In late May, I traveled to New Orleans to celebrate my cousin’s 80th birthday. She had organized a big fete for herself, and I, and a number of other relatives, including my brother and sister and other family members were invited, and I decided to attend.
Of course, these days, when I travel I usually have more than one objective (when I’m traveling by myself, that is). There is the objective which is in plain view–like a trip to New York to visit my son and help him move, followed by a trip to Pittsburgh to watch the baseball Cardinals play.
But there’s also another hidden agenda, which is giving me opportunities to dress up in a new and different place.
And going to New Orleans was no different.

Originally, I thought about driving down to New Orleans. It’s about a 12-hour drive from where I live. I could stop along the way, and perhaps visit a casino or two, or stop along the Gulf Coast to have some bikini time. However, I had other commitments that precluded me from driving, so I ended up flying (but not flying pretty).
One complication of this trip is that my cousin and relatives and I were all staying at the same hotel. That added to the degree of difficulty in going out and in unnoticed while dressed, because I was on the ninth floor, so I needed to take the elevators. Plus, my brother’s room was three doors away, and between my room and the bank of elevators.
Fortunately, there was a door to the outside near the elevators on the ground floor, so I didn’t have to walk through the main lobby. And upon returning to the hotel, I could see through the glass doors if anyone was waiting at the elevators. If the coast was clear, I quickly entered the hotel, got on the elevator, and got to my room.
So, obstacles–but not insurmountable obstacles. When there’s a will….
For this trip, I did a pretty good job of limiting myself to potential outfits to take. I didn’t really want to take two bags of luggage. The other factor was heat and humidity, typical New Orleans weather, so I needed to make sure that whatever I chose was heat appropriate.
I arrived fairly early in the day on Tuesday, and left fairly late in the day on Friday, based on the week’s events and convenient (read: non-stop) flights.
My cousin had also arranged for early check-in at the hotel for all her guests. Getting in early meant I could change reasonably quickly and begin exploring the neighborhood around the hotel. The hotel was located in Central New Orleans, relatively close to the French Quarter, and also about a block away from one of my frequent destinations, a casino.
My chosen outfit was more casual chic than usual for me; a combination of a Free People top I bought at Nordy’s and new jean shorts from American Eagle, my store of choice recently–plus my omnipresent Red Keds, a favorite of Miss Dee-ism, and suitable for walking around the streets of New Orleans. This type of outfit is about as blendy as I get.
I started wandering towards Bourbon Street, first passing through the Casino. I then found a place along one the major avenues for a late lunch.
I then strolled through parts of the French Quarter, always looking for photo opportunities. I stopped in a few stories during my return, mostly to soak up the air conditioning.
On my return, I walked through the casino again–and noticed someone that looked suspiciously like one of my male cousins, walking towards me.
I thought to myself “that looks like Chris”. Then, I quickly noticed following about a step behind him was his girlfriend. Suspicion confirmed. I looked away and was satisfied they did not spot me–and probably wouldn’t have recognized me anyway.
I returned to the hotel and managed to get on the elevators and into my room without an issue. I got cleaned up and changed into boy mode for that evening’s activities.


The next morning, the day of the birthday celebration, I decided to go ziplining with two of the adult daughters of one of my cousins. They tend to go ziplining whenever they travel. I had never joined them before–I had never been zip lining–but I decided that this would be a good opportunity.
They found a place about 45 minutes away that ziplined over some swamp land They were happy to have me join them–especially after I offered to drive. I’m including the ziplining pictures just to demonstrate that I do things other than just going around dressed!
Stepping off the platform–and hoping the harness would hold was a bit stress inducing (I was happy to be wearing black shorts, if you know what I mean). But then again, so is going out (as a guy) in a dress and heels–but I’m a lot more accustomed to the latter these days.
The other spectator sunning itself on a log with fortunately pretty far away from us and wasn’t really a danger. But was a pretty big specimen, nonetheless.
As my cousin’s shindig was that evening, after the ziplining I didn’t have a chance to go out–but on Thursday, I made up for it.




