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Dee Day!

I figure this is a post where half the readers will swear off social media (or say that’s why they don’t use them) and the other half will think “OK, that’s good to know.” I’ll get around to that story eventually. 

Back in middle June I had three outings in an eight day (“Dee”) period. The first Satur-Dee was the monthly luncheon of the St. Louis Gender Foundation. We alternate between a couple of nice restaurants in St. Louis County, and usually have a handful of attendees.

My back had healed enough from the surgery to remove the melanomas from my back (all good news, no spread–and again a PSA to have a dermatologist look you over to see if you have your own ticking time bombs that need to be defused) so that I could wear my new summer dress, a favorite from White House Black Market. I originally tried it on in Phoenix in March, loved it, but not the price. I cyber stalked it until the price fell to my buy zone, then went to a local WHBM to see if they had it in my size. The local store didn’t, but the SAs called another store (in California) that did. Shipped for free, it showed up in our mailbox two days later. Another bonus– an unexpected additional discount, so I paid about a quarter of the original price. A big win for waiting (I’ve since done the same for another dress I like).

Lunch was enjoyable, catching up with the group (I often have conflicts on Satur-Dee afternoons, so I hadn’t attended in a while). One big selling point of the lunches is that it gives me a justification to tell my wife that I’m going out dressed (she’s tolerant, but not overjoyed I go out in public dressed). Afterwards, I usually make a side trip to West County Mall, which has a Nordstrom, WHBM, Akira, Macy’s, Windsor, and H&M, all stores I frequent. 

The following Fri-Dee night my wife went out to dinner with a friend and my son was working (he lives with us but works most nights), so I decided to hit a local casino. I hit a big (for me) pot at video poker–four aces for $40. Mostly I have to write about this because Kan-Dee loves cheers photos of me.

Editorial comment: These photos are actually labeled “Dee Cheers” in the backroom of the blog and it was actually not my idea initially. Michelle (not THAT Michelle), the brains behind the blog, had the brilliant idea.

The real story starts the next day, or more exactly, the following Sun-Dee. On Satur-Dee night we had a STLGF dinner, so I stopped at the Galleria Nordstrom and tried on some outfits, including a colored knit top I stalked for a while (and would eventually buy). I also tried on a summer dress, black with white spots and a bottom floral trim. I wore another favorite summer dress, a yellow and black number that suits me well. After dinner, I stopped at another casino, but no repeat of my good fortune from the night before.

Sun-Dee afternoon I was working in our yard (we have lots of trees and plants so there is usually something to do) while listening to the radio on my phone. All of the sudden my phone started acting up in my pocket, going crazy, a butt dial on steroids. I didn’t think that much about it, until I see a message on my screen, with the picture of the black dress with the white dots, and a single word, “Gorgeous ❤”.

My phone had, on it’s own, sent a Facebook story with that picture. My reaction, oops–or maybe a term stronger than that. And at least one person had seen it, and had made the “Gorgeous” comment.

I immediately deleted the story, and began work on damage control. 

The person with the comment is my wife’s best friend, and matron of honor at our wedding. We met originally in 1985, so we’ve known each other for 38 years. 

Here was our text exchange; mine in bold, hers in italics.

Well, you weren’t supposed to see that…

That was a butt dial…

ha ha…

My phone did it on its own while I was out in the yard

omg…that’s scarry

Well, you kind of know my secret but please keep it to yourself I accidentally sent it

no worries….

Yes <wife’s name> knows I do this. No she doesn’t like me going out, but I do.

So please don’t tell her but I do trust you


Don’t tell her you know, I mean

ok that’s what I thought you meant

And I hope you don’t think less of me. I’ve had the desire since I was 7 years old.

I’ve joined a group and gone out the last 6 years. Yesterday we had a group dinner, and this was before.

no I don’t think anything your still <male name> to me.

Thank you.

And she responded with a thumbs up emoji.

We texted a bit more. I sent her a picture of the yellow dress I was actually wearing, and she texted back I had good taste. She asked what brands I like, and besides Princess Highway, an Australian brand (like my wife, her best friend is Australian and lives in a Melbourne suburb) and several American brands, like my favorite, Maggy London. She repeated that finding out didn’t make any difference, that I was still <my male name> to her.

This happened on June 20, more or less over three months ago. We haven’t messaged since then, and because of the distance, haven’t talked face-to-face since then (although my wife does video calls with her from time to time). But I do trust that she will be discreet, and I don’t think it will be an issue going forward. 

To me, it’s another example of how we in the crossdresser community overestimate the risks of being “outed”. I’ve told one person in my male world–Ms. Dee-ism–and she could not be more supportive and accepting. The store owner of where I buy my wigs is the mom of a high schooler I coached for three years, and to her it’s not an issue (she’s actually instead asked me for financial advice). It also appears a high school classmate, a client of Michelle’s, has deduced Michelle’s friend Dee is also me. This has all happened and the world hasn’t ended.

I often say crossdressers–especially those of my age demographic–are afraid of our own shadows.

I was too for almost the first sixty years of my life–until I decided I was just going to take the risk. Instead of rejection, I’ve found acceptance and approval. I’ve NEVER had a bad outing (over 500 times and counting), and lots of really good ones, including multiple times the last two weeks.

In a lot of ways, that is indeed “Gorgeous”.


2 Responses

  1. You’re right, Dee. By and large people are quite happy to live and let live. I’ve been out in public for more than a dozen years now, and never had a bad experience. I have come out to many former colleagues and no bad experiences there either.

  2. Dee,
    Technology is both a friend and a almost a feared enemy , it serves us well when we want to communicate with chosen ones but will sometimes bite you in the butt when it decides it’s smarter than you , for that reason we know we could be living dangerously at times .
    I made a wrong decision when I considered a mutual friend could be on my side . The story being a trip to Alcante to stay with friends and I thought it wiser to send pictures of me dressed to explain my lack of body hair while out swimming . Nothing was said on the trip but the irony was we came across a transgender running a charity shop with their family , my male friend actually bought a second set of golf clubs from her .
    The problem in your case was putting a friend of your wife in a difficult situation , would she stay loyal to your or with your wife ? It would be out of your control if she did decide to spill the beans .

    It’s why I prefer to be full time but to say I have no secrets from anyone would be untrue as many people don’t know my male side .

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