Telling

I wrote this about two years ago, but have waited for the right time to publish this. I’ve written about my interactions with my friend I refer to here as “Ms. Dee-ism”, but I haven’t shared how and why I outed myself to her.

Recently, I emailed the draft I wrote two years ago again to Ms. Dee-ism, and asked her the following.

<Circling back to this. Are you more comfortable about me putting this out there? If no, I understand. If yes, I will update and refer to you as your proper name, Ms Dee-ism. LMK.>

Her answer was clear. 

<Thanks for sharing and asking – I am completely comfortable! Proud to be Ms Dee-ism too. ❤️>

So now you will know.

Usually in this space I write about a recent outing. This post will be a different kind of “outing”.

A perpetual nagging question for those who crossdress: do I tell someone who knows the guy me about my crossdressing? 

The first time is generally with your romantic interest; tell, don’t tell, when do you tell? I have met two CDs who have not told their spouses, even though they have been married for a long time. I have read similar stories on internet forums where the spouse doesn’t know, and the writer is asking “how do I tell” after hiding it for ten or twenty years (I am firmly in the “tell” camp).

In my case, when I met my (future) wife I never used the words “I’m a crossdresser” but within the first few weeks of meeting she put makeup on me and I wore her clothes in front of her. I also told several of my other romantic interests that I liked to dress, and two of them, Renee and Melissa, helped me dress up (a long time ago). These days, Renee loves to see me dressed in pictures and in person, and I hope to get to fly pretty to visit her again. Melissa and I are still acquaintances, and we usually see a St. Louis Cardinals game every year (guy me), and a couple of years ago I did tell her I was a crossdresser (confirming what she knew anyway). I’ve shared a few pictures with her, but other that that she isn’t really interested. 

But once past your romantic interests, it becomes more problematic about disclosing to those who know the boy you, especially those of us in the older demographics (on the whole, I have found younger folks to be far more accepting). 

For me, except for those who I was involved romantically with, I had never told anyone who knows the guy me that I’m a CD; not my sons, family, or friends. As the saying goes, it’s hard to put the toothpaste back in the tube (or the only way three people can keep a secret is if two of them are dead).

Until April 2022, when I told the spouse of a long time friend, Ms. Dee-ism. For privacy reasons, I’m not going to discuss details, other than I had specific reasons for telling her. I debated with myself for the prior six months whether to tell, and finally decided the pros outweigh the cons.  I weighed all my emotions, figured the time was right, and that Ms. Dee-ism would keep it a secret.

We were both out of town, celebrating a mutual friend’s milestone birthday.  The two of us went to walk our friend’s dogs. I asked if I could tell her a secret, and she said yes, so I told her. We talked about it for a few more minutes, and then a couple of days later for about 45 minutes. She said she felt honored that I trusted her.

After we returned home, I purchased a gift card from my friend Michelle for her salon to give to Ms. Dee-ism. I told Michelle about Ms. Dee-ism, and vice versa, and both were eager to meet each other. Michelle texted Ms. Dee-ism and said we should get pedis at the same time–I answered if that happened then they couldn’t talk about me. I told Ms Dee-ism what Michelle texted, and my response, and Ms. Dee-ism laughed and said “we are definitely going to talk about you.”

That was the start. Things could not have turned out better. Ms. Dee-ism and I swap texts all the time, on multiple fronts–Taylor Swift (she’s a big time Swiftie), the Cardinals (in the last couple of years she’s become a big fan, and I tease her about her favorite current player, who I refer to as the “heartthrob”), Transgender issues, finances, and fashion, of course–usually sprinkled with play on words using Dee instead of simply the letter D. After she comes up with a new one I can see her smiling in my mind.

She’s met Michelle and become a fan of Michelle too. We have a three-way text chain I tagged as “Sistas” from a word Michelle always uses. We’ve been out shopping twice as a threesome, and I’ve introduced Ms Dee-ism to two of my favorite thrift stores (she’s recommended them to others).

When I go out, Ms. Dee-ism wants pictures. She offers her opinions on things I try on (most recently, “buy it buy it buy it”). She’s an early riser, so every Sun-Dee morning when I wake up there is a message telling me how much she enjoyed that morning’s read, and how it gets her day off to a good start. She’s also said multiple times she feels honored that I shared this with her, and that pleases me a great deal.

We have become much closer, and when I needed someone to take me “at the butt-crack of dawn” (her words, not mine) to take me to the hospital for the surgery to remove my twin melanomas (my wife was unavailable because she was out of the country), I knew who to ask, because I knew she would say yes. I did and she did and I will be forever grateful (and my operation was a success).

Telling Ms. Dee-ism my secret has enriched my life–and hers–and I am SO glad I did it.