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What It Is Like To Be A Crossdresser (To Me)

September 30, 2018


My experience as a crossdresser is unique to me.  Labels are an attempt to simplify complicated things.  I am not explaining the label.  I am explaining how I personally feel, think, function, etc. in regards to the impact of my crossdressing on my life in general.

Foundation Facts

This list applies to the state of affairs right now.  Many of these facts might never change.  Nevertheless, assume that this list is out of date.

  • I am a man who likes to wear women’s clothes.
  • I never present female.  I just wear a skirt or dress as a man.
  • I own three pairs of women’s pants.  Of those, I have only worn one pair out of the house on two occasions.  If I am crossdressing, I am probably wearing a dress or skirt.
  • I like to call it “dressing pretty” when I am crossdressing.
  • My wife knows that I crossdress.  She does not like it.  I can wear pretty things at home around her after the kids in bed.  It might happen once or twice a week.
  • My children, parents, siblings, friends, church, anyone else who knows me does not know that I crossdress.  EXCEPTION: I told my sister about this many years ago, before I had ever had a public outing.
  • I go out in public when I am “far enough” from home.  Sometimes I risk going out in public closer to home in controlled settings.
  • I do not want to crossdress full-time.  If everyone knew I was this way, I believe that I would still routinely wear menswear.


This list gets more positive…  🙂

  • I feel lonely.
    • I am always alone when I am crossdressing.  This is not a choice.  This is the way things are.
    • There is no one I can talk to about it.  I cannot ask women at work where they bought their cute shoes, etc.  I cannot share happy stories about my crossdressing adventures with anyone.  I have no one  of whom I can ask advice.  EXCEPTION: I made friends with the owner of a consignment shop.  She asks me about my stories and gives me advice when I go there a few times per year.
    • Although people treat me with respect, they are less likely to talk to me when I am dressed pretty than when I am not.
  • I feel ashamed.
    • I do not know if crossdressing is a sin against God or not.  Obviously, I think it might be a sin, or I would not have mentioned it…
    • Around men, I feel the shame associated with breaking the “macho code”.  (That is the ad hoc code of manliness that I was inadvertently trained to live by during middle school.)
    • My wife is ashamed of my crossdressing.  I feel shame when I embarrass her.  I feel ashamed talking to my wife about it, doing my laundry around her, etc.
    • Changing clothes in the car feels humiliating.
  • I feel stressed.
    • Hurrying to fit an outing into a work lunch hour creates a sense of stress.
    • Peeking into buildings before entering to determine if someone I know is in there is stressful.
    • Trying to walk, smile, talk, and interact in general in a way that reflects well on me and on other crossdressers weighs on me.  (Not walking like a cowboy cave man, and not stumbling in heels, I mean.)
    • Being different means that I get sideways glances from people.  People look at me and then look away.  A few people stare.  People do not make eye contact with me and say hello.  It can create a stressful, oppressive feeling in my heart.
    • I find that I use words like, “safe”, when I speak of places or people that I crossdress around.  There is a sense of crossdressing being unsafe.
  • Crossdressing can feel disappointing.
    • When I go out, if no one even notices me, and I am treated like I am wearing men’s jeans, it is very pleasing.  I want to feel like I am a normal person who fits into society.  However, it is also disappointing.
      • A compliment would be nice.
      • Someone engaging me in small talk would be very encouraging.
      • Someone wanting to meet me and become my friend would be perfect.
      • Those things seldom happen.
    • Finding a garment that I love, but only to discover that it is not in my size, is very disappointing.
  • I find it very exciting.
    • Sometimes I crossdress in a new situation.  The number of things I have not done is shrinking.  Fear makes me avoid some things.  Facing my fears is frightening.  Realizing my fears were unfounded is empowering!
      • Apartment complex office – Done!
      • Flying pretty – Done!
      • Hardware store – Done!
      • Church – Done!
    • Being able to wear a new outfit that I feel confident in energizes me!
    • Doing average things, like grocery shopping, while crossdressed, makes me feel like I just defeated a good competitor in an athletic sport.
    • Facing my fears feels like climbing mountains!
  • Crossdressing feels fulfilling.
    • Doing something normal while crossdressed, and being treated like I belong is like receiving a long hug from a true friend.
    • Doing something significant while crossdressed, like going grocery shopping or doing volunteer work, makes me feel like I do when I have completed a project.  It feels like finishing building a treehouse.
  • I feel pretty.
    • I did not see this one coming.  I do not want to be a woman.  I am not a sissy.  I attempt to maintain my masculinity when I dress in women’s clothes.
    • There have been a few times that I have been able to try on or purchase a beautiful outfit.  When I put on those outfits the first time, I welled up with emotion because I felt pretty.  I’m a dude.  I normally don’t care very much about how I look!  Whatever happened — it happened TO me.  I did not expect it!
  • I feel loved.


