January 22, 2008 - Detroit

I used to really like going to Detroit �cause I had a Tgirlfriend there that was a lot of fun to hang out with (Glenda). I wont go into her personal details, she can share that with you if she likes, but she has decided to stop crossdressing. I don�t want to make it harder on her so I have not been calling her when I go to Detroit. So with no one there to hang out with, Detroit is now somewhat boring for me. Oh well . . .
So my first night there I wore a new skirt I bought along with a top I bought probably a year ago but had never worn because I just couldn�t find the right skirt to go with it. That night I went to the movies and saw Cloverfield. Still can�t decide if I liked it or not. I love Godzilla type movies (no, it is NOT a Godzilla flick) but this one had what I call the �shaky camera� technique and I found it annoying as hell. It�s shot from the perspective of people living through the events and using their camcorder to record it.
After the movie I went to the �Olive Garden� for dinner. While sitting in the waiting area waiting for a table to come free, two of the hosts went out of their way to strike up conversations with me. It was pretty clear they were gay and that they knew I was a CD, so I thought the gesture was nice. When they took me back to the table he asked �is this OK, or would you prefer the corner?� It took me a moment to realize he was trying to give me the option of sitting in an out of the way place where I wouldn�t be noticed. I smiled and told him I wasn�t all that shy or picky and would take what ever table was available. The waitress was a doll and only hesitated a second when she figured out I was a guy. After that I was �dear�. LoL
As in �What would you like to drink dear?� and �is everything all right dear?�, etc, etc. I gave her a $15 tip on a $25 dinner to show her how much I appreciated it and to maybe smooth the way for the next TG that came in. Can you see them now?
�Hey that crossdresser tips pretty good � I want the next one that comes in!�
Well, I can hope that�s the way it will go down any way.
The next night I�m afraid to say did not go so well. I completely lost my confidence and have no idea why. I think I looked fine, at least as good as any other night where I felt on top of the world. It started off OK, even funny. I went to the book store and while I was paying for them the lady asked if I had one of their member cards. I said yes, but not with me. She said �That�s OK, I can look it up by your phone number if you like?�
�Sure�, says I, and I proceed to give her the phone number. Apparently our card is in my wife�s name because she looks it up and then asks �Are you <INSERT MY WIFE�S NAME HERE>?� Out of habit and with out thinking about it, I said �Nah, that�s my wife!� DOH! Talk about a Homer Simpson moment. We both laughed, I grabbed my books, and left. Next I went to Macy�s to do some shopping. I had been there maybe 5 minutes when for no reason at all my confidence just evaporated. POOF! One moment feeling pretty and confident, and the next feeling like a guy in a dress. I�ve long since realized that lack of confidence will destroy my ability to even think of passing and so I called it a night. I went back to the hotel and got cleaned up, went to dinner as Matt, and just made an absolute pig outta myself with Steak and Pasta. OK, most girls go for the chocolate when depressed � I�ll take Steak and Pasta thank you very much!