• Creator
  • #568953
    Holly Williams
    Registered On: April 27, 2019
    Topics: 11
    Replies: 3
    Has thanked: 81 times
    Been thanked: 137 times

    So I have lately been struggling keeping this whole crossdressing/gender issue thing a secret, it’s eating me alive. I feel I needed to talk to someone about it. So I decided to think outside the box and talk to my boss.

    For context, I’m a lifeguard. I work at a gym. My boss is great, only like a few years older than myself. I thought she would be the perfect person to talk to.

    I was very uneasy and often had to take deep breaths just to get the words out of my mouth. Eventually I just sucked it up and I told her that “I’ve been having gender issues” she seemed unfazed. She reassured me that everything was alright. As we were talking she asked me what I liked to wear, my favorite style etc. I told her I loved skirts and dresses and she again seemed unfazed. She was support supportive and that alone made me happy, she said if I needed her, to contact her. But, it gets better.

    I decided to take the gamble and I decided to ask my boss if I can potentially dress at work. She said absolutely. None of this feels real. I can’t believe I managed to gather the strength to do this. I’m just so happy I almost burst into tears and hugged her. Obviously I have to wear what the female lifeguards wear if I choose to come in dressed. So that means I have to wear the usual unisex shirt with leggings or shorts, my boss even suggested I wear a bathing suit underneath in case I ever had to make a rescue. Not only did she give me the okay to dress femininely at work, but she also complimented my eyelashes which I thought was funny, she said “girls would kill to have eyelashes like yours.” She also proceeded to tell me the CEO of the place I work at is a lesbian herself. So that means that I know I’ll be okay. My boss said if I decide to change my attire, she’d back me up 100%.

    Theres also usually a water aerobics class that lasts a few hours and I told the teacher of the class of my idea to change to feminine attire. She was also extremely supportive and told me her daughter was a lesbian too. The amount of support I got from both my boss and coworker were incredible. I remember shaking and feeling extremely uneasy during both exchanges. But both couldn’t have gone better.

    I have already ordered two pairs of leggings, shorts, and two bathing suits. I’m just stunned at the support I got today. I still feel so overjoyed and happy. Well, guess it’s time to give it a shot!

Viewing 9 reply threads
  • Author
    • #569960
      Raquel Smith
      Registered On: August 26, 2021
      Topics: 8
      Replies: 500
      Has thanked: 1427 times
      Been thanked: 1615 times

      Holly, that’s incredible news!  I’m so happy for you. 🥰

      Not to mention the fact that what you did took incredible courage.

      Congratulations  🎉

      Much love,


      1 user thanked author for this post.
    • #569579
      Liara Wolfe
      Registered On: August 14, 2021
      Topics: 3
      Replies: 750
      Has thanked: 1274 times
      Been thanked: 2764 times

      Wow, so happy for you.

      Hugs, Liara

      2 users thanked author for this post.
    • #569000
      Darcy Grigsby
      Registered On: July 1, 2020
      Topics: 23
      Replies: 134
      Has thanked: 17 times
      Been thanked: 769 times

      Awesome. That was bold of you for sure, but if it results in your happiness that’s fantastic.

      Any concerns of what others/public might say?

      3 users thanked author for this post.
      • #569014
        Holly Williams
        Registered On: April 27, 2019
        Topics: 11
        Replies: 3
        Has thanked: 81 times
        Been thanked: 137 times

        Honestly, yeah, big time, I’m super afraid of what people will think of me. I’m glad I have the option to do this, but now I just need to conquer my own mental hurdles. I’ll be honest when I say I’m terrified of what people will think.

    • #568997
      Jill Quinn
      Registered On: July 24, 2021
      Topics: 1
      Replies: 92
      Has thanked: 471 times
      Been thanked: 402 times


      That is wonderful news! Good for you for having that kind of courage. And thank you for sharing your success!

      Hugs, Jill

      3 users thanked author for this post.
    • #568990
      Angela Booth
      Registered On: August 1, 2020
      Topics: 4
      Replies: 628
      Has thanked: 1724 times
      Been thanked: 3028 times

      It is lovely to hear wonderful experiences like yours. It shows that things are moving forward at a pace and acceptance is easier to find. let’s face it, in your role who cares what the rescuer is wearing. So happy for you.

      3 users thanked author for this post.
    • #568985
      Bobbisue Jones
      Registered On: May 24, 2021
      Topics: 12
      Replies: 689
      Has thanked: 4829 times
      Been thanked: 2712 times

      Hi Holly, Congratulations on such an uplifting story. You were very brave to take the big step. You go girl.  You are an inspiration to others to take a chance! Love and hugs Bobbisue J

      4 users thanked author for this post.
    • #568983
      Stephanie Roberts
      Registered On: May 20, 2020
      Topics: 20
      Replies: 1143
      Has thanked: 9630 times
      Been thanked: 4488 times

      Well done Holly! That’s fantastic.
      Love and hugs, Stephanie 💖

      5 users thanked author for this post.
    • #568973
      Michelle Trott
      Registered On: April 7, 2021
      Topics: 1
      Replies: 370
      Has thanked: 770 times
      Been thanked: 1667 times

      That is very brave. Good for you. And what a great boss.

      5 users thanked author for this post.
    • #568969
      Connie Twirl
      Registered On: August 18, 2021
      Topics: 14
      Replies: 431
      Has thanked: 731 times
      Been thanked: 1807 times

      Well done Holly! And well done Holly’s boss too.



      5 users thanked author for this post.
    • #568959
      Michelle McQueen
      Registered On: June 14, 2021
      Topics: 16
      Replies: 718
      Has thanked: 3435 times
      Been thanked: 3631 times

      Hi Holly. Congratulations on being so brave and the great response you received. Now get your girl on and be happy!

      5 users thanked author for this post.
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