I am a 65-year-old crossdresser. I do not identify as a woman most of the time, and yet there is a feminine side to me that I do not get to express as fully as I believe that I should. I have crossdressed for many years, but only in the last few have I tried to get more serious with it, now that I have retired. Basically, I have begun very carefully trying to take my dressing more public. I believe that I should be able to express my feminine side without reprisal and hopefully without concern.
My dilemma is this. I want to tell my dentist about my dressing, in order to see if she would support my desire to come to the appointments dressed as a female from this point forward. I don’t want to harm my relationship with my dentist, but I am hopeful that she would encourage me to dress as I want. My thinking is that once I have crossed this bridge and agreed to always come dressed as a woman from now on that it will provide me with a true success in my quest to become accepted dressed as a woman.
The idea of telling my dentist is (in the hope that she not only accepts the idea, but actually encourages me to dress when I have appointments) will also force my hand, so to speak, and create a situation where I am committed to dressing when I go see her. I go to the dentist three to four time a year these days, and it would help me to become more comfortable dressed as a woman. If I could pull it off, it would help me as I further embrace my feminine side.
I don’t know if I could ever get the courage to come out to my dentist, despite how wonderful she is as a dentist, but for some reason I really, really want to. Is the risk to this positive relationship worth taking this chance?