|July 30, 2010:
My very first date (see pics here)
This is the day that I finally felt like a real woman. Short of getting
some type of surgery, this is most likely as close to becoming a real
woman as I'm ever going to get. I finally decided to take a chance
and go out on my first date as Madeline with a gentleman suitor. The
gentleman in question is Rob who I met at the Laptop Lounge two
I started off by getting dressed after work. I spent way too much
time primping and trying on various outfits. It was a fine line I was
walking. On the one hand, I wanted to look as attractive as possible.
On the other hand, I needed to be somewhat understated as I knew
we would be going to dinner and a movie in a completely straight
setting and I didn't want to dress too provocatively and draw undue
attention on myself. You can see the outfit I finally chose in my
picture gallery. I admit it wasn't close to the best I've ever looked.
In fact, I kinda really disliked how I looked. But I was running late
so it would have to do.
I got a little lost on my way to Rob's place but when I finally arrived,
I was nearly shaking due to my nerves. I could barely speak above a
whisper and had trouble maintaining my girl voice. But Rob
reassured me that I looked and sounded great and pretty soon we
We first when to a quaint little Thai restaurant. Luckily, the place
was nearly empty. That's no reflection on the quality of the food
there. My shrimp Pad Thai was quite yummers. I'm sure our
waitress read me right away but she gave no indication to the effect.
Rob was a great conversationalist and we had a nice talk over dinner.
That really helped calm my nerves. Soon, dinner was over and it was
off to the movie theatre.
Again, I was fortunate that there weren't many people out. We did
have to wait in line behind a bunch of teenagers to get tickets and I
was so so scared that they would see me and say or do something. I
tried to stay out of view as much as possible. But I was all worried
about nothing. They never even glanced my way. Again, I'm sure
the ticket lady and the concession stand lady were able to read me
right away but they didn't say anything. I was relieved.
Finally in the safety of the dark theatre, Rob and I watched the
movie Salt. It was good mindless entertainment. The movie is fun as
long as you can easily suspend your disbelief. Plus, it's always
enjoyable to see the gorgeous Angelina Jolie on the big screen.
After the movie, I went back to Rob's place for a glass of wine and
some more nice conversation. Without getting into any sordid
details, Rob and I got a little frisky as the evening went on, and
that's all I'll say about that. After all, a lady doesn't talk about such
things in public.
So that was what happened on my very first date as Madeline.
Completely scary experience since it was only my second time en
femme in a totally straight setting (see details of my Vegas trip to
read about my first time). But everything went great. And I
especially have to thank Rob for such a great first date. Rob, you
were sweet, caring, interesting, funny, and a complete gentleman.
I know over the years many of you have tried to ask me out on a
date. Now that I've finally taken the plunge, does that mean the
flood gates will be opened and I'll be going out on many more dates?
Probably not. I'm still very iffy about meeting people that I just talk
to on the Internet. I just don't know anything about you to trust you
enough to go out on a date. But if we meet first in a safe setting, say
at a TG party somewhere, your chances will greatly improve.
I must also add the caveat that I'm still not sure about Madeline
sexual orientation. I know I definitely like genetic girls and very
passable T-girls. While I really enjoyed my extra-curricular activities
with Rob, I feel the jury's still out on where men fall on my list of
sexual preferences. Maybe after a few more dates, I'll know more
but for now, let's just see where this crazy ride called life takes me.