Crossdressing schoolgirl at school

Read Part I of My Hidden Secret.

After first dressing in my mothers clothes early in my cross dressing I began to look forward to each time I would feel the silky fabrics against my skin. I knew that it was not normal for a young boy to have these feelings but I could not stop my feelings. I began to feel more and more guilty about this but did not know where it would take me and as I began to be more interested in girls my own age I became fascinated with the clothes they wore and how it looked on them and I did what every young man did after high school I got married.

I thought that I would be able get over the urge to wear fem things and go on with life as a man forever giving up dressing.

It did seem to be that I was going to be able to overcome my urge to wear women’s clothes and live a so called normal life, happily married. However it happened again. Looking in my sock drawer I came across a pair of pantyhose that had been put in my drawer by mistake and it was just like the first time all over. No one was home and I had to try them on after all it had been a few years and I had to see if the magic was still there.

This was what started me on the road to dressing again and I could not look back. It was now more that before my hidden secret. I could not allow anyone to find out about my wearing hose; most of all my family. I started to buy my own so there would be no accidents in putting a tear or run in stockings that were not mine.

Soon I had my own heels and bras hidden away to wear whenever I was alone or when my wife went to visit her parents for a few days. I was in heaven walking around my own home all dressed up loving every minute of it. It was a very stressful time because I had to hide my clothes and keep my secret from everyone.

This was the darkest time of my dressing I was alone and I knew nothing about others who had the same feelings and who loved to dress in fem. There was some talk about the fact that some men dressed up pretending to be women but none were too convincing and society in general had nothing good to say or would certainly support anyone. I finally had the opportunity to get dressed as a woman one Halloween with the help of my wife and this is what part three of my story will be about


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I was a closet dresser for years, afraid that someone would find out about my secret. I hid away dressing by myself and dreaming of the day I could go out into the world as who I wanted to be. After many cycles of buying fem clothes and then throwing them away I finally met a few people who helped me with my dressing and introduced me to the transgender community.

Latest posts by Ricki (see all)

  1. Sunnie 4 years ago

    I got introduced to crossdressing at a young age by a family friend. I had been fishing with him since I was 10/11 years old. I was 13 and we were going to his lake house for a week for fishing. I was 13 going on 14.
    The first night, we were sitting around the campfire drinking. I was drinking beer and he was drinking whiskey. After a while I was getting drunk. I was on the second beer.
    He told me to go take a shower so that I could sober up.
    While I was showering he came in and told me to put on the clothes he laid out on the counter. I got out and dried off and grabbed what I thought were underwear, they were but girls underwear. I told him they were girls panties. He told me it didn’t matter and he gave me a beer. I put them on and grabbed the slip which I didn’t know what it was but it was soft and silky. I liked it.
    I was almost done with the beer and I was getting pretty drunk. When he came over to me and embraced me. He was a big man and I was like a doll to him. Next thing I was being kissed by him everywhere, my face, lips and neck and all the while his hands are grabbing, rubbing and pulling. I got turned on but didn’t know what to do other than to kiss him back. We ended in the bed and he was all over me.
    Then he’s licking, rubbing me and next thing he’s putting himself in my mouth. He then he was going down on me.
    Everything seemed to move fast and he then he started to make love to me. He was very gentle with me thru all the foreplay. At first it hurt but I was so turned on. I was a bit scared but I got into it. This was our first night and there were 5 6 more days to go.
    This went on almost three years. I loved to fish and he would always invite me. I liked what he did to me.
    I grew up and lived a straight for years until about 13 years ago. This friend fell in love with me. Had a good time for two years. So its been about eleven years and it’s starting to stir in me. So I’m open for anything. I love to cross dress. Good Night

  2. Kathy Jackson 4 years ago

    I love that your story shows you were able to enjoy being treated like a lady. I love that, as well. I consider myself a woman when I’m dressed and I love when a guy treats me that way, and I can be a lady for him. Special times, that I shall never forget. I hope you find yourself loving a guy again in the future. Lucky girl!

  3. Madeline 4 years ago

    Great story Ricki. I know just how you feel. Even though I have crossed dressed since my teens I felt all alone until I came across Crossdressers Heaven. You are a inspiration to many

  4. Alice 2 years ago

    Hi Ricki,
    I am Alice. I am still in closet. I have always feel, since about 10 -12 that I am a girl/woman. I have recently retired, just a few months ahead of my wife’s retirement. These few months have been heavenly for me. I am wearing my small collection of women underwear at home whenever I can, and am enjoying every moment. I hope I can have the courage, and that my wife is a bid more receptive to me dressing in female clothing.

    I have read a few of the articles that our girl friends have kindly shared here. Although I am convinced and believe that they are right, I cannot risk coming out knowing my wife. I just want to be a woman in woman clothing at home, not more. Yet, I can’t. May be this has to do with my fear and my oriental culture. It is what it is!

    I hope your Halloween will give you an opportunity to come out, and your wife will accept you. I look forward to reading it. Good luck.

  5. Jackie 2 years ago

    Ricki this article about made me cry for I know personally and first hand what you went through in the beginning to the point of buying your own clothing. There was a period in my life that after I had came out already as for the way I dressed, wearing makeup etc. and pronouncing that I was also gay that a few year’s later to try and meet my mother’s and a few other’s approval I attempted to go straight, refrain from wearing the clothes I had largely accumulated by putting everything I had that guy’s don’t wear or use into a storage unit and began dating a girl I had known for a long time. Needless to say it was a mistake and people got hurt in the process when I decided that I just had to return to the person I really was. I felt guilty, afraid, hurt and a host of other feelings but I knew what I wanted and the lifestyle I was meant to live. Thank you for sharing your story, it is one that can give many hope for they’re own lives, Jackie….

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