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I was really in the mood for trying some chilly fall outfits but "unfortunately" we were having some gorgeous upper 70's weather. I tried on a few outfits and decided a pair of skinny jeans, riding boots, and a thin, long sleeved top was the best outfit for the day. I considered going out but was very apprehensive about leaving the house with makeup on in daylight. I've done it before it's a little nerve wracking. I procrastinated and played around with some other looks until it was dark and then decided I would regret it if I didn't go out, and since it was dark, it was less intimidating. 


I got in the car and drove out of the garage. I wasn't even sure where I was going but it was a thrill to be out of the house. I drove to the next town and stopped at a thrift store. I went right in and started browsing. There were a handful of people there but no one seemed to pay any attention to me. I wasn't shopping for anything particular but was hoping to find some short booties to wear with skinny jeans. I really wanted to get a photo to "document" the trip so I tried taking selfies in a couple of mirrors but that was harder than I expected. I didn't find anything I liked but I didnt want to go home so I decided I would go to a nearby Ross store. In the parking lot was a group of guys practicing skate-board tricks. I walked past them to my car but couldn't find my keys buried in my purse. I realized that women must always have it on their mind to have the keys ready when walking across a parking lot at night. That was lesson #1.


At Ross, I put the keys in the front pocket of my jeans so that I would be able to locate them easily. I try to pick stores that are frequented mostly by women since they are less likely to be irritated by seeing a man dressed as a woman out shopping but this Ross store was 4-1 men to women! Luckily, it wasn't crowed so I headed over to the shoe area. There was only one woman there and I browsed as well. When she left I found a spot to prop the camera and took a few pictures with the timer function. Lesson #2: when doing this, turn the sound off on the camera! I had it set to count down and then take 5 photos. Again, I was lucky and the 5th pictures shot off and the beeping stopped just before a lady approached. After browsing the dresses I decided to try Kohls down the way. 


As I left the store I heard a car alarm going off in the parking lot and could see that it was my car that was going off! I hurried over and there seemed to be no issue with the car so I assumed that I must have triggered the "panic" button on the key-chain by accident. Lesson #3: Don't put the keys in the pocket of tight jeans.


I parked at Kohls and put the keys inside the pocket within the purse. When I got to the front doors I could see that inside the store a woman and 4 or 5 young ladies holding binders were approaching the doors as well. Apparently they were new-hires and she was showing them the store. I entered and looked at them and smiled. One or two glanced at me but they seemed to be on their best behavior and kept their attention on what the manager was telling them. Inside the store I tried again to take some selfies and found a shelf to place my camera to take photos...with the sound shut off. As I was walking through the jewelry area a woman riding an electric shopping cart almost cut out in front of me. I jumped out of the way and she apologized. I kind of nodded and kept walking but realized that I probably appeared rude. Lesson #4: Be engaging. I realized that a woman would have stopped and said "Oh, no. It was my fault. You are fine."


I didn't buy anything in any of the stores but it was a great experience out on my own. I learned a lot of little things but most of all was to just do it. I spent too much time procrastinating and was so glad once I got out the door!


Shopping Lessons


This year my schedule had me working almost the entire length of the kids' fall break so my wife decided to take them out of town herself. That did leave me with a few hours here and there to fill in. The lawn needs to be mowed. The garden needs to be cleaned out.The dog could use a good walk. But like any self respecting cross dresser, I put off those things and put on my makeup. 

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