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Day Off Outing

February 3, 2017


I took a day off from work.  I arranged with my wife for me to take a road trip to an outlet mall for a crossdressing outing for the first part of the day.  This stuff makes her uncomfortable, but she is still good enough to let me have this liberty.

I had to decide which outlet mall to go to.  I have gone to one outlet mall several times.  The one I have been to is near a city.  The people there are rather liberally minded.  I decided to try a different outlet mall.  This one is in a rural area.  I assume that this town’s inhabitants are as conservative as one would find anywhere in my country.

I dressed in a red a-line skirt, a teal top, off black pantyhose, black flats, long black cardigan.  As always, I was presenting male.  I was just a man in a skirt.  During the day, I asked a clerk for her opinion about my outfit.  She recommended that I should not have worn the teal top.  Apparently, it would have looked better to have worn something neutral with the red skirt.  I am new to dressing in much color.  I geeked out on color, or so it appears…

Restaurant With Store
On my way to the outlet mall, I stopped at a restaurant that has a store connected to it.  I had already eaten breakfast at home.  I was stalling.  I needed something to do for ten minutes to make time for the outlet stores to open.

I browsed around in the restaurant’s store.  A young, possibly 22 year old, female employee came over to see if I needed any help.  She was polite and welcoming.  She told me where the sales were and complimented the [feminine] items she liked.  She left me to my shopping.  I had only entered the store to buy some soft peppermint sticks.  Eventually, I went to the cash register.  There were two women at the cash register, a waitress and a cashier.  I found the peppermints I wanted on the front counter.  The two women talked with me while I paid my bill.  One even pulled out a coin so that I did not need to break a larger bill.

Outlet Mall
At the beginning of an outing, I am normally rather self-conscious.  However, at opening time on a weekday in this outlet mall, there were almost no people to be self-conscious around.  I was so early that not all of the stores were open.  As I was walking along the walkway beside store entrances, I heard a security guard and two store employees talking outside of a store entrance.  They were farther on ahead of me and across a grassy area.  I walked along looking into shop windows.  Suddenly, the three women became quiet.  When it happened, I was looking in a store window.  I looked around and saw them all looking at me.  I smiled and waved.  They waved back and said good morning.

I went to a couple of clothing stores.  Nothing very interesting happened.  The few customers I encountered paid me no attention.  I believe that many of them never saw my outfit.  The store clerks treated me like a normal customer.  One clerk asked for clarity when I mentioned my wife.  I informed her my “wife” was a normal definition of a wife.

Hosiery Store
My only planned stop was at a hosiery, etc. store.  I needed to stock up.  I was shopping for men’s socks, something my wife asked me to pick up, and pantyhose.  I was the only customer in the store.  One of the clerks was unusually knowledgeable about the products.  She was also accustomed to male customers.

Lunch at a Mexican Restaurant
I went to a nearby Mexican Restaurant.  As I entered, I found myself in the presence of about ten people.  A female Hispanic employee and I almost ran into each other.  She seemed to suppress a laugh.  There were a couple customers waiting to be seated.  One, a woman, was facing me and looked up and down at me.  The male employees were completely casual and seated me and served me like normal.

There were three Hispanic men at the table next to where I was seated.  They turned to see me approach, but they did not stare or even acknowledge me.  They simply ate their food.  While I was walking to the cash register to pay, I saw the woman who had looked at me as I entered the restaurant.  She was seated in an aisle seat in a booth.  She leaned out to see my outfit again.  We made eye contact and smiled politely at one another.  I paid my bill and left.

I changed into a black sweater pencil skirt and a red top and a faux leather jacket with my off-black pantyhose and flats.

Coffee Shop
I went to a coffee shop to purchase some gift cards.  When I walked in, I looked around to find where I should go.  The woman behind the counter warmly invited me to the cash register.  I made my purchase, thanked her, and left.  No one seemed to pay me any attention.  I was starting to feel like I was not an oddity!

Hardware Store
From there, I went to a hardware store in the nearby town.  This is a small, country town.  I was a little unnerved.  I figured I might have to hold my head up high around a bunch of hard-working, bearded, country boys.  They might not respect my fashion choices.

As I walked into the store, the cashier gave me a look that expressed a little surprise.  Regardless, she welcomed me professionally.  I browsed around the store for what I needed.  There were no burly men to intimidate me.  In fact, the store was mostly empty.  At one point, I passed a group of 50-60 year old employees (“good ole boys”) sitting and talking.  I found the general area that I needed to be in.  I hunted around for a few moments.  A female employee roughly 55 years old approached me offering help.  She helped me until I had found everything I needed.  She was very nice and social.  She even chatted with me for a little while after I was done shopping.  We walked together toward the cash register.  She left me in order to go work when we passed the employees who were sitting and talking.

At the cash register, there was a pretty woman in dressy clothes talking to the cashier.  She stopped talking so that I could pay.  She backed away, but paid a lot of attention to me.  The cashier was completely normal with me.  Later, I happened to look across the store to where the employees were sitting and talking.  The pretty woman was standing near there and had her phone out.  I wondered if she had taken my picture.  The group of employees were all slightly animated like they were amused.  I did not love it, but I was not really all that affected.

Walking Around Downtown
I drove into the downtown area.  Most of the shops were antique stores.  I saw a fancy dress shop.  I wanted to go in.  I parked my car.  I walked down the block to the store and found it locked with the door stating it was “open”.  I was in clear view of a man sitting on a bench across the street.  I walked back down the block.  I passed my car.  I visited an antiques consignment store farther down the block.  I looked around the store and then left.

