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First Time Crossdressing In Public

April 3, 2019


I have not had many crossdressing outings this year.  Work and life have consumed very much of my time and energy.  This past Sunday, March 31, was the Transgender Day of Visibility.  I would have liked to have gone out in public.  Last year, I went grocery shopping and went to church.  It was not possible this year.  On Monday, I looked on-line for pictures, videos, or stories of people going out on Sunday.  I found nothing from this year.  I read people’s “first time out” stories instead.

That inspired me.  Here is my first time out story:

It seems hard to select which was my first time out in public.  There was that time I wore some of my mom’s shorts in front of Grandma.  There was that time that I walked around the outside of my house at night wearing something pretty while I was home alone.  There was that time I wore nude pantyhose when I went for a jog.  None of those experiences seem sufficient to be my FIRST TIME.

Just to be clear, when I go out in public, I present male.  I just like to wear women’s clothing.  Some of the following stories might not make sense if you thought I was wearing make-up and a wig, etc.  In all of the following, I am all male, in nice clothes.

First time being seen

My first time wearing something feminine in front of other people was when I went to a lingerie store far from home and bought a pair of “Man-T-Hose“.  I asked the employee if I could go put them on after buying them.  I came out of the dressing room wearing them under my shorts.  I did not have the nerve to wear them out of the store.  No one would have noticed, but I did not realize that.  That was a very contained, but rather scary experience.

First time in public in dark pantyhose and shorts

Over time, I had many shorts and pantyhose outings.  I cannot remember the first one.  Sometimes, I went out in all women’s clothes with shorts and nude pantyhose.  One day, I wore dark pantyhose in public under shorts.  I went to a restaurant and several stores.  People took obvious glances at me.  I learned that no one had noticed me in the nude pantyhose previously.  It was so frightening and so exhilarating to be out of the house and not in hiding.  I was surprised at how it was not a bigger event.

First time in public in a skirt

Up to this point, I had tried on skirts, etc. in stores and I had been seen by the employees.  I had also worn a dress in public for a costume.  Those do not count as my first time in a skirt in public, however.  On my first public skirted outing I wore a skirt to several stores and then to the mall.

I visited a store.  It took SO much nerve to get out of the car and go in.  The employees in the store acted like it was not a big deal.  I shopped and spoke with the employees.  I even took a picture with an employee.

skirt outing

Then, feeling emboldened, I went to a shopping mall and walked from one end of it to the other and back.  That was so difficult.  I was horrified.  There were only a few reactions that were noticeable.  A few were negative.  No one else seemed to notice or care.  I was so brave that day.  These days, it is nowhere near as difficult to go to the mall in a skirt.  But that day, it was a major achievement!


Yesterday, while I was reading first time stories, I saw a few stories that I did not believe.  Maybe I am wrong, but those stories seemed bogus because they were too successful and significant.  In my experience, believable first time stories include profound fear, an insignificant amount of exposure, and no one interacting with the dressed up person (unless it was at a party or with a supportive friend).  If the story includes great success on a long, very public experience with compliments or physical interactions, I highly doubt the truth of that story.

From → True Stories

  1. same. I had a full year and a month not going out. I had a short diner in Jan and Feb. Work has really collapsed my outings to date.

  2. Pat permalink

    I agree that we may all have multiple first time stories. The first time you do anything new while dressed is a first time out. Like you all of my ‘first time’ events carried a significant element of fear and I do not delude myself into thinking that anyone perceived this very large, well dressed persona as a woman.

  3. Reblogged this on A Crossdressing Tapestry and commented:
    It has happened to me also.

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