The closest I come to this is my fantasy of being a young newly post-op girl and still living with my parents and going out on my first date with a guy who comes to pick me up and my dad being somewhat overprotective of his new daughter insists on meeting. A whole bunch of new firsts like having a car door opened for me, holding doors open, having hard time keeping up with him because i'm wearing heels, he holds my hand and ultimately my first kiss as a woman. Other fantasies have involved losing my femalw virginity and going to a wedding with a date. Basically all the girly things we fantasize about doing.
But I could never be with a guy just dressed because I still know I'm a guy too and that's a little gross to me.