49–year old gay crossdresser

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

  1. Jamie Lynn

    Jamie Lynn Members

    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.
  2. Irminsul

    Irminsul Valkyrie

    Pics please.
    Bayer Sanyo likes this.
  3. cuin666

    cuin666 Members

    Take a walk on the wild side...

    Or is it Lola?

    I get those two confused...

    Same song?
    Bayer Sanyo and Orison like this.
  4. Orison

    Orison my dog is full of stars Lifetime Supporter

    even Ive to think about that for a minute..
    Bayer Sanyo likes this.
  5. Jamie Lynn

    Jamie Lynn Members

    They’re two different songs. Take A Walk on The Wild Side is by Lou Reed. Lola is by The Kinks.
    Bayer Sanyo likes this.
  6. Candy Gal

    Candy Gal Supporters Lifetime Supporter HipForums Supporter

    Welcome to HIP.
    I am glad you are now happy.
    Need any girly tips?
    Just ask me.
    Bayer Sanyo likes this.

  7. 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?
    FredBrice and Bayer Sanyo like this.
  8. I'minmyunderwear

    I'minmyunderwear voice of sexy

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

    Irminsul Valkyrie

    Sounds you like you know about cross-dressing. :p
    FredBrice, Bayer Sanyo and GLENGLEN like this.
  10. Daretobare

    Daretobare Member

    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?

  11. Orange and Green should never be seen
    Bayer Sanyo likes this.

    GLENGLEN Lifetime Supporter Lifetime Supporter

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

    Cheers Glen.
  13. KathyL

    KathyL Members

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

    Daretobare Member

    I dress for a few different reasons myself. I'm not into labeling what I may or not be.
    Bayer Sanyo likes this.
  15. Daretobare

    Daretobare Member

    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
    FredBrice and snowtiggernd like this.
  16. Candy Gal

    Candy Gal Supporters Lifetime Supporter HipForums Supporter

    Good for you.
    I embrace all.
    I cannot stand prejudice.
    Daretobare likes this.
  17. Orison

    Orison my dog is full of stars Lifetime Supporter

    Bayer Sanyo likes this.
  18. .
    Last edited by a moderator: Jan 14, 2020
    FredBrice and Bayer Sanyo like this.
  19. Jamie Lynn

    Jamie Lynn Members

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

    Orison my dog is full of stars Lifetime Supporter

    Sounds like an average day to me..

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