NOTE: Really long post.
tl;dr I came out to my wife and she has been amazing
I have been wanting to share my story, and started to post this in the ?worst way to get caught? thread, but this turned out to be the BEST way to be caught, so I?m posting it separately.
I have been married for a little over 40 years, and early on my wife and I were watching a movie or TV show that had a crossdresser, and I (jokingly) asked her how she would like it if I cross dressed. She said she wouldn't like it. Thus, I dove DEEP into the closet and kept my crossdressing from everyone. There were a few close calls, but she never found out. I would only dress when she was out of town, or when I was travelling for work (which, pre-covid, I did 35-40 weeks a year).
Fast-forward to about 3 years ago. I come home from a trip and she shows me a denim skirt and asks if it's mine. I would not and cannot lie to her, so I said "yes, it's mine." She said "Oh, I thought it might be [her cousin, who had been visiting recently]'s, but she said it wasn't hers". Turns out when I was packing for the trip I left it on the bed. She wasn't upset, and asked me (as spouses do) if it made me feel more relaxed, etc., so I said yes, which was true, of course. We didn't really discuss it for a week or two, but I was relieved there was neither coolness nor tension in the air. I breathed a huge sigh of relief internally that she hadn't freaked out. Finally one day she asked me if I wanted to talk about it (or maybe I asked her, can't remember), and so we did.
It turns out I couldn't have a more supportive wife. Among other things, she says she wears pants and casual clothes most of the time, and never wears heels, so is SHE a cross dresser? :-). She almost immediately starting giving me fashion tips and some of her spare makeup. I had never tried makeup, because I had no idea how to do it, and didn't want to add to the stress of emergency changing back to male. My stash came out of the attic which was a PITA to access, and now I have my women's things in my office closet, both hanging and in some tubs, and in my dresser in our bedroom. I never dreamed that would be possible. I mean, I was talking about having to make new boobs out of rice, and she suggested I get real forms. I just put my bras and panties and other clothes in the wash with everything else. They're not women's clothes, they're MY clothes. All of this blows my mind.
She has been amazing. She has bought clothes for me, bought me makeup, helped with hair and makeup. She's told me which tops to toss out because they were a terrible color for me, etc etc. Even before I came out to her, we went for pedicures and she had suggested I get my toenails painted. We always go for pedis together now.
In the past I went out stealthily, as most of you have done, but with no makeup and with homemade forms. Since coming out I have gone out with makeup, fingernail polish, etc. I first starting going through drive-throughs, but then got a little braver.
My "breakthrough" was when I went to the beach for a few days to give us both a break from being cooped up 24x7 due to the pandemic. I took more womens' clothes than my normal maie stuff. I drove there in male mode, but once I got there dressed, did a little makeup, did my nails, and stayed dressed the whole trip (3 nights). I went into convenience stores, picked up Chinese food, ordered at a drive-in with a walk-up window, walked on the beach, etc etc. I was in heaven, pretty much. The pink fog stayed pretty thick, so I checked out of my motel and drove home en femme. On the way I stopped at a rest area, which I never had the nerve to do before. I was wearing my denim skirt, a burnt-orange long sleeved cotton top, black tights, and tan suede booties. As I walked in the restroom building, I saw a GG and thought "oh-oh, I'm busted here", but I was kind of looking around, so she said "you go this way", and pointed the way to the ladies' room. Naturally, I obliged. It was an amazing feeling. Later I stopped at McDonald's and used their ladies' room as well.
This story gets better. When I got home, my wife needed to go to a thrift store in the next town over. I asked if I could go, and she thought about it a minute, and said "sure". So we did, and we shopped together we me dressed. That was the first time I had ever been out of the house with her. It was, of course, non-eventful. No torches, no pitchforks. Since then, she has gone out with me dressed a couple more times, usually to a coffee shop I like, and our favorite thrift boutique. She says we should go downtown for a drink soon with me dressed up. I have also been going out dressed solo every week or two, locally. I even went into a grocery store and picked up some things, which I had been worried about. As usual, it was uneventful.
So, long story short, I finally came out to the best wife ever, my crossdressing life is suddenly amazing, and all because I left that skirt out by accident. This was the very best way to get caught. And it's still my favorite skirt.
