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

x at x
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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Melanie
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Melanie

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… Read more »

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Jan

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.

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Broll

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.

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vvvv

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
Lady

I too feel exactly the same …

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Guest
Karen

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

Isabelle
Lady

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

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Hansa sarivar

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.

Lisa
Lady

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

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SuzanneLeBizarre

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… Read more »

Tammy
Guest
Tammy

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

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