Reflections in the Mirror and Realizing My Heartfelt Desire

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.

Stepping Out Secrets

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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Winnie

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I'm straight guy aged over 40, husband of a pretty wife and father for two cute children of 13 and 11. Management Level of a Medical Services Company from a country from South East Asia

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  1. Michelle Liefde 5 months ago

    Winnie, thank you! I too am in my 40s and get what you are saying. I keep trying to improve my look so I can see a beautiful woman staring back at me in the mirror. The more time I spend dressed in women’s clothes, the less I feel like putting on men’s clothes. I hope you are able to have that dinner with your wife!

  2. Heidi Louise 7 months ago

    I’ve been crossdressing for cover 50 years.
    But only cone out the closet 9 months ago.
    I have full support from my wife & work colleges.
    I go out in full female clothes on my days off .
    I have dinner dates with my wife and female friends
    I just love it.

  3. Knickerslover 9 months ago

    I just LOVE knickers. I am in knickers 24/7 365 year on year. I have over 30 pairs of full brief black(my favourite) and green knickers. I would NEVER go back to wearing the awful skank men’s stuff ever, YUK !!!

  4. Bobbie Bella 10 months ago

    I can relate to your story very well. What you said about losing weight has given me an added incentive to lose about 20 or 30 pounds. It will take some time, but looking better as a woman is a definite incentive.

    • Author
      Winnie 9 months ago

      thanks Nikki.
      I believe I’ll get a chance to live like a girl for a day in some future.

      hug with loves,
      Winnie

  5. Nikki Michelle 10 months ago

    Hi Winnie,

    Great article,

    I feel very much the same. I’m one of the lucky girls. My wife has known and supported my dressing since our dating days. 13 yrs in now. I just told her a few days ago that I must dress as much as possible and to never call me by my man name again. She loved it! She loves Nikki . We’re even doing a mock wedding in private to get married again. I’m excited to be her wife. However, I do still like to be my man self, but I prefer Nikki. I’ve never talk with other girls like me, So this is exciting. I’ve been so ashamed and confused for so long. I’m so happy to be finally accepting that I’m part girl and eff it, it’s ok. I was so sad for so long. I believe I was denying my true self. It’s so strange to be so passionate about crossdressing. So much to say. Anyway, good luck and I hope you find happiness with your inner girl.

    Nikki

    • Author
      Winnie 9 months ago

      thanks Nikki.
      I believe I’ll get a chance to live like a girl for a day in some future.

      hug with loves,
      Winnie

  6. Indie 11 months ago

    Thanks so much for sharing, we have much in common and understanding. Hoping you the best. My wife will never and I mean never even hear of it.

  7. Violet Flowers 11 months ago

    Thank you for this article. I know just how this feels not wanting to go back to male clothes. It has been a real help reading your experience. Wishing you all the best.

  8. Terri Knoan 11 months ago

    Thank you for your article Winnie

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