Last week I got a resounding response when I touched on the topic of otherwise benign crossdressing websites displaying a warning. Perhaps, not so subtly asking the question – Are we ashamed of crossdressing?
I got a touching response from Michelle via email. She has kindly allowed me to share it with you:
But some of us are not proud of who we are at all. I for one am VERY conflicted. I really enjoy dressing up pretty and sometimes it is sexual, but sometimes it is not. My wife, however, does not tolerate it at all, sexual or not, private or not. I love my wife dearly, so when I do dress behind her back, I feel extremely guilty. Sometimes the guilt is because I have been to websites that I should not have been to, and sometimes it is because I have indulged myself sexually (never with another person, just masturbating, but still) and I know that she would not be pleased. Sometimes I wish that Michelle would just go away and not haunt me anymore. But then, I am irresistibly drawn to do something later that I will regret. I feel as though I have no power of myself. But you are happy with who you are so you probably don’t understand me (and those like me) and I don’t even know why I am telling you all this.
Michelle showed bravery and honesty in sharing this with me. I know first hand the pain, self-loathing and confusion she expresses. The lack of control over your desires, wanting to fulfill your needs and to still love and respect your wife. These are not easy things to grapple with. Many people never have to deal with something so heart wrenching.
Michelle’s email is a beautiful expression of a truth many crossdressers live with, and it touched a chord with me. I thought I’d share my response to her with you, dear reader.
I spent much of my life believing that crossdressing was a curse, or worse – a sin I needed constant forgiveness for. Society and religion had convinced me that I was doing something wrong. If only I had enough will power, or enough faith, or a mastery of my emotional triggers – then I would be free of crossdressing. I was wrong for doing it, and I was weak for continuing. As much as I accomplished in my life I could never conquer crossdressing. I felt powerless, until I realized that I did have the power.
I could not change my desire to crossdress, any more than I could change my height or the color of my eyes. But I could change the meaning it held for me. Up until then I had viewed crossdressing as a cross I must bear, but what if it was truly a blessing? I couldn’t make society accept me, but what if I accepted myself?
With much introspection I asked myself – why should I be ashamed of crossdressing? At this question my mind flooded me with answers, most of which involved some variation of how other people would perceive me. I tend to agonize about what other people think, but crossdress or not, other people have perceptions of me – both positive and negative that I can influence but not control. Should I be ashamed because of what other people may think? For centuries people thought ill of another based on the color of their skin. Does that mean every person of color should feel ashamed? Absolutely not!
It took a long time, but I finally overcame this reason to be ashamed. Yet so many more reasons remained. One kept nagging me – ‘was this the most productive use of my time?’. Were the hours spent perfecting my makeup technique and shopping for clothes well spent? Perhaps not – though the same could be said for hitting a little white ball around with a stick.
The mind is cunning, next it asked, ‘What about your wife Vanessa? Surely your crossdressing must do harm to her, don’t you feel guilty about what you put her through?’ Ahh, well played mind. I do feel guilty about this. For my wife I want to be the man she deserves. I don’t agonize about the perceptions of the nameless stranger on the street, but I do care very deeply about what my wife thinks.
So I took a step back, and took stock of my ‘husbandry’. I crossdress, but I’m more caring and compassionate than most men. I wear makeup, but I treat her as my equal and respect her opinion. I’d rather get a manicure than tinker with a car, but I share my feelings and listen to her do the same. I realized that our relationship to another is more complex than a single issue. How fortunate a couple would be if crossdressing were the only issue to deal with. It doesn’t erase the guilt I feel putting her through this, but it does put it in perspective. Would your wife rather you spend every night drinking in the bar than crossdress? Likely not…
Sex has a unique way of making us feel guilty – we’re conditioned to be ashamed of our bodies almost since birth. In this case, perhaps you feel uncomfortable that your desire to crossdress is partly sexual. Even organizations like Tri-Ess try their best to separate crossdressing from sexuality. This is one I don’t feel qualified to unpack, though having a sex drive and becoming aroused is natural and healthy.
So is crossdressing a blessing? That’s something you get to decide for yourself. Personally, crossdressing has made me a better person. It has also allowed me a unique opportunity to share my acceptance with others. If I can offer just one person comfort and hope, then I’m doubly blessed in getting to share my blessing with others.
You may not be able to control your crossdressing, but you can control what it means to you. Will it mean shame, guilt and heartache? Will it be a part time hobby you indulge in, as harmful as a round of golf? Or will it open up the doors to bless others with compassion and love?
The choice is yours. The only wrong answer is choosing not to decide.
Hugs and blessings,
Vanessa
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Dear reader, what do you think? How have you come to terms with your crossdressing? How do you deal with the shame and guilt? Is crossdressing a blessing or a curse?
Leave a comment and help another in heartache.






First of all it is a feeling we all have that leeds us up to crossdressing. I’m not ashamed of being a crossdresser. I enjoy doing it. I like the way I feel when I dress up and I don’t feel like I’m indecent when I dress. I’m not trying to be something I’m not I just like wearing the clothes. They feel good. I feel more relaxed in the clothes. I also do my House work dresses up.
Now you weman don’t wear skirts anymore and I love them I would ware one every day if i was not branded weared. I have told my wife and she knows I dress and she knows I’m her man when she need me the most. Now I am a man and I don’t want to change this. I don’t see where anyone can lable a person by what he or she.wants to ware. I’m not gay, I don’t have any attraction to other men. I don’t go in public dressed up. I just dress at home. I don’t want to compete with you wemon on dressing you are still the champs. I want to stay a man but I do like to dress as i want with out any lable.