So, now what?

If you are interested, the next time you see a crossdresser out in public, or if one confesses their secret to you, consider how you could make it onto their good list of what crossdressing feels like to them.  Consider doing the following:

  • Wave and smile and do not awkwardly look away.
  • If their outfit is worthy, give them a compliment.
  • Make them feel welcome.
  • Start a conversation with them.  It can be about anything.
  • Invite them to join your group, or sit with your family.
  • Walk beside them.
  • Ask them questions.
  • Dance with them.
  • Compliment their bravery (when it is not inappropriate to do so).
  • Try to understand them.
  • Make friends with them.

If you want to take it up a notch, try acting this way toward anyone you meet!

From → Information

  1. Hello Joey. As for seeing a CD in public I am very supportive. I am very outgoing and enjoy talking with men that like to dress as a lady. However, over time I have learned there are many “flavors” of men in dresses.

  2. Pat Scales permalink

    This was a wonder post. I look forward to your posts and by commenting I hope to give you encouragement in your cross dressing and your blogging. We need outlets. Getting out and about is good and writing or even reading about others in similar situations can be helpful and empowering.
    Keep on keeping on.

  3. Well said!

  4. Earth From Human permalink

    All I can say is I enjoyed reading this.

    There is a lot of things similar with you and me. The biggest is how I feel around other men sometimes. It’s like breaking the man code or something.

    Well thanks sharing. Your story makes me feel I’m not alone.

    • TOTALLY! We are breaking the man-code that we were initiated into in middle school. “Wear your socks this way. Carry your books that way. Act this way. Etc. I learned these rules in school, around my brothers, around the kids in the neighborhood. Perhaps, my genetics also taught me some of these rules. But, I also broke them on the side…

  5. There was a man who lived near my apartment (haven’t seen him in years and I hope he’s still alive!) who used to bicycle to and from places. He loved pink and always wore pretty pink summer dresses, or slacks. The first time I saw him, he was positively BEAMING amd he exuded so much unbridled joy that it was contagious! I was choked-up just seeing how happy he was and I wanted to hug him and thank him for being such a ray of sunshine that day. Every day after I would look around eagerly for him. My wife knows about me and doesn’t like it because she feels it is a threat to her own hard-earned femininity, and I absolutely understand and respect that. Certaintly doesn’t make things easy though. Thank you for your story

  6. paula hayes permalink

    shame its a old post, but i read it , i understand it, even though everyone ,who enters that world, has gone through issues, may be have different views, their life style/ outlook, family etc . but all i can say, one way ,or another, someone will get hurt, the strain immence , the outcome for me worth while, but again i wanted to be female.

  7. Alvie permalink

    “I feel pretty.

    I did not see this one coming.”

    This is so true and so honest. This joy is not limited to one gender. It is the real joy of surrendering to the beauty of life, celebrating it in dress and movement and pleasure, a moment without harassment or shame, just truth.

  8. Smolt permalink

    Anything not done in faith is done in sin, says St Paul. Equally, we absolutely mustn’t lead children in a wrong direction. We shouldn’t worship an idol, whether directly or indirectly. And we must be faithful to our wives.

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