My parents are getting old; they’re in their 80’s, and my sister, who sees them every day, was telling me she didn’t think they had long to live. So I needed to go see them for myself. I live in Indiana and they are in Florida; a plane trip was going to be the best way to get down there and back quickly.

In my planning for the trip, I was thinking how I could find time to dress. I am comfortable in public as Diana and have never yet been called out as a guy in a dress. I decided to look at what would be needed to Fly Pretty. I googled and found several sites with information, including the TSA site  Maybe I could fly both ways as Diana. I would not have much private time down there.

In planning my outing, I was debating on wearing my Dresstech Big Girl Hip Pads. I knew I had to go through the body scanner and was not sure how TSA would react. I need the hip pads as without them I am straight on the sides. I contacted Dresstech through their website for advice. I got a return email the next day telling me:


Hi Diana,

Join Our Community-cdh

 We get this question fairly regularly.  Nobody has yet had an issue wearing their hip pads through TSA, but I honestly can’t make you any promises.  If you decide to do it, I’d really appreciate hearing how it went for you. The more feedback I get, the more confident I will be in assuring other people traveling pretty.  🙂



– Judi


So, I decided to go that route and continue the planning. I told my wife early in our marriage, of 17 years, about my dressing, but she does not want to know anything about it or to see it. I had to plan how to get dressed without her knowing. I decided to get a room in the next town on the way to the airport and get dressed there. I would be staying at a motel in Florida so coming back would not be an issue.

Planning done; I needed to pack and make sure my makeup was fully stocked and all was ready to go. The day was here, and I was nervous. I debated whether or not to wear those hip pads down to the last minute. I got to the motel, was dressed and ready to go in about 45 minutes. I had checked in the previous day and left my Drag bag staged and ready to go there.  I have practiced my makeup many times and have it down to about 30 minutes.

I drove to the airport and boarded the bus to the terminal with my two bags. One was my Drab bag and the other was for Diana. I checked in the Drab bag at the Southwest gate and kept my Diana bag, which had a change of Drab clothes and makeup remover, in case of any issues.  Diana’s bag was the heavier bag; us girls always seem to pack heavy, right. So far I am okay, as I’ve been in public as Diana many times, but the gauntlet was coming.

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I got to the TSA security checkpoint and stood tall and charged on. The checkpoint guard did look at the ID a few times and back at me, but did not challenge it at all. The next step was the scary one. What would security do on the seeing me go through the scanner. Taking off my shoes and placing them on the conveyor,  I was hoping to be bypassed in the metal scanner, but I wasn’t that lucky. TSA routed me to the full scanner. Hands up, and then the full scan complete, I came out of the booth expecting the worse. The female tech looked at the scan and said Ma’am I need to pat your shoulders is that okay. She did a quick pat on my shoulders; I think to verify I was wearing a bra, and that was it. I was past TSA.

Wow, I had made it. The rest was easy. I stayed at the gate, boarded the plane, and flew down to Florida. The Next gauntlet was coming up; the car Rental.

I went to the rental counter after getting my Drab bag and got the car. There were no challenges, no Mr., just a courteous clerk helping to get me on the road.

I told my parents that I would not see them till the next day, as “I was coming in late.”  I landed at 3:30, so some shopping was in order. I went to two different malls and tried on bunches, but did not see anything I couldn’t live without.

After shopping, I went to the motel, checked in still as Diana. Again, I had no issues, as if this happens every day. I went to my room, freshened up, and went out for a wonderful dinner.  At this point, I had already been dressed for 10 hours. I headed back to the hotel to call it a night. It had been a wonderful day.

I spent a few days with my parents, and found out they were not quite on their last leg just yet, and then it was time to come back home.

A trip back to return the car and back through TSA with no issues, and I was on the way home, though I once again did get that shoulder pat down. Once back in Indiana, a quick undressing in the car, and back to my lovely wife.

I am looking forward to my next adventure as Diana.


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Diana Stockton

I started dressing about 50 years ago. I still remember that first dress of my mothers I put on in the closet for fear my brother would find me. It was a yellow sweater dress. I cannot remember my motivations to do so. Even today I still do not understand them. However my dressing seems to be taking a bigger part of my life as I age.

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Trusted Member
4 years ago

What a wonderful article and an inspiration for all of us,
especially me….thanks so much for sharing

skippy1965 Cynthia
Trusted Member
4 years ago

Congrats Diana! I wrote about my own TSA adventures flying to Esprit -first in 2017- in stealth Cyn mode and in 2018 in full Cyn mode.
Tsa olks generally don’t care and the flight crews were all wonderful too. I don’t take drab clothes with me on those trips anymore. So it’s " all or nothing" lol. Same when I’m driving to conferences or visiting folks out of town. Next up in stop our n the 2019/20 Cynvasion tour- Hitting the Big Easy/New Orleans in January!

4 years ago
Reply to  Diana Stockton

Darling, There’s nothing to worry about, You walk into this “tubey thing", something swirls around it, & you’re done! They may run a hand up your leg (stopping WELL before your naughty bits) to make sure you’re not carrying anything you shouldn’t, but that’s it!
No weird looks, no snickering & pointing. It’s totally professional.
They could lose their job for unprofessional behavior. (They won’t risk it!)
Do your makeup, wear that dress, those heels, & have a good flight!

4 years ago

Diana you have just described my next trip except it is Jacksonville instead of Tampa. I have in the past dressed in a pair of skinny Jeans but no makeup or wig but kept that in my carry on. As soon as I got through security I would duck in a family restroom and add my wig, makeup and padding. Your story is giving me the courage to get dressed prior to going to the airport. I am only worried about the silicone pads and forms.

Thank you. K

Dawn Wyvern
Managing Ambassador
Active Member
3 years ago

Hi Diana I often fly pretty in the UK with no issues, but we have very good legislation to support for TG/CD over here ! however I have never had any problems with either the check in or security, its all about being comfortable in being yourself and presenting a positive image as you are not doing anything wrong – just be honest with your answers if asked any questions. Kimberly Huddle has a fabulous Bog that gives lots of adventures and great guidance on flying pretty in the USA which also entering and well worth a read! hugs… Read more »

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