August 1, 2011:

My first time in public, like actual regular straight daytime public

Ok, I don't want to say too much about this day since it was actually
a really big day for a good friend of mine and I'm just piggy-backing
off of her.  This was the day that her workplace officially announced
to everyone that she was transitioning to a woman.  To celebrate and
as a show of support, a bunch of friends and her coworkers took her
out to happy hour.  This was at a restaurant next to the mall not far
from where she works.  Congrats, sis.  We're all so proud of you.

As for me, this marks my first time out as Madeline in a completely
straight place in broad daylight.  I know last year I was Madeline at a
casino in Las Vegas one night with one of my best friends, but this
was different.  A) This was during the day so I was in plain sight of
everyone.  B)  This was a totally normal, everyday place.  Not a gay
bar, not the gay part of town, not a casino where all sorts of people
come out, not a diner late at night where not many people are out.  
This was a place filled with straight people and families and all types
of ordinary people who may have never knowingly seen a trans
person in their life.  C)  This was in my neighborhood.  This is a mall
I frequent in boy mode.  I know several people who live and shop in
this area who don't know about Madeline.

But I'm probably making too much of this experience just as I built it
up too much in my mind beforehand.  The scariest part was walking
from my car, across the parking lot, and into the bar area of the
restaurant.  That jaunt took approximately a minute and a half and
while many people saw me, I'm not sure if anyone read me.  They
may have but I don't care.  Of course it didn't help that I broke a
heel on my left shoe mid walk.  But I continued unabated and was
soon in the safety of the rest of the happy hour group.  The rest of
the evening went well.  We all congratulated our friend and I caught
up with one of my dearest friends, Jayme, whom I hadn't seen in
months.  Love ya, Jayme.  

Oh, I guess I should tell you what I wore.  I tried to dress down but I
couldn't resist upping the hotness factor at least a little.  So instead
of a top and jeans (as I originally planned), I went with a silk short
sleeve blouse and black pencil skirt.  I was debating heels or no heels
for a while.  I should have gone with flats but they just didn't look
right with this outfit selection so, not surprisingly, I went with heels.  
See pics here.

I also toned down the makeup.  No color over my eyes, very light
makeup on my cheeks, and only gloss on my lips.  I have to admit
that I am only a small fraction as passable without the assistance of
lots of makeup but I think that too will come with practice.  I feel
I've finally got the going-out-for-the-night makeup skills down.  Now
I need to work on my casual-daytime-regular-crowd makeup.

So in summary, it was a great experience.  It was really not as big a
deal as I always imagined and I can't wait to do it again.  The next big
milestone on my bucket list (no I'm not dying) is to go shopping as
Madeline.  I think this will likely happen sooner rather than later.  
When it does, I'll be sure to write about it here.  Bye for now.  :)
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