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Very Social Outing

October 7, 2019


For the past year and a few months, my schedule has been fuller than usual.  It has been tougher for me to find time to go out crossdressed.  I had a scheduled meeting with a person who knows that I am a crossdresser, so I decided to wear something pretty on my next visit.  Therefore, it would fit into my schedule.  I wore my beige skirt, a black and white striped top, a black cardigan, and my black flats.  Unfortunately, I did not remember to take a picture of myself.

Meeting With Coach/Consultant

I have been meeting with a sort of coach for about a month.  I am trying to learn how to do something, and she is helping me.  On our first meeting, I decided to mention that I was a crossdresser.  She did not seem terribly surprised or interested.  For this meeting, I decided to wear something pretty.  I did not give any warning of how I would be dressed.  In fact, I never considered it.  I just showed up in a skirt.

In the lobby, there was another customer.  He and I said hello and had no more conversation.  We both sat there for a couple minutes, silently.

My coach showed up and said my name, and I left the lobby.  We spoke in the hall briefly, and then went to her office.  I sat in a chair and we started our meeting.  She never mentioned my outfit.  As far as I could see, she never even looked at it.

Then, for the first time in my life, I talked for an hour with a woman who knows me (other than my wife or a sales person) while I was dressed pretty.  I would say that was rather unusual.  However, it was normal, boring, and perfect!

After our talk, I returned to the lobby and settled my account with the receptionist.  There were a couple of other customers in the lobby.  I did not pay any attention to them.  I was so comfortable in my outfit, I felt like it was not unusual.


It was after 2:00 PM when my meeting ended.   I went to a Taco Bell for a quick lunch.  There were only two other customers in the restaurant.  I noticed a couple glances down by employees.  They were smiley and friendly.  I watched them.  They did not tell the other employees about me.

I ate my lunch in the restaurant.  There was only one other man in the room.  He was eating alone at another table that faced where I sat.  He never even looked at me.  I was feeling very confident.  I started eating my food.  I realized I needed some napkins.  I got up and went across the room to get some napkins.  When I returned, I think the man took his first actual look at me.  I saw that he noticed my skirt.  He never looked at me again.


I walked into my bank.  I have been here before while dressed pretty.  There was a new teller at the counter.  He is the first male teller that I have ever seen at this bank.  All of the other employees who know me called out to me from their offices, and waved, and said hello.

One teller that I have seen before was wearing a fancy, form-fitting black dress.  She was not dressed as a bank teller, she was dressed like a high-end realtor, or an anchor on ESPN SportsCenter.  Normally she wears bright colors and pretty fashions.  This time, she was extra sharp looking.

I did my business with the new teller and then I left.

Consignment Shop

As often is the case, it was time for my outing to end, but I did not want to stop.  I went to a consignment shop that I occasionally go to.  I went there in order to say hello to the owner.  I walked into a busy room.  I did not care, I just walked on in and said hello.  The owner said hello and came around and gave me a hug.

A customer walked by me and said, “That’s a cute skirt.”  (That was a pleasant surprise.)  I looked around the room at one point.  There was an elderly woman sitting in a chair with her walker in front of her.  We made eye contact, and she smiled and gave me a wink.  (That was a surprise too.)

The owner became free and I told the her what happened on the outing when I went swing dancing.  I also told her about my recent visit to a church.

I did not do any shopping and I did not change clothes.  I wanted this to be a quick, social visit.

Ice Cream Shop

I still did not want to end my outing.  I decided that I would go to an ice cream shop and get me something sweet to eat before returning to work.  Near the ice cream shop, something was happening at a car at the intersection.  There were several people there who did not look like they were together.  I kept on driving.

At the ice cream shop, I went in.  There were several customers.  I stood at the counter waiting.  A man from the event at the intersection came in.  I ordered my ice cream.  I asked the man what had happened.  He said a woman was sitting on the side of the road crying.  He was walking from his hotel to the ice cream shop when he stopped to help her.  He said he left her in order to go get her some water.  When he returned, another woman had stopped her car to help.  I received my ice cream, I thanked him for caring for the woman.  He said, “That is what we are supposed to do for one another.”

I got a spoon and some napkins and sat down.  A few minutes later, he walked up and asked if he could join me.  I welcomed him.  His first question was, “How do you identify?”

I was not ready for this question.  I absentmindedly said, “I don’t know… normal?”  That was rude, because that means that anyone who is not like me is abnormal.  I think I followed up with, “I’m just a boring dad.”  He had previously said he was walking from the hotel to the ice cream store, so I asked him where he was from.  California.  We started talking about why he was in my town, and what his work was, and what mine was…  Eventually, I said, “Let’s rewind.  You asked how do I identify.  I am a heterosexual, boring dad, who sometimes likes to crossdress.  I do not do this all the time.”  I asked him how he identifies, and he said homosexual.  Then I thought, “Oh, that’s why he doesn’t mind sitting with an oddly dressed man like me.  We talked about various topics for rather too long.  I needed to get back to work.  I was learning a lot.  Where I live, and perhaps also because of who I am perceived to be, I do not get to knowingly speak to homosexuals very often.  Certainly not about their lives.

I realized that I am rather backward and have a lot to learn.  He was polite and professional.  I say I am backward because I do not have much first-hand knowledge about homosexuals.  I learned that I have prejudices, assumptions, and stereotypes that still affect my thinking significantly.

Eventually, I had to break off our conversation and return to work.  We said our good-byes and parted.

From → True Stories

  1. Pat permalink

    A very interesting day in all regards. Of late my outings wearing pantyhose under shorts have increased. Twice this week my wife and I went out to dinner with my wearing pantyhose under shorts.
    She said nothing and I do not think anyone in either restaurant gave me a second glance.
    A few years ago I was able to get out with some frequency to a few LGBT bars. These were typically on slow mid week nights. I would stop for a drink or two max. I had several conversations with some of the regulars who had never encountered someone like me…an older, happily married, heterosexual, plain vanilla cross dresser. While they understood their own situations and they understood gay drag I think they learned about me as much as I learned about them.

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  1. Meeting, Lunch, and Errands in a Skirt | joeypress

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