In the past I used to read through forums at crossdressing websites to dialogue and also to get a sense of what crossdressers are feeling and experiencing. One thing that impressed upon me many times was seeing that most crossdressers continue to experience guilt and shame about their crossdressing even after years or decades of doing it. It just doesn’t go away easily. Men feel guilty about their crossdressing and it is a constant battle to suppress that guilt. Sometimes the guilt explodes in a purge of the female clothing. Sometimes the guilt causes the crossdresser to post a new forum comment or a new blog post in which he talks about his guilt and how he feels like quitting.

When crossdressers respond to these people thinking about quitting, their responses are usually very similar: “You shouldn’t feel guilt and you shouldn’t feel shame.” “You just feel that way because of how people in society look down on us and don’t understand us.” The advice that is usually given is that the urge will never go away, and so the best thing to do is to plow through the feelings of guilt and shame, accept who you are as a crossdresser, and continue crossdressing. In other words, bury the shame and guilt and push forward.

Shouldn’t these repeated posts tell us something? Can you really suppress all this guilt and shame? If you are doing something that continues to cause you such pain, anguish, guilt, and shame in your heart, might the better solution be to work hard at no longer doing this activity, to heal from the guilt and shame so that you no longer have to feel it?

I used to feel guilty about something that I shouldn’t have felt guilty about. Growing up I thought it was sinful to drink alcohol and that it always leads to drunkenness. But someone corrected my view of Scripture on the alcohol issue, gave me a brief education out alcohol, and then I tried drinking. And I felt fine about it right away. The guilt has never come back even though I drink on occasion. Since Scripture and my conscience both do not give me guilt about this issue, my conclusion remains that drinking alcohol is not morally wrong.

But crossdressing is not like this, not for me, and clearly not for most crossdressers out there. They keep trying to persevere in crossdressing through the guilt and shame, but no matter how much they try to suppress the guilt and shame, it just keeps coming back. If the crossdressers are right that crossdressing should not produce guilt and shame, then why do the people keep coming back to post on forums, even 40 years into crossdressing, explaining that they still feel the same feelings of guilt and shame and are thinking about quitting?!

I say in love to the crossdressing community, please stop trying to suppress the guilt, but rather deal with it in a healthy way. Maybe your guilt is telling you that you are doing something that is wrong and not good for you, even if it feels good in the moment. Once I gave up crossdressing, the guilt and shame in my life over that issue disappeared and I’ve been living in peace and happiness ever since, never once regretting the decision I made.

Please also read this other post I wrote about guilt which gives several other related ideas – Guilt is an Achievement!