Hello, this is my very first post; I just joined the other day. I truly don’t know where I’m going with my crossdressing.

I recently turned 65 and am retired, happily too. I must add, healthy and fit as few people take me for my age. I have many interests that keep me busy, music, old cars, photography, and others.

After reading a number of other stories here, it’s clear that mine is similar. I first started crossdressing around age 12 by trying on my mother’s underwear. At that age, we are entering puberty and things female are suddenly much more interesting, including clothes. The old expression about clothes “making the man,” I think we might agree that clothes make the woman, too!

My favourite was what I know now is a corset. My mother was a bit heavy so she’d wear shapewear to help out. The feeling was fabulous when I slipped into it and one of her slips.

I was deemed old enough to be left home alone while they went out shopping. Being an only child, I had time to myself to, be myself, I guess. I simply cannot remember what led me to try on my Mom’s things, but I loved the feeling of her clothes, even though the fit wasn’t great. This also quickly became highly sexual for me, too. I started more fully dressing, using socks to fill out where her breasts would have filled the bra pockets, and then putting on a shirt. I never tried on any of her outer clothes.

We moved in with my grandmother after the sudden death of my grandfather when I was around 15. I had little private time, but I didn’t seem to mind. I don’t think I had the urge or felt the need to dress for many years; I had discovered girls! Even when I lived on my own for a few years before I was married, I never once considered dressing.

I met a wonderful, beautiful woman who quickly became my best friend and lover. Over the last 35 years together, we’ve had two kids, both pretty well grown up, though the youngest is still attending college and living part-time in another town. We have more time to ourselves now and love it.

As a couple, we’ve had a very active and private life, in that respect. As the children aged, adult “play-time” got tougher. We did a male/female swap at Halloween after everything was done and our kids were safely tucked away. The old thrill of dressing in women’s clothes returned. We added dressing to our private time; I’d dress up occasionally, but it wasn’t something I felt a need to do regularly. I sure enjoyed dressing when I had the chance!

That went on for 10-15 years. Over the last couple of years, I started wanting to do it more. Since the middle of last year, I find myself ever more drawn to the femme side. For Christmas, I usually buy my wife some kind of sexy clothes, but since she is a plus-size now, it’s hard to find nice things at the lingerie stores. I started looking online and ended up buying myself a couple of nice bras, garter, and stockings. At the same time, I ordered similar items for her!

One of the sites I browsed through had a section for crossdressing supplies. I was fascinated by all of the “extras” one could purchase. Those very realistic breast forms looked amazing; much better than using socks, like I did when I was 13. I haven’t bought any forms, not yet anyway.

I realize that she knows I’m enjoying dressing up more, and she’s been understanding about it; I don’t want to push things too far. I don’t feel the need to fully transition, but I am very mixed up in my feelings about all of this.

I don’t want to mess up things with her, and I certainly don’t want the rest of my family to know; some might be more accepting than others. I’m not nearly ready to go out dressed, and I don’t think that I’ll ever get to that point, but I didn’t think the femme side would feel so strong in me either. I do have this interest in dressing well enough to go out in a limited public setting. My other issue, as it were, is the beard I’ve worn for 40 years, and is very much ensconced in my male persona. That would have to go if I were to go out in public.

It was early this year that my femme name just kind of popped into my head. I began thinking that my femme side should have a name, and a day later, Amy appeared; it’s nothing like my male name.

I’m conflicted in my feelings; my male side is very strong though I’ve never been a macho guy. In some past situations, I suffered because I wasn’t. I’m only attracted to women; I absolutely love the look of women, finding so many of them attractive, regardless of their ages.

Last week, I took another step and went to a shop in the city (I live in the country), which sells items for CDs. I bought a nice wig and another skirt for myself. The person was nice and very understanding; it was nice to actually shop for Amy and not pretend it was for someone else.

As I mentioned, I’m feeling conflicted. I need to let her know how much I love the feeling of being dressed. I’m worried, as we are finally retired and hope to do some travelling and other activities that we’ve wanted to for many years that I might upset our plans and hurt our relationship. I don’t want that to happen.

Anyway, that’s where I am now. I’ve wanted to share this with others for quite a while.

Amy

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15 Comments
  1. Olivia Livin 3 months ago

    I’m not sure when you wrote this, but I’m pretty sure you’ve come a ways since. Is there a chapter 2 ? lol.

