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How I Became a Crossdresser

How I Became a Crossdresser

My name is Bert and one of the most embarrassing moment of my life transformed my whole life which I will cherish forever. It really opened my eyes to a whole new world for both me and my lovely wife. I have been married for over 3 years and I am a straight guy who always fancied women. But after this particular incident, I was completely transformed.

It was quite a normal day as usual. I woke up, had breakfast and took a shower. Then as I was getting ready to go to work, I heard a loud bang outside. I called my wife but she had already left for work. I got curious to check out what made such a racket outside.

I only had a towel wrapped around me and I proceeded to go the back yard. It was quite breezy outside and just as I got out to inspect what happened, the wind sucked the door closed catching my towel in the process. I tried to open the door but it was too jammed with the towel somehow.



So, here I was standing at my own backyard in all my glory and the door was completely jammed. I didn’t know what I was going to do to get out of it. Going around the front completely naked would be just to ridiculous as the street would be busy with people leaving for work. I started to get a bit nervous , standing there without any clothes on and just covering with my hands.

Then I started looking around and my eyes caught sight of my wife’s undergarments hanging on the line. I was quite nervous, so I rushed and grabbed one of her panties. I had to cover up with something as there was no other alternative. I put the panty on and just wished no one would see me like this. Then taking a deep breath, I ran for the front door as fast as I could. Luckily, I managed to get to the front door and finally inside the house without making any scene. When I got inside, I had a quick laugh and couldn’t believe what had really happened with me.

I went to the kitchen to get some coffee and for a moment I completely forgot I was still wearing my wife’s panty. I only noticed it after I started feeling a little aroused from the silkiness of the panty against my male parts. It was crazy but I was really enjoying how the panty  felt on my body.

This really got me quite curious and I thought that maybe wearing my wife’s panties was turning me on somehow. The day was getting quite adventurous and I felt like skipping work that day, so I called in to work and said I was going to take a day off because I wasn’t feeling very well.

The rest of the day, I browsed through my wife’s wardrobe and tried a lot of her stuffs. I had no idea where it was coming from but the excitement was something I had never felt before. I tried on her pantyhose, bra, some more panties and few of her lovely dresses. I looked at myself in the mirror and I felt so feminine and my whole body was experience such a tingling sensation like I had never experienced before.



I completely lost track of time and only when I looked at the clock, I noticed how long I had been dressing up in my wife’s stuffs. I put everything back in her closet and went to the kitchen to get sometime to eat. I just couldn’t stop thinking about how lovely it felt to wear those things of my wife.

When my wife was back from her work, I told her about the morning incident where I got locked out without any clothes and how I put on one of her panties to get in. She really got a good laugh and asked me if I enjoyed wearing her panties. I admitted I did. I could see that her eyes had gotten bigger with excitement as I knew she enjoyed role playing a lot in the bed room.

She then asked if I wanted to put on one of her outfits for her and I said why not. She was super excited. She took my hand and we both rushed to the bedroom. Then she started taking out all these stuffs from her wardrobe, a bra, panty, pantyhose, a lovely blue gown and a pair of black heels. She told me to put them on. I got a little nervous as this was something I had never done before but she seemed to be really enjoying herself seeing me like that.

After my wife helped me to get dressed, she looked at me and told me I also needed some nice makeup to go with the outfit.  She said she wanted me to have a full experience of being a woman from head to toe. Then she started applying makeup on me, which too was a completely new experience for me. She put on some foundation on my face, then applied some eyeliner and lastly  added pink lipstick on my lips.

She also had a few hair wigs from Halloween and decided to make me wear it too. She went to the store room and was back with a nice long hair wig in her hands. She helped me put them on and flipped my hair to one side. Then she zipped the back of my dress all the way up and I was so excited to wear a  gown for the first time.


When I looked into the mirror, I couldn’t believe it was me. She was surprised at how good I looked as well. Then she told me to put on the heels and I did. I was completely mesmerized by how I looked and how I felt dressed as a woman. It was quite wonderful and I felt totally different than my normal self.

My wife knew I was enjoying getting feminized as she could see my budge under the dress. She then held me near, kissed my lips and we both made love in the bed. It was one of the most intense love that we had ever made and she also noticed it.

After we were done, she then asked me to go in the living room. Walking in heels was not easy but I managed to go downstairs and in the living room. We then sat on the sofa, drinking some coffee and she asked how I felt being dressed like a woman for the first time and how it felt to walk in heels and so on. We just talked for hours.

She even joked that we should head out to town as girlfriends and see if I can pass. It was crazy how a simple incident completely lead to a totally different scenario and that is how I became a crossdresser. After that, my crossdressing journey started and it has been a wonderful experience since then.

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1 Comment

  1. I wonder when the strap on will come into play ?

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