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I don't know what I was thinking, or if I even had thought about it. It was Halloween, 1965, and I was thirteen years old – right at the age where I was maybe too old to trick or treat, but young enough that I was still willing to 'work' for the candy. The problem was, I had no costume, and no ideas. And back then, if you weren't in costume you didn't get candy.
My older sister made a comment that I could go as her, which made me laugh. She was, well, obviously, a girl, but she was good looking, confident, and smart, and I was none of those. But my younger sister, who did all she could to not be anything like me or our sister, thought it might be fun, but only if I had enough courage to pull it off.
I didn't want to be called a coward by my twelve-year-old sister, so I said I'd think about it. My biggest concern then was what my dad would say. Not what, I had a pretty good idea of what he'd say, but more important, how he'd feel about it. But when he was putting on his work clothes just before dinner I realized that he was just starting his two weeks on night shift and wouldn't be home. I told my sisters I would do it, as long as it wasn't too crazy.
After dinner, we met in the room my sisters shared. I was told I couldn't wear long pants, and it wasn't very cold anyway, so I showed up in shorts. They had me take my shirt off (something I was uncomfortable with but saw the need) and my older sister showed me the blouse she had picked out for me. It was colorful, I think now the word that would best describe it would be flamboyant, but before I could put it on I needed something for my chest.
I hadn't thought of that, and almost quit right then, but it was my younger sister who provided what was needed. She called it a training bra. It wasn't as much a bra as something to just provide her with a bit of camouflage, protection, and support as I recall her saying. It didn't look like a bra, that's what was important to me.
The skirt was the hard part. My older sister was into miniskirts at the time and that was what she had for me. The biggest problem was that I was taller than her, and the skirt that came seven inches above her knee was ten inches above mine. They waited while I went back to my room to change from shorts into a bathing suit.
Then came the makeup. It wasn't much I guess, but when I looked in the mirror my face was completely transformed. I did look more like my older sister than myself. The last part was a wig, supplied by my mother. It was short, as was the style then, but longer by far than my own hair and blond instead of my dirty brown colored hair.
I was nervous as I left the house, not sure if I really was up to it. I had a paper route, so I started with some of houses on my route where I knew the people and how old their kids were. The first couple of houses didn't recognize me (one woman said, "Our carrier has the sweetest dimples," I recall, not something any teen boy wants to hear,) and two of them were positive I was lying about who I was when I told them until I took off the wig. That gave me all the confidence I needed.
I left my street and went to an area that was a step up financially from my street and was known for better candy handouts. But it was a calculated risk, for it was also the area where a few of the kids who were less than nice to me at school lived.
I was doing fine, nobody recognized me, even when we passed close, and a few boys were giving me the once-over, looking at my legs. If they only knew what was hidden under the skirt, I thought to myself. But my luck failed me when I got to the top of the hill. As I passed the house that Jim lived in I saw him sitting on his front porch, but not until I was half way up the driveway. Jim was a boy who had made my life miserable, and an incident in the boy's locker room after gym was still fresh in my mind. I turned and headed back towards the sidewalk.
"Hey, do I know you?" I heard him call. "You look familiar."
I wanted to run, but that was my trademark and he'd know for sure it was me if he saw me running the other way as soon as I saw him. He caught up to me when I was nearly to the house next to his, and he wasn't alone. A boy from three doors up from him, Deidrick, was with him. Deidrick was a year younger than Jim and I, but that didn't stop him from coming up with his own little twists for making my life horrible.
"What's your name?" Jim asked. He was studying my face, trying to place where he knew me from. I could only hope that my costume would protect my real identity. But now I had a new challenge. I had to speak, and although my voice hadn't deepened yet, it didn't sound anything like any girl's voice. I did my best to tell him I went to school at All Saints and not the public school.
"You do?" A girl who was just passing by asked. "I don't remember seeing you there. What grade are you in?" Just my luck, lie about a school I didn't go to only to have someone who did go there right next to me.
"I just started," I said, trying to pitch my voce up. "I'm in eighth grade."
"I know that voice," Jim said. "I know I've met you before."
I needed to get away before he realized who I was, but the girl wasn't about to let me off that easily. "What homeroom are you in? I'm in eighth grade too and I didn't hear about any new students."
"Excuse me, but I need to go," I said. But it was too late.
"Kurt Duggar," Jim said. (Note – Not my real name)
Before I could move he grabbed the wig. Deidrick positioned himself to stop me in case I decided to run.
"Oh, you're a boy?" the girl from the parochial school said with surprise.
"If you saw him naked you might not be so sure about that," Jim said, ever ready to humiliate me in any way he could. "And he goes to our school, not yours." He stood back looking at me. "Dressed as a girl. Good costume, bad idea." And then a gust of wind blew across us, and he glanced down as my skirt lifted.
"I've never seen a girl wearing long green underpants before." He grabbed the bottom of the skirt and pulled it up, revealing my swim trunks. "Those are boy's clothes. Girls don't wear them. They wear panties. Take them off."
"I'm not taking them off Jim," I said, not sounding as brave as I wanted it to sound. I should have kept track of where Deidrick had moved to, because when Jim pushed me back and I fell over where he was on hands and knees behind me. I was quickly relieved of my bathing suit. I looked around and saw I was the center of attention of seven or eight other kids, a few of them close to my age. And the skirt was pinned under my ass and over by belly. With the bathing suit gone, I had nothing to hide my privates, not that they were big enough to need much hiding anyway.
Jim held me long enough for all the kids in attendance to have a good look and then in my bag he dropped the candy bar he had brought for me when he thought I was a girl. He stood up and tossed my suit up into a tree branch.
I might have been able to get it down, but it would have involved jumping, and with nothing on under the skirt, jumping was not a good idea. As it was, the skirt was higher than mid-thigh and every gust of wind would raise it with the possibility of showing that I had nothing on under it.
"Hey Deidrick, I've got to hand out candy at my house, but why don't you accompany Kurt, I mean, Kathy to all the houses around here. Make sure her bag is nice and full before she goes home, okay?"
"Sure thing Jim," Deidrick said. "Here, you can fill my bag too," he said, putting his bag into my empty hand. His bag was a bucket, and I had to hold it out to the side or it would lift the skirt with every step I took.
I should have run. I could have, even as skinny and weak as I was then I could probably hold my own against Deidrick. But he was smart and I knew what he was thinking. Lift my skirt and every kid around would see I was naked underneath. That would take all the fight out of me. So I went with him, house after house.
I should have at least been able to keep the candy I collected, but Deidrick demanded half of my bag. As we parted, half an hour after I was supposed to be home, he did lift the skirt as high as he could before running off. The only good thing was the streets were empty of all the little kids by then, but there were still a few older kids and teens around and some of them did see.
My younger sister had heard that a boy dressed as a girl was collecting candy. And she heard that the kid didn't have any pants on. She laughed when I came home as she lifted the back of the skirt and exposed my bare ass as I ran to the safety of my room. It was the last time I ever went trick or treating again. And I swear, every word of this story is true. I didn't even change Jim and Deidrick's names.
The End
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