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
—
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.








i to have felt guilty about crossdressing and i have tried to stop but it looks like my marriage is over because she hates it espeshally when i go out side ,iwish it didn,t have to be this way
I’m not ashamed of being a cross dresser and I not ashamed of doing things that make me feel good. Every one does things that are partner does not like and there are things we just can’t stop so instead of hiding it from are loved one’s we tell them. Now if they wont to join in with us it is up to them. Every one need there own privet time. So as long as I’m not out hurting anyone or changing this world give me and give your partner there free time to do what ever they want as long as it does not hurt anyone thank you.
I couldn’t have said it better than Michelle. She mirrors my feelings precisely. At my particular time in life though, I have finally quit beating myself up over it. I keep it to myself, dress as I need to, enjoy my time with it and then put things away and forget about it until next time. Works for me.
jessica i also feel guilty i am a closet cross dresser i have always had this feeling that i should of been female but iam married have kids no one knows and prob will keep it that way when i dress up i go what am i doing but it feels right so i just keep what i am doing
I was raised Catholic so you maybe can imagine the guilt I had through the years. The buying and throwing away almost drove me wacky. Then in 1989 I had a huge life changing experience when I almost died from cancer, after which I took on a totally different outlook. After I had recovered from all the Chemo, Radiation and Surgery I realized the desire to dress was as strong as ever. It was then I realized that what I wore and how it makes me feel has nothing to do with what happens at the end of life, it pretty much evolves around what we have done for others. I have not suffered the guilt since then. I now have a small wardrobe that I keep, and my wife has even come to realize the same thing. It’s a pitty a guy has to almost die to get a little peace, but I believe it was all for a purpose and have come to embrace my crossdressing. There is nothing else that relieves stress and anxiety as well as a nice snug pantygirdle…:-)
I only partially cross dress It gives me a feeling of peace and wellbeing. I started with my mother’s stockings at age 9.I find it hugely relaxing and I do really envy women.I would describe myself as asexual, perhaps with lesbian and submissive leanings.Am I confused ?. Yes very much so.
not ashamed at all,iv’e been moer or less dressed as a girl for a bunch of years,now,why change?
Well as most people here I have been ashamed of it almost my whole life. I have finally come to terms with it and do feel much better about it. It may be strange but I feel a certain comfort when dressed and less stressed out. But what is it all for? It can make you feel very lonely and isolated. No matter what I’d do to stop doing it it doesn’t work so I quit trying to quit. My girlfriend knows and said she doesn’t care but I know she does and it kills me. It sure would be nice to have friends with the same interests
I been cross-dressing for along time. Maybe almost 20 years (or since I was about 5 i guess).
For ages I was conflicted about it. I actually thought I might be gay because of the cross-dressing but recently found out you can be completely straight and crossdress.
I didn’t really start telling anyone about it until I finished college. I started to buy alot more girls clothes. In fact I probably own more girls clothes than guys clothes. I usually shop at thrift shops because they have large variety of styles at super cheap prices. I am really proud of my collection. People don’t really care when I stroll up to the counter to buy a skirt or top or heels etc.
I also have a bunch of make up now and being in to art, its kinda like drawing and painting on your face. Very creative really. There are hundreds of make up tutorials on Youtube.
I love being able to express myself at partys all dolled up and people always comment and say how awesome the make up is and wonder who did it and where I got my shoes etc.
Ryanna,
I think my girlfriend sort of thinks the same thing, she sort of doesn’t care, but I know she would much rather I wasn’t in to it. But I suppose if she goes to a football match wearing guys football uniform then that’s kinda cross-dressing too. In fact when ever I see women in pants I kinda think, hey that’s cross-dressing. I sound sexist, but I think it sucks that guys are really restricted in what they can and cant wear etc.
I quit cross-dressing for a while but realised I just loved doing it too much to repress it. You only live once as far as I know.
I keep doing it because I get a buzz out of it. It make me a happier person and you can’t buy that (happiness).
However, you can pick yourself up a tiny plaid pleated skirt that will always lift your day
)
I must say like most I (had) the same guilt my mother even told me one time that she prayed that I would feel this and change but that did not stop me well maybe for a couple of weeks it did just before her passing I sat down with her and had a hart to hart talk with her about my feeling and why I do crossdress she understood and changed her ways on top of that when I meet my wife before we went out on any date I told her that I am a crossdresser but at the time only put on nylons well after 5 years one day I got totally dressed up as a street hooker for holloween and loved it all and told my wife how I felt and she was 100% supportive helped me with everything when my kids turned about 16 they found out and were also just as suppotive I cant tell you all how much that support from my family ment to me that type of a woman is one very special person who I loved so dearly untill her passing in 2002 I so much miss her love and open hart and loving me for me .. Yes I went throuight trashing everything 3-4 times hoping that would be the end but no it was not and yes it does get expencive starting ouer again I will end with this I have noticed over the pased 5 or so years that women are now more to except it then 10+ years ago and when you do find that one hold on tight and don’t let her go she is one SPECIAL lady .. Rest in pease my Love we all miss you Jeanie .. xoxoxo .. Your Love Jackie :0
I’m not ashamed of who I am, yet I am respectful of friends and family. My significant other, tolerant and ultra liberal in so many ways, loathes cross dressing. Because of that I dress only when she is away…. Lately I have felt more drawn to my dresses, heels and makeup and as a result, more lonely in that I have no one with whom to share this wonderful experience. Websites like this one are a godsend to those of us who derive such a feeling of inner peace and wholeness from such a simple and harmless activity.
I have finally told my wife about my crossdressing. The hardest part was admitting it to myself and I feel a weight off of my chest. The hardest part was coming to terms with it myself. I am still not confident enough to go out dressed or raise with other family members bur happy have done so with wife.