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Society is slowing changing, but the time to reject these outdated messages is NOW.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 voted no but the real answer is people that are close to me often get embarrassed if someone should see me dressed like a girl. So basically it is them that has guilt issues not me. I get mad if I have to hide the way I dress from anyone. The whole purpose of coming out of the closet when I did was so I did not have to hide my femininity any longer. That is still an issue with some friends and family but I just keep dressing like the woman I am.

  2. Hi Girls. If it was 100% OK to dress anyway you like in the world then I would cross dress everyday. As it is, I only do it every few weeks when I can. I have dressed to some degree since I was a teenager, but over the past 3/4 years I have lived alone and it was possible to dress up more and more. I go for the whole thing, make up, perfume, wig, jewelry, shaved body, painted nails, high heels, lingerie and dresses. I find the more I do it the more I want to but still get this guilt thing the next day. Almost like the feeling that I am doing something wrong but I enjoy it so much that I don’t want to stop. I wish I could be more open about it but you are always looked upon as being a freak. The guilt thing is less than it used to be and I hope that one day it will not be there.

    • Lucy Lou,
      I do sometimes feel guilty about my crossdressing and I know that I shouldn’t. I am married and my wife has known about my desires to wear feminine clothes ever since our first year together. Although she is aware of my crossdressing, she doesn’t like to talk about it. I recently tried to talk to her about some of my frustrations and self doubt I have been experiencing due to strong feminine thoughts and feelings that have been consuming my body and mind. She replied that I was just being silly and changed the subject. I realize that her reaction is just a defense mechanism to help her deal with her own denial on the subject because she doesn’t want to talk about it. She is fortunate in the fact that she can choose to ignore such things, but I don’t have the same luxury. I can’t dismiss the issue and just hope that it goes away because I have to live with the overwhelming thoughts and emotions every second of every day. I love my wife very much and the last thing I would ever want to do is hurt her, but I am finding it more and more difficult to control my feminine feelings and desires. I have purchased a few items to help me fulfill some of my needs and even though I have enjoyed the Sensation’s that they provide I feel that I might have to take

  3. I started crossdressing when I was 12, I am now 46 years old. I am not gay although sometimes I think I might be. I have always keep it to myself dressing up, I got married. I told my then soon to be wife everything and at first she was ok with it, now we are divorced. I have had some girls who have helped me in the past with shopping as I find it very hard on my own. I am looking again for some help but that’s just as hard as shopping itself. When I shop on my own I a scared but when I get home I cannot wait to try everything on. When a girl helps me I have so much fun, why can’t there be more women out there that would help instead of looking down at us. I now live on my own I don’t have any male friend as I don’t want them to find my cloths, and that’s the same with women. I just go to work and come home, I am dressing up a lot more now and it’s a great relief when I do dress up, and also talk about it, but who will listen. The last time I went shopping a women dressed almost like a man was laughing at me because I was looking at dresses, what I was upset about nobody looked at her twice with the way she was dressed, but would it be the same if I was wearing a dress? I dress up for me it make me feel great I don’t show anyone, I don’t hurt anyone. Ok I look silly but to me I feel great and to me that’s all that matters.

    • Hi Mark how do I feel for you , yes I do my experience was that I went to a supermarket dress up , but when I got to the till I found it somewhat embarrassing when the teller said oh look its one of them, I run out almost in tears , so I you can appreciate I don’t do it very often and when I do it it’ll have to be late in the evening .
      And like Michelle may be we could talk to each other .
      Love JAS

    • Mark, I understand, I am 49, been cd all my life. I hope you find understanding friends because we all need others.
      If you reply maybe we can be Pen Pals.

  4. i went through torture they put electrodes on my temples disguised as tinsel temple probes and shock treatment through my body electricity shock treament

  5. hi lucille i have a natruele cycle i dont wat u to take this wrong i have a natruele cycle i have a peried every moonth i come on i use tampaxes wen i spoke to a female doctor she told me it was natruel for a trans gendered woman my mother argued about this saying i was mentaly deformed and this wasent possible but i can not help this my mother got her ba srd boy freinds kick the crap out of me she thrived an loved i ended up in hospital on so many ocasions wen the authereteis got involved nobody would beleive me i ended up in care for my own protection ther was my carer who helped me but the worst thing iended home whith my abousers and that is my nightmare i do not like my mothe for wot she did to me you are wandering why i am telling you this it is about time the truth came out it has been bad for me i have had enough i want to be me whithout pain whitch i have had enough

  6. Hello, I’m still relatively new to crossdressing, but I honestly have to say that every time I do, I feel like my natural self, and it’s so much fun to do my hair and makeup every day. Although I’m not scared in the last bit to crossdress in my house around my roommates, I do get butterflies in my tummy about crossdressing in public, though I have done it once before. I’m still trying to get over that fear and I know that someday I will, because I consider myself to be a very confident “woman”. I used to feel very guilty about crossdressing at first because I didn’t know how my roommates would react to me being a crossdresser, but once I talked to them learned that they were OK with it, I was so happy that I broke out of my shell immediately.

  7. Hi everyone,

    I found this incredible site a week or so ago and have read with interest. This is thankfully the first really useful site that has got rid of pretty much all of the sometimes bizarre stereotyping that tends to exist. I did the test on Monday and scored 100%! I have known without any doubt that I am female from the age of six or seven. I had the luxury of growing up in the 70’s where the gender lines were more blurred than now, tight jeans, vest tops, leather fringed jackets and frills were the norm. I dressed as I wanted and ALL girl, what I loved more than anything was my hair, deep brown, and a mass of salon curls and red highlights, and to just above my knees. I was even wolf whistled on a regular basis, my sister told me I caused a car to crash once when I dropped my bag and bent to pick it up, I said he shouldn’t have been ogling my bum!! God I miss it! Then my world fell apart, I may tell if asked but at this moment suffice to say that it destroyed my life and it has taken me 35 years to get over it. OK, fear, self loathing, guilt and confusion, they are there and to all intents and may always will be. But is that what we display, or what we reflect from others? We are all after all a mirror hostility will evoke a reaction. I have to say that I have taken some strength form a very unlikely source girls, Lady Gaga, listen to her, Born this way and scheisse! the line I love more then any is If you are a strong female you don’t need permission! I go on, I live, or is that exist? In a sort of pseudo reality a women in everyway that I can be. I cry, a lot, my wife asks why, I just call myself Gods Friday afternoon special! :) a rush job never quite finished correctly. I still have a good figure 6ft tall and on a good day eleven stone, size seven feet and small hands. When We go to fashion shows my heart races every cell in my body screams. I now have to tell my wife, :( enough is enough, I am not a freak, and neither are any of you, you are all stronger than any man and far more woman than they could ever handle. I will die the way that I should have been born. Sorry for the ranting girls. Now where is my bag and purse time to shop I think. I have 35 years to make up for!!:)

    Love to all of you


    • Hi Jayne .
      You wonderful girl you go for it and do hope that you go ahead with it and Jayne do keep me in mind as I also need want some support .
      Love JAS

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