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Flying In A Skirt On A Plane

May 28, 2012


There is a term in the crossdressing community called “Flying pretty”  This is what we call going traveling by airplane while crossdressed.  I have done it, and in some ways it was almost a non-event!

I had to go on a trip.  When I traveled away from home, I was dressed in my men’s clothes.  When I first arrived at my hotel, I talked with the hotel staff.  The girl at the front desk was very friendly and social with me.   Every evening after my business was complete, I dressed up in a blouse, skirt, and heels and went out.  One night, I visited the front desk while dressed this way, the same girl was working.  She seemed uncomfortable, but she was helpful.

One morning, I wore a skirt down to breakfast.  I was in the breakfast room with 10-15 people eating breakfast and watching television.  That was scary.  Some people noticed me and became quiet.  One or two would point me out to their friends or family who were sitting with them.  If I spoke to someone to say, “Hello,” they would politely say, “Hello, ” back to me.  After someone would notice me, they would continue eating and lose interest in me.  It was very frightening and stressful but exhilarating and freeing, and I did it!

On the last day of my trip, I dressed up in my skirt again (with flats) and drove my rental car to the gas station and filled it up.  Then I drove to the rental facility.  In the rental facility garage, there were a couple customers and two employees.  The employee who processed my car seemed a little rough.  I wondered if he would be rude to me.  However, I am not sure if he took the time to look at me.  He was an efficient worker.  He came and scanned the car, checked the mileage, and gave me my receipt in one minute or less.  I walked from there pulling my suitcase behind me.  I walked through the service desk and lobby area.  There were a few customers.  A couple of them paid some attention to me.  But no one was impolite.

Fortunately, the airport shuttle bus was already there.  I climbed on board and put my suitcase on the rack.  I rode the bus to the airport terminal.  The other people on the bus gave me no reaction.  At the airport, I went and stood in line for my airline to check my luggage.  I was growing concerned.  I was about to hand all of my men’s clothes to a woman at a desk and then I was going to walk away with NO safety net!  I asked the woman, “Will you please look at my outfit and tell me if I will have any problem in security.”  She looked at me and in a moment of awkwardness, she said, “I don’t know.”  I followed up with, “All of my guy-clothes are in this bag.”  She understood my concern and she said, “I don’t think you will have any trouble, but I will hold your bag out until you get through.”  I thanked her for being so nice to me and I moved on.

I stood in line for security for a long time.  The corral went back and forth.  Everyone in line within 20 people of me had a few opportunities to see me pass them as we zig-zagged our way toward the front of the line.  No one was impolite.  Most people paid me little attention after the first glance.  I was rather comfortable with being around people.

I went through security.  The person at the front who looked at my ID was just as professional as every other one I have ever encountered in my travels.  I took off my shoes and stood in line for the full-body scanner.  I was in between two women while I was wearing a blouse, skirt, taupe pantyhose, and in my stocking feet.  Every member of security I came to acted like I was their 10,000th crossdresser of the day.  I was scanned and then progressed without incident.  I received my belongings and slipped on my shoes.

Benefit #1 of crossdressing at the airport: Slip on shoes are VERY easy to put on after security.  I considered never wearing men’s shoes to the airport again!

Walking to my gate was stressful!  Hundreds of people were walking past me in the other direction and almost all of them were literally looking right at me.  I was concerned that I might come upon someone who knew me.  Eventually, I stopped in at a bathroom.  (I went into the men’s room.)  It was empty.  I did my business and went to the sink to wash my hands.  While I was standing at the sink tucking in my blouse, three men in their 30’s came in.  They used the urinals that were positioned on the wall behind where I was standing.  One guy, with a shocked expression on his face, was looking over his shoulder at the back of me.  He did not notice that I could see him in the mirror.  I left there and went on toward my gate.

Benefit #2 of crossdressing at the airport: The annoying credit card sales people are less likely bother men in skirts.  They would look at me, but not one of them ever dared to speak to me.

When I arrived at my gate, I found that there were a lot of people already there.  I sat in a seat between a woman and a man.  The man was watching a movie.  Another passenger was talking loudly on her cell phone.  She was saying a lot of crazy stuff.  Several passengers around her were reacting to her with shock and hilarity.  I talked to the woman beside me about it.  She laughed and told me how long it had been going on.  It was very funny!  I sat between those two people for at least 30 minutes.  The woman beside me talked to me occasionally as if I was anybody else.  Maybe she did not notice.  Maybe she did not care.

