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A Two Day Trip

October 8, 2015


I ended up having a need to take a short, overnight trip across country.  When things like this come up, thoughts like, “Ooh, I could take some pretty clothes and dress up!”  Sometimes, I get a guilty feeling like I am exploiting the situation.  It clouds my motivations.  But the thoughts are always there.  So, I decided to bring some pretty clothes along.

I am filling my wife in on my history of crossdressing.  I do not want to keep secrets from her and she is not completely comfortable about it, but she wants me to be open.  So, she has recently heard about my first time flying in a skirt.  She asked me, “Are you planning on dressing?”  I told her I was.

Since I might still want to wear shorts, my legs are not yet shaved.  Therefore, I took only maxi skirts to wear.  I am so glad I have discovered them!

Busy Men’s Room
As I flew out of my home city, I was dressed in drab.  In my carry-on bag, I had my pretty outfit.  When I got to the airport where my connecting flight was, I changed into my pretty clothes in the men’s room.  I put on a black and white, striped maxi skirt, a bright orange lightweight blouse, and a black cardigan.  I never wear a bra or makeup or a wig.  The men’s room was rather busy, but I was mostly comfortable.  I walked out of the stall and washed my hands in the sink with men all around me.  No one behaved any differently toward me than if I were dressed masculine.  Maybe the crowd helped.


Deserted Concourse
I had a long layover.  I went to the gate for my flight.  The concourse was mostly deserted.  The only people there were like me, people with a long layover.  I walked the whole concourse looking for something to do with my time and also for a place to eat lunch.  I felt like a lot of people looked at me.  I was particularly self conscious.  That probably made me more aware of glances.  However, I was not very stressed.  I know that because I did not sweat heavily.

“That’s a pretty dress”
While I was walking the concourse, I went into a duty-free store.  There were four women working the small store.  I think they were in the middle of a shift change.  Each of them greeted me at some point.  They all asked me if they could help me.  They all took glances down but immediately returned to eye contact.  One woman, however, looked me up and down while asking me if she could help me.  Then she stated “That’s a pretty dress.”  She repeated it again later.  I needed nothing they had.  After a brief visit, I left the store.

I continued walking in the mostly-empty concourse.  I became less nervous.  As I walked, I saw a woman walking in my direction.  As she approached, I saw that she had long straight hair and little, or perhaps no makeup.  I thought that she might be a very conservative person and would disapprove of my outfit.  I cannot remember if I smiled and greeted her or not.  But suddenly, she smiled and said something kind about my skirt.  It might have been, “I like your skirt” or “Nice skirt.”  I could not hear her well.  This was a nice way to start my dressing outing.

“Crowds and many eyes”
I walked to the other end of the concourse.  It was busy.  Lots of people were walking and many people were sitting.  Some people paid no attention to me.  Other groups of people who were sitting down would suddenly all turn and look my way.  I saw one large framed woman sitting in a chair along the wall.  I wondered if she was a transperson.  I could not tell.  I did not stare.  At one point, a group of three airline employees were talking.  One saw me and made a sound.  The other two quickly yanked their heads around to see whatever it was.  They all three were looking at me.  I smiled and greeted them, since I had little else to do.

I eventually made my way back to my gate and sat down.  There were only about a dozen people scattered around the many seats.  Only a few appeared to notice me.  Those who noticed me seemed to go on about their business soon after noticing me.  I sat and read a book.  About twenty minutes later, I got bored and decided it was late enough to go eat lunch.  I walked down the mostly deserted concourse to a restaurant I had chosen earlier.

