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Friday Night (High) Lights

Dee has another memorable experience, or had three years ago.....

After over a year off from no triathlons (from February 2020 to May 2021), I decided to load up with seven races in 2021, with five in August and September, including two in Milwaukee for the USA Triathlon National Age Championships in early August. As I had been waiting for the Nationals for two years (I signed up for the cancelled 2020 race in August 2019), I wanted to do well–at least well for me.

I wanted one last prep race before the Nationals, so I signed up for a Saturday sprint triathlon in Springfield, Illinois. As Springfield is about 90 miles from my home, driving up the morning of the race was not an attractive option. I reserved a hotel room…and as long as I had a motel room, I might as well have a Dee outing (yes, that was a consideration in deciding to do the event).   

I was deciding what to do for my outing, when my GG friend Michelle texted that she was available to go out that night. I scrapped my other plans and made arrangements to meet at her salon, and we would figure out what to do from there.

The boy me did a leisurely afternoon bike ride that started and ended at a local YMCA. One feature of our local Y’s is they have family dressing rooms, and a while ago determined I could use the family dressing room to get my girl on. This Y isn’t my normal Y, it’s not very busy, so I can, with some gumption, walk in as a guy and walk out as a girl–and I did, wearing the orange sundress.

I headed to Michelle’s salon (she’s the owner), and while she was finishing up some cleanup duties, I tried on a few different outfits, including a new skirt I bought with two tops Michelle had given me (as we are similar sizes, she often gives me her clothes, and enjoys seeing me wear them).

Then something special happened. 

I have met several of Michelle’s co-workers (the co-workers rent their chalets from Michelle) over time, both as the guy me and as Dee. I am always somewhat reluctant to interact with the co-workers, as they often have clients with them, and I don’t know how either the co-workers or clients will react to me. Just because I am Michelle’s friend (and she never hesitates to introduce me to the people she meets), it doesn’t mean the co-workers will be equally accepting. 

The co-worker who has been with Michelle the longest–about two years–is also named Michelle. I’ve known her for most of that time, but we’ve never talked that much (again, that’s because of me being hesitant to engage). Michelle, a nail tech who does lots of fancy manicures, was doing the nails of a client, who’s name was Chris.

As it turns out, I was trying on an outfit (the black top and skirt), and Michelle and Chris wanted to see how it looked (they liked it) and we started to talk. Chris had some questions, and I have always tried to answer any questions openly and honestly. I have hidden my secret for years and years, and I’ve had few opportunities to discuss why I am drawn to dressing as a woman. When someone is interested enough to ask, I am eager to answer.

Then Michelle (the co-worker, not my friend Michelle) said something that really touched me.

She said that she admired the way I lived my life and that I was (paraphrasing) strong enough to do what I liked to do. I was surprised–and very happy–to hear that.
I’ve written before the one thing I truly want is acceptance. My wife tolerates my dressing, but she doesn’t give me acceptance. My GG friends–Michelle, Renee, Karla, Falon–accept me. 

To hear those words from another person, who I didn’t really know very well, meant a lot to me–so much so I later wrote Michelle a thank you card, which she appreciated receiving. I also eavesdropped a bit on her conversation with Chris, and found out that she had gotten several tattoos, and was reluctant to tell her mom about them (and I think my actions gave her a little more courage to tell her mom).

After that high, we went to Michelle’s house so she could change into going out clothes. She showed me a slinky new dress that she had, so of course I had to try it on too, along with some heels I had found advertised on Facebook. I ordered pairs for both of us; her size arrived, my size never did. 

I changed into a favorite black and yellow sundress, and we headed out with her boyfriend to a new charcuterie/bar for drinks and dinner. We had a good time, saw a friend of Michelle’s that I met last year at a local bar (she was happy to see me), and I finally left just before ten, as I had a 90 minute drive to my motel (I changed into my guy clothes before I checked in). It’s always fun being out with Michelle. 

P.S. As to the race, as I was leaving the motel to drive to the race location, it started to rain. It rained before the start of the race, quit for a short time during the swim leg (of course), and then resumed raining cats and dogs for the bike leg and the run. With two out-of-town races the following weekend, I decided having a bike wreck that would put me out of action wasn’t really worth it, so I rode relatively slowly, and ended up last in my age group. For that day, better safe than sorry was the right strategy. At least my Dee time the night before didn’t get rained out.


7 Responses

  1. Dee,
    What wonderful outfits you are wearing. The first one would be be great for the office. Those scrappy gladiator heels are just fabulous. I think your having such great gg girlfriends says that you can be a woman of substance and not just an occasional cross dressing husband.

  2. Dee, the new LBD and heels look awesome on both of you! I am in total agreement with you that acceptance is preferred over tolerance. It is so meaningful to read of your fun and interactions with your GG friends.

  3. Thanks ladies!

    Michelle is very kind to let me try on (or wear) her clothes. She gets almost as big of a kick from seeing me in her clothes as I do wearing them (almost).

    With her, never a dull moment.

  4. Great outfits, Dee and I love your shoe choice. I would even take tolerance for me if I had the choice. Good luck in the future triathlons.

  5. Ah Dee there is no way to truly measure how much I enjoy your postings and pictures.

    How did Michelle go from modeling to owning a salon?
    I’ve always wondered.

    You stay true to yourself in these difficult times.

    I love that, and so many other things, about you.


    1. Thanks as always Renee!

      She was a model when she was a lot younger, but it was part-time. She’s posted pictures on Facebook of her shoots from long ago.

      The evolution from her early days to now she has shared with me. The owning a salon was just hard work and determination. She was working for a chain salon (that’s how we met; she was at the salon and I was randomly assigned to her to have my nails done for a Dee train trip to Chicago). She wanted to be her own boss.

      She asked me for her opinion about opening her original two room salon and I said it was risky. She ignored my advice, survived Covid, and has expanded into a much larger place. She now has over ten stylists at the salon that rent chalets from her. As she likes to say, she is farm tough. In short, she made the transition through sheer will and determination, and I couldn’t be more proud of her, and very proud to call her my friend.

  6. Hi Dee, it is excellent to spend time will gg friend and also through then to get the acceptance of other women. I only go out a couple of times a year with an ex girlfriend and a group of her friends but it is such a great experience. They have my back in difficult situations and also initiate passive and affirming ones. You have a great relationship with Michelle that really enhances your life and I look forward to reading your adventures.

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