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Skirted Outing

June 29, 2012

I made arrangements with my wife that I would take a day off to go out of town to have a crossdressing outing.  She is not very comfortable with such things, but she consented.  I left early the day of my outing.  I drove to a town over an hour away from home.  It was a nasty, rainy day.  I was wearing a skirt, blouse, dark pantyhose, and heels.  Like always, I had on my normal man head.  I was a man in a skirt.

My first stop was at a restaurant for breakfast.  I walked into the restaurant and the man who was the hosting only needed a half second to recover from the unexpected scene of me dressed this way.  Then he was completely professional and took me to be seated.  Every time I go out crossdressed, the first few minutes where I am around people are difficult.  He walked me out of the empty lobby down a hallway and into the dining area.  There were people all around.  I was uncomfortable walking into that room, but I had to follow him.  I did it, and some people looked at me, but no one stared.  I ate breakfast with no interesting events.  The server was completely normal with me.  After my meal, the man at the next table and I spoke briefly.  I could not tell if he noticed anything unusual about me.

The next thing on my agenda was to go to get my hair cut.  It took me some effort to find the place.  I parked as close as I could and hurried through the rain to the salon.  I was the only customer and was seated immediately.  The woman working in the salon did not react directly to my being crossdressed.  She was friendly with me, but she was not warm and “natural” like some people are.  I think she wanted to cut my hair and get me out the door before her next customer came in.  Regardless, I did it!  I went to the barber shop while wearing a skirt!

After the barbershop, I did not know what to do.  It was still early and most businesses had not opened.  I went to a bookstore that I now consider a sort of hippy hang out.  I basically walked in and looked around and left five minutes later.  One notable thing that happened was that I spoke to another customer.  I saw a woman looking at books and I decided to ask her for ideas of things to do in town.  I had already asked the waitress and the barber.  I did not want to spend my day walking around the mall.  I approached the woman and said, “Excuse me.  I am here in town for the day.  What are some things I can do while I am here?”  The woman, who appeared to be in her middle to late 20’s, gave a few suggestions.   I thanked her and moved on.

Later, an old indoor shopping center opened.  I went there and shopped around.  Nothing very interesting happened here.  When I was leaving, I heard someone call to me.  I did not expect it.  I doubtfully looked back to see if it might be for me.  It was the woman from the book store.  She was calling to me.  She was in the same shopping center and happened to see me.  We started talking.  She thanked me for talking to her earlier at the book store.  She seemed nervous.  We started talking and I suggested we go sit down at the nearby open air cafe in the building.  We sat at a table and talked for a few minutes.  Just to be clear, this was nothing like a date.

The woman turned out to be 19 years old.  I had no idea she was so young.  I came to realize that this young girl was sad and alone.  She had started to isolate herself from outside people.  Therefore, people did not normally talk to her.  Me talking to her in the book store had really meant a lot to her.  She seemed to be completely disinterested in the fact that I was crossdressed.  Furthermore, she did not seem to mind if everyone in the mall saw her sitting with me.  Eventually, I realized that my parking meter would have already expired and I said good-bye and ran to my car as fast as my heels could take me.  The meter had expired, but I had not received a ticket.

I walked down the street from there and visited a few shops.  I visited a nice dress shop and tried on a couple things.  The girl working the shop was completely warm and friendly.

At the mall, it was crowded.  There were a lot of young people there.  I have grown to dislike being around young people while I am dressed up because I do not want to be photographed and posted on their social network.  I did not stay at the mall very long.

After that, I went home.

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From → True Stories

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