You wemon that are worried about your men. Trust him help him and if he loves you he well be there for you as a man when you need him. I don’t think he is gay. If he just does it at home it is a feeling that relaxes us it feel good. You must know you ware the clothes all the time. Or is it you wemon don’t want to share with us or your partners. I bye my own clothes and I feel good in them.
So you dated us and you trusted us to marry us then trust us that we are not going to do anything gay or anything that would be against your trust.
I would dress full time if i could , i am Bi & would prefer to be a girl , i dont suffer from guilt but only dress in private as i dont wish to cause my wife any distress ,she knows & says its ok but am still too shy to come out fully . I was born into a very straight working class family & in a homophobic culture, & have lived my life in fear of being found out , i realise what this has done to my state of mind over the years , if i could be young in the world as it is now i would be out & proud , .
In a way, I guess I am ashamed of my feelings toward being a cross dresser. I have struggled with this for over 40 years. That’s a long time. When I was young I really beat myself up over my feelings. It started from my very first cross dressing experience when I was 17. What a great experience I had, but I had sooo much guilt afterward.
After that, I had so many anxiety attacks that it’s a miracle that I made it through college. I kept having these problems with public speaking — here is how it went — as soon as I would get in front of a class I was sure I would have an anxiety attack, because I had this vision that I would pass out and tell everyone that I was a cross dresser. But that never really happened, I just stressed over it.
So now I still have the same desires to cross dress. This does not go away. The only thing I can say is that the desire has never gone away. And I don’t think it ever will…
Oh Linda dear, your story is shared by so many – it’s a long road to acceptance. Even though I thought I had accepted myself, I found new ways to be ashamed
To me crossdressing is broad term I think this because I am not into dressing fully as a woman. My desire is lighter terms, in the past I have only dressed in women wear lingerie, nylons, panties, sexy wear top’s etc… The fact is no matter how much or how little a man dressing as a woman people can’t accept it some won’t even try.
I have hid it all from my family I have only told or shown only a few friends who understood and accepted this part of me. 2 years ago I have come out to the most important one in my life, My WIfe. Our sex life always was Fantasticly amazing, we were soul mates on every level of our relationship. I thought I could came out to her about me being bisexual, tell her how I wanted to dress in women lingerie. I have tried to tell her that I have already I think she knows but none of it went well at all. A total disaster, a complete train wreck, ripping of hearts out, killer of my soul. I feel so ashamed of myself, totally humiliated. She at the time did not understand, did not even try to understand or hear about any of the why? or how I felt. Once months past things calm down a little she start to open up try to understand it. At times things feel ok, she does understand a little better now, can’t say she accept it any of it, but we don’t fight about it, we don’t talk about it, we don’t bring it up, our sex life is just about gone. So she act like everything ok will admit we have a problem and we do nothing about it. It seems like she just wants it to go away which it all has in way cause we just don’t bring it up or have sex as long as it’s not here it’s ok. Our marriage, friendship our love has never been the same I blew up our life. We love each other no doubt but our relationship is no the same fear it well never be. We have a stressful life, we own our own business raising 3 kids we work hard long hours I find escape threw many things one like sex, cross dressing, kinky sex cross dressing, lite S&M etc it lets me escape my stressful life to be almost out of body place in my mind. All I desire is to do with her ONLY, never wanted to cheat, fulfill my desire with her even the crossdressing her using a strapon when I dress the part. She find other things for herself, her not know exactly what they are cause she says she has no need to escape or what do I have, she has more than she will admit. Seem for me it’s more of a desire now cause of all my extra stress with our marriage and life together. I have read and read and read all I can to yes find a cure and now I know there isn’t one, but what you said in the atricle for me to accept me is the most important. I can’t even do that, I try hard to hide the desires for all my sexual desires not just in crossdress, slipping on a pare of nylons before work,, LOL so funny and turnon, but NOW I get so humilated and ashamed of myself for even thinking it.
How do you accept who you are, when you can’t be who you are?
I looked at it as something my wife and I could share my deep dark feelings, secret I could share with her, I feel could be the who, the what I am with the one who loves me for ME not to judge but to be loved and HELL have some fun with her with us.
It all blew up in my face…
the word Ashamed is not enough for how I now feel now, the day I remember well when she first found out
“Dressing up in lingerie I CAN’T do that with you, I just Can’t” with a snarl on her face a sense of being repulsive, I never felt so humiliated in my life.. she can’t approach things very well. When I told her about my bisexual side in the years before her, I should of told her to give her the choice to be with me or not.
here we are some men trying to pretend we are women, a fantasy in our minds and hearts, bringing out the feminie side of ourselves for all the reason in the world…. But we can’t figure out a woman. we are mostly humiliated and ashamed when our wife can’t figure out the WHY we do it,,, why it’s enjoyable for us… we can’t figure out them either but we are trying to be a woman like them,,, over all it’s really funny LOL
the hurt and shame I feel now because something I would enjoy, have fun with to share a deep desire with the one person in my life I thought I could, my wife, would she even find the laughter, see the fun and joy I would receive and share with her. But my desire just became a curse and it just got worse by confiding in her. I still have strong feeling of wanting to cross dress share with my wife sexually how do I make that go away. As a man, husband and a friend I could of pick a much worst part time hobby
shame fully me