I was in Florida, on a break from my job and visiting friends. I was staying in a dive motel in Pensacola Beach and visiting different people each day. Each evening I would return to the hotel and then plan the next day's visit that evening. There wasn't much to do after that though and my mind started to wander.
I imagined myself going out and buying a few women's outfits while I was there. I had been dressing for many years now and even brought some panties and a bra with me on the trip. I always liked to dress when I travel, even making sure I have panties and a bra on when I drive on a weekend trip.
I felt brazen because no one knew me in this town and if I paid in cash, they wouldn't know my name. So what if I got a few weird stares, I would never see those people again. So the second day after visiting my friends who lived to the east, I drove back and stopped off at a K-Mart. I walked all through the store and couldn't bring up the courage to buy anything. I hopped back in my car and moved along.
The next store I stopped at was a super Wal-Mart. I wandered through the store and noticed they had self-checkout lines. That was the push I needed. I could scan and bag all the goods I was going to purchase. I still didn't have the courage to select items from the women's department, but I did pick out three things. It was Halloween time, so I picked up a barmaid's dress and a wig, then two t-shirts to put on either side and hide the fact that I was carrying a women's costume around.
I made my way to the checkout, got into a short line, and scanned and bagged my items as quick as possible. I got back to the hotel and immediately tried on the dress and wig. It felt smooth against my skin and I stayed dressed the rest of that evening.
The next day, after visiting my next group of friends to the west, I found another super Wal-Mart on the way home. This one was in a shady part of town, so there were no self-checkout lines. I wandered the women's wear and then headed to the Halloween section. There was a greater assortment of costumes, including some short dresses for adult women. One particularly caught my attention. It was a sexy maid's outfit. I went and picked out a pirate costume, then grabbed the maid's outfit and another little dress for a pixie and made my way to the checkout.
