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Society is slowing changing, but the time to reject these outdated messages is NOW.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. yes and no,when I am dress as a woman the guilt is gone and are one of the girls,but with work and children around I do as work deals with oldtimer set in there way and seeing what it does to kids when a adult comes out means I have to lie to them so they don’t know,i wan to share it but cant,i think the guilt is more of lieing to them all

  2. There is nothing wrong with being a crossdresser. I don’t feel guilty wearing women’s clothes. Be a crossdresser is a part of who I am and I wouldn’t do anything to change that. I am proud to be a crossdresser because I feel very comfortable in women’s clothes.

  3. Hi to eveyone! I read a few of these comments and that give the guts to comment with my true name and everything.
    About the topic, i just recently try to be a girl but since middle school (im on the university now) im attracted to the woman clothes but i never found the courage to talk to this with nobody until now, my boyfriend is encouraging me to do what i want and still i feel a little of shame walking in a cloth shop looking for skirts or panties but im trying my best to accept what im i, a girl in my mind but with a man’s body.
    Also i think that maybe in the futute i can go out in public as a woman but that going to requires time to adjust my shape and confidence.
    Soo…long story short, i still feel me guilty but now is less than in the past and im going to continue this until i can be called “rebecca” that’s the name i want as a girl!

    To be honest, i feel me sooo good after tell you all this nwn

    Thanks to make this blog, and thanks to all the people that leave a comment too.

  4. The question asked was, “Do You Feel Guilty About Crossdressing or Being Transgender?”

    OMG! How many feelings and memories this simple ‘yes’ or ‘no’ question invokes.

    As a life-long crossdresser a simple answer would be, “Yes!” But it’s not that simple. It took me years and a lot of guilt before I was diagnosed as being GID. Once I accepted the fact that I am physically a male and mentally a woman, I’ve come to love and savor being transgender and I love being able to dress as a woman when I get the opportunity.

    So, my simple answer is, “No.” I am very comfortable and love being a crossdresser and a transgender.

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