Prior to a little over five years ago, before I started going out regularly, I thought about the things I could do if I ever decided to go out dressed. My biggest goals at the time were to get a makeover, buy some clothes, maybe do some traveling, and join a local crossdresser support group. I had lots of plans/dreams.
But never would I believe the girl me would make friends. It just wasn’t on the radar screen.
I’ve always thought my life has been a series of fortunate accidents. In high school, my mom suggested I might like debate, so I signed up, and the three years I debated have served me well throughout my life. When time for college arrived, mom said I was good at math, so maybe become an accountant? Once again, she was right.
In my later 20’s, I decided to take time off to travel. Saved money, then quit my job, and bought a Volkswagen campervan. Traveled throughout the US, visiting friends and seeing the sights. At home for Thanksgiving, see a travel article in the paper about New Zealand being the most beautiful country in the world (long before the Lord of the Rings movies were filmed). I tell myself, why not? Five months later, on day ten in New Zealand, an Aussie lass walks into the kitchen at the youth hostel where I was staying, and sits down to talk (I was the only one in the kitchen).
This April we’ll be married 30 years.
I’ve also been fortunate to be in the right place at the right time for my Dee side. When I started planning my first days out dressing, I chose Sephora for my makeover because I heard my wife tell her best friend how good the people at Sephora were (and they are great). I chose Nordstrom because a couple of months before my wife was shopping for a dress for a wedding (the daughter of the best friend); when she went to Dillard’s the staff was rude, but at Nordstrom they were welcoming.
Based on that “homework” I chose Sephora for my makeover and Nordstrom to try on dresses (both set up in advance). Julie at Sephora was great (and taught me what I needed to do my own makeup) and Falon at Nordstrom was beyond great. She helped me find my style and gave me emotional support, and introduced me to Karla. Five years on, I’m in contact with both of them, and Karla and I have a planned night out to see Hairspray once I return to the US (she referred to it as a dream date).
Meeting Michelle was another fortunate accident. I was taking a four day Dee train trip to Chicago and I needed to have my nails done. My preferred nail tech wasn’t available, so I ended up with Michelle. She was almost giddy I was a crossdresser, and we hit it off. Five years on, we text regularly and get together when it works for the both of us.
I’ve been to Michelle’s (and Dee’s) favorite bar, Hemingway’s, multiple times over the last three years. Kim, the co-owner, almost dragged me back in the last time I was there (I was looking to meet Michelle and she was at a bar slightly down the block).
Cassidi, one of the bartenders, made it a point to come talk to me and say that she admired me. Although I’ve only seen her in casual cute, she swears she likes to get dressed up (and showed me a few photos on her phone to prove it), and said she’d love to go “out on the town” one night. I’ve also met Michelle’s friends Christy and Pinar at Hemingway’s and now I’m Facebook friends with them (of course, Facebook is the guy me).
One other friend, Renee, predates my days of going out, and is another example of a fortunate accident. We met in a time long ago when she put a personal ad in a local free paper, and I responded. Turns out, she had a roommate who was a crossdresser, so when I hinted around about dressing, she called my bluff and bought me my first pair of heels and helped me dress a couple of times.
Thirty-some years later, we reconnected on Facebook, and for some reason, she enjoys seeing me dressed, and enjoys my scribbles here (and usually comments on my scribbles). We text regularly, and she provides feedback, support, and encouragement.
Getting out dressed is fun for me. Going out dressed and seeing friends I have made takes it to another level, and I cherish those times.
Editorial comment: If you don’t believe you can do this, you are wrong. Look what Dee has been able to do, the friends she has made. I have done the same thing, as have other contributors. This is an important post!