First Time Out
I was about 11 years old. Halloween rolled around and of course at that age I wanted to go trick-or-treating and at the same time I didn't. So its Halloween and I have no costume. My old sister ( 8 years older ) dressed me in a skirt and blouse, tied my hair in a pony tail ( back the all boys my age had long hair ) and did some makeup.
I remember a neighbor kid running up behind me yelling "what do you have on under there?" and he flipped my skirt up. I was wearing regular boys tighty whities. I was so embarrassed at that point I went home to change. But by the time I got there I was less embarrassed and more excited. I went into my sister's room to grab a pair of her underwear. My little boy dicklet was hard as I stepped one foot into the panties and saw my sister standing at the door. She said "well little brother you may as well finish the look." She was really cool about it and even suggested I wear tights. She looked through her drawer and came up with a pair of white tights. She handed them to me and I fumbled around with them trying to figure out which end was up. She said "here.. let me help you" I sat on the edge of the bed with my little dicklet still sticking out while she worked first one foot then the other into the tights. Then I stood and she worked them the rest of the way up and fixed my skirt.
She said, "there.. now don't you look cute little brother."