When I was called to board the plane, I walked down the jet-way and was greeted by a couple stewardesses as I entered the plane.  Like every other woman I encounter while I am dressed this way, these women looked immediately down at my shoes and then back to my face.  They all politely welcomed me, but one stewardess seemed happier to see me than the rest.  I did not think much of it, but she smiled like I was her long-lost best friend.

On the airplane, there were three seats on either side of the aisle.  A man about my age was already sitting in the aisle seat.  I excused my way past him to my window seat.  He never spoke to me.  A 60 year old woman later sat between us.  She sat down and started reading a book.

Later, during the flight, the stewardess who smiled so nicely at me visited our row.  She spoke to us and took our drink order.  She looked at me and gave me another one of those unusually nice smiles.  The older woman said to me, “She likes you.”  I asked, “Do you think she likes me, or is it because of how I am dressed?”  The older woman looked at my skirt and then closed her book and started putting it away and said, “Oh, I’m going to talk to you.”

She started asking me lots of questions from, “Does your wife know?” to “Where do you put your private parts?”  I directed her away from the more personal questions.  The woman was fascinated.  She was so curious to understand more.  I tried to answer her questions without being loud enough to let neighboring people hear me.   We talked for the next hour.  We left the plane together and walked to the luggage return area together.  It was much more comforting to walk from through the concourse past so many people with a person at my side.  We collected our luggage, her husband came to get her, and we said our good-byes.

I went outside to the bus stop.  I waited 10-15 minutes for the bus that would take me to the parking lot.  A man was there also waiting.   Although it was getting dark, I think saw what I was wearing.  I normally avoid men when I am crossdressed, but I spoke to him.  We talked for a few minutes about work and then the bus came.  I rode the bus to my parking area.  On the bus, I sat facing a couple with a two year old.  The father was on the phone.  The toddler was crying.  The mother looked tired and embarrassed because of the crying child.  I wrinkled my nose and smiled at the kid.  I waved at him.  It worked.  Having a stranger wave at him made him draw close to his mom and stop crying.  She and I spoke a sentence or two.

I stopped and did some shopping on my drive home from the airport.  I will save that story for another post.

At the end of the day when I changed clothes, I was impressed to find that I was not drenched with sweat.  That is a big change for me.  I used to sweat heavily from the stress I was feeling when I was wearing nude hose with shorts.  Here, I was home after many hours of wearing a skirt and obvious hose in front of hundreds of people.  I am learning to relax!

In all that week of travel and crossdressing, I never wore make up or a wig.  I was a man in a skirt and no one really cared.  They looked at my face, then looked at my clothes, then they looked at my face and then they looked away.  I think most of the women immediately looked at my shoes.  I have since asked around and my theory was confirmed.  Women’s first glances at other women is at their shoes (and hand bags).  I believe that the men were looking less specifically at my feet and more at my skirt, legs, shoes in general.

Going out with my man head and a skirt is so freeing!  It seems so backward to say this.  I am obviously a dude in a skirt.  I guess once you get the secret out into the open that you are a crossdresser, then there is nothing left to worry about.  When I am wearing nude pantyhose and shorts, I am very concerned that people are going to notice.  I feel like I need to keep my secret.  But in a skirt, there is no hiding what I am doing.  I think about Randy Pausch saying, “If there is an elephant in the room, introduce it.”  When I am out dressed like this, everyone knows what is going on.  No one does anything about it.  They look at me and then they go about their business.  If I speak to them, they seem authentic and natural toward me.  However, I do think people are not as prone to speak to me first.


From → True Stories

  1. Lonnie permalink

    I travel regularly for work as in 125,000 miles or more a year on commecial flights. I am almost always dressed to the nines, head to toe. Never have I had any problems anywhere except LAX where they are constantly undecided as to whether I get a female or a male assist for TSA patdowns so end up getting both.

  2. jackie permalink

    I enjoyed your story. I am very happy it worked for you. I am cross dressed every day and I would love to go out en femme but it would a big change. I have facial hair, beard and mustache. I wear compression stockings every day with either a kilt or skirt. I have a number of tops that look not to bad on a male body. Then I also have jewellery and other accessories. I have a small shoulder pursue I use as a sporin when i wear my kilt. I’m just getting into shoes. Happy travels.


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