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Lunch and Shoe Shopping

September 10, 2017


For this outing, I wore my green, brown, and black abstract patterned skirt with my brown top.  I also wore off black pantyhose and black flats.  As  always, I was just a man dressed in a skirt.

Sit Down Restaurant
I went to a fancier than normal restaurant for lunch.  I think I was in the mood to have a server.  I was seated by an adult man.  I assume he was the manager.  He was polite and welcoming.  He did not glance down.  He seated me at a table near the restaurant’s bar area.

A woman in her twenties was behind the bar.  She saw me being seated.  I saw her look me over in a glance.  She turned out to be my server.  When she came to say hello and get my drink order, she was relaxed.  She was very professional and friendly with me.  I, however, was not feeling very confident.  When she returned with my cup of water, I asked her, “Do I look silly?”

She smiled and started reassuring me saying, “You hold your head up and own it.”  She immediately sat down for about two minutes and told me about her cousin who transitioned into a woman full time.  She said that when he became she, it was hard for some of the family to accept.  Eventually love and family outweighed the transition.

She never answered my question (grin), but she made me feel braver nonetheless.

After I ate, the server took my money and I walked out of the restaurant.  Only a few other tables were populated by then.  Probably only one other customer saw me.  I did not look back to see her reaction.

Shoe Store
I needed a new pair of men’s running shoes.  I walked into the shoe store.  A man was sitting, waiting on his wife I presume.  I looked him in the eye and told him hello.  He looked me over and tried to stoically reply, per etiquette.  I had the impression that he would have preferred not to have had to speak to me, but he did.  I was not stressed by having to face a man who was not welcoming.

I went to the back of the store where men’s athletic shoe were located and started shoe shopping.  There were very few other customers in the store.  I only saw one employee.  I browsed for ten minutes.  I found some shoes to try on.  I walked around in them.  During most of this process, I saw nobody.  I eventually put my shoes back on my feet and went to pay.

The man was no longer sitting in the front of the store.  The cashier was a young woman.  She might have been unaccustomed to men in skirts, but she did fine.  I cannot imagine that someone working in a shoe store would not have regular crossdressing customers…

Dress Store
At this point, I was done shopping.  However, I was not done having an outing.  I went to a dress store that I love.  An employee came up to me and started trying to help me.  I confessed to her that I was not really shopping for anything.  I was just visiting because I love her store.  She spent several minutes with me.  She answered my questions and gave me helpful pointers.

The end.
(I should learn how to add insightful endings to my stories…)


From → True Stories

  1. I do enjoy reading about your travels and outings. As you have progressed to have a few more outings, or at least a few more writings about them now, I too have progressed and do more outings. For the past few years I have been wearing women jeans whenever going out with jeans on. Recently I have added ladies shorts to my attire and on a few occasions I have worn pantyhose under my shorts and almost always do under my jeans. With reading about your outings, I have recently worn black flats along with my hose and jeans. So far there has been no comments. I do sometimes wish I could take a picture or two when I do go out but am just simply afraid of being outed and having too many family problems. Someday ……
    I would also say that I do love your pictures when you post them as they give me courage to do more also. Have a fantastic day and please keep posting.

    • Thank you for your kind words (and for even bothering to read my posts)! I assume you are dressing like this while presenting male. People may not make comments. I have worn skirts in public as a man and people try to pretend not to notice.
      I do feel a certain pressure to try and post pictures of myself on my outings. I have a policy of not taking pictures of me crossdressed with my phone. I do not like the security risk of a camera with communication abilities. Also, I do like being able to take an SD card out of a camera and writing zeros to every byte on the disk. No, really, I’m not paranoid! 🙂

  2. I understand. and am very unsure about using my phone for pics especially since somehow one got sent to my son and caused all kinds of scrambles. I do have aFB page that has some photos and comments. Although I am very cautious about posting and using that too.
    I like you thought about an SD card from a camera. I am going to have to look into that. So when you do use that do you download and then post?

  3. Pat Scales permalink

    I think that the lady who sat with you in the restaurant believed that she did answer your question and that her answer was ‘No you do not look silly’. She sat with you to raise your self esteem as a person.
    While for many like us women’s clothing, such as pantyhose, have an almost mystical quality and being out and about while dressed evokes fear and happiness at the same time, for regular women it is just clothing and it does not hurt anyone what you choose to wear.
    Her act of sitting with you and telling you to own it was affirming of what you were wearing, how you looked and who you are. Take it as the ultimate compliment.
    BTW, Sunday night I went out for takeout again and wore my beige pantyhose under my shorts. No comments from my wife. I still do not know if she noticed it and did not care or cared but chose not to comment. It could be that she is so used to seeing me around the house in my hose that it is becoming ‘no big deal’.

    • The first time I went out in public with my wife while wearing shorts and pantyhose, we were far from home. She did not notice for a long time. Eventually, she asked, “How long have you had those on?” It is not easy to see skin-toned pantyhose if you are not looking for them.

Trackbacks & Pingbacks

  1. A Day Visibly Crossdressed on TDoV | joeypress
  2. All Day Outing In A Skirt | joeypress

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