Michelle’s First Outing Dressed

Michelle's first crossdressed outing

I’m excited to share Michelle’s crossdressing success story with you, dear readers. I thought it was wonderfully timed, given how we’ve just been talking about feminine voice, and how it can sometimes prove a daunting challenge to even the most courageous among us.

If you’ve had a crossdressing success please share your story. Even if it seems like a small triumph, your words will bring comfort and inspiration to other readers. So without any additional preamble, I’m pleased to introduce Michelle.

Meet Michelle

crossdresser-success-story-michelle.jpg

Michelle’s First Crossdressed Outing

I am 38 years old and married. I just recently been dressing with the support of my wife. I remember when i was a kid trying on my moms clothes. But as i grew up I stopped mainly because of my family and friends. I live in a small town that does not look favorably on it. My wife and I started roll playing and I finally admitted to her I like dressing in femme. She accepted fairly quickly and is very supportive with it. We buy clothes and jewelry together. It has been great doing this with her.

Stepping Out Secrets

Michelle’s Crossdressing Success Story

I have been just dressing at home not really going out. If we go out it was always after dark when no one would see me. I finally decided that Michelle needed a day out. Being that we live in a small town where everyone knows everyone. We decided to hit a near by bigger city. Where we could go out to eat and shop. I picked a nice spring dress out. Put my makeup on and fixed my hair with alittle help from my wife. Put on some low heels that would be more comfortable for a day of walking. Michelle was ready for her first day out. Our first stop when we got to our destination was some food. So we stopped at a nice sit down reetuarant. When we went in I became really nervous. It felt like everyone in there was staring at me. Even though they payed little attention to us.

The hardest part was trying to talk to give the waiter my order. My voice as been the hadest for me. Well with a very uneasy voice I ordered which gave me away. But he took it well and was very nice and stayed with us till the we payed. After that having been made was tough on me. So we just drove around alittle then made our way home. I am not going to give up though just work harder. It was a blast being out as Michelle. And looking forward to the next time. Hopefully with a litte more success.

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10 Comments

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  1. Piper 1 year ago

    I still have dreams of doing this someday. Every success story I read is a little more motivation that it can be done! Thank you for sharing! 🙂

  2. Rosaliy Lynne 3 years ago

    i remember the only times I was accepted as a woman by my voice was on the phone and both times I had been eating something I hadn’t swallowed as yet. too funny. Voice needs attention until it becomes natural. good luck as you move forward.

  3. Vanessa Law 8 years ago

    And thank you Michelle for sharing! It’s wonderful to have you as part of the community.

    Hugs,
    Vanessa

  4. Misty LaRue 8 years ago

    Way to go girl…
    I’ve been amrried for 10 years and my wife has always knowen I wore woman;s clothes but out of respect for her I only wore underwear..
    Over the year I’ve always had that trapped in feeling until I couldn’t take it any more.
    So I sat my wife down and we had a long talk about who I have to become who..
    Only 3 week’s in and we’re getting a long much better then we ever have..
    Sure sometimes it;s not easy for her but she’s trying..
    Just like you we go shopping for clothes and shoes and make-up and it;s so much fun.
    She’s trying to stop me from buying more shoe but she’s not having any luck..
    I love shoes….
    Anyways enjoy and have fun I sure do..
    I’ve gone out in drag a few time over the years and I always had a great time while I was out..
    But in my case i have friend’s who do my hair and make-up as I’m not that good at it plus they love to do it fo rme so I say why not..
    Just be yourself and have fun and enjoy the sun..

    Misty/Robert

    • Michelle 8 years ago

      Thank you ladies for all the comments and encouragement. I am so glad to find this website. Its helped out alot knowing that i am not the only one going through this. It has been and is so much fun dressing and going out in femme. Thanks again Michelle

  5. Leslee 8 years ago

    I remember my first time out. I was so nervous and thought everyone was looking at me. After awhile I relaxed and just felt very normal and everything went well. So nice to hear of other girls going through the same experience I went through.The only thing I regretted was taking my makeup off after the night was over.

  6. Racquel Lynn 8 years ago

    Congradulations Michelle! The more you do it, the easier it becomes. The more you get used to being out in public crossdressed the more relaxed you’ll be, which leads to acting more natural. The more confident you are, the easier you’ll pass, but also the more used to it you get the less you think about it and you will act more natural and be more passable.
    No matter how good you look, being nervous, looking around too much to see if everyone is starring, or just trying too hard to pass is what will always give you away.

    Just relax, have fun and enjoy being you! It is also great that you have a wonderful wife to not only support you, but will also go shopping with you and out to eat. I was lucky enough to have had a wife that was also very supportive for many years, and since my divorce, most of my grilfriends have also been very supportive. It really helps so much to have that.

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