Back in the late 80's I worked with a guy that loved to cross dress and since we were in an office where we did not see customers walking through the door, the boss gave him the okay to do so. After the initial shock of it all, he was just accepted as another office worker. No special treatment and although he was talked about behind his back it was not a big deal.
I was able to talk with him some and gained a better understanding of transgendered people.