Do You Feel Guilty About Crossdressing or Being Transgender?

crossdressing transgender guilt

Do you feel guilty about crossdressing or being transgender? A lot of “my girls” tell me that they do.

If you have to lie or sneak around to keep your femme side hidden, then I can see how that would bring up guilty feelings.

But let’s get one thing straight – there’s nothing wrong with crossdressing or being transgender.

We live in a world with very defined gender roles. Unfortunately, these roles are even more rigid for males.

It’s OK for women to express their masculinity by dressing like tomboys or by acting strong and assertive. But if a guy acts feminine, he’s labeled as “weak” or “gay”.

The underlying message is that it’s OK to be masculine (even if you’re a woman), but femininity is something to be ashamed of.

What the heck!?

Society is slowing changing, but the time to reject these outdated messages is NOW.

I think Iggy Pop said it best:

“I’m not ashamed to dress like a woman because I don’t think it’s shameful to be a woman.”

Iggy Pop dress quote

I’d love to hear your thoughts on this topic.

Do you struggle with guilt or is it a non-issue for you? How did you deal with your guilt and how would you advise other girls to do the same?

Please take my poll and leave me your comments below!


Do you feel guilty about crossdressing or being transgender?

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Feminization hypnosis - The Femme Hypno Transformation ProgramP.S. If you’ve been struggling with guilt and need extra help, you might be interested in my Femme Hypno Transformation Program.

I created this program to not only to help you express yourself as a woman, but to let go of emotional blocks that are holding you back. Click here to learn more now.

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  1. When I was younger I often felt guilty when I would crossdress because I would almost always end up satisfying my sexual desires. I found that instead of a feeling of fulfillment or pleasure I would be filled with the fear of being found out. As I got older I learned to focus more on the joy that crossdressing gave me and less on the negative feelings or concerns about what others might think or say. I became a very confident person and began buying my own feminine things rather then borrowing my older sisters things. Every now and then the demons of doubt and shame would reappear and I would find myself purging some of my girly things. I am now at a point in my life where I have no more doubt or shame. Those feelings have been replaced with an overwhelming sense of hopelessness that I will never truly be able to express myself the way that I have always wished that I could. I am stuck in a sexless marriage and my needs are not being met at home. She has known about my crossdressing ever since our first year together and I have never tried to push it onto her or make it part of our intimate time, but I think she always felt like she was competing with my other self and just gave up on me. I have never been unfaithful to my wife, but I need the love and acceptance that she is unwilling to provide. I honestly don’t believe that any woman could provide my with the pleasures that I find myself wanting. Am I a horrible person for entertaining the thought of betraying my marriage or do have the right to explore my options based on my current situation? I just want to be happy.

  2. Hi Lucille honey I’m still waiting on my check of course the paperwork arrived at my home so I’ll have to go by again and check the mail it may be there waiting for me I hope but I doubt it I’m really tired of waiting on it to show up but there’s nothing I can do but wait I’m trying to stay positive it’s beginning to be a challenge though I’m so ready to start my transition but without my check I just have to wait Love M.J.

  3. Hi,

    Today I tried my first wig. Last week I learned how to apply, or tried to learn how to apply makeup. I recieved my glittery gold pumps today as well as my new silicon push ups.

    I have manufactured my own breast fillers and the work and feel so wonderful, bouncy like real boobs and soft and easily made in variety of sizes, and they feel very real. I am working on perfecting that.

    I shopped at Ross and Target last year, and gave it all away to goodwill in a moment when I doubted who I am becoming. So, I shopped again recently. I even checked in at the dressing room with hand full of dresses and skirts. lol. I was so excited and I could care less if the girl there thought I was a freak, because I am freaky me, Daniella Prime, or Davina.

    I am on my way to really being happy, even if it is only in the closet mostly for now. I plan on dressing to the nines tonight, and go out for a drive. Cant wait to put on my makeup and get dressed, and walk outside where I can be seen. So excited. So so excited. It has been 53 years in the waiting. Ever since I was a little boy and was fascinated and embarrassed about my desire to touch lace panties and soft garments. I am a masculine tall man, but have a female heart and soul. And I am loving the fact that we can see the light, there is light, we will be accepted sooner or later. Thanks to Caitlyn for passing the message to millions recently, but moreso to all the transgender folks that have struggled to do so with little help and much pain. They are the real heroes because they dont have such privelege as Caitlyn does. The heroes are the ones in the trenches, getting the word out that transgender people are people. Yay.

  4. Thank you Linda that’s a good philosophy I’m trying to move forward myself and I do need to let go of the past forward is all there is and be happy I’m doing that too getting happier day by day and soon I’ll be very happy when I start my transition it may be a little slow at first but I know which direction I’m going Love M.J.

  5. yes I have felt guilty in the past but the more I keep going over all I’ve ever felt inside I’m beginning to feel guilty for trying to be something I’m not to me my gender is between my ears not my legs I’ve always felt more in my offender its actually offensive to me it disgusts me that I’m not the gender between my legs that I am between my ears Love M.J.

  6. I was the only male child in a large family, my father was a traveling salesman and was never home, so I had no strong male roll model. I didn’t learn to be a boy, but my mother was a very devout Christian, so any so called feminine traits were punished. I learned to hide who I was growing up to be. I’m now in my 50’s, and just trying to learn how to be myself. I still feel ashamed of my feminine attributes, but am going to counseling to try to integrate all of who I am. Still not sure who that is, but now I have the gift of being able to make the choices and become who I want to be.

  7. My Personal Philosophy

    Do Not Discuss the Past.

    Do Not Discuss My Life Before.

    Work Hard, Be Happy.

    And Enjoy Your Life.

    I Will Not Allow Anyone To
    Endanger My Way of Life.

    To Live, Find Value In What You Do.

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