Tag Archives: Cross-dressing

By Ann M.

Last month, my client, Ann, traveled en femme via commercial airline for the first time. Here she shares her experiences and emotions, providing us with inspiration and insight into the life of a trans-woman.

The satisfaction of accomplishing a substantial personal goal, any nervousness about spending the next eight hours fully cross-dressed in public with no way to back out, or thoughts about my long term future were pushed out of mind by the absolute frustration of trying to get to Dulles airport during rush hour when accidents were tying up traffic in both directions.

The poor woman inside my GPS went into conniptions as I tried alternate routes, my ears straining for any helpful nuggets from the traffic reporters on the radio, and making abrupt turns when it looked like traffic was gridlocked ahead.  I never heard the word “recalculating” so many times.  The sweet, nice woman I feel that I am deep inside gave way and I drove like a suburban tiger mom trying to get her kids to soccer practice.

The reason for all this was that I was finally taking, for me, the big step of flying on a commercial flight as a woman.  I needed to travel for personal reasons and decided now was the time.  My journey across the transgender spectrum has been a series of baby steps, each building on the other.  Each time, as I have experimented with pushing the boundaries just a little further, I have found that I feel right when I let my femininity shine and I have been very pleasantly surprised by the many positive reactions I have received.  Each time has validated who I am and shattered my own limits and fears.

This time, I would be working without a safety net.  Once I checked my bag with my boy clothes, there would be no turning back.  I would have to wait in line, go through security, and sit next to whomever took the seat next to me on the flight.  While I expected things to go smoothly, my mind was filled with the “what ifs…”  I also entertained fantasies such as a cute guy sitting next to me who found me adorable, but I didn’t expect that to happen either.

Shopping, Accessories, and Makeup

To allay my fears, I prepared for my trip almost obsessively, as is my wont when trying something new to expand my boundaries.  I had bought a new foundation garment from Classic Curves International that gave me curves proportional to my body.  I happened to find a perfect top, bought three pairs of jeans before I was satisfied (checking to see what might show when bent over to take my shoes off at security) and searched for the right accessories.  I tried everything on to make sure I had my look down and carefully packed so I was sure I didn’t forget anything.

The last thing I wanted was to draw attention because of a makeup problem.  While I consider myself reasonably proficient at doing my own makeup, I didn’t want to take any chances, so I scheduled a make over with Beth Taylor before my flight.  I knew that not only would I leave her studio looking fabulous, but that with her warm, accepting personality and positive energy, I’d be feeling good inside as well as looking good outside.

I was a little behind schedule when I got there, so Beth got right to work. Don’t know about anyone else, but I find it so soothing and relaxing to have someone applying my makeup as I sit and chat.  It makes me feel like a model getting ready for a photo shoot.

The great thing about Beth is that she “gets” trans-women of all varieties.  She creates an absolutely safe space where one feels free to let down her guard and revel in all things feminine.  While her business is makeup, she really is a confidante, coach, friend, and advocate, who, oh by the way, can create the look you have always dreamed of but never thought possible.

Ticket Counter, TSA, and Airborne!

So what about the flight?

After I left Beth’s, feeling fantastic, and fighting the traffic, I made it to the airport with enough time that I wasn’t too stressed about making my flight.  I am quite tall, so I stand out in a crowd, and noticed I did get a few looks from passerbys, but for the most part everyone was wrapped up in their own business or didn’t notice me.

There turned out to be no line for the ticket counter, and I checked my bag.  I showed my ID, which has my male name and photo.  The woman at the counter said I might have a problem at security, but I told her I had looked up the TSA policy for transgendered passengers and had a letter from my therapist explaining why I was traveling as a woman.

The TSA screeners didn’t blink an eye.  I showed my boarding pass and ID at two checkpoints and was called “ma’am” in spite of what my ID said.  I did get a pat down after the scanner, and they didn’t even ask me if I wanted a male or female screener, they just sent me to a woman.

As I waited for my flight, I was struck by my lack of feelings about what I was doing.  Everything had been so routine, that it just seemed like any other commercial flight.  I sat in the waiting area feeling very ordinary and very comfortable. Since the flight was only about a quarter full, I had a row to myself and settled in to relax for the flight.  I had a glass (okay, a plastic cup) of wine, and was a bit surprised that the flight attendant never asked me to pay for the drink.

After we landed, I wanted to document my accomplishment, even though by that point I was wondering why I had thought it was such a big deal.  I asked the flight attendant to take my picture to which she enthusiastically agreed. She posed me in front of the Southwest Airlines logo on a bulkhead and took several photos.  We started chatting, and I told her that it was my first time flying en femme, to which she replied, “Now I’m really glad I didn’t charge you for the drink!”  All the other passengers had long since left, and the pilots looked like they were ready to leave, so the flight attendant wished me good luck on my journey to womanhood.

Hotel Room Reflections

I took the shuttle to my hotel and checked in, again showing my male ID, and again receiving nothing but respectful and empathetic courtesy from the clerk at the desk.  We chatted a bit, she told me about breakfast, and I found my room.  While it pained me to have to remove the beautiful makeup Beth had applied, it felt great to take off my wig, earrings, and all the other accouterments I use to tell the world that there is a girl under here.

As I lay in the bed, reflecting on my experience, I was struck by how underwhelming it had all been.  I was simply one woman among thousands of drivers that afternoon trying to get somewhere in the area with the second worst commute in the nation.  I was just another airline passenger going through the routine of boarding a commercial flight.  I was the glass of red wine in row 32, the lady going to the Quality Inn, the guest in room 231.  When my gender did come up as a result of my ID not matching my presentation it was treated as a minor discrepancy and quickly resolved.

I had spent weeks thinking about what I was going to do, planning, shopping and building my resolve to carry through with traveling as a woman, but afterwards, it seemed like a very ordinary, rather dull, exercise in getting from one city to another. And that was the most validating, wonderful experience I could have dreamt of.