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Society is slowing changing, but the time to reject these outdated messages is NOW.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. For 57 years I beat myself up with guilt, shame and anxiety. no more for me. At 57 I found a gender councilor who helped me to to grips with my true identity. I dress when I feel like it, go out when I feel like it, dress androgenously day in and out , underdressed all the time and don’t care if bra straps show. My wife and children had a bumpy road for a while but are now becoming more accepting. At 63 my anxiety is gone the guilt is gone and if the world has a problem with me it is there problem not mine. My ears are now pierced, wear earings all the time, toes polished, nails polished, my shoes are all 2 to 3 inch heals and running shoes women’s. I am now much happier and had I been 20 again would have transitioned.

  2. It does irritate me when women can work male jobs, dress like males then go home – girl up and no one cares. I do understand the issues women face with oppression, abuse, etc. Men’s clothes are boring – we haven’t changed styles in 100 years! If you don’t like sports or cars you are not “male” enough; if you like a cute dress or pretty heels – you are not “male” enough”.

    Very frustrating – its ok if girls strive to be male – go up the social ladder – but not ok if boys wish to express their feminine side – like we are going down the social ladder.

  3. I do feel anger and jealousy on women because I don’t have the right to look or act in a feminine manner not like genetic women that can act or look masculine or feminine and it’s considered ok

    so to help me out I just put out my anger and jealousy on other things

  4. great post. I felt almost ashamed. It is very hard with no support system. I eventually opened to a girl I knew and she helps me which is needed

  5. Good article, we live in masculine ssociety, Japan is more of the opposite, and some other Asian countries where crossdressing is much more accepted amd considering the M2F crossdresser as cute/beautiful.

  6. I used to feel guilty, it is still hard to be who I am. It seems to be only a few people that are extreme and tose people are the on’s we need to go after. Protection laws that are very stricked. i.e. a trans gender person is beat up, regardless of the reason, (unless there is proof of the trans being the attacking one) the attackers need to be punished severally this would stop a lot of attacks. It is time to send a message to those few, their fear will no longer be tolerated.

  7. I used to feel guilty, embarrassed, paranoid and freakish about it, but over time it wasn’t an issue. Sometimes I would just take a tiny step (which seemed like a huge scary step at the time), like wearing a dress for the first time in front of my family.

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