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Flying Pretty Outing – Part 3

October 11, 2017


This is part 3 of a series of posts about a trip I went on.


In the morning, I put on a black skirt, a red top, my black flats, and off black Leggs Sheer Energy Active Support pantyhose.  These were not as tight or as pretty as the Hanes Smooth Illusions pantyhose.  (But they were still tight and pretty.)  I felt good about my outfit.

I went downstairs to go to breakfast.  I passed that man in the hall again.  In the lobby, I found the “continental breakfast” was not very inspiring.  I wanted something more significant than cold cereal, fruit, and waffles.  There were two men eating breakfast.  I basically ignored them and filled a cup of orange juice.  I returned to my room.  On my way, I passed that man again as he came down for breakfast.

I collected my belongings and checked out, without incident.  I might have passed that man one more time.  I am not sure.

I went to a nice restaurant for breakfast.  I was rather early.  There were very few customers.  No one paid me any attention.  My server was nice.  After she brought my meal, I asked the server if she would take my picture.  The food was delicious.  I ate eggs, bacon, toast, and juice.  I quietly ate my meal.  I paid and left.

Breakfast in a restaurant.


Grocery Store
It was so early, I started looking for something to do.  I visited a grocery store and got some things I needed.  Nothing really happened there.  Then I drove on and saw a shopping mall.  I thought, I will be a “mall walker!”

Mall Walker
A mall walker is someone who goes to the shopping mall to walk for the sake of exercise.  Some people do it early before the mall opens for business.  I have always wanted to be a mall walker while dressed pretty.  (I suppose I have sort of done it once in shorts and nude hose.)  I put on my men’s tennis shoes and went inside.  All of the shops were closed.  I started walking.  There may have been twenty other mall walkers.  Most of the other walkers were senior citizens.  I believe all of the other walkers were older than me.

People would greet me.  When I would pass someone, they would speak politely.  Once, I had a brief conversation with someone.  Later, I asked another man how long is one loop.  He said, “About a mile.”  I thanked him as I continued on, passing him.  Then, he started talking to me more describing specifically what I had to do to get a mile.  I thanked him again.  He could have stopped the conversation with a weird man in a skirt, but he did not.

I loved being a mall walker!


After I walked two miles, I took a few pictures.  This is the best one.


Dressed in Menswear
I went to my car and changed into menswear.  I had business to do that day that I intended to do in pants.  However, I considered doing my business in a skirt.  In retrospect, I think it was the right decision.  The people I traveled to work with might have communicated back to my home and exposed my fashion choices to people I choose not to share it with.

After my business was complete, I visited a college campus.  I did not bother to change into my skirt.  There was some kind of event going on on campus.  There were a lot of students and adults in dresses and suits.  I think 5-10% of the women were wearing either nude pantyhose.  Some others were wearing opaque black tights.  I wonder if a professor suggested that dress code to them.  I started wishing I was dressed pretty.

I visited a presentation room.  There were students at tables presenting their groups.  At one table, a group of LGBT engineers were presenting.  I spoke to them briefly.  At one point, I mentioned that I was a crossdresser.  They said that there was a guy at the university who wears skirts and dresses all the time.  At this point, I decided to go change back into my skirt.


From → True Stories

  1. Pat Scales permalink


    I have just caught up to part 3 of your flying pretty adventure and look forward to part 4. I am so happy for you that everything went well. Every time one of us, whether dressed completely or only partially in women’s clothes gets out to the civilian population it is a good thing for every one of us.

    I used to travel more than I do now. Back then it seemed like the only time I could dress is when away on business since the kids were still in the house. I had several travel bags that would contain complete outfits. Sometimes I would get out of the hotel room, other times the risk was not worth the reward. Now that the kids are gone I can dress around the house. Getting out has been the issue.

    I think that the conundrum you will be facing is one that I had to deal with after my trips. I always sensed that my wife knew that I took a stash of woman’s cloths, shoes and makeup on my trips. This was especially true when I had long work related car rides. (there were even times when I would drive pretty) but for the most part my cross dressing was a bit like the elephant in the room. If it was not discussed it would not create a problem. Sort of a DADT ignorance is bliss attitude. Nevertheless I did give a lot of thought to broaching the subject that I did dress when away on business but I always lost my nerve and felt that relating my dressing to her would cause her to worry and I never want my wife to worry any more than absolutely necessary.

    Keep on keeping on and let me know what you do decide to share with your wife.


    • My wife always asks me after I go on a trip about what happened. She does not love it, but she wants to know what I did. I probably give too much detail and with too much excitement. Normally, my outings are rather boring. I do not do very interesting things… In any case, I am rather happy afterward and it probably shows in my descriptions.

Trackbacks & Pingbacks

  1. Flying Pretty Outing – Part 2 | joeypress
  2. Flying Pretty Outing – Part 1 | joeypress
  3. Flying Pretty Outing – Part 4 | joeypress

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