I still have vivid memories from my youth of episodes that I think had a huge impact on my dressing today! They actually had more to do with the Joyful reaction of the gals to me being in female attire that really sticks out to me. Anyone have stories from their youth of dressing up in girl clothes with females involved ?
My first experience in Girl Clothes -
Ok When I was about 7 and my older sister 8 were going to get a visit from the nanny who had help raise us from birth. Mary was now in her late 70s and we had not seen her in about 4 years. My aunt and girl cousin Annie was over since Annie had spent time with her also. My Mom turned to my sister and told her to go get dressed and that she had laid out a pretty dress like Annie was wearing. My Tom Boy sister Tammy turns to my mom and says why do I have to wear a dress and Sal doesn't. My mom says to her don't be silly he is a boy and you are a girl so get upstairs and put on your dress so I can fix your hair.
Ten minutes later Tammy comes down wearing some of my nice clothes and a baseball cap. My Mom asks her what in the heck are you doing. And she responds I thought it might be fun and funny to trick Mary into thinking I am Robbie, Well my mother and aunt look at each other and burst out laughing and both agree its a great and clever idea. There is then a bit of silence and I start wondering in horror if they are thinking what I am thinking. Tammy then breaks the silence by saying so Sal you get to pretend to be me and wear " The Pretty Dress " Well they all howled in laughter but me. And my mom says oh what a great idea ! I of course said no way but my mother said oh yes.
The Dress was Yellow ,short with puffyness at the hem and on the sleeves . After putting barrets and bows in my hair I saw myself in the mirror and almost died ! I looked Like a very girly little girl and felt so weak and exposed in the dress ! I have never seen my sisters happier, they were litterally jumping up and down with glee. My Mother and Aunt just kept giggling ans using terms like Adorable and Darling ! I had to pose for way too many pictures even a couple holding a doll ! And of course our old Nanny was late and of course she too enjoyed seeing me in the frilly dress !
Again I remember just how much wearing the dress made me totally not feel like a strong boy at all but I have a greater memory of just how much fun and glee it gave all the females involved to see a boy easily turned into a Girl ! Of course for weeks my sisters and mother were always asking if I wanted to wear a dress since I looked so cute in them !
Any thoughts or similiar experiences ? I have a couple more experiences but I will wait and see if there is interest