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

  2. I’m a sissy since i was 5 yo i’m start dresding with My mom and My sister clothes and My mom lingery and i.nevet Say nothig to My mom because i was afraid and in México was very homofobic in that times and never been hormonize and i’m alwas be have in a cirgury to chenge My frce in to a womens face and My body and have boobs anda beautiful ass but now i’m 48 and i don’t know how to make up and still look like a boy can You help me to look more femenin and look pretty and femenin

  3. When the feminization and first time.out,. In my case, I always wanted to crossdress. My wife only word no.
    My wife and her caregiver, she had a broken toe. They planned a Halloween three days get together. Friday through Sunday. Three couples
    Thursday after work. I was ushered into the bathroom. She told me to strip.. Now you have what you wanted. I’m your dominant mistress and your my submissive whatever title I want wife, girlfriend.
    She placed me in the shower. Got my body wet. She then told this would be last time I would have any male body hair. Ten minutes later totally bare.
    She said,(” I’m glad, you have same size feminine body as mine. You can share my wardrobe. Think of all the nighties you bought me.”)
    Lavender panties with maxi pad to make it more feminine. She slid them up my legs. Push my penis down and the pad held it. Padded bra pantyhose, Blue pants suit. Then makeup And finally blond wig.
    I look in the full length mirror. No.sight of any manhood
    She said How do you like the look Katie. I guess that’s my new name.
    I was handed a black purse. Car keys, wallet, cards and lipstick.
    She told me a Walmart.list is in your purse. She opened and handed it to me. I made sure I could read it
    Six items. It covered.the whole store. Don, Lucy’s husband will there.
    Carla said I wouldn’t be able to recognize her. It’s Donna now.
    I left got there. Took a basket from the parking lot. No interaction with cart person.. Started on.list.
    The clicking of my heels was annoying
    Then from behind, (“Katie you’ll get use to it.”)
    I turned around and, I said, (” Hi Donna,”).
    We talked she.has been doing this six months. Donna thought my voice was better than hers. We went shopping like two girlfriends.
    Paid for everything, got out. Donna said,(” One thing, take your lipstick out and compact out. Put more on and then you can go.)
    Got home I thought 5pm home and now home again 9pm. Feminized, dressed and out in public.

  4. I’d totally enjoy having a girls day at wall mart.. you’re soooooo lucky!

  5. Well, why will readers be so surprised at this after all all, all men on this planet start their life as female and then a few get converted to male for the sole perpose of procreation.
    Now, you not accept this so ask yourself these two questions, (A) why doe men have nipples we do not feed babies, (B) why is it that men can catch and die of breast cancer. It is that bit of female that we start off with that is in all of us in varying degrees and that is what governs who we are and what we turn out to be.
    Education is what is needed so that a better understanding on the male condition in all its forms cant be understood by all.

  6. I love dressing like a women, i love bra ,gaine , pantyhose, dress and i go in the street like this.i go to the lingerie shop and buy lingerie

  7. Many years ago, my wife, out of the blue, started to put some makeup on my face and dressed me in her long slip with a towel covering my short hair. Then she took some pictures. Another time she painted my toenails red. They were red for 2 weeks – she didn’t know it but I actually touched them up where needed! She never did anything to take the polish off! Eventually, I unfortunately did this myself. Whenever she sees men dress up like woman on TV, she always laughs at them. I think that the cross dressing, etc., turns her on! So these stories that we are reading actually could be real!

  8. If I could only become a woman – even, a wife for a Daddy! I so want that! I will be a good, obedient woman for him, and make him so happy and satisfied! Even his sweet taste in my mouth is so sweet and delicious! Oh, simply to be in a pretty dress and panties for him, make him moan and groan in the evening, feel his kisses all over me – I so want that. Won’t someone help me with this? I will certainly try!
    Miss Roxanne Lanyon

  9. You are so lucky.I don’t think my wife would do that for me.I have wanted to crossdress for a long time.Thanks for your story and good luck

  10. I can’t remember a time when I didn’t crossdress. I used to ply dress up with my sisters and always wore the girly clothes. My mother noticed this and turned a blind eye to it, she came home one day when I was a teenager and found me in her bra and panties, she just said ‘they’re mine, take them off’ and walked out of the room. A couple of days later I found some underwear, a dress and shoes in my bedroom, along with a note saying ‘these are yours, you can wear them anytime’. At first I wore them in secret, she knew. Then one day she said put your pretty dress on and come downstairs, when I got there I was confronted by almost every female member of my family, not one of them batted an eyelid and they all treated me as if it was perfectly normal.
    After that, at every birthday or christmas there would be a couple of girly gifts for me, it’s been over 50 years now and my female side is just as important as my male side, with much prettier underwear!

  11. I have thoroughly enjoyed my life living as a woman since my teen years. One of my aunts that I spent a great deal of time with, got me started wearing some of her clothes. I started with panties, stockings and garters and a bra. The usual simple items at first. As the days past she let me wear skirts and blouses and sandles for a while. I felt so wonderful I didn’t want it to end, I told her. She took me shopping a few weeks after I started dressing in her clothes and bought me a number of my own items in ladies clothing.
    She did my makeup perfectly, as well as my nails, both finger and toe. I was slowly converting to a young girl and loved every minute of it.
    I made up my mind that I was going to dress as a girl or woman as I got older, for the rest of my life.
    I have my late aunt to thank for my changes and for helping me to be happy.
    No regrets.

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