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  • #633482
    Michelle Smith
    Participant
    Registered On: April 1, 2022
    Topics: 3
    Replies: 6
    Has thanked: 15 times
    Been thanked: 44 times

    Growing up I lived next to a woman named Norma.  She seemed to have it all.  She was beautiful, had a husband who was a well-known doctor, and cute kids.  At first I thought I was attracted to her, but as I spent more time around her, I realized that I wanted to be her.  I loved her sense of dress and the way she gracefully moved around and her kindness.  She would hire me to housesit when her family was away and of course I would take every chance I got to explore her room.  For someone who dressed so well she had the most basic bras and panties that I would try on.  It was so thrilling, but then I had a new feeling.  One time I sat on her bed in her underwear and started to wonder what it was like in the room when her husband saw her in this clothing.  The thought scared me at first, but then I started to embrace it.

    Years later I saw how her “perfect” life fell apart.  Her husband was a serial cheater who had abused her and his lawyers made short work on her in the divorce settlement.  Her children sided with the ex-husband and don’t really talk to her anymore.  Yet even without the picture perfect family and all the money, she is still the most beautiful woman  I know in her 60’s who carries herself with dignity and a smile for everyone.  I so badly want to tell her why I liked spending so much time with her and ask her for help with dressing, but I am so scared.  She makes me want to be myself with her, but I don’t know what I would do with the rejection.

Viewing 4 reply threads
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    • #633533
      Lisa Renee
      Lady
      Registered On: January 7, 2022
      Topics: 0
      Replies: 11
      Has thanked: 3 times
      Been thanked: 100 times

      Please Jessica Cross Johnson, go on.

    • #633532
      Angela Booth
      Lady
      Registered On: August 1, 2020
      Topics: 9
      Replies: 1155
      Has thanked: 4368 times
      Been thanked: 5165 times

      Charlotte has the right idea. If you have stuck by her all these years and appreciates that you have been there for her then she may not reject you at all. Have a chat about her thoughts on crossdressing and if it feels like good responses then tell her that you crossdress. I would maybe leave the bit about wearing her clothes for now but nothing wrong in saying that she was an example to you in the way she dressed. She could take it nicely, as a compliment. 

      She could see it that she would rather have had a loving crossdresser than a womanising abuser. Another thing, she may have already figured her stuff was being worn and said nothing, you never know.

      3 users thanked author for this post.
    • #633524
      JessicaCross Johnson
      Duchess
      Registered On: August 25, 2015
      Topics: 1
      Replies: 56
      Has thanked: 176 times
      Been thanked: 181 times

      There are many women out there, even older than you, who would love to have a companion like you, I found one when I was in my 20’s. I cannot really remember the introduction series except that I was doing something around her house and had gotten very sweaty, she told me to take off my shirt and she took a damp wash cloth, wet it and proceeded to wipe down my chest and back then wipe me off with a nice warm towel. My clothes were very wet, so she unbuckled my belt and opened my jeans, by this time I was totally in shock, so she continued to wipe me down and dry me off. She then walked out of the bathroom, I sat there in shock for a few minutes hearing her moving around in the other room. After a few minutes she called me to come to her as I was, so I walked into her bedroom. She stood there in a beautiful dress and 5″ heels, motioned me to come to her, mesmerized I walked to her, she handed me a pair of beautiful purple panties, then turned me around and fastened a matching lacy bra with C class inserts. Then she gave me a pair of purple stockings, had me put them on and handed me a pair of 4″ purple stilettos and gave me a purple slip which came down to just above my knees. Then the piece de resistance, A slim purple dress and held it up so she could lower it over me, took me over to her vanity and proceeded to make me up with dark themed makeup and finally a black as a crows wing wig. There is more to the story but I’ll stop for now to see if there is any interest to go on.

      5 users thanked author for this post.
      • #633539
        Michelle Smith
        Lady
        Registered On: April 1, 2022
        Topics: 3
        Replies: 6
        Has thanked: 15 times
        Been thanked: 44 times

        Well I would love you to go on, but it seems like too much of a fantasy to be true 🙁

        1 user thanked author for this post.
    • #633508
      Michelle McQueen
      Lady
      Registered On: June 14, 2021
      Topics: 28
      Replies: 1512
      Has thanked: 9796 times
      Been thanked: 7403 times

      We know 99.99% of cis women do not like men who dress as we do and she is probably no exception. You admire this woman so much but I’m afraid you have projected your fantasy upon her thinking she would be accepting and there could be some sort of relationship there but chances are she would view you as a weird stalker whos been wearing her underwear.

      Talk to her and try to learn her views on CD’s first before you ever open up about yourself. You may save yourself an embarrassment.

      4 users thanked author for this post.
    • #633502
      Charlotte Lapin
      Lady
      Registered On: December 12, 2019
      Topics: 0
      Replies: 52
      Has thanked: 25 times
      Been thanked: 232 times

      From your description, she was sorely used and betrayed by a man and she could interpret this disclosure as a sort of betrayal, as well.  Of course, it could very well go the other way and she could be immensely flattered you have viewed her as a model to emulate.

      You might try slipping into conversations references to movies or personalities which touch on crossdressing or trans and see how she responds.  If she responds positively to references to, say; To Wong Fu; Priscilla, Queen of the Desert; Breakfast on Pluto; Welcome to Marwen; and the like, you’d have a better sense of how she feels about it.

      Heck, if you want to keep it extra light to start, bring up Tyler Perry first!

       

      3 users thanked author for this post.
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