My Weekend

By Sherry Greer, our Miss America!

(And I add parenthetically, a few weeks back.)

My wife loves to gamble and goes out of town periodically with her two friends to do so. A few weeks prior I was looking on the internet to find something to do and noticed a local artist, Michael Sherry, was having an art show at a restaurant/hotel in downtown Cleveland. When I saw his last name I just had to go! The place is called The 9 and I have been there before (in both modes) so I knew it was good. Kandi also had the very first Supper Club there. I asked Kandi and Annie if they wanted to go.

I made reservations for 6:15 for dinner and we would meet a little earlier to view the artwork. Kandi said she would meet us there. A few weeks earlier I told Annie I wanted to do her makeup so today was the day! I mostly got ready but still had my eyes to do when she arrived. Annie came to my house about 2:00. We first had a drink and then we went to the bathroom and got started. I sent Annie a few still pictures from a few videos I watched and she picked her favorite. I tried my best to duplicate the look. It’s really hard to do someone else’s makeup and it’s only the second time I’ve done it, I actually did my wife’s before! It was wonderful to be surrounded by femininity.

The two of us talked about what I was doing and how excited we were to go out. Annie brought a couple outfits and we picked out the best one. I like matching eye makeup to my outfit so I tried to use the same or similar colors for her eyeshadow. She said she learned a few tricks watching me so overall it was a success and she liked the look I created! I finished my eyes quickly as she did her hair. I asked her to pull my hair back into a loose ponytail and it looked beautiful. I couldn’t wait to wear my dress because I’ve been waiting for just the right occasion.

We drove together and it was wonderful talking about female issues with her. She’s definitely one I feel comfortable talking to and like my friend Heather I feel I can tell her anything. The temperature in Cleveland that night was in the high 20’s and felt quite cold on my bare legs. We valeted my car and it was a wonderful sound as I heard my 4″ stiletto heels click on the pavement. They really are very comfortable despite being that high! We arrived before Kandi and were viewing the artwork and having a complimentary glass of wine when we met up with her.

The event coordinator was nice enough to give us a tour of the artwork on another floor. After 30 minutes or so we went down for dinner. The food and company were tremendous and our waiter was extremely knowledgeable and nice and made our experience memorable. After dinner we went to the Vault which is downstairs and actually inside an old bank vault. There’s multiple private rooms plus the bar area. The entire area has a Speakeasy vibe. After one drink we called it a night. The entire night was amazing and the feminine feeling and spirit running through my body and the experiences that I am having as Sherry is something that continues to build into something I’ve never imagined. As I was driving home Annie and I reflected on the evening.

The next day my weekend continued! At the last Supper Club I told my friend Jessi that I would take her makeup shopping. Annie decided to join us after she got off of work. I left my house early and went shopping to a few stores around the Ulta we were going to. I bought a top at Rue 21 from the clearance rack for $3! I arrived at Ulta early and I of course was approached by a sales associate. I explained to her about Jessi that she is a mtf who is just starting to transition.

Jessi arrived and then Annie a few minutes after that. The SA was doing color matches for foundation and concealer and kept on asking me to get my opinion. I truly felt like the SA thought I was a woman. I know Jessi needs help and I am happy to help her and want her to build confidence in who she wants to be. After buying a few things in Ulta we went to Target to buy a few more products. It’s amazing that the more I help Jessi build confidence the more I build confidence! What an amazing two days! The picture with the purple top is from Sunday.

Stay beautiful-Sherry

I go back and look at pictures from our early outings and Sherry has blown past me in terms of her presentation and overall view of things. And that makes me happy!

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