I periodically peruse the forums at Crossdressers.com and a number of other sites, as well as reading crossdressing blogs and the discussions/comments on interesting posts.
One thing that has impressed me is that the guilt and shame do not go away. 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. (From my amateur and perhaps faulty observations, it seems there are a few people doing this in an average week on Crossdressers.com as well as other places).
The answers given by crossdressers are always the same – “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.” Basically the advice 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.
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 this 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. So my conclusion is that since Scripture and my conscience both do not give me guilt about this issue, it is not morally wrong and I should continue to drink.
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 were right that crossdressing should not produce guilt and shame, then why do the people keep coming back even 40 years into crossdressing, still feeling the same feelings of guilt and shame?!
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!