Will,
I was in your shoes, pardon the pun. I too love heels and boots especially. I was unsure of how my wife would react to my desires, but it has been about 8 years and I have about a dozen pair of boots and all is good. I can't remember exactly how I introduced her to my wants, but I can tell you that you need to start off with something not too outrageous. Try some calf boots with block heels that aren't too tall. 2-3 inches. Shoes seem more feminine than boots in my opinion and the block heel is easier to walk in and cowboy boots have them, so that helps.
I would wear them around the house, but not everyday. You don't want to force them on her. After a while, I got more boots and I didn't want to hide them, so I talked to her and asked her thoughts. You MUST include her, don't just go about what you want and ignore her. As time goes on, you can tell if she is accepting of it, or maybe she will never accept you wearing heels. After you get your first pair, wear them and see how long it takes for her to say something. Tell her that it is something you always wondered about and wanted to try them on a trial basis. They were "On Sale" and you couldn't pass them up!
Remember, baby steps and include her, but not too much. She might not mind you wearing heels, but might only want a limited amount of participation.
I hope this helps. It is one of the hardest things you will do, but it will be worth it. Just realize that your desire to wear heels might be a deal breaker for her, so be prepared to make a decision; your wife or heels.
Boot Guy
