Last Summers VacationI am a 56 years old, who has a wonderful wife that is supportive but careful about me cross-dressing. We call these outings. We have gone out together many times (shopping, dinner, sightseeing) mostly when out of town. I have cross dressed since my early teens. Last summer I had a opportunity of a life time. I needed to drive cross country by myself so I took the opportunity to make this a cross-dressing trip. My first day out I had my nails done and checked into a motel. The next morning I got up got dressed fully dressed (hip pads, breast form, wig, make up etc) in a tank top, skirt and blouse and head out on the road. The feeling of freedom was great. I stopped when I needed to (restroom, meals and gas) had no problems. That night I checked into the hotel totally dressed, no one seemed to care or notice. The next day was a hot one so I dressed in a light skirt and blouse (note a long sleeve one to cover arm hair, I had shaved my legs). Along the way I stopped and did some shopping and decided to purchase a bathing suit one that covered as much as it can (skirt type and high back). That evening I waited for the right time to go to the pool when there was no one around (late), what a trip. A young couple joined me while in the pool, but they stayed at one end doing there thing. I was able to get out and cover with a large towel with out incident. The next two days were again wonderful in that I was enjoying myself doing some of the day to day things dressed as a women. Being careful of course. One day when I was on the phone an calling for a reservation I could tell the gal on the other end seemed not sure when I spelled my name “Clara” with my voice, when I checked in that evening there were to gals at the counter and it was very busy and lots of people in the lobby. I over heard the one gal say to the other (you spelled it correctly “Clara” she is a women, again what a trip and whether they really noticed or not, they treated my as one.
Take some chances, be careful but be yourself.