My SO has quite an extensive collection of femme clothing, and recently put his closet in order. Yesterday was snowy and we didn't have many errands to run, so it was "shop in his/her closet" day! I had been looking forward to this for a long time, and it was worth the wait! It was so much fun trying on clothes and hearing "you look so hot/cute/pretty" over and over. Pretty soon into the adventure, I tossed one of the dresses at him and then the comments were coming out of "her" mouth.
He is a lot taller than I am, but I'm curvy, so some of the shorter skirts and dresses fit me quite nicely. Now my going out wardrobe has expanded considerably! On the other hand, it also prompted a trip to Kohls to bulk up his supply of panties...after all, if you're going to dress up, what's underneath counts too!
I'm happy to have this forum to tell my story too; it's not fodder for my Sunday call to Mom and Dad