Are You Ashamed Of Being a Crossdresser?

Are You Ashamed of Crossdressing? 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,

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.

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About the Author

A woman living in Seattle, enjoying the freedom to be who she is every moment of her life!

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  1. Lisa Kaufmann says:

    As others have said, I too am not ashamed about being a cross dresser. I rather enjoy it. Since I last wrote I still have not had many chances to be Lisa but am being allowed to wear all kinds of items and purchase more and more woman’s clothes. I can wear them around the house and out if it is just me or her & I so acceptance is getting there and gradually Lisa may even be able to be around more often. One can only hope.
    As Marilyn said it is nice to be able to wear panties and panty hose many days. It has gotten OK for me to wear pantyhose and shorts and sports bra and t’s when I walk outside as part of my exercise program. To me it is not sexual but being to express myself as many others are allowed to daily. I do wear panties and hose many days under my womans jeans and tops.

    • raph says:

      Since taking crossdressing seriously, wearing tights and a skirt most of the time, almost every day, the habit has become entirely natural, dressed to feel comforatble, while looking as I wish to look. Already reported, a collection of home-made lined pencil skirts and dresses in tough velvet answer my needs. I soon discovered a skirt must be worn over tights for correct movement. An initial sense of shame, dressing as I feel comfortable, has now evaporated. After several weeks, perhaps months, of preseverence, the novelty may have worn off but the pleasure has increasingly brought the greatest reward. Just persevere – and allow the normality and sublime pleasure of the experience gradually to take over. No more shame once a skirt becomes obligatory.

      • raph says:

        To add to the above, when wearing tights, heels and a pencil skirt or dress continuously at home, the practice quickly becomes totally normal. Indeed, high heels, broken in, are surprisingly and delightfully comfortable, so much so walking in them becomes completely natural! The thrill of crossdressing really is the reward for perseverance – no shame whatsoever. If doubts arise, advice is simple: get into a skirt, tights and heels and just don’t take them off – live and love the experience!

  2. john says:

    This has been very insightful to me and at the same made me cry, I have done some form of cross dressing since I have memories, I have been in the military and have been anything but a manly man many times, but love enjoying being very fem behind close doors, I am blessed with a soon to be wife that loves me and accepts me for who I am. I have hated myself and almost committed suicide due to my mental stress on myself. I hope others find someone as good as my wife ” soon to be ” , I their life to help them understand there is nothing wrong with this and what doesn’t hurt anyone else should never matter.

  3. I am not ashamed of being a crossdresser since i like to wear dresses, skirts, leggings bathing suits, high heels nylon stockings, panties, bra’s, blouses, anything feminine i started crossdressing since i was 10 years old, and i still do that is aqll i wear now is womem’s clothes from head to toes, i consider myself as a transgender female.

  4. yulisa says:

    I do not feel embarrassed at all by dress in my stockings sexy garter and my bras, my wigs blondes and brunettes, I enjoy every day that I do, of course hidden from my wife, I even show in Youtube videos where there are many that we expose ourselves discreetly.

  5. Jenna says:

    Embarressed? Not at all. I have only been crossdressing for a few years but over that period of time I have felt myself grow more and more into being more femme. Somewhere along the line I couldn’t keep it bottled up inside of me any more so I had to tell my wife about my desires. There was of course the initial shock when I told her about Jenna, but that seemed to blow over quickly. We were laying in bed one evening when I told her that I would like to dress more feminine. She jumped up out of bed and almost angry asked me if I was turning bi or gay. I explained to her that I just have this urge to start wearing women’s clothes. The conversation didn’t last all that long and we both fell quickly asleep. In the morning when we got up and started getting ready for work, she handed me 3 pair of her panties and told me to wear a pair and see if that is what I really wanted. After showering, i got dressed and did wear a pair of her panties to work that day. I did feel a little embarrassed about putting them on in front of her at first. All day long I felt GREAT. I felt like I was finally feeling like who I wanted to be. After that day, things were a little touch and go. Each day, I wanted to be more femme in my attire. At first when we went shopping for her, I told her that I would like to buy something cute for myself but that rubbed her the wrong way. As time went on, she began to let me buy an item every now and then. Now, when we go to VS or The Gap or Old Navy, she always tries to make sure that I buy something for myself. I always dress very casual and there is nothing sexual that has me crossdressing. Usually I will buy some cute short shorts or a mini skirt or some cute underwear from Victoria’s Secret. It doesn’t embarress me at all to walk into a store and buy something for myself either. Although I haven’t gone shopping enfemmed yet but often when I am looking at women’s clothes in a store, the sales person will ask me if I would like to try something on. It makes me feel kind of good when that happens because then I know that being a little girly is ok. I have gone out fully dressed a few times but it was only to go to the bank’s drive-thru or like a McDonald’s. Couple of times I did have to stop and get gas while out and when I was pumping the gas, no one seemed to notice that under those cute girly clothes was actually a guy. So really just to sum things up here a bit, as time goes on, the confidence goes up while the embarressment goes down. I know I can’t give up dressing pretty so therefore, I just have to keep trying to do it better. There is always room for improvement.

  6. Cherry says:

    Ok for me, a mid 30s cross dresser with a wife who knows about it and barely tolerates it even a little, I wear lace panties, thongs and gstrings and thigh highs, paint my toes and use perfume, but I’m forced to do it alone unless I am so high I don’t care what my wife says, and I go for it. She used to be more patient even using a dildo on me sometimes but she became disgusted at a certain poi t and that stopped. I feel guilty cuz I also crave cocks and she knows I’m bisexual, I should say I look ugly in a wig so I will stop at the waist usually and I am still Cherry,

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