I may have had an easier path than most. Before my wife and I were married, we worked at the same company with a lot of interaction on common projects. I was married to someone else and never discussed dressing with her although I was burning to get back in the game.
My now wife and I had a torrid affair back then which naturally wrecked my marriage (we are all close now in case you were wondering). We hadn’t discussed crossdressing at that time. But my now wife had been exclusively with gals from the time she was in high school and through college and into her career. We were incredibly attracted to each other and still are.
When I came out to her as a crossdresser before we were married, it was a shock but she quickly got over it. The best thing… we are about the same size!