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Thread: What is Your Fondest Memory of Crossdressing?

  1. #51
    Platinum Member alwayshave's Avatar
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    When I had my makeover at True Colors, looking in the mirror was so mind blowing. I think about it all the time.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  2. #52
    AKA Lexi sometimes_miss's Avatar
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    Freshman summer, not quite 15, still pre pubescent. But fit perfectly in my sister's clothes. Everyone else at work, so I spent the day dressed up in her things, trying make up, reading her magazines, and of course, already having long, pretty hair, could easily have passed. I remember that day as if it were yesterday, though it was half a century ago. Took a long time to acquire a look-a-like dress to that one, which that fit me as an adult.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  3. #53
    Silver Member Maria 60's Avatar
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    As much as I did enjoy the first time wearing a slip and pantyhose in front of my wife but I seem to have another memory that sticks more. It was Halloween and my wife and in-laws and a few of there friends dressed up and we went house hopping. At one house of my inlaws freind we were leaving and I was waiting at the front door when the friend came up to me and told me how good I looked as a women. He then complemented my legs and lifted my dress exposing my panties and he reached down to my ankle and felt my leg all the way up. I didn't stop him from doing anything, I just stood there and let him touch me. Afterwards my wife told me she seen what happened from a distance and asked me if I enjoyed it. I told her it was something new and that I never had a man touch my pantyhose legs ever. I never told her but I felt that feeling for days later. I guess it was just like a feeling that I could pass one day.

  4. #54
    Aspiring Member
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    I went to an Oktoberfest in a complete dirndl outfit two years ago. I had a wonderful time, so great that I repeated it last year, enjoying it just as much. I describe my adventure at https://www.crossdressers.com/forums...ht=Oktoberfest . I include a link to my photo in the same thread.

  5. #55
    Gold Member Sometimes Steffi's Avatar
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    Quote Originally Posted by Lacey New View Post
    My fondest memory was the first time I tried on and bought a dress in a Dress Barn. The sales associate was so polite, helpful and completely non-judgmental. I was underdressed and pulling that tress on over my slip was just heavenly. My wife was away and I took advantage of the situation to shop and wear my new wardrobe every day.
    I'm so glad that you found a time to go to DressBarn and get the full treatment. How I miss DressBarn.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

  6. #56
    Silver Member
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    My best memory goes back to the first time i set foot in what is now my absolute favorite dress shop. I gathered up the courage and forced myself to walk in, armed only with my ATM card and my opening request. When the first SA (she actually turned out to be the store manager) asked "Can I help you?" I answered with my prepared line "Do you have any dresses in size 20?"

    "Oh!" she said in a way that told me she knew right away I was shopping for myself, "They're in that corner over there. Just let me know when you want me to open a fitting room for you." I thanked her and went to pick out a few dresses to try on. After a few tries I found two dresses that looked nice on me, and I took them to the register.

    Thus began my love affair with that store, where I met and made friends with the most wonderful sales staff who truly cares that I look good in my choices and love how it feels to be beautiful. Its a gift that keeps on giving. BTW, I am also a regular in a few other plus size dress shops in my area, where many of the staff know me by my nale name. The problem is only that not as many of their offerings works as well on me.

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