Dee’s Unexpected Evening!

“I get off work at 5:00. Wanna go out?”

My friend Michelle and I had been trading texts on a Friday night when that text popped up on my screen. I quickly texted yes (my exact phrase was “abso–f’ing–lutely”), we made plans to meet, and I made reservations to a steakhouse in a famous hotel in the Central West End of St. Louis.

I’m Dee, previously featured in Kandi’s Land when I visited Cleveland (and met Kandi) last August to participate in the USA Triathlon National Age Group Championships. We had two fun evenings out together and have stayed in touch (as to the race, I suffered a flat tire, and an hour and twenty minutes of waiting for repair support, and finished last–of 132–in my age group).

Like Kandi, I’ve had long term desires to crossdress (over 50 years). Only in the past 2+ years have I conquered my fears of going out dressed in public. Two years ago, I did a four day train trip from St. Louis to Chicago dressed as Dee. Before I departed, I went to a local salon (in drab) to have my nails done. The salon worker was Michelle, and in the time it took for me to get “girly” nails, we hit it off. Michelle wasn’t merely supportive of my crossdressing, she was almost giddy. Since then, we have texted often, gone thrift shopping several times, plus a few lunches and one prior dinner.

Dee on the left……

A few days prior to our dinner, we met at her house. She had done a spring cleaning, and thinned out her wardrobe. Instead of donating her clothes to a thrift store, she saved them so I could see what I wanted. Heaven! I spent two hours trying on her hand-me-downs,  and ended up with a treasure trove of tops, skirts, dresses, and even a pair of skorts. Michelle loved seeing me model her clothes, which made me feel good. After trying on all the items, I donned a skirt and top from my new collection and we ventured out to lunch at a pizza place.

So after confirming our dinner plans and making the reservations,  I went back on line to make an appointment with Michelle to get my nails done. This time I went in Dee mode, wearing another skirt and top combination I had received from Michelle. She had seen the appointment, so it wasn’t a complete surprise, but she was happy to see me and catch up in person, instead of texts. I had about 4 hours to kill before I was due at Michelle’s house to pick her up, so I hit the local mall to get some retail therapy (mostly just trying on dresses and clothes, a favorite activity of mine.

I arrived at Michelle’s house around 6:30, carrying three dresses, two I wanted to model for her (including a black lace dress she had given me), and the dress I planned to wear to dinner, a velvet turquoise sleeveless dress. Never in my wildest dreams did I think I could wear a sleeveless dress, but I found this one at Nordstrom several months before and fell in love with it. 

It took three trips to finally buy it, finally convinced when another friend texted me and said I had to buy it, and I could work out where to wear it later. I have recently returned from two months of summer in Australia, and while there I would occasionally run with my shirt off to even the tan on my shoulders, so if I did have a chance to wear this dress, I wouldn’t be sporting a farmer’s tan (yes, I’m vain).

I paired the dress with black hose and my ankle strap black heels. Michelle wore a form fitting black jumpsuit (and she definitely has the form to fit into it) with a lace back, and high enough heels to slightly tower over me (Michelle had bought the heels when we were previously out shopping together).

We arrived at the hotel about an hour before our reservation and had a walk through the halls and lobby. Michelle had never been to the hotel before, and she was dutifully impressed. In addition to banquet rooms and the like, the hotel also has five movie theaters. During our walk, we stopped in front of a mirror to get a picture, and a hotel employee graciously offered to take our picture, and we graciously accepted.

We went to the bar and ordered wine (Michelle) and margarita (me). We talked while she texted a guy she’s been dating, seeing if her friend could figure out where we were (no). The bartender also took our photo too.

Dee on the right….

Soon it was time for dinner. The restaurant is an old style steakhouse, with muted lighting and lots of exposed wood. Michelle ordered a gimlet and it was my turn for wine. The drinks were perfect; Michelle had never had a gimlet before but loved it. Michelle also loved looking at my nails. She said she never gets to see her handywork–her customers finish and leave. I love having my nails done too; this was only my third time (and I was sad the following morning when I had to remove the polish for a tennis match).

The waiter let us talk and finally took our orders, a New York strip for Michelle, and beef tenderloins (the restaurant’s signature dish) for me, and sharing a salad. Michelle’s steak took up most of the plate, so she had enough to take a large portion home. My appetite wasn’t ladylike; I managed to clean my plate. We also made short work of a piece of carrot cake that we shared for dessert.

After dinner we returned to the bar, where a band was now playing. We found a table near the band and settled in for a few songs. Eventually,  they played a song we could dance to so we joined the dancers on the floor. As Michelle is used to heels, her dance moves were a little more expressive than mine, but I did okay, considering it was my first time dancing in heels.

As Michelle is gorgeous (in her earlier days she modeled), she was quite popular on the dance floor. On the other hand, I was a bit self conscious. Like Kandi, I make no illusions about passing. I assume people know I’m a guy in a dress; my goal is to make sure it’s a pretty dress (mission accomplished).

At one point, a woman came to me and asked “what’s the story between you two?” I didn’t really get a chance to answer other than to say, “she does my nails”. I also got asked to dance by a woman and a guy, but I begged off, because my feet were suffering by that point, and I was comfortable just sitting on the stool and enjoying watching Michelle dance.

We lasted until around one AM and I managed not to turn into a pumpkin. It was definitely fun for me and something I had wanted to do for a long time, but never thought I would have the chance. Now I’m hoping for another time.

As a postscript, Michelle did a Facebook post of our night out, with the tag line, “Fun night! Thank you!!!!” with a kiss icon between the two, and three pictures from our night out, including one that just shows part of my shoulder (that picture is now her main picture on Facebook). The post got a ton of likes and a dozen or so comments. When she went to her yoga class the following Tuesday morning, her teacher and classmates who had seen the post wanted pictures, so she shared…

My sincere thanks to Dee for this story, pictures and her sharing with us! She’s a good friend.


9 thoughts on “Dee’s Unexpected Evening!

  1. Dee, & Michelle & Kandi,

    An absolutely wonderful GIRL story – -This GIRL thoroughly enjoyed it . Could experience the entire adventure through the choice and flow of words. OF course the Photos were SUPER and were the cream on the cake.
    Glad all had fun. (Dee you are very fortunate to have Michelle as friend)

    Marie Anne Greene


  2. Dee, such a lovely evening with Michelle, you both look fabulous! And I am so in awe of the beautiful friendship you have with her. It’s such a validation of being ourselves that some people want to be with us, as they know we are no different from their other friends. Having a great time at the restaurant and bar is icing on the cake! Love the pictures of you two!!


  3. Thanks all.

    I texted the post to Michelle this morning (she knew it was coming) and her response was “I love it so much”, and that she was texting it to her boss at the salon.

    Yes, I’m lucky to have made several GG friends that provide me advice and emotional support. As Kandi has found out and I can confirm,, there are many friendly people out there, and the only way to find them is to get out and be visible.


  4. The more any of us get out and about and mixing with the civilian population the better it is for all of us. You look great and the smiles you are both wearing tell the story


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