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Thread: What is Your Fondest Memory of Crossdressing?

  1. #26
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    The first time I dressed with makeup. I had gone from a man in a dress to a passable at a glance lady with a makeup bag of tricks and my first wig.

    Oh how special I felt at that moment, and how truly at home.

  2. #27
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    Many years ago I had a girlfriend who was accepting of my being a CD to the point of us buying sets of sexy underwear together, and then wearing it while having sex.
    Rather than putting up with it, she actively encouraged it by offering some of her own panties for me to wear.
    Mind you, she knew that it was a big turn on for me and benefitted from my state of arousal.
    All the same, it brought us very close together, which is why it's such a fond memory for me.
    Sadly that relationship came to an end for totally unrelated reasons.

    Oddly enough, she contacted me out of the blue on Facebook just a few weeks ago, which was very strange as it is 30 years since we last had any contact.

  3. #28
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    Definitely the first time I ventured out on Halloween and interacted with fellow humanoids. I wore a jade and black long sleeve floral print dress, black hosiery, black heels, all the proper undergarments; blond curly wig, full makeup, nail polish. I felt great. I was also in my mid thirties, so I still had some youthful look to my face and had not added some pounds. I got compliments. Forty years later I'd do better as an old haggard witch.

  4. #29
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    It has to be the first time I got waxed. Immediately ran home so I could change in to the outfit I had already picked out before I left. Thigh high stockings, cute mini skirt, corset. I have never felt as pretty and sexy before. Love the thought

  5. #30
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    I am of a Panty wearer, one time I bought a Warner Panty, it had the perfect nylon and spandex material, I always keep looking for something like that.
    Live Today as if it is your last day

  6. #31
    Member Katherine L.'s Avatar
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    Quote Originally Posted by HollyGreene View Post
    Oddly enough, she contacted me out of the blue on Facebook just a few weeks ago, which was very strange as it is 30 years since we last had any contact.
    Maybe her memories are as fond as yours.

  7. #32
    Senior Member phili's Avatar
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    The one that comes to mind as extra extra special was just a few minutes out of a day in a dress- As I got out of my car one fine day last fall to go to my ceramics class, one of my friends, another women in the class, was just ahead of me, wearing a skirt and blouse and jauntily walking to class. I skipped up along side her and we greeted each other, and chatted happily as we walked to class. There was something about our steps falling in sync, our skirts waving in time, our shared lightheartedness....I felt so at peace, and joyful, and that I had crossed over. There were no more barriers to girlhood.

    The next one that pops in memory is one morning going downtown, crossing a busy street in a very cute short dress and white linen short heels. As I stepped into the street, I heard a man I didn't see calling out for everyone around- 'There goes my next girlfriend!'
    Last edited by phili; 08-14-2020 at 10:04 PM.
    We are all beautiful...!

  8. #33
    Platinum Member Angie G's Avatar
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    the day she gave my a skirt and accepted my dressing. That was 14 years ago I'm still dressing and is still accepting it.
    Angie

  9. #34
    Silver Member Leslie Mary S's Avatar
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    You are a lucky person.
    Leslie Mary Shy
    Remember this:
    You do not have to be a man to love a woman, or be a woman to love women's clothes on her or yourself.
    _________________________

  10. #35
    Aspiring Member Lacey New's Avatar
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    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.

  11. #36
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    Going shopping and to lunch with a friends mom she told me to wear a nice dress and heels. His parents were hosting a formal party and he wanted me to come as a girl. She treated me as if I was her daughter. She came into the dressing room while I tried on dresses and after we picked one out she picked out the lingerie I needed to wear under it. The store staff told me how pretty I was.
    Last edited by lingerieLiz; 08-14-2020 at 10:12 PM.

  12. #37
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    Years ago when I had a real day job, I had to work at a exhibition in the Boston area, I boldly took from my wife's closet a red gown that I loved along with a bra, pantihose and some makeup and stashed it in my suitcase. It was the first time I had ever dressed and in a hotel away from home. Not much to add to that but it was the big, first time, and I drove home underdressed.
    Joanne

  13. #38
    A girl in the north east Jennylace's Avatar
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    the first time is a magic moment it's like the first thing a wife buys you completely unexpected and is the norm from that point on.
    Jenny Angelique Sanders
    https://www.flickr.com/photos/jennylace/

  14. #39
    Silver Member franlee's Avatar
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    The 1st time my 2nd wife and I discussed my desire to crossdress. We had been married about 3weeks. She listened to what I said and was exceptionally excepting. I had explained that I had CDed on occasion with my 1st wife and it was fun but not fulfilling and left me wanting to indulge in a more realistic presentation. She understood without any hesitation and she dressed me from the skin out as she would for church. I remember each piece of lingerie and the fillers she used then the makeup and hair. She was amazing in her abilities. I was in very good physical shape then and we were both the same height and shoe size. She dressed me in a white button-down L/S blouse under a 3 piece black with gray pinstripes suit. The suit was snug but fit and was filled out with the aid of some well-placed socks. The skirt was knee length. And black heels finished the outfit. But then the real emotional part was when she took her necklace that she always wore and placed it around my neck. We then went into the bedroom where the full-length mirror revealed the finished product. I was far better looking than I had ever been while CDed and was very near if not passable thanks to her skills and taste. She handed me a pocketbook and we went for a long drive. That was the 1st time I had ever really ventured out far from home. But with her next to me I felt like I could be her sister or best friend with no problems. Itt was a feeling I will never forget and always cherish.
    [SIGPIC][/SIGPIC]Fran
    It's worth something just being around to Fuss!

