My story is one of both frustration and minor adventure. My frustration is that of a generally wonderful spouse who will not endorse my cross-dressing. The adventure is that of occasionally getting a chance to express my other self. Let me get past the physical part. I am 41, short, over weight (size 24) and generally not really attractive as either male or female. I began my cross-dressing as a teenager and have continued it very sporadically since. My wife discovered my activities due to my carelessness in cleaning up after removing my makeup. The discovery never deeply threatens our relationship, but did result in her expressing a desire to not participate. A comment that she has reaffirmed more recently.
Prior to last year my adventures never exceeded leaving the house, going on short drives, or shopping at a few very private small stores. A couple of times I took feminine clothes on business trips and drove around without leaving the car. I found the process of getting from the room to the car very frightening.
I did develop a very good relationship with the owner and sales people at one store. Betty made it very clear that I was welcome anytime. This store had always invited me to try on anything I had shown an interest in buying. One day a sale clerk slipped and used a masculine pronoun. This action seemed to cause her much embarrassment, but it did lead to about half an hour of discussion with her and the owner. This allowed me to ask a couple of questions that I otherwise could not have asked. I found out that they had figured out my true gender from my voice not my appearance. That they were not worried that my appearance would disturb other patrons (they said no one would notice unless they talked to me), and that they thought that I had quite good taste in clothing. They also told me that I had worried them a little initially until my questions about their merchandise had made it clear that my interest was in buying clothes.
This pattern changed last year when business travel caused me to travel almost every week for five months. After a few weeks of travel I found that I had many free nights. I packed some of my feminine wardrobe and started dressing after work in the evening. At first the pattern was the same as before, but after spending most nights for a couple of weeks either in the room or just driving around I found myself getting kind of bored. The question was what to do. I decided to try to find a few new places to shop. This turned out to be more difficult that expected. All of the stores where in big shopping centers or malls with lots of people. I spent a few evenings too scared (including that adrenaline-induced sweats) to go into any place. Finally, I decided it was time to either go forward or give it up. So I pulled up to a pleasant but relatively crowded plus size store and just walked in. The store had several shoppers, but beyond the clerk who asked if I needed help no one took any notice at all. After shopping for about 20 minutes and not finding anything that I wanted I felt fine, but nervous. As I left the clerk invited my back with a "See you again soon."
The second store was easier, at this store there was really helpful clerk who pointed out many items of interest and invited me to try them on, which I did. Dawn was very personable and since we shared approximate dress size offered a number of suggestions and recommendations based on her personal experience with the store's product line She even talked me out of buying a girdle that she felt was ineffective. I shopped at this store often over the next few months. At some point Dawn and I were having a protracted conversation where the topic of my gender came up. I had been assuming that they knew and they did, but no one cared. It was an important moment for me. Dawn and I had been standing at the front of the store in plain sight to anyone coming or going and no one either noticed or cared.
Dawn told me not to worry I would be welcome most places because on casual inspection people would not notice and people making closer inspection would continue the pretense as long as I did. That moment told me that I could go other places and try other things.
I started to get a bit bolder and no longer hesitated in going to clothing, accessory or makeup shops. No one caused trouble, laughed, or seem to care much at all. Still I could not work up the courage to go to the mall. I think the thing that scared me the most was the thought of being in the middle of the mall with a bunch of teenage boys causing trouble. (I was a teenage boy and teenage boys will do anything). I reached another milestone when I went to a Cosmetics store one day and met Gwen who did make overs. I originally was shopping for a simple lipstick, but Gwen told me that I should try a make over. I agreed that this would be fun, but was a little reluctant since this would require me to sit in a reasonable public spot as we removed and then reapplied all of my makeup. I figured that I better mention my gender to Gwen before finalizing my appointment, since while I might have fooled her for the short conversation until that point, I certainly would not after taking off all of my makeup. She acknowledged she had identified me, but told me that I should not worry about it. She said that she had a number of cross-dresser as customers and only had a few guidelines for dealing with cross-dressers such as; they only dealt with males that came dressed as women; they must pass as female on casual inspection; and they must be polite and accept that they could not make most people look like Cindy Crawford. We made an appointment for the next day and then chatted for a while until her next customer came into the store.
The next day I had such a good time as Gwen redid my whole face with a proficiency that I am certain I will never match. Gwen was a model, makeup artist and instructor. She also had an enthusiasm that was a lot of fun. She did not do anything drastic, but did suggest a more subtle approach. It was fun.
Several other customers came in during the make over, none noticed anything out of the ordinary and Gwen kept up a stream of conversation designed to make me comfortable plus teaching me new methods of making myself look better. By the time were done (and Gwen had made a reasonable big sale) it was within about a half hour of closing time. Gwen said that the owner of the store would be in a few minutes and invited me to stay until she came. We continued our conversation until the owner arrived and then until 20 minutes past closing. The owner concurred that I was welcome back and reemphasized that I should not worry about going into establishments like hers. She said "Don't worry standing there or sitting there no one will have any way of knowing that you are not a woman." She also told me that they would notice if I held a conversation of any length. That was another freeing moment for me. I decided to push the envelope a little farther.
At this point I did two things that I did not think I would ever do. I started going to the mall (although I have yet to stay very long or shop till I dropped) and I started going out to dinner nearly every night as a woman. I cycled between several restaurants. All of them were excellent establishments with great staffs and superior food. Again they accepted me as I presented myself. People either did not notice or did not care about my secret. It was really to the point that I would go almost anywhere with the expectation of an enjoyable time. The only fly in the ointment was being alone. It would have been even more fun having a good friend to share dinner and maybe a show.
Since then I have been traveling and dressing much less. This is good news and bad news. I really like being at home (I quit my old job, because I could no longer control the travel schedule) and have a whole set of appropriate male hobbies and interests that keep me busy and mostly happy. However, there is the background frustration of remembering the few moths where I really got a chance to push my personal envelope.