I have lately come to terms that I like to cross dress and want to explore it more. Thanks to one of my friends on here who has encouraged me I am taking that next step. I have never really told anybody else about what I do. I had to go out of town for a few days on business and decided to take my clothes so I could dress and go out in public some. I figured I would do it there so in case I didn't pass well it would be in another town.
Well yesterday I got through calling on one customer and had some time to kill before a 4:00 appointment with another customer. I decided to swing by a mall on the way to look for a new skirt. As I began shopping another customer called with a problem. Which was ok because I have often acted like I was on the phone when I go out looking at clothes so salesperson will not bother me. Well I was on the phone for about 15 minutes in a pretty intense conversation while trying to look at clothes. As soon as I hung up out of no where a sales women appeared out of no where and I asked if I need help. With out really thinking because I was frustrated from the call I said I was looking for a new skirt for summer. She paused a minute an replied Well what size are you looking for? I then realized what I had said. I thought for a second wondering should I back track my answer or just go with it. I decided to just go with it. She started quizzing me on if I wanted casual or more dressy, heels or no heels etc. After a few minutes I asked her if she had ever waited on a guy shopping for himself a skirt. She said it was a first but it did not bother her at all. She inquired how long I had been doing this and did I go out often. I told her I had been dressing on and off for the last ten years but was taking it more serious now. We had picked out several skirts and other things to try on. I realized I needed to get going if I was going to make my appointment. I asked her if she was going to be around for a few more hours and I would come back. She said she was there until close. She suggested that if I could come back dressed that she would love to see it and that it would make it less awkward to use the womens dressing rooms. I said I would have to think about that.
I got to my meeting on time but could hardly pay attention thinking about going back dressed. The meeting got over and by then I had decided I was going to go back to the hotel and get dressed and go back to the store. I got back and showered and shaved what need to be shaved. I took my time with my makeup and nails wanting to make sure everything was just right. The whole time I was so nervous my heart was just racing. I was shaking as I walked out of my room and to the elevator and to the lobby. I realized I should have parked out back of the hotel instead of the front so I wouldn't have to go through the lobby. As the elevator opened in the lobby I took a deep breath and started to walk out and about got run over by a guy getting on the elevator. He bumped into me and said excuse me Mam. I just smiled at him and kept going.
Driving to the mall I was scared to death I would have wreck and have to explain that to the police. I got to the mall and parked where I had earlier. As I got close to the door I realized the womens department was on the other side. I took another deep breath and kept going. Once in the sound of my heels on the hard floor sounded so loud to me I thought everybody would be looking at who was making all the noise. I was over reacting just a little. I made my way to the womens area and looked for my new friend Pam. She was helping another lady at the time so I just browsed looking at clothes thinking I wish this other lady would hurry up and leave. In a few minutes the other lady went to try something on so I approached Pam. She asked if she could help me and I thought she has no clue. I told her it was me and I took her advice and came back dressed and would like to try on the items we had picked earlier. She kept saying she was amazed at how I looked. She got the clothes and took them to a dressing room for me. By this time the other lady came out and left thank goodness. I tried on clothes for a while and it was a blast. As it came time for the store to close I did buy a new skirt and blouse. Pam said we should go get some drinks that she would love to know more about me. I said sure. She told me where she was parked to pull my car over by her and I could just follow her.
We went to local bar and grill place. As we were going in I told her I was nervous about ordering she said she would place our drink order with the waiter. I just smiled a lot when the waiter/waitress came around. She asked me how long I had been doing this, how often do I go out. I told her this was the first real time out and how much I appreciated her understanding and helping me. She said she was a very open minded person and by working in retail for as long she had knew of a lot of coworkers who were gay and it did not phase her. I told her I was not sure what I was because I had never been with a man. She apologized for making the assumption I was gay. By this point with a few drinks in I was pretty much telling her everything. I told her how I thought about it a lot and had decided to explore it and I wanted to experience a man. She made a joke about how they are after just one thing. She asked how I was going to do that. I told her I was really not sure but thought about putting an ad on Craiglist for the next night. She warned against that saying I could end up dead. We talked a long time. Finally it was time to go. She said she had to be a work earlier tomorrow. She told me I should get dressed and come back by. I told her I had meetings all day but I was going to dress afterwork and go out somewhere with my new found confidence. She offered to go with me if I wanted I said absolutely. She asked what I wanted. I told her we could just grab some dinner or movie and then some drinks.
As I type this this I am getting ready for her to pick me up and go out and hit the town. LOL
Posted by KellyCost 10 months ago Views: