I have been a secret crossdresser and somewhat ashamed of myself for many years.
A couple of months ago I went dress shopping as a male. I would explain my purchases as a costume I was putting together. One of the salespeople said they hope i enjoy my purchases. I decided I would. A week later I went back wearing my purchases and had my picture taken. I also found I pair of high healed boots I really like, these, along with a rather slinky grey dress have become my "bar" outfit.
I have found that shopping dressed is so much more enjoyable. Now I get to try on dresses to make sure they fit and browse the racks. No one seems to notice or care.
I have also now gone to several bars. True I don't pick ones that are really crowded. I make it clear from the start I'm a guy in a dress. To this point no one has cared, and some have invited me to have a drink.
It is so nice to feel I have the opportunity to be me