• Creator
  • #396759
    Heather Kendall
    Registered On: October 18, 2020
    Topics: 2
    Replies: 10
    Has thanked: 115 times
    Been thanked: 67 times

    Hello my name is Heather, and I have been crossdressing for almost 40 years! This is my first time speaking about it in a public manner so forgive me if I don’t shut up. I started like many others, wearing things my mom had, then in my teens I “borrowed” items from my friend’s mom when I would visit, but  then I stopped after almost being caught in public. For years  I never thought about dressing up, until I was married to my first wife. I would wear her things when she was at work then feel ashamed of what I’d done. We went to a drag party, hosted by a coworker of mine. He dared all the males to come in drag, so she helped me get dressed up and bought me an outfit to wear that night. Until now, that was the only time I had done anything like that, and it was the only time I ever was dressed in front of her.

    Things didn’t work out for other reasons and we split up. After we were divorced I dated a bit then met my second wife. She was the first one to catch me and she wasn’t happy at all. Because of other troubles, we eventually divorced as well.

    At that point I had discovered  online ordering so I began to build a nice little wardrobe for my activities. Few pairs of heels (a girl needs her shoes, right?), stockings, panties, and a few lingerie items.  Shortly before meeting my current wife, I again felt ashamed and tossed everything I had purchased. Over the course of the next few years I would occasionally borrow a pair of my wife’s panties but nothing else. One night while we were talking, I said something that forever changed the course of my life.

    I told my wife that I could walk in her heels better than she could. She was quiet for a minute then asked me if I ever wore heels. I told her I had once gone to a drag party on a dare, and knew how to walk in them. Since we were close in size she got me a pair and wanted me to prove it. So I paraded around our living room and she was amazed. Then she asked if I wanted to get dressed up for her. I said yes rather quickly and we began to talk about my desire to cross dress.

    Since that day, about 8 years ago, I have been Heather about once a week. Most days I’m just a husband and a dad, doing all the usual masculine things genetic males do. But some days I get to be Heather with my wife, and enjoy that side of me that is kept hidden away from the rest of the world. Thanks to her love and understanding, I now have a chance to let the other part of me have some fun. Heather has a nice, but limited wardrobe. About 6-8 pairs of heels, and two pairs of boots, quite a few panties, stockings, pantyhose, several dresses, skirts and tops, three wigs, and a small collection of jewelry too.

    Now until very recently, Heather has been quite happy dressing up for her BFF and hanging out in the bedroom. A few months ago, our conversation began about having Heather go out in public. Having been dressed as a drag queen for a party is one thing, but to be out and dressed in a public setting is quite another. We eventually agreed that it might be best if Heather was the passenger in the car as we drove around to some of the shopping centers. We went out a few weeks ago and it was such a thrill to be driving past all these people sharing our little secret just between us. Before heading home, she found a secluded spot to all me to get out and walk around a little, then she gave me a big kiss and said it was time to go home.  We both agreed that was as far as either of us wanted to go with our public appearances and I can’t tell you how wonderful it is to have someone who truly loves and supports you completely. Well that’s my story, in the g-rated, condensed version anyway. I look forward to any comments and reading some of the many posts on the site.


Viewing 7 reply threads
  • Author
    • #396972
      Tababith Minx
      Registered On: October 18, 2020
      Topics: 3
      Replies: 28
      Has thanked: 43 times
      Been thanked: 82 times

      Hi Heather,

      That’s such a sweet story and for to have found your BFF to help you be you.

      Love Tabby xo

      2 users thanked author for this post.
    • #396872
      Bettylou Cox
      Registered On: May 26, 2019
      Topics: 17
      Replies: 1496
      Has thanked: 2522 times
      Been thanked: 4627 times

      Wonderful story, Heather; and 3rd time’s the charm for you, obviously.  You’re a lucky girl to have found her.  Now that you have actually gone out – and survived – you will surely want to do it again.  And with your wonderful wife as your wingman (wing-woman?), it should be easy and loads of fun.  Don’t wait too long to try.



      2 users thanked author for this post.
    • #396853
      Marlene Roberts
      Registered On: December 9, 2019
      Topics: 0
      Replies: 110
      Has thanked: 1278 times
      Been thanked: 242 times

      Love your story. You have a fantastic SO.

      2 users thanked author for this post.
    • #396849
      Alice Underwire
      Registered On: September 16, 2019
      Topics: 17
      Replies: 2049
      Has thanked: 710 times
      Been thanked: 3748 times

      Hi Heather,

      Welcome to CDH.


      2 users thanked author for this post.
    • #396823
      Bianca Everdene
      Registered On: April 11, 2017
      Topics: 16
      Replies: 569
      Has thanked: 2010 times
      Been thanked: 1999 times

      Welcome Heather, and thanks for sharing your story. You are so lucky to have such an accepting wife. It’s such a thrill being out as Heather isn’t it?


      2 users thanked author for this post.
    • #396786
      Rei Durden
      Registered On: October 11, 2020
      Topics: 14
      Replies: 477
      Has thanked: 2984 times
      Been thanked: 1757 times

      Hi Heather, thank you for sharing your story. You sound like you are very happy and surrounded by love and support and that is a wonderful thing indeed! Welcome to CDH and I hope you find the advice and courage you need should you open the next chapter in Heathers life.

      2 users thanked author for this post.
    • #396782
      Samantha Roarke
      Registered On: April 17, 2019
      Topics: 41
      Replies: 999
      Has thanked: 2331 times
      Been thanked: 2055 times

      Hi, hello, and welcome to Crossdresser Heaven! You have just arrived at the best and greatest CD site on the web! CDH has tons of very helpful crossdressing information, tips, and support from real people just like you! We highly encourage new CDH members to ask questions no matter how trivial you think they may be, as we are happy to answer to the best of our ability. We also love a well written profile, this helps everyone to get to know you better as the beautiful woman you are! We hope that you enjoy your stay here at CDH, as we are happy to have you as a part of our wonderful community.

      Thank you, Samantha Roarke


      2 users thanked author for this post.
    • #396763
      Teralynn Loving
      Registered On: October 17, 2019
      Topics: 2
      Replies: 999
      Has thanked: 6224 times
      Been thanked: 1597 times

      Hi Heather, Teralynn here. Welcome to our wonderful online community. Too bad you had to go through two other relationships before you found a significant other who loves all of you just the way you are! Give your wife a big hug and kiss from me for being so understanding and supportive. I do hope you will stay active on the site, because crossdressing people who are in a good relationship with a supportive significant other can be inspirational for a young crossdressing person, and we have a lot of those. If I can ever be of service please feel free to contact me through this site and let me know how I can help. A post on my home profile page wall will get the fastest response. – Blessings

      1 user thanked author for this post.
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