(Please forgive the poor photo quality; at night pictures are difficult)

I have now experienced my first time of being crossdressed outside of my home (in the outfit pictured). I wanted to share my experience here, as I’ve been reading and appreciating other people’s success stories, so I will just add mine to the bank.

I’ve been interested in dressing up, pretty much forever, but realistically, I’ve actually only been doing so since high school. It began with some of my sister’s old clothes, which were left behind when she went off to college, and it eventually graduated into me buying some of my own. Throughout college, I dressed very sporadically and never held down a solid wardrobe. I’ve gone through too many purges to recount.

Recently, my general mood and mental health have been going through a downturn. In attempt to correct it, I thought deeply about some changes to make. One of the biggest things weighing on my mind has been the fact that for the last decade I’d been keeping my dressing secret from everyone in my life. I’ve started telling people, my sister and close friends. Opening up has been a fantastic experience; everyone I’ve told has been supportive and gracious, accepting me without hesitation.


That brings me to going out. Last week, I went out shopping with a girl friend of mine. Now that she knows, it’s a fun new thing we get to do together. It’s been great. We bought some dresses, shirts, shoes, all sorts of stuff, and put together an organized outfit. I made plans to hang out with a group of people, all super open and nice. When Saturday rolled around, I prepared myself. I showered, shaved, and dressed all the way up as best I could.

The hardest part of the evening was getting out the door and into the car. I was going somewhere and wearing something completely different from what I would normally wear outside. The drive over was exciting and nerve-wracking. When I pulled up to the place where we were meeting, I sat in the car for a couple of minutes. The place we’re meeting at is a club, real calm and low key. The people are super nice and open about everything, so without a doubt, it’s a great place for my first outing.

As I entered, I was immediately greeted with a smile by the girl behind the counter. I’ve been here before (not dressed) so she just said “Hey, welcome back.” The rest of the night went along in similar fashion, no real issues.

The best lesson learned from my experience; it really wasn’t as big of deal as I was thought it would be. Some people treated me no differently. A couple of ladies complimented my dress and shoes, and one girl said “Damn, you dress up nice; I didn’t even realize it was you.” Those were the best responses I could have received. I was able to just be me with the people I enjoyed being around. It didn’t matter if I looked like a girl or a guy.

For anyone who’s looking to venture out dressed, here’s a good protocol to follow. Trust in your friends, they like you. Find a friendly, open-minded group of people or club, and hang out with them in your guy clothes first. Then, just bite the bullet and go for it, and hopefully, you’ll be glad you did. Opening up, allowing myself to enjoy dressing up to the fullest extent that I wanted to was one of the most liberating and awesome experience I’ve had to this point.

En Femme Style

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    Sarah Dawson

    I have been dressing on and off for a few years. If I'm dressing up, I love to either do costumes or casual.

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    Paige Kalapac
    Paige Kalapac
    5 years ago

    Thank you for sharing your story! It does get a little easier every time. To be honest, I still stand at the door, afraid to turn the knob, and eventually blast through the door, and enjoy being Paige in the “open".

    Good for you! And, keep moving forward.

    T.J. Byron
    5 years ago

    Good for you! ENJOY being you….you look spectacular. At 72 yo, 73this year, I remember those young fox days. I will tell you to appreciate all the years I went out dressed, the 1960’s. Each decade there were new challenges; kids, their friends and neighbors. The style changes, storing my “stuff " in a garbage bag in the garage. As public norms changed, more often us out there, passing much more successfully. Today, I hope we who came threw these many decades, have made it better for this generation.
    ENJOY Being You!!

    Brandy Loveslace
    Brandy Loveslace
    5 years ago

    So happy for you! I think you are very courageous. That’s a really big first step.
    maybe I’ll be that brave someday.
    p.s. You look really pretty πŸ™‚

    Marlene Jones
    5 years ago

    great picture,and wonderful story.have fun with your new freedom.

    4 years ago

    Love your post and the advice you give. Also want to compliment you on how well you brush up. If I didn’t know different, I would have taken you as a genetic girl from your picture.

    Take care girl.

    Daisy Marie
    Active Member
    2 years ago

    Congratulations Sarah! I can imagine how you felt going out for the first time and I hope I can do the same soon.
    I liked your look and your tips and I hope I can find a group of nice people close to me so that I can hang out safely and my first experience doesn’t become so daunting.


    Sarah Kanter
    Trusted Member
    2 years ago

    Congratulations! The first time really out in public is something special. I’m so happy for you and glad you had such a positive experience.

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