    • Author
      Amy Myers 3 months ago

      I did write this not long after I joined up about 3 months ago, so I have come a long way.
      You are right, I am working on a chapter 2.
      When I read this again, I could not believe how much Amy has changed in the fairly short time since this was written.

  2. Mona 3 months ago

    This is a great story Amy thank you for sharing it with us. And Wow it’s amazing how similar it is to my own story, pretty much word for word. I wrote an article here several months ago called “Mona says yes to the dress” that you can find if you go back far enough and you’re interested.
    I expressed a lot of confusion as well about why the urge has come back so strongly at this point in my life (turning 60 this year). In the end I think it will always remain a mystery so for now I’ve decided to just have fun with it and also to be transparent and completely honest with my wife. I only came out to her last year after 35+ years together. She’s still trying to process it and I just let her go at her own pace. I keep it completely under the radar so essentially it’s DADT for now. I don’t feel like I’ve been all that dishonest with her because I did not dress nor have the urge to for very long stretches of time, like the past 20 years as we’ve been busy raising our two kids.
    Anyway thanks for telling your story and I hope you realize you are not alone. Plenty of wonderful support and understanding to be had from all the other girls here. It’s so different now from those early pre-internet days when there was no where to turn. Hope we see and here more from you Amy. Your friend Mona

  3. Lucinda Hawkns 3 months ago

    hello Amy nice to have you here on C.D.H. here us girls under stand what you go threw, we all started about the same way, back in the late 60s or 70s i would think. x dressing would go away for months or years then re appear and not go away. i am in my late 50s and have my own collection of dresses, nylons, make up, jewelry, perfume, panties, pad, bra;s, some skirts and slips, some heels. wife knows and lets me dress up when our last adult child is still home is out for a few hours. she tells me i can do what i like and i know what that means. she has seen me getting dressed up and talking to me but will not help with make up or sit and talk like 2 woman.

  4. Sidney Silver 3 months ago

    Thank you Amy for sharing your story and perspective. You clearly deeply care about and love your wife, and I find that wonderful. 🙂

    I’ve found it best to be honest as I can with those I love, and who love me. Sounds like you’ve done that, but care about how it all effect her. After all, it effects both of you.

    Kinda like yourself, I only recently truly discovered this side of myself. When I did, I wanted to embrace it. I wanted to experience and to know it the best way I could. I did that by being kind to myself, and others. By taking one day at a time, and by trying new things.

    Thanks again for sharing! I also want to hear about Chapter 2! 🙂

    Best,
    -Syd

    • Author
      Amy Myers 3 months ago

      Syd;
      Thanks for the kind words and thoughts. Will get Ch 2 done soon, but there is a long wait till it actually gets published up on the forum, as they have so many great stories sent in by members.
      XO
      Amy

      • Sidney Silver 3 months ago

        I know dear! Just wanted you to know I’m interested in your journey. 🙂

        Actually, I have a pending story myself, soon to come out as well! Let me know what you think if you see it!

        Thanks again!
        -Syd

  5. Tiffany Alexis 3 months ago

    Thank you for sharing this wonderful story Amy! I think my favorite part is your really cool SO, I always love hearing stories where one of us finds true happiness in relationships AND dressing!

  6. Stacy Ann May 3 months ago

    Good luck, Amy! Thank you for sharing your story.

  7. *skippy1965(Cynthia) 3 months ago

    Amy-sorry for the delayed reply-I was at the Esprit conference from May 11-May 20 (where iI met Sidney Silver and her wife Grace) And am catching up on the articles published while I was there. I’ve been here on the site for nearly four years now (since it was only a little over a hundred members) and the leaps and bounds I have taken I could not even imagine five to ten years ago. My ex couldn’t deal with the dressing and we split up back in 2004-5- I think she realized before I did myself that it was more for me than just the clothes . I am still discovering myself and where my life will lead me but I know that Cyn is never again going to hide herself away in the shadows. She deserves better than that. You can read about my journey in the many articles and forum posts I wrote over the last several years here. (FYI if you want to read “older” stuff by ANY particular member, you can go to their profile page and click articles or forums underneath their cover photo to see all the items they have written-this makes it easier than scrolling back through the main articles page or worse trying to find older forum posts.)

    Thanks again for sharing your story and good luck on living your dreams!
    Cyn

    • Author
      Amy Myers 3 months ago

      Thank you for your kind comments, Cyn.
      I do have a “chapter 2” I want to write for submission. I am not sure how far I will go, as Amy, as, like you, we are still on our journey forward. But I am less inclined to be hiding away, like I used to.
      Amy

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