Caden’s First outing, from Disney World, and beyond…

Okay, so while commenting on , I decided I need to post a few of my outing/trip reports from 2014, which was the first year I went out anywhere as Caden. Contextually, it shows my growth as Caden, and provides historical context. But it also shows a basis of experience. Although vast swaths of my experience stem from elsewhere other than my outings. But a good trip report is always fun, and in the case of crossdressers, they are inspiring. Inspiring in that other crossdressers will read them, and they may be inspired to finally step out from beyond their front door, and do something they fear.

So without further ado, here is my Walt Disney World Outing report, first posted May 30th, 2014 on my Sorority Website;

It was literally my first outing as Caden. I had never gone anywhere as Caden before this. Usually, plans I made would get squashed or fall through. It was never really about a mental block or getting to that front door and freezing. I had simply put, never really had the opportunities. I had only within the last two years fully dressing and gathering outer clothes, after having expressed to my Loving Girlfriend my desire to go out dressed.

Anyhow, we’d been planning a two day trip to Disney World. Four parks in two days, it CAN be done, even on Memorial Day. You just have to be an avid fan like she and I. So my wonderful girl friend asked me if I’d like to take the opportunity to do dress as Caden, so I jumped at the chance. She is like the best I could have ever hoped for in a partner. At first I thought she had meant go to a park as Caden. But she quickly explained her plan; I would dress as Caden for the return trip home, which meant five amazing hours as Caden, some shopping, a few meals, and a lot of experience to be had.

It would mean changing in the car after dinner before we got home, but the opportunity was there, so I took it. So Monday and Tuesday we did the parks, and Wednesday was our travel day. Most of the weekend, we were able to joke and have fun with Caden’s coming road trip. My favorite joke was that at Disney we all have a little Princess in us all. I was certainly feeling that way at least. But I also inquired if perhaps on one trip back to Disney, if Caden may get a day or two at the parks, my GF was not opposed.

I woke up early of course in my obvious excitement, but NOT early enough and began my routine of getting ready. In retrospect, I should have prepped before we arrived, and simply maintained while we were down there. It simply tok FOREVER, being in a hotel bathroom did not expedite things at all. By one one o’clock we were dressed, packed and leaving out the door. Sincemy GF was still packing, I had to drive her car from the parking lot to the curb, while wearing heels to pickup our luggage, which was a first. And apparently I don’t travel light as Caden or my drab self.

First order of business once the car was loaded, was to go by the hotel gift shop to get my traditional hat. But tradition went out the door because I’d never done it as Caden. It felt so liberating to walk around the resort dressed as Caden. Staff were easy going and receptive as well, IF they noticed at all, I really have no metric to know if they did or not. None of the other patrons seemed to even notice.

I found my hat, as well as a Minnie Mouse bow charm and a pink crystal mouse charm for the charm bracelet my girlfriend lets me use. I also bought a Minnie silhouette pin for my pin trading lanyard. All to commemorate my trip as Caden.

We finished shopping, checked out of the hotel and were on our way to a crossdresser boutique in Orlando called Ritzy Rags Wigs and More. If ever in Orlando, and wanting a wig, that’s a good place. I certainly got a feel they wouldn’t ever sell me a bad wig. Even their low end wigs were nice. The staff had me set up great by my second wig. They didn’t let me leave the store until I knew the proper care of the wig, provided me with a sheet to remind me and were so very helpful.

They had limited stock on other accessories. But they were able to help me properly size for my shoes. Turns out I’d been buying and wearing the wrong size. Also bought some new foundation the owner recommended, Kryolan TV Stick. She said that it has the right red colors to hide the blue from beard shadow. She told me to drop kick my dermablend to the curb. She said it wasn’t the same since they had reformulated it. The owner is a famous local drag queen in Orlando. She also recommended a Ben Nye setting powder that gave my skin a much healthier glow and made it seem more lifelike and vibrant. Will post the color when I remember it as well.

So we left Orlando with me wearing my new wig, and headed to Jacksonville for dinner. We went to PF Changs, where I had my First Ladies room moment there. Oh dear Lord, if you are going to wear hose and a dress, practice juggling the panties, hose, dress and sweater before trying it in public. I had never even thought about it until I was actually doing it. But that went smoothly, well, at least nothing got damp. So we went to our table and ordered dinner and wine. Well my girlfriend did since I was still worried about being carded and my voice. I did turn a few heads, so I know I was clocked. But the ladies were at least polite. The waiter repeatedly called me miss and us ladies. So if he knew he never batted an eye.

Once back in the car, Caden had to leave. And after a full day as her, it was hard to let it go. But it gave me resolve that as easy as that day was, there can and always will be, other days. Some better, some worse. But they are all worthwhile experiences to be had. All we can do is create the opportunity and reap the rewards. I feel blessed and rewarded by the day that my beautiful girlfriend gave me that day. As far as first outings go, it was simple and fun, lighthearted and an awesome experience I will treasure forever. Thank you Honey.

I hope you enjoyed reading it. I hope it inspires somebody out there to do something similar.
Ever & Always,
Caden Lane

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