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Thread: Halloween Memories and the Cheshire cat

  1. #1
    Paula Paula_56's Avatar
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    Halloween Memories and the Cheshire cat

    In the recesses of my earliest memories, there was always a whisper of something different, something awry. Perhaps it was the subtle intrigue that piqued my curiosity, the way girls swirled in their dresses, donned tights, and painted the world with colors that seemed beyond my grasp. My first inkling came as a simple fascination, wondering what it would be like to slip into their world.

    From an age where innocence was still my closest companion, thoughts stirred within me, yearnings to be someone else, someone I couldn't quite articulate. Society, however, painted the path in unmistakable shades of taboo, so I tread my childhood path, wearing the guise of just another normal boy, an ordinary child. But every so often, there was a flutter in my heart.

    It was Halloween, and I found myself at a party filled with laughter and gaiety. Amid the festivities, I stumbled upon a sight that would shift the trajectory of my life. A pretty girl in a pink party dress, adorned with white tights and rosy cheeks, wearing lipstick. A simple question about her costume led to a revelation ? she was a boy. A wave of realization washed over me like a tidal wave. Dressing up like a girl, it suddenly seemed possible, an idea that took root and refused to let go.

    That Halloween night, I watched in quiet envy as that brave boy ran around, his cute outfit billowing in the wind as he played various games. The seed of desire was firmly planted in my young mind.

    I began to notice a little store at our local mall, a quaint boutique named the Cheshire Cat. It specialized in offering a dazzling array of fancy dresses for young girls. Whenever my family ventured to the mall, I couldn't resist sneaking a peek at their storefront, my longing kept secret but ever-present.

    One fateful day, my mother had errands to run at the mall. She settled me down on a bench, instructing me to wait patiently. I was drawn once more to the Cheshire Cat, its display window showcasing a dress that had captured my imagination. I couldn't look away, the dress a dream made manifest.

    I suddenly noticed movement inside the store?a woman, who met my gaze with a warm smile and a wave.

    A shiver of fear coursed through me. I had been caught, I thought, my secret laid bare for the world to see. Just as the panic began to consume me, there was a moment of connection, fleeting yet profound. Her eyes spoke a language my young heart could barely comprehend, but it was one of understanding, compassion, and perhaps a subtle, unspoken encouragement.

    However, the pull on my arm interrupted this moment of shared understanding. It was my mother, her voice tinged with sternness, questioning my presence at the store. The offer she made, "Want me to buy you a dress?" was not filled with warmth but carried a weight of judgment, the unspoken message that wanting something like this was wrong.

    As I turned to leave, I glanced back at the woman in the Cheshire Cat, searching for clues in her eyes. Was it sadness, was it sympathy, was it support? Her eyes seemed to hold a secret promise, a glimmer of hope amidst the surrounding uncertainty. The emotions swirling around me were a turbulent storm of fear, hope, and uncertainty. In that one moment, my childhood innocence collided with a world that told me I should be someone I wasn't. The journey of self-discovery had begun, and it would be a path filled with emotion, longing, and the quest for acceptance.

  2. #2
    Gold Member Maria in heels's Avatar
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    Thank you Paula for sharing your story with us. I think we all go through that and I grew up looking at the dresses on display at the Rainbow Shop in the local shopping center. There were always two window display areas available and they rotated the clothing almost daily on the mannequins. I finally got the nerve up to go inside and purchase my first dress which was a peplum waist white stretch dress that had a gold zipper that zipped from the waist up to the neck area. Yes it was the late 1970's and it was a great time of exploration

  3. #3
    Paula Paula_56's Avatar
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    Oh gosh what courage it must?ve taken to go in and buy a dress, how old were you at the time and how did you approach the sales associates?

  4. #4
    Senior Member Kris Burton's Avatar
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    A great story Paula. It evokes so many mental images - a beautifully written piece!
    www.flickr.com/people/194195593@N05/

  5. #5
    Senior Member Emily in the south's Avatar
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    Wow, what a fantastic story. And as Kris has said, very well written.
    Takes me back to my childhood accompanying my mother thru the ladies department of large department stores.

    Emily

  6. #6
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    Paula, this post really resonated with me. As I child I can remember being fascinated by the TV commercials for a local corset shop. These were broadcast as part of an afternoon woman's show on the local NBC affiliate. Years later, I found myself accross the street from that very corset shop. I so wanted to go inside, but like so many other times through my teen and young adult years, I was afraid that if I gave into the temptation, I would emerge a changed person, and that I would never be able to go back. Turns out, the fears were well founded. When I finally did enter that realm, I was changed and never wanted to go back to who I was before.
    Last edited by kimdl93; 10-19-2023 at 10:13 AM.
    Remember always that you not only have the right to be an individual, you have an obligation to be one.

    Eleanor Roosevelt

  7. #7
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    That sounds like the Thrill of going through the new Sears, Wards & Spigel Catalogs every year
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

    If at first you don't succeed, Then Skydiving isn't for you.

    Be careful what you wish for, Once you ring a bell , you just can't Un-Ring it !! !!

  8. #8
    Member LydiaL's Avatar
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    I too remember the thrill of browsing those big catalogs. Girls/women's fashions were of interest. Never boys/men's clothing. With internet, how far we have come!

    Years ago, I attended a Halloween party of a business-related young adult organization. Costumes were optional and some of us were not very creative. Similar to Paula's experience, one brave young man was fully cross-dressed. Surprisingly passable and attractive, enjoying "herself". Would believe that this was not a first.

