Went to visit the mother-in-law this past week. It is between 14 to 15 hours of driving one way. We used to make in a day, but since I am the only one that can drive, we make it a 2 day trip now.
A couple weeks ago, my wife suggested that since I want to be out in public while being dressed as a woman, why not dress on the way down and on the way back.
I wanted to blend in, so the wife and I both wore jeans and a t-shirt. She doesn't wear make-up and neither do I so I guess we could pass as girlfriends or maybe sisters. I also was wearing women's tennis shoes and a pocket bra with my forms and I was also wearing a wig.
i had no trouble getting out and putting gas in the car, or even helping my wife in and out of the car, but after the first day we stopped at our normal motel and I walked up to the door. I thought it was strange that there was no cars in the parking lot, but we stopped anyway. The door going into the lobby was locked, not sure why it was closed. Well, I spotted another motel across the highway. As we were driving up, I lost all nerve. I removed both my wig and breast forms (but left my bra on) to check into the motel. I am kind of glad I did, since there were a bunch of contruction workers there outside the motel and I know I wouldn't have felt as comfortable.
The next day I got up and only wore my jeans, t-shirt, and women's tennis shoes for the second day of traveling down to the mother-in-law's city. My wife never said anything or even ask any questions about the way I was dressed.
On the way back the first day I did wear a bra with my breast forms, but again I pulled out the forms before checking into the motel. Not sure why I lost my nerve since I was looking forward to being dressed out in public. But all my clothing I was wearing were women's clothing. Something is better than nothing.
The second day on our way back I only was wearing my women's clothes with my breast forms again. After a couple of hours of driving, my wife asked why I wasn't wearing my wig, and I told her I was disappointed in myself and just wasn't in the mood. Well she said we still had most of the day, and I could wear it and go into a gas station. I put on my wig and continued driving and at the next stop, the wife and I walked into the gas station together to get something to drink. The clerk said "Hello Ladies". Not sure if she made me and was trying to make me feel good about myself or if I actually fooled her. When we left the clerk said "Thanks ladies". The little town we stopped in is in the middle of Kansas. No big city, maybe a population of 2,000 people. There were no problems and I did very little talking, but the clerk had to know I was a guy dressed as a woman.
This trip has given me a little confidence, and maybe it might lead me to head out more while being dressed.