happy to be a man, but also very into women’s things ever since I was a kid. I can’t help it, it feels so good but the feelings are scary and conflicting. I have partially told my fiance, she knows that I wear panties, but not about the dresses. I want to share it with her, to have her at least know that I do and that I like to and that it doesn’t make me any less of HER man, but the fear of rejection is so strong. Like you, my intention is not to betray her trust in any way. I love her too deeply for that. While it is easier for someone like myself to cross without too much fear in the public’s eyes with the modern times, the thought of stepping out of the closet in any way still terrifies me even if transparency is my end goal.

    Timing is wrong, we are getting married soon and it’s the holidays. We need a quiet summer together. At any rate, I wanted to just thank you for the article, to know there’s someone like myself makes me feel a lot less lonely about it all.

    Thank you,
    – Lilly

  18. Olivia Livin 2 months ago

    Thank you for sharing Cindy. Not sure the terminology is right, but I like to tell myself I was “smart enough” to tell my gf very early on(it was scary) she was, and is awesome with it. I hope your SO’s processing is still moving in the direction of acceptance towards you. In the meantime enjoy it within your boundaries and the role reversal part. I know I do

  19. Falecia McGuire 4 weeks ago

    I don’t know what to think, but gratefully, I don’t have to. I may think that my brand of crossdressing is less ridiculous than Cindy’s, but that’s OK. Most of the things we choose to do in life have a sense of the ridiculous in their variations. The point is that we should have the choice to pursue endeavors that fulfill our needs while not harming others or impeding their abilities to pursue their needs. Morality is not about some abstract list of rights and wrongs. It is about charity, kindness, and genuine empathy.
    Bless you,

  20. Harietta 3 weeks ago

    The ongoing normalization of crossdressing seems to be taking some of the thrill, alla playing hooky, out…Mais oui?

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