Back in October I celebrated my eighth anniversary of going out regularly. By “celebrated” I mean I didn’t do anything special as Dee–because I was on a cruise ship touring Greece, Croatia, and Italy, as part of a five week trip to Europe and Morocco (my boy life doesn’t suck, either). But it’s time now to take a look back, and see where I’ve been.
For the longest time, I daydreamed about going out in public dressed (I’ve wanted to dress since I was seven years old, or thereabouts). As I got old(er), the urges got stronger. First buying some clothes (or asking my wife for clothes and makeup as presents), then dressing at home, and then occasionally doing the night time drive. Then a Halloween or two out, and a day-and-a-half outing in San Francisco at the tail end of a boys golf trip to Reno, Nevada.
Finally, in the middle of 2016 I decided–after reading blogs and forum messages about others going out–“Why not me”? My wife was going out of town for four days near the end of October, and I had a couple of months to plot my four days out. I ended up getting my fingernails done, getting a Sephora makeover (I listened and learned and it’s how I’ve done my makeup since), trying on dresses at Nordstrom (and met my friends Falon and Karla because of that), and went in person to buy a new wig. I bought two dresses, a boatload of makeup, and have never looked back.
Since then, I’ve been out probably a thousand times, in twelve states, or thirteen if you include the state of Victoria, Australia. I’ve dressed to concerts, musicals, baseball games, restaurants, bars, casinos, flown and trained pretty, and shopped at more stores than I can count or remember (and have lots of clothes from those shopping trips).
Prepping for a train trip to Chicago in 2017, I booked an appointment to get my nails done at the same place I’d had my nails done six months before. My prior nail tech (who was fabulous) was unavailable, so I instead was matched with a crazy lady from Arkansas, who immediately spilled her life story in the 45 minutes she did my nails, while I explained why the guy sitting across from her was getting his nails done. I promised to come in dressed upon my return from Chicago, which I did. Michelle and I have been friends since, and we’ve had a lot of fun.
I joined a local Transgender group in 2017 and that gave me the opportunity to meet fellow travelers and learn their stories, and to join others at monthly lunches and dinners. I accidentally posted something on Facebook multiple years ago, and that led to a reconnection with Renee, a former girlfriend who helped me dress (and bought my first pair of heels) in the late 1980’s. For some reason, she loves to see me dressed. I visited her last year and she got to see me dressed in person, plus I enjoyed a Bruce Springsteen concert with her husband John, dressed to the nines, of course (as requested by Renee).
In 2022, I came out to Ms. Dee-ism, the wife of a friend–the friend I’ve known since high school (almost 50 years), Ms. Dee-ism for 30 years. She was not only accepting, she was enthusiastic, and she’s met Michelle (like me, a big fan of hers), and I titled our three person text “Sistas”. We share life stories and pictures (of course) and have enjoyed joint shopping trips, and one day hopefully one day we’ll get joint pedicures from Michelle–matching colors, of course.
Ms. Dee-ism’s current mission is to find me more shades of lipstick; she’s bought me two reds already (she’s a Swifty, so they are Taylor Swift reds), and is looking for more! What’s not to love about that?
The highlights have been many, and I look forward to many more. I hope my stories encourage at least one of you out there to make the step out the door, like I did back in 2016.
7 Responses
Well done Dee. What a woman.
Your variety of outfits is impressive, as is your wide range of outing locations.
Jocelyn
Thank you, Jocelyn.
To be honest, my actual times out and experiences have far exceeded my daydreams. I have also Dee-finitely expanded my wardrobe choices over time!
Dee,
The stories of your adventures, especially with your BFF Michelle, are inspirational to us all. (BTW I would love to have a BFF like Michelle, yes envy.) And like Kandi and our correspondents here in K-land, you demonstrate what it can be done.
Here’s to many more anniversaries.
Cali
I was, and still am, thrilled by being part of Dee’s world.
Cali, thanks also.
I got lucky in meeting Michelle, but I took the risk in going out and asking for what I wanted–my nails done–and then took the risk to follow-up. Nothing ventured, nothing gained. By the way, I went to her 50th birthday party last night, and that story will show up in a few weeks (i.e, when I get around to writing it up!).
Renee, glad you are part of my world.
Once again, Renee was a calculated risk. We met because in the days before dating apps, there were personal ads in papers. Renee submitted an ad, I wrote a letter, we met. I steered the conversation to dressing, and she offered to buy me heels (and did; she never liked wearing heels, but I did and do). This was the 1980’s; it could have blown up in my face, but she was–and is–receptive.
Ms. Dee-ism, was another calculated risk. I had reasons to out myself to her, and it could not have turned out better.
Sometimes things happen. Sometimes you have to make them happen. Luck helps too.
Dee,
I agree, sometimes you need to risks to get what you want.
I also wanted nails and ‘fate’ took over. Now, I have polish toenails all the time and NEED acrylic fingernails. And heels turned out to be a great solution.
Keep on living your best life.
Cali
Cali, I am certainly trying to live my best life–and back at you for living yours.