Sister And Friend Dressed Me Up
I don't remember the exact age, but I think I was about 6 my first time. A childhood family friend of my older sister came over to play for the afternoon and i tagged along. At some point they started messing about putting a simple, awful little tie-dyed shirt dress, but simply over his shorts (he did take his shirt off). He started prancing about and acting goofy and we were all chuckling at him. Just barely crossdressing. At that point they turned to lil'ol me...
They figured since he had a turn, it was time for little brother. For that, they found one of my sister's old taffeta and lace little girl dresses. Not wanting to counteract the big kids who were 'nice' enough to let me hang around, I went along with it.
They ******** me down all the way to my tighty whities because it "just wouldn't work with my shorts." (its funny how some phrases the mind latches onto) After getting the cute little dress on, they felt I just needed the white tights to go with it and put them up underneath the skirt of the dress over my white cotton underwear. Then they put on the cute, little, red saddle shoes that went with it. Topping off the outfit with little red hair barrettes, they pulled my short hair back into some form of feminine hair due. My sister even broke out some of her new red lipstick (way too deep for my age, but matched the red in the dress) and some blush. Then they gave me a little doll and just praised how cute I was & what a sweet little girl I was. Taught me how to skip and just chuckled. Then, without a thought in the world they said, "lets go show mom and dad! They'll get a kick out of you, too!"
Skipping down the stairs with my little dolly following behind my sister and our friend, air fluffing up my skirt with every step and skip. They went out the garage door first calling out to my parents and I took a step out and saw the expression on my father's face change to shock. Suddenly the reality of me being in a very girly dress hit me and a dolly in my arm in front of my father and I became very timid. They did at least say it was "cute" in a very curt tone, and suggested I go change. It was definitely deflating, but would not be my last; nor my last being "seen"... perhaps later.