Beautiful crossdressing memories

We all have those certain moments in our lives that are permanently etched in our memories. I remember exactly where I was and what I was doing when I heard about the 9/11 attacks and the assassination on John F. Kennedy.  I remember what my kindergarten teacher looked like and what I wore at my wedding … you get the picture.  As a crossdresser we also have many etched memories. For me, pink roses will always remind me of the first time I tried on my sister’s panties (which were white with little pink roses) forever starting me on my crossdressing path. White sweaters remind me of the first full outfit I wore … my sister’s grey skirt with a white sweater and nylons.

So many of our memories are about learning our way.  So much to learn about clothing and makeup an womanhood.  My first wig was long and blonde and cost me $18. The lady at the costume shop gave me a deal, assuring me that a lot of the ladies at the strip club down the street also bought that wig. I remember my first time out dressed and in public … a blue dress with black pumps a little lipstick and a scarf in my hair (the $18 wig snarled so badly I couldn’t comb it!!) I went to the mall and had lunch at the Skippers Fish & Chips, ignoring the whispers and pointing by the counter staff.  This was quickly followed by the terror of my first public women’s restroom visit after drinking too much iced tea!!

We also have memories that are not so fond; memories that reinforced the shame we felt for what we do.   Like the look on my brother’s face when he caught me wearing only my mom’s panties; or the little boy in the checkout line pointing at me and asking his dad why that man has a dress on (coupled with the dissapproving stares from what seemed like a thousand other customers). I have fortunately never been physically or verbally assaulted, but I know many of us have.

For me it has been a long journey with still farther to go. I am at peace and no longer ashamed of myself for crossdressing.  Some of my most horrific experiences, like being clocked by the little boy are now humorous side trips along the way. I cherish those wonderful people along the way like the young lady who did my first make over at the Sephora store (telling me her dad was also an engineer!!). The most important thing I’ve learned is that I will never be seen by everyone as the magazine model perfect woman but I can be happy just being me. Keep making and enjoying fond memories!!


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    Claire Mueller

    I came of age in the 60s and have been cross dressing (on and off) ever since. Over the years I got married, raised two kids, became a scout leader, a hockey coach and a successful engineer mostly to deflect any suspicion of my other passion (although I wouldn’t trade any of those experiences). Now that the kids are grown I have more time and opportunity to dress and venture out. I live in Alaska. .. America’s largest small town.

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    julianne w' class='avatar avatar-64 photo' height='64' width='64' />
    julianne w
    7 years ago

    my memories have really been brought back to the surface since joining CDH they are all good one because I have never had the courage to venture to far .I doo remember the feeling of putting on moms nylons at 5or 6 and how that feeling at 14or 15 was rekindled when I found a copper satin dress in a closet that belonged to my sister in law I wore that dress many a time while home alone and the time I barrowed a teddy from my now wife before we were married .I have 2 wonderful memories of being… Read more »

    Danielle Lisbeth
    Danielle Lisbeth
    7 years ago

    Ahh …. such wonderment, or pain,
    when memory comes to play,
    The grayness makes for softer rain,
    and sadness wash away.


    skippy1965 Cynthia
    Trusted Member
    7 years ago

    Dani! post this in the poets corner! please!

    Sara Thomas
    Sara Thomas
    7 years ago

    Love your article very much brought back a lot of memories I always wanted the dress of the woman fantasized about it all the time but never acted on it. Then one day with my second wife we’re in bed and having pillow talk. Then we were talking about her sexy silky nightgowns bra and panties how good they feel. Then my fantasies started to become reality. She has me but I like to try on one of her silky bra and panties and I jumped at the opportunity. I thought I died I went to cross dressing heaven lol.… Read more »

    7 years ago

    My first memory is dressing up in a 2 piece binki that I found. Of course I had to seek it in the house to wash it. Lol But once I did I would go off into the field down from my house and put it on and walk around. =) I never got caught but I did think at first it was wrong to dress up like that. Then the next time I tried I was a senior in high school and we had dress up for school. Couple of my friends got me to dress up and so… Read more »

    Lauren P.
    Lauren P.
    7 years ago

    Great entry Katie! Describes so well how the memories we hold close to us can be both our best friends and worst enemies. I am sooooo thankful that life has, thus far, given me more good memories than bad. Cheers to all, and I truly hope in the days to come we all create memories we can look to and smile!

    <3 Lauren

    7 years ago
    Reply to  Lauren P.

    Hello my first time to cross dress I got a dress from my sister cut it off short . fixed my hair are pretend to be a cheer leader

    7 years ago

    That is soo true the memories of the first time I tried on my sisters pantyhose when I was 12 years old and the feeling of it. Even the struggles of being caught and beat up. I think it makes us stronger girls. I think that we have all had some of the same struggles to become what we are today. The feeling of being free and alive. Following our true femme side

    Julie' class='avatar avatar-64 photo' height='64' width='64' />
    7 years ago

    I dont remember my 1st time wearing pantyhose, I was no older than 4. But just recently, 50 years later I have discovered the joys of wearing a bra and putting on lipstick. I now finally plan to go into this fully including taking hormones. Thanks for your support

    7 years ago

    I remember wanting to play with the girls growing up. I married young and my wife asked if she could dress me sometime. I resisted, but wanted to all along. I finally agreed. She said she wanted me to know what it was like to be a woman. She dressed me completely, bra, slip, hose, makeup and even polished my nails. I loved it but didn’t let on that I did. We did this several times and I was enjoying more each time and she knew it. She started buying me my own dresses, heels and makeup and wanted me… Read more »

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