I told my wife about my appreciation of TG fiction when we were dating but when we were married it was pretty much DADT.   I did buy and wear VS PJs for sleeping, as they fit wonderfully on me.  It was just clothes in my early years, as I had no appreciation for style and fashion. But, I learned how to dress better for work as she was worried about my job as I got older. It was really hard, as male clothes are a poor fit. Men's XS is a cruel joke. She suggested wearing women's dress shirts. Through Ebay I got a nice collection of J Crew shirts, back in the day when they were quality shirts.  Then I watched the Devil wears Prada!  Wow!  I've now watched many scenes countless times!  She passed a few years ago.  Just recently my barber retired and my cat passed away.  Why not buy a bra from Target? A 32AA bra fits perfectly.  Then I shaved my legs just before the Amazon Prime Sale.  Whoa!  I was trapped in the PINK FOG!  I bought a pair of black kitten pumps, a little black dress, and hose from Target.  It's too warm for the hose, but everything else fits perfectly! And I'm dressed as I write this!