My heart is beating strangely, I’m feeling sad and I want to cry for no apparent reason. I’m sitting here thinking, and wishing, that my outer self matched my inner most desire.

I have what most would consider a good life. Married to a beautiful wife, the father of two wonderful children, ages 13 and 11. We have had 14 years of happy family life. Yet, since I was young, I have been interested in wearing women’s clothing and makeup. Now I am still attracted to women; I just also happen to like wearing their clothing and makeup. I never got a good chance to dress in my younger years, however, since I’ve been married, I’ve been able to dress a number of times.

One time I cross dressed in front of my wife with her clothes just for fun, and she found out. She wasn’t exactly happy about it, but after I took the time to explain to her about my secret “hobby”, she finally accepted it. After that, I’ve cross dressed as much as I’ve gotten the chance.

However, I have never been happy when I looked at my appearance in a mirror after cross dressing. What I saw was totally different than what I expected. I looked like a man wearing women’s clothes and that’s all. I did not look like a woman. Now I am over 40, and I was 77 kg (170 lbs.) with a 40 inch belly and short hair. I thought that’s possibly why I didn’t really look like a woman, so I decided to lose some weight, and grow my hair out enough to look more feminine. Three weeks after starting my project, my body weight was down to 73 kg (161 lbs.), I lost some inches from my belly, and even my face took on a bit more of a V shape.

Last Saturday, my wife and children went out of town for my wife’s family’s charitable activity. I didn’t accompany them and was home alone for two nights and three days. Luckily it was a weekend, and Monday was also a public holiday. Moreover, my wife had just bought some colorful blouses, as she got a good price from the fashion shop. Lucky me.

After they left home, I closed all the windows, locked the door, switched on the air con, and had a shower. Then I started by putting on a bra first. I cleaned my face, applied foundation, then powder. Drew in my eye brows, put on some eye liner, fake eye lashes and finished my face with some lovely pink lipstick. Combed my long hair into a feminine style and fixed with hairspray. Wore a waist cincher, then dressed in a colorful floral patterned blouse and a long black skirt. Put on earrings, a necklace, a golden ring and a gold and diamond bracelet on my left hand. Finally I placed some women’s sunglasses on my face, put on a pair of heels, a slim bag on my shoulder and I stood in front of the mirror and I got a bit of a shock for a few seconds. For the first time a pretty woman is looking back at me from the mirror. And it’s me – yes – it’s really me. And at that moment I am very happy. That day I even changed into other blouses, tried on different jewelry and took a number of photos.

After a few hours, I was faced with a problem – I didn’t want to go back to my original male clothes. I really, really didn’t want to go back. It was going to be very difficult to take off the beautiful blouse and skirt and go back to my male clothing. So I decided not to wear my men’s shirt again during the three days and instead I wore women’s clothing the entire time. I have been thinking a lot about what this all might mean. I still love women, that hasn’t changed; but I find myself drawn more and more to dressing and presenting as a woman.

As a next step, I might try to persuade my wife to take a second honeymoon trip, somewhere where nobody knows us. Then possibly ask her if she would agree to me wearing a dress and going out for a private dinner together with her. I would love to go on a girls night out. And I would love to get a lot of photos for my first experience out cross dressing in public. And yet, I don’t know if this will happen.

So I’m sitting here thinking, and wishing, dreaming and imagining that one day I will be able to fulfill my heartfelt desire.

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34 Comments
  1. Tammy 1 week ago

    Hi hunnie your picture looks stuuning, I do hope that VERY soon
    You get your heartfelt dream. Iot of love xxxxxx

  2. SuzanneLeBizarre 1 week ago

    LOVED that story…and find it heart rending. Ii have been married twice )both deceased) but only my second was tolerant and accepting of my own interests in crossdressing. She had been in show business, loved costumes and makeup, and would dress with and for me IFF (there are always conditions!). I do understand the feeling of seeing myself in that mirror, dressed as I feel I should have been born. I did grow up with 17 aunts, 3 of which used to dress me in their family hand me downs on weekends…and of those 17 only 3 ever married (they were ALL afraid of men!). So, here i am, an octogenqrian now…wishing…sighs

  3. Lisa 1 week ago

    Loved your story Winnie !
    Good to hear you saw your inner self in the mirror. I wish you all the best and hope your wife agrees for the private dinner. I have so much feelings that relates to you, thank you for sharing once again.

    -Lisa

  4. Hansa sarivar 1 week ago

    I also do the same when I am alone at home and enjoy my image. My wife did not like my CDing. But she had to admit that i look much better in a lady dress. Now she allows me even willing to buy dresses for me. But she still hates it. So I do not wear lady dresss in font of her. I do not take my photos as I can not do any make up. I don’t like it.