During the afternoon, I donned one of my cute summer dresses and went wandering around the French Quarter once again. I stopped at an outdoors courtyard with a band playing New Orleans music to take in the vibe. I ordered myself a frozen drink the bartender recommended (mango), and sat at a table in the shade, listening to the band and doing my normal math puzzle.



Between the heat and the alcohol in the drink, I pretty quickly decided that I would not make a very good day drinker.
I wandered around some more, took some more pictures and then headed back to the hotel for dinner that evening.
After an early dinner, upon my return, I decided a trip to the casino was in order. Time for one of my more fun dresses, a junior’s dress, which I think looks pretty cute on me. I walked over to Caesars, which happens to be the only casino that I have a member’s card (not for the points, but to get into the parking garage at the St. Louis Casino).


After some searching, I found a suitable video poker machine, played awhile, won a couple of dollars, then returned to the hotel.
On Friday, my plane didn’t leave until relatively late. So, I had some time to kill during the day, so why not do it dressed? I put on foundation and powder, and the same outfit from Tuesday. Over the girl outfit I put on a boy shirt and shorts and went downstairs to check out and retrieve my car from valet parking.
I was hoping the coast would be clear, meaning no relatives. Nope. First, one cousin and her husband came and talked to me, and then another cousin. The second cousin looked at my face and said, “do you have makeup on?”
I could have said, no–but it was obvious I did. I just said, “Oh, it’s the Dermatology thing” and she seemed to accept it (I’ve had two melanomas removed from my back, so that part wasn’t too much of a lie). I then went outside to wait for my car to be delivered to avoid any further discussion or cousins.
I drove a couple miles to an area that with a street with several boutique and vintage shops–something different from my normal mall visits. At one vintage store I tried on (and bought) a vintage negligee, so I did not leave the Big Easy without a souvenir.
After about two hours of walking around and nearing the end of my parking meter time, I went back to my car and headed to a local mall. There I had lunch, tried on some formal dresses at Macy’s and some more fun stuff at American Eagle, and eventually cleaned up and headed to the airport.
As it turns out, I should have hung out at the mall longer. My flight ended up being delayed for about three hours, so my later flight became a late flight. I also screwed up by leaving my electronics bag with my triathlon watch, a battery, my ear buds, and a couple of cords on the plane. Ouch.
I filed a report with the airline, and for two weeks, the emails said they hadn’t found my items. Kicking myself, I ordered replacements.
Of course, the next day the airline sent me an email saying they HAD found my bag of goodies! Hurray! I returned the replacement triathlon watch, but kept the replacement cord and ear buds, so I have replacements the NEXT time I lose them. At least I had a happy ending to my trip.



Adding Louisiana to my list of states means I’m up to fifteen states where I’ve been dressed:
- Arizona
- California
- Georgia
- Hawaii
- Illinois
- Indiana
- Louisiana
- Missouri
- Nevada
- New Jersey
- New York
- North Carolina
- Ohio
- Pennsylvania
- Wisconsin
I guess it’s sixteen if you count Victoria, Australia, as a state. 😀
But I’m always hoping to add to the list.









3 Responses
Wow Kandi, it’s strange to find someone apparently so positively ‘out there’ is still hiding from your relatives?
I guess it helps keep the thing alive.
It’s great to see how you are juggling it all.
I’m sure I can never come out to everyone I know and I’m encouraged to see you being successful.
Sandra, thank you but I am not sure which post you are referring to. This particular post is from Dee.
Nonetheless, I try to keep life as simple and balanced as I am able. We appreciate you!
Sandra, yes my relatives don’t know. My wife wouldn’t be happy with me disclosing that info to them (my wife has known that I like to dress over almost all of our 40+ year history). My wife thinks people will feel sorry for her that she is married to a crossdresser.
I’ve only told one person in my boy life (other than ex-girlfriends, because they knew back long ago when we were dating). That person could not be more supportive. My phone outed me to my wife’s best friend, and the best friend os fine with it and hasn’t told my wife she knows.
But Kandi and I are two different people with two different lives but a common interest in getting out and about while dressed.