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I Remember My First Crossdressing Experience

First Time Wearing My Sister's Clothes

By: deleted
Written on August 25th, 2011
By: deleted
Age: 26-30
4,061 people have read this story

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5 responses
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    Melodie13

    The dresses and pantyhose next will give you a bigger thrill, but do it early in the day so you can enjoy more then a few fleeting minutes. Walk around the house, make something to eat while dressed. Watch a little cable TV. Experience the day in a dress. If you like it then decide, you will need to get your own things and can get them inexpensively from the nearest thrift store like Goodwill or the Salvation Army.

    Jun 8, 2012
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    suelip

    I started dressing in my sister's clothes when I was 11, 36 years of pure happiness. I must say, I did get caught a few times as a teen by my sister while in her clothes or going through her dresser. She wrote it off as a teen going through puberty. Till recently going through my divorced, I came out to my family and friends of my lifestyle. My sister was very surprised I still dress and we have had some long talks on it.

    Jun 8, 2012
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    roxanna105

    lovely story you now know you have a feminine side so explore those emotions and accept them gladly

    Sep 7, 2011
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    heather69

    Yes I will never forget the very first time I crossdressed. I was 12 years old and on one of my winter breaks I found myself home alone. I finally got up enough nerve to go into my mom's panty drawer. I was so amazing at what was inside of there. I grabbed a pair of red, silk, bikini cut Victoria's Secret panties. I rushed into the bathroom and I put the panties on. After they were on me I felt so amazed. The soft satin felt so cool and comfortable against my skin. After that every time I got a chance I would try on other pairs of her panties and dresses and bras from her closet. I never got caught doing this.

    Sep 1, 2011
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    CDralph2010

    Sure did read the whole thing, and welcome to the family! I'm both excited for you because I remember my first years of discovery about the same age, and terrified for you if you're still doing this at home and still getting into your sister's things. You stand to lose so much if you get caught -- your sister's trust in you being the main thing, and your relationship with your parents could suffer (or improve... not everyone has parents who freak out at discovering their son is different).



    So that was... what, 4 or 5 years ago? What has changed since then? If you're like me (and a lot of us), you've probably had a tough time getting a handle on just who and what you are. Remember, there are no wrong answers and no matter what anybody says, there is no required "next step". If you're happy with just the panties, great... if you also like dresses or skirts, fantastic. If you want to try passing as a woman... good for you, but be VERY careful; men don't pass as well as they think they do and most of the world gets really angry at finding out they're in a live reenactment of "The Crying Game".



    You don't have to act like or think like or feel like a woman if you don't want to; plenty of us just like the clothes and are happy still being all man under the satin. Conversely, you also don't have to stop at the dressing if you do feel like you need to find your inner female. Just take a long look at yourself and what you like and don't like, and go with what's right for you.

    Aug 25, 2011
    3 likes