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Two Recent Outings

May 8, 2017


For a recent outing, I wanted to wear a beautiful, new red skirt I had bought.  Unfortunately, the skirt hangs only to my knees and my legs are not shaved.  I could not wait until next winter to wear it.  I decided to put on black, opaque tights, the red skirt, and some black flats, with my black top with that has a built-in cardigan.

I went to a restaurant that I had never visited before.  It did not look too busy.  I arrived near 11:00 AM.  The lunch crowd had not yet arrived.  As I walked into the restaurant, the hostess tried not to look down at my skirt.  She did rather well.  She stopped at my waist and returned to my face.  She seated me politely and casually.  I sat, ordered, and ate my food without consequence.  While I ate, people steadily arrived in the restaurant.  Eventually, I walked to the counter to pay.  I stood there for a minute or two while paying and then I left.

Greeting Card Store
Next, I went to a store that sells greeting cards.  I was shopping for five different cards.  Mother’s day, etc.  One employee came to me and offered to help me.  I was pleased that she was willing to offer me help, but I declined.  I did not understand how she could help me select an item that is as personal as a greeting card.

I shopped for quite a while.  The cards I saw typically were at one of two extremes: “I hardly know you, but…” and “I basically worship you and bask in your perfection…”  I also observed that there were quite a few crude greeting cards.  While I was shopping, several customers passed by.  To some I said, “Hello.”  Everyone was polite.  It was a quiet, pleasant shopping experience.

Eventually, I did need some help finding a themed card.  I found the girl and told her what I was looking for.  They had some children’s cards with characters, but the store did not have what I was looking for.

I made my selections and went to check out.  I stood in line waiting to pay.  A woman was in front of me and she was taking a long time.  A man was behind me.  That is it.  A guy can go shopping in a skirt and it can be that non-interesting…  I paid and left.


Toy Store
A few days later, I went to a toy store to get an item for my child (to go with the greeting card).  I have been to this store in a skirt on a couple occasions.  On one occasion, the owner helped me and was uncommonly warm and friendly.  I knew what I wanted to buy on this trip.  I entered the store and went directly to where it was.  The owner was at the cash register dealing with a customer.  The owner saw me and smiled and welcomed me.  While I was choosing between the different versions of what I came for, another customer arrived.  She saw me and politely returned my greeting.

I selected my item.  I decided to walk around the store while the owner was still busy.  Eventually I got in line.  The woman in front of me left and the owner and I completed my transaction.  She offered to wrap my gift.  She talked to me happily and naturally while she wrapped.  It was very nice.  (She was a bundle of sunshine.)

Ice Cream Shop
After I left the toy store, I did not want to change.  It felt so nice feeling my legs rub against one another and my slip.  I forgot to mention what I wore on this outing.  I wore my light orange maxi skirt.  It is ankle-length on me.  I wore a white top with my navy cardigan.  I wore white Keds and some rather new (and therefore good feeling) nude pantyhose.  I felt very good in this outfit.  I think the colors are happy and go well together.

I went to an ice cream shop that I have been to many times in a skirt.  I bought some ice cream and spoke for a moment with the woman who is always there.  She is always very friendly and talkative.  I took my ice cream with me and left.  It was delicious!

Thank you for reading!


From → True Stories

  1. I do find reading about your outings as a man in woman’s clothing to be pleasant and affirming. I can present in my own home but getting out and mixing with the civilian population is really not in the cards. I am a large guy, well over 6′ and build like a linebacker at 260 lbs. I am very well known and recognizable in the community.
    On the other hand I do have my arms and legs free of hair. I have been hair free on my arms and legs for decades and I never have a comment from anyone when I am out and about in shorts, which is often. You should consider shaving for more of the year. My guess is that it will not be noticed when you are in guy mode. As for wearing opaque pantyhose I do wear them in the winter for their style and warmth but when the nicer weather comes around I much prefer the thinner regular pantyhose.

    • I have seriously considered shaving for 12 months straight. However, this is negotiated territory. My wife and I are making this work together, I suppose. It is about our friends and our kids, etc. Now that I have maxi skirts that I can wear when my legs are hairy, summer dressing works. Also, bleaching my leg hairs so that they are less noticeable is useful. 🙂

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