Restaurant and a conversation
At the restaurant, I ordered my food and found a seat.  My seat was facing the concourse by the restaurant’s entrance/exit.  My table was against a short iron fence.  Apparently, one or more planes arrived in the deserted concourse.  Crowds of people started flowing past the restaurant.  Some were going away from the planes, others going to the gates to eventually board the planes.  The people passing occasionally looked at me.  They apparently saw my legs through the iron fence or they saw the side of me.  I was OK with it.  I did not stress.  I started chatting with the woman across the aisle.  Another woman came and sat in the seat directly to my right to my right.  After finishing my meal, I turned and faced the woman I was chatting with.  She never obviously looked down at my clothes, but I do not know how she could have not noticed them.  She treated me normally.

Eventually, I walked back to my gate.  I had grown very comfortable.  I had stopped looking in everyones faces.  If they looked at me or not, I did not bother to find out.

Rude man with a camera
When I returned to my gate, there were a lot more people there.  I returned to my previous seat.  There was a man 10 feet across from me facing me.  He was using his phone.  He lifted his phone up as though to photograph me.  I moved 5 seats to my right.  I look at him and he had his camera pointed at me.  If he took my picture, I may have had a very angry face .  I got up and walked to a seat where he could not photograph me.

Friendly conversations
I started reading a language learning book.  More people filled in the seats around me.  I saw some look at me, but nothing more was done.  Younger people took more looks, but I never saw them pull out their phones.  At one point, a young man across the aisle to my left started talking to me about my book.  He spoke that language too.  He was better than me.  We chatted for 20 minutes.  He got up to leave when his flight started boarding.  I spoke to the big, muscular man across from me.  We had been on the same first flight.  He talked comfortably with me for five minutes until we got up to go board our plane.

Trans airline employees
On the plane, I sat next to a professional woman.  She had to get up for me to get to my seat.  While still at the gate, I saw a woman come onto the plane to give the attendant something.  She was a tall, large framed woman.  She had on a wig.  Around her neck, she had a stretchy band right where an Adam’s apple would be.  I think she was a transgender woman.  She was dressed in her airline uniform dress and reasonable heels.  She turned and left the plane a moment later.  The woman I was seated by and I talked about various topics for a few minutes until she started reading her book and I started listening to a book on my player.

On my way to the baggage claim area, I noticed that someone was walking behind me.  After the moving walkway, the person came along side of me.  We looked at each other.  It was an airline employee in a shirt and pants uniform, long black hair, feminine flats, black hose, red finger nails, breasts, but apparently a man.  No make up.  I spoke and he responded with masculine voice.  No further conversation.  I do not know if this person identifies as a a transgender person or as a man like me who dresses feminine and stays masculine.  Later, at the baggage claim area, I saw the person waiting with a woman and a child.

Friendly police officer
When I got to the conveyor for my flight’s baggage, I saw the big guy from earlier.  We started talking.  He told me he was a police officer.  We talked for a long time while standing there waiting for our luggage.  He seemed comfortable talking to me and did not seem to mind that it was just the two of us standing there for a long time.

Someone called my name!
While I was standing there talking to the police officer, I heard someone say, “Joey.  Joey, turn around.”  My hairs stood up!  I contemplated what to do…  Then she said again, “Joey.  Turn around.”  I decided that if I was caught, pretending that it did not happen would not change anything.  I turned around.  About 10 feet (3 meters) behind me there was a woman looking across the room at another man.  She yelled out, “JOEY!” and Joey turned around.  I was happy it was not someone I knew.  I was impressed with how non-frightened I was.  I did not panic.  I did not need to run or change back into drab.  I just went on about my business.

Car rental
Next, I walked to the rental car shuttle, and rode the shuttle bus to the rental car facility.  I did my business at the counter.  As I walked outside to find my car, an older man who worked there greeted me politely.  I looked back and he was stopped, looking back at me, with an odd look on his face.  He said, “May I ask you a question?  Please don’t get angry.  But, why are you, on this pretty day dressed like a young lady?”  I said didn’t know other than that I just like it.  He said, “All right,” and offered me a fist bump and wished me well on my journey.  I went to my car.  An older couple were getting into the next car.  They took the time to watch me walk around my car and look for damage.  It was awkward walking around my car while they sat and watched me.  Then, she had her husband get out of their car and walk around it inspecting it for damage.  She did not make him put on a skirt, though.

