Well, I'll probably bore folks and hit some nerves, but as I am opening my female side, I'm finding I want to open myself up in more ways, so here is my story of where I am and how I got here.
I'm older, 61 but don't usually get pegged for that. I'm married and have a wonderful marriage, but haven't reviewed this side to my wife yet as she wouldn't understand based on conversations about other family members who have turned out Trans. For now I keep this dressing and being Roxie to my business trips. It was on a long business trip last month that I actually started dressing all the way.
So I am fairly new to this and learning more about myself as I go through this. I really don't know what possessed me to suddenly jump into dressing. The urges have been there all my life, I'll get to that shortly, but it really was out of the blue I bought a skirt top, and bra and jumped onto dressing.
When I was born, my older sister wanted a sister and gave me a girls name the first day I was in this world. My folks thought this was cute and repeated the story all my life. When I was still a toddler my sister would dress me in a skirt, blouse and Shirly Temple wig to play with her. Again my folks thought it was cute. I can remember even through elementary school, being given my sister's hand me downs to wear, mainly her pajamas. I'm beginning to see a trend here.
In junior high my mom took over a dress shop/beauty shop in town. We helped around and I got to check out the girls clothes all the time. I even began wondering about wearing them then. I did get the opportunity to sneak in some when I was at the store alone going as far as putting on the maniquene's wig while wearing clothes. My Dad was beginning to wonder about me and had joked that when I came on the football field in High School it would be leading the band not playing. I ended up playing football and was quite good as a defensive tackle despite my smaller size, was starting at 5'11" and 185 lbs.
It was during this time I got my first shot at dressing all the way. We had a fundraiser for the athletics booster club that the whole football team was "encouraged " to participate in. They held a womanless beauty revues. I got a nice gown from my moms shop, an awful looking wig and was made up to look like a hooked, but it was my first time. It was both fun, and awful. Because the event was looked as a joke it just didn't feel right.
I never did anything for years after that other than the occasional wearing of panties. For some reason the last year or so, the thought of dressing has run through my mind but nothing came of it until a month ago.
I was on a business trip, and my bag was delayed and had to be delivered to my hotel the day after I flew in. As I was working that evening and had tot go in before my bag arrived, I went to pick up a few things at Walmart. For some reason while I did thT I grabbed panties, a bra, top and skirt. I was finally starting down a path that opened up a whole new side of me.
I eventually bought a wig and breast forms, and some dresses and shoes and a clutch. I was enjoying dressing up in my hotel room that week. I was home for a week then back for a couple more weeks and added makeup and nails to the collection. I was letting dressing and being Roxie take some of the stress of working so much off. I was loving being Roxie. My first trip out was a quick run to Walmart to pick up a few things. I went out a couple of times just driving around and was petrified of meting discovered.
My last night of the trip I was determined to enjoy. I dressed real casual, I had a khaki cargo pocket skirt that hit just above k eyes on with an aqua men's fishing shirt with panties, bra, thigh high stockings,, and wig and makeup with gel nails on. It was a good look and I toned down the makeup and went with more neutral colors. I went for an early dinner at my favorite steakhouse there. The wait staff and manager had remembered me when I was there so much as a man that I was afraid they would make me, but they didn't act like it. The waiter called me hin and treated me very politely. After dinner I went into the mall and went I to 3 different women's stores just doing some window shopping. I was in heaven when I got back and Wes really dreading letting it all go to come back home. I can't wait for my next business trip to be able to dress again and be Roxie again.