Originally Posted by
IleneD
I had a period prior to puberty around age 11 or 12 when I had a pair of Mom's panties that I would wear under the bed covers. The habit didn't last long and faded.
I grew up a "sissy", and was constantly reminded of my lack of boyhood manliness. Awkward, slightly effeminate, nerdish and bookish. Always had girly feelings but never understood them. You know that kid.
The REAL first time en femme was in high school. It was a huge eye opener too.
I played HS football. (Yes, scrawny at the time Me; at the literal threats of my dad to make a man of me). At the end of the season the school held a Powder Puff football game in which the girls and female cheerleaders would assume the role of players, and the men/players would assume the role of cheerleaders and the "homecoming queen & court" for the evening dance mixer.
I was selected to be one of the contestants for Powder Puff Queen. The girls of my HS made the nominations, BTW. I was no ladies man at the time, so make your own conclusions here. For the ball we had to dress as girls and ball queens.
The other boys who were contestants came dressed more as clown versions of women; caricatures. BUT.... my mother (God bless her) actually took the assignment seriously. She helped dress me for the ball, and she did so in earnest making me quite pretty. Not clownish or silly at all. She had a gold lame' long dress she gave me; a wig and of course her makeup. The works. There's a (bad) picture in my yearbook of me in my first feminine glory.
Oh... I was crowned as Powder Puff Queen.
The most stunning part wasn't just that I was PRETTY in person for the very first fascinating time, but I discovered that I was a dead ringer for my mother (when she was about my same age). My Mom was a beautiful woman too. But that image of ME as my mom, and me loving it has lasted with me all these years.