The LGBQT community here has been a great support for me as I question who I am and what it is I want out of my life. I thought that I knew long ago but for unexplained reasons I now know less than ever. I have more questions to answer but today I have more confidence to live out my dream.
When I get dressed up at home I usually wear what I consider sexy outfits. I never gave it much thought as to why, it was just what I would do to make myself happy. That said I don’t always stomp around the house in stiletto heels but when I really need to feel more feminine I do. Most times I just wear something more comfortable like leggings or shorts and a simple top, flat shoes or sandals. But my dream is to go out into the world in the outfits that I find to be the most feminine. This of course would have to include sexy undergarments including garters and thigh-high stockings. A short skirt or dress, stretchy-tight top and heels or platform shoes. Jewelry, perfume, makeup would all be required to be the best I can be. The object in this dream of mine is to pass and not look like an ugly man dressed as a woman. This is an all out proposition which makes it nearly impossible for a first-timer to pull off. And this is why I have never been out in public dressed this way. My desire to do so is always in the forefront of my mind. There have been times when I am dressed up and get into the car and begin to drive down the driveway before I chicken out. The thought of toning it down never occurred to me until I had a few chats with others in the community. The advice was excellent; wear something more androgynous at first. Maybe a little lip gloss but nothing too extreme. This made me think I can do it.
My first trip outside the house was wearing an unpadded bra and thong panties under my usual tee shirt and shorts. No one could really tell of course, except maybe for the small bumps on my chest. Still, the experience was unnerving at first. I imagined all the worst things that could happen, which were that I’d see someone I know and they might get a hint of something different. So what? Now I am getting somewhere. So now just about every time I go out I’ll wear something under my clothes. Then one day I decided to paint my toes with a very light pink frost nail polish. I wore flat sandals and anyone who cared to look close enough might notice that I had my nails painted. That felt daring so I did it again and each time I felt exhilaration.
Now after a few weeks of becoming more and more daring I made a giant leap forward. I primped for hours, shaving smooth most of my body. At first I wasn’t sure exactly what I was going to do but after trying on a few tops I decided that I would try to wear a tight-fitting top and bra that show a little cleavage. That looked pretty convincing and that gave me the courage to keep going. At first I had planned to wear a pair of capri length pants and sandals but as I tried on a few other options I got brave and thought it was time to show my legs too. My skin was darkly tanned and freshly shaved and after moisturizing my skin my legs looked pretty good. I couldn’t muster the nerve to wear a skirt, even though I wanted to so badly. Even longer skirts were too much for me to handle emotionally and what was the point if I wanted to show my legs? So it came down to a pair of short denim shorts. Just as reviling as a short skirt, maybe even more so but they are shorts, so I thought I could handle wearing them. There was never a moment that I considered wearing heels though. Much like wearing a skirt, heels would be way too much for my first time out so I just wore a pair of plain, flat sandals. After an inspection in the full-length mirror I decided that was it. I wore a thin, leather strap choker that has a small pendant hanging from it, two bracelets and a couple of rings all of which felt just right. Then came the hard part. Makeup. I really can’t get it right and doubt I could ever pass unless I get much better at it. But since I was going out on a sunny warm day I came up with a pair of big sunglasses and a wide brimmed hat. Shiny lip gloss and a little foundation and blush was something I could handle. For once in my life I went right out the door without too much stress or doubt. OK, so I did hesitate for a few minutes but I told myself that if I got too nervous I would just turn around and come home. The final look in the mirror gave me enough confidence to finally do it.
The plan all along was to go out to this outdoor restaurant that is a couple of towns away from my home. There would be an outside chance that someone I knew could be there but it was a slim chance. The good thing about that place is that it has an entry right from the parking lot. All I had to do was get out of my car and walk a few paces to the gate and go find a table to sit at. Sounds easy, right? Well I sat in the car for a long while. Debating, torturing myself with my thoughts. Waiting for the way to clear. No one coming or going. Waiting until the servers were busy or inside the building. It felt like I was jumping out of a plane except I was doing it without a para shoot. This was the last part of the gauntlet, or so I thought. Once I stepped out of the car I had to keep going. It would be really weird if I got out and then quickly turned around and got back into my car. I was so nervous that I began to feel sweat and I didn’t want that so I opened the door and climbed out.
I began to walk towards the gate where the entrance to the restaurant and patio dining area. Walk isn’t really the right word for it because I felt like I was gliding or maybe floating and at a very fast pace. Everything around me felt surreal. My head was swishing around like I was drunk but I was feeling everything. The sun on my skin, a warm breeze on my smooth legs. The closer I got the more empowered I felt. I thought “I am doing this!” It felt so good at the same time that it was terrifying. What a crazy mix of emotions. Then once I was inside the gate I felt the hammer come down. It wasn’t very crowded there but the few customer that were sitting out on the patio were all looking at me. I know people always do that when someone enters a room or a space but this made me self conscious. I panicked, thinking that they were looking at me because they knew my secret. Maybe they are hateful people who would hate me just because I’m different. I didn’t know how any of them felt but I was totally and completely uncomfortable. The crazy part is that having people see me as a woman is what I have always wanted. This was the moment I have been waiting for but now that it was happening I lost my nerve. My legs went weak and my body felt like it was going to collapse. I think I even had tunnel vision, it was all too much to take in so I quickly found the closest table and sat down.
Thankfully I didn’t wait very long for one of the servers to come and ask me if I wanted a drink. She was an adorable young girl in khaki shorts and a green tee shirt with the restaurant name and logo on it. She called me sweetie which was very nice and that seemed to calm my nerves quite a bit. I ordered a fruit drink with a double shot of rum. She smiled and said she would be right back. Very typical and normal situation so far and I tried to concentrate on that. I crossed my right leg over my left thigh and looked all the way down my legs at my painted toenail and sandals. Now that was not normal for me. My legs were smooth, tanned and had a silky sheen from the lotion I had rubbed into my skin. Also there was a lot more of them showing underneath my very short, shorts. I liked the way they looked and tried to reassure myself that others would see me that way too. Most of the other diners had returned their stares to whatever they were doing before I got there but a couple of others kept turning to sneak a few extra looks my way. That was unnerving and I tried but couldn’t muster a smile. I was hoping I looked calm but inside I was still a bundle of nerves.