I returned to walking down the street.  I reached the street corner.  A woman had just crossed the street and was standing there.  Another man was sitting on another bench.  This time the bench was on my side of the street.  I assumed that these men were unemployed.  I crossed the street.  I saw in a store window reflection that the man and woman were talking.  Of course, my worried mind assumed they were talking about me.

I went to another antique store.  The employee was very engaging and friendly.  I looked around and left.  I noticed more men on this side of the street just sitting on benches.  I decided it was time to get back in my car.  I prepared to cross the street opposite my car.  I noticed someone had opened the fuel opening on my car.  The car that was coming my way stopped.  I crossed.  I opened the door to my car.  The vehicle that had stopped for me was driving past me.  I looked and saw that the driver had her phone up and pointed at me.  She had just taken my picture.  Not cool!

Grocery Store
I left there and went to a grocery store to pick up a couple items.  Nothing interesting happened.

Office Supply Store
I started heading toward home.  I stopped at an office supply store to get some tape.  The cashier told me that I had to buy two to get the special price.  She was very social and friendly.  I told her that I was having a lot of trouble with static cling.  She recommended spraying hair spray near your outfit.  She said it wears off and you can do it again.  She said it works as well as those anti-static sprays in the store, but it is cheaper.  She rang me up for two packages of tape.  I went to the back and got a second package.  No customers seemed to acknowledge me or my outfit.  I think the black skirt did not draw much attention to itself as being unusual.

Clothing Store
I went to a nearby clothing store.  I shopped around a little.  I asked a staff member if they had khaki skirts.  She said no.  She talked to me briefly about what they had and what she likes in khaki skirts.  I shopped around some more.  I passed a 70 year old woman.  She was also wearing a skirt and pantyhose.  Later we passed again.  We spoke.  I told her that normally, I am the only person in a skirt and pantyhose.  She laughed in a friendly way.  I said, “I am going to think of you as my buddy.”  She replied, “OK, I’ll be your buddy.  I would be glad to be buddies.”  I started walking away, but she started talking to me again.  I came back and she talked to me for a couple minutes about how she has trouble finding skirts in her preferred style.

There was a man walking around.  He was walking between the ladies’ wear section and another section.  I considered changing my path to avoid him.  I decided, “No.  I will not let fear control me.”  I proceeded toward him.  His phone was distracting him and he did not look at me.

I had decided that I was done shopping in the store.  As I was walking toward the exit, the employee from earlier called to me, “Does it have to be khaki?”  I turned around.  She had found something for me.  She took me to a rack where there were khaki colored knit skirts.  Khaki fabric is woven and does not stretch.  These skirts were smooth feeling and would fit like some similar pretty skirts I have seen ladies wear.

Ladies’ Dressing Room
I asked, “Can I use the dressing room.”  The employee, assured me that yes I can, and motioned toward the nearby dressing room in the ladies’ section.  I have been to another store like this and have only tried to use the men’s dressing room.  I kept my eyes forward as I walked down to an open dressing stall so that no one would see my tall head looking in any way toward the door of an occupied stall.

I tried on the skirt.  It fit snugly.  I liked the fabric.  I did not care for the style.  it had buttons on it for accents and a slit in the front.  I exited the dressing area.  While I was looking at myself in the three-way mirror, the clerk approached me.  She gave me the advice, “It is not the right size.  I can see your (short pause to collect the right words) lines from your undergarments.”  She resisted saying “panty lines”.

The sales lady also gave me the candid advice, “Don’t wear that black skirt.  I don’t like the white part on it.  It looks ‘old lady’.”  I had some doubts about the skirt.  I am going to take her advice.

Just as I started walking back toward the dressing rooms to change out of the skirt, a woman who had seen me and who was shopping nearby said to her companion, “Let’s go to the dressing room and try it on.”  I did not really think about it as I walked on into the dressing rooms myself.  I went back to my stall (still looking straight ahead in the main area of the dressing rooms).  While I was changing skirts, a woman came into the dressing area and walked past my stall.  She was not the customer.  She was an employee.  She was the manager.  She passed my stall.  On her way back she spoke to me.  She, in a polite tone, stated that she might have to ask me to use the men’s dressing room next time because of the lady customers.  I told her OK and that I understood.

When I exited the dressing room, I thanked the employee who had helped me.  At the rack where the khaki skirt belonged, I found the customer who spoke of going to the dressing room.  She did not interact with me.  She seemed comfortable.  However, I wonder if she complained to management about me being in the dressing room.  I did not hear anyone besides myself come into the dressing rooms

As I walked toward the exit, I came upon the older lady in the skirt.  I said, “Good-bye buddy!”  She responded playfully.  As I passed the cashiers, three employees all said their good=byes and come again greetings.  One of the three ladies was the manager who had spoken to me in the dressing rooms.  She thanked me for coming and invited me to “come again anytime.”  That was well played.  She politely marked the boundary with me about the dressing room, yet she invited me back and added the word “anytime”.  She is good.

After that, I changed and went home.  By the time I got home, school was out.  I played catch in the yard with me three kids.  That evening, I told my wife about all of my experiences.  I admitted that going to the last clothing store was an example of me not wanting to stop.  It was like when the kids stall so effectively at bedtime.  My wife nodded her head while I said it.  I think she agrees.

Her final reaction was that she was glad I had a good time.




From → True Stories

  1. Anonymous permalink

    This sounds like a fantastic day. You continue to set a great example for all of us. Thanks for sharing your experience.

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