  5. Isabelle Chevalier 1 week ago

    How deeply true and relevant this article is. I see many of us share the same thoughts …. and challenges. This fact alone is motivation enough not to let go and slide back into the “easy way out”.
    Isabelle

  6. Karen 1 week ago

    Love ❤️ the story I can identify completely especially the part about not wanting to go back. I enjoy being in fem but for me it’s still in the closet. My spouse is totally against any possible dressing at all

    Karen

  7. vvvv 1 week ago

    I want to be woman. But not have courage to out in female dress. If i get a companion who help me for Crossdressing and the mtf transitioning

    • Lisa 1 week ago

      I too feel exactly the same …

  8. Broll 1 week ago

    Thanks for sharing. I understand that stuck feeling of wanting to dress a certain way but outside stigmas or relationships may prevent that from occurring. That desire doesn’t go away. I at times feel very alone and is nice to hear from others who may have similar struggles for whatever the reasons.

  9. Jan 1 week ago

    Loved your story, it sounds like myself. I dress when ever I get a chance. It makes you feel like a different person. I think all the time of getting all dress up and going out to dinner with someone. I am also married, but my wife would never go for me dressing up. One day your dream of going out will come thru for you, beautiful article.

  10. Melanie 1 week ago

    Oh Winnie……you have no idea how much I relate to your wonderful story. I too have been married to a wonderful, beautiful woman for over 30 years now and have two lovely grown-up daughters. I discussed my need to be feminine to my wife a while back, and at first she found it difficult to accept, but after she read many articles and stories from other crossdressing husbands, has now accepted that I am still the same person deep down that she first fell in love with, but do need to express my feminine self from time to time. I too would love to venture out as a woman with my wife, but at the moment, am happy being Melanie just in the privacy of our home.

  11. Erica lynn 1 week ago

    Hi all, my fem name is Erica Lynn. I started wearing my wife panties about a year after we were married, that lasted a couple of years then I wanted to go further with my dressing. So I started wearing her bras and nylons, I felt more fem and she didnt like it and left me with the house. Slowly I would go to womans shops and buy womens things. I was so suprised that the woman helped me get my sizes and helped my with styles that fit my personallity. the I want to a shop where they taught me makeup, when they were done they told me I looked like a woman now and I loved it. when I walked around the mall, no one could tell that I was a man. then i let a man pick me up.

  12. Janine 1 week ago

    I can relate to how you feel. Although I’m single I do have a girlfriend and she doesn’t know that I’m a crossdresser.
    I know what it’s like to get dressed and take my time getting my makeup just right.
    I know the feeling of looking at myself in the mirror and seeing a great looking girl looking back at me.
    It took me quite awhile to get the confidence to take the next step and venture out so people can see what I look like.
    I know that it’s not easy to do but it’s something that you have to do and the sooner the better.
    You sound to me like you are ready to do it.
    Just take a business trip and go out of town and transform yourself into the women who you are.
    Being somewhere that no one knows you will make it easier to be able to go out dressed en.femme and you will be so elated and happy that you finally did it.
    You said that you looked great wearing your wife’s clothes.
    Buy some of your own and you’ll look even better
    Half the fun of crossdressing is buying your own clothes and seeing what they look like when you put them on
    Then you truly have you own identity wearing clothes that you have picked out for yourself
    Go to a Victoria Secret and purchase some sexy lingerie to start with.
    Buy lots of panties and bras and anything else that seems sexy to you
    It’s a great place to start building your wardrobe
    I love getting dressed en.femme and going to VCs.
    All the girls there are very helpful and go out of their way to help you find what you’re looking for
    They help many crossdressers as well as genetic girls so don’t be afraid to shop there
    I hope that this helps you in your quest to be a woman.
    I know that if you try doing it you will see that there’s really nothing to worry about.
    I wish you well as you start to become the woman who you know that you are.
    Hugs from someone who knows
    Janine

  13. Six 1 week ago

    I loved, the article and totally can relate. I feel that in a past life l was a woman, somehow some place in time. I like wearing panties, no bra but a nice camasole would do, if one knows any females they hate wearing bras! I have never felt the desire to put on make up or anything like that, just wearing under wear. What’s important is finding a partner who excepts you for you. I have read many articles and many who wear wemons clothes are afraid of being alone, but aren’t we all. What good is doing anything if you have to hide in a closet to enjoy who you are, I don’t flaunt who I am. I don’t need that, I just try to be me.

