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Lunch and Grocery Store Outing


For this outing, I happened to wear a just above the knee, black business skirt.  With it, I wore a red top, black pantyhose, and black flats.

Again, I went to a restaurant I have frequented for years.  I walked into the restaurant.  The regular hostess was working.  She never looked down from my eyes.  She asked me if I was there to eat in or out (because she knows I often do either).  I told her I wanted to eat in.  She led me to a table.

I arrived early because I wanted to avoid a crowd.  I was the only customer in the restaurant.  A server came and took my order.  She knows me as well.  I think I detected her glance down at my feet or legs under the table as she approached.  She might have glanced at the table.  Other than that, I saw no indication that she was even aware that I was crossdressed.

She brought my food and I ate it.  No customers arrived during this time.  I went to the front counter to pay.  The server brought my check to the cashier.  Again, no one treated me any different, no glances down, etc..  There were several servers gathered near the hostess station.  Maybe they were there to look at they guy in a skirt.  They did not stand there and gawk at me or whisper or giggle.  They were talking to one another and barely acknowledging my presence.  I waved good-bye to them as I left.  Perhaps one of them noticed my farewell.

Grocery Store
I was craving some candy (and I did not want to quit my outing).  I drove to a grocery store.  I got out of my car, adjusted my skirt and walked in.  I used to be SO afraid at this point in an outing.  I would sit in the car and gather my strength.  Those days are apparently fading away.

I honestly found a parking spot, opened my door, and walked toward the store.  A man was parking shopping carts inside the store when I entered.  He welcomed me.  I walked across the front of the store to the aisle I was seeking.  None of the several cashiers or customers paid my any attention.  I walked to the back of the store.  I got some milk to go with my candy.

I walked across the back of the store looking for the candy aisle.  At one point, I crossed paths with a woman who was talking on her phone.  She was walking toward me and never even glanced my way.  A couple other customers never glanced my way that I could see.  Sometimes they were behind me.

I browsed the candy aisle.  Another woman was on this aisle.  We did not interact.  I went to the cashier.  There was a customer ahead of me.  When I was in front of the cashier, he never had a chance to see my outfit.  I bought my items and I left.

I honestly could not tell if anyone even noticed my outfit.  I am sure some of them did.  Perhaps only after I had past them.  In any case, it seems like a man in a skirt is simply unremarkable these days!  I am OK with that.




Breakfast Outing


I went to breakfast today.  I wore a simple white top with my blue maxi skirt with the white horizontal accents.  I wore white canvas sneakers.  It was a simple, comfortable outfit.

I went to a restaurant where I had to place an order with a short order cook.  A woman who has served me several times was taking orders.  She took the order of a woman who was ahead of me while I waited.  Then, she took my order.

Next, I walked over to the cash register and the same employee took the money of two people ahead of me and then she took mine.  There was no one behind me.  We ended up talking for a minute or two.  She is unconcerned about how I dress.  Other customers arrived and I went to get a fork and napkins.

I received my food and I ate it while watching the news.  Another man entered the dining area soon after me.  He sat a few tables behind me.  A few people came in and left, but none of them paid me any attention.  After I finished, I deposited my trash and exited.

Shortly after exiting the building I realized that my money and ID were missing.  I turned around.  A woman who was working in the lobby said, “Back so soon?”  I collected my pocket thing from the table and reattempted to exit.

A woman in a blue dress was exiting shortly behind me.  As I walked on the pavement, the woman picked up her pace.  I could hear her shoes.  She was catching up to me.  I wondered if she was going to try to speak to me.  She did not.  I think the cool morning air made her want to hurry to her car.  She, like everyone else, was unconcerned about me and my business.

As it should be.


Lunch and Shoe Shopping


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…)

Lunch and Grocery Shopping


Many years ago, I did our family grocery shopping while wearing nude pantyhose and shorts.  More recently, I have gone to far away grocery stores while dressed pretty to do our family grocery shopping.  I’ve done it a couple of times in a skirt or dress.  This trip, I went to a nearby grocery store wearing a pair of black womens shorts and nude pantyhose with my men’s socks, shoes, and shirt.  It was a rather inconspicuous outfit.

First, lunch.  I went back to the restaurant that I recently visited when I was dressed in a skirt.  This was my first return to this restaurant since these people (who see me often) learned that I sometimes wear a skirt.  I was curious to see if they would behave differently toward me.  They did not treat me any differently.  I doubt they noticed that I was wearing anything unusual on this visit.  It was a delicious and uneventful meal.