  9. #9
    Female Illusionist! docrobbysherry's Avatar
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    I missed out on those feelings because I never even thot about trying on women's things until I was 50, Paula.

    But, I know one thing for sure! If you're not a professional writer, u should be!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  10. #10
    Miss Conception Karren H's Avatar
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    That was beautiful! How many times I wish I had taken my mother up on her offers to make me a dress and dress me up for Halloween. Think I would have had an amazing time but even at that young age I knew it was not allowed and was scared of the potential ridicule. I had to settle for getting caught by the local girls in their game, catch the boy and put a dress on him! That and browsing through my mothers walk in closet and lingerie drawers when she was not around.
    Current Obsession - Breasts and Lingerie!

    .......My Photos

  11. #11
    Platinum Member alwayshave's Avatar
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    Paula, what a great story. It is funny how some women understand and some don't.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  12. #12
    Senior Member Davina2833's Avatar
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    Paula,

    Excellent story, you were so lucky into the version of what might have been and you
    followed up on it. You are one lucky girl now women!

    Davina

  13. #13
    Aspiring Member
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    Can't wait for part two of your story, Paula!

  14. #14
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    Great story it is incredible how many things us girls have in common I can also remember those early days and that feeling of girly excitement.

  15. #15
    Senior Member GretchenM's Avatar
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    What a great story and so beautifully written as well. It brought back many memories of going shopping with my mother and how I would get excited when she turned off the aisle and headed into the women's department. So many wonderful things to see and mentally transfer on to my own body. Of course in the 1950's that was not something that boys were supposed to do. We were supposed to be embarrassed and very fidgety, eager to get out of that environment. Even the smell of the air in that department was different - it was wonderful. Thanks for triggering so many ancient memories.

  16. #16
    Paula Paula_56's Avatar
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    Surprisingly passable and attractive, enjoying "herself". Would believe that this was not a first.

    I like to say she was "not a civilian!"

  17. #17
    Loving my femme side tifftg's Avatar
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    Like many others here, the story resonated and invoked so many memories. Opportunities missed and explorations unmade. We were so sure that we were alone growing up, little did we realize that we had this sisterhood to share with and gain support from.

    Thank you for your delightful writings.

  18. #18
    Silver Member Maria 60's Avatar
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    I could relate and I felt the flashback excitement in your writing. For me it was when I went out with my mother and sister for her prom dress. I couldn't stop fantasizing about wearing one of those fluffy flowing dresses. My wife knows how bad I want one but I'm not willing to pay for something that will never leave the house or go to a prom.
    But you did bring me back and I'm sure someone must have noticed my light in my eye while staring at one of those dresses back then. Thanks for the flashback.

  19. #19
    Gold Member Sometimes Steffi's Avatar
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    Paula

    What a wonderful memory and so imaginatively written.

    I might have had dreams about such a story, but was too afraid to think about it "out loud".
    Last edited by Sometimes Steffi; 10-20-2023 at 11:23 AM.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

  20. #20
    Senior Member Debbie Denier's Avatar
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    Very thoughtfully and beautifully written. Thanks for sharing .

  21. #21
    Silver Member Frannie7's Avatar
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    That's a great story, Paula. Thank-you for sharing.

  22. #22
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    Paula, thanks for sharing. When I was growing up I did not have a sister or female cousins and female playmates were........basically on the lowest rung of the ladder. I was not drawn to anything feminine other than the white nylon full slips my mother hanged to dry on the clothesline strung in the hallway of our apartment. We had a girl, "Charlie," also known as Linda on the neighborhood baseball team. She was a "Tom Boy." I often wonder where is ended up in life. It wasn't until puberty that something "clicked" in my brain.

    What resonated in your post is what your mother said, "Want me to buy you a dress?" said with disdain. The world of the 1960's was not pleasant for gays and lesbians, and cross dressing males were thrown into the "gay" category. The word from the Sunday pulpit was filled with fire and brimstone for those who sinned, and, I was definitely a sinner. I was destined to burn in hell for my "impure" thoughts. Yet, I did succumb to the draw of mannequins in store windows. There were two women's shops in my neighborhood who were on opposite sides of the street on the main drag, Broadway. There was a bus stop at one. I would "wait" for the bus at that stop, checking my watch, and getting the fill of pretty clothes beckoning me. I especially love those mannequins adorned in long line bras and open bottom girdles, slips and other undergarments. My parents suspected I wore my mother's clothing. How could they not suspect since one of their two sons snapped the shoulder strap on her black bra? They did try to catch me, but failed. If I were to have been "catch" I am sure I would have been kicked out the family after I graduated from high school. Those days had a lasting imprint on me.

  23. #23
    New Member Lauren4444's Avatar
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    It?s important to remember where our journey starts. It?s also good to remember it?s not how we start but how we finish. You are an excellent writer, Paula. Thank you for sharing.

  24. #24
    Senior Member Diane P's Avatar
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    It's been a while but I posted a thread about my mother making a half boy half girl Halloween costume for me when I was about three or four. I also posted the two pictures I found. I don't remember wearing it but that could have been the start the start of my journey, who knows.
    The Pink Fog will be with you, always!

  25. #25
    Just can't help myself! Brenda456's Avatar
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    I love your writing. Thank you for posting.

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