I'm one who came relatively late in life to "giving in" to the desire to wear feminine clothing, although if I'd been generally less inhibited (by self of circumstances) earlier in life I'm sure the desire would have grown sooner.
I did have a couple of encounters, however, with cross-dressed gurls.
1) Walking through the college campus I passed a group of students, gathered around one of their friends (I take it!). They were cheering and celebrating, and in their midst was what I am sure was a MtoF out on I guess, her first outing beyond her bedroom. I cann't at this distance in time recall what she wore beyond that she had long hair (I guessed wig) and a small (fake?) fur jacket. My reaction??? Not horror and outrage but "Hey. That's nice, they're being really good freinds supporting (him) like that. Good for (him) too!!" (brackets for my actual thoughts AT THAT TIME). I "read" her but was happy that she was having fun.
2) I was preparing to take part as a cousellor at an Evangelsitic meeting (soccer stadium!) and went to the final training session with some college friends. Also there was someone who could have been a strangely very shy woman, but who I sensed was in fact a "tranny". I assumed she was there for the same that I was, and so just got on with the activity requested of us. When we were asked to pair up/form small groups to talk about some issues I ended up paired with "her". But she would not speak:so I got no practice in whatever was required, with her.frustrated:, Shame. I guess that convinced me I was right, and he knew his voice was not "passable". But then...silence hardly helped in "passing" and frankly a male voice would not have bothered me.
So, any one else with such tales to tell from the days before YOU came out of your mental closet and joined the merry throng of dressing "us"?