Something was wrong with the cash register and I had to wait on a manager to help the cashier.  So she and I talked briefly.  While we were speaking, a couple waitresses interacted with us.  All of these ladies were working these same jobs when I came in a skirt.  They all almost certainly saw me wearing the skirt.  I detected no difference in their behavior.

Grocery Shopping
I did not go to my normal grocery store because I feared the risk of seeing someone I live near would be too high.  I did go to another store that was not very far away, however.  I had a shopping list and I did my shopping.  I did not try to hide behind my shopping cart as I did many years ago.  I did try to catch myself doing the opposite.  I found that I was more likely to step out from behind my cart when people were around.  I did not like that.  I intentionally stopped myself from hiding or from modeling.  I insist on behaving normally!

Ultimately, as I expected, no one noticed anything unusual about me.  I did my shopping without fear.  No sweat stains were on my shirt.  I have become pleasantly comfortable while dressed in public.  When, it was time to check out, I discovered that there were lines at every cash register.  I got into line and waited.  Eventually, a woman got in line behind me with a shopping cart and only a few items.  We waited for 5-10 minutes.  Eventually, I was out the door.

While I was loading my car, the woman who was behind me in line came out and approached the car beside mine.  I spoke to her, “Are we neighbors again?”  We talked while loading our cars.  She dropped a dime and I told her and picked it up.  She was the only person who would have reasonably noticed my outfit.  She gave me no indication that she noticed anything unusual.  We said good-bye, and went our separate ways.


Lunch and August Haircut


I went on an outing today.  I wore a black knee-length skirt, off-black pantyhose, black flats, and a gray and black top with 3/4 sleeves.  Otherwise, I was just my normal man self.


I returned to a restaurant with a short order cook that I have visited on several occasions in men’s or women’s wear.  I was behind the counter when the man took my order.  I was not hidden from the very few customers.  I went to the cashier to pay.  She knows me.  We talked for a few moments.  She is unconcerned by my fashion choices.  She is always polite and welcoming.  I estimate that she is about fifteen years older than me.

Normally, I happen sit near the cashier area.  As is usual in my experience, once I am seated in a restaurant, people do not notice my outfit.  They cannot tell I am crossdressing.  This time, however, I sat in a new location.  I sat near the television while I ate.  The news was on.  Sitting in this position placed me in the path between the door and the short order cook’s counter.  People came in and out of the restaurant while I ate and watched television.  They walked past me.  I felt like I was more visible being seated by the aisle.  I mostly paid them no attention.  I never noticed anyone paying me any particular attention.

After my pleasant breakfast, I had tasks to perform in my guy clothes until lunch time.


For lunch, I did something quite daring.  I went to a restaurant that I have eaten at in my normal menswear dozens of times.  I sat in the parking lot for a minute or two deciding whether I really wanted to do this.  The staff have come to know me.  They know what I order.  I am a regular.

This is not my first time wearing pretty clothes here. However, this is the most bold outfit I have ever worn.  Previously, I have worn womens slacks with dark hose and flats.  Also, I have worn shorts and nude pantyhose on two occasions.

I walked into the restaurant.  Another customer was in the lobby waiting on a TOGO order.  I considered hiding behind her.  Instead, I stepped to the side where the hostess could see my full outfit when she came into the lobby.

The hostess was a server who has served me and spoken with me several times.  I did not even see her glance down.  She invited me to follow her and she seated me.  She verified my usual order and walked away.  I wondered if she was less personable than usual.

Before, when I ate here in women’s slacks, etc. the male waiter who served me noticed my shoes and looked down at my feet very carefully twice to get a good look.  Today, he walked by and did the same thing to my feet in this outfit.

No one else seemed to notice anything unusual about me, including the customers.

I finished eating and walked to the cash register.  A woman who is the normal hostess came to take my money.  Again, I could not tell if she noticed anything unusual about me.  A couple other staff were talking across the lobby where they could have seen me.  I did not notice them paying me any specific interest.

I wished the woman who took my money to have a good day, and I left.  It felt really good being treated like nothing was unusual about me visiting the restaurant while dressed in a skirt.  It was delightful.  (I assume that you the readers are growing tired of my uneventful outings.)

