Making plans

I have been talking with my wife and there are several trips that we both will be taking separately. Many of these trips will also be without our daughter. So I will have several days by myself to dress however I'd like for as long as I like. I'm kind of excited about it. The trips are a few months off and so I think I'll have some time to get some new items. Here's my wish list in no apparent order.

• Dress AND/OR pants with a top.
• Shoes - heels preferably, but maybe just a kitten heel. I'm already 6 feet tall, I don't need to be Amazonian.
• Nail supplies - emory board, color or French manicure, polish remover.
  
• Make-up - foundation, blush, lip stick/gloss plus liner, eye liner and shadow.
  
• Night-gown or other sleeping clothes.
• wig

I don't think I'll be able to pull off getting all of this stuff. There's a trip at the end of July that they will be taking for a full week and so I might be able to get this stuff by then. But most of those bullet points will cost about $50 each. $300 is some serious cake. Especially considering it's for secret use.

Essentially, I am beginning to think about going out in public. In the one time I dressed up as much as I can, it was a lot of fun, particularly walking in front of the open windows. I've got the body for it and felt very feminine while walking around. Quite a little rush. The other good thing is that in a flowy dress, the difficulties I have with tucking are not so apparent. So, I think that with some practice I could get the make-up looking pretty good. Get an attractive, but not too flashy, outfit (pants/jeans and a basic top). Slap on a wig and go for a walk about. I think I have a decent sense whether or not I'd pass or not. On Crossdressers.com it's easy to see that there are some tell-tell signs of a dude. But there are also some amazing transformations. Guys that definitely pass as a woman. And as I've been noticing people more, I look for the more masculine looking women and try to pin-point what it is about them that makes them still look like a woman. I can look at these people and see them as a guy, but there is still something that makes them feminine. But I think this might be a trick my brain is playing on me.

At any rate, based on how well I think I could pass, I'll decide where I'd like to try it out. If I pass great, then I'll go out during the day for sure. To the mall or grocery store. Might even go out to eat. If I barely pass, then most that will happen is that I might walk down the side walk at the outdoor shopping center at dusk or night. Or go get some gas in the car. Little anonymous trips like that.

There are many times that women look more manly. One is when they are working out. Extreme endurance athletes look very manly when they are exercising. So I've also thought about buying some workout clothes and going for a run. I've also thought about working out in the hotel weight room. The good part about workingout would be that I could probably get by with wearing a hat and buying just a pony-tail wig that would stick out the back. This could also work to hide my face a bit. the problem I see with this is that my veins BULGE when I workout or go for a run. I've definitely never seen a woman with veins like mine. Manly for sure.

It's definitely fun to think about.