Big department store
I drove toward my destination.  I stopped at big store to get a couple things I wanted.  There were long lines at registers.  I got into one line for a while and then remembered something else I wanted.  As I walked along, I heard laughing.  There was a teenage girl with her mother.  The girl was laughing at me uncontrollably.  That was the worst thing that happened on my trip.  I found what else I needed and then got back into line.  I used the self checkout and left.

Fast food restaurant
I stopped in a fast food restaurant for an early supper.  While I was at the counter, a man in the back called to me, “That shirt is the most orange shirt I have seen all day.  You must be ready for Halloween.”  I replied, “Happy Halloween!”  There were two young adult women standing at the receiving area of the counter.  They looked over at me, smiled, and glanced over their shoulders at me looking slowly down my side.  They had seen me walk up, but at this, they took it all in.  I have seen women look at each other this way.  It was nice to join the club.

Will you take my picture?
I drove on, and stopped at a couple other stores.  At one store, I asked an employee to take my picture.  She politely helped me and even took another set when the first set was blurry.  She suggested a better backdrop.  She was completely comfortable.  I think I was too.  Then, I changed and went the rest of my way to my destination dressed in men’s clothes.

Day two of my trip
On the next day, when it was time for me to return to the airport, I put on an orange maxi skirt, my black flats, and a black and gray top with 3/4 sleeves.  I did not have time to make any stops on my way to the airport.  I drove my car to the rental car facility.  The girl who received my car was bright and friendly.  She was professional and efficient.  I went to the shuttle bus and got on.  I was the only person on the shuttle bus.  He dropped me off at the airport and I checked in at my airline.  Some people looked as I went along, but by this point, I was not that concerned with it.

Searched in security
When I got into the security line, there were a few other people.  I noticed no one pay me much attention.  I took off my shoes and waited to be scanned.  After being scanned, the attendant reacted to the screen.  I looked.  There was a warning rectangle on the image of my silhouette.  It was near my crotch on my leg.  I thought, what did that thing see?  The woman asked me if I would prefer to be inspected by a man or a woman.  I said a man.  The man had me stand a certain way and he felt my leg.  Then he felt the other.  Then he wished me a good trip.  No one bothered to react to how I was dressed beyond that.

Second flight
I did not have time to have any supper on my way to the gate for my flight.  I only had time to stop at a shop and to buy a cup of fruit.  I ate it as I hurried to my gate.  When I arrived at my gate, the only remaining people to board the plane were 5-10 people, and they were in line.  Another man at the gate was dressed unusually.  He was wearing a bowler hat and a wide-striped suit.  He had a cane, and he wore a big, fancy mustache.  I tried to figure out if he was in a costume or if he just dressed like this all of the time.  Another man approached and saw the mustache man and I standing there.  He asked the other guy, “Are you the in-flight entertainment?”  I think he did not appreciate the attention.  He said, “No, he is.”  I just smiled.  The man who asked the question may have realized that no one was in costume, because he turned and went back to his wife.  In retrospect, I wish I had spoken to the man in the mustache.  I did not figure out quickly enough that he was just dressed that way.  I would expect that he gets similarly strange looks as I get when I am out dressed.  However, I think people might approach and comment on his outfit before they would comment on mine.

Talkative doctor
On my flight, I sat by a doctor.  We talked the whole time.  He was completely comfortable being friendly with a man in a skirt.  At the next airport, I planned on changing back into menswear.  I realized that I forgot to get a picture of me in my pretty outfit.  I asked a worker if she would take my picture and she did.  Then I changed and went to my gate to catch my flight home.


I am sorry this picture is so blurry.  There was a bit of a language barrier between the nice lady who took this picture and myself.  I decided it would have to be sufficient.


From → True Stories

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