You really know you've been crossdressing for a long time when you.......
...stop caring about what underwear you are wearing to the doctors office.
...when you don't don't have any male underwear at all.
...when you have more dresses and skirts than your wife.
...when your wife borrows some of your clothes.
...when your wife need pantyhose and helps herself to what she needs.
...when you tell her about a good store to shop at, and where to purchase those hard to get sizes.
...and last, but not least, when you know more about fashion, and fashion sense than your wife. As in she seeks your opinion, because you are more in the know than she is.
