How to find the courage?

I am ok going out dressed now, but when I first started, I asked these questions in my head, 1) am I breaking any law by wearing womens clothing ? Answer NO. 2) If I saw was what I thought was a man dressed as a woman, would I walk straight up to him and say Hey why are you wearing womens clothing ? Answer NO, Id would think it but would walk right on by. 3) Will the police arrest me and put me in jail for wearing a skirt, Anser NO, will they hell 4) stay in public places help is alway nearby even though you are in a dress, Answer YES

With those questions answered I strolled out with my head held high, after all I am all woman for the afternoon shopping.

Wow!! Sounds so much like me. Just a little at a time and the confidence builds up. Thank you for sharing this girl friend, BIG hug

Like many here, I first drove around dressed, then decided to take a short walk through a park, staying away from others for the most part. One day,, though, I mistakenly thought I'd locked myself out of my car, and took a long walk while I tried to sort out what to do. I passed a couple of people who didn't give me a second look. I finally found my keys in my pocket, so I wasn't locked out after all, but the experience of passing with people I'd walked by gave me the confidence to stretch my bounds on subsequent walks-- same results-- no one reacted. Eventually I became comfortable to the point of going shopping, worked on my voice, and now regularly go into restaurants, shopping and generally spending my day as a woman. Your comfort level evolves as you go on. One of my fun gauges of how well I pass is when someone addresses me as ma'am-- very validating.

Sometimes events create a breakthrough.

I was in Albuquerque on business. I went into a consignment store and found a blouse that I liked. But, I wanted to try it on first to avoid being disappointed later if it turned out not to fit. The dressing room had a "guard", you know someone who would count the clothes you took into the dressing room. I was afraid to go in because I assumed that she would at least laugh at me.

Finally, I decided to do it. So what if she laughed at me. I was out of town and I'd never see her again. So, I took the blouse and walked up to her. She asked me how many items, and I told her that I had one. She didn't even look at the blouse. It didn't matter to her. All she wanted to know was how many items I had. That was easy. BTW, it didn't fit.

I went into a consignment store right next door. I found some harem pants that I liked. I asked the SA if I could try them on. She said, "sure" and pointed me to the dressing rooms. I tried on the haram pants. They fit and I loved them. I came out and told the SA that I wanted to buy them. Then, she did the most amazing thing. She said that I really needed a top. She showed me a few tops but I didn't like them. She kept bringing things over to me that she thought I would like.

The lesson here. I was a customer. She didn't care what I bought as long as I bought something. That was quite a lesson.

I can't help you drum up the courage, but I can advise that you go out on Pride weekend when there are lots of out folks about. That's what I did.

I also suggest you invest in a pair of fem sunglasses so you can avoid eye contact and scan your surroundings discretely from time to time.

I dove in cold turkey. I do have natural hair beyond shoulder length and I do have a natural bust (bra cup size DD).
I have been to the following places while wearing a tank maxi dress: Church choir practice, shopping at Kroger, local amateur radio club meeting (no women present), doctor's office, and to a filling station to fill up a gasoline can and a truck.
I have made no effort to alter my masculine bass voice. (Right now I am the only person singing the bass part in the church choir.)

Guess what? The world did not end. It wasn't a big deal to wear the dresses.
Below is a picture from Amazon of a burgundy version of the dress. I also have navy and olive versions of the dress.

John

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When I first went for a drive, I found it was hard to drive in heels when you've never done it. Just one of those weird things you come across.

A lot of gals have comfortable walking / driving shoes as well as high heels. It's not really safe to drive with heels.
So, heels are put on in the car after parking it, if you are the one driving.

Hi Olivia going out for me was a process. I think the first time I went out, as previously mentioned, was me in a car. Imagine my embarrassment when I was pulled over my law enforcement for blown headlight. Thankfully he was very professional and took it all in stride. My first time going out down town I wore a scarf around my face that was in Frankfurt Germany while I was in the military. Second time I was in Brussels, Belgium and did the best I could and showed my face in public wearing heels and makeup. From then on going out dressed was pretty easy. I have not gone out dressed since I got married.

In my mid twenties I worked for a very early morning delivery service which gave me a few opportunities to go out dressed. I would bring clothes and usually change half way thru my route. I particularly enjoyed window shopping at the dress shops and boutiques. I think I was only seen once because at door of one of my stops was a very pretty dress somebody left and I don?t think it was a coincidence.

Once I became a father I stopped. But recently being semi- retired I have had several excursions into parks and cemeteries. Late afternoon or early evening are best. By the time I return home it is dark and I can walked right it my house without notice.

I don?t think of it as having courage. To me it is more of a strong desire. It is a very exhilarating experience. I can?t wait for the next time.

My neighbors are used to seeing me wearing a dress. I cut the grass wearing a dress, and it's a lot cooler with the dress.
I tried wearing dresses around 2006 and I stuck out like a sore thumb since nobody was wearing dresses. Now that there are plenty of women wearing dresses it's no big deal anymore for me to wear a dress.
So I consider wearing a dress as something ordinary as I no longer am exhilarated with wearing a dress.

I first went out with short car trips. then getting gas, once I realized that nobody really cared what I wore I started going all over the place dressed.

StaceyJane,

Good for you.

John

Hi Olivia,
Lot's of grate advice here. I was almost a complete closet case, I was fortunate to meet someone from this site and agreed to meet them at a coffee shop. I was terrified, I don't know why or of what but terrified. It was one of the best few hours in my life and that I have ever had en femme. Enjoy yourself and the adrenaline rush.
Brenda