My second time dressed in public

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by stephiem

It was Halloween and a costume but I dressed this way to college and loved it


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When I was 10 years old, I wanted to be a girl more than anything in the world. My mom caught me in her things and told me to "never do that again". I listened to my mom, lived as a boy and didn't wear a piece of female clothing for another 10 years. When I was 21, my girlfriend suggested I dress as a girl for a gay Halloween party, I still am not sure what her motivation was but I think she was cheating on me at the time. I shaved all over and our gay friend did my makeup and hair, I looked passable. As that night progressed, I felt more and more like a woman. After the party, I tried to have sex with my girlfriend as a girl, she did not react well and we went to sleep. After this experience, I went back to living as a man and did not wear a single piece of female clothing for another 20 years. In my mid 30s, my marriage was a mess and my bisexual nature came out, I craved and had sexual experiences with men but I was still very much a man and more straight than gay. In my early 40s, something changed, I started to wear my wife's things and eventually bought my own girl clothes. I met with men in hotel rooms as a girl and had an overwhelming need to present in public as a girl. A year ago, I finally had enough clothes and enough bravery to go to the local Pride festival dressed fully as a girl. It was an amazing experience for me. Now, I am still confused about what i will end up being...transition seems like it is too much but as I continue to get older, it could very well be the next step for me. Until I am sure about that, for now, I am trying to feel happy as a non-binary/part-time crossdresser/bisexual person. I got divorced about 6 months ago for reasons that had almost nothing to do with my gender issues, the marriage was damaged beyond repair before I started dressing.

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Patty PhoseNichole Recent comment authors
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You have an amazing little figure sweetie!! Very sexy! <3

Patty Phose
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Dressing and going out is great. it’s a thrill and rush like nothing else.

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