Gather the courage to crossdress for the first time

You’ve been telling yourself for weeks that you’re going to do this. Debating with yourself, arguing with yourself, justifying why you didn’t go this weekend. Every time it ends with a promise that next time, next week, next month will be different. Yet somehow things don’t seem to change. You find that wearing your feminine finery at home doesn’t seem to satisfy a deeper longing inside you anymore. For a brief moment you wonder, “Am I cured?” Of course, you already know the answer to that question.

What stops you from crossdressing?

I don’t mean just crossdressing within the safe confines of your own home. I mean going out crossdressed for the first time. I mean gathering up all your self confidence and strutting out the door looking the best you ever have. Boldly going where very few other men have gone before.

Today I’m going to share a few reasons why you might be putting off such an important step, and how you can overcome your barriers to crossdressing.

You have nowhere to go: This is probably the number one reason why people don’t go out crossdressed – because you don’t think that you have anywhere to go, somewhere that is safe, where you won’t be recognized, and someplace that you can enjoy. Just before my transition I used to spend every weekend in a park just round the corner from my house. It was my sanctuary. I was able to be myself for a few hours, enjoy the sunshine with little fear of being outed. It was a safe place for me, and helped me build my confidence to go other places. You might find a local transgender meeting group (also a safe place), or a transgender friendly club or restaurant (your local transgender organization will know of a few) or if you’re fortunate enough – with a group of your friends who are accepting.

What stops you from crossdressing?

What stops you from crossdressing?

You’re afraid: Fear comes in many forms. Fear that you’ll make a fool of yourself, fear that someone will recognize you, fear that you won’t pass and get into trouble. Since I have readers from all over the world it’s worth noting that you should take the time to understand local laws. Generally across the US, Europe and Australia it is not illegal to crossdress. The biggest antidote to fear is experience. Do it a few times and you’ll gain confidence. Spend a few hours en femme and you’ll build the habits and mannerisms that serve you well as you venture further out. Most importantly, start with a place that feels safe to you. Take baby steps.

You look horrific: Honestly sweetie, you don’t look that bad. This is a legitimate worry, since learning to be feminine takes time and practice. Even then many ladies aren’t blessed with the figure to pass there are still things you can do to improve your chances of passing in public. I’ve known many wonderful ladies who didn’t pass, but held their heads high and walked down the street like they belonged. Confidence is the difference between someone pointing and laughing, or someone coming over to chat with you because they find you generally intriguing.

So what stops you from crossdressing?

Hopefully with the few examples I’ve given you, you can see that it’s not the world that stops you from crossdressing, but yourself. Take a moment to think about what’s been holding you back, perhaps this weekend will be different…

Are there other reasons I missed? Please comment and let me know what has held you back, and how you overcame it. This will be a blessing to others just starting out!


P.S. Thank you to all the ladies who responded with their crossdressing success stories! I received them, I’ll reply individually soon. If you’d like to share, please submit your crossdressing success story.

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32 Comments
  1. Veronica Raines 2 months ago

    Don’t know, if this counts, as this is the first time, I’ve told anyone about how I feel, about wearing proper clothes. I sort of grew up, in a small town of 1,200 population. It was basically run, by the Italian mob. There were only 52 kids, in high school. One Halloween, I went to the party, at the high school, dressed like a woman. My mother helped me, get dressed in her clothes. A white bra, with falsies, under a white blouse. A pair of white panties, under a black skirt. She had some low heeled black shoes, and of course, I wore her nylon stockings. I also wore her black, little hat, which had a veil, with a pair of black gloves. Of course, she put makeup, on me. It was about six blocks, to the school, from our house, and I started off walking, carrying, a chocolate cake, for the party. She had taught me, to always walk with my head held high, and as I walked to the school, (it was dark) I felt so proud, that I walked with my shoulders back, and head held high. On the way there, a black car, with the two big shots, of the school, in their senior year, were in it. They made a U turn, and drove back by, whistling at me, and say, “Hey baby, where you going.” Of course, I said nothing. They made another u turn, and came up beside me, saying all kinds of things, kids back then, said to girls, when they were trying to pick them up. Then finally, one of them asked, if I was going to the party at the high school, and I nodded my head yes. It was a two door coup, and when they stopped, the most sought after senior in the school, with the nickname, Tiger, got out, and held the front seat, forward, so I could get in. However, he asked if he could hold the cake, while I did so. Handing me the cake, he got back in the car, and Bill, the other senior, started driving, very slowly, towards the school. Of course, Tiger kept trying to get me to say something, and then I couldn’t hold it back, any longer, and started laughing. Of course, everyone knew, everyone, and they both knew my laugh, and Tiger jumped over the front seat, saying, WTF, is that you Steven. I just nodded my head, and Bill stopped the car. I don’t remember, what all that was said, between us, but they made me get out of the car, and told me, if I ever told anyone, about this, they would beat the crap, out of me. As I walked the rest of the way to the school, I felt so damn proud, that they thought I was a girl. At the school, when I walked in, the lights were on, and everyone knew who I was. For the next couple weeks, I got ribbed about dressing like a girl. Plus, two guys that never did like me, tried to make something of it, and I had to kick their butts. That was the only time, I dressed up like a girl again, and left the house to be seen. Apparently, the head man of the mob, heard about it, and got word to my mom, not to let me do it again. Now, I’m starting all over, the way I should. You never grow to old.

  2. Susanna Monroe 5 months ago

    For me it’s fear that I’m not as good at this as I think and I’ll get called out, laughed at, chased with pitch forks, that kind of thing. I recently did my first outdoor trip but didn’t leave the car. Small steps and all that…

  3. Rebecca Smith 9 months ago

    I’ve driven home from drill dressed up twice now. Last weekend I wore make up. I still need to practice that aspect but I didn’t think it was too bad, tried to keep it minimal.

    Anyway, I made a point to make sure I was dressed femme to get my mid-point gas and to use the restroom. Honestly it took every bit of courage to walk in there. I’ve been in several dangerous situations and I think my heart rate was quicker walking to that stall.

    I don’t know that I could have done it without the awesome ladies on here and their encouraging stories and advice.

    I did learn that a longer dress would have been nice given the windy weather. I should have brought more than one outfit just in case.

  4. Bronwyn 9 months ago

    Fear fear fear is what has kept me in the closet fo 30 years. Being a total introvert does not help at all. But thats my personality and at my age, wont change. Some can go outside thier front door, many cannot. Bronwyn

  5. johngordon 2 years ago

    All of the above!

  6. Joann 2 years ago

    I just started to go out dressed the first time was just like most of us but what a thrill it was now I can’t get out enough my wife knows but does not like me going out she is abraded I will get seen but hollowed not is coming up and I have just bought a sexy red dress and 5 inch heels I can’t Waite but for now I sit hear with my bra and panties on I wish I had some one to go out with any one in central Minnesota out their

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