Crossdressing Stories

My Journey

My Journey - crossdressing story

My name is Rebecca. I started out this journey when I was 9 years old I’m now 49, well almost.I was adopted when I was 5 and always knew and I always felt different. Like all the other stories I hear it seems like Mom and Sisters are the sources of the trial. The story is the same with me.

When I started I was young enough to have the benefit of soft skin so dressing was easier and so exhilarating. I felt so incredibly sexy and beautiful. But I also felt alive.

I started needing to do the extra work of grooming around 13 and would secretly wear panties and pantyhose under my boy clothes in school and at work. When I was 16 I started to buy my own dresses, heels, under garments and hosery. I also would snatch a pretty outfit or two of my mom’s. Dressing in private.



When I graduated from high school I started venturing out to the airport, it was obviously before all the security changes. I loved people watching and airplanes. I would walk through the concourse. So incredibly excited and nervous. One or two times maybe more catching the eye of a few men and women. I actually had a woman come up to me confessed she knew I was not a woman but thought I was gorgeous and kissed me among other things.

It was such a turn on. But then one day I ventured out to a drug store by my home. I looked amazing. I made it through the store no questions asked. Then I got back home. That changed everything.

When I pulled into my driveway the very beautiful girl next store caught me trying to get in my home undetected. She asked me to come into her house and we talked about me. She kissed me and touched my freshly shaven legs and went up my skirt. She was my special friend afterwards for a few years.



After that, moving out of state and two divorced. I now live as Rebecca full time. Looking for that special girl. Sometimes fantasizing about being with a man. My parents found out and both exes know. Being accepted as me by a woman would be awesome and a dream come true.

Sent by  Rebecca Sweeney

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