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
100% (20/0)
Categories: First TimeShemales
Posted by KellyCost
10 months ago    Views: 2,219
Comments (12)
Reply for:
Reply text
Please login or register to post comments.
8 months ago
so awesome!!!
10 months ago
so now your really going to have lots of fun you need to write more about
10 months ago
fantastic courage. and I can see why Pam was surprised when you returned ... you do look very passable. id love to trade a few messages about your curiosity xx
10 months ago
I can only imagine! ;)
10 months ago
This was definitely a real experience. At times it felt unreal.
10 months ago
Good luck with your journey. I have been going through this for several years. My experience last week made it all worth it. As I found out you just have to jump out there and do it. What's the worst that will happen. Wish I had done it a lot sooner.
10 months ago
Love your story....I am at the same point in my exploration of the female side and can really relate to your experience. Thanks for sharing and anxious to read the next installment!
10 months ago
If this is a real experience, I hope it all goes well. Good luck, Hon! Hugs, Jenna
10 months ago
loving it more plizzz
10 months ago
great story.....I hope you tell us what happened the next night
10 months ago
o my goddess you are living my fantasy! GO GURL!!! Please let us know how the second night went!~Bri
10 months ago
I like your story. Did it really happen? I hope so, wish you more, happy adventures, Kelly:)