Are you ashamed of who you are?

Are you ashamed of being a crossdresser

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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Dedicated to creating a safe, supportive and welcoming environment for everyone in the transgender community.
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Latest posts by Vanessa Law (see all)

  1. Profile photo of Suzanne Jeffries
    Suzanne Jeffries 14 mins ago

    Before the internet and sites like this one I thought I was the only person in the world me. I knew I was completely “normal” in every way except that I liked dressing completely as a woman. After 23 years of marriage I came out to my wife. It took her about a year but she came to completely accept Suzanne. She went from just tolerating it to accepting it to embracing it. We now go shopping for clothes, makeup and all things feminine together. She has helped me so much with my feminine presentation.
    Now for the topic at hand. I used to feel an incredible amout of guilt and shame for dressing. It was such a relief when I was doing it but after I would feel terrible to the point that the after feelings took so much away from the experience. Over the years and especially after coming out to my wife I have come to realize what and incredible gift it is. Some of my happiest moments happen when dressed. My wife and I are much closer than we have ever been. The few times we have gotten to dress together are my fondest memories. Having someone to chat with while putting on makeup and getting dressed is a really fulfilling experience.
    I always thought the public service ads about how “it gets better” were kind of corny but my experience is that it has gotten better. For women like us gender is such a complicated issue we need so much extra empathy, love, acceptance and understanding. I hope and pray all of you will receive these blessings and be able to live a happy and authentic life.

  2. Profile photo of Jamies time
    Jamies time 4 weeks ago

    Vanessa I believe crossdressing is a blessing I have never felt so good until I started dressing and always shopping for new cloethes . Now I go to salons for makeup sessions and buying new purfumes on female mode. I get so much attention at stores from the help trying to help me. Thank you for your help also and all of the caring ladies.

  3. Profile photo of Jennifergordon
    Jennifergordon 4 weeks ago

    I sometimes have a problem with the constant urges to dress but over the years I have learned to accept it. If you don’t it will make life difficult. Acceptance makes things run smoother. Will wear my new pink panties to see my dr. Today!

  4. Profile photo of Karyn Lobelia
    Karyn Lobelia 4 weeks ago


  5. Profile photo of Hailey Loralyn Cross
    Hailey Loralyn Cross 4 weeks ago

    Yes…yes I am

  6. Profile photo of Alicia Roxxx
    Alicia Roxxx 4 weeks ago

    great read!

  7. Profile photo of JENNIFER
    JENNIFER 2 months ago

    I was ‘confused/ashamed’ about dressing up in lacy women’s lingerie for MOST of my life, but I finally ‘Gave Up’ over the last decade. Now, I wear only the prettiest lacy lingerie (usually Pink) 24/7.
    What I do ‘behind closed doors’ is NOBODY ELSES BUSINESS!! I just ‘wish’ for someone to “Play With”….

    • Profile photo of Jennifergordon
      Jennifergordon 4 weeks ago

      It’s great Jennifer! You can’t fight it! Keep me posted!

  8. Madeline 2 months ago

    Dear Michelle. Loved your article I know how you feel. I have crossdressed since my teens and often thought there may be some thing wrong with me. I am a closet crossdresser and no one knows about it. What I do know is that when I am Madeline It feels so right, it feels more natural and comfortable. I can express my self and feel more relaxed. Above all I am at most happiest when I crossdress and are Madeline.

  9. suesy 2 months ago

    im still a closet crossdressser but i would like to go out in public dressed as a gril help

  10. Profile photo of Abi
    Abi 5 months ago

    I have always had the need to crossdress. From when I was a child at home and totally fascinated with my mum’s wardrobe to now where I have stopped lying, to myself at least, and bought some clothes, underwear and heels online. I’ve since Bought make up and a wig as I want more than anything to be female. I feel I have wasted my whole life trying to be happy and male when I’m screaming to be a woman. Dressing up helps keep me real before living the lie of my birth gender. At the moment I dress is n private and no one in my family are aware of this. I hate lying to them but o fear their rejection more than any other. I need to find the organizations that can give me a full gender dysphoria assessment and diagnosis before hell n my loved ones of my true self.

  11. Profile photo of Karyn Lobelia
    Karyn Lobelia 5 months ago

    I sometimes was conflicted by what others thought . As my wife ,Shelley , encouraged me to become metrosexual and start growing my hair , I would hear comments at dinner parties like ” isn’t Shelley husband starting to look effeminate . Women stated to notice that I was wearing ladies pants , shirts and jackets and even the fact that they were in men’s styles , while their husbands did not . A couple of times my male friends would say , Karl you need to start working out and why are you wearing nail gloss – you just do not look like you use too! When my wife heard these off hand comments and said she liked me like this and loved it that I had a new style , I would hear off course she is making poor Karl effeminate because her last husband was so macho ! As I started taking hormones , I often ask at resorts with my friends around by the resort management to wear a top around the pool as they thought I was a girl since I was waxing my legs and as femme as I was I was totally EMBARASSED . and several times was crying in my room . At the pool a couple of teenage girls had their boyfriends ask me ARE YOU A GIRL ! Because I was not wearing a top and , well when I did not answer , they held me a pulled my bikini like bottom off . You do not know how embarssing that was as they starting laughing at me ! One of my wives and mine girlfriends had her husband wrap,a towel around me and carry me to their room . I was afraid to show my face for days at the pool area ! Of course until you make the transition to total cross dressing this goes on . At work I had a lot of stares or whispers ,I.e. Comments especially when I started wearing ballet flats and my nails were French nails .At that time a lot of the male made comments , I once overheard about me LOSING MY MASCULINITY , and that I was OVS gay ! and they thought management would take awkward my supervisory job and make me a secretary ! Guys in the bathroom would tell me to cut my hair or say I was in the wrong bathroom in a kidding way To Them ! When I made the transition to wearing dresses , skirts , Jewerly and heels , it was actually easier !

  12. Profile photo of Evelyn Rodriguez
    Evelyn Rodriguez 7 months ago

    OMG! I feel the same as Michelle. The only difference is that I am still single. My family and friends do not know I dress. At times I felt so ashamed of dressing that I prayed that God take my life so I won’t hurt the ones I love. Sometimes I feel that I have an expectation to follow. It is still a long road for me. Have I accepted myself? Not completely yet but I am getting there. This is my first time writing about this. I am grateful for this site. It is helping to heal and finding acceptance. Thank you.

  13. Maureen 1 year ago

    I would so like to be able to dress in what i feel like that day, like women do. I have been dressing off and on since I was 12. i spent 6 years as a single dad so it fit the moment there too. My wife does not know the extent of my interest, though i do wear girl jeans, boyshorts panties, yoga pants, I have 5 pair of high boots all flats I wear under my pant legs. I get my nails done with her and my daughter. And I have my occasional rants on how boring men’s fashions are.
    I dress when I am home alone, which seems a bit defeatist but I do what I can. I do feel guilty hiding it from her, but I don’t want to lose my marriage and my family – so i hide. I also do not want to be humiliated, have extra rules to allow me to dress. I do not make rules on what my wife and daughter wear – why are there rules on what I can wear?
    It is a difficult secret to keep and harder to tell.
    I have no idea why i enjoy dressing and sometimes need to dress, i tried to let Maureen go after i got married, and it was good for three or four years. Then she came back, I now know she will be here always. So i enjoy her when she is here, and i can let her out. She is always in my mind – so i get both my male & female view on life. For that i am lucky!
    Maybe one day, dressing for men will be as acceptable as being gay or lesbian or hetero. It seems to be ok for girls – but not for boys.

  14. I am a tv for over 60 years I was sent to shrinks to fix me while in hi school did not work was told to move out at graduation. Lived alone dressing at home and. working on passing I dated my present wife UNTILL I was 25 I exposed Jessica Anne to Rita (my now wife) at my apartment by dressing and walking into the living room I had a pink shirtwaist dress 3 in matching shoes 36b bra wig make up
    Rita a as in shock I held her and told her I loved her so
    Much and I wanted her to love both of us. I told her i have been doing this for 11yrs. We had been sexualy active about a year at the time I came out After a. Gollon of tears Rita made. A. Deal with me to not run out I must be sterilized prior to wedding and submit to over the knee bare ass whipping on requist this I did and I get it every 2 weeks and the marks last days. We then stand and hug& kiss loving
    Rita buys my clothes and I must where cuppess allinonegirdles tight at croch anytime I leave home as a. male at home I am female I never ware slacks only dresses or skirts it took time but our neighbors did get to no and accept me. I did take hormones in the 70’s resulting in a big but and Aandahalf boobs that lactated I enjoyed that with breast pumping for 5 years. We enjoy regular. Sex and I serve Rita as her girl Freind we do
    Not wish to go public with our lives. Jessica Anne & Rita

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