Cynthia’s Esprit 2017 Travelogue – Traveling Travails


During the middle of May, I attended the Esprit 2017, a crossdresser / transgendered conference in Port Angeles, Washington, which is about two hours outside Seattle.  Having attended the Southern Comfort Conference last September in Fort Lauderdale, Florida, I was not a novice to attending such an event.  This was my first time at Esprit and my first visit to the Pacific Northwest region of the United States.  This piece will be sort a travelogue describing my experiences and adventures.  I want to provide a picture of what occurred in the hope of encouraging others to take the opportunity step out of their comfort zone, (or break out of the prison walls of their home).  Perhaps, my adventures will inspire other to let their true selves experience a taste of the real world.  In a separate piece, I will explore what I drew from the experience and the deeper thoughts about how it affected my life and future path.

Unlike the Southern Comfort Conference, which was a “mere” 925 miles or a thirteen hour drive, the Esprit Conference was a tad too far for a practical drive.  At just under three thousand miles, I would have been looking at 43 hours of driving, which is too much, even for one who regularly drives hundreds of miles to watch college football!  Even the train would have taken three days, so the only truly viable option was to fly, about five plus hours travel time.  Of course, that meant I would have to face the fierce dragon known to strike fear into the hearts of all who travel the “friendly skies” — the dreaded three letter beast known as TSA !!!  (Insert frightening, ominous music here!)

Before that encounter, I first had to winnow down a selection from my wardrobe that could fit into two checked bags and one carry-on bag, three bags of less than fifty pounds each?  Are they crazy?  Can any woman fit a week’s worth of necessities into such a pittance of travel bags?  Heavens to Betsy, for Southern Comfort, I had packed my car with eight suitcases, (two of which had only shoes), and five wardrobe bags!  Now I had to decide what items would make the cut, and which would be left out of the trip.  Hours, days and weeks of agonizing was completed at four in the morning, the day of my departing flight.

Crossdresser Heaven - Find Your Tribe

Once at the airport, it was time to face the dragon.  The two bags were checked, and I approached the TSA security check with my carry-on and laptop bag.  I had considered making the flight in full Cyn regalia, but I was a tad too cowardly to do so.  Instead I wore ladies’ shorts, socks, and shoes with a t-shirt and my baseball cap.  Nearing the x-ray scanners, I dutifully emptied my pockets completely, (“Even paper receipts can set off the machine!” one TSA agent reminded me and my fellow travelers.), before removing my hat, shoes, coat, belt, panties, and shorts.  Okay, I am kidding, but only about the last two items!  I even checked my navel for any lint that might have been there.  As I emtering the full body scanner, an agent came up and asked, “Is this carry-on bag yours?”  I replied yes, and he said to come meet him at a separate table after being scanned.  As I approached the indicated table, the agent opened my carry-on bag.  While I was wearing a male (or neutral)t-shirt, that was the only non-female item that I had in my possession.  Beginning his search of the bag, he removed my purse, rifled through it, took out my rolled skirts, dresses, and tops, and placed them in a bin.  As many of you may know, I am a huge fan of peanut butter.  Apparently, I accidentally had placed a butter knife in my carry-on which had triggered the alert.  I quickly apologized, and said, “Please, just throw it away!  My travails, however, were not over.  The next words from agent’s mouth were “What’s in this box?”, as he held up the box containing my breast forms.  There was nothing to do but answer honestly, so in a semi-quiet voice I said “breast forms”!  He said “I need to open the box” to which I said, “Okay.”  (Really, what else could I have said?)  He ran his chemical residue skimmer around the forms and the box, and said, “Okay, you may go on now.”  The breath that I had held in for the last three minutes was finally released.  I quickly repacked the items into the bag, and left to enplane.  Thus was my first TSA experience with Cyn’s things!

After the excitement of getting through security, it was a relief to experience an uneventful flight.  Arriving in Seattle, Saturday evening, I was met by Crossdresser Heaven’s own, the lovely Pacific Princess April, who had invited me out to Esprit, and would be my roomie at the conference.  She helped me gather my checked baggage, and we walked from the SeaTac Airport  to the hotel across the street where we stayed that night.  We rested for an hour or so, before Cyn and April went out for drinks that night.  Heading back to the hotel around one in the morning, we fell asleep with visions of what we would experience in the upcoming week.

Be sure to read Cynthia’s continuing adventures at Esprit 2017.

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The Original Cyn, or OC for short. Cynthia is from Richmond Virginia, she crossdresses every day (lucky gal!) and has a knack for tracking down niggling technical issues so we can fix them. She is also on a journey of self-examination to figure out where her feminine journey will lead her, and is always willing to talk with others about their feelings and questions or her own.

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  1. Kirsti Smith 3 days ago

    Just flew today. I can’t pass so I just wear women’s Women’s clothes that don’t stand out. Today I wore booties, panties, socks, jeans, flannel shirt, and wireless, front close, racer back bra. All women’s ;). Left my breast enhancers and pair of heels in my carry on that got searched. Noting was said. When I went through the scanner it detected my bra. They searched me and asked if was wearing a brace. I told them it was a bra and they let me go. No problem.