Barber Shop

I returned to the same barber shop that I visited last month.  A man was approaching the entrance at the same time that I was.  I opened the door and intended to allow him enter first, but he offered to let me go in first.  I walked in, and signed my name on the sheet.  A woman and her adult son were waiting in the waiting room.  I sat down.  I could not tell if anyone even noticed my outfit.  Everyone was accepting me casually.

The young man was using his phone a lot.  He truly could have never looked up to see me.  At one point, however, I noticed him tilt his phone toward my feet/legs.  He took a picture of me, I think.

Two customers left.  Then the two employees came to the waiting area at the same time.  One called back the young man.  The other employee called me back.  We were served in separate rooms.  The woman who cut my hair never acknowledged my outfit.  She never seemed to look at it.  She never seemed uncomfortable.

We talked about various topics.  She finished cutting my hair.  I paid her and I left.

When I got in my car, I just sat there for a moment and enjoyed it all.  I just went to a restaurant where I often eat.  This time, I went for the first time in a skirt.  I got my hair cut.  In both instances, I could not detect any concern or distraction.  I simply had an excellent time.

Shorts Outings

Recently, I had some outings where I was wearing all men’s wear with the addition of nude pantyhose.  I have felt empowered to show my legs again thanks to how my leg hairs are bleached and are, therefore, hardly visible.

Date With My Wife
While I was out on a “date” with my wife, we went clothes shopping.  I was wearing nude pantyhose under my long pants all evening.  However, at one point, I came out of the dressing room wearing a pair of shorts.  I wondered if my wife would be upset that I came out of the dressing room into the open area wearing pantyhose and shorts.  I knew that when I left her, no one was around.  I came out, she gave her comments about the clothes, and I went to try on the next outfit.

She did not notice.

Lunch Outing
During work one day, I went out to lunch.  Changed into shorts in my car.  I went into the restaurant walking past two people in the lobby.  I stood at the counter.  I placed my order with the short order cook.  No one noticed that I could tell.  I paid.  I waited.  I received my food.  I got my eating utensils.  I did everything like normal.  No one appeared to pay me any unusual attention.  (I have eaten here before in a skirt.)

Another Lunch Outing
Once again, I ate lunch out in shorts and nude pantyhose.  I have been to this restaurant several times.  The staff recognize me.  I was daring (or misguided) enough to do it in shorts and pantyhose.  I arrived and was promptly seated.  I ate, paid, and left.  If anyone noticed my outfit, I could not tell.

Yet Another Lunch Outing
On another day, I returned to the second restaurant.  I ordered my food to go and stood at the lobby waiting.  Again, I could not tell if anyone noticed anything unusual.  No one acted like it was different.

Road Trip


I went on a day road trip.  I wore my new, blue and white striped, maxi skirt.  I also brought a white button up top, a white t-shirt, nude pantyhose, and white Keds canvas shoes.

I stopped at a restaurant that has a store attached to it in order to buy some candy.  I parked rather far from the door and walked in.  I was wearing sunglasses.  I do not know why that is important, but it was a different experience.  I walked up to the restaurant where a few people were sitting outside waiting.  One of the people looked like a 20-year-old girl.  She smiled, but she was not smiling politely at me.  I might be wrong, but it looked like she was containing her laughter.

Inside, I removed my sunglasses.  The staff was polite and professional.  The customers were also polite.  I found my candy and bought it.  I walked back out past the porch people and returned to my car.

Grocery Store
Next, I stopped at a store to get some milk to drink with my candy.  The store was rather busy, but I was not afraid.  I walked in with my head up.  I was impressed with myself.  I walked past a lot of people.  Many of the people never noticed me.

I selected a cashier who was smiling more happily than the others.  I got into her line.  She was dealing with another customer.  When it was my turn, she seemed very reserved.  I suppose I may have made her uncomfortable.

Clothing Store
I drove for about an hour in my skirt eating my candy.  It was very nice.  I stopped at a clothing store and shopped for a few minutes.  I noticed that all of the mannequins had either patterned tops and solid bottoms, or they had patterned bottoms and solid tops with necklaces.  Only one solid top did not have necklaces over it.  That top had ruffles that went diagonally across.

So, I received the message: I need to break up the plainness of a solid top.  I asked an employee how I could accent my solid-patterned tops without jewelry or scarves.  She gave me some options that were similar to what I already do: wear jackets, sweaters, or cardigans.

I changed back into trousers before getting to my destination.

