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Lunch, Haircut, and Errands While Crossdressed

February 15, 2020


It had been over a month since my last haircut.  I was looking rough.  My gray hair does not lie down like my dark hair.  I have a Bernie Sanders look when it grows out.  I probably should get it cut every three weeks, but I do not achieve that frequency.  I needed to go to the bank during my lunch break.  I decided to dress up pretty, go to the bank, eat lunch, and get a haircut.

I wore a flowy, black, knee-length skirt with a black, gray, and white patterned blouse.  I wore a new brand of pantyhose called WestLoop.

I bought these WestLoop pantyhose at a pharmacy.  I think they are rather similar to Hanes Silk Reflections.  They are quite sheer.  In fact, I felt like they might not be hiding enough of my legs’ imperfections.  They have a slight shine.  They match my skin color better than almost any hose I have ever worn.  I wonder if this is roughly what Princess Katherine’s pantyhose look like.  In any case, these are so sheer that it is hard to tell that I am wearing them.



The pharmacy’s parking lot was rather full of cars.  I considered not going inside.  A man and then, moments later, a woman left.  I waited in my car for them to be gone.  I got out.  I was met with some brisk wind.  I had to grab my skirt just in case.  This was new!  I should have worn a pencil skirt today!!

I went to the greeting cards aisle of the store to buy a Valentine’s Day card.  There was a well dressed man on aisle.  I was not concerned.  We browsed side-by-side.  He left.  I kept browsing.  A woman came down the aisle and stopped a couple feet away from me.  We shopped side-by-side until I made my selection and walked away.  (Years ago, when in a situation like this, I would have been so distracted that I could not have paid attention to what I was buying.  Indeed, I was self-conscious, but not enough to make it hard to select a card.)  I am sure she must have seen my outfit, but there was nothing in her demeanor to suggest she noticed.

The cashier was young.  She behaved like I may have been her first crossdressing customer.  She was still pleasant, professional, and effective at her job.  However, she seemed affected by it slightly.  I felt like she was not entirely sure how to behave.  I do not know her.  Maybe this is her normal.


While I was entering the bank, a man held the door to let me in.  Both employees talked to me like usual.  I asked the teller to take my picture while I was the only customer.  She happily cooperated.  Another man entered as I was leaving.  He greeted me with some slight hesitance.


For lunch, I went to an Italian restaurant.  This was my first time eating at this restaurant while dressed pretty.  I had to stand at the entrance while waiting to be seated.  There was a woman waiting on a take-out order.  She and I stood there, side-by-side for a few moments.  She told me that she was waiting and that I should go ahead of her.  I told her that I was dining in and was waiting to be seated.

The waiter seated me.  There were two occupied tables.  Two women were dining at one table.  The woman facing me kept talking, but I saw her eyes turn to my skirt as I walked by.  The waiter was not very outgoing, but he did his job well.  I never saw him taking glances at my legs.

I left before the ladies had finished.  I looked to see if the second lady paid me any attention as I walked past their table.  Not even a glance.  I looked back into the restaurant when I was at the door.  No one was looking my way.


I have been to this barber shop a couple times while crossdressed.  I sat in the lobby.   I could see into one of the cubicles where the stylists work.  A business man was receiving a haircut in the cubicle.  He saw me and looked at my outfit while talking to the stylist.  I looked right at him, but he did not notice.  Eventually, after about 10 seconds, he looked at my head and saw me looking back.  He looked away and never looked back.

Each time, I have visited this salon, I have had a different stylist cut my hair.  This time, a man cut my hair.  This may be the first time a man has cut my hair while I was dressed in a skirt.  There was no mention of my outfit the whole time.  We talked a lot.  He was friendly.

He finished.  I stood up and paid him.  Then a female stylist who cut my hair previously came over to talk to me.  The three of us stood in his cubicle and talked for a few minutes.  I was brushing hair out of my black skirt part of the time.  I asked her about how to be a good friend to someone who has a wife with cancer.  (The female barber is in a cancer fight and surviving (she has grown her hair back out to a couple inches (5 cm)).

I saw a man waiting in the lobby to get his hair cut.  I said my good-byes to the stylists so that the man could be served.  Then I walked out of the cubicle, through the lobby, and past the man.

I’m a man who wears a skirt in public, and it is OK.






From → True Stories

  1. Pat permalink

    Being a man wearing a skirt and pantyhose in public really is not a problem.
    We just finished a vacation. Every day I would take a morning walk wearing beige pantyhose under my walking shorts. Most evenings when we went out to eat I again wore my pantyhose under my shorts. Never any issues, even with my wife. I do not recall anyone looking twice at my legs. We took the auto train back from Florida north and I wore my shorts with pantyhose waiting to board the train at the station and again to dinner and breakfast on the train. No issues.

    • In my earlier days of crossdressing, I would wear shorts and pantyhose quite often. I felt like I was so obvious! I have infrequently gone in public like this lately. I have been thinking about doing it again. The joys of wearing a skirt have overshadowed other things, I suppose… Perhaps my wife would tolerate me in shorts and go out in public with me. I need to suggest it!

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  1. Doing Manly Errands in a Skirt | joeypress

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