    I plan on doing the same on my return flight with a little more daring blouse, my heels, and skinny jeans 😉

  2. Abbygale Norton 2 months ago

    How stressful, I read your story holding my breath!
    Happy you defeated the dragon!
    XOXO Abby

  3. Terri Anne 10 months ago

    Hi Cynthia, though I read this a long numbers of days ago, I had neglected to comment. Really enjoyed this article. Very helpful information for someone who has never had to experiance TSA or any conferences.
    Thanks much!
    -Terri Anne

  4. Darcy Bainsley 1 year ago

    Haha Cyn I don’t know how you can possibly wear so many things in 7 days. Of course TSA is always fun. I went through security in guy mode the outer shell they did the full body X-Ray and noticed my bra – of course I had to get the TSA side boob feel up – it was funny.

  5. Cynthia 1 year ago

    Several years ago, a TG friend of mine flew to SCC in femme. She was wearing a corset that kept setting off the metal detector. Beyond that, she had not problems.

  6. Monica Meadows 1 year ago

    Just flew to Chicago and back all dolled up. TSA wasn’t so bad. Just need to show them the ID of your gender and not fib if they ask. Got grouped by a female agent on my way to Chicago but then she apologizedoesn’t once she felt by my crotch and realized I still had something extra there. And that was the funny thing. They never bothered to look at the ID as I went threw the scanning machine. When I made it out of the machine they asked me what I had in my crotch and I said what God gave me. At first this probably wasn’the the best thing to say, but as she reached her hand near, I coughed and she quickly realized her mistake. I will never hide flying pretty is the way to go. On the way back from Chicago no problems.

  7. Rebecca 1 year ago

    That was a great story. Last year I did the same as you pack everything and headed to the airport I packed my forms in the carry on bag was going to put them on once I landed, I had a 3 hour drive and did not want to miss any Rebecca time. Well TSA opened up my carry on and my heart fell to the bottom of my boots and was beating so fast i am sure she could hear it. Ask me what is this I took a deep breath and told her she wiped them and told me to have a great day. What a wonderful week I had.

  8. Glory 1 year ago

    Inspirational Cyn. Your experience is what educates not only us but the TSA person you dealt with and without doubt the many conversations he had with colleges that day. This aids the acceptance of our community to be who we are where ever we chose to be.

  9. SteffieC 1 year ago

    Go Cynthia!!

  10. Janine 1 year ago

    Thank you for telling me about what to expect when dealing with the TSA.
    I’ve wondered what would happen if I decide to fly while taking a suitcase with my en femme attire with me
    I suppose if it is a check in at the airline ticket counter that there wouldn’t be a problem.
    Not knowing what to expect I chose to travel to Key West recently by automobile instead of flying.
    Although it was a 7 hour drive I drove there completely in my en femme attire and actually enjoyed the experience
    I only stopped for gas and one time to eat and to use the ladies room.
    I was referred to as miss or ma’am whenever anyone spoke to me
    In fact one girl who was waiting on me asking me where I found the sandals I was wearing
    I’m planning on going to Las Vegas soon and it’s to far away to drive there so I’m going to fly.
    I haven’t decided if I’m going to fly en femme or just bring my feminine attire with me
    I haven’t had any issues while being dressed en.femme but the TSA at the airport might be something that I don’t want to deal with
    After reading about your experience with the TSA I’m inclined to be on the safe side and travel in my male mode until I get to the hotel where I’m going to be staying
    Thanks for the heads up about what to expect at the TSA in the airport.

  11. Kara Kelly 1 year ago

    Great article. I can not wait for more.

  12. Sophie Frenchie 1 year ago

    Well Cyn, that was an experience for you sweetheart. It read as if you had dealt with things extremely well, so congratulations. I will be able to apply for my passport in a couple of days and will be able to travel as Sophie and the thought is very exciting. I look forward the next part of your travelogue.

  13. Holly G 1 year ago

    OMG Cyn! I don’t know what I would have done!! You handled it like a pro Can’t wait to hear more about the conference experience! I’ve wondered if they would even allow breast forms in a carry on bag but I guess now I know

  14. Isabelle 1 year ago

    Cynthia – fun story and heart-stopping. I travel frequently en femme in Europe (France) but on the train and there we don’t have such issues as those with the dreaded TSA, but there is still as always the risk of running into an acquaintance who doesn’t know !
    Keep on having fun 🙂

  15. Lady Veronica Graunwolf 1 year ago

    Cynthia……..great story and what an adventure!! These are the things life is made for.
    Thank heaven customs check went ok. I know know what to expect if I ever fly again.
    Looking forward to your continuing tales of danger and high adventure!

    Have a great time girl……..

    Lady V

  16. Leonara 1 year ago

    Great story Cynthia. Thanks for sharing your experience especially that I shouldn’t leave the peanut butter knife at home!!! Looking forward to part 2.
    Be well, Leonara

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