Belatedly posting an intro -- I was too intimidated to do it until now! But this is such a generous and supportive community that I'm ready now. Admittedly much of this post is pulled together and edited from my own prior posts elsewhere on the site.
I'm a 64 year-old male who now enjoys cross-dressing, having come out to my wife about 4 months ago. She is wonderfully supportive, and after 32 years together that's of utmost importance to me.
I can't say I had dysphoria as a teen or young adult. Always admired women and have often been more comfortable in "women's" conversations at gatherings than in "men's" talk. But some time in my 50's I began to fantasize about having breasts and a full head of hair (am partially bald). For probably 8 years I secretly dressed in my wife's clothes, made my own breast forms in all sizes, and wore them around the house when she was away.
My wife "got the hint" when I proposed cross-dressing in public last Halloween. She first thought I'd do a caricature job, showing my unshaven face, bald head and chest hairs, etc. I said no, I wanted to do it seriously, and she was supportive.
Since then, she's continued to be supportive of my "exploring my female side." We've shopped for clothes together, wandered the bra aisles together (tough to find a 38B), gone in the dressing room together with all female clothes. I
borrowed her eyebrow pencil (which she now wants back -- she calls me her little sister).
I cross-dressed for the whole day at the Women's March in January. We drove up with 4 of my wife's good girl-friends and they were supportive.
She offered to take me out for a night on the town in full-on cross dressed mode for my birthday, which was fun if tiring. At our age the appeal of a dance club is significantly less than for younger folks. Need to find a good place to go out...
We went for a hike together in a local open space, with me dressed conservatively (misses jeans, wig, and a size A bra under t-shirt). To my surprise we encountered an old friend from child-raising days and had a conversation. I wasn't ready to come out and talk about it, so I'm sure she wandered off with interesting questions

I'm a trail runner, and have sometimes explored running while dressed. I used to do it only on remote rarely used trails, in winter. Now I'm more forward about it. Trying to pass as female is very difficult for my 6'2" height without makeup, so I'm sure I cause some consternation, but I just keep on going. Any suggestions appreciated.
I've come out to our son and this past weekend to my younger sister. The others have seen my Halloween photo, so at least it shouldn't be a shock, and maybe our son has told our daughter by now. I just let it come out naturally when the time seems right.
Work is about the only area where I really would be uncomfortable coming out. Although it might be pretty entertaining watching a bunch of IT geeks trying to cope. I'm highly technical and well respected -- maybe I should do it just before I retire

Ok, enough! See ya around!
Love, Randy