On going out

It's been a while since I've written. So much going on, and there never seems to be any time to update.

My fiancee and I rarely get a chance to talk about dressing these days, partially because we're so busy, and partially because I haven't had the courage to talk to her about what's on my mind. Maybe she will find my thoughts here before I can muster up that courage.

The issue of me going out dressed has been brought up before, on and off, for a while now. On one occasion she came back from a trip she'd taken and when she came back a little early, heard the clicking of heels on the pavement around the corner from our home. She thought it might have been me, dressed and walking around the neighborhood, assuming I still had time before she got back. Well it wasn't me. In fact, I was at home playing video games (I think). On another occasion, I asked her about my going out, and she answered to the effect that I might as well, since I do what I want anyway. I thought that was pretty uncool, especially since I have been trying very hard to be open and honest with her. Anyway, I have been under the impression that she assumes I've been going out dressed all along. What she doesn't know is how much anxiety is involved with going out dressed as a woman, not only when you aren't born one, but when you are taller than most men.

I have been out twice dressed during the daytime. And it was exhilarating.

Once I get around to telling her about it, I'm hoping to have a conversation about me going out dressed with my sister (biological). She's dying to go out shopping with me dressed!

I will write the details of my first time going out dressed in another blog to follow, just to keep this post manageable. I'd like to talk about the things I've noticed so far about going out dressed. Hopefully this may help a few girls out there. I am in no way an expert, but there's a few things that I've read about that seem to help with going out. Thought I'd share about my experiences so far.

First thing I learned, before even considering going out dressed, is safety first. I have brought with me (both times out dressed) an emergency bag. Just in case a quick change is required, I packed a duffel with a pair of pants, tshirt, flip-flops, and a bag of makeup removing cloths. This not only takes little or no extra effort, it's also a kind of security blanket. Next time I may put the bag in my car ahead of time, so that I don't have to lug it around while fumbling with the purse and keys. Also plan where to go, and how to get back. I live in the East Bay, and know of certain places I should stay away from while dressed. Living in a densely populated area, I also plan how to get back (where to park, which route to walk from where I park)

Second thing I learned is that less makeup is better than too much. While I was driving around, I looked in the rear view mirror to both check and admire how I'd done my eyes. When I got to the first place I would be walking around, I felt like only women in catalogs and makeup commercials wore makeup like that. I had club makeup on! Second time out, I still overdid the eyeliner a bit, but everything else was toned down a bit. I felt a little less self conscious. Most women seem to use makeup sparingly, to smooth and even out the skin, and highlight, not create features.

Third thing I have learned is that whether people knew I was a guy or not, people for the most part were too busy doing what they were doing to recognize me. Even though I might have been over 6' tall in a dress and heels standing next to them. As a guy, I'm always observing people already, and when dressed I found myself looking around a little less, but not hiding or averting my eyes from anyone. Sales people, security guards, other shoppers, etc. have all smiled at me when I smiled at them first. Of course I'm not saying to go out carefree and not be aware of the surroundings, but after the planning and execution had been done, I naturally began to relax and enjoy what I was doing.

Will write more about the subject later, for now I'm going out for a walk!