Pinkfest 2019 — Part 2

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Welcome to part two of my recap of Pinkfest 2019. At the end of part one, we left off on the Thursday night, where the gang finished the night at a blues club. After getting back to my hotel and my makeup off, this girl got to bed around 2:30 a.m. (See this link for part one — the first two nights of Julie’s attendance at Pinkfest 2019).

Friday morning I was glad to be waking up at my hotel rather than at home, where I would need to help get the kids off to school. After a little breakfast, some nicotine, a bit of catnapping and a shower, I was ready to again get on the warpaint. A year prior, I had the same experience of rushing to get ready and ended up forgetting to brush my teeth and had to buy a toothbrush at Walgreens to use in the Nordstrom’s ladies room. This year I almost made the same mistake and laughed to myself when I avoided that rookie mistake. 

Finished getting ready at exactly 11:30, met Sandy in the hotel lobby and we headed out for the block and a half walk to train — just as the sky opened up and drenched us. We had umbrellas, so it wasn’t a disaster and luckily my sparkly flats are so thin that they dried out rather quickly. Lunch was at the Walnut Room in the Macy’s on State Street. In attendance was Ajay, Julie, Michelle, Sandy and Vivian. (After years of going to this place with family, it wasn’t until that day that I figure out that the name comes from the walnut paneling on the walls.) The waitress was super friendly and Ajay was really impressed with how reasonable the prices were for such a fancy restaurant. 

After lunch we were scheduled to go to the Art Institute, which I said I would be fine with skipping and just spend the afternoon shopping at Macy’s — mostly to avoid the rain, but also cuz I was dragging tired from the night before. Apparently, I was the only one afraid of the rain, so we headed out — stopping at Millennium Park to get some pictures with ‘The Bean.’ We were lucky in that there was a break in the rain and we got some really great, totally touristy pictures — although we did get a bit wet on the short walk to the museum. At the museum, it was a little odd, cuz everyone kinda went in different directions — it’s a big place and I guess everyone had different objectives. I hung out with Vivian and helped her get some pics with some of the more famous impressionist paintings. After about an hour, I got a bit itchy to head back to the hotel — to make sure I had enough time for an outfit change.

While my ‘sophisticated lady LBD’ was perfect for department store lunch/museum visit, the evening plans called for the ‘50s style white dress I had gotten for myself as a Fathers Day gift. Why was that dress important? Well, that night we were going to see a play called Casa Valentina. It takes place in the early ‘60s and is about a Catskills resort, where crossdressers of the time could be themselves without judgement or scorn. It was written by Harvey Fierstein and apparently he did his research, cuz he got just about everything right and put the story in perfect context. Many of us were brought to tears. Michelle was especially touched. Before the show, I asked if they had had any other CDs attending the performance? They said not that they had noticed, which surprised me cuz it this was the last weekend of their month long run. At the intermission, I asked if the cast would be interested in getting a pic with the Pinkfest group. They were very interested and after the show we got maybe the best picture of the week, which included the cast along with Brandy, Julie, Martha, Michelle, Sandy and Vivian. It’s hard to say who was more excited to meet the other group. They were so interested in our expert feedback and we so much wanted to let them know how much we appreciated them for telling our story — they really nailed it. While the rest of the week was awesome, Casa Valentina was probably the high point of the week for me. 

Pinkfest ladies with the Casa Valentina cast.

After the show, we made our way to Mary’s Attic, a dance club upstairs from Hamburger Mary’s in Andersonville. They happened to be having a drag show that night and when they asked for a dollar boy (you know, the cute boy in tiny shorts that picks up the dollars that the queens drop on the floor) I jumped up with an enthusiastic me! Me! Me! The hostess was hesitant cuz I was in heels, but I assured her I was up for it. So, I relished in being the dollar girl, my first time being an official part of a drag show. That night I decided that I was gonna figure out how to do some amateur drag — I also learned that Mary’s Attic actually has an amateur night pretty regularly (on a future post I’ll share my progress in achieving this objective, along with unexpected twist). The club had a great party atmosphere and we got a lot of fun pics with Amanda, Brittany, Julie, Martha, Michelle, Robin, Sandy and Vivian — it was pouring rain outside, so we actually made up about a third of the crowd. 