Rest Area
A couple hours later, I was on my return trip.  I changed clothes back into my skirt and continued driving.  I stopped at a rest area and used the men’s room.  There were two options for which men’s room I could use.  I heard someone in one room.  I hesitated briefly and then went into the other men’s room.  I used the rest room in solitude.  I felt like I had acted cowardly.

Several Stores
Eventually, I stopped in a small town.  I shopped in a clothing store.  Then, I bought some gardening supplies at a hardware store.  Next, I went to a small grocery store for another small bottle of milk..  They did not have small bottles.  Nothing significant happened in these places.

Fast Food Restaurant
Next, I went to a fast food restaurant for a milkshake.   At this stop, things were somewhat uncomfortable.  I walked across the parking lot and approached the door.  A family was exiting the restaurant.  Through the glass, the teenage daughter in the family saw my outfit and started laughing.  Her mother and grandmother did not laugh.  They also did not tell her to stop being rude.  I held the door for the women.  The mother was providing a lot of physical support to the grandmother.  Both women thanked me politely as they slowly exited.  While they progressed past me, the girl, who was behind them, was using her hand to hold her face.  The teenager eventually gained her composure when she finally exited the door that I was still holding.  She straightened her posture, looked me in the eye, smiled at me and said, “Thank you.”  I replied.  I entered the restaurant and glanced back at the family.  The teenager was laughing again.  Her family members still were not laughing.  I was not affected by it.  It did not shake my confidence.  I just felt that she was young enough that she could not manage to respond to my outfit in a casual manner.

Let me add that more than half of the people did not react to me.  They seemed mostly disinterested in this anomaly of a man in a skirt.

I got in line behind two men.  Behind the counter, there was a cashier, a male employee, and a tall, female employee.  While I stood there, the tall employee noticed me and smiled and gave me a bright, “Hi there.”  She did not speak to the two customers in front of me.  I noticed some employees back in the kitchen area huddled close and looking at me.  A teenage employee looked like she was laughing.

I ended up ordering food and water to go with my milkshake.  I paid and walked over to the drink area.  A male customer was refilling his drink.  He walked away and sat by his female companion.  I heard him try to tell her about me in hushed tones.  When I walked past their table on my way to the exit, I looked their way.  The woman seemed uncomfortable.

I was not made significantly uncomfortable by their reactions to me.  I had a nice outing.

Shopping Center
Next, I drove to a different town.  I stopped at a shopping center.  I walked to a store that had a blue jean skirt in their display.  A male employee was at the entrance.  I felt awkward, perhaps he felt awkward as well.  We said hello and I walked on shopping.  Eventually, I walked over to him for help.  I could not find a knee-length denim skirt.  He started helping me like normal.  Eventually, he called in a female employee.

They did not have skirts as long as I was seeking.  The three of us continued speaking briefly.  I walked toward the exit.  The female employee walked away.  The man kept talking to me.  Eventually, the conversation ended and I exited.  I was surprised that he was slightly difficult to get away from.

Gas Station
My last stop was to a gas station.  I filled up my car.  No other cars were there.  I saw the woman working inside looking out the window at me.  I finished with the gas.  I went into the store and bought a small bottle of milk.  The employee was social with me.  Then, I went home.

My Impressions
As usual, many people either did not notice my outfit or they did not react beyond glancing down.  However, I perceived that the people in these small towns were not used to men dressed like me.  I do not know why anyone in my town would be more accustomed to such things.  The demeanor of the people I encountered seemed more surprised or uncomfortable than I usually observe at home.  Whatever it was, it was subtle.

When I first started going out in public wearing women’s wear, I normally felt like the people who saw me were shocked or uncomfortable.  However in the past few years, I have stopped noticing such reactions.  I concluded that one of two things were true: either I was not paying as much attention to peoples reactions, or the general public where I normally go out is less shocked than they used to be at seeing a man in a skirt.  After this experience, I think that the difference was not me.  I think people are more at ease with a crossdressed man.

When I typed up my experiences on this outing, I started noticing a pattern.  I wondered, “Were people laughing because my outfit was unusually silly looking?”  I had to reassure myself that I did in this outfit what I often do in a new outfit.  When I was being helped by sales people in the clothing stores, I asked, “How can I make this outfit better?”  With this outfit, I received higher compliments than I normally receive.  I do not recall any suggestions for improvement from the two women I asked.

Thank you for reading about my silly experiences.