49–year old gay crossdresser

Discussion in 'Transexual and Transgender' started by Jamie Lynn, Jan 12, 2020.

  1. Jamie Lynn

    Jamie Lynn Members

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    I realized when I turned 49, that I’m gay and I love dressing like a woman. That became a reality when I started wearing women’s white underwear all the time, then before I knew it, I started wearing black, brown or maroon knee-high socks. Then, New Years came, I wore a blue dress and a women’s wig for the first time. That night, I made a New Years resolution that I dress up like a woman 24/7, even when I go to bed. Also another resolution that I would wear dresses and skirts exclusively (no pants, shorts, tights or leggings). That was the start of a new beginning, wearing a dress or skirts with a long sleeve turtleneck, dark colored knee high socks, white bra and white underwear. I made a good choice to be a gay crossdresser.
     
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  2. Irminsul

    Irminsul Valkyrie

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    Pics please.
     
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  3. deleted

    deleted Visitor

    even Ive to think about that for a minute..
     
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  4. Jamie Lynn

    Jamie Lynn Members

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    They’re two different songs. Take A Walk on The Wild Side is by Lou Reed. Lola is by The Kinks.
     
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  5. Candy Gal

    Candy Gal Lifetime Supporter

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    Welcome to HIP.
    I am glad you are now happy.
    Need any girly tips?
    Just ask me.
     
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  6. Vanilla Gorilla

    Vanilla Gorilla Go Ape

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    So where does the gay part come in, you keep playing with yourself thinking about guys now?

    Or is it you think getting turned on by wearing panties and stockings makes you gay?
     
  7. I'minmyunderwear

    I'minmyunderwear Newbie

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    notice all the thought he put into color coordinating his outfits. a straight crossdresser would just throw whichever panties with whichever dress was available.
     
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  8. Irminsul

    Irminsul Valkyrie

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    Sounds you like you know about cross-dressing. :p
     
  9. Daretobare

    Daretobare Member

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    Dressing in women's clothes don't necessarily make or mean you are gay. There are many reasons why men dressup or wear panties. Many women too like a man that will show his feminine side and wear. So are you gay or just like dressing up?
     
  10. Vanilla Gorilla

    Vanilla Gorilla Go Ape

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    Orange and Green should never be seen
     
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  11. GLENGLEN

    GLENGLEN Banned

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    Unless There's Something In Between.......:smile:



    Cheers Glen.
     
  12. KathyL

    KathyL Super Moderator Super Moderator

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    And, considering where we are, are you trans or just like dressing up?
     
  13. Daretobare

    Daretobare Member

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    I dress for a few different reasons myself. I'm not into labeling what I may or not be.
     
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  14. Daretobare

    Daretobare Member

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    But I do believe all men have a feminine side and are afraid to admit or explore it. I enjoy it myself. And that's my biggest reason
     
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  15. Candy Gal

    Candy Gal Lifetime Supporter

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    Good for you.
    I embrace all.
    I cannot stand prejudice.
     
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  16. deleted

    deleted Visitor

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  17. .
     
    Last edited by a moderator: Jan 14, 2020
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  18. Jamie Lynn

    Jamie Lynn Members

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    B994D81F-9FD9-46AA-8B04-848733C024E6.jpeg Today, I’m wearing a white dress, yellow turtleneck, black shoes and black knee high socks.
     
  19. deleted

    deleted Visitor

    Sounds like an average day to me..
     
  20. Jamie Lynn

    Jamie Lynn Members

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    I had to put that pic up. I don’t know what restrictions you have in this forum as far as showing skin.
     

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