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Swapping Clothes With A Girl

I was around 8 years old, and a friend of mine came over, along with his sister. They just lived down the street from us.

My friend's sister was wearing a strapless blue girls dress (the top part of the dress was elastic to "hug" your chest and hold the dress up), and my friend, my brother, and I were all just wearing usual boy clothing - T-shirts and jeans.

We got the idea to play dressup, and we thought a funny idea would be to swap clothes!

My friend swapped clothes with my brother. That just left his sister and me. I had to swap clothes with her.

I remember pulling on her dress up to my chest, it fit a bit tight, but an exciting feeling ran through me.

After that, I went to show it off to my Mom. She was inside the house, talking with another woman, an old friend of hers who was also visiting.

I showed my Mom and and my Mom's friend what I was wearing. My Mom's friend said, "Who is this pretty girl?"

My Mom just smiled in approval.

I spent an hour or two in that dress, playing with my brother and friends. Then, we had to swap clothes again when it was time for my friends to go home.
jennie20000 jennie20000 36-40 13 Responses Dec 30, 2011

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What a lovely story! Your mom is wonderful.

So you put the dress on, what about her panties, did you swap those as well?..

I love this story Jennie and I love your mom's reaction!

were you able to swap again? soon? did you nice mom ever get you your own clothes? many questions lots of time..anxious to read more soon...i can only wear misses clothes and feel right....peace to you,girl

It is wonderful to have an accepting and approving mother. I hope she got you some of your own girl clothes soon afterwards?

Love this experience.....warms my heart reading it.

Jennie, I know the feeling. I think my mom wanted me to be a girl. She told me on more than one occasion that my hair would hold a curl but she never acted on that after my first curlers at age 5, and I was too embarrassed to ask her to put me in curlers, as much as I wanted to.

Very nice story. What a wonderful experience. I would love for that to happen to me. I did have a transsexual escort dress me up as a girl. She did makeup, wig, earrings the whole transformation. It was exhilarating as was the sex with her while I was dressed girly!!!

Awesome story. So how'd you feel? Was that your first cd experience? Kinda sounds like domething I done.

Nice story, dear. Thanks for sharing.

I know my Mom had wished I was a girl... However, the most she ever did was to playfully mention I would look good with ribbons in my hair, when she was giving me a haircut! (How I wish she had "made good" on that playful threat!)<br />
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Like many others, I secretly dressed up in my Mom's clothes (until they no longer fit me) many times in my tweens and teenage years. I'm sure this clothes-swapping dressup event with the girl down my street was one of the things that "inspired" this!<br />
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I love women. I think my own particular love for crossdressing comes from a deep love of females, and somehow that relates to wanting to be "closer" to them, by emulating them in some way.

Your last statement says it all.....

Did your mom make any comment after her friend had left to you?