  15. #40
    Member Felicia M's Avatar
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    There are two that really stand out.

    The 1st is the very first memory I have of wearing my mother's stockings. I must have been four or five years old. I was seated at a desk in the living room by myself and I had removed all of the cushions from the sofa and stood them up on end around the outside of the desk legs so that no one in the house could see under the desk and see my legs. I remember the feeling of sheer joy. I absolutely adored wearing them, I remember my mother eventually seeing me in them somehow and helping me close the gaps in the cushions so no one else would see me. I really had no idea how blessed I was in that moment.

    The 2nd time was when I became accomplished at doing makeup and saw Felicia for the first time. This was only in the last couple of years and I had worked so hard to get better for a few months. I remember finishing up and looking in the mirror and having my breath taken away. I felt much like that younger self when I put on the stockings. Just a complete sense of sheer joy and happiness. It also changed me within forever. ❤️

    FM
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    and I still don?t know if I am a falcon, or a storm,
    or a great song.

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  16. #41
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    Heres one....

    Ive shared many times that I dont dress much...didnt dress for the first time in my life until 10 years after marriage. My wife knew from the beginning, but we just never tried it, even though she knew I wanted to. She isn’t great at gift giving or surprises...just not her thing.

    Anyway, about 18 years into our marriage she planned a weekend getaway, and had made all necessary purchases to complete the look. She knew what I liked, what I wanted, and surprised me. It’s the only time shes done that. Our drive to the location was a good five hours away, and I could tell something was up, because she was so excited by something. It was a great trip. Since then she has encouraged me to dress more...it did pick up to maybe 10 times a year but has settled down again.

    Maybe she’ll surprise me again ;-)

    Ultimately, she does it, because she wants me to be happy and she knows that I care more about her happiness than I do about mine.

  17. #42
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    Spending the entire day dressed as a woman and enjoying it

    Went to my friend's house where I changed into Jamie wearing my new blouse and skirt. He drove us to Biloxi and went to a couple of the casinos At one of them we had lunch(I was still Jamie) and I was a little nervous but the staff there treated me well. Enjoyed the lunch and then went to the mall and and a park and finally to our motel room. This was the first time I spent the entire day as Jamie and I enjoyed it. Of course I did love wearing the new outfit. I was now confident going out in public dressed as a woman.

  18. #43
    Member rian's Avatar
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    my favorite memory was when i completed confession of my crossdressing to my wife ,,,,then she asked if she can see me wearing some in front of her ,,,,i then wore my favorite lingerie outfit with a baby doll as a crown and high heels .... had a small walk infront of her ...she giggled and had the most beautiful sex that night ...
    Cross-dressing is a cross between woman's soul and man's heart.....

  19. #44
    Member Audrey34's Avatar
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    I've had many magical experiences dressing up. One of my faves was when I joined my support group, Pathways for the first time back in 2007. Still remember the thrill of walking fully dressed into the meeting room and getting a round of applause and many shouts of "welcome" as I was introduced to the group. Was such a lovely moment and I'll never forget it.

  20. #45
    Member Christina89's Avatar
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    I dont have a great memory for going out for the first time or doing things like make-up for the first time. It was mostly when I told my mother the truth. Yeah she didn't appreciate it. But truly it felt like a weight of lying was off my shoulders. I do have a plan come November for something else that will be memorable for me. But till then its a fantasy.

  21. #46
    Platinum Member Beverley Sims's Avatar
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    One time that stands out was Saturday morning dress shopping for something to wear that evening.

    My girlfriends had just found a new girlfriend in me and they wanted me to look sharp.

    Yep! A great weekend. :-)
    Work on your elegance,
    and beauty will follow.

  22. #47
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    if this was Facebook that story would definitely get a or a heart!

  23. #48
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    Going out En femme for the first time with my girlfriend as BFF. It was an amazing day. We had a great time.

  24. #49
    Exploring the Rabbit Hole TillyCambiare's Avatar
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    Its heartwarming how many of these moments involve SOs

    Tilly

  25. #50
    Member Katherine L.'s Avatar
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    Quote Originally Posted by TillyCambiare View Post
    Its heartwarming how many of these moments involve SOs
    So true!

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