The next morning, I woke up to a text from Sandy saying that she was gonna skip the daytime activities and get a little extra sleep — totally understandable. So, I got my Julie on and headed to the Thai restaurant by myself — meeting up with Ajay, Carrie, Michelle and Roxie. After lunch, Carrie and Ajay had some other business to take care of and Michelle had tickets to see a play a the Shakespeare Theater at Navy Pier. So, Roxie and I headed to the Driehaus Museum, where we were to meet up with Martha and Vivian. We got there early, so I suggested we do a little window shopping at some nearby Gold Coast boutique shops. The first one had tops in the $200 price range — yeah, just looking. At the second shop, a sales person opened the door for us. At this place, the clothes didn’t have prices tags — I guess if you have to ask, you can’t afford it. On the way out, the same guy opened the door for us and I figured out that that was his only job — definitely a unique experience for both of us. 

I had never been to the Driehaus before — actually never even heard of it before planning for Pinkfest. What a gem of a place — so glad we got tickets for the guided tour. Basically, it’s a turn of the century mansion that was recently restored and gives a glimpse into the Glided Age. I think it worked out better than the original plan, which was Expo Chicago — a massive Art Fair at Navy Pier. I had the weeks wrong and it was actually the week before Pinkfest, so I had to scramble to find the Driehaus as a replacement. I actually did go to Expo Chicago that week before, but due to scheduling I had to go in boy mode, so while just as interesting, a bit less fun. 

Saturday evening we had a group of 14 for a fancy Boystown restaurant called Wood. I was especially excited because my Chicago besties, Jessica and Claudia would be joining us. This place has great food at reasonable prices and it’s impossible to overdress. So, I was excited to wear one of my favorite Little Black Dresses — a sequined number that’s a bit too tight and short for a casual occasion. The after dinner plan was to see a burlesque show at Stage 773. On the walk over, a group of us got a picture with a crosswalk painted in the transgender colors. Unfortunately, the quality is not great, because Vivian and her great camera were at DSW — during dinner she realized that her platform heel had fallen apart and needed a quick shoe replacement. The burlesque show was awesome and we even got a Pinkfest shout out from the MC. The name of the burlesque company is Vaudezilla — remember that name, because it’ll be the subject of a future post. 

Pinkfest ladies with other colors.

After the show, Claudia, Sandy and I met up with Britney and Robin at Berlin. It was super crowded and we had an awesome time dancing until the wee hours. Back at my hotel room, Claudia began the process of deconstructing. I decided to give her a little privacy and after changing into my flats went by myself to the bar next door for a nightcap. Despite its proximity to Boystown, this crowd was distinctly cis-het. Eventually I got to talking with a couple of girls that also were just coming from Berlin — apparently birds of a feather. 

Having my last cigarette before heading back to the room, I was a bit ambivalent about deconstructing. On the one hand, it was such a great week and it seemed to go by much faster I expected, especially after months of planning. On the other hand, I was ready to go back to boy mode — the idea of not having to put makeup on in the morning was a welcome relief. I think this is a perfect example of my life — it’s all about balance, one could not exist without the other.

A bit of a postscript. Sunday morning my wife called and asked when I would be home. I said that I was almost packed, so I would be home in about 45 minutes. She was confused and asked, “Where are you?” It, then, dawned on me. Remember the “out of town trip” I had told my kids. Well, it seems she mistakenly believed the same story. So, she was like, “Wait, you’ve been out partying for the last three nights? You know you’re 50 years old?” So, I get home, the wife and I go out for a late breakfast and later that day the kids get back from grandmas house and I relish how much they missed me. Life is good.

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Tags: crossdressing, featured, Out & About, Pinkfest

Category: Out & About, Transgender Fun & Entertainment