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Fore!-Part 2

As I explained last week, my golf group goes on an overnight trip twice a year, and this time around I brought along my girl stuff for a hotel room photoshoot.

Or so I originally thought. 

Also as I wrote last week, my GG friend/former FWB Renee and I swap texts often. She provides feedback, support and helps me build anticipation of my next outing. Me: represents texts from me and Renee: represents responses from Renee.

<<Me: There’s a casino about 20 minutes from where we are staying tomorrow night. Thinking about visiting if I can work out the logistics of getting in and out of the hotel without being seen by the 20 other guys on my golf trip.>>

Then reality set in…

<<Me: Probably won’t go out tomorrow. I forgot my high school buddy has joined the group so we will probably hang together, and the Blues game starts at 9 PM. However, I will pack my makeup, wig, and a few selections and if it’s not too late I will do a photoshoot.>>

As my golf group is mostly older guys they tend to drop off early; the big excitement was about half of our 19 strong crossing the street from the hotel for ice cream at Dairy Queen. By 8:30 or so, everyone had retreated to their rooms. I walked out into the parking lot and moved my car closer to the back door of the hotel. My room was well placed on the second floor so I could make a quick getaway if I wanted to.

And I wanted to.

I ran a bath to do some manscaping. I laid out my makeup on the counter next to the sink, a luxury I don’t often get. I also had time to do my eyes, because on the flip side I didn’t have to worry about removing all the eye makeup upon my return home. I was taking extra time to make extra sure my golf buddies were down for the night.

<<Me: Going to dress and hit casino>>

I knew what dress I wanted to wear out.

<<Me: The story behind the dress. I bought this for <my wife> one Christmas when we lived in Sydney 20 some years ago. She really never wore it and abandoned it so I claimed it. For the longest time, it wouldn’t fit. Then it barely fit sans boobs. This is the first time I can wear it with my padded bra. Love the dress, love how it looks on me. First time wearing it out.>>

After trying on this dress time and again for a long time, losing enough weight (round numbers, I’ve lost 60 pounds since retiring in 2012, a combination of eating better and lots of exercise) to have it fit so I could wear it out was a BIG victory.

<<Me: Made it to casino. Will try to get full on picture.>>

Renee likes to see my picture. Like most CDs, I like taking pictures. The camera (well, these days, phone) reaffirms that I’m actually out dressed–I’m actually doing what I’ve wanted to do forever.

I found a unisex bathroom and took my picture. I also walked around and took a few selfies. I’m not a big gambler but casinos are a good destination because they are always open, you can get a drink if you want, or watch a game on TV. The downside is cigarette smoke (I hate cigarette smoke). 

I play video poker for low stakes, and being the analytical type, followed a poker website on my phone for the best strategy of how to play each hand. I played a couple of hours, arriving around 11:15 and finally called it quits at 1:15, breaking even on the night.

<<Me: Happy to get out. Golf tomorrow is rained out. Planning to dress and drive back to STL and visit a mall. Will be driving probably 9:30 to 11 AM your time if you want to chat. Night…>>

I knew Renee wouldn’t be reading this until the morning, as she is an hour ahead of me, and definitely past her bedtime. 

Then this happened, as recorded in my text, which I typed in my car immediately after it happened. 

<<Me: Ok, that was interesting.

Leaving casino at 1:15.

Black guy behind me at exit. “Nice dress you have on”.

I softly say thank you.

He repeats “nice dress you have on”.

Him: “You work out?”

Me: “A lot.” 

Then, “you married?”

Me: “Yes”.

Him: “You into black guys?”

Me: “No.” Then I add, “not into guys”.

I think I have officially been hit on.>>

That was the text I sent Renee at 1:24 AM.

I’m not sure if he thought I was a GG. I wasn’t sure how to react. Should I be flattered?
I drove back to my motel, and entered and went to my room without seeing anyone. I wasn’t worried about other hotel guests seeing me, just members of my group. Either way, it was not an issue.

I stayed up another hour or so, trying on different outfits I had brought along, along with some lingerie (some of the pictures were shown last Sunday). I also recorded a short video for Renee, then cleaned up and went to bed around 3 AM.

The next morning, Renee texted back with favorable comments on pictures I sent. We swapped the following messages.

<<Renee: Great video. And yes you were definitely hit on. And handled it well.

<<Me: Thanks. Glad you liked the video. I assume he knew I was a guy but not sure.

<<Renee: Probably didn’t. Enjoy the compliment. When do you hit the road?

<<Me: Wanted to leave later than everyone so wouldn’t run into anyone in Dee mode. Golf cancelled. Will probably leave in a hour. If <guy name> were leaving, on the road in 20 minutes. Dee takes longer. 😄

<<Me: I want to say I was flattered to be hit on but are women flattered or annoyed when they are hit on?

<<Renee: To be honest it depends. When I was in college, usually saw it as a compliment. As I became more radicalized definitely not. Lots of topics for discussion.>>

We made arrangements to talk during my drive home and I started getting dressed for the drive home, taking my time to make sure the coast was clear. That will be Part 3 next Sunday.


5 Responses

  1. Great incidence with the guy hitting on You, I would have loved it, but Id had never yet had the courage to get out.

    1. Thanks. I was surprised. I liked the way I looked, but it was a late Monday night at a rural casino and I sure wasn’t expecting it.

      As to courage, I prefer to think of it as just overcoming our fears. We build up a hundred reasons why we shouldn’t go out. Trust me, I know, because I was the one who couldn’t overcome the fears.

      Until, from reading tales like mine, I did overcome the fears, and stepped out dressed–and nothing bad happened.

      In actuality, lots of good happened. I’ve made friends, gone out lots, and done what I’ve wanted to do for over 50 years–and lived to write about it.

      As have Kandi and Julie and Sherry and the others here who post their stories.

      These days, with the internet, it’s easier to find a support group. There are forums to offer support and guidance. There are trans friendly companies like Sephora and Nordstrom that can help with makeup and clothes (they did for me).

      Get vaccinated and get out, because the world is opening up again. Take a small step, and then another, and finally after you get out with no fuss you’ll ask yourself what took so long.

      Then please come back on a future Sunday, and write a comment about how you did make it out. That would please me to no end.

  2. You have grown exponentially in the 30 plus years we have known each other.

    I applaud your openness and honestly.


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