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A light start might be to go to a small clothing consignment store. Tell the owner you are a crossdresser and shop for yourself there. Make friends with the owner.

Once while walking into a building, I noticed a lady ahead of me wearing a dress that is very similar to a dress that I own. I was looking at how she made it work with her shoes, etc.
We got onto...

I love the cut of that dress! It has some sleeves, it has a narrow neck, no waistline, and it isn't too short. I couldn't do the sheer part, but otherwise, that is my kind of dress!

Joey

I have four stories, but only two turned out to be what they seemed to be.
1) Once I went grocery shopping across town while dressed pretty. I was a man in a skirt. (That's all I ever do.) While...

If you have a Gandalf beard, then "you shall not pass."
<snort>

HEY Bea!

Are you wearing the make up with your menswear or only with your womenswear? If with menswear, can you tell if anyone is noticing or reacting?

Now, go buy your wife flowers.

I go out as a man in a skirt or dress. I never present female. Everyone who looks at me knows everything immediately. It's not so bad. I've gotten over being the oddball, and now I think that I...

I wore a black and white skirt, a black top, a red cardigan and black flats to my doctor's appointment last week. That was my first time. It went fine.

Joey

Recently, once or twice per month, I present male and wear skirts or dresses.

At my peak, I may have gone out four times per month, when I was working outside of the house and became brave/stupid...

I forgot to bring my camera. It was in the car.

I went back in today for the appointment... on the right day.
I checked in. I sat down in the lobby and waited. There were six people waiting.

Eventually, I was called away by a nurse who has...

For us, every month, we distribute cash to each of us. There is pocket money, grocery money, date money, etc. That pocket cash is money that we spend on whatever without a need to ask permission. ...

Thank you for the kind words everyone!

Concerning going the whole nine yards: I don't own a wig, makeup or a bra. I'm just a guy who wears dresses and skirts occasionally. That is "all the way"...

I attempted to go to the doctor's office today while dressed pretty. I present male and wear skirts and stuff.
I was wearing a black and white skirt, nude pantyhose, black flats, a black top and a...

I am becoming more forgetful as I age. I am becoming sloppy. My kids don't know I crossdress. I have forgotten to put stuff up. Once, I left a garment on the floor... I think that I have caught...

Oh yeah.
I'm pretty hard on myself in general...

I had shingles once. Being a crossdresser helped. For me it was on my abdomen. It was painful and a big breakout. I shaved the hair on my abdomen and I wore a tank-top shaper top that kept my...

It is almost a fantasy to think about my wife actually going somewhere with me dressed pretty.

On a couple of occasions, my teenage daughter, who does not know, has looked through my pretty clothes. She hasn't ever asked to borrow any that I am aware of. But, I'm big and old and she is...

When I first started venturing out in public, I wore skin-toned pantyhose with my men's shorts. I felt like everyone could see them. Eventually, I upgraded to wearing women's shorts, sneakers,...

In the first few months of my marriage, I put on my wife's skirt and sweater that she would often wear. She was there. Somehow, it became an idea that I would go check the mail while dressed like...

? Have you ever wondered why you like to dress like a woman?
Of course.

? Do you believe you were influenced in childhood or adolescence?
There was a boy in my neighborhood. His swing set had...

When a salesperson says, "Who are you shopping for?" I think they are really probing to see if you are shopping for yourself without asking a question that might be offensive to a non-crossdresser.
...

John,

People are curious, but we typically want to be polite. Once a conversation or a friendship is started, the opportunity to ask questions is there. After that, your personality opens the...

One time, when I was 25, I "needed" to dress as a woman for a thing. It was a costume, but it was not Halloween. My mom started helping me work on it. She stitched in padding into a bra and added...