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Society is slowing changing, but the time to reject these outdated messages is NOW.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. I have felt guilty many times because of my crossdressing. I purged so many times that i lost count. When I was younger I actually wanted to be a girl. I am much older now and realize that being a woman is not realistic at this point in my life. I did finally find a gg who understands my dressing and supports me. I have been out dressed but only with friends or a group. I live in a small town, so going out dressed here is not an option.

  2. I just feel I’m letting all my friends and family down,they won’t understand,so I have to keep it a secret,even though I don’t want to

  3. I don’t feel “guilty” – but I’m a well known personality in my little town and I can imagine what does the people say about my transformation. This way here I go out by car or steps in evening hours and better like to go out in other towns.

  4. As a man who did a lot of ‘man’stuff before I realized Olivia was inside, I am very open about my transformation. Even to the point of embarrassment for my wife.

    I will walk into Wal-Mart and shop for panties and bras. I will talk to people from my Church and even (for the first time) got my nails done. The woman sitting next to me even asked if I was doing a “Bruce Jenner” thing. I said…welll……

    She took a picture of my nails to show her husband that yes men do get their nails done too.

    I may not be ready to get a dressed up as Olivia and go out. I need to work on my face, voice and make up. But besides the face and voice, I really do look better as Olivia than my wife does dressed.

    I do not feel guilty. It has been a huge relief to open up to my inner Olivia. It has been and will be a great journey for the rest of my life!

    By the way….learning to type with nails was kind of challenging! 😉

    Thank you for this blog, it really is a great place to be open with others that may face the same issues I am.

  5. I voted no because I no longer feel guilty. But, I did feel guilty for many many years. I have not like that since I came out, yea!!

  6. Last year,I went through the acceptance/denial stage of my crossdressing.I was,also,going through my mom’s battle with cancer and eventually her loss.I love wearing women’s clothes and like looking in the mirror and enjoying the look and feel of the Top or bra I’m wearing @ the time.I should not feel guilty for something I enjoy and causes no harm to others.I have come out to a few people recently including my sister.My father and my 8 year old niece No.I just bought another pair of ladies shoes,today.They are Montego Bay Club black and gold ankle strap platform wedges and I love looking @ them in the mirror when I have ’em on my size 10 feet lol!!

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