If you and new to all of this cross dressing, perhaps you have spent a ton of time thinking about those questions already. If not, here are a few hard fought lessons I learned, mostly at the expense of my feet.
Way "back in the day" during my first real Halloween in drag, essentially I learned three things. Mainly, those three or four inch heels I picked out were simply not built for any sort of comfort (for me) and very quickly I was in agony. I also learned the demarcation point in doing a "ha-ha" drag impersonation and being way more serious is shaving your legs. I did shave mine and heard about it for weeks from my cis woman friends. And finally, getting the compliment "you have great legs" does not mean you are one of the rare few men who are naturals at making the external transformation into women. You may have the great legs as many men actually do, but it's what above them that often counts with your broad shoulders.
Regardless of all the warnings, I found Halloween to be a great time to get out and "strut my stuff" at the time in my life I couldn't. Plus I could live vicariously through a couple very effeminate servers on my staff at a couple restaurants I ran. One in particular was cross dressed by his girl friend and looked so convincing, many of my regulars asked when the new female server started. I was more than a tad envious as I was dressed in my old Army uniform.
On the other hand, Halloween was similar to a huge wad of cotton candy to me. After the evening was over, I couldn't figure out how I was going to make it another year until another "fix." How I began to get around all of that is a story for another blog post but essentially marked the point when I began to test my feminine presence in the world.
Over the remainder of October I'm going to try to pass along a few of my Halloween stories. Some scary, some fun and some flat out exciting.