I belong to a golf group that golfs twice a week (mostly retired fogies who try to avoid bogies). Twice a year, once in the spring, and once in the fall, we have an overnight outing where we drive a couple of hours, play a round, spend the night at a hotel, play a second round early the next day, then drive home.
At some point a few weeks before I realized I could do the time immemorial practice of crossdressers, the hotel room photo shoot.
I have a GG friend Renee. A long time ago we were FWBs and she encouraged my first forays into dressing and bought me my first pair of heels. Thirty years later via Facebook we reconnected, and after she accidentally found out I still dressed (I came close to outing myself to lots of people on Facebook), we have messaged regularly and talked occasionally.
In her own words, she likes seeing me dressed up–and I love having someone I can share my thoughts and pictures with. It’s great to have a sounding board–and she loves the shout-outs on my blog posts.
Part of my pleasure of dressing up for me is the anticipation. I don’t get to do it that often–especially lately–so thinking about where to go and what to wear (decision, decisions!) is all an integral part of the process.
Often, messaging with Renee is also a big part of the build-up. I’m going to add to the narrative with some of those texts.
Me: Going on an overnight golf trip Monday/Tuesday. Staying at a hotel. Thought I might take along my Dee stuff and shoot some pictures. Still have a few items from Michelle I haven’t taken pictures of. Any requests?
Renee: Surprise me. I doubt that I’ll get to meet Kandi. The family has scheduled lots of activities. Damn.
Me: Ok. Not sure how much stuff I’ll take.
The background is that Renee is from Cleveland, was making a trip to Cleveland to see family, and during the trip wanted to meet Kandi. I had previously passed on the request to Kandi and Kandi was all-in. But as Renee noted, meeting was not to be. [Editorial comment: 🙁]
Finally around 9 PM I began getting dressed. I sent Renee a few “getting ready” pictures. I tried on three dresses my GG friend Michelle had given me recently (the two black and white sundresses, and the strapless dress) and a halter dress I found recently at Goodwill (which I was iffy about keeping, but Renee was all-in on it, so I kept it). Of course, I sent the pictures to Renee.
After I text the pictures, often Renee responds with comments on the photos or stickers.
For the three pictures of the strapless dress, Renee texted “Excellent 3”. The others include her comment and sticker.
In addition to dresses, Michelle also gave me some lingerie, and Renee likes pictures of me in lingerie, so I took a few of those too….
More next Sunday.