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Finally Telling Someone

Finally telling someone Crossdressing Story

I have always thought that the clothes I wore just weren’t what I wanted to wear. I would see the girls my own age in their dresses or pastel colors and wanted to wear that also. This thought and, later, had become a feeling, and a desire.

Like a lot of us, I had an older sister by 3 yrs. I would often wear her clothes. First panties, then panty hose. .I became a usual thing for me to do. Then came the bra, the half slip, and then the dresses and sometimes slacks.

I used to love looking at myself in the mirror. Twirling in a skirt, walking sexy in a sundress. I loved it.

I started to go to the store and buy my own things panties and dresses and , well , anything that I wanted to make me pretty. Now that I think of it I used to tell the sales girl it was my sisters birthday and it was what she wanted…..(my sister had several birthdays all year long…wink wink)

As time went on, no one knew my secret that I know of. I was happy in secret all by myself, being myself. Then I met Debbie.

Debbie lived across the hall from my first apartment. She was a very friendly neighbor. Always polite. And she was rather attractive. When ever I saw her I always thought in the back of my mind…”I would love to wear what she is wearing right now”

Well we became good neighbors and then friends, we would have drinks and dinner at each others place and have a great time all the time, watch tv movies chat and stuff. It was great.

The whole time I would spend time with Debbie, I was always wearing panties and sometime a bra under my clothes. I was quite good at not letting anything show. One night we were watching tv and a show called “kids in the hall” came on. I knew the show, loved it. Debbie asked if I thought the guys in the show enjoyed wearing women’s clothes. the conversation went like this….

“How would I know” I said

“well they are always wearing women’s clothes” Debbie said

“Well , maybe they do like it” I said

“Do you?” Debbie asked

“Do I what?!!!!” I replied rather nervously

“Do you like wearing your women’s clothes?”

I was silent. Then Debbie came close and said she knows…

It turns out I wasn’t that good at hiding my panty lines or my bra straps.

She said it was okay and I confessed everything to her. It felt wonderful to tell someone. She helped me become more of the girl I longed to be. We went shopping did make up together, she even got me to go out in public dressed up as myself. Well that is my story.

p.s. Debbie and I have been married for 7 yrs now and we still get dressed up together and go out.

The End

Story submitted by Heather

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  1. Wow that is such a great story almost hard to believe you are so lucky

  2. Lovely

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