I didn't have many (any?) relationships with women through school and into the work force. I studied, played sports, & worked hard as an engineer in a growing company. The team of 20 something engineers was young and dedicated. As the guys eventually met women and started getting married, I just played golf and drank lots of beer. At that time (80's and early 90's) cross dressing wasn't in vogue. I lived in fear, but started to buy some things from catalogs and purged a lot, afraid I'd get caught in my own place (?). Money wasn't much of an issue.
When I met my wife, (waitress at my hangout) we became great friends. I bought a house, she moved in, and I was in a quandry. Neighbor grew into a great friend and they had a son. Now I saw the love and purpose of parenthood. We got married (mid 90's) and I vowed to be a great husband and dad, and never to dress again.
Yeah. That didn't work out so well. After about 5 years of sneaky CD'ing, I drank too much wine and spilled the beans. She was disappointed, mad, cried, and didn't understand. I got the "If I would have known, I wouldn't have married you comment." What's crazy is she is generally very kind and had been very supportive of some gay friends. (i.e. open to (some) alternative preferences) We eventually became a DADT couple and are raising our 3 kids without much passion.
She's off with the girls at a college orientation and the boy is travelling on a soccer tournament so, time to play. After work I dressed in a pretty yellow pastel floral maxi skirt, a white cotton top, and 3" beige sandals. My makeup was pretty neutral browns with pink highlights and nails. Feeling very pretty in the summer sunshine.
After dark, I decided to dress for the evening. I took some retro wide leg pants from a silky black pantsuit (again, looks like a maxi skirt) and added a black lacy wide neck top. Went back and forth a couple times on open toed or basic black 4" heels. Settled on the open toes cuz they are more comfortable. Changed the jewelry to add more sparkle, put my hair up in back, and moved the makeup to a grey smokey look. HOT, if I do say so!
I've accepted the fact that I have no answers. It seems every person, every relationship, every situation is unique. It seems that being open and up front is probably for the best, but I've lived enough to know that's easier said than done. Just keep swimming, Marlin. I think it will get easier as the light of day shines on the concept of diversity. Wives and CD'ing husbands might just actually be vogue one day. I probably won't live that, tho.