Many years ago, I made friends with a GG co-worker. She and I became quite close friends. One day, while we were working on a project, she noticed I was wearing a sports bra (she could see it under my shirt). She asked me point blank "do you crossdress?". I figured, because she lived out of state and I would likely never see her again, after the project, I said "Yes, I do". After that we just went back to work. This was supposed to be a one week project, instead, it became a 6 month project. Because we were out of town on a business trip, every night we would have dinner together and just chat and have a drink or two (remember there is nothing like "that" between us, just good friends). Since that project we have both left that company, but we still email back and forth a couple of times a month. About a week ago we began playing phone tag, last night we actually talked. She told me that she was going to be in town for business for the next two months and she wanted to know if I wanted to meet up for dinner, drinks and a chat. My family is going out of state on vacation for around 10 days this month, I can't go due to work. I figured I would spend my free time dressed en femme. I said "sure, I'd love to, just let me know what works for you". She gave me a date and lo and behold... it falls right during my en femme time. I agreed. Then came the scary part: she said "Are you going to dress as a man or a woman?". I sort of blew it off and said "which ever you prefer". She then said "I would prefer you dress as a woman"... gulp. I asked her "are you joking" and she said "nope, I am dead serious" then she added "pick out a nice dress, and we'll go somewhere nice". At first I thought this was a dream come true... then it occured to me that she was serious. Now I have to plan out my outfit, make up, shoes (can't forget about shoes), hair... everything.
I think I'm starting to panic. In a good sort of way.
Originally Posted by Freddy12