  14. Aileen Smith 2 weeks ago

    Thank you Winnie for your wonderful story it is very similar to what I have gone through. My wife as been very supportive of my new life although at times she still has her doubts.
    I have been dressing now for 5 weeks I get up in the morning and put my short satin nightie on and do my ablutions which includes shaving everywhere. I dress in my men’s clothing but with a bra, thong and tights on to walk the dog as I have told my wife I will abide with her rules which is not to embarrass her by dressing out. However I am pushing the boundaries by wearing makeup out with nail polish on fingers and toes, eyeshadow and lipstick.
    But when I am in the house I change into a short skirt and blouse after all my wife does say that I have fantastic legs. I am over weight but losing it slowly so one day I might actually get a figure. One thing about being overweight is I have a 40 inch B cup but I am going to speak to my doctor next week about the best way to increase my breast size to a Couple cup.
    I hope you get that chance on your second honeymoon to dress as you want be strong and truthful to yourself and small steps lead to huge leaps in becoming the real you.
    Good luck and God bless
    Lots of love Aileen xxx

    • Author
      Winnie 1 week ago

      Hello Aileen,
      Thanks for your comment and reply.
      It’s my really true story.
      Now I could wear a little makeup, very thin skin tone eye shadow, natural style eye brow, lady perfume for my daily office life. For other social events, I’m wearing Skinny pent and ladylike working shoe..

      hugs with loves,
      Winnie

      • Aileen Smith 1 week ago

        Thank you Winnie for replying you are a inspiration to us all I too wear perfume what my wife bought me it seems to make me more feminine about myself.
        I did get a nice surprise though the other night my wife popped out to the shop when I had a knock at the door, now I am not allowed to answer the door while I am dressed however it was a parcel we was waiting for, so I answered it and the lovely gentleman asked me to sign for it calling me miss in the process.
        I was elated even though I don’t look much like a woman at the moment. I have a goatee beard trimmed very short and I try to disguise it with Foundation and powder and with my pot belly I am far from being the good looked.
        But ladies like your self inspire me to strive harder to unlock the inner woman in myself.
        Thank you once again and well done for being you.
        Love and big hugs Aileen xxx

    • Sasa 1 week ago

      You are so lucky woman dear Ailen i my case is compltly opposite.Years and years each morning iam looking me as a woman in mirror but only in panties ,pantyhose tops and bra with small breasts but i need more and more ,As a woman i used daily my wife amd mine antiagging cream any ladies deodorantes and then i go to work as a woman with my femme soul ,partly body ,underwear and matt lipstick …. but Sasa need more and more
      hugs Sasa

  15. Shannon Fox 2 weeks ago

    Hi winnie it is nice that you have a wife that accepts you and the outfit you described sounds lovely it would be something I would love to wear.

    • Author
      Winnie 1 week ago

      Hi Shannon,

      Thank you for your comment.

      hugs with loves,
      Winnie

  16. Kim Paige 2 weeks ago

    Winnie,
    Thanks for sharing this! I definitely know what you are talking about. I find myself more and more drawn into this, the more I dress the more I enjoy it.
    Thanks!
    Kim

    • Author
      Winnie 1 week ago

      Hi Kim,
      Thank you for your comment.

      hugs with loves,
      Winnie

    • Six 1 week ago

      To be yourself, and to find a partner who excepts you for you. Is the greatest feeling, but one most be honest with themselves first, we can not live a lie.

  17. Eddy 2 weeks ago

    Great article, hope you get your 2nd honeymoon or even a girls night out. Enjoy your journey stay true to yourself Eddy

    • Author
      Winnie 1 week ago

      Hi Eddy,

      Thank you for your comment.

      hugs with loves,
      Winnie

  18. skippy1965(Cynthia) 2 weeks ago

    So glad you finally got to see in the mirror Henderson you get like inside. I hope you are able to explore your feelings and decide what you want your future path to be. I am similarly on a journey of exploration as to whether to remain as part time dressing or to go further in presenting full time and possibly even transitioning at some point. Just remember the journey itself is as important as the destination. Enjoy life to the fullest and achieve your dreams not matter what they may be!
    Cyn

    • Author
      Winnie 1 week ago

      Hi Cynthia,

      Thank you for your comment.

      hugs with loves,
      Winnie

  19. Linda mm Magliore 2 weeks ago

    Wonderful article that beautifully captures that special moment when the image in the mirror matches your image of what you hoped to see looking back at you.

    • Author
      Winnie 1 week ago

      Hi Linda,
      Thank you for your comment.

      hugs with loves,
      Winnie

  20. Leonara 2 weeks ago

    Winnie,
    Such a great article which explains the feelings and their experiences of many beautiful ladies here at CDH. Yours truly included… Your second honeymoon suggestion is very timely…. My wife and I are embarking on a ten day trip next week which may be a start for her to understand my alter ego. Winnie, I wish you all the best in your journey ..
    Leonara

    • Author
      Winnie 1 week ago

      Hi Leonara,

      Thank you for your comment.
      Your reply is a great energizer for me to write the second article.

      hugs with loves,
      Winnie

      • Terrim 1 week ago

        Winnie, I am married 46 yrs and my wife found out when we were married 10 yrs. We had 2 children at the time. We have 5 now, all grown. My wife wants nothing to do with my femme side. But she let’s me get out 1 or 2 times a month. Everyones situation is different. My keyword in my life is Balance. My family has always come first in my life.
        Huggs Terri

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